Once a Sissy, Always a Sissy

[Anonymous]

   Several days later, I was still horny and frustrated, with no outlet for my sexual desires. I was so horny, I was ready to cry! I was desperate to get into Vanessa's bedroom so I could masturbate to her picture and finally, on Saturday, I got my chance. I knew my window of opportunity would be limited so I wasted no time in doing my deed. In less than a minute, I had stroked myself to an earth shattering climax, only to have Barbie walk in on me just after I'd finished. I was still breathing a little hard but vastly relieved she hadn't caught me.

   However, she looked at me strangely and then walked out again. Consumed with guilt, I went out after her, only to find her whispering in her bedroom to Vanessa. When I walked in, the latter told me to come over to her. Today, she was wearing a short skirt with a slit up the sides, her chrome high heeled sandals, and a strapless top that pushed her huge bosom up into two wonderful globes.

   Once again, my heart rate shot up wildly and I hoped there was no sign on my face as to what I'd just done.

   "I want to check your diapers," Vanessa told me straight out.

   I racked my mind for some reason to stall her but I couldn't think of anything. In my panic, I tried to force myself to pee and cover up the evidence of my misdeeds but of all times, nothing would come!

   "But why?" I asked innocently, "I'm not wet or anything."

   "Come here, Jimmy," she commanded me, her voice taking hold of me with its iron grip.

   "B-but, why?" I stammered, even as I edged closer to her.
   Without explaining herself, she reached forward and yanked me closer to her, making me cry out in fear.
   "Oh!" I exclaimed.

   With her long, manicured nails, Vanessa tugged down on my lilac colored plastic panties, lowering them to the level of my calves. My knees suddenly went weak as I looked up to see Barbie staring hard at me, her ravishing green eyes drilling into me accusingly.

   Vanessa unpinned one side of my diapers and folded it down, revealing the gooey, sticky c-um from my masturbatory misadventures. She took one disgusted look at it before looking up at me, fixing me with her withering stare.

   "Barbie, would you be so kind as to fetch the paddle from Jimmy's room?"

   I immediately began fidgeting in front of Vanessa, the threat of a spanking weighing heavily on me.

   "I-I didn't mean it," I offered lamely, hoping somehow that would make it better.

   "You are going to get a good, hard spanking, Jimmy," she said as she looked me in the eye, "and then, there are going to be some changes around here for you."

   My heart skipped a beat as I imagined what those would be.

   "You are a naughty little boy who needs to have his bottom paddled. And after that, I'm going to give you a nice, hot, soapy enema," she said as she looked deep into my eyes.

   I quivered with fear and my little sphincter puckered in anticipation of it's upcoming punishment.

   "Oh no! I promise I'll be good!" I squealed.

   At that moment, Barbie returned with the wooden paddle in her hand and a big smile on her face.

   "I'm going to enjoy watching you cry like a baby,"she said smugly.

   I whimpered in terror as Vanessa pulled me over her lap, the gooey c-um in my diaper pressing against me as if to mock my recent orgasm.

   "No-no-please no!" I whimpered, "please don't spank me, please!"

   Vanessa ignored me as she rubbed my bottom with the face of the paddle.

   "Aww...are you going to give us a big sissy cry now, Jimmy?" she asked demeaningly.

   As if to confirm what she was saying, crocodile tears spilled out of my eyes and I squirmed as she removed the other pin from my diapers, revealing my bottom for the spanking it so badly needed.

   "Mommy," I whimpered weakly.

[Anonymous]

   The spanking that followed was long, painful, and humiliating, and it left me bawling like a three year old girl who'd had her doll taken away from her and ripped apart. Vanessa paddled my bottom into a flaming hot, cherry red and every square inch stung like bees were attacking me.



   As I lay over her lap, sobbing and trying to regain my breath, Barbie brought over a big, red rubber enema bag that she'd filled to bursting with hot, soapy water. I could see the suds and bubbles where the cap sealed the container and beads of water glistened from its bulging sides. She hung it from a hook on the wall and uncoiled the long white tube that was connected to the bag. At the opposite end, was a large rubber dil-do that had a hole in the end where the water would soon be flowing out of. I gulped in fear as she swirled the thick phallus in a jar of nursery scented vasoline, coating it with a thick layer of the lubricant.



   "No...no...no," I begged weakly, as I tried to wipe the tears from my eyes.



   Vanessa ignored me as she stuck her fingers in the vasoline and then brought them up to my anus, coating it well and pushing inside the rest as she pulled my reddened cheeks apart.



   "I want my mommy," I whined as I squirmed over her lap.



   Taking the fat dil-do in her right hand, Vanessa brought it up to my hole while the other hand kept my cheeks spread. With resolute determination, she began pressing it firmly against my sphincter, refusing to let me squirm away from it.



   "Relax, Jimmy," she said softly, "it'll go in a lot easier if you just relax."



   "Oh!" I squealed, "it's too big! I can't take it!"



   Vanessa kept up the pressure, bearing the fat, slippery dil-do against my hole while she worked with my stinging cheeks to open them up wider.  



   "No! Please...it's...it's too...big...oh!...I can't--"



   All of a sudden, that fat head of the dil-do slipped past my rim and Vanessa smiled with satisfaction  as she pushed the rest of it slowly inside me.



   "Ohhhhh!" I moaned.



   "That's  a good little boy," she commended me, "that's my little sissy."



   She twirled it around slowly and began pumping it in and out as I moaned helplessly. I knew I sounded like a little girl but I couldn't stop myself.



   "This is just what a sissy needs," she assured me as she continued to pump me with the slippery dil-do, "and it's something you can look forward to from now on, every morning."



   "Ohh..." I moaned in distress.



   I felt the pumping motion stop and Vanessa's hand went to release the clip. With a suddenness I wasn't prepared for, the hot soapy water surged into my rectum and I cried out in surprise.



   "Oh! Oh! OHH!!"



   "There, there, Sissy. We're going to get you all squeaky clean today," Vanessa told me.



   The water flowed into me with great force and I soon found myself in the throes of strong cramps. I tried desperately to pinch my stinging cheeks together in the hopes of cutting off the flow but it was hopeless. The fat rubber dil-do was buried deep into my rear and the soapy water continued unabated.



   I was panting heavily when she finally snapped the clip closed, allowing the first flow to work it's way deep into my bowels. While she waited, she teased me with the slippery dil-do, twisting it around and pushing it further in.



   "I hope you enjoyed yourself today, Jimmy. Because that was the last time you'll ever come in this house," she informed me.



   I bit my lip anxiously as I wondered exactly what she meant by that although at the moment, I was pretty well occupied with the water churning around inside me.



   "How many times have you masturbated since you got here, Jimmy?" she asked as she pushed the dil-do in deeply, making me moan in reponse.



   "Um-uh...just f-four times," I admitted.



   "And did you always use that picture of me in the swimsuit?"



   How had she known about that? And I thought I had been so sly!



   With a thick dil-do buried in my bottom and more soapy water waiting to fill me up, I couldn't hold back the truth.



   "Y-yes, Ma'am," I replied meakly.



   Vanessa smiled as she released the clip and the water flowed once again into my pouting bottom.



   "Ohhhh!" I moaned.



   "Well, I'm going to put a stop to that from now on," she told me.



   Beads of sweat appeared on my brow but tears filled my eyes as I saw my one chance for relief being taken away. I wasn't sure how she would do it but I was certain she'd find a way.



   Meanwhile the pressure continued to build inside of me and I felt like I was ready to explode. Vanessa squeezed the clip shut again and I lay there, panting over her lap, the cramps painful as the soapy water filled me up. I squirmed helplessly for several moments until she released it again. I cried softly until the last of the water flowed into me, gurgling with finality. I heard the bubbles disappearing into my rectum announcing the end of the enema and, after waiting an infuriatingly long time, she slowly removed the fat, imposing dil-do from my anus.



   "Ohh!" I exclaimed as it slid out of me.



   "Go into the bathroom now and release that. And I better not find one drop on the floor or you'll be going right back over my lap again. Do you understand?"



   "Yes, Ma'am," I replied obediently.



   I limped weakly to the bathroom and practically fell on the toilet as I released all the pent up liquid. My cheeks stung bitterly where they contacted the seat but the relief from releasing the enema made up for it. Several times during the next ten minutes, I stood up thinking I was finished, only to feel another wave of liquid waiting to get out.



   At last, I had completely expelled the enema, and slowly I made my way back to my room.



   Barbie saw me out in the hallway, and she called me down to her.



   "In here, Jimmy. This is your new room," she said with a smile.



   Butterflies filled my stomach as I walked slowly and hesitantly toward the room that had remained locked up and hidden from me for the last couple of weeks. When I turned the corner, Vanessa was waiting inside, a cool smile upon her pretty face.    The room was made up like a little girl's nursery, with the walls decorated with cartoon characters and frilly pink curtains on the windows. A big wooden baby crib dominated the room, painted in pink and I could see the waterproof sheet on its mattress, all ready for me. To its right was a raised changing table with more nursery print vinyl stretching over its shiny surface. Underneath lay stacks of diapers and in a shelf beside it were a wide selection of plastic and rubber panties. A pink dresser with bunnies on it was to the right of that and in the open closet, I could see dresses and baby clothes of every type imaginable. Lastly, a mesh walled playpen was off to the left side, its floor containing numerous baby toys.



   My mouth dropped open in shock as I took all this in.



   "From now on, this is where you'll live," Vanessa said firmly, "you'll start each day with a hot, soapy enema and then we'll dress you for the day like the sissy that you've been acting like."



   As I stood in silence, listening to her lay down the law, I held my hands over my privates since by now, I was only wearing my sneakers and a t-shirt.



   "It's obvious that you can't be trusted wth adult privelages so I'm taking those away. From now on, you'll be treated like a helpless little baby girl, who has no control and wets her diapers like any infant."



   Vanessa took me by the wrist and sat me down on the changing table as she began gathering a stack of diapers for me. Tears were trickling down my face as I looked around my new surroundings and then back at her.



   "I don't wanna be a baby!" I sobbed as I bunched my hands into fists.



   Vanessa took a big pink pacifier that hung from a loop and stuffed it in between my quivering lips, passing the loop over my head.



   "There. That will be your constant companion from now on. If I ever catch you without it, I'll paddle your little bottom--do you understand?"



   I nodded tearfully as I nursed on the fat rubber nipple in my mouth.



   She tucked my diapers underneath me and proceeded to coat my crimson bottom with diaper rash ointment as she continued to scold me.



   "Jimmy. Just look at you. You're an immature little sissy who simply refuses to grow up. You belong in diapers so that's exactly where you'll stay."



   A cloud of baby powder rose around me as she sprinkled the front of me with it.



   "And I want everyone who comes over, to see you as you really are, a diaper wetting panty-waist, trapped in the body of a man."



   She pinned my diapers closed securely and I sobbed in shame. Reached over, she picked out a pair of pink, nursery print plastic panties and quickly snaked them up my legs, fitting them over my bulky diaper with a bit of a struggle. With my bottom sealed up again within my waterproof panties, the stinging on my cheeks was increased measurably and I squirmed on the changing table in discomfort.



   Standing up, Vanessa went to the closet where she returned with a pair of glossy black mary janes, their buckles, a shiny silver chrome. Untying my sneakers, she removed them along with my socks and threw both sets in the trash.



   "What are you doing with my shoes?" I cried incredulously as the pacifier fell out of my mouth.



   "These, are your new shoes," she said as she held up the childish mary janes to me. I pouted as she stuffed the pacifier back in my mouth and pulled a pair of pink and white lace anklets over my feet. After that, she put the shiny black shoes over my feet and buckled them in place. I felt so sissyish as I looked down at the babyish shoes, with the lacey edges of my socks encircling my ankles.



   Returning to the closet, she picked out a puffy petticoat with multiple white layers, each, softly ruffled so that it formed a flared out hem at the bottom. Taking my t-shirt off, she threw it in the trash as well and I squealed in protest through my pacifier. Ignoring me, she lowered the frilly confection over my head and adjusted the thin shoulder straps, making sure the layers of the petticoat fell evenly. Standing up again, she browsed the well stocked closet until she pulled out a lacey pink party dress, with short, puffy sleeves and white lace highlights all over it. I shuddered as I noted the short ruffled hem. Pulling it over my head she turned me around to button it up in back. All the while, I was whimpering through my pacifier while Barbie smiled down on me, smugly satisified with how things were progressing.



   "Stand up, Sissy," Vanessa ordered me curtly.



   Sniffling to myself, I stood up on my babyish shoes and looked for the first time at the huge mirror that was covering the opposite wall. Looking back at me was an insecure little girl, pacifier in her mouth, her diapers and pink plastic panties plainly visible under the multiple ruffles of her party dress. Except that the little girl was me! Turning slightly, I noticed that the thick diapers gave my bottom a fat, round profile that only enhanced my infant look. I blushed deeply as I gazed at the reflection and it occured to me that I made a very natural looking baby girl, especially with my soft, feminine legs.



   "Since you obviously still need your mommy, I will fulfill that role," Vanessa explained, "from now on, you will address me as 'mommy'. Do you understand?"



   "Yes Mommy," I replied submissively.



   "The bathroom is now off limits to you. Since you can't seem to control your peeing anyway, you can just use your diapers like every other little baby."



   "Yes Mommy," I repeated.



   Barbie led me over to a vanity and she began methodically putting small curlers in my hair, adding a foul smelling permenant solution before sealing each curl in place. I was angry and frustrated about the process but there was nothing I could do about it. It was still painful to sit down, even on the padded seat, and I sure didn't want another session with Vanessa's paddle.



   While Barbie was attending to my hair, Vanessa busied herself by painting my nails a glossy, bubble gum pink, which gave my hands a distinctively sissyish look. I could only chew on my pacifier and pout as these two beautiful women transformed me into a prissy, sassy, sissy baby girl.



   A half hour later, they were done, and they had me go out of the room and wait for the solution in my hair to take effect. Two boring hours later, they took out the curlers and fluffed my hair out. Peals of laughter ensued as the women snickered at me and my new Shirley Temple hair-do.



   Barbie practically dragged me back into my new nursery so I could see the whole effect in the full length wall mirror. I blushed a deep shade of red as I witnessed in total, the full effect of my sissy transformation. I held the ruffled hem of my satiny party dress daintily with my pink tipped fingers as I realized my nursery print plastic panties were in full view below. My glossy mary janes gave me a childish look but the pacifier still in my mouth, along with my thick diapers, verified what I really was--nothing but a big baby.



   Tears filled my eyes as Barbie led me over to my new playpen, sitting me inside with strict instructions not to get out unless I wanted another spanking. As I stared over the padded rail, I gazed at my babyish reflection and softly cried to myself. I stopped only momentarily as I felt the front of my diapers growing wet and warm. I was wetting myself without control again and I burst into sobs befitting my appearance.

[Anonymous]

The next day, Vanessa strode into my nursery with Barbie, a ravishing smile on her face. In her hand was a small plastic bag with something I couldn't identify within it.



   "It's finally arrived!" she exclaimed as she dug her long nailed fingers into the clear manufacturer's bag, "and just in time for your birthday."   



    She pulled out a strange looking item that I didn't recognize, a series of loops made from a type of soft braided cord.



   "Barbie, be a dear and take his diapers down will you?" she asked her maid.



   Barbie strode forward and pulled me out of my playpen, leading me toward the changing table where she sat me down, smiling wickedly at me as she did so. I had no idea what was up so I lay back and let her pull my plastic panties down, revealing my semi-wet diapers underneath. When she unpinned the cloth, Vanessa bent over and began positioning the loops of cord around my scrotum and pen-is. I looked down naively, not knowing what it was she was doing, as her smooth hands fiddled and adjusted the loops, securing them and cinching up them snugly.



   "I had to get the smallest one they made, but even that was too big," she explained to Barbie who watched with great fascination, "the man even asked me if this was for a little boy but I told him, no, just an immature little man."



   Barbie giggled and asked, "so how did you find one small enough?"



   The nice man said he'd custom make one for me," Vanessa told her, "he said anyone with such a tiny pen-is probably didn't have any use for it anyway."



   On closer examination, I saw that one loop encircled my sack, another went around the base of my wee-wee, while another encircled it just a bit higher. They were all interconnected by a section of the cord.

 

   Vanessa continued to adjust the device while I stood in helpless apprehension. I felt her cinching the loops tighter until they were snug, but not uncomfortably so.  I wanted to stop her and stand up for myself but how? She'd just yank me over her lap and spank the daylights out of me.



   Finally, she stood up and looked down on me to observe the results of her work.



   ''There,'' she said, clearly satisfied, ''now for the true test.''



   I stared down at my tiny pecker, now securely bound within the three loops of this device and I was seized with panic. The cord wrapped around my balls made it stick out slightly, now that it was encircled like a tie around a bag of candy and the ones around my shaft looked snug and secure.



   "Okay Jimmy, let's see you take it off,'' Vanessa challenged me.



   With the desperation brought on by the realization that I might never be able to play with myself, ever again, I clawed frantically at the corded loops, trying to tear the contraption off me. The material didn't stretch in the slightest and despite its smooth feel, it had the strength of steel. Pulling mightily, the loops dug painfully into my balls and weiner as I tried to rip the thing off me. I gasped in pain and was forced to let go because of the agony I was inflicting on myself. Stamping my feet in frustration, I stormed about my nursery in a tantrum more like a five year old, than the adult I thought I was.



   Barbie clapped her hands together and laughed with glee at my predicament. Vanessa smiled down at me with smug satisfaction while I made repeated attempts to prize even a part of my organ out of the device. At last, I gave up and slumped onto the edge of my crib in defeat.



   "It's not fair!'' I sobbed, ''it's not fair!''



   "Jimmy,'' Vanessa said suddenly in a very provacative voice.



   I looked up from my misery to see her gazing at me with a seductive look I'd only seen once before.



   Stepping over to me, she bent over slightly, hands pressed against the tops of her thighs, her immense bre ( " at " ) sts displayed in front of me within the confines of her tight, low cut top.



   "Remember a long time ago when you were a little boy and I invited you for a closer look at my bre ( " at " ) sts?''



   Her voice was soft and sultry with a timbre that was electrifying and as she spoke, her smooth, creamy hands began to caress her big, round cups sensuously. My eyes dropped to stare at what she was doing and I was hypnotized as I watched her stroking her bosom, alternately squeezing and lifting her boobs in a manner that drove me wild with desire. Vanessa was a living goddess with a heavenly body and her sexy game left me panting with excitement.



   My little pee-wee responded immediately but no sooner had it begun to harden, than the restrictive diameter of the loops began to cut into my skin, preventing it from growing any larger. My sensation of sexual arousal quickly turned to unrelenting pain and I jumped up, trying once again to tear the restrictive device off me.



   "Owwww!'' I cried as my weiner battled in futility against its bonds.



   "Take it off,'' I begged her, ''please!''



   Vanessa grinned down at me broadly, like a scientist who'd finally solved a vexing problem.



   "Welcome to the sweet bonds of chastity. That should put an end to your masturbating nonsense, once and for all,'' Vanessa proclaimed firmly as she stood back up straight, her hands on her hips in the classic posture of female authority, "happy birthday, Jimmy!"



   "Serves you right, you big sissy,'' Barbie said, still giggling.



   "And now, it's diaper time, Jimmy!'' Vanessa announced cheerfully.



   My lower lip quivered as I sat there, helpless and frustrated. I was desperately horny with absolutely no means of getting relief, and now entirely subject to the whims of this beautiful, but implacable disciplinarian.



   I sniffed in resignation as Vanessa went about her usual thorough job of putting me in my diapers, the thick sticky layer of diaper rash ointment, baby powder, and soon she was pinning me up for my nap in my triple thick cotton diapers. A glittery pair of pink plastic panties followed and she finished by powdering between my thighs and the vinyl material of my panties.



   "Beddie-bye, Baby,'' Vanessa cooed as she slipped a full bottle of warm formula between my lips and began removing my mary janes. I drank the foul, tepid liquid submissively, still trying to grasp the enormity of the catastrophe that had befallen me. As Vanessa tucked my feet under the pink blankets of my crib, I think she sensed my misery.



   Bending over me, she shifted my plastic pantied bottom across the crinkly waterproof sheet covering my mattress which in only a week's time, had taken on the smell of stale pee.



   "Don't you worry, Honey,'' Vanessa said soothingly as she held the big bottle to my lips, ''I'll take care of those little balls of yours before they get too blue.''



   Barbie giggled as if she were sharing a secret joke with Vanessa.



    I wondered just what that might be as I drifted off to a troubled sissy sleep.

[Anonymous]

A week later, I had the opportunity to find out what she had in mind.



   It was a Saturday afternoon and I lay awake in to my crib, still trying to get used to my freshly wet diapers from my afternoon nap. By now they were cool and clammy and they hugged my damp skin within the confines of my snug plastic panties.



   It was also my birthday, and Vanessa had promised me we'd celebrate it in style. I was eager and hopeful that maybe today, of all days, she'd release me from my chastity for a brief, if fleeting, moment of pleasure.



   My heart quickened as I heard the high pitched clicking of her high heels coming down the hall toward my room. I could tell by now who it was by the sound they made since both women had a distinctive stride. In this case, it proved to be both, and my suspicions were confirmed by the whispering I heard as they approached my door.



   Vanessa came into the nursery, followed by Barbie, and she came across the room, unlatching the side bars of my baby crib. She was wearing a light green halter top, whose thin material stretched across her tremendous bre ( " at " ) sts tightly, leaving the entire curvy surface wrinkle free. I noticed her nipples poking out slightly and I could make out clearly, the outlines of her demi cup push-up bra. I prayed silently that she'd let me suc-kle once more from those magnificent, mouth watering mammaries.



   Her small top left her firm, flat tummy exposed and below that, she wore a small pair of bun hugging white shorts.



   Barbie, of course, was dressed in her obligatory french maid uniform, which was no less exciting.



   I had to make a conscious effort now to restrain my pen-is which wanted desperately to react to this display of unbridled sexuality. To do otherwise was to invite a quick and painful reaction from my chastity device, which knew no mercy for my needs. I found the best thing to do was to think of other, non-sexual thoughts to try and distract myself and submissively bow to the reality that there was absolutely no way for me to relieve myself.



   Vanessa pulled down my baby blankets, exposing my bare legs and bulging diapers. My pink nighty had worked its way up around my waist, leaving the colorful nursery print on my plastic panties exposed.



   Instead of moving me to my changing pad as she usually did, Vanessa began peeling down my clinging vinyl panties there on the mattress, tossing them into the large diaper pail I had next to the bed. Even though it was emptied daily, my diaper pail added considerably, its pungent aroma of wet diapers to those of vinyl, rubber, and baby powder that normally permeated the nursery.



   As usual, my diapers were soaked from my nap and Vanessa surprised me by humming an agreeable tune as she unpinned them. As she began cleaning my bottom and crotch, she didn't immediately get another stack of diapers for me. Instead, she began the detailed proceedure for removing my chastity device, and after several minutes of work, my weiner was at last free. I sighed with relief and my excitement increased exponentially as she cleaned it with baby wipes and then put it aside.



   Vanessa pulled back the baby blankets, exposing my nursery print mattress cover and instructed me get on my knees, facing away from her as I braced myself against the opposite side of the crib rail. I could only speculate what she had in mind for me but I knew it wasn't a spanking or an enema. I was also made hopeful by her obvious good mood and I was sure she had something pleasant in store for my birthday.

   "Now, I want you to be a good little boy and keep your hands on the crib rail. Can you do that for mommy?'' she asked sweetly.



   "Yes, Mommy,'' I replied, trying to reign in my excitement.



   "It's very important Jimmy. I'm afraid if I catch you taking them off, I'll have to give you a spanking," she warned me.



   "I'll be good, Mommy" I said hopefully.



   Looking over my shoulder, my bare bottom sticking out behind me, I craned my head to see what she was doing.



   She appeared to be dipping something into the jar of nursery jelly but I couldn't see clearly.



   A moment later, I felt her prying my bottom cheeks apart with her fingers while she began coaxing something smooth and plyable into my anus.



   "Ohh!'' I squealed in surprise as I wiggled my fanny around.



   "Stay still, or mommy spanks,'' Vanessa warned me again, but her voice didn't carry its usual threatening edge.



   I settled down and the object slide in without too much difficulty. It was much smaller than the dil-do nozzle she used with my morning enemas and didn't stretch my sphincter to the limits.



   As she moved it slowly in and out to find the right position, I moaned deliriously, the waves of pleasure washing over me. In a matter of seconds, I was panting hard and Vanessa stopped for a minute to allow me to cool down. My little weiner was rigid and begging for relief as it pointed downwards like the udder of a cow. Breathing heavily, I wanted so badly to reach down and give myself the relief I desperately needed but I kept my hands where they were, clutching the pink upper rail of the crib until my knuckles turned white.



   When my wee-wee finally went soft again, a drop of pre-c-um had appeared at its head and it slowly began to drool down towards the vinyl crib sheet.



   "Okay, get ready with the cup,'' Vanessa told Barbie, who was standing by with a shallow glass in her hands. I had no idea what her purpose was in all this but I quickly forgot about it as Vanessa began her ministrations in back again. I moaned deeply and pushed my bottom against her, trying to take the soft dil-do as far in as it would go. She teased me mercilessly, never allowing me the satisfaction of feeling it deep inside my rectum, where I craved the sense of fullness. My pen-is was rock hard again and my breathing came in short gasps when Vanessa abruptly stopped again.



   Sticking straight down, my pee pee twitched and flexed, frantically seeking release. Vanessa was patient however, and she stopped and waited for the inevitable to happen. Without further stimulation to sustain it, eventually my weiner began to shrink back to its usual limp length of an inch.



   "Try it now,'' Vanessa said to Barbie.



   With a devious smile on her pretty face, Barbie bent forward and grasped my pen-is, pulling downward like she was milking a cow.



   "Oh!'' I squealed as I felt her handling it as if it were a tube of toothpaste she was trying to extract the last bit out of.



   Her efforts were rewarded by a small, gooey string of c-um that dribbled out of the tip, to collect in the small cup she held underneath.



   I cried out in dismay as she not only deprived me of my joy juices, but also the explosive orgasm that would have accompanied it.



   When no more semen could be extracted, Barbie stopped milking me and Vanessa resumed her slow, deliberate pumping of my anus. Tears of frustration filled my eyes as my weiner responded without regard to my wishes, growing hard again according to the will of Vanessa. Before long, I found myself once more at the brink of a mind shattering orgasm, struggling to bring it about on my own by grinding my hips against Vanessa's hand that controlled the plyable dil-do. She succeeed brilliantly in foiling my efforts, by simply relaxing the pressure whenever I tried to push against her. When I finally gave up in defeat, she'd resume her maddeningly slow massage of my prostrate, prolonging my erection in an unbearable torture of unrequitted pleasure.



   When she finally stopped, my breathing was coming in ragged gasps and my face and neck were flushed.



   "Please Mommy, please!'' I sobbed as the tears of frustration rolled down my cheeks.



   Vanessa smiled sweetly and stroked my bottom gently with her silky soft hands.



   "There, there, Baby,'' she cooed, ''we'll get all that icky c-um out of you, don't you worry.''



   Barbie giggled and bent forward, waiting for my tiny pecker to shrink back down.



   In a frantic attempt to frustrate her efforts, I flexed my pee pee wildly, trying to reach orgasm on my own but it was like trying to catch the moon with a butterfly net. Clutching the crib rail with a death grip, I sobbed as my willy slowly softened and became limp again.



   "Come on, Sissy,'' Barbie said coaxing me with a mocking tone, ''c-um like a big boy.''



   I remained in my position, bent over and helpless as Barbie slowly squeezed more of my seed from my tormented pen-is. She managed to extract another big spoonful until at last, it went dry.



   "My, that was a good one, Jimmy,'' she said like she were commending a three year old on a successful potty attempt.



   "I think that's about as much as you're going to get,'' Vanessa advised sagely.



   Barbie held the small cup in her delicate hands and gazed at the milky colored semen filling the bottom.



   "What a good boy you are, Jimmy,'' she said with feigned sincerity.



   "You see, what we've done here is to remove all that pent up sexual tension, while still denying him any sort of release,'' Vanessa explained as she grasped me by the hips and sat me down on the edge of the crib mattress.



   "Now, as an experiment, to see how effective we were, we'll just see if our little baby has any more get-up-and-go left in him.''



   Vanessa took a bottle of Johnson's baby lotion and squeezed out a small quantity in the palm of her hand. As I sat there whimpering and rubbing the tears from my eyes, she reached down and began slowly rubbing the lotion into my groin. My pee wee was so small, her hand dwarfed its limp form and she softly stoked it, but to no effect.



   "There, you see,'' she said as she pulled her hand away, revealing a well lotioned but nonetheless limp pen-is, ''no effect whatsoever. This sissy has been effectively milked.''



   Barbie burst out laughing, her disdain and lack of sympathy washing over me like icewater.



   It was all too much for me to handle and I burst into tears, crying like a two year old.



   "Awww, there, there, Baby,'' she said as she dipped the pacifier hanging around my neck into the cup containing the spent semen. She coated the big rubber nipple generously and coaxed it between my lips. Like the submissive sissy that I was, I willingly opened my mouth and accepted the creamy covered pacifier.



   "Awww, poor wittle baby,'' she said as she held it in my mouth, forcing me to suc-k and swallow my own c-um.



   "Oh," Vanessa said as an afterthought, "this, is the best way to complete his milking."



   Taking hold of my arm, she pulled me up to an almost standing position and turned me slightly, so that my bottom was exposed to her side. Before I knew what was happening, I felt the searing impact of the paddle on my rear as she swatted me fiercely.



   The pacifier shot out of my mouth as I shot up straight.

   "OWWW!!" I cried in bewildered surprise.



   Barbie burst out laughing and she took the paddle from Vanessa.



   "You mean like this?" she said, her hand swooping down to deliver another stinging swat on my poor tender fanny.



   "OWWW!! Stop it!" I wailed.



   Barely surpressing a giggle, Vanessa took back the paddle.

   "No. Like this," she said as she yanked me over my my left arm and smacking me equally, if not harder than Barbie had.



   "OW-HOW-WOW!!!" I shouted, dancing from one foot to another as my free hand went down to rub my reddening cheeks.



   Barbie was laughing hysterically and she retrieved the paddle back from Vanessa.



   "Oh," she said between fits of laughter, "I thought you meant like this."



   Pulling my hand away that was trying to protect my defenseless bottom, she brought the paddle down hard, right in the center of my cheeks, leaving a bright red oval impression there.



   I howled in pain and stomped my feet as the tears spilled down my face. By now, Vanessa was laughing too hard to continue the game so she sat me back down on the crib mattress as she tried to regain her composure.



   "Sorry, Jimmy," she said still chuckling, "but you have such a cute, spankable ass, sometimes I can't resist it."



   I looked away and wiped the tears out of my eyes, trying desperately to keep a stiff lip through it all.



   "Aw, cheer up Jimmy,'' Vanessa exclaimed still giggling, "now it's time to get you dressed up for your birthday party!''



   She spent the next several minutes getting me secured in my chastity device and when she was satisfied that I was locked in and trussed up, she prepared my diapers for the day. I suc-ked my c-um coated pacifier and sniffled while she slid the stack of soft, thick diapers underneath my rump, humming again to herself.



   Normally, it would have brought about a painful reaction to look down at her big, swaying bre ( " at " ) sts, as she busied herself applying my diaper rash ointment and baby powder, but not now. Now that I had been relieved of my sissy juices, I could stare at her perfectly shaped boobs and not get hard or feel the accompanying pain. I could also allow my eyes to wander over Barbie's immaculate body, savoring her glossy black stilletto heels and her long, sensuous legs. Her thighs were firm and trim and her skirt was oh, so short, threatening to reveal her silky sheer black panties if she bent over. And that's just what she did as went over to get my socks and shoes for today's outfit.



   Even through my anger at her, I looked with longing admiration as she bent over and I saw her cute little bottom, nicely framed by the see-thru black panties stretching over her youthful cheeks. When she came back, she caught me staring at her and she came alongside the crib, the cup still in her hand.



   "Ready for some more?" she asked, as she popped the pacifier out of my mouth and coated it again with the remaining semen. I twisted my face into a grimace of disgust but I obediently opened my mouth to take it back in again, my tongue once more tasting the creamy, somewhat salty sperm and the rubber of the pacifier nipple.



   "How does that taste?" she asked as she bent over, revealing her wonderful cleavage as she did.



   I said nothing but looked away as Vanessa was pulling the thick cloth up and pinning the sides of my diapers securely. She retrieved a pair of white, nursery print, plastic snap-on panties and she guided my feet thru as she pulled them up my legs. Getting to my thighs, she paused for a moment.



   "Up, Sissy," she commanded me.



   I lifted up my rump in compliance as she worked the panties up and around the thick cloth of my diapers.



   Bending over, she once again put her hands on the front of her smooth thighs to talk to me closer.



   "Don't worry Jimmy. Since you've got guests coming over to see you, I won't make you wear a baby dress."



   I mumbled a sound of surprise through my pacifier, somewhat relieved by this unexpected turn of events.



   "Nope. Instead, today you can be mommy's little sailor boy. Doesn't that sound like fun?" she said as if she were addressing a four year old.



   I frowned in disapproval and she brought over a sissyish, baby blue colored satin top, lined with white lace and ruffled at the hem. The chest had a lace lined bib and puffy short sleeves with more lace around the edges. She raised my hands and lowered the softly lined top over my head and arms. In frustration, I tugged at the short hem of the top, hoping against hope it would cover my embarrassing diapers but that was not going to happen.



   "Aww...you're concerned someone's gonna see your big poofy pampers, aren't you," Vanessa said in the most condescending tone of voice as she saw me tugging at the top.



   I nodded my head numbly, unable to look her in the eye.

   "Well I've got just the thing," she said cheerfully.



   Going over to the dresser she dug around until she found what she was looking for. Coming back to the crib, she held a frothy pair of white lacey satin rhumba panties before me, the lace on the seat edged with baby blue.



   "Aren't these just scrumptious?" she exclaimed with a ravishing smile.



   I pouted miserably as she snaked the silky confection up my legs and over the smooth plastic of my waterproof panties. This was followed by a wide brimmed straw hat with a baby blue ribbon around its crown. At the same time, Barbie was rolling knee high socks up my calves and my glossy black mary janes over that. I noted that the socks had a satiny blue ribbon tied into a bow at the top of each sock. I couldn't remember ever feeling like more of a sissy.



   "Stand up Jimmy, so you can see your new outfit," Vanessa said enthusiastically.



   Pulling me up, they stood aside from me so I could see myself clearly in the wall mirror. Gazing at my reflection, I blushed deeply as I imagined what people would say when they saw me in this childish ensemble.  



   As if to confirm my fears, the doorbell suddenly rang.



   "Oh!" I cried out in panic as a small stream of pee accidentally leaked into my fresh diapers.

[Anonymous]

Barbie giggled at my appearance without making ready to answer the door as she normally would have.



   "Jimmy?" Vanessa asked sweetly, "wouldn't you like to answer the doorbell? It's probably one of your party guests."



   I blushed again and bit my lip in angst, then shook my head violently.



   "Now, Jimmy," Vanessa said, her voice taking on an edge, "don't be rude. These nice people have come from a long way and they've brought presents for you. You wouldn't want to leave them waiting would you?"



   I looked up at her helplessly, praying she wouldn't make me go through with this.



   The doorbell rang again, its tone somehow seeming more urgent now.



   Without a word, Vanessa picked up the oval wooden paddle and looked me in the eye.



   "Maybe we need to have a little lesson in manners, hm?" she said, her voice cutting through me like a knife.



   "No Mommy!" I cried frantically as the pacifier fell out my mouth again.



   I bolted out of the room quickly, or at least, as quickly as I could, considering I had to waddle with the thick diapers I was wearing. I tried to shut out the giggling coming from my nursery as I went downstairs and to the front door. My heart was pounding in my chest as my hand went to the door knob. I could see the vague shape of two, slim young women through the glazed side window next to the door but I was frozen in fear. One of them rang the doorbell again and I heard Vanessa's voice behind me at the top of the landing.



   "Open the door, Jimmy," she ordered me in her commanding voice that made my bottom tingle with fear.



   As another small stream of pee leaked into my diaper, I opened the door and stood aside.



   The two women burst into uncontrolled laughter as they took in my sissy outfit and as I stood there blushing, I recognized Brittany from my childhood grade school. After a moment, I realized the other one was Tammy, although both had changed quite a bit. I remembered them as two small girls, at the time, no more than ten, like myself. Now, they were about twenty and I was shocked at how they appeared. Brittany looked like a model, and she wore a fashionable silky dress that showed off her long, sexy legs. Tammy was now a beautiful blonde and she wore a black leather bustier that pushed her considerable bosom up into two fabulous mounds of femininity. As she laughed at me, I almost thought they'd spill out of her top as they jiggled from her mirth.



   "Jimmy!" Brittany finally said when she could stop laughing, "you haven't changed a bit! Still dressing up like a sissy and wearing your big, thick diapers!"



   That comment made them burst into peals of laughter again.



   "Couldn't your mommy ever potty train you?" Tammy asked incredulously.



   I glared at them angrily but remained mute as my face and chest reddened.



   Vanessa came alongside and invited them in, thanking them politely for coming. Evidently, they were old friends and for a moment, I was forgotten as they chatted busily amongst themselves. She took them into the spacious living room and sat them down while Barbie brought them drinks. I endured more of their humiliating comments as Brittany related the numerous times she'd tricked me and gotten me spanked. Vanessa thought it was all a riot and she laughed along with everyone while I sat in silence, chewing my pacifier in frustration. Before long, the doorbell rang again and I was prompted to answer it.



   Going to the door, I opened it up for another shocker. It was Ms. Taylor, my school teacher from the fifth grade! She was ten years older now but still a total knockout, and a classy one at that. She wore a sleek beige skirt and a white sweater that hugged her big bosom in a very form fitting way. As she saw me, she coc-ked her head  little to the side in the cutest way and beamed in recognition of me.



   "Jimmy!" she said as she came in and hugged me close, her large bre ( " at " ) sts pushing against me, "don't you look darling!"



   She didn't seem to be surprised that I was still in diapers, at the age of twenty, and I was a bit put off  by the fact that she obviously hadn't had too much faith that I'd ever grown up. I guess she knew me pretty well, after all. As she hugged me, her hand went down to squeeze the ruffled seat of my diapers, checking to see if I was wet like she were my mother.



   "It's good to see you," she said kindly and she planted a wet kiss on my cheek, leaving her dark red lipstick print for everyone to see.



   In her hands, she carried a box gift wrapped in baby wrapping, with frollicking bears and lambs on its pink paper.



   "I've bought you something very special that I'm sure you'll love," she whispered in my ear.



   I blushed at the thought of that, fearing it was probably a sissy dress of some sort.



   Ms. Taylor came inside and I noticed she was still quite a bit taller than me, particularly in her high heeled sandals. She took a seat on the sofa and Vanessa introduced herself and the others.



   As they were making their aquaintances, the doorbell rang again. Vanessa snapped her fingers at me and I hopped up to go answer it.



   This time it was my old adversary, Melissa and her equally tough friend, Tara. Both looked fantastic and as I stood aside, Melissa swatted my padded bottom hard with her gift, which was long and rectangular shaped.



   "Ha!" she smirked, "looks like it works."



   I rubbed my bottom as they came into the living room to join the others. On the coffee table, the guests had stacked my presents, all wrapped in nursery print gift wrap, making it look more like a baby shower instead of my birthday. I wanted to run away and hide but Vanessa instructed me to turn around to model my pretty rumba panties for everyone. Just when I thought I was going to die of embarassment, the doorbell rang once more.



   I went to answer it and I was surprised to see my aunt Suzie standing before me. She wore a tight wrap around that hugged her delicious bosom, and a pair of short, Daisy Duke cut off shorts.



   "My, my, Jimmy, I guess some little boys just never grow up, do they?" she said as she shook her head at my general appearance.



   "It's not my fault," I tried to explain but she wouldn't have any of it and she dismissed my excuse with the wave of her hand.



   "Jimmy, you might be able to convince someone else that, but I know what a sissy you really are," she told me in no uncertain terms, "I've always known you were a sissy and I'm glad Vanessa decided to put you back into diapers. That's right where you belong."



   I was taken aback by my aunt's blunt appraisal and I stood aside as she walked in with a gift under her arm. When she had taken a seat in the living room, everyone's attention turned to Barbie, who was  bringing in a birthday cake with pink and white frosting. I noted there were only two candles on it and everyone began singing happy birthday to me. I blushed as Vanessa came up behind me to tie a pink baby bib around my neck that said 'Bedwetter's Anonymous' on it. They all laughed at that and she told me to blow out the candles.



   "Jimmy's twenty...going on two," she announced to everyone's amusement.



   After serving everyone a piece, Vanessa spoon fed me my cake, while Barbie brought out a big bottle of warm milk for me to nurse from.



   When all the ladies had finished their cake, Vanessa prompted me to begin opening my presents. Reluctantly, I did as I was told, and the first present turned out to be a pink patent leather sissy purse, with the words 'Little Missy' written on both sides in silver glitter.



   "That'll be perfect for when you're out on the town," Tara said with a disparaging laugh.



   I blushed and put it aside, hoping that little adventure would never come to pass.



   Pushing another big box before me, I felt Vanessa's big bre ( " at " ) sts pressing against my back as she told me to open the next present. With much encouragement and giggles from my guests, I opened the childishly gift-wrapped covered box and found a frothy white baby dress, generously adorned with pink accents and lace throughout. It had a fancy layered petticoat sewn into it and it looked like it was made for a three year old girl except that it was obviously in my size.



   Tara, who was sitting to my right, impatiently shoved her gift in my hands, a lewd smile on her face.



   "This is one you'll always have with you," she said.



   It had a strange feel to it, being about the size of my hand but a little bigger. When I tore off the wrapping, I discovered what looked like a short, fat dil-do displayed in a plastic package, except that the base of it had a large plastic ring, exactly like a baby pacifier. The label on the package said 'Dr. coc-k's Baby Pacifier' and it showed a young woman wearing a bonnet and suc-king on the product with an innocent look on her cute face.



   I blushed as I imagined myself using such a thing but Tara wasted no time in grabbing it out of my hands and tearing open the package. She brought the big fat dil-do up to my lips, pressing it against my face forcibly but I kept my mouth petulantly shut. Seeing my resistance, she slapped my bare thigh painfully which caused me to yelp out in distress and she responded by jamming the dil-do in my mouth.

   Everyone burst into laughter at her cleverness and she took the pink plastic loop and dropped it around my neck.



   "There," she said smugly, "guess you know who's boss around here now."



   I suc-ked on the coc-k pacifier in mute humiliation, my cheeks buzzing with shame as I avoided the stares of all the beautiful women present who were witness to my defeat.



   "That is so perfect for you," Melissa said who was sitting to my left, "I always knew you were a coc-ksuc-ker and now everyone else does too."



   I whimpered in embarassment as Ms. Taylor set her gift down before me. She offered me a sympathetic smile and I hoped her present might bring some measure of joy to this otherwise dreadful affair.



   It was lightweight to hold and when I'd removed the giftwrap, I found a white box with tissue inside. Pulling back the tissue, I found three pairs of fancy ruffled rumba panties, in pink, white, and lilac. They featured soft ruffles around the leg holes and big sassy layers of lace across the seat. I looked down at them in disappointment and then up at Ms. Taylor.



   "I thought you might like to wear those for special occasions," she offered sweetly.



   The next present was from Tammy, Brittany's childhood friend and willing accomplice. It was the smallest of all the presents there and it actually felt like two small cyclinders. Opening it up, I found one was a stick of Bonny Bell bubble gum pink lipstick and the other, a small sprayer of perfume labeled 'Nursery Nights'.



   Tara wasted no time in pulling out my pacifier and apply several thick coats of the bright glossy lipstick to my lips, before pushing the pacifier back in.



   "Oh. That's definately you," she said, nodding her head.



   The perfume, she took the liberty of opening and spraying me throughly with. It smelled like baby powder and something else I couldn't quite put my finger on but it reminded me of my nursery and diapers. Even though I was already dressed like a baby, wearing a wet diaper, somehow this scent really brought it home to me and my face went bright red all over again.



   "Now you smell like the sissy that you're dressed up as," she smirked.



   "I know!" Brittany suddenly exclaimed, "why don't we have Jimmy model his new dress and purse for us?"



   "I think that's a wonderful idea," Vanessa said and she reached over and began unbuttoning my sailor suit top.



   I squirmed in protest but soon she was replacing my sissy sailor suit with the frothy white baby dress, lowering it over my head despite my reservations. She buttoned it up securely in back and I noted in frustration that they were purposely put out of my reach. Lowering my silky rhumba panties down my skinny legs, she sifted through the box that Ms. Taylor had given me and selected a pink pair. They were a soft pink color with three large white ruffles crossing the seat and around the legs. At the top, in the front of the panties was a tiny white bow but stitched across the front, in fancy script, it said 'Sissy Jimmy'. I wanted to cry when I read that and Vanessa happily snaked them up my legs, telling me, "you know Jimmy, people in life will judge you by the panties you wear. And these should make it clear just how much of a sissy you are."



   Lastly, she handed me my purse after putting my lipstick in it.



   "There. You're all set. This would be a wonderfull outfit for you to wear out in the park. I'm sure all the little girls would be green with envy," she told me.

[Anonymous]

Everyone laughed at that and Vanessa made me parade around in front them. When I went by Tammy, she insisted on applying some blush to my cheeks, even though I was already several colors of red as it was. Several times, I felt my diapers growing wet and warm, no doubt caused by the trauma I was enduring at these women's hands. I felt like such a babyish sissy, with my swishy white and pink dress, my bulging diapers covered by the pink lacey rhumba panties, my purse and my mary janes. I felt even more infantile due to the fact that my rhumba panties were helping to keep the wet cloth of my diapers pressed snugly against my skin. My shame knew no bounds as the girls took turns patting me on my ruffled bottom and making humiliating comments.



   "There's still one present to open," Melissa said to the crowd, making my heart jump in fear.



   She handed me the present she had been holding on to since she walked in. It was rectangular, about a foot and a half long, by four inches, and about 3/8" thick. I suc-ked on my pacifier nervously as I held this particular gift in my hand, knowing instinctively what it was.



   "Come on, open it," Melissa dared me, a dark smile crossing her face.

   Reluctantly, I ever so slowly tore off the paper and I revealed a polished wooden paddle, with two rows of half inch holes running down the length of it.



   "Well! Jimmy already has one of those that gets a lot of use around this house but now we'll have a choice of styles!" Vanessa stated happily.

   "I say we give the baby his birthday spanking," Melissa suggested impulsively to the group of women.



   "Yes!" Tammy agreed.



   "Excellent!" Brittany seconded.



   "It'll be fun," Ms. Taylor suggested.



   The girls all chorused their agreement until aunt Suzie raised her hand.



   "But wait. I suggest we have Jimmy thank everyone individually and then they can give him his birthday spanks," she offered to everyone's enthusiastic approval, "let's see, he's twenty now and there are one, two, three, four, five, six...seven of us here. That means three spanks apiece."



   Brittany clapped her hands together in glee at the opportunity to spank me again and in a panic, I felt another stream of warm, wet pee go into my diaper.



   Vanessa came over and stood me up, taking the paddle and handing it to aunt Suzie.



   "Now, Jimmy. Thank your aunt Suzie for the pretty white baby dress," she said as she pushed my reluctant form in the direction of my aunt.



   I stumbled forward and pulled the fat pacifier out of my mouth as I stood before my sexy aunt, my pink sissy purse still in my hands. I tried not to be obvious as I gaped at her deep cleavage created by the tight wrap she was wearing but I think she saw me looking.



   "Um, thanks, um, thank you for the, um, d-dress, aunt Suzie," I stammered uncertainly.



   "Well you're most welcome, Sugarplum," she said politely as she pulled my rhumba panties down to reveal my nursery print plastic panties.



   "Jimmy? Have you wet your diapers?" she suddenly said accusingly.



   I bit my lip nervously and looked away at the floor, slowly nodding my head.



   "Looks like your birthday boy's going to need to have his diapers changed," she said to Vanessa as she took me over her lap, "thank god for side snap plastic panties."



   Everyone laughed at that remark except me who was quivering nervously as I clutched my purse, awaiting the first three slaps of the paddle.



   I didn't have long to wait. After pushing up the fluffy hem of my dress, she unsnapped the back of my plastic panties, pushed them back and unpinned my wet diapers. This kept the vinyl of my panties between her thighs and the wet cloth of my diapers.



   SMACKK!! WHAPP!!! SMACKK!!



   Three times, the paddle swooped down, landing squarely on my damp and tender bottom. I gritted my teeth and fought to retain my composure, even as the tears began to fill my eyes. The last thing I wanted to do was to cry like a baby in front of all these women.



   Lifting me back up, she instructed me to hold the front of my diapers and plastic panties in place so that I wouldn't get pee on the next person's lap.



   I waddled nervously over to Tammy, who had taken the paddle from aunt Suzie.



   "Thank you for the lipstick," I mumbled barely audibly as I stood before her.



   With a speed I didn't think possible, Tammy swung the paddle and landed it on my bared fanny with a stinging ferocity.



   WHAACKKK!!!



   "OOWWW!!!" I cried out, jumping up in shock and pain.   



   "What did you say? I couldn't hear you," she said with an evil smile.



   "Tha-thank you for the lipstick and perfume," I said obediently, in a much louder voice, my cheeks smarting badly now.



   "You're welcome, Sissy," she said smugly.



   I took my place over her lap fearfully, slowly getting myself situated with my diaper.



   THWACKK!! SMACKK!! WHAPP!!



   Despite my best intentions, I burst into tears and cried out like a baby, shaking my purse in a sissyish fury.



   I jumped off her lap and carried my wet diapers and panties over to Brittany who quickly took the paddle and yanked me abruptly over her lap.



   "Thank you--"

   My required thanks were cut off by Brittany's impatience to spank me.



   WHACK!!-WHACKK!!-SMACKK!!-WHACK!!



   I bawled openly now, my bottom on fire and I jumped up as the tears rolled down my face.



   "Oops," she said with mock sincerity, "I think I miscounted."

   Giggles filled the room.



    Next was Ms. Taylor and she looked up at me with kindness and compassion.



   "Thank you for the pretty panties, Ms. Taylor," I said between sobs, hoping she'd be easier than the others.



   Gently, she took me over her lap and waited until I had gotten myself and my diaper situated.



   "It's been quite awhile since I've seen your bottom from this perspective, Jimmy," she said as she rubbed my red fanny appreciatively with the long wooden paddle.



   SMACKK!! THWACK!!! WHAPPP!!! SMACKKK!!! CRACKKK!!



   I kicked wildly with my mary janes in pain and frustration as she slapped my already stinging cheeks harshly. Still gripping my purse, I jumped up and looked down at my former teacher who hadn't given me any sympathy at all.



   "Sorry Jimmy. But I didn't want to show you any favoritism," she said in her sweet, innocent voice.



   I wiped the tears away and stumbled over to Vanessa who was waiting patiently for me.



   "Well, little birthday boy. You probably didn't realize it, but you're already wearing my present to you. It's your pen-is prison," she told me.   



   The other girls laughed as she took me over her lap and I kicked even before she began spanking me.



   "Settle down, Jimmy. Or mommy will really give you something to cry about."



   SMACKK!!-THWACKK!!-CRACKKK!!-WHAPPP!!!



   On and on it went, my poor botttom being smacked by everyone present until finally, I reached Melissa. I think I dreaded her most of all because she'd never shown me anything of her personality besides her bullying nature.



   Now as I stood before her, my face wet with tears and my bottom a blazing red, I felt a last surge of fear-induced pee flow into my diapers. It was warm behind my hand and I blushed anew at such a humiliating sensation.



   "Is there something you want to tell me?" she said, coaxing me provacatively in a syrupy tone of voice.



   "Tha-thank you-for-for-giving me, the-the new p-paddle," I said haltingly between sobs.



   "It's my pleasure," she said wickedly taking me over her lap.



   "Please don't spank me hard!" I pleaded to her desperately.



   SMACKKK!!!  CRACKKK!!! THWACKK!!



   I squirmed around on her lap desperately as the harsh wooden paddle landed on my punished bottom with a blistering sting. Thinking I was done, I tried to get up but Melissa held me down.



   WHAPP!! SMACKKK!! SLAPPP!!! THWACKK!!



   I cried like a baby, slinging my purse and pounding the floor as she kept spanking me, slapping my glowing globes with ever greater ferocity. I wanted to cry out that she was only supposed to spank me three times but I could barely catch my breath and when I did, I howled with pain, squalling like a little child.



   SMACKK!! CRACKK!!! SMACKKK!!!!



   I thought she was going to break the paddle on that last whack and my mary janes danced frantically on the floor as I kicked and cried. Bawling like a baby, I struggled to my feet, holding my wet diapers, plastic panties and purse before me like a sissy shield.



   Vanessa held her arms out and I ran to her embrace, sobbing against her big, soft bosom as she held me close and stroked my head soothingly. I held her tightly, my new mommy, beautiful and powerful and so very strong. I looked up into her pretty dark eyes and I knew she would always know what was best for me. I sniffled loudly and cried, watching her chest slowly rising and falling as she reached down and took hold of my c*ck pacifier. Still whimpering softly, I watched as she brought it up to my lips and gently pushed it into my mouth.



   "There, there," she said soothingly, "hush, little baby."



   I had to open wide to fit the big dil-do in my mouth and I blushed as I suc-ked on the big rubber coc-k head.



   Slowly, she sat me down on the floor in front of everyone and re-arranged my wet diapers, pinning the squishy, saturated cloth back into place. I squealed in protest but she ignored me and re-snapped my plastic panties back into place, sealing in both the wetness and the fire on my bottom.



   "Come here, Jimmy," Ms. Taylor beckoned to me, "here's your panties."



   Holding the panties up that went with my white baby dress, I went over and stepped into them. I must have lost them sometime while I was getting my spankings. Ms. Taylor pulled the stretchy pink panties up my legs and then over my plastic panties, adding to the effect that Vanessa had already started.

[Anonymous]

One by one, my guests said goodbye and Vanessa made me stand on the front porch and wave at them as they walked out to their cars. At one point, I noticed Melissa whispering to Vanessa and I cringed at what she might be discussing. It was early evening by the time everyone had left, with the exception of Melissa and Tara. At last, my former nemesis took me by the hand and led me upstairs where I was terrified as to what was going to happen.

   "Melissa says she wants to see your nursery," Vanessa had explained, but for some reason I didn't believe her.

   Opening the door, Melissa slapped me on my pantied bottom to get me in quicker. I stumbled in with my wet diapers clinging to my seat and crotch while Tara moved to close the door.

   "It's just like old times, ain't it?" her trouble making, but attractive friend said threateningly.

   I looked from her to Melissa hoping for some reprieve but none was coming.

   I watched as Melissa tore off her mini-skirt with a haste that took my breath away, revealing a pair of high cut, black leather panties. For some reason, the dark, shiny look of them against her smooth, supple skin filled me with fearful anticipation.

   Opening her purse, she produced a large, imposing strap-on dil-do, at least ten inches in length and big enough that her fingertips couldn't completely wrap around its massive circ-umference. It was extremely realistic in appearance with multiple veins running back from the big, shiny head. With a wicked look in her eyes that I'd seen before, Melissa stepped into the intimidating device and secured it around her sexy, curvy hips, making me gulp and suc-k feverishly on the fat rubber dil-do pacifier in my mouth.

   I watched her with a mixture of familiar fear and secret admiration. I had always felt a confused, yet deep seated envy for this strong, confident woman, despite her bossy and demeaning nature. With her long, powerful legs and big bre ( " at " ) sts, my will crumbled and I was easily intimidated. Just being in her presence brought about strong feelings of submissiveness and inferiority in me and I felt like a weak, little boy in his diapers.

   She went over to my crib and swung the side downwards, opening it up for me. With her long, red tipped nails, she snaked my satiny rumba panties down my legs and gathered them around my ankles. Leading me over to the crib, she bent me over and made me grasp the far bars, forcing my knees to the floor.

   "Spread your legs, Sissy," she ordered me tersely, "you've had this coming for a long time."

   I whimpered fearfully with my mouth full of rubber c*ck as she grasped the back of my plastic panties and yanked them down forcefully, unsnapping the double rows of snaps on either side of my panties with one quick pull and exposing my wet cloth diapers. Unpinning them impatiently, she pushed them down just far enough to give her an unobstructed access to my anus. I heard her coating the massive dil-do with vasoline and my heart was beating wildly with nervous anxiety. My mouth went dry and my rear end puckered with anticipation as I waited for the inevitable, forceful invasion of my rump.

   With my cheeks still hot and stinging, I felt her prying them apart and the blunt, sticky end of her dil-do pressing urgently against my hole. I squealed like a little girl as Melissa applied steady, but firm pressure against my rosebud, trying to fit an impossibly big coc-k into my teeny passage. I tried to squirm away from her determined entry to try and prevent the gargantuan dil-do from coming in and I was rewarded with several harsh slaps against my already smarting bottom. I cried loudly but the big dil-do filling my mouth made my protests sound girlish and insignificant.

   Finally, after several minutes of earnest, but unsuccessful attempts, I felt her halt her anal attack and she delivered an angry smack of frustration against my bottom cheek.

   I howled in pain but was relieved in my belief that she had at last given up.

   "Tar," she said to her friend, "can you pull his cheeks apart so I can get this in?"

   I quailed in fear at her implacable determination and I whimpered in terror around my pacifier.

   Tara was only too happy to help and I felt her grasping both bright red cheeks in her hands, spreading them wide for Melissa's big rubber coc-k. With another layer of vasoline quickly applied to its massive rubber head, she pushed it up against my defenseless back door, refusing to give up.

   I tried to squirm away from the determined invader prodding impatiently against my anus but Tara easily held me in place, preventing any hope of escape.

   Suddenly and inexorably, I felt the huge phallus slowly push past the ring of my sphincter and I moaned loudly.

   "OOOOMMPHHH!!" I wailed helplessly.

   I knew the skin around my hole had been stretched to the very limit, struggling mightily to accommodate such a monstrous dil-do, and I gasped as it slowly slid into me. I felt like I were being impaled by a baseball bat and my toes curled as I put my head against the vinyl plastic of my crib mattress and lay in place, submissively taking my punishment. Rather than fight it, I lay obediently motionless, and let her push the monster deep into my rectum. With my face against the waterproof plastic, I breathed deeply the smells of vinyl and stale pee as Melissa slowly pumped my tender bottom. Gazing backward at the mirror covering the wall, I watched as she grasped my hips and forced her strap-on deep inside me, making me moan like a little girl.

   I looked like such a weak, effeminate sissy in my white fluffy baby dress and knee socks while she looked infinitely powerful, her strong, firm thighs flexing as she drove the fat dil-do deep, in and out of my backside. Her big bre ( " at " ) sts hung down within her top, swinging back and forth with each punishing thrust of her pelvis. I grabbed my pink teddy bear and suc-ked frantically on the big rubber coc-k in my mouth trying to take comfort while Melissa proceeded to pound me from behind. I watched in the mirror as she thrust her strap-on in again and again, reaming my poor sissy hole with her tool. Tears of frustration trickled down my face as she buried her faux coc-k deep into my rear end, driving it in until it bottomed out and then she'd hold it there, forcing me to feel every inch and refusing to let go of my hips while I squirmed and moaned. At the same time, my little trussed up pen-is was receiving it's own share of torment. With by backdoor being filled to capacity and pumped like never before,  I wanted nothing better than to obtain sexual release, if only briefly.

   My chastity device seemed to mock me without mercy and its bonds cut into my little package as Melissa rammed me again and again.

   "OOOMPHH! OOMPHH!!!" I cried as Melissa smiled down on my sissified pose.

   I sobbed with humiliation and groaned as my little pecker strained against its bonds, trying to get hard but completely unable to do so. It was so incredibly frustrating, being humped without mercy by stern, strong Melissa, and unable to get any kind of relief for myself. I gripped the crib bars and suc-ked harder on the fat dil-do pacifier filling my mouth, gasping to take in air.

   Stepping up her pace, Melissa forcibly pounded my fanny remorselessly. I watched her clenching her teeth in intense determination as she hammered my bottom with deep, powerful thrusts. My body bucked while my bottom quivered and I had to grip the crib bars just to hold on while she drove the massive dil-do in and out. I squealed and moaned at the top of my lungs, my poor rear getting the reaming of its life. A fine patina of sweat had appeared on Melissa's forehead but she kept driving away in earnest, her boobs shaking mightily and threatening to spill out of her top.

   It was then, that I caught movement out of the corner of my eye. I saw the nursery room door open and framed in the doorway was Vanessa. At last! My new mommy had come to save me, save me from this punishing ordeal! My hole was sore and it ached from being stretched so mercilessly. I was desperate for her to be my savior and stop this terrible raping of my rear.

   Melissa saw her too but she never missed a beat and she just kept pounding away at me, driving the dil-do like a jack hammer into my back hole. I saw Vanessa smiling and nodding in satisfaction, apparently pleased by the fact that I was getting humped good and hard.

   Finally, after I thought my hole couldn't take any more, Melissa cried out in orgasm, and she plunged the dil-do in as far as it would go, holding it there while she spent herself. I struggled to get out and away but she held me in place, forcing me to savor the big rubber coc-k buried deep inside me. At last, after she'd caught her breath again, she eased it out and I sighed with relief. My poor butthole was throbbing and my pen-is was in pain from the constrictive chastity loops. Vanessa walked in and rolled me over, checking my little wiener closely.

   "Works like a charm!" she beamed at the others who broke out into giggles.

   Melissa undid the strong harness straps of her strap-on with the practiced ease of someone who used it regularly.
   "All done?" Vanessa asked her.

   "Yeah," she said, still breathing hard, as she looked down at me with a leering smile, "for now, I am."

   "Well, I'm sure Jimmy would love to thank you personally but unfortunately he's got his mouth full of c*ck right now," Vanessa told her jokingly.

   Tara and Melissa burst out laughing and then Vanessa moved me over to the changing table to take care of my diapers. Melissa was cleaning her tool like a professional, wiping down the long, thick shaft with baby wipes until all the vasoline had been removed.

   "Thanks for calling me," she said to Vanessa, who was busy smearing diaper rash ointment across my red, spanked bottom.

   "Don't mention it," she replied as she slid a stack of fat diapers under me, "anytime you want to come over and do it again, just holler. I'm sure it will do him a world of good."

   My heart sank as I contemplated further sessions with Melissa and her strap-on. It was going to be a week before I could walk normally again!
   The three hugged and exchanged kisses while I sat on my arranged diapers, waiting for Vanessa to finish. When they left, Vanessa returned to getting me ready for bed.

   "Well, you certainly did have a wonderful birthday, didn't you?" she said with a big smile on her beautiful face.

   With my lips wrapped around the rubber c*ck filling my mouth, I wasn't in a position to contradict her and soon, my diapers were being pinned into place and a pair of plastic panties drawn up my legs. My satin rumba panties had been put away for the night but she found a babyish pink nightey that was soft and comfy and she helped me into it. Putting me back into my crib, she pulled up the baby blankets around me and raised the crib bars, latching the side shut with a secure 'click'.

   "Nightey-nite, Sissykins," she said softly as she walked out of the room, turning off the lights as she went. It was only seven o'clock and I was left in the quiet of the room, my only companion, the Barney nightlight on the far wall.

   As I pondered the events of the day, I saw the nursery door open once more and an unfamiliar figure was backlit by the hallway. Pulling down my blankets, I sat up to see who it was that was walking in and staring at me.

   "Jimmy? Is that really you?"

   I froze in place, as I realized the voice belonged to my mother.

   Whereas she was silhouetted by the light behind her, I was fully illuminated and she stared down at me in shock with my baby clothes and sissyish appearance. When she'd last seen me, I had had the look of an adult man but now, with my girlish Shirley Temple hairdo, frilly nightey and thick diapers, I looked like a three year old toddler girl. I gulped in fear and apprehension at her seeing me like this.

   Pulling down my blankets the rest of the way, she exposed the shiny nursery print plastic panties I was wearing over the super thick diapers clearly visible through the filmy fabric of my nightey. Gripped by panic, I proceeded to flood my fresh diapers. My eyes began to tear up as I felt the spreading wet warmth that I was helpless to stop.

   Putting her hands on her hips, she stared down at me angrily.

   "Well. I guess I always knew that you were a sissy but I never realized the extent until now.

   "Still wearing diapers, I see," she said in disgust, "and wetting them like a baby, from the sounds of it."

   I hung my head in shame as the pee saturated my crotch and began to seep back between my legs.

   "And what on earth is that in your mouth?" she suddenly asked incredulously.

   I blushed three shades of red as she popped the coc-k pacifier out of my mouth roughly. I had been suc-king on it for so long, I had simply forgot it was in my mouth.

   "Mommy!" I cried out, suddenly bursting into tears as I continued to soak my diapers in a display befitting my infantile appearance.

   "Don't mommy me, you big sissy baby!" she snapped angrily, "it's obvious you still need diapers and the kind of discipline that only Vanessa can provide for you."

   I pouted in silence as my mom scolded me like a child.

   "I guess it's true what they say," she continued, "once a sissy, always a sissy."


   


                     THE END