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Crossdressing

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40

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

37

Feminized

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

30

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

30

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

24

CAUGHT WEARING MY UNDIES.

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

24

The Compromise: Part 1

A suggestion from a counselor sets in motion a fantasy compromise that changes my life forever.

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. ...Read On

23

Switching roles

She dresses up as a policewoman and plays the dominant part

In most play I tend towards the dominant side but I do like to switch from time to time. One of the most intense experiences of my life, not so very long ago, was an unexpected switch. Halloween night. I traveled by train to visit with my lover. She'd made all the arrangements for costumes for us to attend a party later that evening. I didn't know what she chosen or anything about the...Read On

14

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

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

14

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

14

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

14

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

14

How It Started

I looked and saw her panties in the hamper.

At twenty five and being a blonde haired blue eyed light skinned guy, I had little hair except on my head. So, it didn't take long to achieve the smooth feminine look that I wanted. Of course, I left some "down below" because I looked young and if I shaved it all off I feared looking underage. My blonde hair was long, during the week I wore it in a guy style. On the weekends it was different,...Read On

14

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

60

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

45

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

35

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

29

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

29

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

13

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

13

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

13

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

13

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

13

Becoming Chloe - Part 19

Tina and Vickie have some news, and Chloe has an interesting evening...

You know, they say that the thing about working in a sweet shop is that you soon seem to lose your appetite for sweets. Well, working in a sex store is pretty similar experience. At first, I was amazed at the variety and array of different toys, magazines, DVD's, clothes and nick-nacks that were available. After a while, however, I began to be less and less amazed (and aroused!) by the things...Read On

13

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

87

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

41

The Adult Theatre

A true story with the name and location changed for a good lush friend.

I got to the hotel early so that I could get myself fully prepared to meet a guy I had been chatting with via a chat room. I decided to wear my favorite pink check mini skirt with my sexiest pink undies to match. I added a white silk blouse and a white garter belt with some white stockings. I took time applying my make up, making sure I had dark sultry eyes and perfect red lips, I wanted to...Read On

33

Andrew to Andrea - Part 4

...the next few steps...

Chapter 4 It seemed like the time would never arrive. I watched the clock limp around the dial for the last hour between 5 and 6, but finally the time came…the time to go home. I still felt the pressure, not unpleasantly, of the plug installed by my wife yesterday, and still had the memories of the sensations that I felt each time she activated it…again, not unpleasant. Finally, I had the...Read On

21

Learning to be submissive - part 1

A gift comes at a cost

Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can't speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would...Read On

21

An Uneven Romance - Part Two

He's taken further into her strange, kinky world

“Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night before. Sarah was a pretty special girl; after a night spent with my head between her legs she had eventually let me cum this morning. She’d somehow coaxed me into wearing her wet panties from...Read On