Transvestite

Jaclyn part one

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

Let me start off by saying that I have always enjoyed wearing women’s clothing, as far back as I can remember I love the feel of satin against my body. My first experience was when I was 13. I was in the bathroom, taking a piss, when I saw a pair of my mom’s black satin panties in the hamper, so I took my mom’s panties and off to my room I went. That night was my first experience, with women’s panties. The feeling of them hugging my little cock was intense needless to say I came very fast, When I was finished I couldn’t very well put them back in the hamper, so I stuck them between my mattress’s. Not too long after that I discovered transvestite website’s, I was stunned how these men …

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Hot Chocolate

/ Categories: Blowjob, Coercion, Cum Swallowing, Fiction, Interracial, Transgendered, Transsexual, Transvestite / Blowjob, Coercion, Cum Swallowing, Fiction, Interracial, Transgendered, Transsexual, Transvestite / By

“C-come on sis, I don’t want to do this!” His sister, Joanna, smirked and shrugged, “Aww, Casey, I really don’t care! Now, come on, pucker your lips up some more, hm?” After a reluctant sigh, he did so, quickly feeling her fingers on his chin, steadying him as she applied the red matte lipstick to his plump lips, “Yeah, yeah just like that, perfect…” “C-come on, you can’t be serious?” He complained, voice soft once she was finished applying it, looking at his sister with wide anxious eyes as she glanced in a mirror, pursing her own lips before glancing back to Casey, as if comparing them. “Yeah, you look perfect… One second, let me just do your eyelashes.” Casey let out another sigh, feeling the butterflies float around in his stomach as his sister …

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Something Extra_(0)

/ Categories: Anal, Bi-sexual, Blowjob, Fantasm, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Blowjob, Fantasm, Transgendered, Transsexual, Transvestite / By

The date had gone really well. Way better than I’d expected actually. Which was both good news and bad. I enjoy being wined and dined like any lady would. And I really had enjoyed dinner with this guy. He was quite funny which is always a turn-on. And he was just touchy-feely enough to make my heart flutter (and a few other pieces) but wasn’t forward enough to make me think I was just going to be another piece of tail. Not that I would have minded as this guy was CUTE. And built. I’d gone to extra lengths for this date too. Normally I’m pretty laid back on the whole girly-thing. My hair is short, black and usually a mess. I’m pretty pale as I’m terrified of skin cancer which is what got one …

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Kelly – Part 1

/ Categories: Consensual Sex, Fantasy, Teen, Teen Male / Teen Male, Transgendered, Transvestite / Consensual Sex, Fantasy, Teen, Teen Male / Teen Male, Transgendered, Transvestite / By

Do you know what it’s like be stuck in a dorm room with a male roommate, in an all-male residence hall, during a dry spell? When you can’t even masturbate because either your roommate is around, or you have homework or studying to do? I’ll tell you what it’s like. It’s like being starved. Red-blooded guys like me need a woman’s touch. We need to be between their legs, making them utter sounds only real men get to hear. We need the warmth and softness of a girl, or we go insane. And I was going insane. I hadn’t jacked off in a month. A month. And I hadn’t been able to score. Either I fucked things up, or luck came in and fucked it up for me; there was no getting laid. It was …

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Suzy Unleashed Chapter 10

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

By the time the alarm went off on Thursday morning, I was already awake, lying in bed thinking about what would be my second day on my new job. I couldn’t decide which of the emotions I was feeling was stronger: fear, shame or excitement. The one thing I did know was that in a short time I would be facing all three. Again, by the time I finished showering and shaving Kathy had laid out my wardrobe for the day. I was surprised to see that she had selected a red blouse and a relatively modest black skirt that was at least six inches longer than the dress I had worn the day before. I breathed a sigh of relief until I noticed that lying beside the skirt were a garterbelt and stockings. Knowing …

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Suzy Unleashed Chapter 9

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

I slept very little on Tuesday night, tossing and turning as I tried to come to grips with the step I was about to take. At about 5:00 I decided I wasn’t going to get any more sleep, so I got out of bed, and, with nothing else to do, started to prepare myself. I showered and shaved both my face and my entire body, making sure there was absolutely no stubble left behind, then spent over an hour carefully applying my makeup and another half hour applying bright red polish to my artificial nails. By the time Kathy got out of bed, I was satisfied that I looked as good as possible. Kathy immediately confirmed my belief, telling me how beautiful I looked and what a great job I had done with my makeup. …

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Meeting my on-line lover

/ Categories: Fiction, Gay, Transvestite / Fiction, Gay, Transvestite / By

I met Mark online. I’d joined a gay chat room. I had been fantasizing about being with a man for a while and this was a harmless, anonymous way to explore my interest. To begin with, I was very shy and didn’t know how to respond to the occasional message that came my way. Then I got into a conversation with a guy who made all the running. I only had to go along with his messages. I’ve discovered that the best cybersex is to be had by going along with the person you are playing with. Unless it takes you somewhere that is a turn-off, if you build on whatever comes from the other person, it can be very arousing. I allowed myself to forget all my inhibitions and commit to the scene. It …

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MORGANA AND RAELINE

/ Categories: Ass to mouth, Bi-sexual, Blowjob, Erotica, Exhibitionism, Female/Female, Group Sex, Hardcore, Lesbian, Male / Older Female, Oral Sex, Transvestite, True Story, Voyeurism / Ass to mouth, Bi-sexual, Blowjob, Erotica, Exhibitionism, Female/Female, Group Sex, Hardcore, Lesbian, Male / Older Female, Oral Sex, Transvestite, True Story, Voyeurism / By

My hands moved quickly behind her. Holding one arm around her waist, I pulled her back against me, with my other hand hoisting up the back of her skirt. Her wonderful creamy thighs and magnificent ass cheeks were naked above her stockings. I cupped my hand over her pubis. “You’re dripping wet,” I said huskily. She still didn’t move. “I’m always wet,” she replied. She heard the zipper of my fly snap open, then with one hand in the centre of her back, I bent her over the windowsill. A moment later she felt me large and hard inside her. She gasped, her concentrated gaze out the window broken, her hands resting against the windowsill for support. She gasped again. A mew like groan came from her throat. My hands grasped like vices against her …

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Life long TV

/ Categories: Bi-sexual, Cum Swallowing, Transgendered, Transvestite, True Story / Bi-sexual, Cum Swallowing, Transgendered, Transvestite, True Story / By

Hello all you sexy readers! I’m Lori, a transvestite, and here are a few little tidbits about me. I can remember loving girly things ever since I was very young. I had three sisters and my mom’s stuff to admire. I was about four or five years old when I noticed nthat I loved the feel of soft, silky under garments. By the time I was seven I would sneak a pair of panties from the hamper and wear them to bed. Soon I would take a bra on occasion and wear it too. I steadily progressed to include nylons, slips and even girdles! I loved trying on new things as often as possible. By the time I reached thirteen I was dressing from head to toe. Being the oldest, and only “boy” in the …

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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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