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Crossdressing

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62

Do you want to wear my skirt?

Katie caught me looking at her skirt and made me wear it.

As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself....Read On

48

Born To Be A Babe: Part Two

Wearing a sexy pair of hot pants, I go looking for men at the adult bookstore.

After discovering that I enjoyed wearing sexy little panties, tasting cum and having a big vibrator in my ass, I began to have these auto-erotic sessions, every day.While wearing panties and playing with my ass with a dildo, I would lay in my bed and fantasize about all the big cocks I wanted to satisfy for men. While I was only 16 years-old, I had decided I was a girl and I wanted to wear...Read On

10

Caught and the Consequences Part 2

Crossdresser caught by wife finding our what she has in store for him

Part 2   While sitting there I went through the usual stages, despair that I had been caught, fright as to what would happen next, would she still want me as her husband or was this going to be a third divorce, and that made me feel very sad as it suddenly dawned on me how much I loved her and I quietly resolved to do anything I could to save my marriage.   ...Read On

86

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...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

36

Two girlfriends have a couple over for a fun night

Wife sets up night for us to be girlfriends, then invites another couple over for fun

My wife Dawn had surprised me by saying we were spending the night in as two girlfriends, laying out my clothes so we matched. Then after having amazing sex, Dawn surprised me by telling me that she had invited her friend, Maria, and Maria’s husband, Mark, over for some fun with the two of us and to fulfill the fantasies of all of us. So I was standing there with my red plaid skirt,...Read On

Mistress Hannah's Pathetic Husband

She found my porn stash and now I must pay

My life had become miserable. It had taken two years of marriage for it to happen, but it had become much worse in the past few months. The worst part about it was that it was clear that my sweet wife's life had also become miserable and that she thought it was my fault. And maybe it was, but I didn't know why. I suspected it was because I'm a miserable example of a man and she deserves...Read On

10

Crossdress boy's ultimate romp

Humiliated cross dresser discovers a new fetish

He was in his late 20s.. I'm in my late teens. the thought of meeting him really didn’t come across my mind. however I was won over by his passion and sincerity and he doesn’t even mind if I didn’t shave my legs! wow! we arranged to meet at the car park near my place, he asked me to wait for him and he'll reach in about 45mins. I went straight to my aunts drawer, looking for my favourite...Read On

18

My birthday treat

After months of helping me dress, my neighbour plans a special night.

My next door neighbour had begun helping me with my crossdressing by buying me my own clothes, and despite her initial stipulation that I continue to dress in secret, we had experienced a moment where that had all changed. Once that day had passed, Ellie and I became almost inseparable. If we weren't together, we were texting or talking on the phone. We would do everything an ordinary pair...Read On

23

Caught By My Girlfriend

Hitting puberty late in high school had its disadvantages. A slender, almost feminine body and a small dick was not something a lot of women tended to go for, however, I was lucky enough to find Adrian. We hit it off right away, shared many things in common and we couldn’t get enough of each other. She was gorgeous, standing at six feet, she was just as tall as me. Her beautiful crystal blue...Read On

32

Friend Becomes My First Part 1

The true story of one my best friends becoming my first

*This is a true story of my first time having sex dressed a girl* It finally happened, and it was a dream come true. I started dressing as a girl when I was 17. For me, it started with a thong I stole from my mom's drawer which eventually went on to lingerie, to normal clothes, and all the way to dressing fully. Im now 24, and all I wanted to do was to show myself to a man and be the little...Read On

63

The Perfect Choice

A girl works to turn her boyfriend into her toy

Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to turn Andrew on, and it was working perfectly.She hadn't slept with him yet and the tension...Read On

39

She wears the pants, over her cock

I stepped off the plane after three days travelling and was looking forward to going home after a long few weeks of travelling for work. My work regularly has me travelling and I don’t seem to get home as much as I would like anymore.   But it does make it even more enjoyable when I do get home.   Leaving the gate, I walked down the corridor, past the last security checkpoint, and toward...Read On

68

A surprise ass-fucking in panties

A friend displays her kinkier side

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like...Read On

44

Total Sub CD Slut

His total sub CD slut

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend. I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends. I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me...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

7

Satin lingerie

My sexy pink satin panties felt so good against my skin and looked great with black stockings and garter belt, my matching satin camisole top was so soft and I was gently creasing my pert nipples through the fabric. It was around 10pm and I was feeling a little bit tipsy after my bottle of wine The DVD was playing Cock in Frock and had some sexy clad shemales in...Read On

16

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

9

s(he) finds her man

story when i replaced my friend at a wedding

My house was not more than 250 meters away from the bus stop where I got down; but the sudden and heavy downpour caught me totally unprepared. Being one those new housing colonies there were no houses or trees where I could take shelter. By the time I reached our new house I was drenched to my skin. My younger sister Putti who opened the door started laughing at my plight. My elder...Read On

37

The Awakening of Susi

Susi discovers the joys of anonymous cock sucking at a glory hole (true story)

Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I had many female friends who loved to dress me up in their sexy clothes and strut me around in front of their boyfriends. They thought it was cute to see me in full makeup and a wig wearing a...Read On

12

My First Thong

How the thong panty changed my sex life so young

When I was a little boy in grade school, I developed a curiosity so strong that it could not dare be mentioned to my parents...well, except for my father, since he was quite a perv despite being married to my mother who was more conservative than he was. Typical behaviors in a hispanic couple's life, really. No, it was not about my sexuality, but it involved underwear. Specifically, a...Read On

15

felix becomes felicity

bullied into becoming a girl!

FELIX  becomes FELICITY Chapter 1 “Gynecomastia is the abnormally large development of mammary glands in males, resulting in breast enlargement……… In teenage boys this does not have to be linked to obesity……… The word Gynecomastia  derives from the Greek for woman and breast”     I logged off from my regular searches on the internet and felt sick as usual. I am 16 and a normal...Read On

37

Wife's crossdressing fantasy Part 3

I had to find a way to repay my wife for the wonderful anniversary gift she game me.

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her,...Read On

10

A weekend with Nancy: part 2

Nancy, that was the best blow job I ever had, she's awesome, Dan replied.

 Nancy informed Alice that she would be using the bedroom to dress me, and that she should pick out an outfit consisting of no fewer than seven articles, gather her make-up and whatever else she required and then use another room to get dressed. Furthermore, Nancy informed Alice if she didn't like what she was wearing when she returned that she would be punished, and to not waste any...Read On

23

Caribbean Vacation part 1

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

Susan & I often traveledto the Caribbean for our vacations. We loved the laid back atmosphere and all the sun and gorgeous beaches. Last year though we arrived to find that the airline had lost my only bag containing all my clothing including my swim suit! Imagine arriving in the Caribbean without even having a swim suit to wear! I had just resigned myself to going down to the gift shop...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

19

Minding the House

Short true story about the fun I got up to while minding my neighbour's house

My neighbours Tom and Paula were going away on vacation and they asked me to keep an eye on the house for them. I gladly accepted as I wanted to see what their house was like on the inside but my curiosity really lay in exploring Paula's underwear collection. Paula was a 34 year old pretty mom of two kids, 5ft 7 with blue eyes and shoulder length brown hair. She possessed a slim but...Read On

13

A helping hand

Found out by a mature woman

It all started a few years ago. I was dating a girl who was bisexual. So much so that she wanted me dressed as a woman for sex. To begin with I was not sure, but eventually I came round to the idea. It was mainly just some lipstick and perfume. After a few months we split up, but I continued to dress up. One day I decided to venture out as a woman. I lay in bed thinking what I should wear....Read On

17

First Time Out

Crossdressing In Public

 This is a true story about my first time I went out dressed at a club I had been in the closet for years and up until this point only a few people had ever seen me dressed my freind Bill and some guys I went to an adult book store.  I had been dressing for Bill alot in mine and his apartment but I had this erge to go out clubbing dressed I had asked Bill several times but it seemed he...Read On

17

Date with my wife - her story

Today started like any other day, except for one thing. My husband informed me as he brought me morning coffee, "Sweetheart, tonight when you come home, go straight upstairs, cleanup and put on the outfit I have laid out on the bed." He said this with a grin on his face. You know that grin like the one you see on a child's face as you enter the candy store. "But what if I need something?"...Read On