Crossdressing

sluttracy99

My Sexual Odyssey Part V: A Real Whore

A continuation of the journey described in part 4

The next morning as I awoke, I realized that in just a few hours I was to re-experience the previous day’s activities. This seemed too much too soon, but I had agreed. Of course I could always cancel, but then if I did so I would wonder how much I’d miss it and whether I would have acclimated to the frequency and intensity. I decided to just forge ahead and so I got dressed and left for...Read On

Added: 03 Jan 2015 | Category: Crossdressing | Avg Score: 5 | Words: 2,587 | Tags: autobiography  prostitution   | 5 Comments

sluttracy99

My Sexual Odyssey Part IV: From Slut to Whore

A continuation of the journey described in part 3

The next day as I went to work, I wondered what adventures lay before me. In a sense, it was up to me, in that I just had to put myself out there, not to mention put out. Still, the outcomes are unpredictable: I had no way of knowing ahead of time that a coffee date would turn into such a wild experience. When I arrived home I called Tom, and told him everything that happened the previous...Read On

Added: 02 Jan 2015 | Category: Crossdressing | Avg Score: 5 | Words: 3,366 | Tags: autobiography  acceptance  prostitution   | 3 Comments

thatfemininUrge

More Than I Bargained For

I had no choice but to accept the situation that I put myself in.

After my first two encounters pleasing a man while dressed en-femme, everything had changed. I had accepted without regret that I could make a man not only become aroused, but that I could bring him to orgasm. I would no longer fight the urge to become feminine. When that urge would strike me, I no longer fought it, but welcomed it. I rationalized that it was who I was and that I...Read On

Added: 31 Dec 2014 | Category: Crossdressing | Avg Score: 4.7 | Words: 6,887 | Tags: blow jobs  oral  en-femme   | 5 Comments

thatfemininUrge

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

Added: 20 Dec 2014 | Category: Crossdressing | Avg Score: 4.71 | Words: 5,699 | Tags: bj  oral  dressed en-femme  crossdressing   | 7 Comments

pleatedskirt

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

Added: 13 Dec 2014 | Category: Crossdressing | Avg Score: 4.89 | Words: 3,297 | Tags: crossdressing  bondage   | 12 Comments

larkin3445

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

Added: 13 Dec 2014 | Category: Crossdressing | Avg Score: 4.55 | Words: 2,630 | Tags: crossdressing bondage anal   | 8 Comments

ericamalamute7

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

Added: 08 Dec 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 3,016 | Tags: crossdressing  oral  anal   | 6 Comments

ericamalamute7

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

Added: 06 Dec 2014 | Category: Crossdressing | Avg Score: 5 | Words: 3,356 | Tags: crossdressing  oral  anal   | 3 Comments

larkin3445

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

Added: 27 Nov 2014 | Category: Crossdressing | Avg Score: 5 | Words: 1,885 | Tags: bondage  crossdress  oral   | 6 Comments

thatfemininUrge

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

Added: 27 Nov 2014 | Category: Crossdressing | Avg Score: 5 | Words: 5,635 | Tags:  blow job  crossdressing  sexual   | 16 Comments

ericamalamute7

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

Added: 07 Nov 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 2,842 | Tags: crossdressing  oral  anal   | 5 Comments

jill_on_her_knees

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

Added: 06 Nov 2014 | Category: Crossdressing | Avg Score: 4.63 | Words: 803 | Tags: first date  crossdressing  slut  beach  submissive   | 4 Comments

hotvicky

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

Added: 27 Oct 2014 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,012 | Tags: crossdressing  oral sex  gloryhole   | 16 Comments

bigbubblygurlnc

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

Added: 15 Oct 2014 | Category: Crossdressing | Avg Score: 4.89 | Words: 2,224 | Tags: crossdressing  straight sex  lingerie  bbw   | 22 Comments

transgurl

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

Added: 11 Oct 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,665 | Tags: anal  first-time  crossdressing   | 13 Comments

Simes6699

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

Added: 03 Oct 2014 | Category: Crossdressing | Avg Score: 4.92 | Words: 3,410 | Tags: mmf  anal  cross dressing   | 8 Comments

Jess_cd

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

Added: 03 Oct 2014 | Category: Crossdressing | Avg Score: 5 | Words: 2,588 | Tags: domination   | 2 Comments

ssuzie

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

Added: 28 Sep 2014 | Category: Crossdressing | Avg Score: 5 | Words: 1,613 | Tags: transformation  sucking  anal   | 4 Comments

ssuzie

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

Added: 24 Sep 2014 | Category: Crossdressing | Avg Score: 4.17 | Words: 871 | Tags: cheating  reluctance    fantasy  trans   | 10 Comments

gentleman_wolf

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

Added: 17 Sep 2014 | Category: Crossdressing | Avg Score: 4.77 | Words: 2,775 | Tags: crossdressing  first time  young  old  trap   | 13 Comments

londonbrum

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

Added: 16 Sep 2014 | Category: Crossdressing | Avg Score: 4.71 | Words: 1,955 | Tags: older  younger  dressing  underwear  seduction  submission   | 14 Comments

pleatedskirt

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

Added: 12 Sep 2014 | Category: Crossdressing | Avg Score: 4.95 | Words: 2,984 | Tags: crossdressing  bondage  pvc   | 19 Comments