Transvestite

Sub

/ Categories: Cuckold, Domination/submission, Erotica, Fiction, Foot or shoe fetish, Transsexual, Transvestite, Voyeurism, Wife / Cuckold, Domination/submission, Erotica, Fiction, Foot or shoe fetish, Transsexual, Transvestite, Voyeurism, Wife / By

I might be the luckiest man on the planet. I was born an only child to a family of great wealth, I have all the things money can buy, and the most beautiful wife in the world who I love, worship and adore with all my heart and soul. She is literally a beauty queen who won competitions in one of the largest states in America for her statuesque, fit but voluptuous body, cascading golden hair, and a face that could launch a thousand ships. My wife would never have noticed me, as I am hardly a specimen of masculinity, except that I was persistent in my pursuit of her, which consisted of constantly showering her with gifts, a Ferrari, a thoroughbred horse, diamonds and rubies, and use of my private jet to go on …

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Pleasing Bill: A Crossdressing Story #3

/ Categories: Anal, Blowjob, Discipline, Domination/submission, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / Anal, Blowjob, Discipline, Domination/submission, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / By

[b]Chapter 3: Mom’s Talk [/b]I woke up early the morning after my first day of being Bill’s live in slut. I got up to listen and hear my dad and siblings leaving for work around 7. I was going to wait for all of them to leave before I dress and go back to Bill’s at 12. I went to lie back down but before I could, I heard my mom call me. “James, honey. Can you come down here?” I didn’t know what to say a first. She probably wants to talk about how she saw me last night. I guess there was nothing else I could do but go down there. I was in my pajama pants and a white tank top on with the black and pink Daddy’s slut colr on. I …

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our walk part 1 & 2

/ Categories: Gay, Group Sex, Older Female / Males, Threesome, Transvestite, True Story, Wife / Gay, Group Sex, Older Female / Males, Threesome, Transvestite, True Story, Wife / By

***********************************************our walk**************************** Recently my wife asked me if I jerk off, And I said yes, she then asked me what i thought about while doing it. I told her my many fantasies. She agreed to help me fullfil one. I got home from work last week, it was late, my wife told me to take a shower and put on the outfit she laid out in the spare bedroom for me. When I got out of shower i went into the backroom and found A pair of black tights (with hole cut out for my cock) a black leotard , oversize hooded sweatshirt and sneakers. I was trembling as I got changed, My cock was rock hard sticking out of the tights but covered barely by the nylon of the leotard. I went into the …

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Nerves, Shivers, Cum

/ Categories: Anal, Transsexual, Transvestite, True Story / Anal, Transsexual, Transvestite, True Story / By

The panties were tight. My legs and underarms were shaved, and the panties clung to my cock, smushing it between my legs where it was hidden and not in the picture. He met me at the door and led me into his room, walking slowly behind me, breathing heavily. I walked in and stood with my back to him, nervous, vulnerable, and dressed in pants and a baggy shirt. Beneath my clothing were black satin panties and a matching black satin bra, and pantyhose. As I stood there, anxiously, he could sense my nervousness. I could sense his presence, as his panting drew closer and closer to me, and I began to shiver. He quickly got up behind me and wrapped an arm around my neck and an arm around my waist, his hand reaching …

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Working ‘Girl’_(1)

/ Categories: Blowjob, Boy, Fantasy, Gay, Prostitution, Transvestite, Young / Blowjob, Boy, Fantasy, Gay, Prostitution, Transvestite, Young / By

Brian sat impatiently on the park bench, fidgeting in anticipation and excitement. He quickly checked his phone for the time yet again, seeing it was just after 1AM. It was the perfect time for meeting a customer. He reached over to run his fingers along the signature red bracelet over his left wrist, which let men in the area know he was ‘working’. His ears perked up when he heard some noises off in the distance, a gentle rustling in the bushes. Brian smiled slightly, knowing someone else must be doing just what he was about to do now. He thought about that video game he wanted, the one all the other kids at school were talking about. But at 14, he was too young to have a job, and too old to convince his …

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The New Girls_(0)

/ Categories: Anal, Black, Blowjob, Coercion, Domination/submission, Group Sex, Reluctance, School, Science-Fiction, Spanking, Threesome, Transgendered, Transsexual, Transvestite, Virginity / Anal, Black, Blowjob, Coercion, Domination/submission, Group Sex, Reluctance, School, Science-Fiction, Spanking, Threesome, Transgendered, Transsexual, Transvestite, Virginity / By

“Hey loser,” Ken says as he shoves me into my own locker. “You’re such a fucking sissy. You know that, right?” “Good one, Ken!” Weston says. “Why do you guys always have to pick on me?” I ask. Ken goes to hit me and I cower. “Because you’re such a fucking loser,” he says, laughing. I look up at him as he gives Joseph Palmer a fist bump. “Later sissy,” Alonso says as they walk away. “Man, they are such douchebags,” Anthony says as he and Marcelo walk over and help me out of my locker. “I was going to give them such an ass-kicking, but fortunately for them, they walked away.” “Come on, Anthony, don’t lie. You and I were both hiding around the corner when we saw Ken pushing Noah,” Marcelo says. “Hey, …

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Becoming Jane

/ Categories: Fantasy, Transgendered, Transsexual, Transvestite / Fantasy, Transgendered, Transsexual, Transvestite / By

Becoming Jane Part 1 John had always been a little bit different. At a young age he had discovered porn. It started with pictures and magazines. Then the internet brought him movies. He became addicted. First it was straight porn, then interacial. Then he discovered strapon femdom witch quickly led to transexual porn. Soon he began sneaking around wearing his mothers panties and playing with his ass. At 17 he was still a virgin until he joined an adult dating site and met an older man. He lied about his age and met up with him. The older man had been his first. John had been nervous in the back of the Jeep Cherokee as he kissed the man and then lowered his lips to the man’s seven inch cock. John took the man’s cock …

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Growing Up CH1

/ Categories: Boy, Fiction, First Time, Teen Male / Female, Transvestite / Boy, Fiction, First Time, Teen Male / Female, Transvestite / By

Chapter One: I start a babysitting job First I’ll explain myself. It was one more year ‘till I got my learner’s permit. I was a freshman, not masculine, slim arms and hips, narrow shoulders. I grew long dark brown hair that I kept hidden mostly under a cap or a beanie and sometimes in a ponytail so nobody really noticed how long it was. Brown eyes. I was pale, long legs, a few inches over 5 feet, fresh white skin with ruddy cheeks, (the zit demon had skipped me over). Hairless arms and nearly hairless legs, just a very light fuzz. I certainly didn’t shave yet. But I had a butt! I wore jeans and cords all the time and my butt looked good in the mirror, tight and round and kinda bulgy. I was …

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Suzy Unleashed Chapter 1

/ Categories: Oral Sex, Slavery, Transgendered, Transsexual, Transvestite, True Story / Oral Sex, Slavery, Transgendered, Transsexual, Transvestite, True Story / By

Suzy Unleashed Chapter 1 I’ve always had a fondness for women’s clothing, dating back to when I was a young boy. For most of my life, I kept that under control, but, as I got older, the fascination only increased. After I got married, I discovered I had an entire wardrobe of women’s clothes to try on whenever my wife wasn’t around. Eventually, the fear that I might soil or tear something of hers and get caught pushed me to invest in my own female clothing, which I managed to keep hidden in the attic. Over time, I built up a nice collection of skirts, panties, garterbelts, stockings, and even high heels and a wig. A flesh-colored body-stocking covered up my hairy legs and arms so that I didn’t have to explain shaving them to …

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Your tansgender girlfriend

/ Categories: Transgendered, Transsexual, Transvestite, True Story / Transgendered, Transsexual, Transvestite, True Story / By

There are times in a young man’s life when it is so full of fun and sex that it’s a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it’s self. Yea, it was the late 80’s and the me decade was in full swing. I can’t say that I immersed myself in the culture of the times, but just like walking across a muddy field you can’t help but get some on you. I was in and out of several relationships with girls of many different types but couldn’t seem to find that one woman who rocked my world. Well, at least not …

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One Summer Day

/ Categories: Anal, Consensual Sex, Fiction, Transgendered, Transsexual, Transvestite / Anal, Consensual Sex, Fiction, Transgendered, Transsexual, Transvestite / By

I always found my sister-in-law, Cara, kind of attractive, even as my girlfriend and I were dating at the time. She was already married when I started dating, but I was already mesmerized by her beauty. At my wedding, Cara wore a beautiful strapless turquoise dress that rivals my wife’s white wedding dress. I would have been fine if they had switch places that night. However, my wife never truly got along with her sister. Cara was…careful with their money with her own family, but freely spend it with friends and her husband’s family. She would also spend time with her friends weekly, but only went to her parent’s house once or twice a month for dinner. My wife has always taken care of her parents better than Cara did. The animosity between them was …

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Suzy Unleashed Chapter 11

/ Categories: Bi-sexual, Diary, Transsexual, Transvestite / Bi-sexual, Diary, Transsexual, Transvestite / By

Whether it was exhaustion or the fact that I was beginning to accept my new life, I slept really well on Thursday night and woke up refreshed and ready to go. As usual, while I showered, Kathy laid out my outfit for the day, ***********ing one of the dresses she had bought the day before to help fill out my closet. The tight red dress barely stretched over my enhanced chest and the hemline was only inches below my ass. I knew that as tight as it was, bending over the coffee table at work was going to be an adventure, and when I tested it by bending over in front of the mirror, my suspicions were confirmed: the matching red panties Kathy had laid out were clearly visible. Surprisingly, I found myself smiling at …

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The Walk…continued (pt2)

/ Categories: Bi-sexual, Cum Swallowing, Fantasy, Romance, Transgendered, Transvestite / Bi-sexual, Cum Swallowing, Fantasy, Romance, Transgendered, Transvestite / By

The walk’ continued. ‘I will ring you soon’ I said, and pecked him on the cheek, then he turned and quickly kissed me on the lips, ‘naughty’ I said, but leaned forward and kissed him back, just a peck, then a bit more. I moaned softly and pulled away, ‘next time’ I said, ‘I’m not a first date kind of girl’ We both giggled this time. ‘bye’ I said ‘call you soon’ and walked towards the car park, looked back and waved and headed off, feeling slightly lonely now, but aroused and excited? Now the story continues………………. Walking back to the car I felt like a bit of a dumbass, here I was, out dressed as a girl, on my own. ‘yup, on your own, asking for it in the middle of a forest, just …

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Suzy Unleashed Chapter 2

/ Categories: Fiction, Slavery, Transgendered, Transsexual, Transvestite / Fiction, Slavery, Transgendered, Transsexual, Transvestite / By

I tossed and turned most of the night trying to think of a way out of the trap Kathy had put me in. At times I told myself that she’d never follow through on her threat and that I should refuse to go along with her desires. Of course, I also wouldn’t have believed the things I’d already found out—that she was fucking Ron and that she was more than willing to force me to blow him. If she was willing to do those things, how could I be sure she wouldn’t distribute those damn videos? I woke up about 6:00 with my bladder ready to burst. Quietly I climbed out of bed and went to the bathroom. When I finished, I walked back into the bedroom, still not sure what I was going to …

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Kylee’s Sauna Fantasies

/ Categories: Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Fantasm, Toys, Transgendered, Transsexual, Transvestite, Young / Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Fantasm, Toys, Transgendered, Transsexual, Transvestite, Young / By

Last Saturday I went over to a friend’s house to eat and he had his sister, Kylee, over for dinner. For some reason it seemed like they didn’t like each other very much. As the food was set out to eat they argued over who was going to sit where; she wanted to sit next to me, but my friend was the man of the house and he won the debate. Rosa sat across from me. She sat down slow and winked at me while doing so. We were having a roast with broccoli and baby carrots. That night Kylee was wearing a thin blue silk dress that rode up half her thigh when she sat down. Constantly I was in an internal conflict; trying to get a peek under that flimsy dress and trying …

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Taken

/ Categories: Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Fiction, Hardcore, Transvestite / Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Fiction, Hardcore, Transvestite / By

It all seems like a dream but here I am. on my back, legs spread and feet on his shoulders as he makes me his sissy. Up until just a few minutes ago, I was very afraid of what was going to happen to me. Now, with his reassurances and tender gentle lovemaking, I am truly enjoying this. I should go back to the beginning and explain just how I unwittingly found myself in the situation. I moved into this small rental home just a few weeks ago. It is in a very nice quiet neighborhood where most of the people are friendly and tend to mind their own business. There are neighbors on each side and both are older gentlemen One is divorced and the other told me he was a confirmed bachelor. We …

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Suzy Unleashed Chapter 7

/ Categories: Blowjob, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / Blowjob, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / By

I woke up on Monday morning to the feel of Kathy stroking my erection through my sheer panties. “Mmmmmm,” I purred, “that feels nice. You haven’t done that to me in a long time.” “I know,” she smiled. She kissed me softly on my lips and explained, “I woke up so excited, and when I saw your cute little hardon, I just couldn’t resist. Do you like it?” “Oh, yeah,” I sighed. “Does it make you want to fuck?” “Oh, God, yes,” I groaned. She kissed me again. “Do you want to fuck until you cum? Would you like that?” “I’d love that!” I answered excitedly. Again her lips found mine, and this time her tongue slid into my mouth. I moaned softly and she said, “Oh, my, you really are horny, aren’t you?” “God, …

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Suzy Unleashed Chapter 6

/ Categories: Blowjob, Domination/submission, Fiction, Transsexual, Transvestite / Blowjob, Domination/submission, Fiction, Transsexual, Transvestite / By

I woke up on Sunday with Kathy’s words from the night before echoing endlessly in my head. It was now beginning to sink in that I was actually going to spend an entire week as a slut, sucking whatever cocks Kathy and Ron told me to. As I thought about my situation, it dawned on me that I wasn’t sure which part was the most disturbing—that they were going to use me that way or that I wasn’t repulsed by the idea. “How can I be letting them do this to me?” I wondered. “How can I be willing to go down on whoever they say? It’s so humiliating and disgusting!” I closed my eyes and pictured what I knew was going to happen to me, with cock after cock spewing into my mouth. As …

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Sister’s Dress Up Doll – revised

/ Categories: Blowjob, Fiction, Reluctance, Romance, Transvestite / Blowjob, Fiction, Reluctance, Romance, Transvestite / By

Kimmy was your reasonably normal 16 year old girl, maybe a little odd at times, but it was normal to her. Her family was comfortable, not wealthy but not poor. she lived in a fairly large house with a decent sized yard with both her mom, who was not home very often as she spent a lot of time travelling on the job, but was home enough to be a fixture and dad who was worked a lot of hours at the school she attended. Her little brother, Johnny, on the other hand was 14, and went to the middle school in the allocated area. the popular toy at the time were these plush dress up dolls, this is a strange phenomenon as the doll phase usually phases out at a young age, but this …

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my birthday gift_(1)

/ Categories: Transvestite, True Story / Transvestite, True Story / By

*****************************My Birthday ****************************************** For my birthday, my wife asked me what I wanted( I threw her a huge 100 people party for hers) I told her I didnt want a party, but that I wanted a threesome with another woman. We have had a couple of threesomes, all with other guys. She is straight and said she is not comfortable with another woman joining us.but would be open to another guy joining us again and doing whatever I wanted. I have a huge pantyhose fetish and love wearing them. I told her this time I wanted to dress up fully, she agreed saying “it’s your Birthday”. she told me to find a guy and book a hotel room for the up comming weekend. I booked the suite at the local hotel and figured I would …

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