Bubba To Sissy free porn video

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Bubba to Sissy It was a sad day for me when I received word that my Aunt Beatrice had passed on. Not that I hadn't been sort of half expecting it, at least in the back of my mind. She'd been getting on in years and was in poor health. I regretted not visiting her more towards the end, but we had written to one another on and off. She was very special to me, the first person I ever came out to. I really only confirmed what she had always guessed, she always saw the real me, even when I was a little boy. I had never known who my father was anymore than my mother did, being the way she was. She drank and partied and fucked around without restraint or regard for me or anyone else and growing up I often found myself left with my aunt for weeks at a time until, finally, my mom was killed in a drunken car wreck when I was 17. Beatrice owned a beauty parlor in the rural area where we lived and I stayed with her in the apartment above it before I set out on my own for the big city, with stars in my eyes and dreams of being an entertainer. It was there I began to learn what would become my true profession. She even paid for cosmetology school at her insistence that I should have a skill to fall back on. And thank god she did. And so it was, with only mild surprise, that I found out that she had left me the place, having no kids of her own. So I took a few days off from the upscale salon where I rented a station and drove back to where it had all begun for me. The town seemed completely unchanged when I pulled in; dusty and sleepy as ever, except for an increase in cars passing down the main street where her shop was. I'd arrived too early to go to the office of the lawyer who'd written, so I just parked and stood looking in the window of the old place for a while. Torrents of memory swept over me as I stared at the faded and peeling curly-cues of lettering that spelled out "Bea's Beauty Hive" on the window. The little bees that swarmed around the words, once so bright, were now just blobs of pus yellow and gray. It hadn't been open for couple of years now and looked the same inside, only old and run down. My plan was to arrange for its sale for as much as I could get as fast as possible and get back home. I had never really fit in around here and now I stuck out like a stubborn cowlick, in my city fashions and rainbow stickers on my car. As I stood there musing on happy and sad memories, I became aware that I was being watched. Such an obviously gay man has to be extra careful in a area like this, so I glanced around to see who was taking such an interest in me, alert for any possible threat. A man about 15 years my junior was keeping a close eye on me from just around the edge of the building. He was shorter than I was and rather plump, with long greasy hair pulled back in an untidy ponytail. A sparse beard crawled down his face and neck and he was dressed in tattered jeans and the tee shirt of a long defunct heavy metal band that might have fit him twenty pounds ago. A beat up baseball cap and mirrored sunglasses completed this look of ragged machismo, but, instead of the aggression I had anticipated for someone queer violating his territory, he seemed to be the one who was nervous. He kept looking at me and my car, then up an down the street apprehensively. Then, as if deciding it was safe, he shuffled up to me quickly and said hi. I cautiously retuned his greeting and when the silence began to grow, he started rapidly to ask where I was from and how long I was going to be in town. I answered him in a non-committal way that I'd wouldn't be staying long and he blurted out that he ran the "fix-it" shop behind the building. Then he took off his shades to reveal startlingly girlish, soft brown eyes filled to overflowing with a desperate hunger and asked me if I'd like to see his place. Oh my god, he was hitting on me! Now, maybe fixed up a little, I might even have found him kind of cute, but I'm just not that easy nor was I in the mood for some small town closet case. I told him no, rather coldly, but he pressed in closer to whisper a far more graphic invitation, if not now then maybe later before I left. He was really starting to bring my claws out, but, before I could say anything, he saw someone coming up the sidewalk behind me and swiftly scurried away. I stared after this odd creature and his panicked retreat with some disbelief, then turned to see what had scared him off. Three casually well dressed men were walking towards me with overly friendly smiles on their faces. One of them tuned out to be the lawyer I was waiting for and the other two were the mayor and the president of the local bank. It seemed that the biggest fish in this tiny pond had weirdly turned out to welcome me. Then the mayor asked me if Bubba had been bothering me. This question was quickly followed by the explanation that Bubba, though not well liked by most, was nothing to worry about. It was just that he was well known for being very outspoken about how much he detested (and here the mayor paused, choosing his words carefully) "fellows like me". He intensely assured me that folks around here weren't like that at all and if Bubba ever gave me any trouble again to just let him know and he'd sick the sheriff on him. This was offer was even more bizarre because I recognized that he and the lawyer were both guys who had given me a lot of grief, back when we were all teenagers. But now they all seemed quite intent on winning me over for some reason and invited me to breakfast with them at the diner across the way. It was all too strange, but I went along with them, anxious to get on with the business of my aunt's estate and more than a little curious about this unexpected reception. And so we sojourned to the diner where they all told me how sorry they were about the death of my aunt, what an important figure she'd been to the community and how proud she'd been of me. The lawyer produced Bea's will and other related papers and I was surprised to find out that she had not only owned the shop, but the entire building it was in. I asked how long they thought it would take to sell it all off and that's when the mayor launched into a clearly well thought out sales pitch and the reason behind why they were all so glad to see me. The town had been barely hanging on for decades, he said. But, just last year, both a new veterinary and a junior college had opened up close by. Now, most of the students of these colleges lived in a nearby bedroom community and this town was located between them. He had the figures to show me that the amount traffic on main street had increased to ten times what it had been before, as the students came up the old state highway to avoid a toll road that went to the campuses. But the expected upswing in business due to this hadn't materialized. They were passing through without stopping. What the town needed was something to attract them. And that's where I came in. Since a clear majority of the students were young women, they all thought that a really nice, modern hair salon would get them to stop and bring in more business for the whole of downtown. There were no other places like they were envisioning anywhere nearby, only chain chop shops at distant malls. They effusively spoke of my aunt's praise for me as a talented hairdresser who worked in only the best salons in the big city. Everyone was ready to give me whatever support I needed, financially or otherwise, if I would just consider staying to renovate and reopen my aunt's old shop. I sat there, flabbergasted, while they went on. I wasn't just being wooed, I was being downright seduced. And as the cajoling and flattery flowed from the trio, I thought of my life back home. It was true what they said about my work, but, like this town, I'd been in steady decline. Sure, I still worked in a top salon, but for how much longer? I was almost fifty now and my clients had been drifting off to younger stylists. The rent on my station was high, the management's cut, big. I had a small apartment, a ten year old car, no savings and no steady boyfriend. And what hairdresser didn't dream of running his own place? There in the city, I was nobody; just another aging queen. But here, I was the potential savior of a whole community and they were ready to bend over backwards to help me do it. I played it cool after they'd finished their spiel, telling them I'd think about it, but in my mind I was already planning it all out. It was amazing how smoothly it came together. With backing from the bank, I redid the shop, even salvaging a lot of the old equipment and mixing it's funky retro look in with modern renovations. I scouted and hired the most talented stylists in the area, teaching them my best tricks of the trade and the latest trends. I gave free makeovers to local girls and sent them to places and events where they would be seen. Everyone turned out for our grand opening and soon the passing cars were stopping and the joint jumping. Not just the college girls, but women and men from all over. And it worked for the town too. Women would come to get their hair done and stay to shop or eat. I even began to advise the other business owners on what to serve, what to stock and how to decorate. Even the hardware store and sporting goods shop began to flourish again, as men waited for their wives. Soon I was expanding, doing nails and hiring a talented colorist. Salon Beatrice (it's new name) was the alarm clock that woke the sleepy town and made it shake off it's dust. The only person who didn't welcome my presence was the man who had come on to me so awkwardly that first morning: Bubba. As described, he was very vocal in his hatred of "filthy faggots" in general and me in particular. But, along with the rest of the town, I paid him no mind, knowing that his remarks were born out of self-loathing and the terror that I might out him. Funny thing was, I owned where he lived and worked. His repair shop was in the rear of my building and he lived above it, as I lived above the salon. When word got back to me of the things he was saying, I was advised that the lease on both places was with people he taken it over from and I should just kick him out. But, you don't run a place like mine without quickly finding out everything there is to know about everybody thereabouts and the more I learned about Bubba, the more I began to feel for him. He had been orphaned early in his life and passed from relative to relative before he landed here in the care of an elderly couple, distant cousins to him. He had been a shy boy who took up alcohol fueled bravado in his teens. He had little skill for repairing things, but kept the shop going out habit once the old couple had passed on. He squeaked by on odd jobs and what little business he could handle, continued to drink and would disappear from time to time to go on fishing trips, but never brought back any fish. He rarely showered, was generally rude and obnoxious and only tolerated out of pity. I had no shortage of social contacts and invitations while living there, especially after my salon had worked it's magic. I had become a kind of pet gay guy for every would-be fag hag around. The men were cautious, at first, but relaxed when they realized I wasn't out to rape them all or convert their sons. Still, being busy with the salon left me little extra time and when I did have some eventually, I would spend it fixing up my apartment. The closest thing I had to a love life was the occasional married man slyly dropping hints about being "bi-curious". But I certainly wasn't into anything like that. I guess, despite my popularity, I was as lonely as Bubba must of been. But, I figured I could tough it out for a couple of years before selling off and returning to city life a much richer man. The apartment above the shop was huge, with a couple of unused rooms filled with my aunt's old junk. When I had nothing better to do, I would sort through it, keeping a few things but mostly getting rid of stuff. One night, I finally made it back to what I thought was the door to a closet. I saw that it had been painted shut. Wondering what I might find behind it, bodies or treasures, I got a knife and started to get it open. Rosemary's baby! It wasn't a closet, it was a connecting door to Bubba's apartment! Intrigued, I cut the paint from the cracks and tried the knob. It was unlocked. I oiled the hinges and slowly pulled it open, the snoring from the other room never changing rhythm. Carefully, I looked inside. There was a dim hallway on the other side and I stepped cautiously through. I saw a light and heard snoring from another room at the end and crept towards it. It was Bubba's bedroom, alright, there he lay on the cluttered bed, passed out with a half a bottle of whiskey by his side. At first I was concerned that he was bleeding from the mouth, then I realized it was smeared lipstick. He was out cold, so I came all the way in and looked around. Bubba was wearing an ancient frilly night gown and granny panties, run stockings pulled up his hairy legs. He had put his hair up in two high ponytails on either side of his head tied with garish plastic hair ornaments. There was a nasty looking, but realistic latex dildo next to his head and it was smeared with the same colored lipstick. There was porn all over the place and as I looked at what kind it was, I started getting crazy ideas. I snuck back to my side and got my digital camera. Three weeks later, I sat alone in the closed salon with the shutters closed tight, waiting. At the time I had appointed, there was a tentative knock at the door and I opened to find, as I had expected, Bubba standing there with fear in his eyes. He had the print out of the picture I had taken of him and shoved under his door, along with my note, crumpled in one hand. "Please..." he began, but I cut him off with my best pseudo butch voice. "Shut up faggot," I snapped, "and get in here!" He slid in sheepishly and looked around, terrified. I looked at him sternly and pointed to my station, ordering him to sit down. He sat on the edge of the seat and I shoved him roughly back into it. He started ask me something, but again I cut him off. "Not another word," I demanded, "You'll do exactly as I say or I'll post those pictures all over the county." His eyes widened at this threat and then lowered in submission. I produced a pair of handcuffs and fastened them to his wrists, then restraints around his ankles so he couldn't pull them more than a half a foot apart and attached these to the footrest of the chair with a bit of rope. Another length of rope went over his chest and around the back of the chair. Then I stood back and looked at him, smiling evilly. I snatched the sweat stained baseball cap off his head and threw it in the trash. I jerked off his stinking tennis shoes and socks, revealing his grubby, untrimmed toenails. He looked as if he might scream when I picked up a razor, but quickly thought better of it, holding his breath in terror. I pinched the threadbare collar of his tee shirt, with it's flaking slogan and rotted armpits, and split it open. He wasn't quite as hairy as I'd thought he'd be and had a lovely set of boy titties. I cut the rest of the shirt off of him, yanked open his ridiculously huge, tin belt buckle and slowly pulled down his zipper. Peeling back the denim, I smirked as I exposed the frayed elastic of a ratty pair of flowered, cotton panties. They looked like he'd pulled them out of a dumpster. I giggled at them, then cut the jeans off him. It was warm in the shop, but he shivered as I stalked in a circle around him, slowly. He gave a slight gasp when I used the razor to nick the rubber band that was entangled at his neck and it flew open. I dug my fingers into the greasy, mud-colored mess, pulling out loose hairs and dragging his head back until it lay all about his shoulders. It hadn't even been trimmed in years, it's ends were split to the nape. I pushed some into his eyes and still butching it up, I picked up my big, black Oster clippers and asked: "When's the last time you been to the barber, boy?" and I flicked on the clippers, the tone of their whirring motor growing menacingly in pitch as it gained speed. "Or should I say girl?" I snapped the waistband of his panties and lay the flat of my palm over their front. His cock, half hard since I'd cut off his pants, stirred and grew erect beneath the stained purple and pink print. "It looks like you're not sure yourself." I clutched his balls and base hard and he jumped. "Well, you feel like a boy." I stood up and walked behind him, looking at him in the mirror. "So I'll just have to give you a boy's haircut." I brought the blades towards his head and he instantly flinched away. I played with him a few times like that before grabbing his hair next to his scalp and yanking his head back, hard. He gave a little shriek and I ran the clippers over his hair without cutting it, just letting him feel the vibration and heat. He started breathing in quick, short breaths as I stroked them over his scalp to torture him until tears formed in his eyes and ran down his cheeks. I let go. "What's the matter Bubba?" I taunted, "Don't you want to look like a boy?" He shook his head back and forth violently, his dun, scraggly hair flying about. I gathered it up into a tall, tight pony and jerked his head back. "Then it looks like you've made your choice," I hissed, then added: "Sissy." I touched the clippers to his face and, delicately and ruthlessly, ran their many, tiny, blindingly fast scissor teeth through the roots of his beard. He shivered and squirmed and tried to hold still as the stiff little curls tickled their way down his naked chest. Then it was even more naked as I sheared off his chest hair, making teasing loops around his nipples before denuding his belly. I untied the rope around his shoulders, gripped the handcuff chain and pulled his arms above his head. With two swift strokes I whisked off the fetid hair of his pits and let his hands drop. I took as much I could of his leg hair with him sitting, turned off the clippers and stepped back to look at him. "That's a good start. But before we finish that up, we'd better do something with what?s on your head." I picked up a brush and began brushing it with long, deep, scalp-scratching strokes. I was so dirty that it started to gleam like it had been oiled very soon after I'd begun. He even started to relax a little as I continued. Then I parted it down the middle from forehead to nape and braided it into tight pigtails and tied the ends with bows of pink ribbon. His eyes looked even more feminine than ever now that he appeared hairless from the nose down and with his locks in shiny, beribboned plaits. They kept darting between me and himself in the mirror and were filled with conflict and fear turning to pleasure and anticipation. His confusion deepened as I tied a second bit of ribbon to his braids just at his chin. "Keepsakes," I explained cryptically. Then I seized one tightly, picked up my scissors and, without hesitation, sawed through it as he sobbed soft protestations. "Shhh," I whispered in his ear as I cut the second one, "Girls have to get their hair cut too." I used the severed pigtails to wipe away his tears with their paintbrush ends and ran them lightly over his body. The remaining three inches of braided hair started to come undone as I released him from the chair and helped him stand up. He was wobbly and the short link still connecting his ankles forced him to mince to the shampoo sink. I eased him down and back and started in on a badly needed hair washing. I scrapped my nails on his scalp as I firmly scrubbed it, deliberately using overly hot water and an eye stinging amount of suds. When I brought him up sputtering, I roughly toweled him dry and prodded him back to my station and into the chair. I swung him away from the mirror, threw a plastic cape over him that clung to his wet, naked shoulders and pumped him up to a proper working height. He smelled what I was up to next before he saw it, his nose and forehead wrinkling at he same time from the sharp reek of the ammonia. Without warning, I dumped the hair dye into his jagged bob and worked it through with gloved hands. I removed the gloves when done and set a timer. While the dye worked, I reclined the chair and mixed up hot lather in a mug. I worked the lather into his face and neck with the shaving brush and used a twin blade disposable on them until both were smooth. The timer rang as I finished and we repeated the awkward march to and from the shampoo sink. I was careful to make sure he couldn't see the results so far as I re-caped him and picked up my scissors and comb. Fearful of what was to come, he sat stark still and moved his head about in the directions I pushed it. His eyes widened as shorter and longer bits of bright red hair started to fall. I had already decided what I was going to do as I cut layers into his hair, the kind of style I've always loved but never get to do. He trembled again as I used the clippers oh-so lightly at his nape. The cutting soon done, I whisked away stray hairs and scooped up a generous handful of setting gel. After saturating the fiery mop, the point of my rattail began scrapping out a grid of sections, each one wound tightly around my finger tips before being bobby pinned flat against his skull. When I was done, the Xs of crossed pins covered his dome and pressed the hair down so completely as to almost look as if I had buzzed it all off. There had been definite change if him since first arrived. His terror of injury or exposure had melted away to nervous, yet curious, trepidation. I undid his leg restraints and used the cuffs to pull him to his feet. "I don't think you'll run away now, will you?" I asked, looking him in the face as I pull down the nasty panties, throwing them away. He looked down, embarrassed, shook his head slightly and whispered, "No. No sir." "Then it's time for your bath. Upstairs." And gave him a little shove in that direction. Once upstairs, I drew a steaming bath in the enormous old claw-foot, with sweet smelling salts and mountains of scented bubbles. As the tub filled, I pulled small battery clippers out and skimmed off the remaining hairs from his legs and buttocks. His eyes closed, I took hold of his stiff cock and balls and did the same to them, stretching them this way and that to get every follicle. I unlocked the handcuffs, warning him I didn't want any trouble, and held his hands as he lowered himself into the bath. I had lit candles and incense and even brought him a glass of pink wine in a long stemmed glass. Popping a shower cap over his set, I turned on soft music and watched as he luxuriated in the warm suds. Gently I scrubbed his skin and covered each part with a smooth lavender shaving cream and, using a triple bladed ladies razor, patiently removed all traces of body hair from his toes to his chest. He seemed glad to do as I instructed , having him stand and present every part of himself for the razor's caresses; sighing as I stroked his crotch, tensing as I shaved the crack of his ass. Afterwards, I vigorously toweled him off and unveiled some of the things I had ordered and recently arrived. When I handed him a new pair of lacey panties in aubergine silk, I thought he might start crying again. I helped him into a matching bra and fastened it in back when I could see he didn?t know how. Then I directed him back downstairs and into a dryer chair. With him sitting under the dryers hot blast, I rolled over a prepared cart. He watched in silent fascination as I smeared a paste of bleach onto his unshaven forearms then sat on a stool to give him a pedicure, no easy task on the callused and hitherto uncared for feet. But I got through it and painted his freshly trimmed and filled toenails. I used the same color on the false nails I applied with his manicure, pausing between the two tasks to rinse off the bleach and reveal the hair on his arms, thinned and paled. I checked his pin curls, and although they were not quite dry, led him back upstairs and to the bedroom. I had him stand with his back to me and hold on to the posts of the old brass bed. I wrapped a black satin and lace corset around him from behind, reaching around him to fasten it's front. For the first time, I let him feel my own hard-on through my pants and his panties as I pressed in close. I stepped back and began drawing the laces tight. He gasped and rocked the tighter I drew them and compressed his middle to a suitable size for a beginner. Tying off, I turned him around, careful to pull the corset's garter straps under the dark purple panties. I bunched up the waiting hose and had him lift each foot and point his painted toes and unrolled each up his smoothly shaven legs to his thighs. I clipped the to the four straps that hung off the corset and tugged at the backs to straighten the seams. I was pleased to see that everything fit well, since I could only guess at sizes when I ordered them. But the corset was just right, restricting with room for more. The narrowing of his waist by it made his hips and ass look huge and his boy-tits filled out the eggplant bra nicely. By contrast, to go over all this chic lingerie, I'd chosen a belted shirt dress, with a below the knee, flared skirt and ? sleeves, simple, yet classic and elegant. He looked very uncertainly at the pumps I helped him into and there was a comic moment or two as we made our way back down to the shop to finish. I sat him in the styling chair again and decided to bust out an old hood dryer for his hair. As it inflated on his head, I leaned the chair back, selected a fitting template, and applied wax to his eyebrows. I could see he was afraid of this, but now seemed to trust me completely. He grimaced as the strips were ripped away, but bore it bravely. I set him aright and started applying foundation to his face followed by the rest, eye shadow and pencil and liner, with mascara for his already thick lashes that made his eyes so feminine. A touch of blush, then lipstick, lined and in layers with powder to make it last. It was then I picked up the needle, like you would use on a hypodermic syringe, thin and sterile. I held it and looked into his eyes, holding his with mine. He licked his now blood-red lips and nodded. I placed a cork behind each lobe as I pierced them and pushed white gold rings through the tender holes. "Good girl," I praised in his ear and, like a reward, drew a pearl necklace around his throat, with a matching bracelet for his wrist. I pumped up the chair and took off the dryer's hood. Absolutely at ease, he settled in to enjoy the new sensations as I pulled the pins from his now crisp curls and began combing and brushing them into the shape I had envisioned. When it was perfect, I sprayed it to stay that way. He looked about to bound from the chair and spin towards the mirror, anxious to see. But I stopped him and brought out a little gift wrapped box and gave it to him. He smiled and opened it, gleeful to discover the high quality perfume it contained. I showed him how to put it on, just the lightest touches behind the knees, on the wrists and beneath the ears. Then I spritzed it into the air above him where the tiny droplets of mist hung for a second like stars before drifting down to scent perfect, red curls. I pirouetted the chair and let him look. The ruby mouth fell open in silent shock. Long nailed hands patted at the stiff russet hairdo, an exact recreation of the bobbed and set styles of fifty years past. The fingertips traced, barely touching, the beautifully painted face and across the dress front and down to ascend back up the smooth stockings of the calves. Jumping up, he found his balance on the tall heels and tried to examine himself from every angle the mirror would allow, shaking the unmoving curls, clicking the unfamiliar nails and inhaling deeply at his wrists until I interrupted this revelry by seizing one. "Now that you're ready, it's time for your date," I said, matter-of- factly. He froze at these words and stared at me, frightened again. I tugged him gently up the stairs, his footing again unstable. I brought him into the living room, got us drinks and a few hors d'oeuvres I'd prepared. We sat on the couch in front of a fire I lit in the hearth and listen to the music I'd put on. I only spoke to correct him in errors feminine deportment. He did not speak at all, only doing as I instructed and nervously eyeing me over the top of his wine glass. I looked her up and down in the flickering light and silently congratulated myself on my work. I joked with myself, in my mind for the millionth time, if I was really gay. For, although I love men and always have, I love nothing better than a man dressed like a woman. I leaned in and lightly kissed the lipsticked lips. He drew back, but I pressed on, drawing him close and kissing him again, insistently. He kissed back timidly but again broke off and tuned fully from me when my tongue began to slide past his lips. I reached around and squeezed both his breasts hard and pinched his nipples through the silken fabric. He continued to pull away, growing more distressed, drawing a knee up onto the cushions as if to lever himself over the arm of the couch. This only served to thrust his skirted and pantied ass at me and I grabbed him around his corseted waist and rubbed my stiff cock on it. Then I jerked him back down into a sitting position and stood over him as we both caught our breathes. Glaring down on the top of his perfect coiffure, I sharply tipped up his chin with one hand and seized one of his with my other, guiding it to the front of my pants, making him feel the throbbing erection. "Isn't this what you want?" I demanded, "To be a woman to a man? To dress for him and be seduced or even raped by him?" He swallowed hard as he looked up into my unrelenting stare. The false nails adding to his awkwardness, he managed to pull down my zipper retrieve my pulsing rod. His hands shook as he touched it and his lips trembled as his mouth fell open. Then he let go, covered his eyes with his hands and burst into tears. " I don't know how..." he was finally able to choke out between sobs, "I never...I mean... Nobody ever..." Dumbstruck, I sat down next to him and held him while he cried and kept trying to explain. "Sometimes I'd drive for days to somepla... Anywhere I might meet... But nobody ever wanted to... With me..." and he threw his arms around me and couldn't speak again for several minutes. "I must look awful now," he said later, dabbing at his eyes with the tissues I'd brought him. "Not at all," I replied gently. I showed him how to fix his make-up in the bathroom and watched, delighted as he primped with gestures long practiced in his imagination. He stood and admired the whole effect as he had before downstairs, then turned and looked at me. "Thank you," he said, "thank you for this." "I hardly deserve..." I began, but he stopped me. "No, you do. I've never felt pretty before. Never felt that maybe I could be beautiful." "You are beautiful," I said honestly. We walked back into the living room, hand in hand. We finished the wine and even danced a little, swaying to the old, slow love songs. I kissed him again and he eagerly kissed back and looked up at me and asked me to take him into the bedroom. Holding him by the hand, I led him in to stand before a long mirror that hung on the door of the armoire. He watched and sighed as I kissed and nuzzled his neck from behind, running my hands up under his skirt. I turned him to face me and unbuttoned his dress, letting it slip to the floor. I pressed close against him and, unhooking and removing his bra, I squeezed his breasts and sucked and nibbled at his nipples. Then I slid my hand down the length of the satin corset and into the silk panties. His hard, hairless cock and scrotum were in my hand and he ground into the palm. I pulled off the panties down over his stockings and helped him step out. He was mesmerized by the sight of the sultry redhead being caressed by her man in the mirror, her rigid penis a lovely and curious accessory to the total femininity of the rest of her. But there was more he wanted to see, sinking to his hose clad knees. Relishing the zippers inviting purr this time, he lowered my pants and, shyly at first, began to get the feel of my cock, studying it, drinking in this moment of discovery. His tongue flicked out to taste the thick lipstick he wore, drawing its unmistakable scent into his mouth. He mingled it with the odor of maleness that stood ready before that rosy circle. Starting with soft kisses he grew ever bolder until the head and upper shaft of was deep into his mouth and he watched, from the corner of his eye, himself at last; a sexy girl sucking cock. What he might have lacked in experience he more than made up for in enthusiasm, losing himself completely in this amazing host of new sensations. I'd would have gladly come down his throat then and there, but I wanted him to have everything that night, so I firmly took hold of his curls and drew him back. Breathing hard, he looked up at me with eyes that begged to continue but I lifted him up and, after a fierce kiss, pushed him on to the bed and maneuvered him so that he was on his hands and knees. I ran my open palms over his ample ass cheeks and a single fingertip along the cleft. I continued a bit and then spread them suddenly, plunging my head down and darting my tongue around his twitching pink rosebud, then lapping at it as he moaned and wriggled. Lifting my head, I got a finger of lube from the bedside pump and worked on and then slightly into there. He twisted and squirmed around so he could watch in the mirror as I fingered him with more and more until my whole forefinger was sliding easily in and out as he softly whimpered and purred. "You're getting so wet for me," I purred back, adding still more lube and a second finger. He moaned loudly at that and ran a hand over the slippery garments he wore, long nails ratcheting on the pearls. Three fingers now and that virgin place, at first resistant, stretched and accepted. Reaching underneath, I toyed with just the tip and glans of his stiff cock and then touched my own to his ass crevice. I soaked myself with lube and ran it up and down between his cheeks and hard against his ready anus. But I waited, to torment him one last time tonight, waited until he said it and he did. "Fuck me, please, please, fuck me sir, please fuck me!" he begged and I complied, shoving into him, making him gasp and claw the sheets and stare open mouthed at the image of a beautiful woman being passionately fucked from behind by her man. As I gained speed he squealed and thrashed about in astonishing ecstasy, shaking his head to feel the dancing cloud of curls on his cheeks, sucking in perfume, pointing his toes to enhance the pinch of the high heels. Then all else was forgotten as the head of my rigid, warm cock brought him to an orgasm like no other he'd ever known only to be followed by one greater and again before I howled aloud and pumped my steaming come into him. She didn't want to leave in the morning, and who could blame her? I could have shaved off the red and sent her back to hide plucked brows beneath ball cap brims and make up lies about drunken haircut impulses. But I found her in bathroom when I woke up, trying to do something with her hair. And when I came in, she asked so sweetly if I would help her, I told her we'd have to hurry, before the others arrived. I asked if she wanted some coffee and she replied it was already fixed. So I asked if she wanted anything else. "Yes sir," she said, dropping her eyes demurely, "will you please always call me Sissy?" Bubba was not the sort to be much missed. A couple of letters dropped into mailboxes in another city made short work of his meager affairs. We did that on a three day hotel stay when I took her there to visit some drag clubs and go shopping. The old repair shop turned out to be crammed top to bottom with vintage stuff that Sissy soon found herself learning to sell online. She never minded not going out and delighted in playing the perfect housewife for me. And when she did get restless, we'd just sneak away on a trip, like a couple eloping. Where he'd never been known, she was accepted for what she appeared to be. It is a very satisfying and rewarding thing to grant someone their truest desire. It's been two years now, tomorrow is our anniversary. Living like this, I hardly feel gay now, but for the certainty of his sweet and secret penis that is mine alone. And tomorrow I'll tell my dear, plump little wife that I'm selling the shop, the building, everything and, with the money I've made here and along with my investments, I'm opening a shop in the city, where she'll never need to hide who she has always been from anyone ever again.

Same as Bubba to Sissy Videos

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

1 year ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
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Saturday Morning Sissy

Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
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Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

1 year ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

3 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

2 years ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

2 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

2 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

3 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

2 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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