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Crossdressing

9

A Chance Encounter

I could not believe what I was about to do.

I have only had three additional encounters since my first time. With that first time it was to satisfy my curiosity. I had thought that now my curiosity was suppressed, and that I would only have to fulfill my need to dress feminine when that urge surfaced. Mistakenly, as I said, I assumed that once I satisfied my curiosity was fulfilled that I would not need contact. I thought that I...Read On

13

Jessie and Sue

Jessie gets invited on a wild date with Sue.

I felt like my life was spiraling out of control. It all started that one fateful weekend when my secret love of cross dressing was discovered by my coworker Dan. He knew he had me, and he had his way with me. Then came the next weekend when Dan invited me to his house only to have himself, Aaron, and Zach take turns with their sissy slave. And now last night, I was humiliated because of...Read On

10

Jessie and the Office Girls

Jessie gets seduced by her office fantasy.

I spent the weekend trying to recover from the pounding that I received from Dan, Aaron, and Zach. I was their slave, and I had enjoyed it immensely. What I didn’t plan on was having all of my moans, groans, and enjoyment being filmed from twelve different angles, along with Dan telling me that he was going to share this video with our office mates. I was worried, yet anticipating what...Read On

17

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

11

Tied and Taken

Fulfilling my dream of being a damsel in distress

I had always had fun and gotten excitement from crossdressing and bondage play. After my first encounter with Chris, I was forced to accept the fact that I had desires and needs that I had suppressed for years. After having been tied up and mouth fucked by Chris, I realized that I didn't just like dressing up like a girl. I just didn't get a kick out of being tied up. I wanted to be a "damsel...Read On

11

My date with Ben part 3

I was invited to Ben’s house for dinner Saturday evening and spent the day getting ready. His wife Susie was looking forward to meeting me again and getting to know me better. I was unsure how the evening was going to go, but I decided that I was going to try and enjoy it as much as possible. I spent the afternoon getting ready, and shaved smooth all over, hoping that Ben and I would get to...Read On

8

An Introduction to Crossdressing Pt 3

After all the preparation I want it too bad to go out.

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any...Read On

8

My date with Ben - part 2

I got a call from Ben Monday morning, and he needed to talk to me urgently. His wife was going to be coming to the proposal meeting that he had talked about and she was looking forward to seeing me there. Ben asked if I would be able to be free for the day on Thursday. My work schedule was light, and the thought of going to a business meeting with them seemed interesting, so I accepted....Read On

10

My First Encounter

This is about my first sexual encounter with a man

I had been cross dressing for years but only in private. I had also had a thing for bondage for a long time. A couple of years ago, I met two other cross dressers who were into bondage. We had been getting together every couple of months and playing bondage games with each other. We would take turns tying each other up and taking photos and videos. But, it was always clear that the other two...Read On

19

My First BJ dressed En-Femme

I needed to confess this. It is not a story, but a reality.

I only cross-dress when the urge to be feminine comes over me. I mostly have dressed privately, but that has changed. The last four years I have ventured out in public. I was curious if I could pass as a female. Little did I know then, when I first went out in public what it would lead too? It is why I am going to tell my story here. I needed to confess and to tell someone even if it is to...Read On

13

Jessie's Payback Continues

Jessie thought the payback was over. She was wrong

It was turning into a wild night, and I was the party favor. After Zach and Aaron had their way with me, I thought I was done for the night. But I couldn’t have been more incorrect with my assumption. As I was getting ready to leave the living room, Dan tugged on the chain that was attached to my neck choker. I went to my hands and knees much to Dan’s pleasure. Zach, and Aaron had been...Read On

20

Jessie's Time for Payback

After Jessie's Reward, it is time for payback!

After Dan left me with his cum dripping out of my ass, I kept replaying his words before he left. “Jessie, you were amazing! I can’t wait to tell all the guys at work about this!” It was Friday night. Dan was the first one to make me feel like a woman, but now I had another dilemma. How am I going to face him and all of my co-workers if he indeed tells everyone about me? I woke up...Read On

15

my first date with Ben

I had been chatting with Ben online for a while and we had talked on the phone several times before I decided to meet with him. I had met him through Craigslist so he knew what I was all about from my ad. We arranged to meet at restaurant for an early dinner so there would be plenty of people around. That Saturday, I spent my time getting ready. I showered and shaved smooth and used a...Read On

8

A Date For The Weekend Chapter 1

A perfect date for the weekend leads to more.

I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if...Read On

27

Jessie's Reward

After a hard week at work, Jessie gets her reward.

It had been an unusually long and hard week at the workplace. The week started on the wrong foot when a major project was likely to be delayed by a month because of a supplier issue. Stress was adding up through the week as my manager kept demanding that I get the project back on course by week’s end. Come Thursday, there wasn't an end in sight. I was thinking my job will be on the line. I...Read On

28

Vicky's Education

Vicky is taken to a gloryhole to enhance her oral skills.

My wife was very pleased with how I had performed as Vicky. My cross-dressing had progressed from a sexual role play with my wife to her setting me up for my first sexual experience with a man. At the same time, she had picked up her own guy and had taken him back to our bedroom. She cuckolded me and had me clean up her pussy after I got home.  From that time on, the only time I was not...Read On

40

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

9

An Introduction to Crossdressing Pt 2

Learning how to be a passable crossdresser

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The...Read On

15

My oddesy 2 - Liam

A friend cheers me up

It had been a few weeks since Glen's puzzling rejection and I was in a slump. I hated my body more than I had in years. Not even sneaking into my sister's old room and playing dress-up could cheer me. And my best friend noticed. Liam was in most of my classes at school and we knew each other since third grade. He had olive skin and a solid German build. Noticing my gloomy disposition he...Read On

11

Gentle Surrender

A Gentle Submission Fantasy Inspired By Another LUSH friend. His Pictures Fire My Imagination

We had talked before. I had asked if you were ready for an experience of trust, risk, and surrender. You were hesitant at first. But after enjoying time and togetherness and long intimate talks you agreed. Your schedule was cleared for a full 6 hours without any interruptions. I had asked you to limit your liquid intake and I had spent the last 24 hours fasting. When I arrived at your place...Read On

14

From Anton to Antonia

Anton discovers a feminine side to his sexuality

The first sex I had with a couple was my boss and some woman we just met in a hotel bar. I liked it, so the boss told me to put out an ad. An advert in Craigslist for my area was all it took. Posted in the casual section under M4WM and a photo of me from the shoulder down, I had a flood of answers. I chose Julian and Rosemary, they were mid- thirties, still twice my age and arranged to...Read On

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

5

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

25

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

17

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

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

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