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Crossdressing

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7

Married Crossdressing Fun Ch. 2

The relationship moves forward

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was...Read On

20

The Compromise - Part 2

The fantasy compromise comes with an unexpected twist.

Andre and his three girls, me being one of them, piled into his car. Andre assumed his role as the driver, Mikayla grabbed shotgun, and my wife, Ally, and I got into the back seat. My heart pounded in my chest with nervousness, as this was my first time going out en femme. Ally no doubt saw the fear in me and scooched closer, taking my hand in hers. "Baby, don't be scared. We're just a...Read On

8

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

3

GAG-A-RIFIC BARRY part 2

Barry's revenge continues as girl power reigns supreme!!

After leaving Barry out in front of my apartment complex for 5 minutes, Jenna and I went to check on him.  Actually, we went to laugh at him.  What we saw was Barry trying to hop (handcuffed and anklecuffed) towards some bushes for cover.  If you remember, Barry was wearing only a pink thong panty.  We watched through the glass in the apartment stairwell and laughed until we cried.  Barry...Read On

15

Falling for Zak

A young man let's himself go to another man's desires

I hadn’t noticed the time, and I’d missed the last train home. The student party was fun, but I was in a bit of a panic not knowing what to do. People were leaving, and the crowd was thinning out. If it had gone on for several more hours, I would have stayed there and taken the first train in the morning, but that didn’t look likely. The hostess was already clearing up. I figured she’d...Read On

22

My First Taste of Cock

Tammy blows and swallows her first cock.

After fantasizing for so long about what it would feel like to dress as a slut and suck a cock, I decided it was time I tried the real thing. I posted an ad on Craigslist with a couple of pictures of me dressed, asking for someone to let me dress for them and swallow their load. I got a lot of responses and most of them just sounded creepy except for Matt. Matt was 36 (I was 25) and a hot...Read On

6

My Mother's Boyfriend, My Slut! (part 2)

Now that he was my slut, I couldn't seem to get enough of him.

The day had been wonderful, seeing my slut skewered on my strap on. His nipples peeking through his netted shirt as he begged to come with me buried deep inside of him. After he came all over his chest and face, I had exited the room, needing my own release. I headed for the shower, happy to leave him to clean up his mess. With the taste of him still on my lips, I turned on the water....Read On

16

Stephen and Stephanie

A young man's journey through cross-dressing, femininity and sexuality

As neighbors, Carol, Karen and I regularly met up on weekends during school term and more often during the holidays. We played many games together, and I happily joined in, despite their girly nature; I even played with dolls. Of course, the kids at school found out about this, and I was bullied mercilessly for being a sissy. I tried to explain that no boys were living nearby to play with,...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

14

Ready to Perform, Part Two – All Crossed Up

I get more than I bargained on!

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would...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

13

A Night of Firsts pt 1

So many firsts for a shy gurl while traveling

'Oh my God, this was the night,' I thought to myself. 'I'm finally going to go out dressed.' I work for a small company and get to travel a bit, but I've really only dressed in hotels when I could drive as flying with all my things makes me really nervous. The idea of me and a travel bag being examined and having a stranger discover my femme things just didn't do it for me. However, this...Read On

19

From Sam to Sarah: A genre-bending story of sexual and personal discovery. Chapter 2

Sam's request is honored in a most unusual way.

The anticipation was eating me alive. My girlfriend, Aubrey, a strikingly sexy, gorgeous, blonde, polyamorous, bombshell grad-student and I had been living together for about three months. She had taken my virginity and was the dominant one in the relationship. She had been fucking another guy, Scott, every other weekend for about two months, and I had finally asked if I could be there in...Read On

5

We All Have Our Stories

Several vignettes on the theme of Crossdressing.

I want to present a few short vignettes concerning crossdressing. A most interesting and individual form of sexual gratification and fulfillment. The first story concerns a strong man, happily married and happy with the sex he is getting from his wife, but something seems missing in his life. He often walks the streets and window shops, but seems to be drawn to the windows displaying...Read On

16

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

The Night Of A Thousand Dreams

I hope you enjoy

There was a few odd looking drugs laying on the side from a party. Being bored I decided to see what they were all about, I had dabbled before but had no idea what they all were. I had seen someone use a bottle with an inhaler on it, one good slug later I felt good. I looked through my wardrobe and decided that all guys seem to go for the more cute look in a girl. As I was feeling daring...Read On

11

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

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

14

Felix becomes Felicity - Chapter 7

FELIX  becomes FELICITY Chapter 7 …We both fell asleep almost immediately. I got up whilst he was still asleep in the morning and put on his shirt loosely over my naked body. I woke him up with breakfast , we kissed and he left late morning.  I had been lucky to escape him not discovering my penis! I had to think hard about what to do about this. I would just have to have to tell him...Read On

16

First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On

4

Settling In

Escaping oppression closed one door. Now Dawn has to find the next one.

I didn’t know why James had asked to meet me at Penny’s. He’d said that it was important for me to show up on time because they needed to talk to me. When I arrived, Penny greeted me at the door, and told me to go get Dawn out of the bathroom. I emerged a few minutes later completely changed into Dawn Summer, and into a mini-surprise party. “Happy Birthday Dawn!” Penny and James sang together....Read On

11

I did not know I had a disorder

Bi man dressed for the first time to please a man

I did not know I had a disorder CindyUSA I am not sure if I should be embarrassed, ashamed, depressed about my condition. I do not look unwell; does it show? I look normal to my wife, family and co-workers. I wonder if they know about my disorder. If they had, why did they not tell me? Like most illness, they start slow and build up and suddenly, bang; right between the eyes it hits...Read On

23

I met the man of my dreams

I noticed him at the gym when his cock was peeking out from under his shorts

I work from home and only have to go into the office at the beginning of the week and at the end.  So with travel and time in the office and a few extra chores, I dress in guy mode about 10-12 hours a week.  The rest of the time I am Melanie!  In the morning I dress as if I am going into the office.  I often wear a skirt and pretty top or a dress.  I always wear hose, my wig, full makeup...Read On

6

Girlyboy Gone Wild - Part Two

The panty party weekend brings new boyfriends into Courtney's life.

It was very flattering when Bill told me I have a hotter body than his ex-wife. Since it was his first time with a girlyboy, I knew he was being honest. A more experienced gentleman might have said it just to be nice. But Bill really meant it. In fact, he said his cock was already hard for me just from seeing my nice ass poking out of my turquoise thong. Bill was my 7:30 date, then I had Dan...Read On

23

My Oddesy 1 - Glen (here and gone)

A (mostly) true story of my first time dressing for another

"But mum. I'm too sick to go to school." I give my best fake cough. It was late senior year and I had been busting my balls for months. I just want a day at home alone. She finally replies after a minute of withering glares. "Fine. I'll call the school. But you're seeing a doctor Monday if this persists. I'll be back around five." "Sure. Whatever." I lay perfectly still until the sound of...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

9

All The Way (Part 3)

Brenda goes the distance

When I awoke it was later than usual but considering the fact that I'd been through back to back fuck marathons in as many nights, I thought it wasn't bad. Slipping out of bed I stepped into a robe and went to the potty, before looking at myself in the mirror. I was a mess so I took the time to freshen up my makeup, washing some off before putting any more back on. Satisfied with how I looked,...Read On

15

Made Maryanne

John is unaware of the female power to crush his manhood

It was 3 am. I was busy whacking myself off in the bathroom when Beatrice caught me. She and I had only been together for a few weeks when I started taking a special interest in her underwear. I loved the smell of her wet pussy, combined with the cozy softness of the cotton panty gusset pressed against my nose. Wearing one pair, feeling the delicate material clinging tightly to my ass, I held...Read On

11

The New "Gurl"

Transforming mind and body one nylon at a time.

Every since I was four or five years old, I can remember being extremely interested in girls’ and women's’ clothes.  This interest continued on and off throughout my childhood, and became quite an obsession during my teenage years.  At sixteen, a most exciting experience occurred that I shall now recount in detail with help from my diary.   During my teenage years, I was raised by my...Read On

9

A Master For Julie Jizzbucket

A story i have written in regards to my master and myself

I had spent the last couple months indulging in some mild cross dressing. After a few nights wearing clothes that made me feel so sexy and womanly. Until recently I had only worn panties, bras and a few sets of stockings and teddys that I had bought for an old girlfriend before she broke up with me to date a guy that had more money. I have also been going online to a site called Lush...Read On