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Crossdressing

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7

My Good Friend Pete

A background into our relationship with Pete.

My history with Pete goes back twenty five years, and for most of that time, he has known of my penchant for crossdressing. He also knew that I'd worn most of his wife's wardrobe, and of my preference for the contents of their laundry basket over Annabelle's underwear drawer.  Pete played the leading man role in many of my wife's fantasies. Tall, dark, and ruggedly handsome, who could...Read On

8

Call Me Julie Part 4

Julie is not the only one in for a surprise.

Scott coaxed me out of the car and we walked the ten feet to the front door, he was practically dragging me while reassuring me that everything would be alright. "Kelly is expecting us, don't you worry about a thing." "She is expecting me? Dressed up like this? Somehow I don't think you are telling me everything Scott, if this ends badly I will be kicking your sweet ass," I told him. ...Read On

9

Well Fuck Me Backwards!

A tale of a confused crossdresser.

The first time my wife Victoria went on holiday with Annabelle was around three years ago, not long after she had separated from Pete. They had been two of our best and closest friends, and it's fair to say we were upset when Annabelle broke the news of their split. She and her ex-hubby have been privy to my crossdressing habit for over twenty years. During that time we have, all four of...Read On

5

Jessie's Office Interlude with Sue

As Jessie's first date with Sue ends, now it cums down to the office...

I could not believe what a great time I had on my first date with Sue. Her planning was impeccable. From getting caught at the department store, to my new set of lingerie and clothes, and then a feminization session at the salon. Only to wrap this up with a surprise sexual encounter with Sue, her male friend Quenten, and all whom I met at the various retailers. It was a first date that I...Read On

10

Once Again in silk, The Conclusion

Darlene meets Melissa

As soon as I got home from the gym on Sunday, I headed to the closet and removed all the boxes containing Melissa's things. They had been cleaned and packed with great care so they looked as good as the day they had been purchased. I then inspected the makeup case and its contents seemed to be in great condition as were the contents of wig case. When Darlene said she wanted to meet my...Read On

2

My 2 AM Phone Call (Part Two)

I became a perfect motel whore that night.

My day started around 2:00 a.m. with a phone call from a Black man I knew from an intense relationship that started in a video store theater several years before. After using me as he pleased for several months, he suddenly dropped me and just vanished until this morning when he called and gave me very specific instructions where to come, what to wear and when to arrive. That is why I...Read On

0

Becoming John Collins' Mistress - Part Two

I'm invited to spend a day with one of John's hunky friends

The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me. I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out. Joe was making eyes at me during the drive, and I decided it would be best to come clean. “Joe, there’s something you...Read On

9

Jessie and Sue's date concludes

Jessie's date with Sue cums to a wild conclusion!

I could not believe I was going out with Sue on a date. It was our first date and she appeared to be my match made in heaven. First, we got caught with my face between her thighs while wearing lingerie in a department store dressing room. Next, we made our way to the shoe shop where not only did Sue buy me a killer set of four-inch heels that were strappy, brown open-toed sandals with...Read On

11

Carl, Carla and Hannah - Part 7

Claire starts work at the office as Carla continues her voyage of discovery into femininity...

I switched the six-thirty alarm off with a groan and turned to cuddle Hannah. After our customary two minute huddle, I kissed her and then wearily got out of bed. Without thinking, I sat down on the toilet and relieved my bladder, and then took off my bra and panties before stepping into the shower. The soothing warmth of the water managed to ease some of the ache in my body from the...Read On

10

The Magician's Assistant or How it began - Part 1

Ken had led a pretty normal life until the year his longtime friend needed an assistant for his growing magic act. Magic had always been a hobby with his buddy Carl and he spent many a day watching him perform a new trick in his garage seeing if he could detect the secret. Their being forced to take woodworking classes in high school really paid off when Carl expanded into the realm of...Read On

7

Carolyn Makes Her Way

After getting fired Carolyn moves in with Mike

After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long...Read On

10

My First Night Chapter 2

The second chapter to my night with Marie

Previously She also included in this bundle of sissy goodies, sheer black thigh high stocking and black three-inch wedges. My legs were so high and my body so curvaceous, my soft red lipstick tied in with the red baby doll. She had placed a blonde wavy wig which I tied into my hair with grips and styled with a middle part-in. Marie also supplied red nail varnish and some very...Read On

9

Crossroads Ch.3

He has to find out if this is what he wants

A tale of pure fiction and fantasy. I was actually considering going all the way. Going all the way in becoming female. I had been living as a female in all phases of my life for some time. I continued on the hormones and all my desires said I should do this. I had called the plastic surgeon who had done my breasts and explained what I wanted. She suggested going to see a doctor...Read On

8

slut on the town

I got put in a full nelson the other night by a naked black guy. It happened in a video preview booth at Corey's Adult Video store in Oakland. I had been hanging out in the arcade, wearing just a black two-piece string bikini, and a pair of fire engine red high heels. I had been there for about a half hour, but I hadn't seen anyone. But it was early, only 3.30 p.m. Then I heard the buzzer go...Read On

9

Fantasy Meets Reality at the Peep Show

A crossdresser's fantasy comes true

I pushed my way through the purple curtain to the cashier’s booth. He looked up from his newspaper and asked me how many tokens I wanted. I figured a stack of twenty would be enough to complete my mission. I’d been there several times before but this would be my first time taking things further. My heart was beating fast as I scooped up the tokens and made my way to the viewing room. As...Read On

10

The girl with green hair

An extra-special birthday surprise

"Is this cab taken?" Languorously, she lifted her green mascara-clad eyelids and gave a half-smile. "'Fraid so." I'd left the party in the local wine bar and decided to get home before I passed out. I was feeling pretty squiffy. Two taxis cruised by with their engaged signs on. It began to spit with rain. I looked through the back window of the parked cab. The interior light was on....Read On

13

Exploration (Discovery II)

Shauna's second lover.

After my neighbor, Jack, caught me dressed and made me his girl, my mind was awash with conflicting thoughts and emotions. I had been dressing as an added thrill to masturbating for years, and had fantasized about being with a man, but always considered it just fantasy. I never thought of actually doing it, but now, it had gone from fantasy to reality in just a few hours. Not only had I...Read On

13

A Night of Firsts pt 1

So many firsts for a shy gurl while traveling

'Oh my God, this was the night,' I thought to myself. 'I'm finally going to go out dressed.' I work for a small company and get to travel a bit, but I've really only dressed in hotels when I could drive as flying with all my things makes me really nervous. The idea of me and a travel bag being examined and having a stranger discover my femme things just didn't do it for me. However, this...Read On

9

Porn Star Babe: Part Two

Time to get the lttle sluts on the set for some hot tranny action.

Being a sexy girly boy about to make her debut as a porn actress with two handsome, well-hung studs was so exciting to me. And having my friend, Chrissie Licks, along to show me how it is done was especially re-assuring. Chrissie and I were naked and about to get into our sexy lingerie for the shoot when Summer Cox, another hot tranny porn star, came to help us with our hair and make-up....Read On

6

Christina and Cheryl - Part 3

Christina encourages Cheryl to go out with a little help from her friends...

I woke up naked being spooned by Christina. Her smooth arms held me tight against her. I turned around and woke her up with a kiss. She opened her eyes and kissed back before pushing my head down. I kiss down her body and slipped her pink panties off. I kissed up her thigh and edged closer towards her clitoris, this is how we spent most mornings. "No, my ass." I lifted her legs allowing...Read On

16

First time for 'Everything'

First time out crossdresser gets lucky with trucker.

My story is like so many I have read before and which I only fantasized about, till now. This story is all true. I thought about embellishing it to make it sexier but thought I’d let you know what happened just as it did. A short history of me and dressing up first. I have been crossdressing for as long as I can remember, from sneaking a pair of my sister's knickers, to sneaking into...Read On

4

Have A Good Feel, She Loves It! Part One

First of four parts, PaulaTVxxx the transvestite slut arranges to meet some new friends.

I initially came across David like so many other people I know on the scene whilst fishing around on the internet. Unlike many though, he was 100% genuine, he’d read my profile on the transvestite contact site with interest and taken the time to write to me. It was a well thought out message that consisted of real words, put together in sentences with no text speak. I liked him for that from...Read On

12

My Good Friend Pete (Part 2)

In order to enjoy this story, I advise the reader to read "My Good Friend Pete."

From where I stood, I could hear the crunching of gravel under Pete's feet, as he made his way to the front door. I took half a dozen deep breaths, waiting for the doorbell to ring. I didn't have to wait long. "For fuck sake, pull yourself together man." I actually caught myself smiling in the wall mirror. "...or is it woman!" One of the most difficult things to achieve...Read On

6

CD Domina training two slaves

CD Mistress commands two slaves for a hot 3-way.

Just five days had passed since my last session with my slave Candy and already I was yearning for his sexy body again. I was in need of another meeting and had something special planned for it. I called Candy's phone and just like previously he answered before it could ring twice and greeted me anxiously. "Hello Mistress Cheyenne," Candy said as he answered his phone. "Hello slave Candy,"...Read On

6

Sexy Stewardess on a Hot Flight: Part Two

The hot flight continues for Courtney.

My trip to Catalina with a handsome pilot and two of his friends turned out to be a working sex vacation for me. So far, I had already given a great blow job to the pilot, Phillip, on take-off. Then I sucked off his friend, Harry, who also sucked on my titties and played with my clitty dick through my white lace panties. Now, I was ready for the big prize, sucking Dick's big ten inch man tool...Read On

11

How Andrew became Andrea Part 3

Andrew leaned back on the couch feeling the warm cum had just let loose in his panties beginning to cool and a stain become visible on his slip. "Looks like you will have to clean up and change," Lacy said with a smile. "Looks like," Andy responded. "Shall I pick out something or would you like to?" "I would like you to." Andy headed to the bathroom where he removed his cum...Read On

7

A Nanny Femtastic - 3

A NANNY FEMTASTIC! Chapter 3 ..That night me and the girls celebrated, I was about to start work at last next week! Ok as a woman but I kind of liked the idea more and more! The weekend passed quickly and I packed all my new wardrobe into a couple of large suitcases ready for the new start at  Hanover House. I was to be dropped off on Sunday evening and was to have dinner...Read On

17

Becoming Chloe - Part 7

Vickie and Chloe go for a ride...

I awoke to find the bed next to me empty. Disorientated, I turned over and dozed until I'm awakened by the smell of coffee and Vickie walking through the door with breakfast. All she's wearing is her thin bathrobe, through which her full breasts and nipples are clearly visible. Her hair is dishevelled and she has the most wonderful smile on her face. She looks adorable. "I thought you...Read On

5

Lovers in the Afternoon

Once upon a time, on a quiet afternoon.....

Through the scrim curtains, the soft afternoon sun lights the room with a pastel glow. I sit at the chair in front of the dressing table, quietly smiling to myself. I finish putting on my make-up; a light touch of lip gloss. I look at myself in the mirror. Quite good I think. I am getting better all the time. I can feel the tension and excitement in my body. My perfume fills my head. My...Read On

14

A Nanny Femtastic - 5

A NANNY FEMTASTIC! Chapter 5 ... I looked gorgeous now with my ample breasts and thin waist! I would really enjoy this upcoming holiday! The electrolysis treatments had continued, and I now was pretty hairless and did not need to shave or wax. I did however remove all my pubic hair and became obsessed with having a completely hairless body. This included around my scrotum...Read On