Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: Baby Bobby on November 23, 2023, 10:26:00 AM
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It was a cold, grey day and the rain was coming down in sheets, heaping only further misery upon me as I trudged slowly and alone through the downpour.
Three weeks ago, I had been recently orphaned, due to a tragic car wreck involving both of my parents, and my arranged social worker recently set up living accommodations at my aunt’s house, some 80 miles from where I’d lived for the last twelve years of my life. It had been a trying ordeal for me and after the last horrific month of trying to cope with being without them, I was beginning to think that I could not possibly be more alone in the world.
Unfortunately, I had only spotty memories of my mom’s younger sister, Aunt Emily. The last time I had been there, I had only been five at the time and it had ended on a bad note for everyone involved. She seemed nice enough, and as I recalled, and she was quite pretty, or at least, she was at the time.
For some reason on that occasion—perhaps because there were no other toys around--I had found myself playing with a collection of Barbie dolls my Aunt had left in a room. She had come in unexpectedly while doing some laundry and discovered me on the floor but instead of teasing me, as I would have expected, she sat down and joined in as if it were perfectly natural. Things had continued quite pleasantly that afternoon until my dad came to pick me up to go home. To my shock and horror, my father was livid with what he called my “sissy” behavior and he let me know in no uncertain terms by pulling my pants down and spanking the daylights out of me. After that painful experience, I was absolutely forbidden to have anything to do with Aunt Emily and I had kept my word for the last seven years.
That traumatic episode, early in my impressionable young life, caused me to be all the more uncomfortable about going to live with Aunt Emily. Would she be wary of me now? Maybe she resented my moving in so unexpectedly? But I had nowhere else to go—there were simply no other relatives for me to turn to.
My shoulders trembled as I choked back a sob of self pity. The walk from the bus stop to Aunt Emily’s house had left me soaked and chilled and I was feeling little incentive to move in with my enigmatic aunt, a person who was still little more than a stranger to me.
The heavy suitcase I was carrying was beginning to hurt my arm so I set it down momentarily to shift it to the other side. As I did so, I pulled out the crumpled note the social worker had given me with Aunt Emily’s address written in the lady’s elegant cursive writing. As I smoothed it out to re-read it, the rain immediately began to make the ink start to run and I feared I’d lose the information forever. In my anxiety and panic, I burst into tears and scanned the nearby houses, searching desperately for the address while I could still make it out on the slowly disintegrating paper.
To my utter relief, I saw behind a nearby white picket fence, the five numbers that corresponded to the address I’d been given. Wiping my face of rain and tears, I re-shouldered my burden and went up the path to the large, ornate wooden door. A glazed window was next to the door but warm light was spilling out through it and it beckoned from inside, seeming to invite me to inquire further. With my heart in my throat, I knocked uncertainly and waited for what fate had in store for me.
Barely three seconds had passed when I heard the unmistakable crisp sound of heels steadily approaching from inside. I bit my lip nervously as the big door swung open to reveal my aunt standing before me.
“Joshy!!” she exclaimed with unrestrained affection.
Without waiting for a response, she bent down and threw her arms around me, locking me in a warm hug, filled with love and promise. Stopping only long enough to plant a wet, lipstick-covered kiss on my cheek, she pulled me inside and began immediately shedding the sopping wet clothes off my body.
It seemed like it had been a lifetime since I had seen my aunt but now that I was seeing her again, I was very pleasantly surprised. Aunt Emily was like an angel from heaven—tall, slim and pretty, with long sensuous legs that she showed off to great effect between her high heels and the snug skirt that clung to her curvy hips. Her long blonde hair spilled over soft shoulders but did nothing to hide the bountiful, plump bosom she could barely contain within the snug top that wrapped around her chest like a second skin. This was an aspect of my aunt I had apparently forgotten but I certainly wouldn’t forget it now, for as long as I lived!
For some reason, I had always had a strange fascination for big breasts, or at least since the time I had begun noticing the opposite sex during the last few years. And it seemed that well endowed, busty women struck a visceral nerve within me, on a level even I didn’t understand.
Now, as I gazed in bashful silence at my stunning aunt, I was captivated by her plump, sexy bosom, causing my little wiener to rise up in salute to this devastating creature before me.
“You are absolutely soaked!” she gushed in a voice that was like the playful notes of a happy song.
She removed my jacket and shoes and then began taking off my dripping socks as well. Leading me into an immaculate, tile covered bathroom, she continued undressing me even though I had thus far, been unable to utter a word!
Being shy by nature, I was quite unused to being around such a striking woman as Aunt Emily, to say nothing of being undressed by her! Finally, I found my voice and I croaked out a greeting as best I could in a small, shaky voice.
“H-hi, Aunt Emily,” I said, a tentative smile coming to my face for the first time.
“Well hello, Honey-bunch!” she said gleefully as she gave my cheek an affectionate squeeze, “It’s been a long time, hasn’t it?”
I was relieved beyond words that my aunt seemed pleased to see me and my tension began slipping away like the wet clothes gathering in a pile at my feet.
“I was just about to take a bath when I heard you knock at the door, but you are obviously in greater need of it than I am—let me just get you out of these freezing clothes,” she explained.
The steam was rising visibly above the huge layer of bubbles that covered the surface of the tub but when my shirt was removed and my aunt began to unbutton my pants, I suddenly put my hands down to stop her.
“Oh…I-um, I can take it from here,” I stammered.
“Nonsense Silly,” she scolded me in a friendly tone, “I used to help change your diapers so you needn’t be concerned—I’ve seen every inch of your little body.”
I blushed hotly but I only vaguely remembered being around my aunt during my preschool years and I was reaching the age now where I was extremely self conscious of my body. The last thing I wanted was for my ravishing aunt to see my wiener, particularly since it was stubbornly refusing to go down!
Before I could say another word, Aunt Emily unzipped my pants and tugged them down my clammy, hairless legs, exposing my small erect pen-is within my clinging underwear.
“Oh my,” Aunt Emily said with amused surprise, barely suppressing a giggle, “looks like someone’s a little excited.”
My face turned beet red and I grabbed hold of the waistband of my underwear in an attempt to prevent any further undressing but my aunt was undeterred. Her hands were slim and beautifully manicured with long nails done in the French style of a model. She slapped my hands lightly and in my surprise, I jerked them away, just long enough for her to tug my damp underwear down my legs.
Now it was impossible to hide my erection and it stood proudly, if not insubstantially, since it was no more than an inch and a half in length, even by generous measurements. Aunt Emily giggled again but paid it no more attention as she led me into the tub where I gratefully sank into the mass of fragrant bubbles.
Taking a rose scented bar of soap, Aunt Emily began lathering it up and she started to rub it over my youthful body while she hummed a pleasant tune. I tried once to take it from her, but again, she merely pushed my meddling hand back down and resumed her ministrations as if I weren’t even there.
Washing me as if I were just an infant made me feel all the more helpless, and despite the fact my privates were now hidden, I still felt a sense of embarrassment.
“I can remember giving you a bath when you were just a baby—do you remember Joshy?” she asked sweetly.
I didn’t know why she insisted on calling me Joshy but I wasn’t prepared to make an issue of it so early in my new relationship with her. In any event, I was still too distracted by her loveliness and charm to think of arguing with her. In addition, it felt wonderful to have such a gorgeous woman using her soft, creamy hands to wash my sensitive skin. It tingled like electricity at her caressing touch and my erection certainly hadn’t gone down—if anything, it was raging even harder! I was gazing down between the two huge globes beneath her thin, stretching top as her slippery hand suddenly found itself down between my legs. She squeezed my boner briefly and then began slowly massaging it with the bar of soap, sending shivers of excitement down my spine. Breathing hard now, I stared up into her pretty green eyes, while my own were glazed with lust and pent up energy. Between her stunning face and her massive, beautiful breasts, I couldn’t take anymore.
Suddenly, I experienced an earth shattering explosion of ecstasy unlike any I’d ever had in my entire life. My eyes crossed and I gasped for breath as I struggled to understand the wonderful feeling rippling through my body. Waves of pleasure washed over me and I went weak, the intense image of my delicious aunt swimming before me as my head rolled lazily.
Aunt Emily smiled warmly down at me, a look of understanding upon her gorgeous face.
“Looks like my little baby likes his bath,” she cooed softly.
I was still drooling foolishly as I slowly began to recover from my very first orgasm. If ever there was a case for love at first sight—this had to be it. I was utterly captivated by my sexy aunt and I knew I was going to be in heaven staying as her guest.
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Wow, wow, wow ....
What a great start Bobby, you've certainly got a talent.
Always look forward to your stories ...
Ace
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It had not been more than a week since I had settled into Aunt Emily’s wonderful home that I had made several observations.
First of all was the fact that I noticed a total absence of anything manly, anywhere in the house. On the other hand, feminine touches seemed to grace everything, from her bedroom, to the kitchen, and even to the living room with its soothing pastel colors.
But more than anything in the house was Aunt Emily herself. I had never met a more “girly-girl” than her. She had an air about her that was indescribable, yet always present. Her make-up was always flawless, emphasizing her devastating green eyes with her long feminine lashes and her full, luscious lips that seemed ready to kiss me at any moment. I had come to savor those kisses, even if they were completely platonic.
She walked with a delicate, sashaying grace, especially in her high heels and her voice was of a musical quality that sent shivers down my spine. Her very femininity seemed to suc-k the manliness out of me, making me feel out of place in my new home.
But I also found myself gaping like an idiot at her lovely, mouth watering breasts on a regular basis. She seemed to be totally unaware that she was driving me insane with her tight blouses and low cut tops. Maybe it was because I was too young for her to think of me in that way. I certainly didn’t know much about women’s bodies and I wouldn’t have known what to do with their breasts even if they were made available, but they excited me anyway. I found myself masturbating furiously several times a day to try and get some kind of relief from the constant visual image of Aunt Emily that teased me on a daily basis. I had never met a woman like her in my life and she had me under an intoxicating hypnosis of sexual temptation.
The other thing I discovered was that Aunt Emily seemed to want to treat me as if I were still a little child. I didn’t mind, really, it just seemed a little eccentric though. It didn’t help that I was naturally short and Aunt Emily very tall, at least taller than any other woman I’d ever met. In her heels, she towered over me and I found myself staring at her prominent bosom which was usually at eye level for me. Several times, she had smiled down at me, placed a long nailed finger under my chin and raising it, forcing me to re-focus on her pretty face. ‘I’m up here, Sweety’, she’d tell me with a giggle and a knowing look. This only made me blush all the more, and I’d hope she wasn’t aware that my little wiener was getting stiff, yet again.
I still had a hard time holding eye contact with my aunt, primarily because I felt so intimidated by her. I had always felt that way about gorgeous women and Aunt Emily’s poise, confidence, and height, all conspired to make me feel like a helpless little boy, unworthy of her many kindnesses. I wanted desperately to please her in any way I could and I had unwittingly humiliated myself several times in my eagerness to do so. But Aunt Emily would always giggle good-naturedly when that happened and I would feel better afterwards.
My aunt seemed, for the most part, to be willing to give me free run of her entire home, a house which was substantially bigger than where I used to live. The one exception was a room at the end of the hall with a brightly painted pink door that had thus far, remained closed. My aunt had instructed me that it was off limits and because I was so infatuated with her, I respected her wishes, even though I was still very curious to know what was in it and why she wouldn’t grant me access.
I surmised that Aunt Emily had very sexy tastes in her more private clothes because I had discovered several catalogs lying around end tables in her living room. I found Victoria’s Secret, Frederick’s, and several others I’d never seen before. They excited me almost as much as my aunt, although I spent a considerable amount of my time imagining her in various states of undress, wearing the exciting underwear pictured in the catalogs. I had no idea what her bra size was but I figured it had to be incredible. This was a question that occupied my mind on a regular basis and every time I saw Aunt Emily, I found myself in a near constant state of arousal.
I also had a budding fetish with panties and besides enjoying seeing them on women, I secretly harbored a shameful fantasy of wearing them myself. I knew it was wrong but I couldn’t help myself and I often gazed at the pictures wondering what it would be like to wear a particularly frilly pair.
It was on one evening that I came across a catalog I hadn’t seen before called Prissy’s Fashions, lying face down under some others, almost as if it had been deliberately hidden. Intrigued, I picked it up with unrestrained interest and began thumbing through it. Glancing over my shoulder, I verified that my aunt was still occupied in the kitchen preparing dinner, before devoting my full attention to the fascinating magazine.
Turning the pages, I found myself enraptured by some of the unique items they sold. In the first section, labeled Sissywear, I saw youths wearing articles of clothing that were clearly designed to look feminine and well, sissyish. My heart started thumping in my chest as I gazed breathlessly at the pretty panties they wore, hugging their round, firm young bottoms. I knew this went against everything my father had taught me, but the images made me rock hard and excited, striking a nerve I had tried many times before to deny.
So caught up was I in the catalog before me, that I was completely unaware of the fact that Aunt Emily had walked out of the kitchen and was now standing behind me, observing me in silence.
Slowly, she bent over the back of the couch so she could practically whisper in my ear.
“Looks like my little boy likes panties, hmm?”
I was so surprised that the magazine fell out of my hand abruptly and I jerked around to face my aunt, red faced and ashamed.
“Oh no! No Aunt Emily—honest!” I blurted out, but my reddening face belied the truth.
My aunt smiled knowingly, her pretty eyes dancing with delight. With her usual grace, she walked around and sat down beside me, while I trembled with fear and mortal shame. As she settled next to me, her skirt rode upwards, exposing her smooth, firm thighs to the nervous boy next to her. A bead of sweat trickled down the side of my forehead as I contemplated what my stunning aunt would do to me.
“Joshy, are you a sissy?” she asked me softly.
‘N-no—no Ma’am,” I spluttered, hoping the added formality would placate her. I couldn’t face to look at her and my cheeks were burning red as it was, so I stared down at the floor in front of me, trying to ignore the expanse of smooth bare skin next to my own.
Aunt Emily smiled warmly and placed her slim, soft hand on my chin, turning me to face her.
“Joshy, are you a sissy?” she asked me again.
I could feel my cheeks blazing and I felt unable to resist this very adult woman’s intentions.
“N-no—Hon-honest!” I bleated.
“Its okay, Joshy,” she said, her voice lowering to almost a whisper, “I don’t mind if you want to wear panties.”
I was too ashamed to utter a word. I stared at the floor, clenching and unclenching my hands, wishing the couch would swallow me up and take me away from here.
Aunt Emily smiled and slowly reached down, unbuttoning the straining top button on her halter as if she were suddenly too hot. My gaze shifted as I tried to sneak a look down her top at the deep cleavage now even more exposed.
I had never seen this much of a real woman before and my heartbeat was racing like a panicked horse. The warm light of the fireplace cast deep shadows in the soft cleft between Aunt Emily’s tremendous boobs but I could still make out the clasp of her lacy white bra that was now partially visible. I could see that the fullness of her breasts were causing them to mash against one another and gulped hard with excitement.
Reaching down, she picked up the catalog and placed it on my lap, opening it back up to the page I had been looking at.
“Why don’t you show me which panties you like,” she softly suggested, her manner warm and comforting.
I was far too embarrassed to do any such thing and I tried to clear my throat, unable to speak coherently.
Sensing my intense embarrassment, Aunt Emily pointed out a pair of pink panties that were see-thru and decorated with frilly lace around the legs openings.
“How about these?” she asked softly, “Do you like them?”
I could feel my boner raging within my pants and I nodded my head even as I blushed further.
“Mm-hm,” she said, “and how about these?’ she asked, pointing out as pair of ruffled rhumba panties in baby blue.
I nodded again, wishing I could run away but also wishing I could reach down and stroke my poor throbbing peanut.
Aunt Emily flipped a page and seemed to be scanning the other choices available.
“These sure are cute,” she commented as she pointed her long, manicured nail at a pair of yellow flowered panties.
I merely nodded my head in silence, regretting that I didn’t have the courage to tell her that I loved them all.
“Well I think I’ll just order these and you can have all kinds of fun trying them on—what do you think of that?”
I was panting with excitement, both at the prospect of her suggestion, but also because I knew there was a strong possibility I might have to show my pretty aunt what they looked like on me. It was one thing to wear them in the privacy of my bedroom—something I’d only fantasized about until now—but to wear them in front of my aunt? The thought was too much for me to handle. My boner throbbed relentlessly in my pants, craving attention desperately.
With a smile, Aunt Emily hugged my face to her soft, plump bosom, patting my head reassuringly.
“Don’t you worry my little baby,” she whispered in his ear, “Aunt Emily’s going to take good care of you.”
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Wonderful i am really happy with it so far please continue his torment soon
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"Wow!" just about sums it up.
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Day by day, I found myself falling inexorably under Aunt Emily’s spell. She quickly had me under her thumb and I was finding myself unable to deny her anything. It might have been different if she weren’t so incredibly lovely, with a body that would make any grown man cry, but she was both of those and more. And she cunningly used her beauty and charms in a subtle strategy to begin molding me into a different person.
She continued to insist on bathing me like a baby, dismissing my protests by claiming that she just wanted to make sure I got “thoroughly” clean. She also instituted other changes to my living that seemed more appropriate for a child, rather than a budding man, which was how I pictured myself.
Aunt Emily insisted on an 8:30 pm bedtime and she enjoyed reading stories to me before turning out the lights. If anyone else had done that, I would have screamed bloody murder but it at least gave me an opportunity to stare uninhibited at her big, plump breasts while she was occupied with the book. After she had left my room and turned out the lights, I’d visualize her lingering image and eagerly masturbate until I had my nightly orgasm. At my youthful age, these amounted to no more than dry climaxes, with no real ejaculation, but that took nothing from the enjoyment I experienced. From time to time, I reflected that I was masturbating far more than I ever had at home, although under the present circ-umstances, I figured it seemed only reasonable. It also occurred to me that I might be acquiring some sort of addiction to wanking but the pleasure it provided always conveniently pushed that thought out of my head.
At some point, I had politely informed my aunt that I wanted to be called ‘Josh’ and not ‘Joshy’, but Aunt Emily only giggled and beeped my nose good-naturedly. An hour later she was calling me ‘Joshy’ again as if nothing had ever been said. Similarly, when I had asked for her to read me something a little more mature at bedtimes, she merely smiled and continued as before. It seemed that once she’d made up her mind about something, there was little I could do to dissuade her and I was increasingly getting the feeling that she saw me as no more than a four year old child.
Despite my differences with the way she was treating me, I was still having a wonderful time staying in her home. I might not get her to see my way about things but she was never mean to me.
Not long after I’d been there a few days, I had seen a long, rectangular wooden paddle hanging on the wall in the kitchen but I hadn’t given it too much thought. I knew it wasn’t a cheese serving tray because of the large holes cut in its surface. But Aunt Emily was far too nice to use something like that and anyway, I’d done everything she asked with only a little grumbling. It was pretty hard to imagine her using such a fearsome instrument for disciplining anyone, although if push came to shove, I was pretty sure who would win in a physical match and it wasn’t me.
I knew this for a fact when one weekend, we’d gotten into a play wrestling match. She’d quickly gotten me down on my back and pinned my arms on the ground beside my head. Happily, this had also resulted in a very close encounter with her big, soft breasts as she mashed them against my face while she kept me pinned. I had never been so close to c-umming and I only barely avoided it when Aunt Emily suddenly decided to yank my pants down to embarrass me and show me who the victor was. I blushed beet red as my hard little pen-is was once again exposed to her attention. In her usual way, she just giggled at me and let me get up, but not before giving my rump a good slap just for the fun of it.
I had been embarrassed by the experience but also tremendously turned on and I immediately went into the bathroom to alleviate my pent up horniness. I could still recall the wonderful scent of her bosom as I sat there on the toilet, blissfully stroking myself as I masturbated to another earth-shattering orgasm.
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I watched impatiently, day after day, for my panties to arrive in the mail. I couldn’t wait to actually wear the pretty, silky items under my regular clothes and I was especially looking forward to my nightly masturbation sessions in them. Unfortunately, I was far too ashamed to ask my aunt directly as to when they would arrive so I tried to do it in a oblique way, hoping she wouldn’t catch on to how important they were to me.
“Aunt Emily, did the mail come yet today?” I had asked once when I couldn’t find it on the table.
“Yes, Sweety—and no, your panties haven’t arrived yet.”
My face burned red as her giggle filled my ears and I hurried out of the room in embarrassment.
Other things were arriving as well; large and small boxes, and other things that Aunt Emily whisked away as soon as they arrived to take to her private room behind the pink door. It bothered me to no end that she had forbidden me from going in there and being the ever curious boy—I was desperate to find out what was inside.
One time, when I was walking past it, I paused outside and came close to putting my hand on the doorknob. As fate would have it, just then, Aunt Emily caught sight of me from down the hall and she gave me a brief frown of disapproval.
“Little boys that go in there get spanked,” she said simply, and I laughed nervously, trying to shrug it off as if it had been intended as a joke. However, as I wandered into my bedroom, I wasn’t so sure and I began to wonder if she were really serious. Would she spank me, if pushed? It was hard to imagine but I didn’t want to find out. The thought of having my pants pulled down and taken over her lap made me strongly reconsider opening that door. She was much taller than I was and I didn’t doubt for a minute she’d be able to hold me in place as she slapped my bare bottom repeatedly with that paddle. Nor did I want to be put in such a shameful position to receive such a childish punishment. Bent over her firm thighs, my own legs kicking wildly as she smacked my bare cheeks again and again, making me cry like a baby…I was determined to see that spankings were a thing of my distant past, particularly with my stunning aunt.
Still, the boxes and the room continued to haunt me. In those times where I’d been able to see the sending labels, I’d seen names like Babyland and Sissy World on them which made my heart flutter. What purpose could Aunt Emily possibly have for such items? I couldn’t imagine.
Finally, a week later, Aunt Emily came into my bedroom with a package in her hand and a smile on her face.
“Look what came in for my little boy,” she cooed musically.
I blushed and knew immediately that my panties had finally arrived. I was tremendously embarrassed but also extremely excited to see them first hand.
Aunt Emily unwrapped the package and carefully pulled out a pair of silky pink panties, lined with delicate lace and a three rows of soft ruffles across the seat.
“Oh—these are just adorable—aren’t they Joshy?” she asked with more enthusiasm than was necessary.
“Um-hm,” I mumbled under my breath. I had been rather hoping that she’d leave them on my bed and let me discover them in my own time but it was not to be.
“Why don’t you try these on,” she recommended excitedly.
“Um, okay…but, can I do it later?” I asked hesitantly.
“But I want to see them on you now, Joshy,” she countered, “Come on, lets get those shoes off.”
Before I knew it, she had sat me onto the bed and was untying my shoe laces.
“I-I can do it,” I tried to offer but she had my shoes off in no time and was already tugging my pants down. A moment later, I was sitting there, red-faced as Aunt Emily used her long nails to reach under the waistband of my underwear and pull them down my thighs. I grimaced as my tiny wiener came into view and I rushed to cover it with my hands.
Tossing my boy’s underwear haphazardly in the trash, Aunt Emily took the new pink panties and held them in front of my legs, beckoning me to step into them. Blushing furiously and making small sounds of weak protest, I gingerly placed my feet through the open leg holes to which Aunt Emily immediately pulled them up my thighs. I felt an electric sexual charge as the silky panties slide softly up my smooth legs. Aunt Emily was all smiles as she snugged them up my hips and positioned them around my waist. They clung wonderfully to my diminutive genitals, caressing my stiffening pen-is with a delicate embrace. Despite myself, I couldn’t prevent my erection from betraying my true feelings about the panties.
As Aunt Emily rose up to stand over me, she turned me around to look at my round, panty clad bottom. The panties were sheer so the crack of my fanny could clearly be seen through the material.
“Well,” Aunt Emily said with immense satisfaction, “looks like these fit you perfectly.”
I nodded in embarrassed silence, unable to look her in the eye.
With a casual stroke of her creamy hand over the fabric covering my straining erection, Aunt Emily smiled down at me.
“How do you like your new panties, Joshy?”
I was too ashamed to speak and I merely nodded as I looked away, hoping she’d leave me to get dressed by myself.
“Don’t you worry Joshy—this’ll be our little secret—okay?” she asked as she bent down to look me in the face.
I glanced into her pretty eyes only briefly before nodding my head vigorously and then looking away again.
Aunt Emily patted me on my bottom again and then left my bedroom, leaving me alone to savor my new and delightful gifts.
I enjoyed the panties thoroughly and I spent a good deal of my time, relishing their soft, silky feeling. And I would have been quite content to leave it at that, wearing them around the house but always under my regular pants, so that no one could tell. But one day, Aunt Emily accidentally spilled some spaghetti sauce on my jeans and at the time, the rest of my pants were in the washing machine being cleaned.
“Don’t worry Honey,” she quickly assured me, “You just take those off and we’ll throw them in the washing machine with the rest of your clothes.”
I wasn’t thrilled with the idea of removing my pants, and thus leaving myself exposed in my panties, but Aunt Emily was undeterred once again.
“Honestly Joshy,” she chided me, “it’s only the two of us and no one will ever see you in your cute panties.”
I was persuaded this time but a few days later, my aunt informed me that several of my pants had somehow been ripped up in the dryer, rendering them into little more than rags. I thought that was a little odd but I didn’t say anything about it. Also at about the same time, my supply of regular underwear seemed to be mysteriously dwindling. I had no idea where they had gone and I didn’t want to ask Aunt Emily since she always made such a big deal about keeping track and taking care of your things. I was afraid she’d accuse me of being careless and I didn’t want her to be angry with me. I wanted so badly to impress her with how much of a manly guy I was becoming and I was trying to get her to look at me as an equal, rather than just her young nephew.
But the end result was that I found himself more and more often wearing nothing but my panties and a t-shirt when I was hanging around the house. This was farther than I wanted to take my fetish and it was even worse after I’d masturbated. I discovered that I could suppress my shameful feelings about wearing girl’s panties while I was turned on but once I’d had my orgasm, my sense of manly responsibility came crashing down on me and I wanted nothing better than to tear off the humiliating undies and be a grown up guy again. This worked initially when I still had all my regular clothes but as time went on, I found myself having to go around the house more and more exposed. I asked Aunt Emily about getting some more clothes for me but she said we’d “just have to make due for the time being”.
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A classic :)
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Wonderful story as always, so looking forward to the pink door being opened to find out what delights are inside.
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Great story. Looking forward to next episodes. Hope Josh gets his wish to find out what is behind the pink door, more than just ruffled knickers I hope.
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One time, a week later, Aunt Emily suggested we play house together. This was another one of the activities that she enjoyed doing with me but to be honest, I was bored to tears by it—I just wanted to go outside and run and play with my friends. But Aunt Emily was insistent and she decided that for today, I would look good as her little girl. From somewhere, she produced a sissy looking top with puffed sleeves and a short hem that barely extended past my navel. It was pink with white lacy accents and I nearly threw a fit when she tried to put it on me. However, in the end, Aunt Emily managed to sweet talk me, assuring me that it would be our secret game and no one would ever find out. Between that heart stopping smile and her big, round breasts, I just couldn’t say no to her.
That day, I stayed inside, wearing only the sissy top, my rhumba panties and my sneakers. Aunt Emily was delighted with my appearance and she suggested we do some sewing as part of our activities.
Bringing out a needle and some thread, Aunt Emily sat me down at the table and gave me a piece of vinyl fabric to work with. Turning it over, I recognized it instantly as being a baby’s bib and I protested indignantly about it.
“Aww, Aunt Emily,” I whined, “don’t you have anything else I can sew?”
“Now Joshy,” she smiled, “this is going to be a very special bib for someone who is really close to me—I’m sure they’d be ever so happy if you were to put the finishing touches on it.”
The finishing touches consisted of putting a strip of eyelet lace around the lower edges of the infantile garment. I felt like an absolutely sissy, as I held the baby bib in my hands and careful began attaching the lace. I could only imagine what my friends would say if they were to see me now—dressed in a sissy top and rhumba panties, sewing a baby’s bib like a happy little girl. Worse yet, I was particularly horny this morning and Aunt Emily was wearing one of my favorite tops—a thin white halter edged with lace that hugged her magnificent chest in the most delightful way.
I kept sneaking peeks over at her as she hummed a song to herself, sitting across the table from me and sewing another piece of babywear. When we finished, Aunt Emily suggested we go out and sit by the pool since it was a beautiful day out. I was very apprehensive about it, even though her backyard was surrounded by a substantial wooden fence. Just the idea of being outside made me scared, given the girly clothes I was in at present.
Aunt Emily came over to my side of the table and bent over, giving me an outstanding view of her deep cleavage.
“C’mon Joshy,” she said sweetly, “there’s no way anyone can see us and it would be nice to get outside for a change.”
I licked my dry lips as I stared at the two huge melons pushed together in front of me. I could make out her nipples, poking through the fabric like two peas and my heart rate began accelerating faster. I wanted so badly to reach out and touch her soft skin but I would never dare to do something so bold. Predictably, my little wiener rose to the occasion and it strained mightily in its silky prison.
“Tell you what,” she said conspiratorially, “if you go out and wait for me, I’ll bring you out a surprise…”
I couldn’t imagine what it might be but I was so worked up by the sight of my delicious aunt that I couldn’t think clearly.
“O-okay,” I agreed shakily.
“Great!” she exclaimed as she clapped her hands together, “You go outside and I’ll be right there.”
I waited until my aunt had walked out of the room so she wouldn’t see the hard-on in my panties before I stood up and exited through the sliding glass door. I felt utterly exposed to be outside wearing such a sissyish ensemble but a part of me felt a tinge of mischievousness. It almost seemed like I were getting away with something totally forbidden and sense of naughtiness pervaded my being.
As I sat down on one of the pool chairs, I took a moment to re-picture my aunt in my mind and I stroked my little hard-on with boyish abandon. I was very close to c-umming when I heard the sliding glass door open and I quickly assumed a pose of nonchalance and innocence.
But my casual look was quickly taken away when I saw what my aunt was wearing. As she gaily sauntered over to where I was sitting, I gaped open mouthed at her ravishing appearance.
She was wearing a light pink string bikini that covered precious little of her utterly flawless body. The small bottom piece below her washboard tummy covered her feminine patch and it tied on either side of her sexy, curvy hips. I was amazed at how tiny her waist was but what took my breath away and riveted my attention were her tremendous curvy breasts, jiggling heavily within the two pink triangles of her bikini top. I had never seen my aunt in so little clothes and I was completely speechless.
Aunt Emily smiled coyly at me, holding her hand behind her back which only made her big beautiful breasts stand out even more prominently.
“Look what I have for you,” she said in a playful, sing-song voice as she brought her hand out from behind her.
I took my eyes off her magnificent chest long enough to see a new pair of yellow colored ruffled panties in her hand. A single pink flower adorned the front of the waistband and along with the see-thru shimmery fabric, it screamed out little girl, making me feel the thunder of my heart in my chest.
“Stand up Joshy,” she invited me, “Let’s see how these look on you.”
My eyes clouded with lust, I tried to stand up so my raging erection wouldn’t be seen by my aunt but it was quite impossible. She giggled as she looked down upon it but she didn’t say anything further as she held the new pair of panties open for me to step into. My face reddened but I quickly jerked my own panties down and threw them on the grass next to me. I had to steady myself on Aunt Emily’s shoulders as I lifted first one leg and then the other to get into the new panties. Even as I did, I stared down at my aunt’s awe inspiring breasts that were stretching her bikini top to its limits. My boner was so hard that it hurt and I found myself panting from the excitement. With excruciating slowness, Aunt Emily carefully pulled the panties up my slim legs, past my knees and up my hairless thighs. All the time, my eyes were glued to my aunt’s big succulent bosom, taking in every detail from my wonderful vantage point. As she pulled the soft, silky panties over my hips, her sexy breasts came right up to my face, no more than two inches away.
I couldn’t take it any longer. As the girlish panties caressed my hard little peanut, I gasped and came with a groan that escaped from my lips. So intense was my orgasm that I could barely stand and I wavered in front of Aunt Emily, my eyes rolling around in my head. Aunt Emily was smiling down at me until her gaze fell down to my crotch. Still in a foggy haze, I lazily looked down to see what she was looking at.
“Oh my!” she said, a new look of shock and concern appearing on her face.
I was certainly dazed and confused but when I looked at my crotch, I saw there was now an obvious wet spot in front.
“Oh my,” Aunt Emily repeated and she carefully sat me back down on the pool chair.
“You sit right there, Joshy—I’ll take care of this right away—I have just the thing.”
I was confused but I was also lingering in the pleasant afterglow of my mind-numbing orgasm. Presumably, my aunt had gone off to get a tissue to help me clean up the mess. I relaxed and reflected on what bliss my busty aunt had given me.
She returned quickly and she had a small white box in her hand, the size of a jewelry box. Kneeling down next to me, I caught the inscription on its face that said CB-6000S, whatever that meant. Still oblivious, I sat with curiosity as Aunt Emily opened the box and began taking out several clear pieces made of hard plastic.
“Don’t you worry Joshy; this will take care of that little problem just perfectly.”
I didn’t know how this thing that resembled a puzzle was supposed to clean me up but I remained silent and watched in bemused silence as my aunt busied herself opening a large rounded split ring. Taking down my sticky panties, Aunt Emily used them to wipe away any excess semen (which wasn’t much) and then set them down beside her.
“Spread your legs Joshy,” she instructed me.
As I happily complied, my aunt took the ring and placed it behind my little balls, circling it around so it was flush against my body.
“This is the smallest ring they supplied so I hope it’ll fit,” she said, half to herself.
Holding the molded ring together, Aunt Emily fitted the pin from the back side that prevented the ring from being opened and she placed a small spacer over the end of the pin. I was enjoying having my buxom aunt manipulating my genitals and I happily watched her as I continued to steal looks at her big round breasts. If only she knew how I was taking advantage of her, I was sure she’d be plenty angry.
“It looks like you’re a premature ejaculator, Joshy. I know those are big words but don’t worry; this will really help you with your little problem,” she told me.
With the cuff ring in place behind my sack, Aunt Emily took a clear, coc-k shaped tube with two pins at its base and carefully placed my tiny flaccid pen-is inside. Then she mated the pins of each device together and closed them up so that the first pin protruded only about 1/8 of an inch out the front. Seeing she had a good fit, she took a small master lock from the box and slipped the hasp through the exposed hole at the end of the pin. With an audible click, she closed the lock shut and sat back to observe her handiwork.
“There. You’re all set,” she said happily, “That’ll keep your little pee-pee safely locked up and it’ll also prevent you from being able to get any more erections,” she explained to me while I was only now starting to fathom what was taking place.
“Wha-what’s happening?” I stuttered uncertainly.
“This is a CB-6000S chastity device, Joshy. It’ll help you to control your urges so you won’t have any more accidents like what just happened.”
My mouth hung open as I stared down at my now imprisoned pen-is. Still in shock, I reached down and tried to pull the device off but the cuff ring prevented me from being able to remove it. Seeing that there was no way I could pull it off, I started to try and extract my limp pen-is but I couldn’t get a hold of enough of it to get it out.
“Oh, I wouldn’t bother trying that, Joshy,” Aunt Emily advised me, “These are quite escape proof, even for young boys with little pen-ises like yours.”
“B-but—ho-how will I be able to pee?” I asked quizzically.
Red flags and alarm bells were going off in my head as I began to understand just what this would mean.
“Don’t worry about that—that’s why there’s a slot at the bottom of the tube, to allow you to pee without removing the device. However, you’ll probably find that you’ll have to sit down like a girl to use the toilet now, due to the angle of the wee-wee tube—that is, until we make other arrangements,” she giggled.
I was still too shocked to pick up on my aunt’s enigmatic reference as I pondered what it would be like being unable to stroke my coc-k anymore.
“B-but how long…how long will I have to wear this?” I asked nervously.
“Oh, I think until you’re about 18 should be okay. Then we can think about whether to let you out or leave it on longer.”
I didn’t know what to say and I stared at her with my mouth open as she calmly gathered the items on the ground together and stood up to take them inside. The idea of doing without masturbation was beyond imagining for me and I knew right then and there I’d have to find some way to defeat this devilish device. It would be my quest and I promised myself I wouldn’t stop until I had figured a way out of the implacable contraption.
-
So now Auntie has little Josh locked!
I’m sure it’s only a matter of time before he starts having to take 'vitamins' and wear a little plug.
Such a loving Auntie knows what’s best for boys…
-
I never realized just how much I’d been masturbating until the option was forever taken away from me by Aunt Emily. She was right that I could continue to go pee without any difficulty but I was no longer able to touch my pen-is in any way and it was driving me crazy. Nor could I manipulate the tube to try and induce enough friction to achieve an orgasm. At best, all I could do was to get myself excited which only made me more frustrated.
My situation was made worse by my aunt who thought nothing of walking around the house in her skimpy clothes. Now that summer was in full swing and the temperatures were getting hotter, she’d often be doing her housework in nothing but a short pair of shorts and her tiny bikini top. I’d gaze at her in utter frustration, going out of my mind with lust as I stared at her mouthwatering curves. She seemed to be totally oblivious of my situation and she’d think nothing of standing there, her big boobs staring me in the face as she explained some detail or another about a subject that I wasn’t listening to. My little peanut strained miserably in its hard plastic prison, unable to attain an erection which by now, was more often than not in my pretty panties. Only thing was, I could no longer feel the soft fabric caressing my pen-is anymore. I could still feel it rub and stroke my balls but that only added to my sense of frustration.
Countless times, I tried rubbing my balls, hoping it would cause me to c-um but I only succeeded in getting myself even more worked up than before with nothing to show for it. After several days of this, I was sure I wouldn’t be able to take it for another week but I had no idea how I could approach Aunt Emily to take it off. It was obvious she didn’t want me playing with myself and I knew she’d never agree to remove the chastity device simply to let me relieve my ever present horniness.
I tried desperately to think of something else and sometimes that would work for a while, but Aunt Emily would always foil my efforts in the end. For instance, I might be sitting on the floor of my bedroom playing with my toys when she’d come in and bend over to talk to me. Her massive breasts would hang there, barely contained in her skin tight top, tempting me with their fantastic size and shape and my little pen-is would expand painfully in its prison until I groaned with discomfort. I found myself worshiping her and hating her at the same time. I was so confused!
One day, a week later, I couldn’t find one of my shoes and I searched everywhere in vain, unable to locate it. I had no idea how I could have lost it but after looking all over the house, I finally gave up and went to tell Aunt Emily. I found her, sitting in her bedroom on the bed and going over some bills. She was wearing a short skirt and a wrap around top that revealed every delicious curve of her huge, round breasts. I gulped and swallowed hard as my peanut began its inevitable rise to futility.
“A-Aunt Emily?” I asked hesitantly.
Oblivious of my lustful frustration, she looked up from her work and beamed warmly at me.
“What is it, Sweety?” she asked pleasantly.
The light of her bedroom lamp was shining off the soft plump skin at the top of her exposed bosom, making my mouth suddenly dry.
“Um, I-I can’t find one of my shoes,” I said, trying to will myself, not to be distracted by her fabulous body.
“Don’t you have another pair, Joshy?” she asked, although something told me she already knew the answer.
“No, I only had the one pair when I got here,” I explained.
Aunt Emily nodded her pretty head and looked thoughtfully at me for a moment.
“I think I have something you can wear,” she said suddenly.
Going to her large walk-in closet, she bent down, giving me an outstanding view of her firm, pert behind. I could see every outline of her sexy panties as they hugged her perfect derriere. When she stood back up, she was holding a pair of white girl’s Ked’s shoes.
“I think these might fit you,” she offered.
They looked very sissyish to me and I was reluctant to accept them but I didn’t know what choice I had.
“Don’t you have anything else?” I complained.
“I’m sorry Sweety, but I don’t,” she replied sympathetically.
I sighed and put the shoes on but I felt like a little girl wearing such prissy footwear.
“They make me look like a sissy,” I whined.
“Aww, now don’t you worry, Honey,” she said trying to console me, “No one will see you and anyways, I think they look just fine.”
I wasn’t convinced but I didn’t see what else to do.
“Okay,” I said, although I wasn’t too happy about the situation, “but can we get some new shoes for me soon?”
“We’ll see,” she said as she returned to her bills although I’d learned by now that that response pretty much meant no to whatever I was asking for.
Looking one more time at my reflection in the mirror, I was struck by how much I looked like a little girl. My hair was growing longer and with my exposed pink panties and white Ked’s, I was really starting to look just like a little schoolgirl. I blushed and hurried out of her bedroom to escape my embarrassing image.
-
A week later, Aunt Emily succeeded once more in convincing me to dress up in a sissy outfit that had me cringing uncomfortably with embarrassment. I was wearing my sheer yellow panties again, but this time she wanted me to try out a lacy white top with pink accents. She said it meant a lot to her to see me wearing it because it used to belong to a niece she hadn’t seen for ten years. I was a little surprised by that because it looked to me like it was brand new. However, she insisted I was mistaken and she explained its condition by saying it had been carefully stored over the years.
In any event, the short, puffy sleeves and Peter Pan bib-type collar gave it a decidedly infantile, girlish look, and it only came down to just cover my navel. On the chest was an applique of a pink bunny surrounded by building blocks with letters on them. There was plenty of eyelet lace around the edges of the garment, including the frilly hem that I kept trying in vain to pull down. Aunt Emily just giggled and playfully squeezed my buns through the thin fabric of my panties making me feel like a total sissy.
She also told me she had some special socks she wanted me to try, saying that I was “just going to love them”. They turned out to be delicate white anklets with three rows of yellow lace circ-umnavigating their short tops. Over those, she added my now compulsory white Ked’s sneakers which completed my look, or least, I thought it did until she took me into her bedroom to sit me at her vanity.
“I’m going to make you look very special today, Joshy,” she said excitedly as she began brushing my longish hair into two pigtails. She placed a big pink floppy bow on each side and then bent down behind me to share my reflection in the mirror.
“You really do look so sweet, Joshy,” she cooed.
I was squirming uncomfortably, not the least of which was because Aunt Emily was displaying a lot of cleavage due to the plunging scoop-necked top she was wearing. I could see a lot of soft skin and the twin mounds of her bosom was driving me crazy, as usual.
Suddenly, seemingly as an afterthought, she reached over and picked up her perfume bottle. Before I could react, she sprayed me several times with it, giggling with amusement at my discomfort.
“Hey!” I cried out.
Now, I smelled as girly as I looked and I looked very girly!
“That’s a little thing called Little Missy,” she giggled.
“I don’t want to do this anymore,” I whined in an upset tone.
“Wait Joshy—I bought you a little gift,” she said as she turned around to get something. Spinning back around, she handed me a glittery pink purse with Hannah Montana and several stars adorning its sides. It looked like it was made for a five year-old girl to put her faux make-up in and I had no idea what she wanted me to do with it. I stared back at her sheepishly but she beamed down at me like it was a gift I’d been waiting all my life for.
“It’s just for today, Joshy,” she explained, “I just thought it would go really cute with your outfit.”
“But I don’t wanna dress like a girl,” I complained.
“Oh, but you make just the cutest little thing, Joshy,” she gushed enthusiastically. She placed the purse on my arm and then stood me up, squeezing my bottom affectionately which only made my pen-is try and get hard all over again.
I was very confused, having various different conflicting feelings coursing through me at the same time. On one hand, I was tremendously embarrassed by my sissyish outfit and wanted nothing better than to rip them off. On the other hand, being in such close proximity to my aunt was also making me incredibly horny, a fact that was exacerbated by the fact I hadn’t been able to masturbate for over a week.
I guess there was no harm in playing along with her, I reasoned, considering how important it seemed to be to her. And truth be told, I was completely powerless to deny her anything when she smiled at me like she was doing now. My heart would always skip a beat and I somehow forgot for the moment that I looked just like a girl out of kindergarten.
Obviously pleased that she had convinced me, she informed me it was lunch time and that we would be enjoying it outside on the patio, since the sun was out and warm. As usual, I was a little nervous about going outside like this, but then, I remembered last time we were outside and everything had turned out fine.
We headed out of the bedroom together but then my aunt stopped me in the living room.
“Can you skip, Joshy?” she asked me suddenly.
“Huh?” I asked, momentarily confused.
“Sure—you know, skip along like this--”
Aunt Emily demonstrated for me what she had in mind, skipping her way toward the sliding glass door, before turning to face me. For some reason, she looked so utterly hot—looking as if she were nothing but a happy little girl--and her ravishing face was devastatingly beautiful.
Oh well, I guess I could play that game too.
Swinging my arms, I skipped along quite gaily, as if I didn’t have a care in the world. Aunt Emily opened the door for me and I skipped right out and onto the patio—where I stared open-mouthed at four of her girlfriends sitting around the pool table!
They turned as one to face me and they burst into smiles and then open laughter. In an instant, my face blushed beet red as I stopped dead in my tracks at this unexpected audience.
“Hi Joshy!” one of them cried in a delighted voice.
“Come here, little Sweety!” called another.
I took a step backward in a panic and nearly wet myself as I tried to deal with the magnitude of my humiliation, but I backed right into Aunt Emily.
“Its okay, Joshy, these are just a few of my friends,” she told me, as if nothing were out of the ordinary.
“This is Lauren, Vanessa, Jessica, and Jennifer,” she said as she gestured to each one of her cute friends.
Despite my smoldering shame, I could acknowledge--if only to myself--that Aunt Emily’s friends were hot in every sense. All of them were good looking, slim, and in great shape, wearing clothes that showed off their fabulous bodies to good effect.
I could see that Jennifer was wearing a snug workout outfit that clung to her firm body and she struck me as very athletic. The two in the middle, Vanessa and Jessica, were wearing shorts and halters but their friend Lauren was the one who really caught my eye. She was wearing thin white shorts that hugged her sexy hips and a flimsy see-thru cover up that did nothing to hide her incredible bosom. I could plainly see her big, bountiful breasts, barely restrained by a neon yellow bikini top that pushed them up and together into a glorious display of erotic female curvature. She was definitely all woman, and her intent stare at me only made me feel like more of an effeminate sissy.
“Come here, Joshy, and sit on my lap,” she beckoned to me.
I bite my lip in angst as I stared back at the four of them.
“Go ahead Joshy,” my aunt encouraged me, “she won’t bite.”
“I don’t know…” Lauren added with a giggle, “This little sweetie looks good enough to eat!”
My face was blazing like a five alarm fire as these babes enjoyed teasing me about my state of dress.
“What a cute purse you have, Joshy,” Jessica said in a condescending voice, “Is that where you put your make-up, Sissykins?”
I shook my head no as the blood sang in my ears.
“What on earth is that you’ve got in your panties?” Vanessa asked abruptly as she pointed at my crotch.
My CB-6000S could be easily seen through the sheer yellow fabric of my panties and I suddenly tried to cover the embarrassing device with both my hands.
However, Aunt Emily gently pulled my hands behind me and prompted me to walk closer so everyone could get a closer look. Holding my hands together with one of hers, she used her free hand to pull my panties down in front, showing the fascinated women exactly what it was I was wearing.
“Joshy’s been starting to get erections, I’m afraid to say. But I wasn’t too concerned about it until the other day, when he had a little, um—accident, in his panties,” she explained patiently.
“Accident?” Jessica asked puzzled.
“Mm-hm…Joshy, would you like to explain it to the ladies?” my aunt asked me in a soft voice.
My ears and chest reddened to match the crimson color of my face but I shook my head adamantly.
“Well…the poor little thing seems to be a premature ejaculator and he simply lost control, making a nasty mess in his panties--isn’t that right Joshy?” she said, patting me sympathetically on the head.
It sounded to me like she were describing a four year-old, not a budding teenager.
“Sounds like this little sissy needs to be put back into diapers,” Vanessa observed disdainfully.
“Oh, he wil--” my aunt stopped herself in mid-sentence and let out a giggle that seemed to be covering up for her slip of the tongue, “I mean, we’ve got that all taken care of now—haven’t we Joshy?”
-
Lovely story, Josh is such a lucky sissy. Thank you
-
Unable to reach physical satisfaction, Josh’s is left involuntarily in a state of perpetual desire; a state that will overpower his superego and thereby will facilitate his acceptance of the realization of his deepest desires, desires that were manifest by his enjoyment of doll-play many years earlier with his aunt who correctly read the essential deeply feminine and infantile nature of her nephew (which is also why his father threw a fit about that play). Joshy is indeed totally lucky and will be unable to resist his feminization and impending infantilization. Please continue this most satisfying tale.
-
I like to think that the Vanessa who said Josh should be put back in diapers is the same Vanessa from "Jimmy's Return to Diapers", like Bobby's work is one big gigantic "Sissy Literature Universe" like the MCU.
Nice work as always.
-
Bending down to look me in the face from the side, my aunt was prompting me to agree with her but I couldn’t take anymore of this kind of attention. I abruptly wrenched my hands free and stormed off into the house, determined to tear up all the embarrassing sissy clothes I was wearing. Going through the living room, I threw the pink purse on the couch and ran into my bedroom, slamming the door behind me in an angry huff.
My face was still burning with shame and when I noticed my reflection in the full length mirror in my room, I nearly burst into tears. How would I ever live this down? How had I gotten myself into such a humiliating situation?
Looking at myself, I looked like a five year-old girl about to cry her little eyes out. My lower lip trembled and I fought the urge with all my twelve tears of experience, even as my vision became blurry with tears.
I was just about to strip off my top when the door suddenly opened and Aunt Emily’s friend Lauren strode into the room like she owned it. I was a little intimidated by her since she was much taller than I was and obviously, a lot older. For some reason, her big breasts also added to her very adult persona and I hesitated uncertainly before her.
She beamed down at me and shook her pretty head sympathetically.
“There-there,” she said as she swept over and hugged me to her soft, cushiony chest, “no one meant to hurt you Baby.”
I wanted to speak but a tear trickled down my cheek and my throat was choked with emotion.
“I-I was so--” I sobbed as my shoulders shook uncontrollably.
She stroked my head affectionately as I nuzzled blissfully against her exciting bosom.
Slowly, Lauren led me gently over to the bed where she sat down on it, taking me carefully and positioning me up onto her lap.
“Hey…shhh,” she whispered in a warm, consoling voice, “there, there…don’t cry, Joshy.”
Even though she seemed to mean well, her words and childish treatment of me only made me feel even more like a baby and another set of tears tumbled down my face before I could stop them. I was tired of people treating me like a girl and a sissy and no one wanted to give me the respect of the young man that I knew I was.
“Don’t be so sad, Joshy…” she comforted me, “You’re a cute little boy, you know.”
I sniffled and felt a least a little better about that remark. I liked the idea of her thinking of me as cute although I took issue with the ‘little boy’ part. I was almost a teenager, for crying out loud!
“How about if I gave you a little kiss—hmm?” she offered in a sweet voice.
I looked at her uncertainly, my face wet with tears as I sat in her lap like a child. She was very pretty and her full, luscious lips shined with a glossy, wine colored lipstick. Without a doubt, she was drop-dead gorgeous and I wasn’t about to turn her down.
Without waiting for an answer, she leaned forward and, closing her eyes briefly, kissing me gently on the lips.
Wow!! I couldn’t believe it! My first kiss and it was with a real knock-out!
My head was spinning and I felt that familiar pain starting to grow in my crotch as my wiener struggled to grow harder.
“You know,” she began, “you missed out on a nice lunch your aunt had planned for everyone. But don’t you worry, I’ve got something even better that I think you’ll like,” she said eagerly in that soft, conspiratorial voice of hers.
I was still staring at her enticing lips when she began stroking the plump mounds of her big breasts, caressing them with her sexy manicured hands. This was really something for me to watch and my heart skipped a beat as it raced into full speed ahead.
She slid me off her lap and then onto the bed face up so that I was now positioned directly in front of her massive bosom which was tightly stretching the fabric of her bikini top in the most erotic way.
“It just so happens that I’m lactating so I can promise you a nice full meal, Joshy,” she said, her voice getting thick with desire.
I was starting to get an idea where this was heading and suddenly I grew nervous, feeling like I was in over my head. At my age, I liked the idea of kissing girls and maybe an experimental fondle here and there, but I was totally unprepared for anything more. I swallowed hard as Lauren slowly unclipped the front of her straining bikini, releasing her huge melons from their smooth cups. I stared dumbfounded as she cupped the left one and brought it forward to position it before my face. I’d never seen a woman’s nipple in my life and here was one right in front of my face! It stuck out, about the thickness of my finger and I saw the tiny hole in which liquid was already seeping out.
“N-no, please--” I stammered, “I-I’m-not sure I--”
“Shhhhh,” she shushed me, “this is just what my little baby needs.”
“Uh-uh,” I bleated and I shook my head no, trying to dissuade her but she only smiled down at me undaunted. Taking her big firm nipple between her slim finger and thumb, she gently squeezed it and I watched in awe as a small dribble of breast milk leaked out.
“Open up, Sissykins,” she insisted with a big smile.
I struggled on her lap but she put her other hand behind my head and forced me to face her gigantic breast.
“No—p-please!” I whined pathetically but she only smiled and brought my head up to meet her nipple. I felt my lips brush against it and she rubbed it across from side to side, working it slowly inside.
“Take it in, baby Joshy,” she whispered softly.
With a sob of defeat, my mouth opened and her big nipple quickly filled my mouth. Instinctively, I began submissively nursing and I was quickly rewarded with a steady stream of warm, odd tasting milk.
“That’s a good boy…that’s my little baby,” she cooed softly to me.
I whimpered helplessly as I suc-ked like an infant from her tremendous, milk laden breast, feeling more babyish than ever.
Lauren’s hand shifted to pat my panty clad bottom in a soft, maternal gesture.
“You know, Vanessa was right,” she said, practically in a whisper, “I think you do belong in diapers and plastic panties.”
I tried to shake my head in disagreement but Lauren wouldn’t allow it.
“You just keep nursing, Baby,” she told me, “I’ll tell you when you’ve finished.”
Not wanting to cross her, I did as I was told, closing my eyes as I suc-ked mouthful after mouthful of warm breast milk. I was so absorbed by what I was doing that I failed to notice when Aunt Emily came into the room, unannounced.
“I think your baby here is going to need to be put into diapers before you lay him down for his nap,” Lauren said with a big smile.
I opened my eyes to see my aunt gazing down at me, my mouth full of Lauren’s plump boob, suc-king like a newborn infant.
“Well, if I had known my little sissy was a breast feeder, I would have put him into diapers a long time ago,” Aunt Emily remarked.
I mewled in protest but Lauren was making sure I couldn’t pull away from her massive breast.
“I came in here and the poor little sissy was crying his eyes out,” Lauren explained, “The only way I could get him to stop blubbering was to offer him some mother’s milk, straight from the source.”
“Is that so?” Aunt Emily mused.
“Oh yes, he really is a needy little child, but giving him a nipple to nurse from seemed to calm him down right away—isn’t that right, Sugarplum,” she said in a mocking voice used with toddlers.
I tried to shake my head no but Lauren was gripping my neck firmly from behind and I squealed ineffectually with my mouth full.
“Joshy, why didn’t you tell me you were still breast feeding? Were you too embarrassed?” Aunt Emily asked innocently.
I tried to speak to counter Lauren’s lies but I was hopelessly gagged.
“Don’t you worry, Honey, we’ll take care of all your little baby needs,” she said confidently, “From now on, you’ll be my little sweet toddler, and I’ll make sure you get all the breast milk you can handle. Fortunately for you, I’ve also got plenty of diapers and baby clothes that I know you’ll absolutely adore!”
Suddenly, I felt like I was falling slowly down a mine shaft, unable to stop my fall. Somehow, I knew intuitively that my aunt had plans to take my emasculation process further by treating me like a baby and I knew I had to stop her, and stop her right now!
I jerked my head away from Lauren’s breast and stumbled up awkwardly from the bed.
“No!” I shouted, “I’m not going to wear diapers and baby clothes!”
My aunt looked mildly surprised but not shocked as she crossed her slim arms over her big breasts.
“I’m tired of being treated like a girl and a sissy!” I continued my tirade, “From now on, I’m going to wear what I want to wear.”
For a moment, a tense silence filled the room with none of us speaking.
“All finished?” Aunt Emily asked curtly, an icy tone putting an edge to her voice, “Are you done with your little temper tantrum?”
Still simmering, I nodded sulkily but I looked away, unsure of just what I’d done.
“Good, because you’re coming with me, Little Boy,” she said and she reached down to snatch my wrist.
“Wha-where are we g-going?” I asked as she jerked me out unceremoniously into the hallway and down toward the bedrooms.
“I know you’ve just been dying to see what’s behind this door so now you’re going to find out,” she replied, her voice filled with determination, “Oh yes, you’ve had this coming and now you’re going to get it in spades.”
I pouted and whimpered as she opened the forbidden pink door and pulled me inside. As she flipped on the light, I saw a baby’s nursery that looked like it had been decorated for a toddler girl. Pink and white wallpaper patterned with playing animals covered the walls and a large crib dominated the room. Frilly pink curtains softened the sunlight coming into the room and a dresser, also in pink, stood next to the crib. On the floor was a low changing table, its padded surface covered with nursery print vinyl plastic and next to it were tall stacks of thick cloth diapers.
My stomach buzzed nervously as I took all this in but I didn’t have time to absorb it all before I saw Aunt Emily reach for a stout wooden paddle much like the one in the kitchen.
“I-I I didn’t mean to--” I babbled nonsensically.
I gulped in fear as she lowered the crib bars on one side and took a seat on the waterproof sheeted mattress.
“Its time for you to learn a little lesson in manners,” she said evenly as she pulled me over to her side. Wearing only my panties and the sissy top, I felt naked and defenseless as I trembled before her.
“No-no--” I stammered weakly as she wrestled me over her bare lap.
I fell face forward and found myself staring at a diapered yellow teddy bear on the floor in front of me.
“Wait! Please! I’ll be good—honest!” I pleaded.
Aunt Emily moved her high-heeled feet slightly apart and rubbed the smooth paddle against my pantied bottom as I whimpered fearfully.
“Its time you learned who makes the rules in this house, Young Man,” she lectured me, “You need to learn that I know what’s best for you and if that means putting you back in diapers, that’s what’s going to happen.”
“P-please Aunt Emily, please don’t sp-spank me,” I wailed piteously.
Ignoring my whining, she raised the paddle high up over her head and then brought it swooping down, to land with a deafening SMACK!! across both of my unprotected cheeks. I howled out and kicked my feet, just in time for her to grip my torso to hold me securely in place and prevent my escape.
“We both know you’re a little sissy who belongs in diapers and plastic pants and that’s just what you’ll wear from now on.”
SMAAACK!!!
The paddle seared itself with a terrifying impact, flattening my round, youthful cheeks with impunity before they bounced back up in place, ready for another blistering swat. I immediately burst into tears, acutely aware that the door was open and everyone outside would be able to hear me. Here I was, a twelve year-old guy, being given a spanking over my aunt’s lap like an errant child and told that I’d have to wear diapers from now on. It was mortifying!
“You may have thought you were coming here to be able to wear panties but clearly, diapers are more appropriate for you.”
She delivered two stinging, punishing swats to each cheek.
SMACK!! SMACK!! SMACK!! SMACK!!
“You’ll wear what I tell you and do it without question—do I make myself clear?”
Before I could reply, the hard wooden paddle came swooping down again, slapping my frilly pantied cheeks with angry, fierce determination.
Suddenly, I felt her long fingernail reach inside the waistband of my prissy undies and jerk them downwards, to frame my soft, bare buns for more of her harsh discipline.
I was sobbing like a baby as the paddle rained down again and again, slapping my exposed bottom with a terrible vengeance. I kicked frantically and pounded my bunched fists on the floor, wailing at the top of my lungs in anguish.
Being made of hard oak, the wooden paddle was uncompromising as it blistered my tender, round cheeks mercilessly. The hard, crisp swats filled the room like thunderclaps, mixed with the continuous sound of my crying unashamedly. There could be no mistaking the sound of a naughty little boy getting his bottom spanked, and spanked hard.
Lauren was avidly watching my punishment closely and a small smile had formed on her cute face, showing her obvious satisfaction at what was taking place. Occasionally, she’d nod in agreement as a particularly harsh slap caused me to buck and cry out louder.
I couldn’t believe how hard my aunt could spank and if her arm was tiring, she certainly didn’t show it. She was determined to teach me a lesson and my bottom was getting its full measure and then some.
At long last, my aunt stopped spanking me and she began rubbing my blazing, throbbing cheeks again with her paddle.
“Is baby Joshy ready to be put into his diapers?” she asked innocently.
I was too busy blubbering to make a coherent reply so I nodded my head and said the closest thing I could articulate to a yes.
SMACK!!!
“I didn’t hear you Joshy…are you ready to be a good little baby now?”
I cried out in pain and anguish, another set of fresh tears spilling down my face.
“Y-y-yes Ma’am!” I cried miserably.
“Good. That’s mommy’s little baby,” she said, apparently satisfied.
Setting the dreaded paddle on the crib mattress next to her, she reached down and helped me to stand, although I was a total wreck and I wavered before her on unsteady feet. I was too ashamed to look at her directly and I stared at the floor instead, crying openly like a little child. Being disciplined by my beautiful aunt was more than I could stand and I was mortified beyond belief. All my dreams and aspirations of being considered as an equal had gone up in a poof of smoke. All along, I had been fooling myself, believing that I was an adult on par with her. She had clearly established her absolute authority in the house and I felt chastened and defeated.
Aunt Emily took me in her arms and began patting me on the back, saying soft, soothing things in my ear.
“There, there Baby…it’s all over now,” she told me in her usual sultry voice, “Your spanking’s finished and everything’s going to be okay Sweety.”
I sobbed uncontrollably and my tears fell from my cheek to drop down onto her bare back.
“There, there Joshy,” she said cradling my head, “Shushhh….shush now. Mommy’s going to make everything all better.”
I wasn’t sure what to make of her assurances but I certainly wanted to be in her good graces again. I hugged her tightly and I could feel her big soft breasts pressing against my own chest. She waited a little while longer for my sobbing to subside before she began again.
“Joshy? Mommy needs to put you into your diapers now…but don’t worry Honey—I’ll make sure you have the cutest plastic panties on so you don’t have to be concerned about that—okay?”
Her voice was one of soothing comfort and I felt a strong sense of protection from her, like she was going to protect me from the rest of the world.
Gently, she pulled me away from her embrace and stood me before her, using her finger under my chin to make me look her in the eyes. Tears were still spilling down my cheeks and I had to wipe the goo dribbling from my nose.
“Joshy, I know you think you’re a big boy now but I’m a lot older and wiser than you are and I know you’re just not ready for big boy underwear yet. Maybe someday—but not yet. You need the safety and security of a nice thick diaper and waterproof panties. You can trust me because I love you—you know that don’t you? I love you very much and I know this is what’s best for you.”
I was ashamed to hear these words from my aunt--words that said I was nothing but a baby—and it only made me want to cry harder. Ironically, I also knew my crying was making me look even more childish but I couldn’t stop myself. Looking at her mature, pretty face, I knew she held all the cards and that I was a helpless pawn for her plans. Our relationship had undergone a huge and irrevocable power shift--she was in charge now and I had no choice but to follow her directions.
-
Bobby, Bobby, Bobby great addition, but he didn't finish his nursing! Although I can't help feeling it might become a regular thing.
Now he's agreed to go back into nappies, he won't need his CB chastity device will he. I mean all his spurties will be soaked up in cotton towelling. Surely a bit of quid pro quo would be allowable?
Keep it up BB, looking forward to where this is going.
Ace
-
“Now…I know this is going to be hard for you, but the first step for you to take is to admit that you’re a sissy. It’ll make things go much easier from here on if you do. Understand Joshy? You and I both know it, but I think it would be best if you were to say it out loud.
“Can you do that for me Honey?” she asked in her sweetest voice.
My face was beet red and it was impossible for me to say the humiliating words, especially with Lauren standing right there, so instead, I just nodded my head.
“Go ahead, Joshy—tell us what you are,” her friend prompted me.
My bottom felt like someone was holding a red hot skillet to it and I was more than terrified of going back over Aunt Emily’s lap.
“I-I’m a s-sissy,” I mumbled, barely audible.
“You can do better than that, Joshy,” Aunt Emily chided me good-naturedly.
I cleared my throat.
“I’m a-a sissy,” I said with more authority and certainty.
“That’s better baby,” she said, obviously happier with my performance, “And now it’s time to put you into your new underwear. As you can see, I’ve got stacks and stacks of soft, cuddly diapers for you to wear and wet, and plenty of cute plastic panties in all sorts of colors. They’re just what every sissy needs to keep himself protected. And don’t worry Baby, before long--you won’t even notice you’re wearing them.
“So--we have a few new rules now--from now on, I want you to ask me to change you when you’re wet but since this is your first time, you can just ask to be put into your diapers—okay Joshy?”
My cheeks were buzzing with shame as I looked furtively at Lauren, hoping maybe she was making ready to leave. Unfortunately, she was still keenly interested in my situation and she was only too happy to see me humiliate myself.
“Go ahead, Honey, ask for your di-dees,” she said to me encouragingly.
Swallowing hard, I fidgeted nervously, shuffling my feet as I stalled. I didn’t want to be humiliated with wearing diapers but my bottom was burning like a furnace.
Aunt Emily reached down and brought my face back up to look her in the eyes again.
“Joshy?”
I cleared my throat again nervously.
“Will you p-please put me in my d-diapers, Aunt Emily?” I stammered, blushing furiously. I had never been so ashamed in my entire life.
Her pretty face broke into a ravishing grin.
“Well since you asked so nicely, how could I refuse such a request?
“Oh, and one more thing--I want you to start calling me ‘Mommy’ from now on, because I’m going to be your mommy from here on. No more ‘Aunt Emily’—its ‘Mommy’ for my little Diaperkins, okay?”
I blushed hotly and nodded my head in shameful agreement.
She led me over to the changing table and set me down on it carefully although despite the cool vinyl surface, it hurt terribly on my scorched, blazing backside. I let out a cry of pain and unsuccessfully fought back a pair of tears that trickled down my face.
“Poor little baby,” Aunt Emily said sympathetically, “I’ll rub some diaper rash ointment on your warm little fanny.”
True to her word, she squeezed a large handful of the creamy substance into the palm of her hand and began applying it across my hot, stinging cheeks. With one hand, she held my ankles up high, exposing my bright red bottom to Lauren as she slowly rubbed the soothing crème into my skin. I whimpered with pain and humiliation as she finished her task and then slid three thick diapers under my raised rump. With a deft movement, she tugged my yellow panties down my legs and threw them into the trash without a word. I was devastated to think that I’d never wear soft, silky panties again and I fought against the tears that threatened to spill down my cheeks anew.
Laying me down gently, she picked up the baby powder and began shaking it generously over my crotch and belly. Taking her time, she rubbed the sweetly scented powder all over, from my chest all the way down to between my legs. The familiar scent brought surprisingly strong memories of babyhood flooding back and I balled my fists in mute frustration. Softly rubbing the silky powder into my swollen, c-um-filled balls, she seemed to take an especially long amount of time and looking up at her big boobs barely contained in her top, my pen-is throbbed in futile frustration within its hard plastic prison.
I squirmed in silence as she hummed a pleasant tune and finally pulled the soft, bulky cloth up between my legs, pinning either side around my hips with pink bunny-headed safety pins.
“That’s my little baby,” she said encouragingly as she beeped my wet nose.
My only consolation was that I hoped my new attire would remain a secret between these two women—I sure didn’t want anyone else finding about what had happened.
“Now—let’s pick out an extra special pair of plastic panties for our little princess,” she said gaily.
Opening up the dresser drawer, she sifted through stacks of neatly arranged plastic pants until she pulled out a white pair with pink polka dots. I saw that they had lilac lace around the legs with a single fancy bow on the waistband.
“Here you are, Joshy!” she exclaimed, “I think these will be just perfect for your first day in diapers.”
She made it sound like a momentous occasion like I were heading off to grad school or something. Instead, she was putting the final touch on my transition to babyhood.
I cringed as she gathered the leg openings and began snaking them up over my ankles.
“These will make sure you don’t have any ‘accidents’ or wet the furniture,” she assured me with confidence.
I gulped as she pulled the noisy panties up my smooth legs and began working them over the embarrassing, fat diaper I was wearing. Tugging and using her fingernails, she worked the panties up and around, making sure she got a perfect fit around my hips and thighs.
“There!” she said happily, “You’re all diapered and ready for your nap!”
I really didn’t want to take a nap but I sure didn’t want to end up over her lap again. I whimpered and pouted, showing my displeasure not unlike many a toddler being sent to bed for his daily nap.
“Aww, mommy’s baby wants to stay up, does he?” she asked with mock concern, “Here you go Joshy, maybe this will make you feel better.”
She took a large pink rubber pacifier and pushed it against my lips, forcing it inside until I found myself passively suc-king on it. I felt so utterly babyish as I looked down at the shiny white and pink vinyl panties surrounding my bulging diapers while I suc-ked helplessly on the rubber nipple filling my mouth.
“We just need a comfy sleeper outfit for you and you’ll be all ready for your crib,” she informed me.
Walking over to the closet, my aunt sorted through the various dresses and rompers until she found a soft, fuzzy Care Bears onesie, with ruffled sleeves and leg openings. Bringing it over, she helped me out of my sissy top and slipped the plush, cozy garment over my head. She pulled the stretchy fabric down over my chest and I noticed there was some sort of elastic in the waist that hugged me, yet allowed for freedom of movement and comfort. The bottom half was cut large enough to allow for a big, thirsty diaper, even one as over sized as mine was. Aunt Emily continued humming to herself as she drew the front and back sections together between my legs and secured the four snaps shut.
Even though it fit me remarkably well, I could still see glimpses of my shiny plastic panties underneath at the leg holes and the elastic waist ensured my bell shape would be unmistakable to anyone seeing me. It was obvious there would be no doubt that I was very well diapered underneath this babyish outfit.
“Stand up Joshy, so we can take a look at you,” Aunt Emily said enthusiastically.
With great reluctance, I got to my feet and soon realized I couldn’t stand in my normal fashion due to the thick, but soft bulk between my legs.
“Oh my!” Aunt Emily exclaimed as she put her slim hand in front of her mouth, “Aren’t you just the cutest thing in the world!”
I blushed anew and realized the rest of my look coincided perfectly with the onesie and diapers. My hair was still in pigtails, held up by the pink bow and my Keds with the white anklets added further to my babyish appearance.
“Come along now Joshy,” she said as she patted my fat diapered bottom, “Let’s go say goodbye to your guests and then its beddie-bye time for you.”
I shook my head anxiously and muffled a protest but the pacifier in my mouth prevented me from speaking clearly.
“Here you go Joshy—and here’s a cuddly teddy bear for my little princess to hold onto,” she said, placing the diapered bear in my arms like it was perfectly normal.
I pouted and sulked as she led me out of the nursery and back outside again where my aunt’s friends were talking amongst themselves. It was a strange and unfamiliar feeling as I waddled behind my aunt, the thick diaper rubbing softly between my thighs.
As we came out before her friends, my face and chest flashed crimson all over again as the women turned to face me in my most recent ensemble.
“Well, that’s quite an improvement,” Vanessa remarked dryly, “I see you put your sissy back into his diapers again.”
-
As usual, wonderful story. Looking forward to next chapter.
-
I resented her remark, if for no other reason than it implied I had been in diapers recently before today but it was their giggles and laughter that really burned me up.
“Yes, it’s been long overdue, but Joshy will be spending his days and nights diapered and dressed like a proper baby girl from now on. We got off to a bit of a rough start, but after putting him over my lap, we got things squared away in no time, didn’t we Joshy?”
The girls laughed in amusement and I felt my eyes brimming with tears of humiliation. I could tell by the looks on their faces that they’d heard every slap of Aunt Emily’s paddle on my bottom, not to mention, my bawling like a baby.
“Apparently,” Lauren told them, “Joshy here hasn’t been properly weaned because the only way I could quiet him down was to breastfeed him like a little baby.”
Hot waves of shame rolled over me as they looked at me like a childish toddler in need of his mommy.
“Did he actually nurse from you then?” Jessica asked, a little surprised.
“Just like a newborn baby,” Lauren replied, “I could hardly get my nipple out of his mouth without him whimpering and carrying on—it looks like I’ll have to make regular visits here so I can satisfy his need for breast milk.”
The girls shook their heads and stared at me while I wilted with embarrassment.
“Say goodbye to your guests now Joshy, and then it’s off to your crib for the afternoon,” Aunt Emily told me.
I wasn’t sure what to do until my aunt took my hand and made me wave at her gathered friends, a childish gesture that brought forth even more giggles at my expense.
Their laughter followed me and rang in my ears as I trudged back down the hall, Aunt Emily holding my hand as if I were a child.
“I know this has been a big day for you Joshy, but don’t worry—you’ll feel much better after a nice, long nap,” she told me as she led me into the nursery. I was still on the verge of tears and frustrated that there didn’t seem to be anything I could do to change my circ-umstances. Perhaps I could escape, once she’d let me alone in the crib, I mused.
Pulling back the baby blankets, Aunt Emily patted the smooth, shiny waterproof mattress covering and beckoned me to lie down. Reluctantly, I waddled onto it and she drew the soft, fuzzy baby-blue blanket over my body.
“That’s a good baby,” she commended me as she pulled the side of the crib bars up to snap into place.
She bent over the top, giving me a fabulous view of her massive breasts as she stretched to reach something. However, to my surprise and dismay, I saw that the crib had a locking top that folded with an additional set of bars over the upper rim, making the crib a veritable cage. I was trapped like an animal!
Aunt Emily beamed down on me like a proud mother as she clicked the locking top shut and blew me a kiss.
“Happy sissy dreams, Joshy,” she bade me, “When you wet your diapers—you just call out and I’ll come and change you—okay Sugarplum?”
I couldn’t believe that! There was no way I was going to purposely wet my diapers for her.
Stopping at the door long enough to turn out the lights, Aunt Emily waved me goodbye and then closed the door part way behind her.
There was only a Cinderella night light to provide illumination but the sunlight coming from the single window removed any sense that it was bedtime for me. Somewhere outside, my friends were playing rough and causing trouble while I was locked up in this nursery, diapered like a baby and helpless to do anything about it.
I could vaguely hear the laughter and conversation of Aunt Emily’s friends and I was sure they were enjoying themselves and making smug comments at my expense. My aunt had made very clear who was in charge here and I smoldered with resentment and humiliation. I had let her trick me all along and now I was her obedient child, subject to her every perverse whim. It was infuriating because she was “only” a woman and guys my age were supposed to be tougher than that. No self-respecting guy would let a woman push her around like that. The unfairness of it all burned at me like a hot coal.
It was all the more grating that Aunt Emily and her friends were a group of hot babes, totally untouchable by me. They were sexy and pretty, yet I was denied the satisfaction of even masturbating to their memories! It was too much to bear! And now they knew I had been paddled for misbehavior and put into diapers. What could possibly be worse? Could I possibly sink any lower as a guy?
Reaching down, I could barely feel my privates, so thick were my diapers. It sure didn’t help any that I was still horny as all hell. It had been nine days now since I had last c-um, and I was frantic for some relief. I had tried over and over, but in the end, all my efforts to find a way out of my cursed chastity device had met with abysmal failure. I was becoming resigned to being subject to Aunt Emily’s rigid control over my sexuality, to say nothing of my attire but I still hated it.
I tried to blank out the memories of their mocking laughter and their superior expressions but I just couldn’t. These women would never forget that I had been spanked, breastfed, and dressed like a baby by my aunt, turned into a sissy infant who hadn’t fought back in the slightest. I blushed anew, every time I relived the mortifying experience in my mind.
Finally, after an hour of bored tossing and turning, I fell asleep.
“Hi Joshy,” my aunt whispered at me.
I opened up my eyes to see my aunt’s pretty features glowing happily as she bent over the opened crib to look down at me. Her big breasts were pressed together, looking as if they were going to burst out of her snug white top at any moment. In her slim hand, she held a large baby bottle filled with milk and she was lowering it down towards my face. I could see a drop of milk about to drip from the end of the brown rubber nipple, threatening to spill on my face.
“Time to wake up, Sweety,” she sang as she positioned the warm nipple at my lips.
“Uh-uh,” I protested weakly and I tried to move my head away but Aunt Emily reached down with her free hand and pinched my nose just enough to prevent my movement. I saw little more than her exquisitely manicured long nails as I struggled briefly.
“Open up, Baby,” she smiled and as soon as I opened my mouth for air, she pushed the wet nipple into my mouth.
“That’s a good baby girl,” she cooed, “Drink your ba-ba like a good baby.”
I squealed and felt the warm milk trickling into my mouth, despite my efforts to the contrary. The rubber nipple felt oddly familiar against my tongue and it compounded my feeling of babyishness. Aunt Emily smiled with satisfaction and her other hand reached down to gently squeeze the front of my crotch.
“Did baby wet herself during her nap?” she asked, using a pouty voice reserved for toddlers.
“Uh-uh,” I tried to say but it was muffled as I swallowed another mouthful of warm milk. I hated drinking milk--if for no other reason than I associated it with my infancy and nursing it from a bottle certainly reinforced that feeling in me.
“Good for you,” she congratulated me, although her tone lacked sincerity, “Now you make sure you drink it all down—I don’t allow any wasting in this house.”
Not surprisingly, my bottom was still sore from earlier and I certainly didn’t want to risk another trip over her lap. Since there was no way I could overcome my aunt physically, I reasoned that my best bet lay in cooperating and trying to get back on her good side again. Maybe there was still some hope of convincing her to let me return to my previous status as a young man. To that end, I finished the bottle submissively as she held it and supervised my efforts. While I drank the milk, I also drank in her luscious curves which was hard not to do, considering her big, mouthwatering breasts filled my immediate view. She was wearing a snug halter top with spaghetti straps that clung deliciously to her wonderful bosom.
Suddenly, I found myself ravenously horny. Looking into her pretty, loving eyes and then down to the soft, smooth skin of her twin melons hanging before my face, she was the very picture of sexual motherhood. I wanted desperately to stroke my pen-is for all it was worth and it twitched frantically in my diaper. I felt it grow and it quickly found the limits of my CB, preventing any further growth. Squirming uncomfortably, I nursed passively at the bottle as my wiener fought in futility against its implacable plastic prison. Oh, how I hated that damn thing!
“You’re almost finished Joshy, just the other half to go,” Aunt Emily said, misunderstanding my fidgeting.
I whimpered helplessly at her total control over me, even as I submissively nursed on the baby bottle. Finally, I finished and Aunt Emily pulled the bottle out of my mouth.
“That’s a good baby,” she said happily.
Standing up, she took my hand and helped me out of the crib.
I was still unaccustomed to the feeling of the thick bulk of my diapers between my legs and around my hips, and it reminded me constantly of my infantile status.
“You can play with your toys for another hour while I make dinner—okay Joshy?” she told me.
“Okay,” I replied, although I certainly had no intention of playing with the Barbie dolls or teddy bears scattered throughout the nursery. As my aunt walked out of the room, I suddenly became aware of a strong need to take a pee.
Walking out of the softly lit nursery, I went down the hall to the bathroom, but found the door closed. I knocked curiously but couldn’t hear anyone inside so I tried the knob, only to find it locked. Not believing my own senses, I tried it again but it was, without a doubt, very locked.
I looked around but I knew there was only one way to get in. I went into the kitchen where Aunt Emily was making dinner and stood uncertainly before her.
“Umm, Aunt Emily?--”
“It’s ‘Mommy’ now—remember?” she interrupted as she looked over briefly to see what I wanted.
I cleared my throat to say the unfamiliar term again.
“M-Mommy?” I asked tentatively, “For some reason, the bathroom door seems—um, to be locked…”
“Yes, I know,” she said simply, without looking up from what she was doing.
“But…I can’t get in there to go to the bathroom,” I said insistently.
“Mm-hm, that’s right,” she continued with apparent indifference.
“But how am I going to go pee?” I asked in exasperation, “I hafta go--bad!”
Finally, she turned to face me. Crossing her slim arms over her fabulous chest, she smiled knowingly at me.
“That’s what your diapers are for Sweety-pie,” she told me, “Just relax and let what comes natural happen.”
“But couldn’t I just take my diapers down and go real quick?” I pleaded, trying to win her over with my adolescent logic.
“Its time we set a few rules here, Joshy,” Aunt Emily said firmly as she turned and stood over me, “First off—you must never touch your diapers, only mommy and her adult friends can do that—do you understand me?”
“I-I…” I wasn’t sure what to say and visions of her hot friends pulling my wet diapers down to change me filled me with dread.
“Joshy? Do you understand?” she repeated, “Babies don’t change their own diapers—only adults do.”
I felt like arguing that I was almost an adult but my bottom was still sore from earlier. And I still resented the hell out of being forced into this position of being a diaper dependent toddler but I couldn’t see any way out at the moment.
“O-Okay,” I said without conviction.
“Good. Now the other thing is that you don’t have to go poo-poo in your di-dees. When you feel the need for that, you just call me and I’ll take you in and pull your diapers down for you. Okay, Sweety?”
I blushed at the thought of her taking my diapers down in the bathroom while I stood there helplessly.
“Okay, I guess. But what about now?” I pressed her, “I hafta go pee now—real bad!”
Aunt Emily reached down and took my hand, gently leading me into the living room where she sat us both down at the couch together.
“Sometimes the first time can be kind of difficult,” she said as she looked at me and held my hand in hers. Even through the tension of my angst, I still felt an electric sensation at the feminine softness of her hand and I blushed as I returned her intent gaze.
“It’s okay Joshy,” she said in that sweet voice of hers, “All babies wet their diapers—soon, you won’t even realize you’re doing it.”
“But I’m not a baby,” I protested.
“Have you looked in a mirror anytime recently? You look to me like a sissy toddler girl.”
I blushed deeply, knowing she was exactly right. And for a moment, I forgot about the fact that she had been the architect of my infantile appearance.
“I could tell from the first moment I saw you at my door that you belonged in diapers and baby clothes,” she said, smiling warmly again, “You have such a naturally prissy side to your personality…I’m sure you’ll find your nursery much more to your liking than your old bedroom.”
My face reddened at her assumptions of me and I looked away, at a sudden loss for words. I hated the fact that my beautiful aunt though of me as nothing but a natural sissy who belonged in diapers and dressed as a baby.
At the same time, my bladder was now sending me an urgent appeal to do something about my need.
“Aunt Emily—I gotta go pee!” I complained.
“Go ahead Sissy,” she said patting my hand gently, “Show mommy what a big baby you are.”
I bit my lip and shifted in my seat, trying to will my bladder into submission but I could tell it was a losing battle. The pressure was so great, I reasoned that maybe if I just let out a little, I could contain the rest without humiliating myself in front of Aunt Emily. To my frustration, she was watching me with great patience, in no particular hurry for me to do my business before her.
I relaxed my muscles just for an instant and felt a strong squirt of pee come out. But it was like holding back a breaking dam. I was forced to release another stream and suddenly, it was like the door had been knocked down by a bulldozer. I whimpered weakly as a third, especially strong stream flowed forth, soaking the front of my diaper.
Aunt Emily was watching me knowingly and I could tell she was aware of exactly what was happening.
“That’s my little baby…” she cooed, “Just relax and let it all flow.”
Tears of shame filled my eyes and I sniffed miserably. Now that the front of my diapers were thoroughly soaked, there seemed little point in trying to hold back any further. I relaxed and felt strong streams of warm pee filling my waiting diaper, only to be followed by even more. I couldn’t believe how much I had to go!
Aunt Emily was beaming at me like a proud parent and she reached forward to pat the front of my diaper in a congratulatory fashion.
“The first time is always a little difficult but after that, you’ll find you don’t even have to think about it,” she said happily, “Most sissies are chronic bedwetters anyway so this should come as second nature for you.”
I whimpered helplessly as I shifted in my seat in embarrassment while I continued peeing strongly. I could feel a warm, wet pool of unabsorbed pee surrounding my crotch, waiting to soak into the layers of absorbent cloth and I worried about leaking on the couch.
“A-Aunt Emily--” I started, my voice rising in panic, “I think I-I’m going to leak on the cushions.”
I was about to get up but she held me gently in place.
“Shushh,” she soothed me, “You’re wearing very thick diapers made for a heavy wetter. And your plastic panties are nice and snug so I know they won’t leak. You’ll do just fine, Joshy,” she assured me.
I felt the cloth between my legs soaking up the pee and seeping up into the seat of my diapers, making me feel even more babyish, if that were even possible.
At last, the flow abated and I felt a few residual squirts release the last of my pee before my pen-is finally relaxed.
Aunt Emily seemed to sense what was happening and she asked me to be sure.
“All finished?”
I hung my head in shame and nodded slowly.
“Okay, well I’m going to finish up in the kitchen now,” she said, getting up from the couch.
“Bu-but, don’t you think—I mean—shouldn’t I get a change or something?” I stammered.
“Oh, I don’t think so,” she said with a casual wave of her hand, “I think it’ll be good for you to get used to the feel of wet diapers.
“We’ll have dinner and then I’ll change you before your beddie-bye, okay?”
-
As always Baby Bobby your story is excellent. I wait in eager anticipation for the next part.
-
I couldn’t believe she was going to make me sit through dinner wearing a soaking wet diaper under my onesie. And how early was I going to have to go to bed, anyways? I wanted to argue with her but I bit my tongue instead. She was too tall, too strong, and too quick to pull me over her lap to spank me. I knew I couldn’t take that again.
Instead of answering her directly, I muttered under my breath and went off in a pout. I was angry and frustrated with my situation and I hated being told what to do.
It felt very odd to feel the clammy wet embrace of my diapers as I waddled down the hall and the soft, fuzzy onesie I was wearing only conspired to press the warm cloth closer to my skin. I definitely didn’t like it. Only yesterday, I had had the freedom to wear whatever I wanted and now that had been taken away from me completely.
I trudged into the nursery whose door was now open all the time (if only I’d known what was inside there—I never would have tried to get in!). I saw the same diapered teddy bear on the floor where he’d fallen out of the crib and all my pent-up resentment focused on him. Suddenly, I stepped over and kicked him viciously against the far wall. He hit the wall with a soft thud and then dropped to the floor, looking up at me with his happy, forgiving eyes.
Filled with depression, I sank down to take a seat on the edge of the crib. I could feel the sopping wet cloth clinging miserably to me from all sides now. Trapped by the plastic pants, the moisture had worked its way all around, even up to the upper sides of the diaper.
I felt so babyish sitting in a wet diaper with no way to change my circ-umstances…But wait! Maybe I could change this part of it.
Not four feet from me were two big stacks of cloth diapers and I knew the dresser held plenty of plastic pants. Thinking for a moment, I figured I probably wouldn’t be able to find the exact same kind of panties but that wasn’t important—the important thing was to get out of this wet diaper. Filled with determination, I went over to look out the door and see if my aunt was anywhere in sight.
I could still hear her in the kitchen, busily making dinner. If I could do this quickly—maybe she’d never be the wiser! A part of me felt sneaky and conspiratorial, part of a secret plot that would, in its own way, undermine my aunt’s total control over me. She might think she could control me but she hadn’t reckoned with my clever mind! I half giggled to myself as I looked around for what I needed.
I’d never spent any time as a babysitter and I had no experience whatsoever changing babies. I had never really given any thought as to how a diaper was fastened but it seemed to me that all I really needed was the diapers themselves—everything else that I was wearing was more or less, reusable. I plopped myself down on the changing table and began fumbling clumsily at the crotch snaps on my onesie. I was amazing how awkward it was and it took several attempts before I finally got them all undone.
The stretchy material popped back and up towards my waist, at least making the rest of my job easier. Putting my thumbs inside the plastic baby pants, I worked them off of the pee-soaked cloth and down the rest of my legs. Working quickly, I unpinned either side, removing the pins, and pulled the heavy cloth away from my crotch.
Suddenly, I heard my aunt calling my name.
“Joshy!” she called from the kitchen.
I froze in panic. What terrible timing!!
“Joshy!” she called again, in an inviting voice that told me dinner was ready. However, I thought it sounded as I she were nearer than the first time and I gulped in fear. I had to get changed and do it fast! Every second counted now!
With blinding speed, I yanked the bulky wet cloth out from under me and tossed it aside, frantically grabbing a few fresh diapers from behind me. I threw them down on the changing table but they became misaligned in my rush, the corners pointing in different directions.
I could hear my aunt’s approaching footsteps, with the characteristic sound of her high heels clicking on the hardwood floor of the hallway.
She would be here any second!
Now in a frenzy, I dropped myself onto the skewed diapers and hastily grabbed the front section, pulling it up and back over my groin. Aunt Emily’s footsteps were quickly getting nearer and with a sinking feeling, I realized I’d never make it. Just as I was about to jab the cloth with one of the diaper pins, my aunt opened the door and stepped into the room.
Her look was one of utter shock as she took in the scene before her. Her pretty mouth dropped open and she stared aghast at the sight of me fumbling clumsily with my diapers.
In an instant, her delicate eyebrows arched in anger and she fixed me with a withering glare that almost made me wet myself all over again.
“I-I-I-,” was all I managed to babble as she swiftly crossed the room and snatched up the paddle.
“N-No-no, Aunt Emily!” I cried as I struggled to get up from the changing table.
Just as I was about to get to my feet, Aunt Emily grabbed me by the wrist and yanked me over to her, sending me tumbling off balance.
“Looks like I didn’t spank you hard enough this afternoon,” she said grimly as she pushed me over her lap.
I landed with a squeal of fear and anguish against her bare thigh, only to have her jerk the diapers away I had clumsily started to put on. With my fanny now clear, Aunt Emily raised the paddle up high and brought it down with a scalding slap.
SMACKK!!
“YEOOWW!!!” I wailed and instantly I burst into tears.
SMACKK!! SMACKK!!
Two crisp, well delivered swats landed on each pink cheek, leaving a crimson, rectangular pattern by the Spencer paddle. My feet scissored in the air wildly as I bawled like a baby. The paddle came down again and again, slapping both tender cheeks vigorously and making me shriek with pain.
Her hard wooden paddle was as unforgiving as it was inflexible and my buns were certainly paying the price for it. I realized belatedly that having sat in a pee soaked diaper had contributed to make my bottom all the more tender but Aunt Emily was showing no mercy at all. I pounded my fists on the floor and sobbed uncontrollably as she kept up a steady rhythm on my behind.
SMACKK!! THWACKK!!! SMACKK!! CRACKK!!
I tried squirming in her lap but she could sense my efforts to position my bottom in such a way as to take the attention away from a particularly painful spot. She responded by gripping me firmly and slapping that spot with even greater vigor.
Finally, the terrible punishment was over and I lay in place, gasping for air and sobbing like a baby.
“I can see that stronger measures are going to be necessary to keep you from meddling with your diapers,” Aunt Emily said as she brusquely helped me up to my feet. For the moment, I simply ignored what she was saying; shaking my fists and stomping my feet on the ground in frustration. I cried vocally and loudly, looking very much like a punished, spoiled toddler. My aunt ignored me, standing up and hanging the paddle back up on the wall where it belonged. Going over to the pink dresser, she opened one of the drawers to locate something. I saw her carefully sifting through some of the babyish clothing and then she came back over with a pair of soft, fuzzy white mittens, and a roll of duct tape. Taking one of my hands, she balled it into a fist and then placed a piece of duct tape over it to keep it closed. Then she placed one of the mittens over it and buttoned the row of tiny buttons that held it snugly in place around my wrist. I couldn’t stop crying as I tried to understand what she was doing to me and I watched helplessly as she repeated her maneuver with the other hand.
“There—that should keep you out of trouble,” she said with a smug smile.
I looked at my captive hands, holding them up before me in disbelief as I tried unsuccessfully to remove the mittens.
A fresh torrent of tears streamed down my face as I realized she’d won again and I was even more helpless than before. I would be totally dependent on her for everything now and I sobbed disconsolately.
Aunt Emily’s face lost its angry look and she now gazed at me with sympathetic understanding.
“Now, now…I know this a lot to take in, all in one day, Joshy,” she said trying to console me, “Hopefully, I won’t have to spank you like that ever again. Now that you understand that I’m the boss around here, I’m sure we won’t have any more misbehavior.”
I burned with resentment at her superior tone; haughty and confident and knowing there wasn’t a thing I could do to oppose her. Sniveling and sobbing, I looked up into her beautiful eyes and I hated her. I hated her for humiliating me, for spanking me, for lording over me with her rules, but most of all, I hated her because she was so pretty and sexy and totally unreachable by me. I hated the fact that even through my resentment and anger, I still wanted her worse than ever and I detested myself for being so weak.
But that wasn’t the worst of it. The worst part about it, was that she knew I wanted her and wanted her bad. I could see it in her eyes and it only increased her sense of superiority over me. She didn’t need me but I desperately needed her and she knew it. She had that smug confidence that I found so irritating, hidden behind a veneer of kindness and understanding.
How could a woman have such a hold over another person? It didn’t seem possible. She was like a mother/babysitter/idol that I never had.
-
“Come on Joshy, let’s get you changed for bedtime. What kind of mommy would I be if I left you without any ‘protection’?”
Her smile had returned to her face and once again, I was helpless to resist her. She sat me down on the changing table then suddenly hurried out of the room to get something. She returned in less than a minute with another big baby bottle full of what looked like milk which she positioned at my lips.
“Open up, Baby,” she sang, “Maybe this will make you feel better.”
I was in no mood to argue and I accepted the warm rubber nipple into my mouth, only to be rewarded with warm formula this time. It tasted horrible and I tried to voice my displeasure but Aunt Emily took my mitten and brought it up to support the bottle.
“There—you try and hold that while I change your diaper—okay Honey?” she said encouragingly, “I know that probably doesn’t taste so good but you’ll get used to it—all babies need their formula—and I’m going to make sure you get some each and every day.”
I whimpered in defeat and choked back another sob as I suc-ked from the heavy bottle balanced in my hands.
“I also put a little something in that one to help you sleep. It’ll help relax you and get you started on the right path of wetting the bed regularly. Tomorrow, you’ll wake up with a very wet diaper, as you will every morning from now on,” she assured me.
Tears were still trickling down my face and Aunt Emily could see I was distraught as she coated my stinging bottom with diaper rash crème. Out of the corner of my eye, I saw her reach over and pull a small, narrow looking rubber implement, shaped like a sausage from the shelf.
“You poor little thing--Maybe I’ll just help ease your burden a bit here.”
With those enigmatic words, she coated the strange looking tool and began gently rubbing it against my back hole. I squirmed in protest and whimpered, trying to prevent her from pushing it inside me as I could feel her trying to do.
“Just relax, Joshy…relax and open up for Mommy…” she whispered in her sweet voice.
The soft, pliable device suddenly slipped past my sphincter with surprising ease and I squealed with distress. My eyes went wide as I felt something that was so obviously foreign invading my hole but Aunt Emily merely smiled down at me. She let the device rest there for a moment, allowing me to get used to the feel of it. I felt emasculated and helpless, being violated by my aunt in this intimate manner but then she started to slowly move the thing in and out. At first, I didn’t know what to make of the strange sensation and then unfamiliarity soon turned to pleasure. She began softly rubbing it across a sensitive nerve inside me and I moaned involuntarily.
“Mm-hm,” she said as she beamed down at me knowingly.
She continued her rhythm and I closed my eyes as I relaxed and gave in to her ministrations. Like a big circuit breaker being thrown, I found myself instantly horny again. I gazed up at my sexy aunt through half closed eyelids, reveling in the ecstasy she was providing.
“Most sissies take to this right away and they soon begin to crave it,” she whispered softly.
I was delirious with pleasure and my pen-is was fighting frantically within its prison. In no time at all, I was breathing heavily and I gazed up at Aunt Emily with unconcealed lust. Staring at her big, round breasts within her snug white halter top, I licked my dry lips in sexual avarice.
“That’s mommy’s little baby,” she said in that sultry, sexy voice, “Take it like a good little girl.”
I was only too happy to comply with that instruction except my wiener was starting to ache pretty badly. She had brought me to the precarious edge of c-umming like I’d never c-um in my life but my chastity device was preventing it from happening.
Aunt Emily reached down with her free hand and gently squeezed my swollen, c-um-filled balls, smiling sweetly at me. I moaned as the sensations swept through my body, filling me with unrequited pleasure.
Taking the nipple from my mouth for a moment, I looked up at Aunt Emily with a look of desperate pleading.
“Mo-Mommy, p-please…will you please take off my chastity device, just this one time?”
Without answering me, she smiled warmly at me and gently pushed the big rubber nipple back into my mouth, denying me any chance of satisfaction. I whimpered in defeat and tears of frustration spilled down my face.
“Sorry little sissy, your little peanut has to stay where it belongs, locked and caged.”
She continued for about another five minutes, making me gasp and moan from the torturously erotic sensations. I kept flexing my aching pen-is, hoping somehow the stimulation she was providing could take me over the edge. I felt like I was so close—so desperately close to an earth-shattering orgasm but I just couldn’t take it that last millimeter. Panting and moaning, I surrendered to the waves of pleasure rippling through me as she kept up her maddening sexual torment. Suddenly, without any warning at all, she pulled out the slippery tool and put it aside.
“Okay, that’s enough for now…maybe it’ll give my baby something to dream about when she’s in her crib tonight,” she told me with a giggle.
I let out a cry of anguish and beat my mittened fists on the floor in utter frustration. I had never been so incredibly aroused in all my life. My pen-is was still throbbing out of control and I would have been willing to cut off my ear to have an orgasm at that moment.
After a quick dusting of baby powder, Aunt Emily quickly and efficiently pinned up my diapers and put another pair of plastic pants on me. I was beside myself with horniness and I wanted nothing else than for her to stick that tool back inside me and stimulate me some more. In desperation, I suc-ked feverishly on my bottle, swallowing large gulps of the disgusting tasting formula to assuage my frustration.
“That’s a good little girl, drink it all up,” she said as she saw me finishing the bottle.
“And now let’s just get you changed into a fresh nightey and then it’ll be beddie-bye time for mommy’s baby.”
Aunt Emily looked so sexy to me that I literally drooled at her with lust. My pen-is ached painfully in its cage as it continued to struggle in futility to get a hard-on. Seeing my look of sexual craving, Aunt Emily winked playfully at me and then she popped a large pink pacifier into my mouth. I squealed in surprise but she giggled and sat me on the edge of the crib mattress.
“There you go little sissy, suc-k on that while mommy finds you a nightey to wear,” she remarked.
I pouted in silence, wearing just my diapers and Ked’s as she sifted through the closet looking for a particular outfit. Soon, she came over with a soft, flimsy pink nightey with layers of ruffles along the hem and short sleeves. Within a matter of moments, I found myself becoming sleepy and I began to waver before her as she removed my onesie and drew the nightey down over my raised arms. My eyelids grew heavy and a blanket of weariness descended over me.
I was only vaguely aware as Aunt Emily tucked me into my crib for the night. She placed my teddy bear under my arm and drew the baby blankets up around my shoulders. My pacifier had fallen out on the vinyl surface of the mattress and she eased it back into my mouth before beeping me on the nose.
“Sweet dreams, my little baby girl,” she whispered, “sweet, wet dreams for mommy’s little sissy.”
-
That night I dreamt of Aunt Emily.
In the strange, subconscious world of dreams in which we have no control, my anger and resentment towards her were absent. Thus unrestrained, my subconscious longing for her met no obstacle and I was openly in awe of her, hiding none of my feelings. I dreamed we were kissing, nothing more, but passionately enough that nothing else mattered in the world for me. She was so pretty, and her body so enticing, all I wanted to do was go on kissing her soft, full lips. I had to stand on my tip-toes in order to reach up to her and I felt all the more inferior as a result. Still, it was turning me on incredibly and my heart was racing as our tongues intertwined with erotic abandon.
I woke up to the dull ache of my pen-is, fighting to get hard in my chastity device, once again. Unfortunately, there was little I could do, once it had gotten to this state of excitement, other than to grit my teeth and wait impatiently for the inevitable while trying my best to withstand the pain. Eventually, as it always did, my pen-is lost the battle and it subsided in ignominious defeat, filling the tube but no longer straining to the point of agony.
Besides the fact that I was no longer able to achieve an orgasm anymore, it frustrated me to no end that I couldn’t get a basic erection. Just a simple stretch of my organ to feel like a man again, but, like everything else, that had been taken away from me by Aunt Emily. And the longer I went without feeling the mundane pleasure of a hard-on, the more I felt feminized and controlled.
As it was, that sensation was soon overshadowed by a new and unfamiliar one this morning. After I got over the pain of my failed erection, I suddenly became aware of the fact I was wearing a very wet diaper. I had slept so soundly, I hadn’t even been aware of a need to pee but the cool, clammy embrace against my hips and loins told me sometime during the night, I had wet, and wet heavily. It made me feel very childish; all the more so since there was nothing I could do about it until Aunt Emily came in to let me out of the crib.
I still couldn’t believe everything that had happened yesterday. Had it all been a dream? I blushed hotly as I re-lived the experience of being led out to the lawn table, in that fuzzy Care Bears onesie with my fat diapers obvious to everyone. I could still remember their mocking laughter and teasing as I stood there like a punished toddler who had just been given a humiliating spanking over his mommy’s lap. Except that I was almost thirteen years old now and ready to start junior high school. I would never forget that devastating experience as long as I lived and I’d never forgive Aunt Emily for subjecting me to it.
My mind naturally turned to re-live the two blistering spankings I had received at my aunt’s determined hand as well. Never in a million years would I have thought she could paddle like that! My bottom was still sore this morning and I knew it would hurt every time I sat down for the foreseeable future. One thing was for certain—she was definitely the boss around here--no way was I going to argue with her anymore.
This morning, as I had done thousands of other mornings, my hands went down instinctively to rub the front of my crotch, only to realize they were still trapped by the restrictive mittens she had put on me. I slammed them down hard on the crib mattress in mute frustration. I was so helpless! I’d never experienced anything like this in my whole life!
Just then, the door to the nursery slowly opened and I saw Aunt Emily’s pretty face peek in, followed by the rest of her breathtaking body as she glided gracefully into the room, a full baby bottle in her hand.
“Joshy? Are you up yet?” she asked in a whisper.
“Yes, Aunt—I mean Mommy,” I replied respectfully. I wanted to stay on her good side today and do anything necessary to avoid any more trips over her lap if at all possible.
“Hello, little Sugarplum!” she said brightly, “How’s my little baby girl this morning?”
“Okay,” I replied neutrally. I don’t know why she insisted on referring to me as a girl--even though I had been dressed like one for the last 24 hours—but it still annoyed me.
She quickly unlocked the crib top and swung it back, after which she unlatched the side and brought it down. This morning, she was wearing a snug, pink top that was so low cut I could see the sexy white lace of her push-up bra partially exposed at the edges. I swallowed hard at the sight and tried to fight it but it was hopeless--my pen-is had a mind of its own. In no time at all, it was struggling to get hard again and I winced from the pain.
“Here you go Baby,” she said as she handed me the baby bottle and helped me out of the crib.
It was difficult to hold the bottle with my mittens and several times, I came close to dropping it. Leading me over to the changing table, she sat me down and placed her slim hand on my crotch.
“Looks like mommy’s little baby had a very wet night,” she said with a gleam in her eye, “but don’t you worry—I’ll get you changed into a nice fresh diaper right away. You’ll be all safe and secure in just a jiffy!”
I began dutifully nursing on the bottle of warm milk as Aunt Emily busied herself, pulling down my clinging plastic panties and throwing them in the diaper pail. My heavy wet diapers soon followed and Aunt Emily began gently cleaning my rump and between my legs with a baby wipe.
I nursed from the bottle in frustration as I gazed at her huge, pendulous breasts, jiggling and swaying within her tight, tantalizing top. She was so unbelievably sexy, I wanted to cry!
“Up you go, Sweety,” she said as she lifted my ankles and slid a fresh trio of soft diapers under my sore bottom. Taking a big handful of diaper rash crème in her delicate hand, Aunt Emily began smoothing the cool substance across my buns in a comforting, circular pattern.
“Baby’s bottom looks sore from her spankings yesterday,” she commented, using that third person vernacular one would expect from a mother, “Does your little fanny still hurt?”
I nodded as I nursed from the warm milk.
“Well, hopefully, that’s all behind us,” she said, giggling at her own pun.
I certainly hoped so, I thought as she shook the baby powder between my legs and over my chastity device. Pulling the thick cloth up, she snicked a pin through one side and then the other.
“There you are Joshy!” she exclaimed, quite happy with her handiwork, “A nice, fresh diaper for you. Now all you need is your plastic panties and you’ll be ready to take on the world!”
I blushed at her subtly condescending words but continued nursing from my bottle.
“Let’s see…what can we find for our little sissy today…how about something fun…
“Here you are,” she announced brightly, “These are cute, aren’t they Joshy?”
I nodded as I looked at the pink vinyl panties she was holding before me. They were decorated in a nursery print with giraffes and bunnies with soft lilac ruffles around the leg and waist openings. Gathering them in her hands, she beamed down at me as she put them over my feet and began snaking them up my legs. It took a moment to work them over the thick bulk of my diapers and she ran her long fingernails around the elastic waistband until the panties covered the entire diaper. With a quick dusting of powder between my legs, she brushed her hands together in satisfaction.
“Well look at you,” she said with pride, “You’re diapered just like a big sissy should be. That should hold you until at least lunch time.”
She removed my nightey and then replaced it with a short white diaper shirt with frilly pink short sleeves and a design of building blocks across the chest that spelled out ‘Bedwetter’.
“That’s appropriate, don’t you think, Joshy?” she said as she adjusted the short, Birdseye laced-hem below my navel.
“Uh-huh,” I said without enthusiasm.
“That’s why your crib mattress has a waterproof sheet covering it,” she explained as she removed my socks and replaced them with white lacey anklets, “It protects your mattress for when you wet the bed, Sissy.”
Taking a pair of glossy black Mary Janes, she buckled them over my feet and helped me to stand up.
“Take a look at yourself in the mirror, Joshy,” she said encouragingly.
I turned to face the mirror as Aunt Emily stood behind me, looking at my reflection proudly. As she bent over slightly to speak in my ear, I could feel her big, soft breasts pressing against my back.
“Aren’t you just the cutest little baby,” she remarked and she gave me a playful kiss on the cheek.
Looking in the mirror I was shocked by my infantile appearance. Unlike yesterday, when I had been wearing a onesie, today my diapers were totally exposed and the babyish pink nursery print of my shiny panties seemed to shout out loudly at what a baby I was. My ‘bedwetter’ top struck me as a badge of shame, announcing my new and humiliating status to the world. And as I shifted in my feet, I blushed at the sissyish look of my Mary Janes and anklets.
Aunt Emily picked up my pink pacifier from the dresser top and looped it over my head, after which she popped it in my mouth. Her hand dropped down and gently patted me on my thick, diapered seat.
“Welcome to babyhood, Joshy,” she said with a smug smile.
I winced helplessly as my buxom aunt led me out of the nursery and into the kitchen where she helped me up into an oversized highchair. There was a step to allow me to climb into the chair but once I was seated, Aunt Emily removed the step, leaving my feet without any support. It made me feel all the more helpless as my feet swung uselessly. She then secured a sturdy plastic tray in front of me, further immobilizing me.
I heard the microwave ding and Aunt Emily went over and retrieved another baby bottle which she brought over.
“Time for some more formula Baby,” she sang merrily.
“Uh-uh,” I protested fussily as I shook my head. I hated the taste of that stuff and I didn’t want to be forced to drink it again this morning.
“Here you go, Princess,” she said, totally ignoring my resistance.
“Uh-uh!” I repeated but she pushed the rubber nipple into my mouth against my will and tilted the bottle upwards. I kicked my feet helplessly and waved my mittened hands in the air but I could feel the formula flowing onto my tongue. Some of it trickled out of the corner of my mouth and it dribbled down my chin.
“Oh my, I almost forgot your baby bib!” Aunt Emily exclaimed.
She set the bottle down and reached over to the counter, taking a plastic bib and tying it around my neck.
“I don’t wanna drink that stuff!” I complained bitterly.
“Now Joshy,” Aunt Emily said as she picked up the bottle and pushed it back into my mouth, “All babies need their formula—you’re just going to have to get used to it.”
I whimpered in defeat as she held the bottle in place, forcing me to drink the hated liquid.
Just then, the doorbell rang and I nearly choked in panic.
Aunt Emily seemed unconcerned and she shouted for the person to come in as she continued to hold the bottle in place. I couldn’t believe she was going to let someone come in with me dressed like this. It could be anyone!
As the door opened, I nearly wet myself in angst and I recognized Aunt Emily’s cruel but busty friend, Lauren. She was wearing a pair of snug shorts and a tight yellow buttoned t-shirt that hugged her big, mouthwatering breasts in an erotic embrace that made me gulp. Her top said ‘milk maiden’ on it which struck me as appropriate.
After closing the door, she sauntered over and looked down at me disparagingly, shaking her pretty head at my predicament.
“What a sissy!” she stated emphatically.
“Hi Lauren,” Aunt Emily grinned at her friend, “How’re you today?”
“Great—my boyfriend’s taking me to a movie later on and then we’ll head back to my place for a little fun,” she said with a knowing wink.
I burned with jealousy at the thought of another guy getting to enjoy this babe in a way that was totally off limits for me. Wearing fat diapers and a ‘bedwetter’ top didn’t exactly increase my eligibility towards the opposite sex. She looked down at me with her smug look of superiority knowing I wasn’t worthy of the title ‘guy’ but instead, something more accurate like ‘sissy’.
“What’s new with you?” she asked my aunt casually.
“Well, Joshy here had his first wet night in the crib last night,” she explained matter-of-factly, “His diapers were soaked when I came in this morning to wake him up.”
“Sounds like he’s taken to babyhood like a fish to water,” Lauren remarked caustically.
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wonderful. soon a full breastfeeding and perhaps being put into a cute baby’s dress as Josh slowly accepts, and enjoys, his regressed and feminized submission. This is my favorite active story on any site. well written and accurately describes the sweet ambivalence of becoming - of accepting oneself as - an adult sissy baby. He is super lucky to have someone to help and care for him on his way.
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I blushed, unable to defend myself with the rubber nipple still filling my mouth.
“He certainly has,” Aunt Emily agreed, “But I keep him well protected against any accidents, as you can see.”
Lauren leaned over, giving me an eye-popping view down her top as she looked at my fat, bulging diapers clearly in view.
“Yes, I can see that. Your little bedwetter looks like he’ll be able to pee all he wants now, and not have to worry about the consequences.”
“Ahh…the life of a baby…” my aunt said and they both broke out laughing at my expense.
I had finished the formula and Aunt Emily took it away, to bring over a bowl of pureed baby food.
“Can you start him off on this while I go to the bathroom,” Aunt Emily asked Lauren pleasantly.
“Sure thing,” she said with an evil gleam in her eye as she picked up the big spoon and shoveled a pile of the slop onto it. Aunt Emily disappeared down the hall and Lauren held the spoon up to my face, a mischievous grin telling me she had something in mind.
“Open up Pamper Princess,” she said evenly, “Time for breakfast.”
I opened my mouth but she shoved the spoon in too quickly and much of it slopped down on my chin.
“Mmmphh!” I squealed in protest.
Grinning like a Cheshire cat, Lauren scooped up another spoonful and brought it up to my lips.
I kept my mouth shut as I struggled to contend with what was already filling it.
“Open up Joshy, or I’ll tell your mommy you’re being disobedient again,” she warned me.
I shook my head even as I attempted to swallow the revolting slop in my mouth. Prying my mouth open, Lauren forced the spoon inside although once again, a great deal of it spilled down my chin, landing with a splat onto my bib.
“Uhmm!!” I cried desperately.
She slapped my bare thigh briskly and I cried out again in pain.
“Bad baby!” she snapped, “Do I need to pull you over my lap and paddle your sissy bottom?”
“No!” I cried with my mouth still full of the tasteless glop.
“Then you’d better start cooperating—right now,” she informed me icily as she brought another spoonful up to my lips.
A tear trickled down my face as I opened up obediently to accept another portion which she quickly shoveled into my pouting mouth.
“That’s better,” she said with stern satisfaction, “Your problem is that you need more discipline.”
I looked at her fearfully as she brought another spoonful up to my face. I gulped down the mouthful I had and opened up dutifully for the next one just as Aunt Emily came back into the kitchen.
“How’s my little girl doing?” she asked.
“She’s a very messy eater, as you can see,” Lauren remarked disdainfully.
By now, baby food was spilled all over my chin and bib and I looked like a total mess.
“Oh my—yes,” my aunt agreed, “Well, fortunately, his clothing is easily cleaned and with his baby pants, you can just wipe the food off with a sponge.”
“Mm-hm,” Lauren giggled, “that’s one advantage of wearing plastic panties, isn’t it Sugarplum?”
They both laughed and another tear trickled down as I endured her humiliating taunts, unable to do anything about it.
Just as she brought up the last spoonful, the doorbell rang again.
Not another person!
Aunt Emily went to answer the door and in came another one of her friends, one I didn’t recognize. This one was younger, maybe 18 or so, with long, straight silky blonde hair spilling over her soft, bare shoulders. She looked like an absolute stunner and I blushed hotly as she came in and looked at me for the first time. She was wearing a small white crop top that showed off her flat tummy and covered a plump set of breasts that were perfectly shaped like two cantaloupes.
“Oh—my god,” she said as she shook her head and stared at me in amazement.
With baby food all over my chin, I stared down at the plastic tray in front of me, a helpless captive of these hot babes before me.
“You are the biggest baby I’ve ever seen in my life!” she exclaimed.
Before anyone could say anything, she burst out laughing, showing me a perfect set of white teeth.
“What a total sissy!” she exclaimed emphatically once she’d stopped laughing at me.
I was struck by the vast gulf of difference between us. Her face was model perfect with her make-up tastefully done while mine was splattered with caked on baby food. She looked at me like I was a total loser.
Aunt Emily removed the tray which only seemed to expose me more, especially when she untied my bib and revealed the top I was wearing underneath.
“Ha ha!” her friend laughed mockingly, “’Bedwetter’! How appropriate.”
I was crushed with shame and I felt like I was on the verge of bursting into tears at this merciless assault on my dignity.
Aunt Emily seemed to take sympathy on me and after cleaning my face with a wet rag, she helped me out of the chair, standing me up in the middle of them.
“Go and play in your nursery, Joshy,” she said as she sent me off with a motherly slap to my diapered bottom.
Wearing a baby’s diaper and a sissy top, I felt so inferior to these sexy babes with their big bosoms and pretty faces.
I fled the scene of shame as fast as I could waddle out of there. Going into my nursery (was I already starting to think of it as mine?), I sniffled in misery at the humiliation that seemed like it would never end.
With my hands immobilized in the mittens, it was virtually impossible for me to do anything on my own. Sitting on the floor, I gazed at my reflection in the mirror and realized why Aunt Emily’s sexy friend had reacted like she had. I did look like a total sissy, if not an oversized baby. Turning around, I looked in dismay at my fat diapered bottom, the shiny plastic panties only emphasizing my babyishness.
I sat down with a sigh, resigned to my new life as a prissy infant.
As I got bored, I began playing around with some large blocks with single letters on them, stacking them up as best I could with my mittened hands. I could hear the sounds of Aunt Emily and her friends in the other room, giggling and chatting amongst each other.
Before too long, I began to feel the call of nature and all that liquid I had drank was now starting to make itself felt in my bladder. Frustrated at my aunt’s new sissification regime, I decided I’d outwit her and save my peeing for when she’d be forced to let me in the bathroom to do my #2 business. Maybe I couldn’t stop her from dressing me up like a baby but at least this way, she wouldn’t be able to make me wet my diapers like one. It shouldn’t be long before I had to go #2 and then I’d do all my day’s peeing at that time.
It seemed like a pretty foolproof plan, that is, until I started to really have to pee. I knew I didn’t have to do the other business for a while and if Aunt Emily took me in the bathroom to pull down my diapers and all I did was pee, she’d probably give me a spanking right then and there. With my bottom still pink and sore from yesterday, I couldn’t take the chance of that happening.
I shifted positions, trying not to think about it but the more I did, the worse it got. Finally, I stood up and paced the floor. That alleviated the need for a second but then it was back, worse than before. Looking at the mirror, I felt so helpless and babyish, my hands useless and wearing my childish outfit just as I was about to wet my diapers like an infant. A last, I couldn’t hold it anymore. I let go and like a dam breaking, I flooded my diaper. Hot streams of pee flowed freely, quickly soaking the front and seeping back between my legs. I whimpered helplessly as I looked at my pathetic image in the mirror, a picture of sissyish defeat as my diaper grew ever heavier.
Finally, I was finished and I stood there, not sure what to do. I didn’t want to wear the wet diaper any longer than I had to but at the same time, I didn’t want to go out into the living room and announce my need to be changed to everyone present. That would only confirm to them what a baby I truly was.
I sat down again and resumed playing with my blocks but my heart just wasn’t in it. After a while, my diaper had cooled down and its clammy embrace of my hips and loins was becoming uncomfortable. I wanted to get changed!
Standing up, I went to the doorway of the nursery. To my irritation, Aunt Emily’s friends were still there, talking to each other but I couldn’t tell what they were saying. Maybe if I listened in, I’d be able to hear if they were wrapping things up. If that were the case, I’d simply wait a few minutes and tell Aunt Emily after they left.
Walking quietly down the hallway, I stopped just outside the living room to listen some more but from what I could tell, they were making no indications of finishing their conversation. For all I knew, they might be there for hours!
With a heavy sigh, I somehow summoned up the courage to walk out and I shuffled into the middle of the living room, hoping I could whisper in Aunt Emily’s ear of what I wanted. I saw her, on the far side of the room, sitting sexily in the easy chair, her long, smooth leg draped over the other and dangling her high heel up and down. I had forgotten how perfect her legs were and for a fraction of a second, I admired her curvy calves and shapely thighs, exposed below her short skirt.
But she was some distance away and I had to waddle by Lauren and her friend first. When I had entered the room, Aunt Emily seemed to be in the middle of telling an important story to her friends and I realized I’d chosen a particularly bad moment to interrupt. I waved at her, trying to get her attention, but she totally ignored me as if I wasn’t even there. I was used to being ignored by pretty women but not by Aunt Emily, and this time, I really needed to get changed!
“Mommy?” I ventured hesitantly, but she kept talking without even looking in my direction.
On the other hand, Lauren was now watching me closely, and she wore a mischievous expression on her cute face that spelled trouble to me.
“M-Mommy?” I asked again, trying unsuccessfully to get her attention, “I wet my diapers.”
Aunt Emily’s stunning blonde friend shook her head in disgust and I blushed hotly, hating the fact that I’d been forced into this humiliating position. And since Aunt Emily was studiously avoiding my plea, I was also forced to raise my own voice louder.
“I wet my diapers, Mommy. Can I please get changed?”
For the first time, Aunt Emily turned to look at me and I could tell she was annoyed with having been interrupted. Just then, Lauren grabbed me forcibly and pulled me onto her lap, positioning me on my back so I was forced to look up at her. I squealed in surprise and I tried to get off but she held me firmly. Her huge breasts hung before me, inches away from my nose and I swallowed hard, anxious to prevent from being humiliated by her but also captivated by the fabulous view I was now being treated to. I was both mesmerized and paralyzed, her big, plump boobs hypnotizing me with their maternal allure.
With her free hand, she quickly popped open a few straining buttons from her top and the fabric sprang back, revealing her giant bosom barely held captive within her lacey bra. Using her manicured finger, she deftly unhooked the front clasp and her monstrous melons fell slightly with a wonderful jiggle, no longer constrained by the pretty cups. I struggled some more but in no time at all, Lauren had pulled her right breast out which was nearly as big as my head and she mashed it in my face, effectively muffling my cries.
“Nurse on that, Babykins,” she ordered me.
I squealed in protest but she slapped my bare thigh causing me to gasp in pain and surprise. When my mouth opened, she pushed her firm nipple into it and my squeals became muffled and quieted. My face went beet red with shame as she held me there, refusing to let me go.
Mocking laughter filled the room as the girls took in the easy way in which Lauren had defeated me with her breasts. I squirmed and fidgeted but already, I could taste her milk being released into my mouth.
“That’s it Baby…you know you need mommy’s milk…just like a little baby…that’s it….everyone knows you’re a breast feeder now…”
Her humiliating words made me want to cry but there was little I could do. I sniffled and squirmed but her warm nipple seemed to leak without any effort on my part and I was forced to swallow her breast milk.
“That’s a good little girl,” she said with condescending praise, “Nurse like a good baby.”
Without thinking, I began suc-kling away at the big nipple in my mouth, closing my eyes to the giggles filling my ears.
“Lauren…I have to say,” Aunt Emily remarked, “I think you’d make the perfect babysitter for Joshy.”
“You just have to know what a baby needs,” she replied with a wink.
“Would you be interested in helping me out from time to time? You seem like a natural choice for my little nephew and I’d prefer it was with someone he already knew and was comfortable with.”
“I’d say he’s pretty comfortable right now!” Lauren exclaimed as everyone laughed at me.
The stunning blonde looked at me and smirked.
“So….is it true that he’s got some perverted fetish for girly panties?” she inquired.
I blushed hotly at the disclosure of my intimate secret.
“Oh yes,” Aunt Emily assured her, “Even before Joshy was put back into diapers, he had a thing for prissy panties.”
The girl shook her head again as she stared at me nursing helplessly on Lauren’s swollen breast, my face red as an apple.
“One day I caught him looking at a catalog of panties and I made him confess his little secret to me,” my aunt continued, “That was when I knew for sure he was a sissy.”
I mewled in shame as they looked at me but I was powerless to defend myself. Lauren made sure I was unable to take her big nipple from my mouth and her milk was flowing quite freely by now. I had no choice but to swallow mouthful after mouthful.
“The only problem was that he was getting so excited wearing his panties and prissy outfits that he was starting to make wet spots in them,” Aunt Emily continued.
“Ewww!!” the blonde remarked distastefully.
“Yes, poor Joshy couldn’t control himself so we had to put him under strict chastity. Now, he won’t be able to get an erection or—Lauren can you cover his ears?—or m-a-s-t-u-r-b-a-t-e,” she only mouthed the last word silently but I could read her lips well enough to know what she had said.
“The Cb-3000 he’s wearing took care of that problem once and for all,” she told them, “I’ll probably milk him once a month, just to keep his prostate healthy, but he won’t be allowed to ejaculate until he’s 18.”
“That’s good,” the blonde concurred, “A sissy boy like him shouldn’t be involved with that kind of adult pleasure until at least 18, and maybe not even then.
“What kind of discipline do you use when he acts up?” she asked.
“He gets taken over my lap for a good old fashioned spanking,” Aunt Emily eagerly explained, “I use the paddle you see hanging on the wall there.”
The women’s eyes followed where she was pointing and they nodded their approval.
“Have you ever tried using a cane?” Lauren asked curiously.
“Not yet, but then, I’ve only had to discipline Joshy twice.”
“Oh, you should really give it a try,” Lauren said enthusiastically, “You can really make him dance with just a couple swats of a decent cane.”
“Does he cry easily?” the blonde asked.
“I would have to say yes,” Aunt Emily told them, “I’d say by the third slap of the paddle, Joshy was bawling like a baby. He really doesn’t have any more tolerance for discipline than a little girl.”
The girls giggled at that and I squirmed in embarrassment, my cheeks burning with shame.
“I’ll bet I could do it with one stripe of the cane,” Lauren boasted, “I’d make him put his hands palm down on the table, pull his diapers down and give him a good session with the bamboo one I have—he’d learn real quick who’s the boss.”
“Well,” Aunt Emily laughed, “I think we straightened him out on that issue last night.”
“Enemas are good too,” the blonde offered helpfully, “If he’s fussy or cranky, a nice, long, soapy enema is the perfect cure. It really helps to take the wind out of his sails.”
“That’s a great suggestion Pam. How much would you recommend?”
“I’d start him off with two quarts. Take him over your lap and feed it to him slowly—you’d be surprised how much he can take if you do it gradually,” she explained, “He’ll squirm and complain and make all sorts of promises but just keep filling him up ‘til you can hear the last bubbles going through the nozzle.”
“Oh yes,” Lauren agreed with conviction, “that’s just what this little sissy needs.”
“I like that,” Aunt Emily said with more enthusiasm than I would have preferred, “you can be sure I’ll try it some time soon,” she said agreeably.
“It’s the perfect solution for males who are overly aggressive,” Pam added, “And for those who just need an attitude adjustment.”
Lauren reached down and squeezed the diaper between my legs.
“Looks like your baby has really wet herself this time,” she said sagely.
“Hon?--”Aunt Emily asked Lauren sweetly, “can you just keep her occupied for a moment while I get her a change of diapers?”
“Sure thing,” she replied.
My aunt was only gone a minute before she came back with an armload of supplies. She laid out a vinyl changing blanket and Lauren helped me to lie down on it. I was mortified at the prospect of having my wet diapers changed in front of Pam but after hearing their discussion of how best to discipline me, I wasn’t about to make trouble.
Lauren had already made herself presentable by putting her breast back in her bra although her top was still tantalizingly unbuttoned. She popped my pacifier in my mouth as Aunt Emily began peeling my wet, clinging plastic panties down.
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Great update Baby Bobby, I can almost taste that delicious milk ...
I thought for a while maybe Mother Clause had abducted you to the North Pole for a feed ...
Ace
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“Since Aunt Lauren was kind enough to feed you lunch with her breast milk, we’ll just get you changed and then you’ll be all ready for naptime!” my aunt informed me happily.
I pouted fussily and let her pull my cool, but very wet diapers off of me and set them aside. Pam bent down to inspect my chastity device close up and I couldn’t help but gaze down her top at her perfect breasts.
“So this stays on while you milk him, right?” she inquired as she pointed at my CB.
“Yes, that way, there’s no risk of him being able to c-um,” Aunt Emily explained as she smeared diaper rash ointment across my still pink bottom.
“I see how it works now…it’s only long enough to contain his pen-is when it’s soft.”
“Yes, so with this on, erections are a thing of the past for Joshy,” my aunt said as she slid my new diapers beneath me.
“Awww, poor little sissy,” Pam said with mock sympathy.
I turned my head and looked away as she took the powder from Aunt Emily.
“You poor little thing,” she said as she took a handful of powder and began softly stroking my swollen balls with it. Her hand was silky smooth and I felt electric shivers as she tenderly stroked my sensitive package. I chewed my pacifier in sexually denied angst as I turned back to look at this cruel, yet beautiful female.
She was so lovely with her pouting face and sexy round breasts, swaying slightly in her snug crop top. My pen-is quickly swelled within the tube and it strained mightily, but in utter futility against its prison.
I moaned in anguish but Pam kept tormenting me, gently fondling my sack as she shook some more powder on it.
“He has the pubic hair of a three year-old,” she observed with a giggle.
I shook my mittened fists in mute frustration until she finally bored of her game and removed her hand.
“That should give him something to remember me by,” she said with a cruel smile.
My aunt pulled up my diapers and pinned them closed on either side as I continued to shift uncomfortably. I knew it would take at least ten minutes for my pen-is to finally calm down but until then, my entire groin ached miserably. Oh, to be able to stroke my hard-on just once!
Taking my original plastic panties, Aunt Emily fed them back over my feet and began pulling them up my legs. I could feel the damp elastic of the leg holes and I protested bitterly.
“Mommy! Those are wet!” I cried as I spit out my pacifier.
Aunt Emily continued tugging them upwards as Lauren reached down and pushed my pacifier back into my mouth.
“I know Joshy—sometimes babies don’t get a complete change,” she told me, “and this will make it easier for you to wet the bed during your nap.”
I was cranky and upset, feeling the cool, damp elastic grip around my thighs as she drew the panties up and then over my bulging diapers. Worst of all was that I was afraid she was right; with part of my diapers already wet, I feared my subconscious wouldn’t try and prevent me from wetting as it normally would.
She shook the powder once more to coat between my legs and then she sat back to look at me.
“There. All diapered and ready for your nap.
“Now, give your aunt Lauren a big hug, Joshy—she’s going to be your new babysitter!” she told me cheerfully.
I can’t say I was too happy about those prospects but I got up anyway and went over to where she was kneeling. Once more, I was being forced to acknowledge the superiority of another female over me and I chafed against it bitterly.
Lauren opened her arms and hugged me, a smug look of victory on her cute face that held the promise of more humiliation and discipline at her hands.
“You’re a sweet little sissy,” she told me as she patted the thick seat of my diapers, “And I’ll make sure you get plenty of breast milk when I’m babysitting you.”
“Oh, that reminds me!” Aunt Emily said as she got up, “I like to make sure he gets a full bottle every time before he goes to bed.”
Within a few minutes, my aunt had warmed another bottle of milk and she led me into the nursery to tuck me in.
“This makes it virtually impossible for him to stay dry,” she explained as she lowered the warm nipple into my mouth, replacing my pacifier with the bottle.
“Sweet little sissy dreams,” she bade me as she closed the locking top.
I sighed as they left the room and I began nursing once again, feeling more helpless and babyish than ever.
Aunt Emily’s plans to reduce me to an incontinent sleeper worked much faster than I expected. It only took three days before I was hopelessly wetting my diapers in the crib, waking up to that cool, clammy embrace while I waited impatiently for Aunt Emily to come in and open the crib. Sometimes it would happen during my afternoon nap as well but at night times, it was now a regular occurrence. She was delighted with the change and she beamed at me with motherly pride every time she discovered I’d wet myself like a toddler. She liked to tell me that before long, I’d soon be wetting myself during the day without even noticing it.
For my part, I hotly denied it but she only smiled knowingly at me as if to say it was inevitable.
One thing I had to admit (at least privately to myself) was that my diapers were feeling more natural for me to wear with each passing day. Although the bulk of them prevented me from walking like I used to, I secretly enjoyed the soft swish of the vinyl as it brushed the inside of my thighs. And the bunny soft cotton felt wonderful against my skin—I just wished I had the freedom to masturbate freely into them and the constant temptation was maddening. But I had also started to develop a sense of security while wearing them—I was actually feeling safer knowing I didn’t have to worry about wetting the bed or my pants.
I found the loud crinkle my vinyl pants made to be very embarrassing as it announced to everyone in the room that I was present. Much to my chagrin, Aunt Emily enjoyed patting me on the plump, plastic covered seat of my diapers whenever I walked by and her subtle look of superiority only reinforced my feeling of defeat.
She loved my helplessness and I found it mortifying having to ask her to pull my diapers down so I could do my business in the bathroom. She kept the door open and tapped her toe watching me while I struggled to let nature run its course. Afterwards, she’d pull my diapers up and re-pin them, snugging my plastic panties back into place for the rest of the day. I soon found that my earlier plan to try and do all my peeing during this brief visit to the bathroom was destined to fail utterly because I was forced to drink so many fluids. With a full bottle at every diaper change and more at every meal, I rarely went more than a couple hours before I felt the strong need to pee again. I held off as long as I could but before long, the inevitable happened and I soaked my diapers. I then had to go and tell Aunt Emily about it and ask her to change me. Most of the time she’d lead me by the wrist to the nursery for a fresh set of soft, cozy diapers but occasionally, she’d squeeze my seat and inform me I could just wear what I had for the time being. I hated sitting around the house in a wet pair of diapers but there was nothing I could do about it. I certainly wasn’t going to argue with my aunt about it. In addition to using her paddle, she had taken Pam up on her suggestion and begun giving me warm, soapy enemas every other day. She told me that even if my behavior didn’t warrant it, the process would help to keep me “clean and regular”.
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One day, after breakfast, Aunt Emily was changing my diapers in the nursery when she told me she had some business to take care of in town.
“But don’t worry Sissy, Aunt Lauren will be coming over to babysit you today,” she explained to me.
I took that news with misgivings, since my impression of Lauren was that she was cruel, or at best, indifferent toward me.
“When are you going to be home?” I asked her anxiously as she tugged my noisy plastic panties into place over my bulging diaper.
“After your nap Honey,” she replied, “and I just know you’ll have a wonderful time with Lauren--she’s such a sweet person.”
I didn’t share that view but I didn’t say anything, especially since Aunt Emily had pushed another bottle of warm milk into my mouth.
“Since you’ll just be toddling around the house today, I think I’ll just put you in one of your onesies,” she told me as she stood up. “That way, Lauren doesn’t have to change your outfit for your nap.”
My aunt was nothing, if not practical. She went over to my dresser and brought back a pink and white onesie with the word ‘Princess’ on the front and an applique of a little baby girl below it.
“You’re my little princess, you know that?” she said brightly as she beeped my nose playfully.
I nodded as she stretched the top and brought it over my upraised arms. It was soft and fuzzy and despite the humiliation I felt at having to wear such a childish garment, it was at least comfy. Shiny pink eyelet lace edged the leg holes and sleeves, giving it a very prissy look and three rows of ruffles went across the seat. Aunt Emily busied herself, pulling the front and back together between my legs and snapping the snaps closed securely.
I was already wearing some pink Strawberry Shortcake anklet socks so my aunt helped me by tying my Ked’s for me. I thought she was done with me until she reached over to the dresser and grabbed a small bottle I hadn’t noticed before. With three generous sprays, she doused me with a sweet smelling perfume, giggling as she did.
“That’s a little something called Nursery Nights, Joshy. It’ll keep you smelling fresh and sweet for your babysitter.”
The fragrance smelled like a pungent mixture of baby powder and something familiar, yet indefinable. True to its name, it reminded me strongly of my nursery, further reinforcing my babyish feelings. I pouted silently as I squirmed, too late to be able to do anything about the scent that would be following me around for the rest of the day.
I heard the doorbell ring and Aunt Emily left to answer it. A few moments later, I heard approaching footsteps in the hallway and my aunt returned with Lauren behind her.
“Your babysitter is here, Joshy!” Aunt Emily announced happily.
Lauren was wearing a short black skirt and matching patent leather high-heeled pumps. Her cream colored sweater was the button down type but it looked like the buttons were at the point of failing any minute. Her big, impressive chest was pushing the material to its limits, straining the overtaxed buttons beyond their intended design. Her long, luxuriant dark hair flowed freely over her shoulders and my heart skipped a beat as I looked up into her pretty, yet condescending eyes.
“How’s mommy’s little breast feeder?” she asked, feigning concern for me.
“I’m sure she’s looking forward to a nice long feed from you this afternoon,” Aunt Emily remarked, her admiration for her lactating friend obvious.
“Oh, I’ll make sure she gets her fill,” Lauren promised with a smirk, “I’ll bet you’re just dying to get one of my nipples back into your mouth, aren’t you?”
I blushed hotly and squirmed in place as the vinyl crib mattress covering crinkled under my thickly padded seat.
As she teased me, she gently hefted one of her large breasts in her small, exquisitely manicured hand, dwarfing it by comparison. Despite myself, I felt my little pen-is hardening painfully within my chastity device. I hadn’t been horny before but now I felt the incessant throbbing in my groin as I stared with barely concealed lust at her big, luscious bosom, barely contained by her fuzzy sweater.
“Yes, I can see you are,” Lauren answered for me, giggling at my desperate plight.
“Well, I was getting ready to go--can you handle her from here?” Aunt Emily asked Lauren.
“Oh sure, I’ve got everything under control—are you ready to take off?”
“Almost, I just need to get changed for my date,” she replied as she turned to go into her own bedroom.
Her mention of a date was like a knife being driven through my heart and I nearly gasped with pain. Up until now, I had had Aunt Emily’s attentions all to myself and while I knew realistically I could never expect anything sexual from her, it was still devastating to hear of her interest in another male. I burned with jealousy, which was fueled by my resentment of her successful efforts to transform me into a sissy baby girl. Obviously, in my present state, there was no way I could compete with her boyfriend, or any other male for that matter. Looking down at the soft, fuzzy bulge of my onesie that was stretching over the thick bulk of my diapers, I knew I was nothing but a big baby in her eyes.
For the moment, I sat there alone and ignored as the two of them went into Aunt Emily’s room to chat. I sighed heavily, my sadness casting a gloomy cloud over my head.
After a few moments, I grew bored so I went out of my nursery and into the hall. Off to my left, I heard the two women’s voices as they spoke in excited tones about Aunt Emily’s date. As much as it pained me to hear it, I felt compelled to listen in on what was being said and I couldn’t resist the urge to sneak up and eavesdrop outside her door.
Tip-toeing up to the door and peeping through the crack, I could clearly see Aunt Emily in a ravishing state of undress. She had slipped out of her casual clothes and changed into a black silky bra and matching thong panties. I gaped in awe at the two perfect globes of her pert fanny, framed by the loose straps of her garter belt. My heartbeat kicked into overdrive as I had never seen such exciting undergarments on a real woman. I gulped hard and watched in captivated silence as Lauren helped roll her seamed stockings up her fabulous legs.
Instantly my little pen-is hardened and filled the limits of my CB, causing me to wince with pain. In helpless frustration, I reached down to stroke the front of my diaper, realizing for the thousandth time, that there was absolutely nothing I could do to alleviate my raging sexual appetite. It was so maddening!
Lauren rolled up the delicate, silky material over Aunt Emily’s smooth, firm thighs and I let out a sigh of admiration. Such perfection!
She attached the little straps at the tops of the stockings and then adjusted the fit down the length of her legs to straighten the seams.
“What do you think of these heels?” Aunt Emily asked as she held a pair of glossy, black patent leather 5” high heels sandals.
“Oh my god, those are sexy,” Lauren exclaimed and she took them to help my aunt put them on.
My wiener was throbbing insanely as I watched Aunt Emily sit down on her bed, crossing her sexy legs to make it easier for Lauren to buckle the tiny straps.
Looking at her angelic appearance, I knew she was way, way out of my league but I couldn’t help burning with jealousy as I saw that she was dressing to the nines for some other guy. Worse than that, was the fact that I was desperately horny and frantic to get some relief and Aunt Emily had made sure I’d be prevented from doing so. I stomped my feet in frustration as I unconsciously rubbed the front of my soft diapers in mute helplessness. I bit my lip as I reflected on the incredible inequity of my situation. Some guy was going to have all kinds of fun with my sexy aunt and once again, I’d be spending another long afternoon, frustrated and horny in my sissy diapers.
Aunt Emily slipped on a slinky, snug top and I could just make out the enticing lines of her bra underneath, pushing against the tight material by her big breasts. I shook my head in amazement at how incredible she looked, standing in her high heels and stockings, wearing just her top above the waist. Difficult as it was, I tore myself away from her bedroom door, knowing she’d be coming out any second.
It took longer than I thought, but about ten minutes later, Aunt Emily emerged from her bedroom, sashaying with her usual sexy gait, purse in hand. My pen-is was still straining to be erect within my CB and my efforts to think about something else to distract me had failed utterly.
As she passed me, she bent over and kissed me on the cheek and I greedily breathed in wonderful scent.
“Bye-bye Joshy. You have a good day, Sweety,” she said as she stood back up and strode toward the door.
I pouted in jealous silence but she completely ignored me as she gave Lauren a hug.
“You go ahead and take off, I’ll see you later this afternoon,” her friend told her.
“Thanks Hon,” Aunt Emily said as she gave her a brief but erotic kiss on the lips. I gaped in lustful amazement as I watched their big breasts mash against each other for a moment.
“See ya, Joshy!” she called as she strode out the door.
As soon as the door closed, Lauren turned to me, placing her hands on her hips as she looked down at me, both literally and figuratively.
“You’ve got a busy day ahead of you, Sissy-boy,” she said evenly.
I gulped in fear at the sudden change in tone of her voice that suggested she had much more in mind for me than simply watching me here.
“But tell you what—I’m going to give you a little freedom by removing your mittens, and if you’re really good, maybe we can talk about removing something else you’ve been wearing.”
My heartbeat increased excitedly at this completely unexpected turn of events. Could Aunt Emily have left her the key to my chastity device?
“Are-are you going to unlock my CB?” I asked her, trembling with excitement.
Lauren smiled wickedly at me as she undid the buttons on my mittens.
“Maybe…if you’re a good little girl today,” she said tauntingly.
My pee-pee throbbed impatiently and painfully in its cage as I contemplated finally being released from Aunt Emily’s cruel and implacable chastity.
“That would be totally awesome!” I exclaimed as my hands came into view one by one.
“Well, we’ll see,” Lauren said noncommittally.
I was willing to do just about anything to be able to c-um and the thought of it being possible, changed my outlook entirely.
“Just remember,” she said sternly, “If you misbehave or back sass me, I’ll pull you over my lap and give you a spanking—got it?”
“Oh, yes Ma-am!” I quickly agreed, trying to sound as cooperative as possible.
“Okay, let’s get your purse ‘cause we’re heading out,” she said as she led me down the hall to my nursery.
“Wha-what?” I stammered. I didn’t know we were going outside!
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Another great chapter. Love your stories ?
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Delicious. Joanie has no choice but to accept the pleasures of his feminized regression to sissy baby girlhood. Perhaps he will next be enveloped in a sweet baby dress with matching plastic-lined rumba panties.