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Crossdressing

7

Master's Reminder

I had been seeing Master John for about a year now and thing’s were going well or so I thought!

I had been seeing Master John for about a year now and thing’s were going well, or so I thought. I arrived at his home like any other weekend in the outfit he wanted me to wear for my punishment. He would always choose the week before and I knew that there was no argument whatever he wanted he got. I hoped that I had got everything just right for him. Anything slightly out of place or...Read On

36

The Awakening of Susi

Susi discovers the joys of anonymous cock sucking at a glory hole (true story)

Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I had many female friends who loved to dress me up in their sexy clothes and strut me around in front of their boyfriends. They thought it was cute to see me in full makeup and a wig wearing a...Read On

8

Big Green

Loosely based on true events and it is my first story so please be easy. Being a Marine for most meant traveling, working out and above all alpha males only. For me all of this was of interest but I didn't work out and I was definitely not an "Alpha Male". Slim in stature I stood all of five foot, six inches weighing in at a whopping 145 pounds. I wasn't much to look at in a uniform but out...Read On

17

becoming LoriAnn - Part 6

Last minute preparations for our night with her husband Max!

Nikki and I got together one more time before we set her plan in motion. We had to make sure we were on the same page, that Max would have the ultimate night of his life and we had to spice up Nikki's wardrobe. Nikki was a beautiful woman, slim and sensuous, but a bit conservative in her dressing. So we made a date to go shopping. We started at Victoria's secret. We bought contrasting...Read On

10

Becoming LoriAnn - Part 5

Lori goes out for her first assignment and tries something new

I was now a full time working girl for Walter and I had been given my first assignment. Walter explained that I would be spending time with a couple. It seemed that this couple had decided to add some spice to their sex life by having a few threesomes. It began with the husband, wife and another woman. The second and the third time were the same except with a different woman. And while...Read On

12

Becoming LoriAnn - Part 4

LoriAnn has found hereself as a cock sucking, cum slurping, anal whore

I started seeing Walter, my friends uncle, about every other day and every other day was a sexual adventure. I was a cock loving, cum slurping whore in training. Soon I moved in with him and he had his way with me every day. All I was allowed to wear was a bra, a thong and stiletto heels. I was to have my hair done and full make up everyday. When expected I was to fall on my knees, suck...Read On

10

Becoming LoriAnn - Part 3

LoriAnn takes another step towards becoming the slutty gurl she wants to be

I was enjoying my new found sexual freedom. My first steps were slow and easy but nothing felt more exciting than discovering the feel and taste of a new hot, hard cock. The boys at school never really bothered me about regular sex and long as they got to shoot their big hot creamy loads down my throat or all over my tits, and I was happy each time I was able to swallow one of those...Read On

6

Belle brings back a girl

Belle goes on a drunken night out and brings a girl home to share with Lucy

Lucy was lazing around in the living room when she heard Belle drunkenly try to scrape the key in the front door's lock. She heard giggling - a second voice. A woman's. Lucy put her tattered copy of Asimov's Second Foundation down on the coffee table and owled the door with interest, her nylon legs sprawled across the arm of the sofa. Lucy and Belle were both avid readers. Between them...Read On

7

Mistress Lucy takes control

Power reversal; the usually sissy crossdresser Lucy has fun with her girlfriend, Belle.

Belle had finished disrobing and stood in her bra and thong, both pink, following Lucy's command. The latter stood in front of her girlfriend and, with a light touch of the shoulder, pushed Belle down on to the bed. Belle looked up at Lucy expectantly, eyes wide. Neither girl wore any makeup; they'd been awake for a couple of hours and, having spent the morning in the kitchen loafing around...Read On

15

Becoming Lori Ann - Part 2

Lori Ann learns some new tricks

The more I thought about the warm milky cum dripping down my hand the more I knew I wanted more. My sisters continued to take me to parties as their cousin and they enjoyed seeing me having fun with the boys - mostly jerking them off - but I wanted more. I wanted to meet boys on my own and more than anything I wanted to taste a rock hard cock. I convinced my mom that it was time for Lori...Read On

4

My Night at the XXX Video Theatre - Part One

My adventure in a bad part of town at an XXX Video Theatre

It was almost 2 AM when I pulled into the Big Town XXX video theatre in the southeast part of where I live. It was a Saturday and the parking lot was full. I had never been to this particular theatre but it was in the adult theatre chain that I had been visiting for the past two years. Each theatre is different depending usually on the part of town where it is located. Southest part of my...Read On

22

Becoming LoriAnn part 1

a boy becomes the girl he always wanted to be

I had two old sisters and spent many hours borrowing and dressing up in their beautiful clothes. I loved the soft texture of their panties and bras, the silkiness of their nighties and the tightness of their pantyhose. I especially loved feeling sexy in their miniskirts and tops that revealed just a little bit of my chest. I would dress up and wish I was a cute girl. One day it happened,...Read On

33

Family Friend Outing

A family friend fucks me after outing myself to him

A few years ago I went back home to Greece for Easter to see my folks and enjoy a bit of the sun. My folks live in a small town where it’s impossible to get any cock if you are not out. As any typical small town where everyone knows everyone, coming out to a few people becomes coming out to the entire town after a few days. So naturally I spent most of my time gagging for cock in silence. ...Read On

21

Afternoon Delight

Hot afternoon session with two gorgeous ladies

I was stuck in the office on a pleasant sunny day in late summer, daydreaming about the afternoon of delight that lay ahead of me; I was meeting up with my lover, Kate, later that day. Kate is a girl I have been friends with now for a number of years, we met through some mutual friends and hit it off straight away. We are both in relationships of one kind or another but we are good together...Read On

28

Motel Fun for College Crossdresser

A young college student enjoys a girly getaway at a nearby motel.

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a...Read On

10

Telling Mom I'm A Cross Dresser part 18: Missy's Halloween Party

Part 18 is about halloween. Hope you all enjoy despite i was a little rushed for this one.

I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It...Read On

22

Two Girls Are Better Than One

My girlfriend sets me up with other men we share.

My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life. She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and...Read On

29

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

9

Yes Captain

The crew gets a little closer than normal

It had been a while since Sarah had a lover. She was aching to slip into something sexy and get a man going. She had been to a few clubs but found nobody that could fix her needs. That was until she arrived at work on Monday. Sarah was a copilot for a major airline. She entered the cockpit and met the Captain John. He was a good looking man. Tall, blonde hair, and a smile that would melt...Read On

46

Wife's Crossdressing Fantasy

My journey from boy to man to woman

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making...Read On

119

Halloween Trick or Treat Surprise

Dan and Susie go to a Halloween costume party Susie has him dress as a women and changes him forever

Chapter 1 –Susan Charity Event To my surprise Susie my wife of 15 years comes home from one of her many business trips. She is all excited about a Halloween costume party fund raiser, for non profit that supports women studies. The invitation states, the best couple for this evening will receive a free weekend in Bermuda. She wants’ us to go as couple switching genders.  Let me...Read On

19

My Lesbian Lover

My first adventure out as a woman ended in the arms of a woman!

My wife was trying to come to grips with the realization that I cross dressed, with marginal success. Part of her plan was for me to meet in the Twin Cities with other CDs so I could have a ‘safe’ place to dress up, away from our small town. To be safe, I was to drive up, change clothes there, meet with my friends and then change again for the drive home. A good plan … a safe plan … but not...Read On

27

The Pool Man

Sunbathing near the swimming pool, I turn on the handsome new pool man.

It was June and time for sunbathing by the pool in my backyard. To my pleasant surprise, I saw that the pool man the company sent this year was young and handsome with a muscular body and porn star mustache. I was instantly attracted to him the first time he came and we hit it off quickly. I was wearing a pair of cut-off shorts with a sexy black thong panty underneath. And I felt very sexy...Read On

6

Girlyboy Gone Wild - Part Seven

Fifi, the sexy French maid, gets to do 69 with her handsome boss.

After getting Rich big and hard with my sexy outfit, I was now ready to put on a show for him Whenever men see me in my panties, they want me like a girl. It follows that whoever wears sexy little panties also likes big hard cocks to suck on and play with. My sexy French maid outfit was especially good at making me feel like a slut for a man. Since so many men had fantasized about being with...Read On

7

Beach Day

Wearing my sexy panties to the beach gets the men turned on for me.

Wearing my sexy panties to the gay beach always gets the men turned on for me. Being the only girlyboy there, I get hit on by lots of big studs. The attention they give me is flattering and leads to lots of sexual pleasure. Being topless, I get to show off my nice titties and the sexy panties I'm wearing let the men know I want some dick like a woman gets. It was a beautiful day for the...Read On

5

Derek and Amy: Derek's Turn

Derek takes control

As I walked into the hotel room hours in advance, my cock was rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society. It was both Matt and I's first times with...Read On

4

Derek and Amy: Matt makes three

Amy's husband Matt joins the fun

My lover and my husband are in separate rooms changing into the clothing I've laid out for them. When they're finished they'll come into the library where I'm sitting waiting for them. This will be the first time they've touched each other and I'm not going to miss a minute of it. I'm sitting in a big padded chair diagonal to the door. My husband, Matt, comes in first. He looks...Read On

6

Derek and Amy

Derek and Amy enjoy some time alone.

We're holed up in a nice little hotel room in the middle of nowhere. No one around here knows us and no one will bother us. Tonight's all about us. Once we get settled in I send him off to take a shower. Now that I'm sure he's busy it's time to get to work. Digging out my bag I lay out the outfit I've had prepared for a long time. The panties are black silk, as soft as butter. There's a...Read On

4

Karren Gets Sucked and Fucked Part 2

It gets hotter for Karren, Nancy and Kevin

Karren followed Kevin to his home in her own car so if she had to leave she could do so at her leisure. Karren wondered what Kevin's wife looked like, would she like the idea of a man dressed like a woman making love to her? Would she like sharing Kevin's cock with another man dressed as a woman? She hoped everything would turn out for the best.  Her thoughts were arousing her cock; she...Read On

4

Karren Gets Fucked and Sucked

Sex is abundent in this story

Adventure in Nylon 3 Part 1 Karren gets Fucked and Sucked He was all dressed up in his finest outfit. Starting with the prettiest white lace panties he owned. A white lace teddy with attached garters, a built in under wire bra that was filled with breast shaped silicone pads to look and feel like the real thing. He covered these with a silky smooth full white nylon slip. His shaved legs...Read On