Once A Sissy Always A Sissy
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Once A Sissy Always A Sissy
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Once a Sissy, Always a Sissy by Baby Bobby (Author's note; this is the sixth story in the Jimmy series, for those of you who have been following along :D ) As I sat on the bus making it's way across town, I fidgeted nervously, pondering the events that had led me to this point. Last week, my first and only serious girlfriend had kicked me out of her apartment after she had caught me masturbating again. Things had not gone too well for me with Jenny, starting with her discovery of my pen-is, or rather, the lack of one, in her eyes. I suppose I had been in denial about my diminutive weiner, which had never really grown much since I was in the second grade. It still was little more than a stub, even when it was erect, and it's diameter was about that of my pinky finger. Of course, it didn't help things that I was a premature ejaculator as well. These things all conspired to bring a my relationship with Jenny into a downward spiral and she immediately stopped giving me any sexual attention of any kind. At the same time, she started treating me more and more like a little boy but I guess I was so used to being dominated by strong women all my life that I just went along with it. Two weeks ago, she informed me of her intention to start dating other men. When I protested, she responded by pulling me over her lap and spanking me with her hairbrush until I was sobbing like a baby. I should have left right then and there but I couldn't. I guess I've always been weak willed and I kept rationalizing why I should stay with her so I just learned to accept the situation. However, since I wasn't getting any sexual gratification from her, I became increasingly horny and masturbation was the only relief I could get. One day while I thought she'd be away for a while, I found one of her Victoria's Secret catalogs lying around. No sooner were my underwear in a circle around my ankles and I was readying myself for some badly needed relief, when Jenny barged in with one of her new boyfriends. To make a short story even shorter, she lost no time in yanking me over her lap and spanking the daylights out of me with her hairbrush again--in front of her boyfriend no less! After that, she kicked me out permanently and I was forced to walk all the way back to my mom's house. The masturbation episode was the last straw for Jenny and immediately after had she kicked me out, she called my mom up and told her everything, telling her I was nothing more than an immature sissy who needed his mommy. Needless to say, my mom was anything but pleased when I got home. I knew that for sure when she met me at the door with the paddle in her hands. She dragged me inside and after tearing my pants down, proceeded to give me my second blistering spanking of the day. After a good cry and a 'time out', with my nose pressed into the corner and my trousers gathered around my ankles, my mom returned to the living room with a suitcase in her hand. "Jimmy," she said with great deliberation, "I've tried to do my best to raise you to be a decent young man. Apparently, I've failed in my task so it's time for someone else to have a crack at the job. "I'm sending you to live with my friend Vanessa who lives on the other side of town," she informed me stonily. "V-Vanessa?" I asked shakily as I rubbed my stinging bottom that was still bared and red as an apple. "That's right Jimmy, Vanessa. I trust her completely and I know she can handle a grown up sissy like you." Now, as I sat on the bus, still shifting uncomfortably in my seat because of the duel spankings, I pondered my new living arrangement. I hadn't seen Vanessa for years, not since I was kid, although I still remembered her with a strange mixture of arousal and humiliation. She had treated me to my first and only sexual experience when she had allowed me to nurse from her wonderful, massive bre ( " at " ) sts. Everytime I thought about it, my tiny pecker stirred and my heartbeat quickened. Back then, Vanessa had been a total babe, with an unbelievable body. I had been ten and she was in her mid-twenties which would make her mid-thirties now. What did she look like now, I wondered. Maybe she'd let herself go and gained a million pounds, I thought absently. Maybe she was wrinkled and ugly, or just plain dumpy looking... I would know very soon, I realized as the bus took me steadily closer to her home. If she was good looking, I was determined to show her the new me. Now that I was twenty and all grown up, I was in a position to be able to talk with her as an equal. This time, she wouldn't be changing my diapers, and this time, maybe we could even go out on dates! I knew I was getting ahead of myself but I couldn't help fantasizing with my memories of her. I pictured myself taking her to an elegant restaurant, and then back to her house, where I'd ravish her and kiss her wonderful bosom. Ah, if only I could make that happen! The bus finally lurched to a stop outside a wealthy gated community and I took my suitcase and got out, introducing myself at the guard shack. The sentry let me in and gave me directions for the short walk to Vanessa's house. Evidently, she had done very well for herself since I had known her, as was quickly becoming apparent by the expensive homes I was walking by. Holding the paper in my hands with her address written on it, I came at last to her house. It was quite impressive, with a Mercedes parked out front in the driveway and a fancy hedge surrounding the large yard. Walking up the stone pathway, I rang the doorbell, with butterflies in my stomach. In the silence of the neighborhood, I could hear the clicking of high heels as they approached the door on the other side. My heart immediately began beating harder when the door suddenly opened. A young woman of about eighteen, dressed in a french maid's outfit stood framed in the doorway and she took my breath away. She wore 5" high heel black patent leather pumps, dark silky hose that showed off her fabulous, long legs, a very, very short black skirt that flared out over a white ruffled petticoat and a low cut white blouse, revealing a pair of beautiful bre ( " at " ) sts that were pushed up into a mouth watering cleavage. She had a dark choker around her neck and her long brown hair was pulled back from her gorgeous face. As I stared up at her green, piercing eyes, my mouth opened and I tried to stammer out some sort of greeting. She was the kind of girl who was quite aware of her beauty and despite her veneer of politeness, she looked down on me with obvious superiority and confidence, making me wilt in return. "I'm-uh, ah, I'm...my name is, ah,-" I babbled incoherently. "Jimmy," she said sweetly as she broke into a smile that just about knocked me over. "Er, Jim...is my name," I said, trying to correct her. "Come in, we've been expecting you," she said as she stood back to let me in. I stepped up into the house and was led into a fancy living room, lavishly appointed with furniture and art that looked like it cost a lot of money. Out of the corner of my eye, I watched the maid walking in behind me, her long sexy legs competing for my attention as well as her exciting bre ( " at " ) sts. "My name is Barbie," she said softly, making me want to melt, "I'll inform Vanessa you're here." I was totally captivated by this young, sexy beauty and I nearly drooled as she turned around and stode into the other room, her high heels clicking on the hardwood floor. This was going to be great! I thought to myself as I pondered the best method to flirt with this knockout. Somehow, I had to put my experiences with Jenny behind me and score with Barbie at the soonest possible opportunity.
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« Reply #1 on: May 09, 2006, 05:12:28 PM »
My mind was still reeling from the possibilities when I heard two sets of high heels coming my way. Standing up, I saw the tall, familiar figure of Vanessa come around the corner and my jaw dropped for a second time. Far from having put on the pounds, my former babysitter was awesome in every way! She wore a semi-sheer white blouse that looked like it was about to burst open from her massive cups, held in check only by a lacy white demi bra that could plainly be seen underneath. She had unbuttoned the first three buttons of the blouse which gave me a view of the deep line of cleavage that disappeared down between her incredible bre ( " at " ) sts where they were pushing against each other. Below that, she had on a beige skirt that came down to a few inches above her knees, which hugged her slim form very nicely. Her high heeled open toed sandals revealed her immaculately manicured toenails. I had forgotten how tall she was and when she came over to hug me, she mashed her big bosom against my chin, smothering me in a wonderful, erotic embrace. I was ready to die and go to heaven! "Jimmy!" she said cheerfully, "you're all grown up now." "Uh-huh," I said as I relaxed within her strong embrace. "Last time I saw you, you were still in diapers," she commented with a knowing smile. I blushed deeply, hoping she wouldn't elaborate any further in front of Barbie, who I hoped was still unaware of my long and drawn out childhood that had been filled with diapers up until the age of fourteen. "Er, a lot of things have changed since then, Vanessa," I said meakly. "Well, we'll see," she said with a smile as she patted my bottom affectionately. I wasn't sure what to make of that comment but in my fog of arousal, I brushed it off without further thought. "Come upstairs, I'll show you your room," she said to me. Barbie wandered off elsewhere and we climbed the curving steps that led to her upper floor. My eyes were glued to Vanessa's saucy bottom and her smooth, slender legs atop her high heels as she slowly ascended the stairway. "This sure is a nice place," I said in wonderment, trying to ease my excited tension from being in such close contact with two total babes. "Thank you, I'm an investment banker for a financial institution here in town," she informed me. She sure didn't look like any banker I'd ever met, I thought to myself. She led me into the first door on the right which was a softly lit room, appointed in a very feminine fashion, but which was very typical of Vanessa. It was more girly than I would have liked but who was I to complain about free room and board? I sat on the four poster bed and recognized immediately the sound and feel of a vinyl mattress cover under my rump. Why would that be here? I wondered. For my fifteenth birthday, my mom had given me several pairs of training panties, to replace my daily diapers although I was still having a problem at night. By the time I was sixteen, I finally stopped wetting the bed although my mom still insisted I wear diapers and plastic panties to bed for another year, just to be sure. Had she said something to Vanessa, I asked myself. Again, I decided not to say anything about it. Maybe it was from someone else who had stayed here. "I'll just let you unpack your things, Jimmy. I run a pretty informal place here and Barbie usually eats dinner with us. That'll be about six o'clock," she told me as she stood with her hands on her curvy hips. "Okay, thanks Vanessa," I said, trying studiously to avoid staring at her b**bs. "It's good to see you again, Jimmy," she said smiling, as she bent down and kissed me on the cheek, leaving the impression from her lipstick there while I blushed furiously. "Me too," I stammered, feeling foolish and inadequate all over again. After Vanessa left, I struggled to get my runaway libido under conrol and settle down, even though I wanted badly to sit down and diddle myself with the images of Vanessa and Barbie swimming through my head. I began opening drawers to put my stuff away. I froze when I opened the top drawer which revealed a stout, oval shaped wooden paddle, with a double line of holes going down it's length. I looked at like it was a cobra and my stomach tightened into a knot, my mind imagining it slapping my bottom while I was made to bend over Vanessa's lovely lap. I shuddered involuntarily and closed the drawer. I filled the second and third drawers with my clothes but then got another shock when I opened the bottom drawer. It was the tallest of the group and it was filled with stacks of soft, cloth diapers. On the right side of the drawer were stacks of plastic panties, in various pastel colors of pink, yellow, peach and lilac. With my heart pounding in my chest, I picked up one of the panties to check it's size. Maybe they were for a kid, I hoped. My hope dwindled when I saw they were right in my size. Frantically, I threw it back and closed the drawer quickly. I could only hope and pray those weren't intended for me although I had a nagging suspicion they were. Dinner went well and I forgot about the diapers as Barbie showed that she was as good a cook as I'd ever experienced. We sat around talking until about nine when Vanessa drew me a bath and invited me to make use of whatever I needed. I relaxed in her tub and it seemed all my troubles had gone away as I soaked in comfort. Finally, when I was finished, I dried off and went back into my room, my towel wrapped around me. Vanessa was waiting for me there, with her back to me, and when she stood back up to face me, my mouth dropped open in shock. There, laid on the bed, was a changing pad, three diapers in a stack, pins, baby powder, and pink plastic panties. "I thought I'd help you get ready for bed," she offered very matter-of-factly, as if it were nothing in the world. "Huh?" I exclaimed, "but I don't wear diapers anymore!" "Now Jimmy, it's been a long day and I think we both know this is better for both of us. This mattress was twenty five hundred dollars and I don't want to take any chances," she explained patiently. My heart sank as I realized that Vanessa's perception of me hadn't changed at all in the last ten years. To her, I was still a bedwetting child who needed to be fastened up into his diapers every night. "But-but, I really don't need them," I tried to tell her. "I'm sure you don't," she said, although her tone of voice clearly said otherwise, "but I think for tonight, we'll just be sure, okay Honey?" I hated being talked to like I was four year old, especially now that I was an adult. "But-I-I," I tried to protest as she removed my towel. "Hush, Baby," she said soothingly as she lowered my nude form over the stack of diapers. I blushed beet red as my bottom came into contact with the bunny soft cloth underneath me. All the more so since she could now see my tiny pen-is plainly sticking up like a tan crayon. Looking down at it, she giggled and put her hand to her mouth to try and hide her amusement. I blushed even redder and Vanessa bent forward, her huge bre ( " at " ) sts swinging before me, mesmerizing me like a form of hypnosis. "It'll be our little secret," she assured me as she took a handful of diaper rash creme and began smoothing it across my bottom. I bit my lip in embarrassment as she looked into my eyes while she did this most intimate procedure. When she had coated it with a thick, sticky layer, she rubbed her creamy fingers down my slippery crack, sending erotic shivers coursing through me. Baby powder followed and she wasn't stingy with it as she covered my crotch and between my thighs with the softly scented powder, making a cloud rise up around me. Humming to herself, she drew up the thick cloth between my legs and pulled the ends together at my side. "This is just like old times, isn't it, Honey?" she said as she smiled down at me while she pinned the diapers shut with pink duckie pins. "Uh-hm," I said, too embarrassed to return her look. I felt like I was ten years old all over again, having my diapers changed by my beautiful babysitter. Shaking out the shiny pink plastic panties, she gathered the leg holes and then began snaking them up my legs. When she reached the base of my diaper, I lifted up my bottom obediantly as she tugged the panties up and over the fat diapers, circling around my hips several times with her manicured finger nails as she worked the panties over the big, bulging diaper. "This should hold you 'til morning," she said, obviously satisfied as she snapped the elastic waistband with a flourish. I blushed again while she held me close to her and hugged me, bringing my face into close contact once more with the softness of her big bre ( " at " ) sts. I breathed in the intoxicating scent of her skin and perfume and my head swam with desire, despite the intense feelings of humiliation that were washing over me. After a moment, she stood up and pulled the sheets back, beckoning me to get in bed. "Nighty-nite, Jimmy," she said, "sleep tight, Baby." I waddled over to the bed and got in, the all too familiar feeling of thick padding between my legs and embracing my hips. As I moved around, the noisy vinyl sheets reminded me of their presence and I felt so childish that Vanessa couldn't trust me in her bed without diapers and waterproof sheets. With another kiss on the cheek, she turned and left the room, shutting out the lights as she went. I sat there, staring up at the ceiling, wondering if I'd ever be treated like an adult.
« Reply #2 on: May 10, 2006, 11:27:28 AM »
That night, I had troubled sleep. My dreams were filled with humiliation and visions of when I was ten. I was wandering around Vanessa's house in a pink party dress and diapers, desperately trying to find my babysitter. I looked in every room but I couldn't find her anywhere. All of a sudden, Brittany showed up from out of nowhere and she had a mean look on her face. I was terrified of her after all she had subjected me to, and my only response was to flood my diapers in a wild panic. She laughed mockingly at me and then she dragged me out into the living room where everyone had gathered. They all laughed at my appearance and made humiliating comments to me which only made me pee my diapers worse and that's when I started crying like a baby. Suddenly, Brittany was approaching me with the paddle in her hands, a determined look on her face. "Now I'm really going to give you something to cry about," she said as she grabbed me roughly by the wrist. "Nooooooo!!!" I cried. Suddenly I awoke with a start. Warm sunshine was streaming in through the lace curtains and I realized it was morning already. With a shock, I also became instantly aware of the soggy wet mass within my plastic panties--the all too familiar feel of soaked diapers. Oh no! I glanced up at the door and saw it was slightly ajar. I could hear voices nearby in the hall and I recognized them as Vanessa and Barbie. What was I to do? I looked around the room thinking maybe I could stash the diapers somewhere but then what? My mind raced as I tried to concoct a plan but I just couldn't think straight. Then, suddenly without notice, Vanessa came into the room. She was wearing a short, white halter top that hugged her big, bountiful bre ( " at " ) sts showing every curve in the most delightful manner. They seemed to be spilling out of the top and her spaghetti straps looked strained to hold her bosom in. A smile was on her face as she came in and stood next to the bed, bending over to greet me. "How's my little baby?" she asked as she started pulling the covers back, "
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