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My Early Story

My girlfriend helps me learn and explore.

From my earliest memory, I liked trying on girls' things. My mom’s slips, sister’s panties, even my aunt’s nightie, (that is another story). I even went as far as dressing up completely when I was home alone. Mostly I wore my sister’s things. I loved her short shorts and halter tops. We were about the same size even though I was a year older. I didn't necessarily want to be a girl, just dress...Read On


My First Time with a cross dresser

Introduction to crossdressers

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers. Now I am in my late teens and at college. One day my Dad made a pot of tea and breakfast.“Did you...Read On


Put it on!

A not-so-reluctant housemate dresses for his live-in landlord

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and...Read On

Audio version available

My first time

First time with a CD. First gay experience.

My first story. And it is the true story of my first encounter with a CD. With a click of the mouse, I had committed… I was going to meet a cross dresser just a few miles from home. Could I go through with it? Is it really what I wanted? Who was I kidding? Of course I wanted it. Now it was time to just suck it up, princess. I took a quick shower and the dressed in my tiniest,...Read On


Confessions of a Ladyboy - Part 1

He helps me resolve my boy/girl confused sexuality dilemma

I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to remember such things. She taught me some valuable lessons - how to be attractive, how to carry myself, how to be seductive, how to do my makeup. She always said, "You are such a cute boy, you...Read On


Seducing Uncle Frank

A tale of a Crossdresser seducing his attractive Uncle.

This is a story that happened some time ago, when I seduced my Uncle Frank. Uncle Frank Uncle Frank was married to my mum's sister. He was about 10 years older than Aunt May, and it was both their second marriages. Uncle Frank had an Italian father, French mother, three older sisters, loads of nephews and nieces, and had property in Kensington, the Algarve, and Telluride. You could say he...Read On


All the Way (Part 1)

Kathy makes Richard pay the price

I'd only been married a little over a year when my wife came home early and found me jacking off using a pair of her panties and to be sure, this wasn't the first time. There I was lying in bed with her wispy little nylon panties wrapped around my dick and cumming like nobody's business. I was so wrapped up in my own pleasure that I hadn't even noticed her standing in the doorway watching me. ...Read On



Found out and 'forced' to educate respected women in village - inc vicar's wife.

CAUGHT WEARING MY UNDIES. Having recently been left quite a large sum of money by my late aunt in her will, I decided to buy my own house, and start my own business as a handyman. Because I was bored with my present location in the north of England, I moved down to the midlands and bought a very nice isolated cottage about 20 miles south of Birmingham on the outskirts of a...Read On


First Time Bareback

The first time I let my boyfriend fuck me bareback

I have written an earlier story about the first time my boyfriend Mike and I fucked. After our first encounter, I couldn't get enough of Mike and his cock. We went from meeting every other week to him spending some weekends at my house with me dressed the entire time. As we got to know each other better, we started to discuss our sexual histories and some of our fantasies. I could tell Mike...Read On


Telling Mom I'm A Crossdresser Part 8.5: Cops and Prostitutes

What Missy needs to do instead of going to jail for prostitution. (continue of part 8)

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan. “We can definitely let him have a free night in exchange for not getting a criminal...Read On


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


Jessie's Fantasy: Chapter 6 Turning the Tables

Now that Jessie fooled his friends, who will turn the table on whom?

I was floored by what Tracy had said to me. “Because, the male Jesse is no more for the time being, it is womanly Jessie that needs to go.” It seemed that my love just told me that I had to meet up with my male friends tonight. My mind was going a mile a minute. I already fooled my friends once. But can I do it again? If I do, what is going to happen? What will I let happen? My stomach felt...Read On


Extended Vacation Chapter 3

Cassie continues her new life

Cassie has her first full day as a woman as she continues her seven weeks living as a woman 24/7. EXTENDED VACATION Chapter 3 I arrived at my new apartment around 5 PM, and it took me over three hours to unpack and get organized. It was very enjoyable to move in and have a fresh start. I loved looking at my closet and all of my drawers as everything was for Cassie. My bathroom...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


What Do You Do When....

The weekend arrives and mom and dad are going out and I assume they are going to one of their swinger parties and won't be home until early the next morning. So I do my normal thing when they are gone and play dress up and go out and hunt for dick. But this time I knew they would be gone and had already planned an evening of fun with a couple of guys I had met at the adult bookstore my...Read On


What a Girl Wants

'Katie' finally fulfills her fantasy of having sex with a man.

"Come on, Katie. Give in to your desires. You've gone this far. You're almost there. You're so close to your goals and dreams of being treated like a lady. Accept it. Embrace it. Give in and complete your journey. Tell me what you want." Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I'd seen him and it...Read On



My first time in panties

We had just finished making love, but Amy was still not satisfied. “I wasn’t done,” She complained. “You came too soon! Let’s go at it again.” “You know that I can’t get hard again this quickly. It will take me a couple of hours to recharge my batteries before I can fuck you again.” I replied. “That is completely unacceptable.” she pouted. “There must be something that we can do. I...Read On


My second visit to Bill's

This is the second part of Picked up in the toilets.

Here I was waiting to meet Simon, I had turned up an hour early. God I was keen after the week before, I just wanted more of the same. My mind whirred over wondering how many cocks I would suck and whether Debbie would suck me again. Would she tie me up this time? I just couldn't wait. Eventually Simon pulled up at the arranged place just like he said he would. I got into the car and we set...Read On


Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also...Read On


Cruising The Drive In

It was a Friday night and all of my friends were at home with family. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight. The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from...Read On


Changing Room

I had finally worked up the courage to explain to my wife that I liked to wear panties. I dressed off and on in her clothes for years, and she didn't suspect a thing. Before that, when I was single, I had taken to snatching the odd pair of panties out of the dryer in whatever apartment building I was living at the time. When I was a little boy I had always wanted to be pretty like a girl,...Read On



A crossdresser finds himself punished.

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in...Read On


A Saturday Afternoon Visit to the Office

I get to let the sissy in me cum out during a Saturday afternoon visit to the office

I usually work from home as I have a very private place with a wonderful view and Lord knows I’ve put in more than my fair share of office hours over the years. But I do occasionally elect to make visits to the office both during normal office hours and off-hours to make copies, restock my home supplies and have a cup of coffee with a long-term friend or two. Usually when I do hit the office,...Read On


Felix becomes Felicity - Chapter 6

FELIX  becomes FELICITY Chapter 6 ..I put the gingham dress on that fit well and completed the ensemble with the shoes and cardigan. I looked like a fully grown woman in a school girl outfit. My breasts seemed to project and fill the dress with the buttons on the front tight. The fabric belt pinched in my already slim waste and the skirt part of the dress flared slightly emphasizing my...Read On


Dressmaker's Dummy

Girls always knows best

I was happy now that Kasia and I had moved in together. Not only did it mean that we no longer had to take turns going to each other’s place, but it also meant that I had closer access to a supply of her soiled panties. Kasia was a cute Polish girl, 23 years old, with deep blue eyes, shoulder-length hair trimmed in a cute bob, and a body to die for. We had decided trying to live together to...Read On


the day i became Suzie chapter 4

this is my fantasy

I went back the next day dressed sexier than ever, but Jack and Harry did not show up. I waited for hours. Then cried all the way home. I cried myself to sleep three nights in a row. Now I knew how a women feel after being fucked then forgotten. But then on the fourth day Harry called. I instantly went into my sweetest voice and asked, "Where have you been?" "Guy stuff Suzie.You...Read On


A Nanny Femtastic! - Chapter 11

A NANNY FEMTASTIC! Chapter 11 We walked to the harbour and found the boat. There were too bulky security guards checking people as they entered. The boat was in fact a massive cruiser! We joined the queue, it was obviously not a little gathering. The other women were dressed in classy whites and float summer dresses, we looked like too cheap hookers! “Trinity this was a...Read On


Jessie's Fantasy: Chapter 3 The Night Club

Jessie's all set for her first night out. Will she catch a guy or be caught?

After an amazing afternoon with Tracy, Suzy, and Brooke regarding my transformation and amazing feminization via sexual acts that wore me out, it was time to meet my friends. Before we left, I called my friend John and told him that female Jesse would have to wait. I told him a little white lie that I had developed stomach flu and had been throwing up all afternoon. John told me that he...Read On


The Foreigner

His accent was strong, but his hands were stronger.

I had been chatting online with him for a while now, and he was keen to meet me. He identified as straight and was married, which is normally a deal breaker for me, but he was persistent. After a lot of chatting, I agreed to meet him at his place. When I arrived, he buzzed me into the building, and I went upstairs to find he had left the door ajar for me. Nervously, I went in. His place was...Read On


Caught, Used and Loving It!

I was caught dressing up as female and used like a toy

I knew I had time now; my wife had gone out with her friendsand wouldn’t be back until 10pm at the earliest. As it was only 6:30, I knew I could spend time getting ready before playing around on the computer and enjoying a nice relaxing but exciting orgasm. My cock was more than ready as I hadn’t had sex for over a week and no chance to masturbate either due to either the kids being around or...Read On