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Crossdressing

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The Day My Secret Was Discovered

My wife surprises me.

My wife and I have been happily married for four years. She is the dominant one in this marriage. Just recently I have discovered how much I enjoy wearing women's clothes. I love how the panties feel between my ass cheeks. The silkiness of the nylons on my legs as I slide them causes an erection every time.  My wife had no idea until one day when I had Friday off from work. As soon as she...Read On

30

Teenage CD Awakening Part II

A teenage boy widens his crossdressing horizons by starting to wear his mother's clothes

I had crossed the Rubicon. I had tried on my sister's panties for the first time. Now I felt guilty. Incredibly guilty, and dirty. I went to school as normal the next day, but despite the guilt I couldn't get the amazing thrill of trying on that little pair of blue and white striped cotton panties out of my head. As 3.30pm and with it the school bell neared, the overwhelming urge to do...Read On

26

My Best Friend

My friend's reaction to me dressing as a girl caught me by delightful surprise.

I always wanted to be a girl. Every time I saw those pretty girls prancing around the college campus I’d become green with envy. Their feathery skirts caressing glossy thighs. Long, silken hair cascading across bare shoulders. High heels clicking on the pavement as they paraded their fit asses in front of all the guys. They were allowed to be sexy, and no one would stop them. And the warm...Read On

7

Susan is Complete

Love of pantyhose turns me into Susan

Like most of us, my cross dressing started with wearing pantyhose. This is a true story. My older sister (she was 14 and I was 9) would wear them to school (private school with uniforms) everyday. She started to notice that I would stare at her legs when she wore them. To this day I don't know why, but she would tease me trying hard for her not to be obvious about it, letting her skirt hike up...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

22

My wife catches me cheating then takes a year long revenge

completely and finally a girl

Where to start? This is my favorite fantasy. I just got married two years ago, and my wife caught me cheating with her best friend. At first she was enraged and didn't speak to me for three weeks except to insult me, with constant references to my very little dick and what did Carol see in me but to hurt her? If I had understood how women feel, then this would never had happened! Then like...Read On

30

Friend's Treat

A divorced man gets a treat

I had recently split with my wife and was feeling very down. I was invited to spend a few days with my old friend Dave and his wife Tracey. The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse. I...Read On

25

Bookstore Crossdressing

Giving Up My Butt-Cherry

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. ...Read On

Mistress Hannah's Pathetic Husband Part 2

The transformation begins

During my first week as her new slave, Hannah decided that I was too hairy for a little sissy boy, so I had to begin removing hair from the tip of my nose down. The mustache went first. It really was kind of pathetic anyways. I actually got compliments from some of the women at work about how handsome I looked without it. I had grown it because I had a "baby face" and I wanted to seem...Read On

30

Seducing Uncle Frank

A tale of a Crossdresser seducing his attractive Uncle.

This is a story that happened some time ago, when I seduced my Uncle Frank. Uncle Frank Uncle Frank was married to my mum's sister. He was about 10 years older than Aunt May, and it was both their second marriages. Uncle Frank had an Italian father, French mother, three older sisters, loads of nephews and nieces, and had property in Kensington, the Algarve, and Telluride. You could say he...Read On

18

The Feminization of Michael - 2

The Feminization of Michael. Chapter 2 I continued with the “weekend” clothes for another few weeks and consistently had people commenting, laughing and making things difficult when I was out shopping. I continued at work in the more feminine suits and blouses too.  The rumours increased and somehow word had got around that at the weekend I wore dresses and full make up! This couldn’t...Read On

12

Losing at Strip Poker with Three Women

Oh my god, what did i get into?

Well, last night was quite a night to say the least. Three girl/friends came by with wine coolers and tequila to do a little partying. The four of us have been very tight for over fifteen years. We are very special friends that can talk about anything to each other. I should have known they were up to something when they said the tequila was all mine and the coolers theirs. They know I...Read On

49

Neighbor fun

Slutty fun with neighbors

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and...Read On

11

Fulfilling A Girl's Male Fantasy Part 2

Jenny and her friends have a party with a surprise.

Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a couple of months after our first encounter, we were both in her room talking and listening to music. ...Read On

22

Punished

A crossdresser finds himself punished.

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in...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

24

Prom Date- Part 1

Jody is forced to dress as a girl for prom.

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful....Read On

23

Halloween Fun

First time Out

My friend talked me into dressing up as a female this Halloween. It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back. It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing...Read On

24

Nights in pink satin

Forbidden desires are allowed to awaken.

It finally had happened. Paul couldn't resist the urge anymore. The urge to wear women's clothing. The urge to be degraded and humiliated. The first thing he had done was to have a shower and remove all his body hair. Gazing at his naked self in the mirror, he was pleased with the results. Forcing down a shudder of anticipation and excitement, he reached for the first garment. The feel of...Read On

12

A weekend with Nancy

It was staggering to think that it was only 8pm and Nancy was to be with us the entire weekend

  CHAPTER 1 Upon arriving home from work one Friday afternoon my wife informed me that the kids would be staying the weekend at some friends house, and that she had made some special plans for us. She then went on to say that she would be gone for a couple of hours and that while she was gone I was to shower and to shave myself from head to toe. Then I was to get my...Read On

29

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

62

My First Boyfriend - Part One

I learn to cross dress and get a boyfriend

Since my family had moved to our new house, Steve and I had become best friends. He lived next door and had moved in about a month before we did. With both of us being the new kids on the block we bonded quickly. He was two years older than me at eighteen and I had just turned sixteen a few months back. He was also taller and had more muscles than I did. He had tan skin and black hair where I...Read On

13

Adventures in a Woman’s Body – Chapter 4: Public Humiliation

Used as a playtoy at the mall

I stepped out of the shower and began to dry myself with a towel. On this bright Monday morning, all I could think about was what happened on Friday night. After being gangbanged and cumed on thoroughly, Daddy drove me home that night. On our way there, he explained to me the situation that I am in. Daddy took out his phone and showed me pictures he had taken of me being a dirty little whore....Read On

37

Chrissy's First Bookstore Trip

Chrissy's First trip to an Adult Bookstore Arcade

After my first night dressed up like a girl in my very own clothes I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the sexy feeling of the panties on my cock and the nylons on my legs. By now I had purchased quite a few women's clothes. I had all different colors of matching bras and thongs, I loved the way the...Read On

9

Dressing up

For some reason, guys like me in a dress

This is a series of stories rather than one story. It talks of my experiences as a crossdresser. My first experience as a crossdresser came as a teenager when I tried out some of the clothes belonging to a woman who was staying at our home. She was a gorgeous French woman with very pretty clothes and I did enjoy trying them on, but primarily as it got me closer to this woman who...Read On

17

Surprise at Girls Night Out

Cassie's Encounters in New Jersey

Surprise on Girls Night Out in New Jersey I explained in an earlier story that my life took a strange turn when I turned forty. I had not been cross dressing for many years, but I had the urge again to bring out my alter ego and the urge was stronger than ever. I really prepared for Cassie, short for Cassandra (I also go by Sandy) by taking a year to buy all the things I needed and get...Read On

A Little Naughty Fun When My Wife Is Away

A little wicked fun

When I was in high school, I always loved to dress in women’s clothes. The problem is I'm a guy. Whenever my mother was out, I'd always go into her room and try on her intimate apparel. I just loved how it felt on my skin. I'd especially liked how her bras and panties felt. I loved to get dressed in her dresses and even apply make-up. I really never told anybody about this. The lacier...Read On

30

All the Way (Part 1)

Kathy makes Richard pay the price

I'd only been married a little over a year when my wife came home early and found me jacking off using a pair of her panties and to be sure, this wasn't the first time. There I was lying in bed with her wispy little nylon panties wrapped around my dick and cumming like nobody's business. I was so wrapped up in my own pleasure that I hadn't even noticed her standing in the doorway watching me. ...Read On

14

Becoming an Escort

The nights second cock spurted hot sticky cum on my face and I greedily pushed into my mouth faking my enjoyment of that bitter taste. My “lover” dressed and left the room. I lay back on the bed where two men had fucked me that night and pondered how I had got into this position. Despite myself my cock was rock hard in its silk panties stained with my own cum. 3 weeks earlier I had told...Read On

14

My First Cock

My cousin's Suprise for me

I am now Staying with my cousin after my previous story so I can dress up as much as I like.  my Birthday was coming up soon and my cousin said she would have a celebration all weekend for me as it was during the week she said this would be my entrance into womanhood.  It finally arrived this weekend I thought would be the best I just showered shaved what body hair I had off then left...Read On