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Crossdressing

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12

Exploring Even Further

Shauna meets Jerry's wife and things get heated.

For the rest of the week I was a total wreck, dreading, craving, anticipating, and fearing, the arrival of Jerry’s wife and Rocketman69, whose real name I'd discovered was Jim. Just thinking about all of the possibilities had me literally trembling with lust and, at times, fear. Jerry, too, was in a constant state of arousal. Neither of us could believe what a slut I was becoming. After work...Read On

37

Carlos and The Garter Belt

Carlos finally takes the plunge

Carlos sat in the car for a moment looking up at the sign of the sex shop. He had been in the shop on more than one occasion. A lubricant here and a toy there, to spice up the bedroom with the wife. This trip was not for that purpose. Every time he was in the shop, he was drawn to the lingerie section. In the past, when the sales girl would approach, he would say he was just looking...Read On

25

The Change Up - Part 2

Deedra has her first date out and meets new friends

I watch Emily get into her car and drive away. My mind just can’t believe what just happen. The clock on the wall says 5:00 oh my. I only have four hours to get ready. I am opening the packages that Emily drop off for me, the dress looks utterly gorgeous, lace and beading should be outstanding on me. Next the shoe box, the phone rings, looking at the caller id it's from India . I snap back...Read On

25

Mariah... My Wank Mistress

How I met Mariah, a crossdresser's dream...

We first made contact about three years ago, on one of those dirty dating sites. I was showing my tranny profile, Velvet, at the time, and was being hit on by a bunch of dirty old men, when this "Mariah" person said, "Hi." I was in a pretty sarcastic mood at the time, and was slightly peed off, as the guys I had been chatting to were only interested in one thing, getting their rocks-off. ...Read On

25

Terry Gets It In The End

Terry's girlfriend finds him in panties and leads him down the path.

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and...Read On

11

Crossroads

A young man explores his feminine side.

A crazy little story where a young man finds out if his hidden desires are what he really wants. This all started with my desire to see what it felt like to have big breasts. That's a little odd for a guy. I was a normal heterosexual guy who dated some in high school and now that I was in my mid 20's I found myself at a crossroad. A couple of years ago I had decided to...Read On

11

Trio

A secret assignation in a country hotel turns into an unusual menage a trois

Dusk. As he turned off the highway into the country park hotel, Nick was relieved to note that its car park was barely a quarter full. Pulling his overnight bag from the back seat, he headed for the brightly-lit reception lobby. A giggly gang of women were disembarking from a mini-coach. Most were clearly very drunk. In the hotel's spacious lobby he quickly spotted Mark,...Read On

11

Weekend Discovery 2

Simone's eyes grew wide when she realized that the stunning blond she was sitting next to was, in reality, her boss and the object of her most intimate desires. Now she had seen transvestites and drag queens before, but none of them looked this good. She was sitting just mere inches away from his face and still couldn't see any trace of Andrew Lippincott. Without warning Andrea leaned...Read On

11

Stranger Fuck

A crossdresser is pegged in a sex club.

  I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their...Read On

11

Who is Bella? - Part One

Velda struggles to know if her boyfriend is what she really wants

It all started after a couple of week’s dating. I was nineteen at the time, and Velda was twenty-four. I knew she had strong opinions and was quite determined to get her way. She had spoken several times about women’s rights and how she felt that the balance of power between men and women had to change. For the most part, I could only agree with her. At times she seemed a little aggressive...Read On

11

Dan into Danni pt3: Sex as a girl with a girl

Lucy gives Danni the best orgasm of his life... as a girl.

Back at Lucy’s room, Dan put down the dainty bags of lingerie and girly clothes that she had bought for him. He had been totally and magically transformed into a girl for nearly a whole day now, and every moment was a thrill. He was ultra-conscious of his body - especially his gorgeous 32C boobs, firmly held in the bra that had turned him into a curvy and sexy girl in the first place. ...Read On

11

My new persona. Becoming a girl!

Transformation from boy to sissy

I had just moved into my first apartment and needed to work out how to do the laundry. One of my neighbors had said there was a shared laundry room at the end of the corridor so I grabbed a bag of dirty clothes and threw on some shorts, a t-shirt and flip flops before heading down there. I walked into the room and started looking for a spare machine when I noticed a basket of ladies...Read On

88

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...Read On

65
Audio version available

In My Panties!!!

Sarah discovers Larry's secret.

Larry and Sarah were your typical yuppie couple working two professional careers. Larry a techno wiz was the research and development department head at a local manufacturer while Sarah was the office manager at a local Saturn car dealership. Their weekends off work were filled with their hobbies of camping and outdoor fun. Both loved nature and enjoyed their time together on beaches and in...Read On

55

Little Black Dress

The events were all the result of a lost bet.

I pulled in the driveway, and saw that my wife was already home. My thought was that she’s home early. I unlocked the door and went in. A few feet inside the door was my work stool with a box on it with a note taped to the top. I opened it and started to read. Hun, I’ve decided that tonight is the night I want to collect on our bet. You are to follow...Read On

45

Summer dressing

Long hot summer for crossdressing student doing vacation job

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with...Read On

33

My Girly Fantasy

A night with my friend changes everything between us

I wake up and smile, remembering where I am and who I'm with. I'm warm and comfortable, wrapped in your arms as you sleep. I think back to last night, finally showing you my girly side. We've been best friends for ages but I always had a crush on you. Finally, drunk on wine, I decided to do something about it. I came into the living room we share and straddled you; taking off my robe to...Read On

33

First Night Nerves

Nervous Tim becomes Tina and loses her virginity

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than...Read On

22

First Time With A Crossdresser: Part 1 of 2

Scott looks for something different after his divorce and finds Jenny

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on...Read On

10

The perfect day...

A t-girl's experience of getting dressed for ACTION!

The perfect day… The time was drawing near. He would have the house to himself! The realisation of a whole 4-month's planning would now come to fruition. It had been a while since he had gone out all dolled up, and now was a fresh opportunity to see his progress as a woman. He had been busy – his make-up collection had swelled considerably, and the addition of several choice pieces...Read On

10

Girls Night Out Part 2

Cassie and her friend's evening continues

Girls Night Out Part 2 Well everyone wants to hear about the second part of my night with Julie when I was in New Jersey. In case you didn’t read my first story, my name is Cassie, short for Cassandra (I also go by Sandy sometimes) and I am a cross dresser (CD). A while ago I was spending a hot summer night in New Jersey at a hotel with my friend Julie. We were attending a girl’s night out at...Read On

10

A weekend with Nancy: part 2

Nancy, that was the best blow job I ever had, she's awesome, Dan replied.

 Nancy informed Alice that she would be using the bedroom to dress me, and that she should pick out an outfit consisting of no fewer than seven articles, gather her make-up and whatever else she required and then use another room to get dressed. Furthermore, Nancy informed Alice if she didn't like what she was wearing when she returned that she would be punished, and to not waste any...Read On

10

Suzie and Cindy are taken to their first gay club

this is my fantasy life

As Cindy walked into the room with the outfit I picked for her, she had a distinct glow of a satisfied girl. Harry and Jack added pink nail polish, matching garter belt, thigh high fishnet stockings, jewelry, high heels and they cut bangs into her hair. She really was pretty. The three of them stood there while I was still riding Joe's cock, he was in no hurry. I must be becoming a good...Read On

10

In Her Shoes Part 3

This is the final part so please read both other parts to this story to understand it fully.

I guided Peter into the main shopping mall in town leading him straight into a shoe shop. The girl in the shop fetched a few pairs for me to try on and I relished asking Peters opinion. He tried not to look too obvious that he was hooked on my shoes and feet. I 'hummed' and 'ahmmed' a short while, telling the girl I was undecided and may well be back later. Grabbing his arm once more we...Read On

10

How to Treat a Lady

A pretty crossdresser learns how to please a man.

Being a pretty, petite, believably passable crossdresser makes me a very happy person. I have been dressing up as a sexy girl while daring to go out in public for the past two years since I was sixteen. I have had this urge and desire to dress as a female for as long as I can remember so I have gradually come to accept that I have a feminine side that needs to be nurtured and encouraged. I...Read On

10

The Pool Man

I fucked the pool man

It had been several months since I moved away from the big city. It was hard moving to a city with not a lot of people I could hang out with or be with. I had become really good at dressing up and having anal sex, but was becoming more and more restless of not having a regular, daily thing with someone.  I began fantasizing about being with the pool man. He was always friendly when he came...Read On

50

The Panty Princess

Dominant girlfriend discovers her love for submissive boyfriend

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. ...Read On

48

Telling Mom I'm A Crossdresser Part 2: The Adult Store

Missy goes out and meets her first gloryhole. Please comment and rate all of my stories. :)

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived.   It was just past 9am when I heard...Read On

37

Two girlfriends have a couple over for a fun night

Wife sets up night for us to be girlfriends, then invites another couple over for fun

My wife Dawn had surprised me by saying we were spending the night in as two girlfriends, laying out my clothes so we matched. Then after having amazing sex, Dawn surprised me by telling me that she had invited her friend, Maria, and Maria’s husband, Mark, over for some fun with the two of us and to fulfill the fantasies of all of us. So I was standing there with my red plaid skirt,...Read On

30

Tammy, Lisa, and Karen part 2

Man discovers his fantasy with more than one woman.

Please read "Tammy, Lisa, and Karen Part 1" first. I walked out the store looking at the bag of lingerie in my hand and my cock was so hard, I could barely walk. Lisa wanted me to be pretty for our date. I only had some lipstick and eye shadow at home; I needed to figure out how I was going to make myself pretty for her. That's when I walked past the the answer, but could I really do it? ...Read On