Transvestite

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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Suzy Unleashed Chapter 8

/ Categories: Coercion, Exhibitionism, Fantasm, Transgendered, Transvestite / Coercion, Exhibitionism, Fantasm, Transgendered, Transvestite / By

Despite Kathy’s warning that I’d need to be well-rested for Tuesday’s performance (or maybe because of it), I tossed and turned most of the night, as I searched for a way out of the trap I was in. By the time the sun rose and Kathy woke up, I had pretty much convinced myself that there was no way out. She sent me off to the bathroom for my morning shower and shave, reminding me that I had a big day ahead of me. When I returned to the bedroom, as I anticipated she had laid out my wardrobe for the day. The only surprise was that she hadn’t laid out the garterbelt and stockings, instead leaving a pair of pantyhose for me to put on. Of course, when I put on the skirt she …

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Life on the Ranch pt. 3

/ Categories: Anal, Authoritarian, Blowjob, Coercion, Cruelty, Domination/submission, Female Domination, Fiction, Hardcore, Humiliation, Oral Sex, Reluctance, Spanking, Transgendered, Transsexual, Transvestite, Violence / Anal, Authoritarian, Blowjob, Coercion, Cruelty, Domination/submission, Female Domination, Fiction, Hardcore, Humiliation, Oral Sex, Reluctance, Spanking, Transgendered, Transsexual, Transvestite, Violence / By

Bzzzz! Bzzzz! Bzzzzzz! Bzzzz! Bzzzzz! Bzzzzzz! Uhhhhh, I’m so exhausted. I can barely find the strength to shut my alarm off. 4 AM came quickly, my body aches from all the strain of being Amanda’s fucktoy. I force myself up. Ahhhh, my ass hurts like never before. I shudder at the memory of last night replays in my mind. What more does Amanda have plan for me? How much more can I take? Will she ever stop? Doubtful… She’s never going to stop… How can someone so beautiful be so cruel? My eyes start to water as I begin to realize this is my life from now on… I’m a slave to Amanda’s desires. As I get dress, I remember having the strangest dream…Similar to a lot of other dreams I’ve had. I was in …

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Halloween with Kym

/ Categories: Exhibitionism, Fiction, Incest, Transvestite / Exhibitionism, Fiction, Incest, Transvestite / By

My first ever story based on a fantasy that will most likely never happen… (All characters of are Adult age). I am a cross-dresser, who while I had custody of my Daughter Kym, stopped dressing. The characters are real, (names have been changed to protect the innocent), the locations are real. Only the events are made up. Should they ever actually happen, I would be very, very happy. After Kym moved away, I started wearing my pantyhose again under my pants and with a robe around the house, this was the most my wife (Kym’s step mom ) could accept. I spent most of my time dreaming about dressing again. I was soon to find an exciting and forbidden release for my desires. Halloween was fast approaching when Kym sent an e-mail asking me if …

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First Time pt 1

/ Categories: Exhibitionism, Teen Male Solo, Transvestite, True Story, Virginity / Exhibitionism, Teen Male Solo, Transvestite, True Story, Virginity / By

When I was about 5 yrs old I somehow discovered that I enjoyed women’s clothing, especially wearing them. It started off rather innocently, wearing my moms or sisters dress along with heels. I used to put 2 stuffed bears as boobs. As I got a little older I seemed to have forgotten all about this for a few years. Let me describe myself a little before we go any further. At age 15, I was about 5′ 4″ maybe 120 lbs, longish brown hair, green eyes and a very fem ass. When I turned 15 or 16, I was able to get a paper route early in the morning. I would get up about 5, load up the papers in the bag on the front of my bike and get to work. As the months …

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Jeffry and Billy 3

/ Categories: Domination/submission, Fiction, Teen Male / Teen Male, Transvestite, Young / Domination/submission, Fiction, Teen Male / Teen Male, Transvestite, Young / By

Jeffry and Billy 3 (mm, trans, dom, young) Summary – Jeffry and Billy play even more sexy games. Previous Chapter Summary – Billy invites Jeffry over to play some games. Note – This is a work of fiction, make-believe and sexual fantasy. It is not based on real people or actual events. You must be 18 or over to read these stories. The author does not condone any sexual activity among persons under 18 in real life. Also, the author does not condone unprotected sex in real life. It is OK to have fantasies, but turning a fantasy into reality can destroy lives. Don’t fuck with other people’s lives! Billy looked down at his friend Jeffry, who he had just transformed into a cum-eating slut, who was still kneeling before his softening cock. He watched …

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Straight to Bi

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

After I finished university, I struggled for a good-paying job, and money was tight. But I couldn’t face living back at home. I managed to find a room to myself in a house-share with two other guys and three women. We were mostly in our early twenties and doing various entry-level jobs. One guy, Pete, was older, about forty five. He was on a temporary assignment in our city and didn’t want the hassle of renting somewhere unfurnished. At home I had shared a bedroom with my brother and at uni I’d been in a shared room too so, even though I wasn’t alone, my own room in the house gave me some privacy for the first time in my life. That privacy, plus lots of free time away from my crummy part-time job, gave …

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Wanting to be a woman chapter 4

/ Categories: Blowjob, Cum Swallowing, Fantasy, Fisting, Rape, Transvestite / Blowjob, Cum Swallowing, Fantasy, Fisting, Rape, Transvestite / By

When the police busted through the door in the porn booth, I naturally jumped up. But my skirt was still up around my waist. The one cop said, “This whore is a dude.” As they pushed me against the wall, I said, “ What did I do wrong?” “You’re being arrested for prostitution.” “But I am not a prostitute..” “Yea, that’s why you have two ten dollar bills stuck to your ass.” They slapped the cuffs on me and started to drag me out of the porn store without even pulling my skirt down so one ten showed and my dick peeked out from under the skirt. On the way to the police station, I did not know what I would do. My mom would surely find out about me wanting to be a girl. …

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Toronto Subway Deepthroat

/ Categories: Bi-sexual, Blowjob, Cum Swallowing, Domination/submission, Extreme, Female / Girl, Hardcore, Humiliation, Oral Sex, Romance, Transgendered, Transsexual, Transvestite, True Story, Young / Bi-sexual, Blowjob, Cum Swallowing, Domination/submission, Extreme, Female / Girl, Hardcore, Humiliation, Oral Sex, Romance, Transgendered, Transsexual, Transvestite, True Story, Young / By

It was a hot Toronto summer Sunday evening when I was headed back home from spending an evening downtown with my friends. As 23-year-old junior college students we were enjoying the much-needed break from our semester exams. I was about six subway stops past the Bloor-Yonge line in an empty cart, I was seated near the doors having a perfect view of the empty seats opposite of me. The humidity was getting to me so I decided to unbutton three of the top buttons of my silk white shirt. My black, lacey bra was almost visible but given the cart was empty I couldn’t give a damn. Just as the subway came to a halt at the Greenwood stop I decided to touch up and reapply a bit of my luscious light peach lipstick to …

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I’m Ed’s cross-dressing home help

/ Categories: Anal, Blowjob, Fantasy, Role-playing, Transvestite / Anal, Blowjob, Fantasy, Role-playing, Transvestite / By

I had been made redundant and the employment for the area wasn’t great, l was in town with my wife and in an age-help charity shop was a card asking for volunteers and my wife suggested l apply as it will keep me doing something while l look for a proper job. I went inside to put my name down and by the time l got home there was a message from the shop asking me to come in for a chat. I went in the next morning expecting to be interview for work in the shop, but the volunteers they were looking for were for people to help in the old persons home, l explain l had no experience, but the woman and man interviewing me said l didn’t need any training as l …

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OUR NEW LOVERS WERE SO EXCITING, SO TALENTED

/ Categories: Ass to mouth, Bi-sexual, Blowjob, Consensual Sex, Cosplay, Cuckold, Erotica, Exhibitionism, Extreme, Female exhibitionist, Group Sex, Hardcore, Male / Females, Male / Older Female, Males / Females, Older Female / Males, Oral Sex, Threesome, Transvestite, True Story, Voyeurism / Ass to mouth, Bi-sexual, Blowjob, Consensual Sex, Cosplay, Cuckold, Erotica, Exhibitionism, Extreme, Female exhibitionist, Group Sex, Hardcore, Male / Females, Male / Older Female, Males / Females, Older Female / Males, Oral Sex, Threesome, Transvestite, True Story, Voyeurism / By

The only man she has ever had. “I realize now I have missed out on a lot in life. A sex life and sexual pleasure especially, I am naive when I compare with my girlfriends. They tell me my past sex life could only be described as vanilla at best. I need a man to educate and show me what I have been missing.” Over the following months I took great delight in educating Amanda sexually. She had soon lost her inhibitions as we continued to stretch our sexual boundaries and seek new levels of sexual pleasure. “That really was something. When can we have it again?,” Amanda asked me later that night in the bath after we had been pleasured by two men, fifteen years younger than us. “Watching that boy sucking your rock …

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Dressed To Thrill

/ Categories: Bondage and restriction, Fantasy, Male Solo, Masturbation, Spanking, Transvestite / Bondage and restriction, Fantasy, Male Solo, Masturbation, Spanking, Transvestite / By

He didn’t hear the front door open. All he could hear was his own breathing. And besides, he wasn’t expecting her back for hours, so when it did open it did not occur to him to listen to anything, except his own erotic thoughts. But then…………….. he did hear her call. “Joe? Are you home?” He didn’t reply. He was suddenly frozen in a mixture of pure lust, fear and trepidation. And he couldn’t reply anyway with the ball-gag firmly in his mouth and tied around his face. This prevented all but the odd pleasurable moan escaping from his lips. He waited for a few seconds as his mind unraveled the situation he was in and then his worst fears started to come true. He heard the faint footsteps as his wife started to ascend …

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caught in drag

/ Categories: Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite, True Story / Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite, True Story / By

My brother was 4 years older than me and had gotten married. His wife was a tall, slender girl with narrow hips, long legs and well formed breasts. I was about her size. I was a bit taller and a bit skinnier, and I had a cock that would not go soft. It seemed like I had a hard on most of my waking hours and probably while I slept, too! I used to jack off every chance I got. I could think about guys I saw in gym class, washing their tight bodies in the showers, or my sister-in-laws underwear drawer. It had all the lacy undies, bras, slips and pantyhose that felt so good as I caressed my throbbing cock with them. I know she had a bit of a thing for me …

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Growing Up chapter 5 1/2

/ Categories: Diary, Girls domination, Teen Male/Teen Females, Threesome, Transvestite / Diary, Girls domination, Teen Male/Teen Females, Threesome, Transvestite / By

… She brings me another outfit. More bondage-y. But I don’t get dressed up yet. First we invite Christine over and get drunk in my dorm room. Beanbags, pillows, blankets in a puddle on the floor. She’s in a long sleeve knit top, black of course with a Waist cinching underbust corset. Her boobs look a litte bit amazing. She’s got a black mesh skirt, long with lace and ribbon at the hem and a dark burgundy crinoline under it that flounces it out. Stockings up under the skirt and big clompy goth boots. Her eye makeup is super dark but her thin lips aren’t as heavily done as usual. Maybe she plans on kissing? We settle in with a bottle of tequila and play Truth or Dare, ’cause what better way is there to …

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Caught Stealing Thongs_(1)

/ Categories: Asian, Fiction, Interracial, Spanking, Teen, Transsexual, Transvestite / Asian, Fiction, Interracial, Spanking, Teen, Transsexual, Transvestite / By

It was so humiliating. A store security guard caught me walking out of the department store with a pretty, expensive French bra, garter belt, panties and stockings set. I was ushered into the office of the store’s chief of security. I was scared. I was a teenager. It was the first time I had ever been in trouble. But I couldn’t help myself. I’m pretty and I like to wear pretty things. I couldn’t afford the lingerie, but I didn’t need to steal it either. I don’t know what possessed me to do it. Perhaps it has something to do with my secretive nature. I have so many secrets. My whole wardrobe, actually, is a secret that I keep hidden until I find an occasion for dressing up. Likewise, my make-up, my perfume, heels,the falsies …

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Uncontrollable Pt. 2

/ Categories: Anal, Cum Swallowing, Fantasy, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite / Anal, Cum Swallowing, Fantasy, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite / By

HI GUISE. I’m back with my first Part 2! This was kind of spur of the moment, inspired by my own tastes, as well as some of the great comments I’ve gotten! So I hope you enjoy. I certainly did. I gave it a good scan for editing, but there are sure to be occasional mistakes throughout; hope they don’t detract from the goodness, and I hope my words get you off. It was the eve of Halloween. My friends, their friends, and I were all getting ready to go to a midnight showing of the Rocky Horror Picture Show, hanging out in our apartment until it was time to leave. It had become a tradition, and we were lucky, in such a small town, to get a showing. Kayla wore some kind of slutty …

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The Transformation of Jesse

/ Categories: Anal, Ass to mouth, Blowjob, Cum Swallowing, Fiction, Gay, Romance, Transvestite, Virginity / Anal, Ass to mouth, Blowjob, Cum Swallowing, Fiction, Gay, Romance, Transvestite, Virginity / By

This is only the third story I have ever written so please only helpful criticism. I hope you enjoy. Jesse was like every other guy he knew. He liked sports, hanging out with friends, getting drunk and the company of a good looking girl. He was a sophomore in college and constantly in the company of beautiful women, both in and out of the bedroom. He lived alone in his own apartment which made it very easy to bring home a cute piece of ass from the local bar or house party. As the number of girls coming and going increased, Jesse began to get bored with the typical sexcapades that took place in his life. He soon found himself searching the web for new and exciting thrills to get him off. He had never …

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Life on the Ranch pt 1

/ Categories: Anal, BDSM, Bondage and restriction, Discipline, Domination/submission, Fantasy, Female Domination, Hardcore, Humiliation, Job/Place-of-work, Non-consensual sex, Rape, Transgendered, Transsexual, Transvestite, Violence / Anal, BDSM, Bondage and restriction, Discipline, Domination/submission, Fantasy, Female Domination, Hardcore, Humiliation, Job/Place-of-work, Non-consensual sex, Rape, Transgendered, Transsexual, Transvestite, Violence / By

I can’t believe those jerks threw cattle dung at me. No good, dirty rotten, a-holes. They got that shit all over me. That’s not even the worse part… Well, that’s up for debate. But to top it off we’re out of hot water! I had to wash the bull shit off with freezing cold water. I hope to god Steph gets back soon. I wish I could tell her what those jerks did, but I know we’re in desperate need of help. I don’t know how much longer I can take their crap. Always calling me all sorts of derogatory, crude, insults. The owner’s daughter or princess are their favorites, knowing full well that I’m a boy. Pillow bitter or mattress muncher are some other terms I’ve heard them call me, especially Bruce! Honestly I …

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STRETCHING OUR SEXUAL BOUNDARIES.

/ Categories: Ass to mouth, BDSM, Bi-sexual, Blowjob, Cheating, Cuckold, Cum Swallowing, Exhibitionism, Hardcore, Lesbian, Masturbation, Mature, Oral Sex, Spanking, Threesome, Transvestite, True Story, Voyeurism, Written by women / Ass to mouth, BDSM, Bi-sexual, Blowjob, Cheating, Cuckold, Cum Swallowing, Exhibitionism, Hardcore, Lesbian, Masturbation, Mature, Oral Sex, Spanking, Threesome, Transvestite, True Story, Voyeurism, Written by women / By

“Tell me more, I am intrigued.” Minutes later I am more than intrigued and ask Lu Xi to make it happen after she told me, “Let’s stretch the boundaries, a foursome, Carla for your man and me for you.” I had recently watched Lu Xi blowing my man while I had two men pleasuring me, though she had never even laid a finger on me, so the thought of her providing sexual pleasure for me has great appeal. And perhaps me pleasuring her in return. My man and I have never seen her naked, something I am looking forward to. On a lazy, slow Tuesday afternoon, just the type of day for unhurried erotic sexual pleasure, we are back in the familiar surrounds of Lu Xi’s hotel honeymoon suite. My man Charles is expecting some …

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