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Crossdressing

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17

Mom's Old Boyfriend: Part One

Courtney seduces her mom's old boyfriend and sleeps with him, all weekend..

It happened quite by chance and we managed to keep it a secret, ever since. I was home alone on a Friday evening wearing my mom's favorite black lace lingerie and her old boyfriend, Ron, came by to see her. He still had a key from when he was seeing my mom and he walked in without knocking on the door, startling me. And he caught me playing with myself through the sexy little black lace...Read On

17

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

17

The Cabin, chapter I

I accidentally stumble a "rich" crossdresser's secret cabin, thrilled by my find.

The latest months had been quite rough on me and I’d been looking forward to this trip for a long time. My girlfriend had left me, muttering something about me not being manly enough for her. In reply, I had buried myself in work and self-pity. When I finally came to my senses, I knew I had to take a break. My backpack was burdened by everything I would need, which wasn’t much. I...Read On

14

Jessie's Payback Continues

Jessie thought the payback was over. She was wrong

It was turning into a wild night, and I was the party favor. After Zach and Aaron had their way with me, I thought I was done for the night. But I couldn’t have been more incorrect with my assumption. As I was getting ready to leave the living room, Dan tugged on the chain that was attached to my neck choker. I went to my hands and knees much to Dan’s pleasure. Zach, and Aaron had been...Read On

14

Office - Caught

Guy gets caught by work colleague wearing tights

My name is Peter. I'm twenty three and I'm a member of the small internal IT team at a large corporation. It's a typical office setup and our small team of three were kept busy with the day to day tasks; failures, PCs and printers and general support. I'm generally pretty quiet and unassuming and, whilst polite and good at small talk, I'm pretty shy, so just keep my head down and do my job....Read On

22

Adventures in a Woman’s Body – Chapter 2: Tease and Please

Things are happening under the table

After I got out of my house, I walked for about 20 minutes to get to this fancy restaurant I made reservations for. It was a long and tiring walk, but I loved cat walking in my sky-high stilettos and hearing the click of my heels with every step. I couldn't pay much attention to what was going on around me as I walked down the streets. I was focused on swaying my hips and crossing my heels...Read On

22

Nice surprise for the delivery man

Me and the delivery man get cosy

I'm a crossdresser in my early 20's and still live at home unfortunately. The day started as it usually does when I'm home alone, dressing up. On this day I had gone for a pink G-string with a matching bra, my breast forms, and some tight leggings which showed off my pert bum very nicely. A black lace top and of course my light brown shoulder-length wig and my make-up. I was in a bit of...Read On

10

Jason and Kym ~ Part Two

A story about self-discovery, now turns into a rollercoaster ride!

 Later that same night, I strolled down to my favorite watering hole to tip a few strong drinks in the hopes of either clearing my head or dulling the noises within. After flirting over those drinks with a short blonde haired gal named Kym, we stepped out onto the dance floor to press our bodies against one another to an old Jonny Cash tune. She’d been waiting for some guy to meet her for...Read On

10

Jenny Learns Her Place

Jenny submits to her lover's desires

His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face. “Oh! Oh! Oh!...Read On

10

From inside to full time

Debra moves from hiding to living full time

With the changes in my persona, there were a few in Tina’s. Again, not massive earth shaking changes but changes none the less. One of them was how we interacted especially in public. We were more like friends than a couple. No one would have been able to notice anything other than two people that knew each other really well. I once asked her about how she was acting.   Tina stated, “Well,...Read On

10

The postman

Lucy gets a delivery from the postman that was a bit more than she expected.

Lucy was in her man mode at home when she heard a knock at the door. She answered it and it was the postman delivering a couple of packages for her. They were full of sexy lingerie and three sexy dresses. The postman came inside her hall to talk. The postman had obviously found out what was inside the bag. “I’m sorry, but one of the bags broke so we had to repack it for you.” ...Read On

10

My First Experience With A Man

My first experience with a man and he made me crossdress

It happen when I was 18 years old. I was working for a clothing company at the time and it was a slow Tuesday morning. As I was folding clothes, a tall (I’m 5’5 he was 6’2) light skinned black man approached me. He introduced himself as Sam. He looked like he was well into his forties but was really fit. He inquire about several clothing articles in our store and slowly the conversation...Read On

37

Sissy at the Bookstore

Or how I humiliated myself in drag

I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decided that I need to take that extra step and I did. I had checked into an adult motel the night before and booked for two days so I had a lot of time on my hands. The night before I had pranced...Read On

31

Confessions of a Sex Crazy Cross Dresser

The first two chapters of my first novel

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeks Chapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used...Read On

31

Jessi's coming out party

Jessi comes out to several friends and has an interesting night.

Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if...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

16

The Frederick's of Hollywood Lingerie Model

Courtney's first job in Hollywood is as a Frederick's lingerie model.

When I first arrived in Los Angeles, I was staying at a motel on Sunset Strip in Hollywood. I had plans on working as a tranny call boy there. In the "L.A. Express" magazine, I saw an ad for a club on Sunset, called the Leather and Lace Lounge, that was popular with trannies and the men who liked them. I decided to go there and learn more about the tranny scene in Hollywood. It was three in...Read On

13

A Nanny Femtastic - 7

A NANNY FEMTASTIC! Chapter 7 After that first dinner Bradley and Felicity retired to their bedroom. And even though they were in a separate wing of the sprawling villa I could hear them making love! I thought of what Felicity felt as a transsexual woman having had a vagina created out of what was her penis. To feel Bradley rigid penis inside her. I wondered how nice it would be to put on...Read On

13

Once Again in Silk - Part 1

It had been many years since my time in Florida and my transformation to Melissa to please my lover, Lydia, and also my own inner desires. She soon grew out of her desire to see me dress up and wanted a normal lifestyle and to date other men. It seemed that our time together had come to an end. I gave up my apartment and I moved back North. As I still had a sizable amount of money left from...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

44

Caught by a neighbour

I've secretly been crossdressing from a young age. In my late teens, around 17, I became more adventurous. maybe because I was enjoying it more. At that age I was very slender, had long dark hair as well has having a naturally smooth and hairless body. My brother and sister were both at uni and my parents would work a lot of the time meaning I was left home alone quite a lot. I would "borrow"...Read On

41

A Visit

Husband dresses up for his wife so that they can have a little fun during the weekend

My wife knew of my enjoyment to wear women’s lingerie when we married and over the months that followed our honeymoon she had often wanted to see more of me dressed up.   I always enjoyed these times although they were not as frequent as I would have liked them to be. One Friday, after a rather long and difficult week at work, I returned home and was greeted by a tender hug and a loving...Read On

30

Our Sissy Slave

Will you be our full-time cross-dressing lesbian boislut?

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what...Read On

27

Two girlfriends stay in for the night

Wife pleases her girlfriend then tells her whats going to happen next

The other day I came home from work and was looking forward to spending the evening with my wife. We had the next day off, and it was going to be great to just get some time with her. After I was home and settled my wife Dawn came and found me and told me she wanted to spend the evening with a girlfriend and have some fun. I was a little disappointed, but a few seconds later, she told me...Read On

27

She Made My Dream Cum True

A girlfriend helps me bring out my inner slut

I had been seeing Ellie for a few months before I told her about my little secret.  We enjoyed straight sex, but something was always missing for me.  After I told her about Vanessa, and my desires to dress up and be treated like a woman, I was really scared she was going to cut and run, but she actually was interested in knowing more.  I confessed some of my innermost desires to her.  I...Read On

21

Smooth Sensation

A t-girl get what she wants......

  God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street London on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipation that tomorrow was Friday and my big night in with my mysterious blind date. I had...Read On

21

My First Boyfriend Part Three

My boyfriend pimps me out to his friends

Steve and I had spent our first night together as a realcouple and in a real bed and it was wonderful. I had intended to wake him up with a blow job but he was already gone when I woke up so I had the whole day to wait for him to return from work. I spent the day just like a housewife would. I wore a house coat and some fuzzy slippers and after cleaning up the place sat down and watched...Read On

21

July 4th Celebration

My wife Ann sets up a mini vacation over the 4th of July.

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am...Read On

19

my discovery

my story of becoming a crossdresser

Here are some stories about my sex life and exploration of who I am. Before I started cross-dressing, I fell in love with high heels, mainly cumming in high heels. When I was younger, my parents used to have a large walk-in wardrobe and when they would go out at night I'd search for my dads porno mags. One night when I was reading some mags and my parents were out, I got a bit too excited...Read On

19

Surprise

Aubrey greets his boyfriend home from work in a new way. Slight BDSM ahead.

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip...Read On