Crossdressing

howaboutme51

My first time

First time with a CD. First gay experience.

My first story. And it is the true story of my first encounter with a CD. With a click of the mouse, I had committed… I was going to meet a cross dresser just a few miles from home. Could I go through with it? Is it really what I wanted? Who was I kidding? Of course I wanted it. Now it was time to just suck it up, princess. I took a quick shower and the dressed in my tiniest,...Read On

Added: 09 May 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: cd  oral  anal   | 6 Comments

PlayfulAshley

TV Repair Man

DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing from the first person perspective simply because it is a fantasy and it’s just more fun that way;) About a month ago my TV broke and it is kinda big and expensive, so I decided to have it fixed rather than buy a new one....Read On

Added: 04 May 2011 | Category: Crossdressing | Avg Score: 4.93 | Tags: crossdressing  bisexual  oral  first time   | 10 Comments

PlayfulAshley

Ashley’s First Time With a Guy

Ashley’s First Time With a Guy DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing simply because it is a fantasy and it’s just more fun that way;) So it all started on Valentine’s Day of that year. My wife and I had gone to dinner and got a hotel room for a romantic...Read On

Added: 03 May 2011 | Category: Crossdressing | Avg Score: 4.89 | Tags: crossdressing  first time  anal  oral   | 21 Comments

cassandrababy

Extended Vacation Chapter 3

Cassie continues her new life

Cassie has her first full day as a woman as she continues her seven weeks living as a woman 24/7. EXTENDED VACATION Chapter 3 I arrived at my new apartment around 5 PM, and it took me over three hours to unpack and get organized. It was very enjoyable to move in and have a fresh start. I loved looking at my closet and all of my drawers as everything was for Cassie. My bathroom...Read On

Added: 29 Apr 2011 | Category: Crossdressing | Avg Score: 5 | Tags: cross dressing  toys  anal   | 4 Comments

cindytranee

Bo Peep and the neighbor

crossdresser role play

It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none. I was nearly at my wits end so when I was asked to house sit for my uncle...Read On

Added: 27 Apr 2011 | Category: Crossdressing | Avg Score: 4.71 | Tags: oral  anal  spanking  role play   | 5 Comments

libertina

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that would be perfect. I really wanted...Read On

Added: 15 Apr 2011 | Category: Crossdressing | Avg Score: 4.88 | Tags: strapon  crossdressing  role-reversal  anal   | 12 Comments

cassandrababy

Extended Vacation Part 2

Cassie continues her new life

Chapter Two in my novel of Cassie living 24/7 as a woman...please read Chapter 1 and let me know if you want more. EXTENDED VACATION Chapter 2 After experiencing a great sexual adventure less than two hours after becoming Cassie full time, I was now in a even better mood as I got back on the freeway and headed north. Due to the low air pressure in my tire, I drove around 50 MPH for...Read On

Added: 13 Apr 2011 | Category: Crossdressing | Avg Score: 4.78 | Tags: crossdressing  oral  quickie   | 4 Comments

GirlyWorld

Jack's Little Bitch

Learning to be a girlfriend

Steph had been gone for about one week out of her two week visit to her Mom. She'd asked me to pick up the mail and water the plants while she was away, because her boyfriend, Jack, was also going to be away for the month on a business trip abroad. “Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.” Steph was right...Read On

Added: 10 Apr 2011 | Category: Crossdressing | Avg Score: 4.56 | Tags: crossdress  oral  bisexual  masturbation   | 4 Comments

cassandrababy

Extended Vacation

The first chapter of my second novel

Hi Everyone...this is the first chapter of my second book. I will publish more chapters if you like this one. Extended Vacation Chapter 1 Hello my name is Cassandra. You can call me Cassie (or Sandy, but recently, I like Cassie). I have been cross dressing for many years. However, the last year, since I turned 40, I have been dressing more than I ever have in my entire life. I made a...Read On

Added: 07 Apr 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: cross dressing  oral  quickie   | 6 Comments

cindytranee

Cindytranee meets the maintenance crew

Cindytranee gets caught crossdressing and gets fucked by three men

This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private and I really enjoyed being there. This was the first time in years that I had lived alone and I loved it. It gave me the freedom to enjoy my favorite thing, cross dressing and having sex with as...Read On

Added: 04 Apr 2011 | Category: Crossdressing | Avg Score: 4.82 | Tags: oral  anal  orgy  crossdresser  inerracial   | 9 Comments

thony777

I become my wife's girlfriend. Part II.

This day at work was unusually tedious and seemed like it was never going to end. At the beginning I occasionally dropped my boss's cup and the coffee poured on floor, but luckily the cup survived. After this some guy stepped on my toe and caused me much pain, I bent to touch it and suddenly had a feeling like my butthole was cut by the string of thong. Later my boss was very angry all the day,...Read On

Added: 25 Mar 2011 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing  wife  girlfriend   | 6 Comments

Teigan_andi

First time

I was 17 when I had my first experience with another man. My sister was in her sophomore year at college and I in my senior year at high school. She was going to spring break in Florida and since me and her had always had a great relationship she invited me along with her and her friends. My sister was cute, blond hair and blue eyes. Very tan and athletic. She had that all American preppy...Read On

Added: 22 Mar 2011 | Category: Crossdressing | Avg Score: 4.62 | Tags: first time  crossdressing  thong  cum  anal   | 17 Comments

thony777

I become my wife's girlfriend. The beginning.

My name is Tony and I'm a regular straight guy. This is the story about my life as the part of lesbian couple, and yes, I'm aware of weirdness of this statement. During the first period of our relationship our sex life was fantastic, a man's dream. At this time I wasn't aware of my dark fantasies, our sex was very good and I thought of us as a very nice couple. And then, something like...Read On

Added: 20 Mar 2011 | Category: Crossdressing | Avg Score: 4.63 | Tags: crossdressing  sissy  bisexual   | 8 Comments

Xdresser54

Yolande's Adventure (part 2)

The continuing story of How Yolande Became a Cockslut

After I re-applied my makeup, straightened my wig and checked my appearance in the mirror, and had a quick shot of tequila, I felt suitably slutty and game enough to venture out into the big wide world for the first time. The room service boy had made me feel special as he received my first ever blowjob, and even gave me a tip for it, making me feel such a slut. I enjoyed taking his cum down...Read On

Added: 12 Mar 2011 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  slut  cocksucking   | 8 Comments

salidin

A weekend with Nancy part 3

Get used to it, you're going to be my bitch alot from now on.

Upon arriving back at the car Nancy said that we had to hurry to our next destination because it would be closing soon and then she instructed me to drive while Alice and herself got in the backseat. "Honey, do you know that porn shop up the road a couple of miles?" said Nancy. I nodded that yes I did and I was instructed to drive there quickly. At the porn shop, Nancy suggested that I...Read On

Added: 31 Jan 2011 | Category: Crossdressing | Avg Score: 4.94 | Tags: strapon  anal  crossdressing   | 4 Comments