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Crossdressing

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15

Taking Another Step

More than just words as we take another step toward our ultimate fantasy

It had been nearly a week since the scintillating Saturday when my fiancée and I had the most incredible meeting of the minds about our sexual desires. Unfortunately, as the days crept forward from that fateful afternoon, I began to worry that those moments were an aberration rather than a sign of things to come. In the throes of passion, we had done a bit of internet browsing for the...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

15

Carl, Carla and Hannah - Part 2

Hannah gets the upper hand.

I awoke to the sound of running water. Hannah was in the shower, leaving me alone in bed. A dull ache in my backside reminded me of what had happened last night: Hannah had tied me up, blindfolded me and then fucked me using a strap-on. She had called me a bitch and a slut as she held my legs over her shoulders and pounded me like a whore. And, apart from when she forced me to swallow my own...Read On

10

Confessions of a Sex Crazy Cross Dresser Part 4

Chapters 7 and 8 of Book #1

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all...Read On

10

My First Time - Part 3

The story continues...

As Lydia had promised, on the first day of her vacation I got my first lessons in high heels. It took most of the day before I was able to walk across the room and not fall on my face, and these were only a moderate heel. I took her to dinner to celebrate and, at her request, I wore the satin thong under my jeans. Lydia could not resist reaching out and squeezing the bulge in my jeans,...Read On

10

I Still Love You Tomorrow

How could she be so forgiving? I didn't understand... Caught with the evidence of my secret on my face, my body, and in my hair, I was frozen by her stare as she stood in the bedroom doorway, eyes wide as teacups. “Oh,' she said, too shocked for anything more. I had lied to her! I wouldn't have blamed her if she had left me in that instant, but she stayed. Why? How? We sat together...Read On

10

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

10

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

10

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

10

A Night of Firsts pt 3

Pam has a first

We all took a sip of our drink. Catherine, Anna and myself, presided over by Lauren. I felt like a new gurl at this party. I bit my lower lip, I wriggled in my seat for my dress giving an accidental glimpse of way too much upper pantyhosed thigh. I blushed so deeply. Lauren must have sensed it as she leaned in closer and told me that I was a flirty gurl and those legs of mine might get me...Read On

10

Sharon Goes The Distance

David becomes Sharon at his wife's request

When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or...Read On

10

Made Maryanne - Part 2

John is made aware of his new role

When I woke up the following morning, I immediately became aware of the situation. It was difficult not to notice the pretty white cotton and lace nor the fact that I was wearing it. I quickly recalled the events of the previous night, feeling ashamed at having been caught masturbating. I knew that Beatrice somehow wanted to make a point by telling me to wear her nightdress, but I had no...Read On

10

The Magician's Assistant or How it began - Part 1

Ken had led a pretty normal life until the year his longtime friend needed an assistant for his growing magic act. Magic had always been a hobby with his buddy Carl and he spent many a day watching him perform a new trick in his garage seeing if he could detect the secret. Their being forced to take woodworking classes in high school really paid off when Carl expanded into the realm of...Read On

10

Memories

Reminiscing about time spent before dating

Just for fun, I though it might be nice to share some of the experiences I went through on my way to becoming the sexy slut I am. Before I had the confidence to fully dress and go out, and to go on the few dates I've been on, I was completely closeted. The only way I could express my girly side was through playing on the phone and all alone. I loved dressing up a few times a week. I...Read On

10

Fucked in the Fitting Room Part Two: The Explosive Conclusion

When my lover finds a dress on the sales rack, I get more than I bargain for.

I took Allen's hard cock in my mouth and began to suck it slowly. "Oh, God," said Allen. I rolled my tongue around the tip of his cock and then ran it up and down the sides. "Suck it faster, babe," said Allen. I happily complied, bobbing my head up and down on his cock as fast as I could. I grabbed his balls in my hand and stroked them gently with my fingers. "Oh, baby, that feels...Read On

98

My First Time in a Dress

How I Became a Crossdresser

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday....Read On

63

The Perfect Choice

A girl works to turn her boyfriend into her toy

Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to turn Andrew on, and it was working perfectly.She hadn't slept with him yet and the tension...Read On

47

Total Sub CD Slut

His total sub CD slut

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend. I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends. I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me...Read On

36

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

36

An Uneven Romance

He picks up the girl of his dreams only to find himself being used

I couldn’t believe I’d gotten her home with me. We’d met in a bar when I was drinking with my friends, I spotted her early in the night but didn’t have the courage to talk to her. She looked perfect. She was slim, with long red hair that came down to a tight, round ass. When she turned around, I saw she had a truly beautiful face but there was a sexy, dangerous look in her eyes that scared...Read On

35

Ray and the Halloween Party Part Two

Part two of my wild night at the Halloween party and with Ray...

   When Ray and I arrived at the front door at Sharon ’s house I noticed my lipstick on Ray’s lips from passing the tequila bottle and as I was wiping if off with my fingers the door sprung open. Sharon was dressed as a Playboy bunny and she looked surprised when she saw us. I thought it was because she recognized me but evidently not. “Well, well, Ray, you dirty dog....Read On

31

Wife's Crossdressing Fantasy Part 2

Her anniversary present to me

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. ...Read On

31

A Whole New Me - Part 1

Borrowed panties and a day with my friend reveal a whole new side to me!

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being...Read On

31

Always Up for a Party

Trevor's idea of a party, with me as entertainment

I got home late. What a night! I had gone to the video booth at the bookstore horny as hell but in my wildest dreams I could not have imagined the outcome. Oh sure, I expected sex. I had yet to leave those dark little booths without a mouthful of cum, an ass full of cum or having my balls sucked dry but tonight … tonight! Not only had my ass been filled in the booth but at Trevor’s party...Read On

30

Teenage CD Awakening Part II

A teenage boy widens his crossdressing horizons by starting to wear his mother's clothes

I had crossed the Rubicon. I had tried on my sister's panties for the first time. Now I felt guilty. Incredibly guilty, and dirty. I went to school as normal the next day, but despite the guilt I couldn't get the amazing thrill of trying on that little pair of blue and white striped cotton panties out of my head. As 3.30pm and with it the school bell neared, the overwhelming urge to do...Read On

26

Telling Mom I'm A Crossdresser Part 6: Missy and Mistress Keri

Missy has her first BDSM experience. Plz rate and comment

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least. One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at...Read On

26

Taking That First Step

A story from the seventies

Lance was seated on a bench on the tree-lined sidewalk waiting for the store to open. Despite the warm morning air he began to sweat and his heart pounded in his chest, this was a bold step for him. Now, this particular store was located in an older but still very popular outdoor shopping center despite the malls springing up everywhere. It was commonly referred to as a specialty shop,...Read On

21

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

19

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

19

Telling Mom I'm A Crossdresser Part 14: Back to the spa and a familiar face.

Part 14, yes I feel it is long but please read the whole thing you will not be disappointed.

Part 14: Back to the spa I'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair...Read On