The Continuing Adventures of Baby Bobby

[Baby_Bobby]

This is story #2 in my Bobby series. I hope you all like it as well as the others I've posted here. :D

The continuing adventures of Baby Bobby

   I woke up at ten as usual when my Nanny entered the nursery. Rolling over on my plastic sheet, I gazed sleepily at her hourglass figure as she came closer to the crib, her high heels making their characteristic ‘click, click, click’.

   My nanny's name is Tiffany, a lady hired by my mommy to look after me when she's away at work. At 28, she was extremely pretty with full lips and long brunette hair. Her body was slim and tall, yet curvy and sexy in the extreme. Her bre ( " at " ) sts were large and full, always threatening to burst out of whatever top she was wearing. I think I was in love with her.

   My nanny was hired two years ago, after a little incident at my aunt's house where she had caught me stealing her panties and masturbating in them. My aunt, a very no-nonsense individual, felt the best way to deal with my childish behavior was to put me into diapers and plastic panties, and dress me like a little girl. This seemed especially appropriate because I had always been a chronic bed wetter too, only now, the diapers would be staying on permanently. When I returned home at the end of the summer, my mother was in complete agreement with my aunt's treatment of me and even took it a step further by converting my old bedroom into a baby's nursery. From somewhere, she found an oversize crib, painted my old dresser pink, and installed a diaper changing table alongside the bed. My closet was filled with frilly dresses and rompers and my dresser kept plastic panties, rumba panties and tights. On the wall, hanging from a peg, hung a well used wooden paddle, which was applied frequently whenever deemed necessary to bring me to tears.

   Looking up at my beautiful nanny, I watched as she unlatched the crib bars and swung them down and open.

   Today, she was wearing a short black skirt with dark hose and high heel pumps. Her tight white blouse gave her a very businesslike look and I was mesmerized at the sight of her lacey white bra straining against the fabric. Not for the first time, did I ache to be able to touch her bre ( " at " ) sts which were swung tantalizingly before me. I had tried that once, a year and a half ago, and she'd responded by blistering my bottom with the paddle. It was a mistake I'd never repeat.

   "How's mommy's little baby?" she asked sweetly as she pushed the rubber te ( " at " ) t of a baby bottle between my lips. Obediently, I suc-ked on the warm milk as she swung my legs out over the floor. With practiced ease, she pulled my plastic panties down from over my soaking wet diaper and tossed them into a large diaper pail next to my changing pad. I watched in silence as she unpinned my diaper and did similarly with it, where it landed with the usual thud of heavy sodden cloth.

   Taking me by the hand, she helped me out of my crib and led me over to the only chair in the room, a straight backed wooden seat where I normally received my spankings. Above it hung a large red enema bag filled to bursting with warm, soapy water. A white tube extended downward from it, ending in a thick dil-do nozzle that was buried in a jar of nursery jelly. I don’t think my mom was aware of the fact that Tiffany had exchanged the normal nozzle for a specially made dil-do-shaped nozzle—and I was too afraid to tell her about it. But I knew that my nanny loved to do things that would humiliate and emasculate me so the dil-do nozzle was here to stay, whether I liked it or not.

Tiffany sat down in the chair and wordlessly took me over her lap.

   It had been decided a long time ago that the best way to keep me from messing my diapers was to give me a long, full enema every morning. So before I was dressed for the day, Tiffany came in and slowly administered one, making sure I took every drop before she let me up to go to the bathroom.

   Today was like every day as she greased up my anus and then inserted the nozzle, burying it as far in as it would go. Without warning, she released the clip and I felt a strong surge of soapy water entering my bowels. I moaned helplessly like a little girl and stared down at her shiny black pumps, wishing I could be as strong and in charge like she was. Immediately, I felt the pressure building within me, my insides churning with the gurgling water flowing into me. I let out another moan and bunched my fists in frustration. After a short time, Tiffany pinched the clip shut and allowed the water to work its way deeper into me. When she felt I had had enough time, she released the clip again and in response, I whimpered like a baby.

   Soon I was squirming on her lap, desperate to get off and have the determined invader taken out from my bottom. As if reading my mind, Tiffany pushed the nozzle in deeper and held it there, patting my cheeks reassuringly.

   "Stop fidgeting, Bobby. You remember the last time you started squirming don't you?" she asked, "Remember when nanny had to use the paddle to keep you still? Do I need to get it now?"

   "Uh-uh!" I quaked as a bead of sweat broke out on my forehead. I knew only too well how easily Tiffany could be provoked to paddle my fanny. She had a strong arm and she wouldn't stop until I was bawling like a baby.

   The cramps inside me were tremendous and I swallowed hard praying the bag was empty.

   "All done, Nanny?" I quaked shakily.

   "'Fraid not Sissy, you've still got a ways to go."

   With that, she undid the clip again and I felt a fresh surge of hot water invading my pouting bottom. My breath was coming in short gasps and I desperately pinched my cheeks together to try and stop the flow but my efforts were futile. The big, thick dil-do nozzle ensured an uninterrupted flow of hot, soapy water was delivered to my bowels. The enema continued at Tiffany's pace for another five minutes, until my tummy was extended and I was sure no more water could possibly go in.

   At long last, the humiliating ordeal was over. She helped me up to standing position and I limped off to the bathroom, knowing the consequences for spilling any would be most severe.

   Twenty minutes later, when I returned to the nursery, Tiffany had my diapers all laid out on the changing table waiting for me. Since I wet a lot and often, they dispensed with the notion of "daytime" and "nighttime" diapers and instead, dressed me in triple thick "all the time" diapers. These were very bulky and impossible to hide but my mom reasoned that a little embarrassment was worth making sure I had no leaks.

   Resigning myself to my fate, I sat down on the big soft mass of cotton and let my nanny do her job.

   Tiffany busied herself cleaning my diaper area with some baby wipes as I sat back and gazed at the deep cleavage down her top. At sixteen, it took very little to give me an erection and despite the humiliation, I felt myself growing harder contrary to my efforts to do otherwise. Tiffany was very professional and she simply ignored it as she shook powder over my loins and pulled the thick diaper up and between my legs, tucking the top over my little hard on. Removing the pink ducky pins from between her sensuous lips, she expertly pinned me up for the day, at least until my midday changing time. Picking up a pair of pink nursery print plastic panties, she shook them out and positioned them at my feet, holding the leg openings wide. I felt so sissyish as she snaked the panties up my skinny legs, the waterproof vinyl crackling as she pulled it around and over my thick, bulging diapers.

   "There," she said with satisfaction, "all safe and secure again."

   I blushed hotly at that comment. Elsewhere, guys my age were wearing tight jeans and flirting with young women but here I was being pinned into my daily pair of diapers and plastic panties. I didn't even own a pair of jeans anymore. The closest I had to a pair of pants were some blue shorts, but they were a girlish baby blue, very short, and had elastic gathers at the legs which only accentuated the diapers I was forced to wear underneath.

   Today however, there wouldn't be even that to wear. Tiffany had chosen a frilly taffeta party dress for me to wear with matching rumba panties. First I was made to put on a silky petticoat which would add flounce to the outfit and flare out the hem of the dress. After that, she guided my arms through the party dress, a lacey ensemble any mother would be proud to dress her three year old daughter in. It was white with pink ruffles everywhere, short puffy sleeves, and a short hem that did nothing to hide my thick, embarrassing diapers. Holding the waistband of the rumba panties open, she waited as I stepped into the satiny confection and she pulled them up my smooth, shaven legs. With a few sharp tugs, my nanny succeeded in getting them over my waterproof panties and fat diaper before sitting me down at my vanity.

   "Time to make sissy's nails all pretty," she cooed as she unscrewed the top of my bubble gum pink nail polish. I fidgeted as she applied several thick coats of the polish to my longish nails telling me how pretty I would look today.

   "I've got several lady friends coming over later and I want you to serve them tea with our best china. Do you understand?" she asked.

[Anonymous]

"Aww, do I have to?" I whined, "Dressed like this?"



   "Of course, dressed like this. How else would you be dressed?" she said pointedly.



   "But I'll look like a complete sissy," I insisted, quickly realizing the futility of the argument.



   "Honey," she said looking me in the eye, "You are a complete sissy. This outfit matches your personality to a ‘T’. This isn't a temporary punishment for you--this is how you'll be dressed from now on. Permanently. Do I make myself clear?"



   "Yes Ma'am," I mumbled disconsolately.



   "Now while that's drying, come into the kitchen so I can feed you your breakfast."



   Together, we went into the dining room where she strapped me into my high chair. Using the arm restraints on either side, she secured my wrists to prevent me from making any mischief. After setting a divided plate filled with baby food before me, she placed a plastic bib around my neck. Under the colorful cartoon bears on its face was the message "Look out, wet diapers below."



   I did my best to accept the big spoonfuls of flavorless mush that she shoved into my mouth but she went so fast, that much of it ended up on my bib and chin. By the time I was finished, I was a complete mess but instead of cleaning me up, she jammed a jumbo bottle of warmed formula into my mouth, holding it in place while I suc-ked helplessly from the semi-sweet liquid.



   "That's it, drink it all up like a good boy," she said approvingly, "that's a good baby."



   I had just about finished it when the doorbell rang, causing my heart to miss a beat.



   "You stay right there," she told me, as if I had a choice, "I'll be right back."



   Opening the door wide, I caught sight of one of our neighbors, a girl about the same age as me by the name of Dixie. She had seen me before in my baby clothes and she made no secret of her disdain for me. This was a crushing blow to me, because I had often fantasized about asking her on a date, if I could've met her under different circ-umstances. She was a cheerleader at my old high school with a great body and really cute face. Today as she strode in, she was wearing a short midriff top that stretched tightly over her generous bosom and jeans that looked as if they were painted on.



   "So it's breakfast time for the sissy, eh?" she said with a sneer after seeing me strapped in the high chair, "looks like he's wearing more than he ate."



   I blushed beet red and looked down, wishing the floor would open up and swallow me.



   "Yes, Bobby's a very messy baby. Thank god, we were able to custom make his bibs to fit him," Tiffany responded.



   "Ha ha!" she laughed as she read the inscription, "Wet diapers below…How appropriate."



   Tears of shame began to fill my eyes and I pulled desperately on the wrist restraints which of course, did nothing except make me look even more like a helpless weakling.



   "You know, I almost start feeling sorry for him, and then I remember how this all got started, when you got caught m ( " at " ) sturbating in your aunt's panties," Dixie said accusingly.  



   I said nothing but bit my lip in angst.



   "Far as I'm concerned, I think you deserve all you get and more."



   Tiffany nodded her head in agreement.



   Turning back to my nanny, she said, "I just came over to tell you our phone's not working but mom wanted to know if you would mind if she brought over a couple of friends with her today."



   "Sure, that'd be great. And why don't you come back yourself, Bobby will be practicing his tea service for us," Tiffany offered courteously.



   "Yeah, why not," she said as she looked down at me with an evil smile, "I'll see you later, Baby."



   After Dixie left, Tiffany cleaned up my face and removed my bib, taking me back into the nursery. After sitting me down at the vanity, she brushed my hair into pigtails and attached a pink bow to either side. Removing my short socks, she replaced them with white lacey knee highs and strapped me into some black shiny mary jane shoes. Next came some blush on my cheeks and a generous application of Bonny Bell pink lipstick to my lips. As she stood up to admire her handiwork, she gave me several sprays of "Little Missy" perfume.



   "There. All pretty as can be," she said approvingly.



   "Go and prepare the tea set, the guests will be here soon," she told me.



   I did as I was told and as each woman arrived, I was made to greet them at the door, curtsy, and invite them inside. Each one caused a little panic in me, which had the predictable effect of causing me to wet my diaper, bit by bit. Fortunately, the rumba panties helped to keep them from sagging too much but it was still a mortifying experience.



   There were the oohs and aahs and "is the baby wearing plastic panties on underneath?" comments that caused me to redden. That only encouraged them and they teased me mercilessly about what a sissy I was.



   When everyone was sitting in the front room, all eight of Tiffany's friends, I carried the tray with the teapot and cups out to them, trying to do my best to be graceful as I had been taught. It was difficult with a thick, wet diaper on and I ended up waddling more like a toddler, than a proper maid.



   One by one, the ladies took a cup but then one of them reached behind me unexpectedly and squeezed the seat of my ruffled diapers. I gasped in surprise and I dropped the tray, causing the cups and pot to clatter messily all over the floor.



   "Bobby!" Tiffany said sternly, "you clumsy idiot! Clean that mess up immediately!" she stormed out of the room and I was filled with dread.



   Now in a state of panic, I busied myself trying to gather the items while the ladies watched me with amusement.



   "I was only trying to see if you had wet yourself, Bobby," one of the ladies offered with a giggle.



   As I was bent over on all fours cleaning up, I felt another squeeze on my pantied bottom.



   "Mmm-hm. He's wet all right. Looks like your nanny's going to have to change your diapers, Sissy," another said.



   "But first, I think someone's going to get a spanking," offered another.



   There were giggles all around as they watched me scrambling around on the floor trying to clean up my mess.



   I blushed deep red but tried to ignore their remarks as I heard the purposeful stride of Tiffany's high heels clicking down the hallway toward me. Frantically, I threw the rest of the cups on the tray in a desperate attempt to make the scene look clean. My heart was pounding and I was filled with fear over how I'd be punished. Maybe she'd just make me wipe up the mess and then start over, I thought, trying to convince myself.



   "Bobby! Set those down on the table," Tiffany ordered me, referring to the jumble of teacups on the tray.



   She had returned wearing a vinyl apron and in her right hand was the wooden paddle. I gulped as I looked at its familiar shape, oval with a number of holes drilled into the face, designed to cause that extra sting.



   "No Nanny please, I didn't mean it," I pleaded anxiously.

[Anonymous]

"Why the apron Tiff?" one of her friends asked.



   "That's because Bobby often loses control when he's over my lap. This is so he doesn't get my skirt wet," she explained patiently.



   Sitting down in one of the empty chairs, she pulled me roughly over to her by the wrist. My fluffy dress swished daintily but in my panicked state, I felt a surge of pee flood the front of my diapers and my face reddened again.



   As she had done so many times in the past, my nanny pulled my rumba panties down my legs with several sharp tugs, exposing my plastic nursery print panties for everyone to see. By now I was stamping my feet in frustration, begging and pleading not to be paddled.



   "I'll be good Nanny. Pretty please? Please don't spank me, please?" I sobbed, the tears already welling in my eyes.



   She completely ignored my whining and looked instead at the obvious wet spot covering the front of my diapers. The other ladies too could see the telltale wetness that had seeped into the seat of my diapers, darkening the lower section of my fat bottom.



   "Just look at you!" Tiffany exclaimed, "A grown boy of sixteen still wetting his diapers like a little baby! You should be ashamed of yourself!"



   I sniffled and bit my lip in shame as she scolded me severely in front of everyone.



   "Please Nanny, I won't do it again, please don't spank me," I begged her.



   "Young man, you are going to get the paddling you so richly deserve and then everyone is going to see what a big crybaby you are."



   With that, she yanked down my waterproof panties to just below my knees and then pulled me across her lap. I landed with a humiliating squish and I felt her unpinning the wet cloth of my diapers, the embarrassing smell of urine wafting into the room.



   I squirmed and fidgeted nervously as she pulled back the diaper, exposing my damp bottom for all to see. I felt a brief draft of air on my cheeks as I whimpered in fear.



   "I'm so sorry Nanny-I'll never do it again. Please, please, I'll be a good boy," I whined pitifully, "please don't spa-"



   My begging was cut short by the impact of her paddle, searing itself on my backside. At first my eyes opened wide, I was unable to vocalize a sound and I gasped in surprise and pain.



   The paddle rained down in quick succession, blazing a fierce rhythm across my sissy bottom. I shrieked in pain, sounding more like a five year old girl, than the sixteen year old young man that I was.



   SMACK!! SMACK!! SMACK!!!



   My nanny slapped each tender cheek harshly, then both, causing them to redden quickly. I kicked my feet desperately but my panties were tangled around my calves and it only made me look more pathetic.



   SMACK!! SMACK!! SMACK!!!



   I started bawling like a baby, without restraint, and the tears streamed down my cheeks. My bottom was transformed into a pair of red, hot glowing globes. When she saw that the sides of my cheeks were still only pink, she quickly turned her attention to them, slapping them painfully until they too, were a deep, cherry red. Bunching my fists, I beat on the floor as I cried and sobbed. My feet in their mary janes kicked and flailed, tangled within my plastic and ruffled panties. My nanny never relaxed her pace a bit, she just kept swinging away, delivering each stinging swat like it was to be her last. My fanny felt like a swarm of bees had attacked it but still, she refused to pause.



   I looked around at my audience through tear-filled eyes but they only smiled in agreement with my punishment. I couldn't face them so I gazed down at Tiffany's silky dark hose covered legs and the high heel pumps she wore. She was very strong and could easily support my frail, squirming body over her lap while she paddled my fanny with deep, angry smacks of the paddle. My bottom was on fire and it felt like she was spanking me with a red hot skillet.



   At last she stopped, and for a moment, I lay heaving and gasping for air. Between gulps for oxygen, I cried loudly, no longer concerned what anyone thought of me. Pulling me up, Tiffany stood me on my shaking feet, my knees knocking together and my wet diaper falling to the floor.



   "Come along Sissy. Let's get your diapers changed," she said as she pulled me by my wrist out of the living room. I struggled to follow but my panties were still tangled around my ankles. Trying to keep up with her long strides, I was forced to make short, shuffling steps and I tried to reach down to pull up the restricting panties. This only caused me to fall over and Tiffany was forced to turn around and wait for me.



   "Come along, quit dawdling!" she ordered me sternly. To emphasize her point, she took another swing with the paddle at my exposed derriere, making me jump back up and shriek anew. The ladies laughed at my childish display and I quickly retreated to my nursery, ignoring the humiliating panties that threatened to trip me with each panicked and shuffling step.



   I thought I'd have the luxury of getting changed with just the two of us but I was wrong again. The others came in after me and gathered around to watch me being put back into my diapers. I sobbed profusely as I tried to rub my blazing bottom and I stood over my changing table, afraid to sit down. Tiffany forced me down however, and I let out a yelp when my backside made contact with the cool plastic surface. I was still crying like a baby as she proceeded to vigorously rub my fiery bottom with diaper rash cream. There were numerous comments like 'look at how small he is,' and 'what a tiny wee-wee! He could almost pass for a girl.' I cried tears of shame as Tiffany selected a particularly thick set of diapers and pushed them under my bottom. With a few good shakes of baby powder on my crotch, she pulled up the front and pinned me up securely on either side.



   "Would one of you ladies pick out a pair of plastic panties for our little pampered princess? They're in his dresser drawers," Tiffany said.



   One of the ladies quickly found a pink pair with lace around the leg openings which she then brought over. With my legs up in the air, they slid the crinkly panties down my legs and wrestled it over the thick bulging diaper. By now, my crying had subsided a bit and I lay there sobbing and whimpering in shame.



   "I think it's time for our baby's nap," Tiffany announced as she unbuttoned my party dress.



   "But I don't wanna go to bed now," I protested weakly.



   From somewhere, a baby bottle filled with warm milk was produced and shoved into my mouth, effectively ending the discussion. I suc-ked obediently as she removed my slip and shoes and put me in a frilly nightey. Taking the bows out of my hair, she put a pink lacey bonnet over my head and then lowered the side of my crib.



   "Say goodbye to our guests, Sissy, it's naptime for you," Tiffany told me.



   Between sniffles, I waved goodbye from inside my crib and they each came to give me a kiss before my nanny tucked me in. My empty bottle was replaced with another and one of the ladies handed me my pink teddy bear who like me, was also diapered.  



   Tiffany turned on the mobile over my crib which played a soothing nursery tune to lull me to sleep. I hugged my teddy and suc-ked my bottle as the women left the room and turned out the lights. I was exhausted from my ordeal and soon drifted off to peaceful sissy sleep, my dreams filled with pretty panties and wet diapers.

[Anonymous]

The following day, my bottom was still stinging painfully and after my morning enema, Tiffany rubbed it generously with baby lotion before applying my diaper rash cream. After pinning me up in my thick diapers, she selected a white pair of colorful nursery print panties to go over them and then brought over my outfit for the day.



   It was a sissy sailor suit, white with short elasticized sleeves and a bib style bodice. While it was accentuated by baby blue ruffles along its waist, it also had pink trim throughout which gave it a very distinctively toddler look. Below the frilly hem were four snaps which were intended to attach to the matching shorts that went with the outfit.



   After pulling the humiliating top over my head, nanny helped me into the shorts. I had hoped they would at least conceal my diapers but they did anything but that. The thin, filmy white fabric stretched over my big bulky diapers, clearly revealing the patterns on the nursery print panties underneath. The legs were decorated with blue lace and the three snaps in the crotch made it obvious that the wearer required easy access for diaper changes.



   I blushed as she snapped the top to the four matching snaps in the shorts. They also had the virtue of helping to prevent my diapers from sagging when they became wet.



   Knee highs and mary janes were quickly put on and my hair brushed into pigtails before she led me out to breakfast.  



    I was surprised when I came in and saw Dixie standing near the table. She was facing away from me talking on her cell phone, and it afforded me the chance to stare at her heavenly body. Her long blonde hair cascaded over her bare shoulders and she wore a tight clinging halter top that showed every curve of her big boobs. Tiny shorts were wrapped around her sexy derriere and my eyes gazed down the long statuesque length of her legs to the open toed high heels she wore. My little pee-pee immediately began to harden and I couldn't take my eyes off her.



   She must have heard us come in because she turned around and looked at me with a mixture of disgust and amusement. Saying goodbye to her caller, she closed the phone and dropped it in her purse.



   "Well! Who’s the little sailor we have here?" she asked in a mocking tone of voice, "looks like he's a very well diapered little boy, from what I can see."



   It was true that despite the shorts that clung to my diapers, I still had an unmistakable bell shape appearance leaving no doubt as to what I had on underneath.



   Tiffany sat me in my highchair and after strapping me in, began my feeding as usual.



   "Does mommy's little baby still have a sore bottom from yesterday?" Dixie teased me, "I'll bet he does."



   "I was surprised how red it was when I gave him his enema this morning," Tiffany offered, "red with a few purplish welts covering most of his bottom."



   "Yes, you really know how to handle a paddle, don't you," Dixie said admiringly as she took a seat across from me and crossed her sexy legs.



   "Well, let's just say that I've handled more than my share of bed wetters and masturbators in my time," Tiffany explained as she shoved another heaping spoon of baby food into my mouth. Most of it spilled down my chin, landing with a plop onto the bib. "Of course, Bobby excels in both categories so I've really got my hands full with him. I may seem harsh with him but it's only for his own good. I can't tell you how many times I've had to paddle him for playing with himself."



   "Is that so?" Dixie exclaimed as she looked me in the eye, "How disgusting!"



   "Yes, and he's tried every trick he could to try and get away with it but I always found out in the end. He soon learned that a brief moment of pleasure wasn't worth the blistering spanking he'd get when I caught him.



   "He must be horny as hell," Dixie remarked.



   "Oh he is, believe me. Sometimes, if he's been a good boy, I'll rub some baby oil on his little wee-wee for a few moments before I pin his diapers back on," Tiffany explained.



   "Do you let him c-um?" she asked with interest.



   "Oh heavens no! No, I just let him get a little excited and then it's back into his diapers for the rest of the day."



   I blushed deeply at this discussion of my inner most secrets and realized belatedly that I was wetting myself. I had long since lost control of my bladder and I often peed my diapers without even knowing it. Unable to look Dixie in the eye, I glanced at the exposed tops of her curvaceous bre ( " at " ) sts, pushed into a dizzying cleavage by her white bra. I tried to be careful and not stare as I didn't want another session with nanny's paddle today.



   "Speaking of which," Tiffany said as if reading my mind, "here is his paddle for you to take with you--I usually put it in my purse or his diaper bag but I make sure it goes everywhere with him. You never know when he's going to act up and his behavior is much improved when he knows you can just pull his diapers down anywhere and teach him a lesson,'' Tiffany told her.



   ''Thanks, I won't hesitate to use it,'' Dixie assured her.



   I shifted nervously in my chair.



   "Where are we going, Nanny?'' I asked tentatively.



   ''YOU are going with Dixie for the afternoon. I've got some errands to run and she has graciously agreed to baby-sit you while I'm gone.



   ''And I'd better not hear that you've misbehaved or I'll paddle that bottom of yours all over again. Do you understand me?'' Tiffany said as she wiped my messy face with a washcloth.



   "Yes, Ma'am,'' I answered glumly.

[Anonymous]

As she undid the straps on my highchair, she thanked Dixie again for taking me and gave her my diaper bag which contained enough for one change.



   I didn't go out much in public so it was with trepidation that I did so now. Dixie led me out to her car by the hand and I looked around frantically to see if anyone was looking. For some reason, the crinkle-swish of my plastic panties seemed particularly loud as I walked out into the open. Here I was, walking hand in hand with one of the hottest babes in school and I was wearing a sissy sailor suit and thick diapers. It was so unfair!



   Somehow, I made it to the car without being seen and I waited anxiously for her to unlock the door so I could get in. For what seemed like forever, Dixie got her keys out of her purse, unlocked her own door and slipped inside, leaving me to stand out in the open.



   A pair of ladies were walking down the sidewalk towards me and I saw them start to look me over. Desperately, I pounded on the side of her car window to let me in but she only ignored me and started the car. I was bent over slightly trying to see what she was doing which only made my big diapered butt look even more noticeable. By now, the ladies were about fifty feet from me and I bit my lip as I debated whether I should run back inside or not. In a frenzied state of panic, I helplessly flooded my diapers as the ladies gave me a strange look. I let out a moan of shame and looked away, fighting back the tears. Finally, I heard the door unlock and as I slid inside, Dixie's mocking laughter filled my ears.



   We drove through town for about twenty minutes and despite my shame at being seen by other drivers, I found myself stealing glances at Dixie's profile.



   She really had a hot body, and her perky bre ( " at " ) sts filled her tight halter very enticingly. Gazing at her tanned, creamy thighs and flat tummy gave me a hard-on within my wet diapers.



   I had never been babysat by Dixie and her silence in the car left me to fantasize about how she would treat me. In my befuddled state, I naively thought she'd flirt with me and I dreamed of cupping her perfect bre ( " at " ) sts in my hands.



   When we arrived, Dixie seemed annoyed with me and when she came around to my side of the car, she blocked my path. Without warning, she grabbed my head and roughly jammed my face against her chest. For about three seconds, my nose was buried in her soft cleavage but her embrace was anything but gentle.



   Holding me so I couldn't breath, she suddenly pushed me back and slapped me hard in the face.



 ''There!" she snapped, "I hope you enjoyed it you little pervert, 'cause that's as close as you're ever going to get to the real thing.



“Now quit staring at my boobs!''



   With that, she stormed off, leaving me at the sidewalk to gather my wits. Glancing around quickly, I ran to catch up to her as she went up to the door and knocked on it. I thought that was strange because I assumed we were going to her house. Instead, the door opened and a big guy stood inside, towering over me. I vaguely recognized him as one of the studs from the football team, a group of people who were way out of my social circle when I was still in school.



   "Hey! I recognize you! You're that pansy  ( " at " ) ss that was the teacher's pet all the time, aren't ya?" he blurted out.



   I blushed and nodded my head.



   "Well I always knew you were a sissy. Looks like your mommy had to put you back in diapers too," he said mockingly.



   "Dixie, do we-" I started.



   "-That's MS. Dixie to you Sissy-boy," she corrected me.



   I cleared my throat and started again.



   "Ms. Dixie, do we have to stay here? I wanna go home," I whimpered.



   "Yes we do. John's got a BIG surprise for you. Now get inside," she said menacingly. She emphasized her point by slapping my diapered bottom as I stepped in the house.



   Not wanting to get in any more trouble, I did as I was told and I saw football trophies and other sports paraphernalia everywhere in John's living room. He was a huge guy, and he was everything that I wasn't: tall, muscular, macho, and attractive to the girls. Now it was painfully obvious how ludicrous my plans had been to ask Dixie out on a date. Even before I was wearing diapers full-time, she would've laughed in my face and probably told me to go play with myself. As I saw her kiss John passionately and rub his swelling crotch, I was embarrassed by the temerity of my fantasies.



   "It's time for me to put you in your place," Dixie told me, "get on your knees."



   "Wha-what for?" I asked, fearing something was about to happen that I wouldn't like.



   John whipped off his gym shorts revealing a tight pair of underwear that clung to his monstrous hard-on. He was stroking it and looking at me strangely.



   "If I tell you to do something, you'd better do it without question...or maybe I should tell your nanny that you were a bad boy today?" she said with a wicked smile.



   "No Ms. Dixie, please don't!" I quailed as I dropped to my knees.



   With obvious admiration, Dixie pulled John's underwear slowly down his big muscular legs with her manicured red nails, exposing the biggest coc-k I had ever seen in my life. It sprung to attention like a battering ram and my heart began to pound in my chest.



   With a few steps, he stood before me, looking down at me with his coc-k mere inches from my face.



   "Time to learn what it really means to be a sissy, Bobby," Dixie told me in a throaty tone of voice, "you thought being a sissy just meant wearing diapers and dresses but now you're going to find out the true meaning. Take his coc-k in your mouth."



   I gulped hard and looked up at her pleadingly. I was still a virgin and hadn't even kissed a girl before besides my mom; this was just too much for me.



   "I can't!" I quaked fearfully.



   "Yes you can, just lick your lips and suc-k on it like it was your baby bottle," she said impatiently.



   John's coc-k stood proudly before me, huge in every respect. The head was reddish-purple and the shaft, which looked like it would take both my hands to span, was thick and covered with veins. It was so different from my own little pecker that was maybe two and a half inches when hard. This one was like a baseball bat!



   "Oh...I don't think...I mean-I," I whimpered pathetically.



   Without waiting, John simply rammed it into my mouth, shoving it all the way in until I gagged. I squealed with the meaty invasion and he pulled it out only enough to allow me catch my breath. Grasping my head, he guided me up and down until he had established a rhythm for me. Obediently, I kept it up, not knowing what else to do and before long, I was using my tongue to lick the sensitive underside of his coc-k. It tasted slightly salty and I smelled his musky cologne from his crotch. In order for me to keep my balance, I found it necessary to grab his thighs, and when I did, it was a lot easier to steady myself. By now, I was slobbering pretty good and his massive coc-k was filling my mouth completely, stretching my cheeks to accommodate him.



   After five minutes of steady pumping, I felt his thighs tense up and I knew he was about to c-um. I figured he'd pull it out and blow his wad on the floor but instead, he held my head tighter, forcing his coc-k deep into my throat. I felt his already gigantic phallus swell in my mouth and then suddenly, with a roar of satisfaction, he exploded, pouring a huge quantity of warm, creamy semen into my mouth and making me gag. Reflexively, I swallowed his load but more just kept coming out. I swallowed again, the salty taste of his c-um all over my mouth and I wanted desperately for him to remove his coc-k but he just held it there and continued to fill my mouth with c-um. I couldn't believe how much he had and I lost track of how many times I swallowed his load before he at last pulled his still erect member from my lips.  



   I was still in a daze as I gasped for air and semen dribbled down my chin. Dixie quickly grabbed one of my pacifiers out of the diaper bag, wiped the c-um off my chin with it, and popped it back in my mouth. My jaw was sore from being stretched open so far and a slick coating still covered the inside of my mouth.



   I had never been so humiliated in all my life. Tears of shame filled my eyes and I kept them downcast, unable to face the girl that I had formally held such high aspirations for. I had been in denial for the last year, thinking there might still be hope that she would be interested in me but now those hopes were dashed. Here, I had waited all my life for my first sexual experience, always assuming it would be with a girl, and I ended up down on my knees, suc-king the coc-k of a big football stud and then swallowing all his c-um. Even if by some miracle, my mommy ever decided to potty train me, there was no way I'd ever be able to show my face at my old high school again. I'd be known as the sissy coc-k suc-ker, unworthy of a girl.



   Tears of frustration trickled down my face and I chewed on the c-um covered pacifier, angry with the unfairness of life.

[Anonymous]

Dixie ignored my pouting and kissed John amorously, rubbing his big, hairy chest with her long nails.



   "How did that feel, Lover?" she purred.



   "That was great. He did a good job of swallowing too--most virgin coc-k suc-kers gag and choke but he licked up every drop."



   "Well, if you liked that, I'll have to make sure I bring him over more often," she said with a smile, "wouldn't that be fun, Bobby?"



   I said nothing as I stared at the floor and pouted.



   "Looks like it's time for his nap. Whenever he starts to sulk, it's a good time to put him in his crib," Dixie told him, "we better get going."



   They said their goodbyes and she led me back out to her car. This time, I was totally oblivious to what people would think if they saw me. I don't even know if I was being stared at as I waited to be let in but before long, we were driving over to her house. Once we got there, she led me inside and instructed me to keep the pacifier in my mouth, or I'd be sorry.



   I had assumed the house would be empty but instead her mom and two younger sisters were there. They stopped us in the living room and seemed to be enjoying themselves, making humiliating comments to me.



   "Those are thick diapers you're wearing little sissy boy. Is it because you wet a lot?" one of the younger ones asked.



   "Yes he does, Rachael. Look, see these little snaps below the hem of his sailor suit? They're to keep his diapers up when they get wet and heavy," Dixie explained to them.



   I blushed a beet red as they all giggled.



   "Dixie, you better check your little boy now, he looks like he may have wet himself on the way over," her mom suggested.



   Amidst much scrutiny and laughter, Dixie undid the three snaps across the front of my crotch, allowing the stretchy fabric to bounce upward, exposing the nursery print plastic panties for all to see. In my agitated state, I emptied the rest of my bladder in front of everyone, the undeniable hissing sound, impossible to miss.



   Rachael pointed at my diapers and covered her mouth as she laughed, "look, he's wetting himself right now!"



   The others joined her and I tried to pull away but Dixie's hold on my wrist prevented me. I whimpered with embarrassment as I suc-ked on my pacifier and stomped my feet in frustration.



   "Aww, looks like the little sissy wants his diapers changed," the other sister said, "do you have his change in his diaper bag?"



   "Yeah, c'mon, we can do it on the kitchen floor," Dixie told them as she led me to the area covered with polished wood. Pushing me down on my wet bottom, Dixie began taking out the contents of my diaper bag. Her mom scooped up the baby bottle and rushed to fill it with milk, setting it in the microwave to warm it.



   Dixie pulled my clinging wet panties down and off my feet while I looked away, unable to return the looks of her sisters.



   "Wait'll I tell everyone about this!" Rachael gushed excitedly, "They're not gonna believe it!"



   I knew that in a day, the entire school would know all about my sissy clothes and diapers and I moaned in despair.



   Dixie unpinned the sopping wet cloth and rolled it in a ball, stashing it in a plastic bag included for that purpose. As she wiped off my genital area with some baby wipes, her mom returned with the bottle of warmed milk which she replaced my pacifier with. I welcomed the change to try and get rid of the flavor of John's c-um that was still in my mouth.



   Once again, I was the recipient of more giggles and comments about the diminutive size of my pen-is, causing me yet more anguish.



   "Oh my god! He's as small as Mrs. Sheppard's little boy who's still in training pants!"



   "No wonder he never got any girls--who would want to have anything to do with that tiny thing!"



   I suc-ked desperately on my bottle to hide my shame as Dixie placed a fresh diaper underneath my bottom. Drawing the thick but soft cloth between my legs, she gave me another dusting of baby powder before pinning the sides securely in place.



   "Let me put his panties on," Rachael insisted.



   Holding the pink plastic waterproof panties open, she waited for me to get up and place my feet through the leg openings. She slapped my hands away as I tried to pull them up myself, instead forcing me to endure the slow and humiliating process as she raised them up my skinny legs to my crotch. Together, Dixie and Rachael wrestled the panties over the thick mass of cloth, tugging on the waistband all around until the diapers were completely sealed. As she tucked in several stray bits of cloth into the leg holes of the snug panties, she slapped my diapered bottom.



   "There, all ready for naptime."



   Unsnapping my crumpled shorts, she pulled them down my legs, leaving me in my sailor suit with my pink plastic panties exposed.



   "Come on Sissy," she said as she led me down the hallway and into her bedroom. After tucking me in, she handed me an old stuffed animal and pulled the covers up, taking the empty baby bottle and replacing it with my pacifier.



   "Just imagine this is John's coc-k," she said wickedly, "that should soothe you."



   I fell into a fitful sleep, dreaming of big coc-ks in my mouth and creamy c-um that I struggled to swallow.

[Anonymous]

For the next several weeks, I made regular trips to John's house with Dixie, dressed in my best sissy finery while I was made to suc-k him dry. I soon became quite an accomplished coc-k suc-ker and I learned the best technique to get him off in as little time as possible. This prevented my jaw from getting so sore which was why I tried so hard but it had an unintended effect. Dixie thought it was a shame to let my talents go to waste so she invited over several other members of the football team. After the initial mocking comments and taunts about what a pathetic sissy I was, they made me get on my knees and suc-k each of their massive coc-ks. Dixie watched carefully to ensure I swallowed their entire load and licked every drop of c-um from their shafts before moving on to the next one.    



    Dixie said I made such a natural coc-k suc-ker that she replaced my usual pacifier with one that had been made from a dil-do. It had the handle like a pacifier but the teat had been replaced by three inches of thick rubber coc-k and I was made to suc-k on it whenever I was out of the house.



   Word quickly spread around school about me and my jaws were kept sore from the never ending procession of men stopping by to get a blow job.



   On one occasion, five guys showed up, and I finally said that enough was enough. There was just no way I was going to suc-k that many coc-ks, I petulantly told Dixie, in my shrill, raised voice. She responded by yanking my rumba panties down (I was wearing a lemon yellow chiffon dress with matching ruffled panties) along with my plastic panties and diapers and administered a blistering spanking. After reducing me to a bawling crybaby, she made me apologize to the first man. He took me over his lap and proceeded to give me another series of stinging slaps with the paddle before lifting me off and setting me before him, on my knees. As I cried my eyes out and rubbed my blazing bottom, he undid his pants and pulled them down with his underwear, exposing a raging hard-on that glistened with pre-c-um. Now thoroughly chastened, I dutifully bent between his legs and went to work on his magnificent coc-k, bobbing up and down as the tears streamed down my face.



   I swirled my tongue around his head and fondled his balls with my free hand, tantalizing his senses. suc-king and slurping, I had him moaning in ecstasy in short order. I had learned to recognize the signs when a man's about to c-um in my mouth and this guy was no different. I was bobbing up and down rhythmically, when I felt his body tense up in front of me. Suddenly, as my pink lipstick coated lips were encircling his gigantic shaft, he pumped load after load into my mouth, filling it to overflowing until I swallowed it all down obediently.



   After I had lovingly licked every inch of his shaft of c-um, I was pulled away by the next guy. He wasted no time in putting me over his lap as well and giving me another session with the paddle. My fanny was already cherry red and I begged him pathetically not to spank me. He only laughed and proceeded to paddle me for all he was worth. When he had finished, I lay gasping over his lap and he gently held me up, placing me back on my knees. A moment later, I was slobbering on his coc-k, doing my best to coax his mighty member into orgasm.  



   I didn't have long to wait. He shoved his huge pole into my mouth with hard, hammering thrusts and soon he was filling it with shot after shot of hot, salty c-um. I swallowed it all down only to find myself being put into position over the next man's lap.



   I begged and pleaded desperately to be able to suc-k his coc-k but he only ignored me and after accepting the wooden paddle, gave me ten of his best and hardest.



   This pattern continued without pause until I had suc-ked everyone of them dry and I sat blubbering on the floor, c-um dribbling down my chin and my panties a tangle around my ankles. Dixie re-diapered me and pulled my panties back into place which only sealed in the inferno raging on my bottom. One by one, the men left, thanking Dixie for a great time and making plans to do it again. She was only too happy to accommodate them and when they had left, she turned to me and said, "There, maybe that'll teach you not to disobey me again."



   I sniffled and nodded my head submissively, "Yes, Ms. Dixie."



   "Your sissy training is going well but there's still one more step for you to take," she said mysteriously.



   I couldn't guess what that would be but I was to find out a week later.