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Crossdressing

2

The Secretary - Part 2

My first day as the boss

I arrived at Michael's office a few minutes before 9am. Being that he rented a small space with many other companies sharing his floor alone it was a a hive of activity. People arriving for work, bustling past each other, shouting greetings, enquiring into weekend activities. I received a few smiles and polite greetings as I walked through the corridors, as well as a few winks and impolite...Read On

6

Leslie becomes the man of the house and I his princess

I learn to love being a girl

Now every night I'm being fucked by Leslie, and everyday I'm the woman of the house. Leslie starts by tutoring me in speech and wiggling. I'm dressing 24/7. Leslie even schedules me for electrolysis, my face first then the rest of my body, including a permanent Brazil cut. I find myself forgetting that I ever was ever a guy. After having my hair cut and nails done at a real salon, Leslie...Read On

20

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

9

An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole...Read On

24

Where do I begin? Chapter 1

Young man lets his inner woman out during an encounter with an older man.

Where do I begin? I’m normally not very open about my private life, seeing as I grew up under the pretense that secrets are meant to be secrets. However it seems I have come to a point where I am comfortable with who I am and where I have been. Comfortable enough to bare to you all my deepest secrets. Deep breath in, slowly let it out. My name is Alicia, well that's my new name, my old...Read On

18

Jamie's Gradual Grooming, Part 3a

Jamie's transformation picks up pace.

I gradually woke up from a deep and warm sleep. My slow awakening became very sudden as I came to two realisations. One, I was wearing underwear from the night before and two, they were wet! I quickly pulled the duvet up and over my head, as if lots of people were watching. I slowly put my hands into my panties and felt a warm liquid all over them, I'd had a wet dream. Straight away I...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

13

Simran - A Crossdresser: Part 1

How it all started

Well I still remember the day back in the summer of 2010. I had just turned sixteen and was introduced to the world of cross dressing in the most fantastic way possible. I guess introductions are in order. I am Simar, an average guy from India, who goes to college, has a great family, great friends. Well something you gotta know first. My family follows sikhism so I have a beard, a...Read On

18

Jamie's Gradual Grooming Part 2

Second part of Jamie's transformation

"What would you do if I put some girlie clothes on?" What a stupid question. The moment seemed to last for an hour but it could only have been a few seconds. Mike looked at me, again with an indifferent look. What would he say back? Would he say anything at all? He glanced down at the chopping board and then back at me. "Could you pass me the onions from the fridge please?" he said. ...Read On

19

Jamie's gradual grooming

Homeless runaway is taken in by a family friend, and is gradually transformed

"Jamie? Is that you?" A voice shouted out from across the road. Jamie lived in a relatively small town or village so it must be someone he knew. "Jamie, it's Mike from three doors down, Phillippa's dad?". With that Jamie stopped, he walked over to the very fast and expensive looking BMW. "Hi Mike, sorry I didn't recognise the voice at first are you okay?" Mike explained, he has seen my...Read On

16

She'll Never Know... (Part 1)

A young man discovers a taste for the finer things in his wife's lingerie drawer.

Once again they had argued before she went to work. The reason was also the usual one – sex. This particular morning Mark had woken unusually early, with his usual erection. Deciding to test Clare's mood, he had rolled over and nudged his naked penis against her, just after the alarm had gone. Letting his hand slide up her thigh, she had moaned gently and pushed back into him, letting his...Read On

8

Missy Returns

It had been a long time from the seven days I spent with my studs, but sadly I went off to school and Missy had to go on an extended vacation. However, school did not work out as planned and I found myself in a new city and my own apartment with a small job. I had to help pay the bills. For a while I lived with a roommate who was a little homophobic and despised the ideas of trannies. He...Read On

31

Meeting Carla

A friend introduces me to Carla

I hadn’t seen Mark for almost a year. His father had found a new job and subsequently his family had moved to another state. I’d known Mark since the beginning of high-school and I was really looking forward to seeing him again. We’d become friends since day one and it had come as quite a shock when he told me he was leaving. Not only had we seen each other in school each day, but we’d hung...Read On

36

Debbie's Place

A crossdresser gets more than he bargained for

My girlfriend, Linda, was kicking me out of the apartment for the night because her sister, Sandra, was coming to stay. Linda didn’t want her parents to know that she and I were living in sin together. I found it all a bit far-fetched that a girl of 23 years old either couldn’t or wouldn’t tell her parents where to stick their beliefs. But, I knew well enough not to argue with Linda over...Read On

23

Aunt and Uncle Sex Slave

It was the summer of '82 and mom and dad were going through an awful divorce. They decided that it would be best that I stay with some good friends of theirs, Charles and Betty, while they got through this difficult time. They were an older couple, both were around sixty at the time. By this time I was a fully fledged cross dresser and no one knew of my secret except a neighbor. I had all of...Read On

9

Crossdresser in Love

A closeted crossdresser finds love with man

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But...Read On

13

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

21

Born to Be a Babe

Sexy girly boy ponders the allurement of lingerie.

I don't know why I started wanting to be a girl. But I do know when it started. I was sixteen when I first started looking at photos of sexy models wearing lingerie in Cosmo . These beautiful, statuesque women wearing the sexiest clothes I'd ever seen turned me on so much. In fact, I was more turned on by looking at these women in lingerie than I was looking at the naked women in...Read On

11

The Sexy Ball Girl

Being a sexy ball girl for her boyfriend's baseball team gets Courtney very horny.

When I was twenty years old and going to college, I had a steady boyfriend who treated me just like a girlfriend at all times. He opened car doors for me and he always paid when we went on dates. He was very sweet to me, making me feel feminine like a girl. He also liked having lots of sex with me in public places like the beach and parks and movie theaters, so we had an exciting, fun...Read On

15

Bookstore Bunny Gang Bang

Dressing as a Playboy bunny at the bookstore lands Courtney four big cocks.

Dressing as a sexy girl is my favorite way to meet men and have fun. There are so many different sexy outfits a girl can wear to attract men and turn them on, they ensure it never gets boring for a man. Every girl wants to be her sexiest when wearing lingerie and I am no different. Recently, I was on a business trip which included spending the night in a motel located across the street from...Read On

31

Hot Fuzz

Caught by a cop

If you have read my profile you would know that I am married with three kids, and no privacy. That being said, I try to indulge in my favorite pastime of cross dressing whenever and wherever I can. I was working as a manager for a convenience store where I would have to get up early in the morning to open the store. It was a 24 hour store, so I just had to get there to send the graveyard...Read On

6

Adventures in a Woman’s Body – Chapter 5: Secretarial Duties

Serving some very important people as the secretary

John waited for me to finish eating my cum burger, and then he told me to get up because we were leaving. I stood back up onto my six inch stilettos and walked with his arm around me, which firmly grabbed my ass. We exited the food court and made our way to his office building. The mall had a vast underground network so we were able to walk to his workplace without going outdoors. Along the...Read On

39

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

10

Jason and Kym ~ Part Two

A story about self-discovery, now turns into a rollercoaster ride!

 Later that same night, I strolled down to my favorite watering hole to tip a few strong drinks in the hopes of either clearing my head or dulling the noises within. After flirting over those drinks with a short blonde haired gal named Kym, we stepped out onto the dance floor to press our bodies against one another to an old Jonny Cash tune. She’d been waiting for some guy to meet her for...Read On

9

A Lifelong Love Of Lingerie

An introduction to a lifelong love affair with women's clothes

At the time I was sixteen, my mother was divorced and living with me, and she still worked and was gone until late in the afternoon on some days, so I would have the house to myself. I did not have access to porn until later, but there was Cosmopolitan magazine and other magazines which had the sorts of ads and stories that intrigued me, underwear ads, tampon ads - they all did the trick. I...Read On

11

Rose Otto

Man is the only creature who refuses to be himself...

"Ah, ah, ah..." cried Brenda ecstatically, hoping that tonight, of all nights, might be different. She was completely naked, her 38c natural tits swaying with the rapid thrusts, her thick hairy legs locked around Doug's firm arse, her hands clasping him as if to keep him in place. Brenda's husband Doug was fucking her passionately, he had fingered her to climax prior to climbing on top of...Read On

11

Learning To Be Submissive - Part 2

My second meeting with Jack

I arrived slightly earlier than I was meant to. After our first meeting I had been given specific instructions. Jack had allowed me to shower and change back into my normal clothes. Once I had returned to the kitchen, I found a note with a key. "Today you excelled yourself, but you have more to learn. Next week on Monday you are to come directly here after you finish for the day. I will...Read On

15

What I Do When I'm Alone

The fun I have when I am alone.

With the wife off to work today, I decide to indulge in my fetish. I wait a little bit till I know she is at work and it's upstairs I go. I take my computer with me to chat with friends and others I happen to meet in chat rooms. I lie down on my bed and start chatting with people and seeing which friends are on. It takes about an hour before I finally find someone to chat with. What follows...Read On

3

Night at the Video Store, part 3

bimbo crossdresser cruises video store in Black part of town

There I was a sissy bimbo dressed like a slut in a short black micro mini skirt, spike heels, lots of junk jewelry, huge platinum blonde wig, shoulder strap white fur purse and, of course, perfect make up. I had never been to this video theatre before and was nervous at first, but I waited for my eyes to adjust to the darkness and then moved into the theatre area. Screen five was recommended...Read On

14

I am Sissy

a fantasy of a taken slave by a pirate captain

The year was 1888. My name was Sebastian but I was now called Sissy since I was taken a slave. My father’s merchant ship was captured and sunk by the pirate crew of the Black Bess. I alone was saved for Captain Booth's pleasure. He was an escaped convict from the prison island of Australia. He was a huge beast of a black man, dark ebony skin stretched tight over enormous muscles that...Read On