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Memoirs of a Crossdresser: Chapter 1

My True Story Chapter 1:  I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should...Read On


First Love

Crossdressers first love

This is the story of the first time my first boyfriend and I fucked. Before I get started I should give you some background information about myself. I had always considered myself straight and had been happily married for fifteen years before my wife and I drifted apart and divorced. While we were married I had wondered what wearing some of her heels would be like. Unfortunately my feet were...Read On


Telling Mom I'm A Crossdresser Part 11: Girl time

sorry it took so long and that its a bit longer then my last one but I hope you enjoy. com at bottom

Part 11 It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended. I walked in the door...Read On


My First Glory Hole

Sucking off strangers.

I have thought about it for sometime about going to a glory hole while dressed en-femme. Naturally, the problem was where to find one or what adult book store would have one. I knew that I would have to drive some miles to find one. So after doing some research online, I was able to find one that was about a forty-five minute drive from my house. After rationalizing and convincing myself that...Read On


A friend with something extra.

Ian makes a discovery about his boyhood friend.

So here Ian was standing in the doorway to his buddy's room and staring at this drop dead hottie clad in silk, lace and heels that he found inside. It was just a typical Friday and he'd dropped over his friend's house for a pizza and movie night. It was a rotating event for them on Fridays. They didn't have their own cars as of yet and had no desire to walk to the mall and hang out....Read On


Telling Mom I'm A Crossdresser Part 8: Bus Driver's and Cops

Part 8 enjoy and please comment at the bottom ;)

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I...Read On


Webmeets Diary Ch. 03

I become Sarah to meet an older couple.

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. I'd been using the swingers' site for more than a...Read On


Not What You Think I Am

Excited by the young looking woman who is such a surprise.

Marriage can be a lonely place, two folks living together and yet being so far apart. It never used to be like that but I guess it comes with the ageing process; a mid-life crisis. To overcome our frustrations, my wife decided we would spend more time together away from our comfortable home, so one weekend every month we hire a log cabin at a campsite that sits between the forest and the lake....Read On


Carl, Carla and Hannah - Epilogue

The conclusion.

It's now been nearly a year since Hannah and I got married, and my goodness, what a year it's been! As soon as we reached the Bahamas on our honeymoon, Hannah and I (as Carla, naturally) had an absolute wonderful time. The days were full of warm sunshine, and the nights were full of... well, I think you can guess! When we got back, my plan to live full-time as Carla started well. After a...Read On


Tammy, Lisa, and Karen part 3

Please read: Tammy, Lisa, and Karen part 1 and 2 first

I woke up the next morning with Lisa sucking on my little clitty, making it hard. I pulled her panties to the side and began to kiss her beautiful pussy and suck and lick on her clit. I began to plunge my tongue as deep as I could into her hot wet honey hole. Lisa was about to make me cum, then she stopped. She knew just where my breaking point was. She turned around and sat down on my...Read On


A New Chapter

Sensual Bliss

A few things have changed. One, I have accepted my desire and need to fulfill that urge to become feminine and girly. Two, having accepted that, I also had to invest to make myself look, and become as girly as I could. That led me on a near year pursuit to create a better feminine appearance than just using two suntan body stocking to shape and hold my feminine curves. After months...Read On


Becoming Chloe - Part 5

Friday night - part one

I got home, tired and cold from work, only to find Vickie already there. That in itself was unusual, because she normally didn't get home until after me. Before I'd even taken my coat off, she greeted me with a really passionate kiss, then turned me round and pushed me back through the front door. "Where are we going?" I asked, but she just gave me a big, mischievous grin. "Out." We got...Read On


She Made Me Do It

My package arrived in the post – I just couldn’t wait to open it.

Something inside me just grabbed hold of my male shackles and snapped them in two; discarding them into the depths of depravity. I had been writing stories about crossdressing and transsexuals all week. I had been looking at girly pictures, not the feminine girl ones, the ones that had dicks. Some of them were absolutely gorgeous, far better looking than some women and I wanted to be one of...Read On



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

Mistress Hannah's Pathetic Husband Part 6

Mistress Leelee uses me hard.

Having accepted the riding crop, Mistress Leelee seemed to understand that she was being given the opportunity to do something to me, but she was clearly lost. "He's yours now Leelee. It starts with the first order. If you're going to turn your cheating husband, a little experience with Michelle here will give you confidence. I suggest you order him to stand in front of you and work from...Read On


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


Becoming Chloe - Part 3

Chloe gets her name - and much more...

When we arrived home, I was desperate to change, but Vickie said no, much to my frustration. The rest of the afternoon went like any other Saturday, and after dinner, we sat and watched tv for a while. Around nine o'clock, Vickie got up and suggested that we have an early night. By now my frustration had almost abated, so I followed her upstairs and we both got ready for bed. I was delighted...Read On


Night on the Town

The girls and I go out to a lesbian bar.

Night on the Town Barbara Marsh “Well, come on, chicken!” I responded, “Cluck, cluck.” Okay, so I know it’s not original, but it was the best I could do. Despite my misgivings, I got out of the minivan, smoothed my skirt across my hips, and waited for Alexis. Her name’s really Alice, but she was Alexis for the night. The same way Jeanna was Gina and I was Betinna. I don’t...Read On


Ever tried dogging?

The trilogy concludes with a hot threesome in a Steam Room and a late-night bukkake

Nick steered his sleek silver turbo-charged coupe across the deserted Cambridgeshire by-roads towards Ely. The town was justly known as 'the ship of the Fens', as the tower of its majestic 16th century cathedral was like a navigational lode star. Ely's train station was only a few hundred yards from the cathedral and Cathy stood waiting in the shade of the station building's canopy. She wore...Read On


Michelle Gives It Up

Michelle provides him with everything she has to ffer

When my best friend, Jimmy, left my house late that afternoon he was a very well satisfied guy, sexually. For the two years prior we'd had quite a few mutual masturbation sessions. This had progressed from jacking off while talking about various girls we knew in school to jacking off each other. Of course, at that time neither of us had actually done anything with a girl, but that never slowed...Read On

An Introduction to Crossdressing Pt 3

After all the preparation I want it too bad to go out.

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any...Read On


Mariah... My Wank Mistress

How I met Mariah, a crossdresser's dream...

We first made contact about three years ago, on one of those dirty dating sites. I was showing my tranny profile, Velvet, at the time, and was being hit on by a bunch of dirty old men, when this "Mariah" person said, "Hi." I was in a pretty sarcastic mood at the time, and was slightly peed off, as the guys I had been chatting to were only interested in one thing, getting their rocks-off. ...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


Once Again in silk Part 2

As sundown approached on Saturday I showered and got ready to attend the opening of an art gallery that a member of our organization was sponsoring. I selected the suit, shirt and tie and then I retrieved the white silk panties from the laundry room. I wonder if Darlene questioned herself on the fact that I accepted her request without protest? They were beautiful and just running my...Read On


Car Park No 1

My crossdressing dream

The Car Park No 1 The car park has always been a great place for meeting a fellow for a good time. I had been there several times over the years and felt a great satisfaction in satisfying the needs of a horny participant. It has become more of a challenge since the police seem to patrol it more often than in past years. However, I had the opportunity to have a few hours to my self as my...Read On


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


My 2 AM Phone Call

Sissy cross-dresser is told to report to a motel at 2 AM

It was about 2 AM when the phone rang. The voice on the other end simply said to get dressed. He told me exactly what to wear. Exactly. He wanted me in a black micro mini skirt, little black mesh top that barely came below my nipples, five inch platform heels, lots of junk jewelry and a bushy Vegas platinum blonde wig. He said to come to the Diamond Motel on the Gulf Freeway and then he hung...Read On


My Foggy Late Night Story

On a foggy late night, Sasha gets fit, lucky, and... loved?

It was a cold, wet December night. Here I was in my room, feeling exhausted, and laying on my bed doing the whole Netflix and chill thing. I had just pulled a long afternoon and evening event with my college study group. We spent the day as total masochists painfully cramming whatever we could into our tired brains for our finals. It had worn me out so much that I didn’t want to do...Read On


The Engineering Costume Party: Part 2

A college freshman gets more than he bargained for.

After realizing I might be the only guy dressed as a skank for the Skanks and Robots Party I timidly waited in the dorm room and “pre-gamed” with Anthony and Jillian for the upcoming festivities. I drank vodka and cranberry with Jillian while Anthony had beer. I hoped some “liquid courage” would help me to feel more comfortable going to the party dressed in such a slutty outfit. Now, I...Read On


Sexy Stewardess on a Hot Flight: Part One

Working as a tranny call boy leads to a high flying adventure.

After arriving in Los Angeles, I became a tranny call boy to support myself. Working for an agency, I was sent to perform sex on many older rich men. Being a hot twenty year-old tranny slut with fresh meat in my panties, I instantly became one of the more popular call boys in the agency. Some men even took me out on dates for dinner then back their places or motel rooms for lots of sexy...Read On