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Crossdressing

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46

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

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

23

Aunty's New Girl

Falling into the strange world of Aunty Trixie...

This is the continuation of Tickets Please! Shakily, I keyed in the URL from Trixie's card, my mind in turmoil, heart racing as her sweet gift seeped from my aching pussy and soaked into the lacy panties I was wearing. I was wedged behind one of the 'tables' thoughtfully supplied for the busy passenger. You know the ones, if you move a fraction either way you end up concussing your...Read On

21

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

28

A surprise helping hand

Getting caught paid off, in more ways than one

When I initially started to cross dress I would borrow things from those around me. At first it was my sister, then when I visited my father I would wear my step mother's things and eventually my girlfriend's. Mostly without their knowledge, of course. I was always as careful as I could possibly be, replacing things just as they had been left and making sure I had plenty of time when I...Read On

48

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

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

10

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

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

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

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

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

23

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

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

41

My Wife's Thong

Mike wears his wife's panties to win a bet

“I don’t see what the big deal is. You look so sexy in them!” “You do know what a thong is and how it works, right? It might as well be called ‘automatic wedgie underwear.’ I don’t really like walking around all day with a string up my butt just so you can get worked up by what kind of underwear I’m wearing when you’re not even around for it!” She wasn’t angry, but she did sound a...Read On

61

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

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

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

From One To Another-Part 2

two sides of a chair

I rushed into my new consignment shop job, the one that Allison had help me get. The shop was actually a duplex. One part Mary's home, the other her shop. I was a few minutes late and apologized to Mary Elle the owner. Telling her that my Biology teacher was on my case about missing assignments and had kept me after school.  Mary Elle looked at me and suggested a nice warm shower to help...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

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

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

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

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

26

Two girlfriends stay in for the night

Wife pleases her girlfriend then tells her whats going to happen next

The other day I came home from work and was looking forward to spending the evening with my wife. We had the next day off, and it was going to be great to just get some time with her. After I was home and settled my wife Dawn came and found me and told me she wanted to spend the evening with a girlfriend and have some fun. I was a little disappointed, but a few seconds later, she told me...Read On

59

Discovery

The neighbor makes a discovery

How did I end up in this position?  This was the thought running through my head as I lay face down across the bed. My mind flashed back to the moment it all began. It was a beautiful Sunday morning with a cool springtime breeze blowing through the open window. I was cleaning the house. I hated cleaning, mostly because it is never fully done. No matter how much cleaning you do, there will...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

36

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

28

How my Best friend gave me what I always wanted

My Best friend discovers my naughty little secret

The day started from me being all alone in the house for a full day. My parents and sister were out and wouldn't be home until the next day. I decided that I would give my best friend a call and get her to come over to see me, we hadn't seen each other in quite some time. She was just as eager to see me as I was her and we were both very excited as we really enjoy each other's company. Now...Read On