Transvestite

My little secret

/ Categories: Anal, Bi-sexual, Boy / Boy, Fantasy, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Boy / Boy, Fantasy, Transgendered, Transsexual, Transvestite / By

My crossdressing started in Jr. High. When I started to get curious about girls, and also about other boys. I started crossdressing with my moms things, and slowly started to collect my own. By the way, I’m Mat… or Ashley as i’m known. I’m 17 and I guess you could call me Bi-Curious. Although after this story you could call me purely Bi-sexual. I have a friend, Katelin is his girl name but everyone knows him as Jake. He’s the same age, and we’ve been good friends for quite a while. We found out about each other last summer. When a pair of panties I thought I had hidden, suddenly came out into the open. Before I could react, he grabbed them and started asking me all kinds of questions. “Whos are these, what are …

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Dressed to Thrill (Part 1)

/ Categories: Bi-sexual, Domination/submission, Fantasy, Female Domination, Masturbation, Transvestite, Wife / Bi-sexual, Domination/submission, Fantasy, Female Domination, Masturbation, Transvestite, Wife / By

Dressed To Thrill – Part 1 It was only a matter of time before my wife discovered what I am, and I discovered her need to dominate and control me.   We worked different hours and I was often in the house alone which only encouraged my kinky tendencies. When she was away or had meetings she would get up and go to work early and I would stay home until it was time to go out later. It began innocently enough I suppose with looking at things on the internet and whilst my wife is an incredibly sexy and curvaceous woman I knew I needed more. I began to look through her drawers and her wardrobe to find the sexy and sluttish outfits to wear after she had left the house. I would get …

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Bitch in Heat_(3)

/ Categories: Anal, Authoritarian, Cum Swallowing, Gay, Spanking, Transvestite, True Story / Anal, Authoritarian, Cum Swallowing, Gay, Spanking, Transvestite, True Story / By

Bitch in heat Sitting at home, late at night, surfing the AOL chat rooms way back when could bring about some interesting opportunities. This is one such story. I had put away a considerable amount of work one day and was relaxing by searching through some AOL chat rooms… back in the day when it was the thing to do. Titles of chatrooms was one thing, but screen names were another… and searching for one of interest was always a bit of a chore. I had been hopping around different rooms for a while until I came across “Red Bottoms” which only had one member… “Master.” It didn’t take long for him to pipe up when I stayed in the chat room and offered a “Hello.” “Tell me about yourself” was what I got. “NOW”. …

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My little secret 3

/ Categories: Anal, Bi-sexual, Body modification, Fantasy, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Body modification, Fantasy, Transgendered, Transsexual, Transvestite / By

Sunday started with the sun in my eyes to wake me up. As I sat up in bed I heard moans and screaming of pleasure. Putting a Bra and panties on, I slipped on my robe and went to investigate. Jim and Tom were downstairs, pounding Katelin and she was enjoying it. Moans escaped Katelins lips as she sucked Toms cock, Jim was behind her thrusting in and out very violently. As I watched my own boy thing started to get excited, while it wasn’t fully hard it was still ready to go. “Get on the floor Tom” Jim said panting and breathing heavily. Tom laid down on the floor as Jim moved Katelin on all fours. “You go in first” Jim said pulling out of Katelin. Tom put his hard cock to Katelins hole …

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More than before.. part 1

/ Categories: Blowjob, Cum Swallowing, Fantasy, Humiliation, Transgendered, Transsexual, Transvestite / Blowjob, Cum Swallowing, Fantasy, Humiliation, Transgendered, Transsexual, Transvestite / By

for more of this story dm me ! enjoy! It had been a week since everything changed. A week since Lina’s body had started transforming and a week since they first crossed the line from curiosity into something deeper, something neither of them had words for yet. At first, she was shy about it. The way she tugged the hem of her hoodie down over her hips, the way she avoided his eyes when he touched her… Jason remembered every detail. But it hadn’t taken long for something new to wake up inside her, something bold. Something hungry. Now, it was Lina who led the way. Jason lay back on the bed, heart racing, as he watched her move with effortless confidence. She was small, barely reaching his shoulder, with a frame that still managed …

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What If I Told Him I Wanted To Give Him A Blow Job?

/ Categories: Bi-sexual, Blowjob, Fantasy, Oral Sex, Transvestite / Bi-sexual, Blowjob, Fantasy, Oral Sex, Transvestite / By

Tom called the other day and invited me to come spend the night at the cabin. He said his wife was out of town and suggested we could do some fishing and drinking. It sounded like fun so I told my wife I was going. (Actually, I asked if I could go and she said yes). Tom met me at the cabin with a beer in each hand and offered me one as we went inside. We got the boat out and spent the day fishing on the river. We didn’t have much luck but had a good time, downed quite a few beers and were feeling pretty good by the time we got back to the cabin. Tom’s a good cook and he fixed up a great pasta dinner. We drank beers, swapped lies …

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Sometimes Short for Samuel pt. 2

/ Categories: Anal, Blowjob, Fiction, Masturbation, School, Transsexual, Transvestite / Anal, Blowjob, Fiction, Masturbation, School, Transsexual, Transvestite / By

Sometimes Short for Samuel pt. 2 The first week in the dorm had flown past, I was falling into a routine. My nightly rendezvous with Matt was earning me some freedoms that I enjoyed. Jacob was so far unaware I think but growing suspicious of why I was getting up to use the bathroom every night at 2 AM. Jacob hadn’t mentioned the hand job I gave him on our first night together and I hadn’t brought it up. I imagined he was struggling with the idea that he had allowed a boy to handle his cock. I let it alone, figuring he would talk about it if he wanted, or maybe if he wanted another hand job. He was however not any stealthier about jerking it which was happening with what seemed like increased …

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silk and lace

/ Categories: Blowjob, Fiction, Rape, Transgendered, Transsexual, Transvestite, Virginity / Blowjob, Fiction, Rape, Transgendered, Transsexual, Transvestite, Virginity / By

Silk and lace Being 18 I had just moved out from home into my own place along with two other girls, Sara and Andrea. They were both really good looking, Sara being 5,8 ish with light bronze skin, full and round C cups. Sara was really fit and sporty, always wearing cotton jog pants and tops, I always find my self staring at the high top of the thong, the black against her tan always made me hard. Andrea on the other hand was very much a girly girl, dresses, nylons … all of that type of thing, always showing some portion of her pale flesh. It is hard living with these girls they are such strong sexy women, I always find my self attracted to, and recently found my self wanting to be like …

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First Contact_(1)

/ Categories: Anal, Blowjob, Cum Swallowing, Transsexual, Transvestite, True Story / Anal, Blowjob, Cum Swallowing, Transsexual, Transvestite, True Story / By

I’ll be honest; I was in the Navy at this time. I know, I know, ha ha ha. That’s a log story, not about a sexual experience. I’m not attracted to men; I love a woman’s figure, all the way. If anyone has been to Virginia, you’ll believe this. I was bored one night, and went to a bar just outside of Portsmouth, by the shipyards. I didn’t know anyone, so I sat at the bar, and just got a beer and a shot. After my second beer, and about two more shots, I was buzzing pretty good, and started to look around. There was a dirty blonde at the end of the bar still alone. She was talking to the bartender, and seemed a little upset. I figured he was family, or maybe a …

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New Start pt2 (new job)

/ Categories: Anal, Blowjob, Cum Swallowing, Fantasy, Older Female / Males, Transvestite / Anal, Blowjob, Cum Swallowing, Fantasy, Older Female / Males, Transvestite / By

My new job was in a largish complex building for the elderly called Willow Hights, it had 40 one-and 2-bedroom apartments there was a café, hairdressers and a couple of little shops on the 1st floor. My job was exactly as the job title said, odd-job man, once l got to know the residents my job became a lot more interesting. I was in the middle of putting away stores when my pager bleeped with a message telling me apartment 12 had a blocked sink in the bathroom, so l finished the job l was doing and went to 12, l knocked then heard a woman telling me to come in, l went inside and got on with unblocking the sink. Things were going well when the woman called to ask if l would help …

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Carl to Carla

/ Categories: Anal, Enema, Fiction, Gay, Transgendered, Transsexual, Transvestite / Anal, Enema, Fiction, Gay, Transgendered, Transsexual, Transvestite / By

Note:I didn’t write this. “Yea I thought the singing was OK but I don’t really go for that style too much” “And the girls?” Brian prompted me. “Oh come on Brian leave him alone we all know he’s not really interested in girls.” “Give him a chance, people can change! Perhaps Carl’s developing an eye for them now eh Carl?? I mean they weren’t bad looking. So, apart from their style what did you think of them?” I was together with Mike and Bryan and a number amongst many of my old school friends. The local pub had got in this group of country style singers. I think in sexual relations it is sometimes hard to define the difference between consent and coercion. The reader will have no doubt that in the events which follow …

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Valerie discovers me Part 1

/ Categories: Blackmail, Fantasy, Male / Female Teens, School, Transvestite / Blackmail, Fantasy, Male / Female Teens, School, Transvestite / By

This will be a first for me. I think all the stories I’ve ever written about me in panties  and lingerie, had to be about me submitting to men. This morning I remembered a fantasy I told a friend in high school about a girl I really liked.I attended a private school where we had to wear uniforms. Guys wore grey slacks, white shirts and maroon loafers. The girls wore the same white shirts and green pleated knee length skirts, knee high socks and black and white Saddle Oxford shoes. I lived a very protected life and was never told about sex, so sneaking my mom’s and sister’s panties and bras… managed to stay off their radar. I eventually rode my bike to various stores and bought my own satin bikini panties and a few nylon low …

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Somewhere in Afgan

/ Categories: BDSM, Body modification, Bondage and restriction, Cheating, Cock & ball torture, Fiction, Torture, Transvestite / BDSM, Body modification, Bondage and restriction, Cheating, Cock & ball torture, Fiction, Torture, Transvestite / By

There was a knock on my door. “Come,” I answered, “Prisoner and escort Sah!” shouted Sgt Major Riley in an ear splitting roar completely inappropriate for a small hut after an all nighter in the mess. “Well come on in,” I invited. I surveyed the biggest and ugliest Arab “Woman” I had ever seen, at least the murderous eyes and UK size 17 bovver boots which was all I could see with the huge all enveloping Berk-er it wore gave that impression. “Sah, Prisoner will advance, wait for it, Hep Tight, Hep Tight Hep tight Alt, Prisoner Sah, Gook impersonator woman Sah, Tranny Sah, Tranny wi no Fanny sah.” “I think I get the picture, “ I agreed as the surly individual glared atme through the slit in its Burkah. “Geneva convention, woman’s need to …

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sister throws a party, and catches brother

/ Categories: Bi-sexual, Fantasy, Humiliation, Incest, Transvestite / Bi-sexual, Fantasy, Humiliation, Incest, Transvestite / By

My name is Sam, I was raised in a fairly well off family, classic middle-class suburbia. We live in a single story, 4-bedroom house. The master bedroom is in the back corner, my sister’s bedroom right next to theirs, my bedroom, which is directly across the hall from Tammy’s, and a spare bedroom, across the hall from my parent’s room, which acts as a guest room/ study room. My parents don’t go away often but when they do trouble usually ensues. I have an older sister named Tammy; she is, at this time, 16. She has long wavy light brown hair, blue eyes a fair B-cup, standing at 5’4″ and slim from doing gymnastics and other activities during middle school. I’m 14, freckled ginger brown hair with the same waves and I wear my hair …

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Growing Up Chapter3

/ Categories: Anal, Bi-sexual, Boy, Diary, Female / Girl, Fisting, Incest, Male / Older Female, Transvestite / Anal, Bi-sexual, Boy, Diary, Female / Girl, Fisting, Incest, Male / Older Female, Transvestite / By

This one time, Mom dressed me up in a garter and stockings and a corset and black satin panties and also a wig, a short and silvery bob, . The stockings had an embroidered pattern and the corset was stiff and she cinched it tight but the panties were hers and so they fit me loosely with lots of fabric sliding against my skin. She sits on the bed and takes me over her knees and gently, with a lot of lube from her nightstand, works her fingers into my butt hole, one and then two. The excitement of being penetrated gets my balls all tingly. Rubbing my crack up and down with lots of slick lubrication she makes sensations zing through my body. I’m grinding into her lap and my dick feels so good …

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A Night to Herself in London

/ Categories: Anal, Diary, Toys, Transgendered, Transvestite, Voyeurism / Anal, Diary, Toys, Transgendered, Transvestite, Voyeurism / By

She’d been working hard in the lead up to this night for month’s. It takes alot of planning and discipline to look and feel as good as she did as she began to prepare. The day had been spent exercising, fasting and hydrating. As she stepped into the shower after finally finishing cleaning herself out, she sighed deeply since now the fun could start. The warm water raced down her perfectly smooth skin thanks to the full body waxing a week prior. It ran down her lean muscled back, between the shoulder blades, over the dimples above her perfectly round smooth ass, down the crack and just kissing her silky balls before dripping away. She turned to allow the powerful spray to hit her chest, massaging her nipple rings and flying down a rock hard …

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Suzy’s Daydream

/ Categories: Domination/submission, Exhibitionism, Fantasy, Transsexual, Transvestite / Domination/submission, Exhibitionism, Fantasy, Transsexual, Transvestite / By

For those who haven’t been following my “coming out” thread, I’ve spent the last few months learning to accept and enjoy my love of crossdressing. During that time, I discovered that I absolutely love going out in public in scandalously short skirts and sky-high spike heels. Even better (and amazing to me), I’ve discovered that when I do, other people apparently don’t see through my disguise! After a number of trips to stores and malls, I’ve learned that I really can pass as a woman! I won’t repeat that discussion here, because you can click the link in my signature if you want to read it. However, lately I haven’t had much of an opportunity to enjoy being Suzy because of work and family obligations. Just before those obligations struck, though, I was looking for …

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I Discover Jenna’s Secret

/ Categories: Anal, Ass to mouth, Coercion, Fiction, Teen, Transvestite, Virginity / Anal, Ass to mouth, Coercion, Fiction, Teen, Transvestite, Virginity / By

I had recently been divorced, and had just turned 36 when I decided to make some changes in my life. I had worked myself up to superintendent of an N.Y.C. commercial real estate building and I decided to go for something less stressful. I wasn’t looking for less work, just something without the cutthroat aspect and everything needing to comply with an insane amount of regulatory paperwork. After looking for a short time, I found what seemed the perfect solution. A residential complex in N.J. was looking for a maintenance super, and on top of that offered a free apartment as one of the benefits. I sent out my resume and after a follow up interview I had the job. Two weeks later I had moved into the complex and started work. The property manager …

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Our Only Hope, Chapter 05

/ Categories: BDSM, Exhibitionism, Fiction, Transsexual, Transvestite / BDSM, Exhibitionism, Fiction, Transsexual, Transvestite / By

In this chapter, the search for the Monty brothers leads W to Davenport Iowa and a club call “Colonel Boogie’s” I could have run this book through my regular publisher and made a couple hundred dollars, but I am posting it instead because many more people read my posts than buy my books. = = = = = = = = = = = = = = = = = = = = WARNING! All of my writing is intended for adults over the age of 18 ONLY. Stories may contain strong or even extreme sexual content. All people and events depicted are fictional and any resemblance to persons living or dead is purely coincidental. Actions, situations, and responses are fictional ONLY and should not be attempted in real life. All characters involved in sexual …

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DNA Chapter 3

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

Jim ran his hand over his curving stomach and probed the strange folds of his vagina, how in the name of God was a baby supposed to fit through that? Well you might get to find out, said a corner of his mind. He thrust that away, the chances of him getting pregnant were small, he decided. I’ve only had sex as a girl once and you are always hearing of couples who can’t get pregnant, he thought. In a corner of his mind a voice was saying, but what if you are? He ignored it and got dressed. He ignored the dress and wore a loose green jumper and a pair of Anne’s jeans. He noticed he was still wearing Julie’s crucifix, it looked quite nice to Jim nestled between his breasts. After he …

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