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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


First Time, First Fuck, New Porn Star

A story I wrote while on a short break from my Missy series. Don't worry, I just need inspiration.

I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started...Read On


My night as my wife's sissy boy

My wife surprised me, and how! It Was a night I will never forget.

The last few weeks had been extremely busy and my wife and I had very little time to spend with one another.  We needed some alone time so we made arrangements for the kids to spend the night at their grandparents house.  My wife asked if I would mind dropping them off by myself as she had a few things she like to get ready while I was gone. As I pulled into the driveway I...Read On


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


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


Andrew to Andrea (Part One)

Andrew is about to really see the other side

Hi, I'm Andrew; at least I was Andrew full time until about a month ago. I have always been fascinated by lingerie: its feel, its appearance, how it just makes a body look that much more sexy. Like most curious types I started young (at sixteen, so not all that young), swiping what I could from my sisters or cousins when I could and squirreling my prizes away until I could find time for them....Read On


Pumped While Wearing His Pumps

Hitching A Ride with the Lothario of Lingerie

What a place to be stuck! Under a sign that says Coors Road and practically dying of thirst. I was now two-thirds of the way across the United States but perhaps the most difficult portion of my cross-country hitchhiking adventure lay ahead. It is all deserts from there on the outskirts of Albuquerque to the Pacific coast, my ultimate destination. I had left from Maine four days earlier...Read On


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


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


Hitch-hiking Baby Doll: Part Two

Being a sexy girlyboy for a trucker stud leads to lots of sexy pleasures.

I woke my trucker stud up in the middle of the night by sucking on his cock and making it hard for him. When I had him good and hard, I climbed back up between his legs and let him put it in me again. His cock was nice and big and my ass was good and tight. It felt good to feel like a girl receiving anal from her big Daddy. While we lay on our sides in his bunk and fucked, my trucker...Read On


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


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


Mischa's First Time With a Man

First anal experience dressed up with a man.

I have been cross dressing for a very long time, but it wasn't until recently that I decided to go full time girl. I have very feminine features and learned to embrace them over time. I always wanted to be the live-in 'girlfriend' of an older daddy-type of man, who would let me please him all the time. The thought of being a man's personal companion and sex toy is extremely gratifying. There's...Read On


Late Night Bus

Ben makes and receives a deposit at the depot...

It's a beautiful, foggy English night. Panting, my lungs aching from the cold, I reach the bus stop at a dead run skidding to a halt on the loose crumbling tarmac. The salty taste of Steve's cum still fresh on my tongue and my anger unabashed. Catching a breath, I realise just how much I love nights like these. The ubiquitous street lights struggle to penetrate the gloom of their...Read On


Explorations beyond my expectations

My introduction to pegging, cross dressing and so much more

I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn't return until Sunday evening, giving us plenty of time to explore and play. She knew I liked ass play from conversations about things...Read On


A friend with something extra.Part 2

Ian and Grant test the waters.

Ian headed to the bathroom to clean up. As he did he allowed his mind to recall the most recent events of the evening. He arrived at his best friends house for one of their pizza and movie nights and discovers a sexy girl in his buddy's bedroom. He soon discovered that the sexy girl was, in reality, his friend Grant. He didn't look or talk like the Grant he knew, he talked and looked like...Read On


Ray and the Halloween Party

My friend Ray meets Lisa for the first time as we go to a Halloween party....

   I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school.    At that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa. Even most of my best friends had no clue. (At...Read On


Bookstore Crossdressing

Giving Up My Butt-Cherry

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. ...Read On


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


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


More Than I Bargained For

I had no choice but to accept the situation that I put myself in.

After my first two encounters pleasing a man while dressed en-femme, everything had changed. I had accepted without regret that I could make a man not only become aroused, but that I could bring him to orgasm. I would no longer fight the urge to become feminine. When that urge would strike me, I no longer fought it, but welcomed it. I rationalized that it was who I was and that I...Read On


Crossdressing Domina gets a new slave

A new slave drives a crossdressing Mistress wild.

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels....Read On


Chelsea's New Slut

Chelsea makes me her new slut and begins to train me.

            I was wondering why Chelsea wanted to go swimming with me that day.   She had never shown interest in hanging out with me before, but I figured why not go for a swim with friends.   I thought she was way out of my league; she was 5’ 9’’ with beautiful straight black hair and huge double d breasts.   I was just 5’3’’ and a science nerd.   I mean she said it was just between the two...Read On


Being Sissy To My Brother In Law

Caught in panties, bsque and stockings.

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are...Read On


Lisa Lee Xdressing Adventures

I just love crossdressing sex!

    I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it!   I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I...Read On


Fulfilling A Girl's Male Fantasy Part 1

Jennifer has a surprise request for Jack.

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at home, so we locked her door and did our best to keep quiet as we fucked the night away. Now it was noon,...Read On


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


My First Time - Part 2, or The Beginning

Once was not enough

It was about two weeks after Halloween that the dreams began. I began to dream about being transformed again. I was able to recall the feel of the silky garment against my skin, the sensation of the nylons brushing against each other as I walked. I recalled all the women at the party who danced with me and rubbed my silk covered ass. "You feel like a real girl," more than one said, and I...Read On


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


A Night at the Ambassador

An early evening of debauchery earns kudos for a crossdresser.

While on business in Colorado Springs, I had the opportunity to visit one of the adult theaters that I had visited previously. Although the booth area was in full swing, the booths had no doors and there was no privacy what so ever. One could still have a good time if they were so inclined. The attendants were cool and they did not mind the actions of others as long as there were...Read On