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Crossdressing

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation.

15

Ashley's BBC Therapy

Her destiny gets fulfilled.

I couldn't breathe, my whole midsection was tensing up as he deepened inside me. I moaned and expelled all the air from my lungs and took a deep breath. I already knew that this would be a challenge but I had no idea that it would be so enormous. He was an alpha, by all means, he shoved it inside and split me open like I was disposable, which I was to him most likely. But why do I care? I'm...Read On

17

OMG Last Night

last night a first for me

I suppose I'd better start at the beginning. Well, my femme name is Carly Hughes.I'm a 47-year-old male who has probably been cross-dressing since he was seven. I started dressing in my mum's and sister's clothes. I've built up stashes of clothes many times and binned them through guilt. I've probably wasted so much cash it's unbelievable. Anyway, I've done all the manly things in my life...Read On

15

The Cardboard Fort. The conclusion.

The conclusion of the story told to The Phantom.

My duo identity was not an easy thing to maintain. My lingerie was washed in the half bath sink in the wee hours of the morning. I then had to creep downstairs and hang them in the fort. They along with the wig and makeup were kept hidden in an old suitcase with a working lock I found in the second-hand store. All this secrecy was necessary because young men did not want to dress and...Read On

13

The Cardboard Fort. Part 2

The story told to The Phantom continues.

That evening I thought about Gene and what had happened in their old fort. I finally had the opportunity to wear something besides the slip I  had shoplifted. I really enjoyed dressing up for his friend and what had happened as a result. I didn't feel weird or strange about it. "Maybe I should have been born a girl." I mused before falling asleep. Two days later Gene appeared at my door...Read On

19

The Cardboard Fort

A story from the sixties as told to The Phantom.

I discovered at a young age that I had a desire to wear female clothing, but not just any clothing, it had to be silk and or satin. I thought maybe it was a phase I was going through. I figured if I ignored these desires they would pass. Ignoring them didn't work and they became more intense.  I often found myself sitting and staring at the lingerie section of the large Sears catalogue with...Read On

5

My Road to Cross-dressing (Part 3)

Part three of my cross-dressing saga, where I have sex as a woman.

From the first time I dressed, there was always a sexual element. I used to find the time to wear something feminine and wank myself. It went hand in hand, so to speak. One of the things I loved doing was getting dressed up and laying on my bed with my legs over my head and wanking. When it was time, I would cum in my own mouth. I did it so many times but it was always uncomfortable, but I...Read On

3

My Road to Cross-dressing (part 2)

A more in depth follow-up to my original story about how I started cross dressing.

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera. Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he...Read On

13

A Night to Remember or to Forget?

A pretty transvestite finds herself getting a little too comfortable out on the town!

As a petite, pretty, and now fairly confident young transvestite, I feel fortunate to have discovered so many things about myself. I am proud to have a slim, smooth and well-exercised shape. I have longish streaked blonde hair and my goal is to always develop and improve my feminine elegance. My friends tell me I possess a very strong believability in my appearance as a young woman. I think...Read On

12

Chasing Skirts

Sam's crush, Heidi, turns out to be a girl with unusual tastes.

When I entered college, I was a virgin. Not to say it was particularly unusual; I was a quiet, nerdy kid. I wasn’t ugly by any stretch of the imagination, but a little short, not very masculine, a little self-conscious and not hugely used to interacting with girls. I was eager to change this fact, but I felt like something of a romantic; I didn’t want a random hook-up, and besides, I...Read On

9

Be Careful What You Wish For

A say in my life.

When I arrived home I noticed a note on my computer. It read, "Take off your clothes and put them in the washer. Go to the bathroom and shower, then go to the bedroom and put on the clothes laid out for you. Make sure My toys are prepared and in the right places, then you may join Me in the living room bringing your hood with you and taking your place at My feet (on your knees, hands behind...Read On

13

Caught And Punished By My Manager (Part 2)

I had to make a sale...

I lay there on the floor, my g-string still dangling around my ankles, my vibrator rammed deep inside my ass. My boss Mei had been gone all morning, leaving me vulnerable and exposed in my lace garter chemise set, sheer stockings and high heels.  I lay there staring at myself in one of the mirrors. I felt so feminine and slutty as I wriggled my bum against the floor and rubbed my...Read On

3

Happy To Be Used (Pt. 7)

I practice my dance and slut moves at the bachelor party.

  Bachelor party Friday was finally here. I would have woken up early, but I had partied really hard the night before and so I woke up with a crazy hangover. Good thing I had until that night to recover and get ready for my performance. Being hungover turned out to be a blessing in disguise because rather than doing anything all day and using up my energy, I essentially sat around the...Read On

22

Dressing up.

dressing up in sisters clothes

It was the summer of my sixteenth birthday. It was when I first thought of girls’ clothing as the clothes I would like to wear. My name is Matt and I live with my three sisters and mother. I am the youngest and as you may realize in this sort of set up, there is no shortage of girls’ clothing for me try on. I had just turned sixteen and it was summer. As usual, the four beautiful women in...Read On

A Freebie for Randy - continued

I was becoming addicted to Randy.

The Saturday morning after giving Randy a freebie I awoke feeling happy and very horny. I was still lying in bed enjoying the smooth feel of my soft skin and the silk camisole and panty set that I put on before bed.  While I was having a good time with myself and my favorite dildo, I heard a knock on the door.  Leaning towards the window I saw the UPS man walking back towards his truck, and...Read On

14

Andrew-Andrea

A boy's experiences through petticoating, boy-boy love and back to femininity.

My mum and I lived on the outskirts of a small Scottish village. John and his mother Beth were our neighbors, and he and I were best friends from an early age, sharing everything as we grew up. At Primary School and then Senior Secondary School, we were an inseparable pair, supporting each other through the good and bad times. This idyll came to an end when we had just turned sixteen. He and...Read On

17

Lisa's Lessons

A webcam crossdresser begins to learn more about himself with the help of a generous teacher.

I used to spend a lot of time away from home for my job. It had its downsides, but it gave me a chance to do my favourite thing: show off. My toolbox had a locked compartment containing a small selection of cam-suitable wardrobe items: a single camisole, a few panties, and two pairs of nylons - one thigh-high and the other to the waist. I travelled a mostly predictable route, so I was a...Read On

11

I Dressed Charlie Like A Girl And She Never Went Back

I always protected Charlene through college, before I knew she was to be my girl.

Today is our long awaited graduation exercises. I am just waking up from last night's party, Charlene is already up and in the shower. Not surprising, because she always loves to look her best in the morning. This morning was going to be very special in honor of graduation and celebration of our almost four-year love affair. Well, at least that's what she promised. I kicked off the sheets...Read On

27

Husband Caught Cheating, Punished

Husband used by wife and her friends

This is what happens when you get caught cheating on your wife. I love my wife dearly and never set out to hurt her. I was working away from home several years ago, and while I was away I became chatty with a lady at a nearby bar. Her name was Helen; she was very well spoken and was gorgeous. I had been visiting the bar for a drink most days after work, and Helen always seemed to be there. I...Read On

8

Part 1: Abandoned Parking Lot

It begins... Well, I found out that Anne fucked that professor again. She came to my dorm, drunk at 3 am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won’t even get started on what she was on about. I tried calming her down, but whenever I said anything she just slapped me, or if I tried to stop her from drinking more from her loaded thermos,...Read On

12

A Crossdresser Gets Caught

A closet crossdresser gets caught and has the time of her life.

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him.  He found women attractive and loved them wearing...Read On

4

Happy to be Used (Pt. 6)

An educational strip club trip

  Sir now knew I was his slut and would question nothing he told me to do. Though I presume this excited him, there is no way it excited him as much as it excited me. I was distracted every waking minute thinking about past experiences and future erotic scenes to come. I spent hours day dreaming and was masturbating at least four times a day. Every time I masturbated I shoved something up...Read On

7

Crazy Sex Affair With Her Sister Part 2

Our lingerie affair continues...

I'd just spent the night with my girlfriend's beautiful and sexy sister Miriam, exploring her lingerie collection and her amazing body. We'd been playing dress up for hours. She would change her outfit and pass me some new clothes, a pair of frilly knickers and a baby doll, a bra and matching thong, a skirt, some stockings, fucking each other along the way. I wasn't sure what time it was but...Read On

13

Digging up the past gets me all dirty!

My jealousy about her past changes my future

My wife Cindy had a sexual past before we met. I'd only been with a couple of girls before her but her sexual history was epic. I overheard her talking about me to one of her friends once and she said that I was the sensible choice. I was safe, I had a job, I wasn't going to treat her bad or cheat on her. Everyone has to settle down sometime. What hurt the most, though, was how little...Read On

12

Wife Makes My Dream Come True

After a long wait of ten years, my wife finally comes to terms with my fantasy and makes me her girl

I had a fantasy for dressing up since puberty hit me. I wanted to crossdress even before I knew what it meant. I always dreamt of wearing sexy feminine clothes. I could never try any female clothes at that time though, but the curiosity in me never died. When I started dating my wife, I once gathered the courage and told her my fantasy. I am sure she did not expect that and was rather...Read On

16

Caught and punished by my manager

The power goes to her head

My job as a sales rep meant I had to work away a lot, traveling around the country to various events and conferences. It suited my lifestyle as it meant I was able to indulge in my secret obsession of crossdressing.  Every week I'd pack my suitcase with a new outfit of sexy lingerie, heels, wigs, makeup, a vibrating cock; all the things I’d need to satisfy my sexual urges each night when...Read On

16

The Wedding Gift Surprise

A wedding to remember

I'd been invited to my friend Whitney's wedding, I didn't really know anyone and had only met her fiance once before in passing. I think she only invited me to show off how popular she was and to be honest she was known for being a bit of an attention seeker. After the ceremony we all started to drink and I was getting quite tipsy, which meant I was also starting to feel horny. I left the...Read On

20

Almost Caught And Forced To Watch Cheating Wife!

Secrets almost revealed, with a happy ending!

It was our monthly weekend away. My wife was going to visit her friend Karla and I was going out of town to see my friends in another city. At least that's what she thought. Really, I would be using the precious time alone to indulge in my secret addiction. I kissed her on the cheek and said goodbye as we both got into our cars and drove off. I did my usual trick of driving round the...Read On

25

Crazy Sex Affair With Her Sister

Finding a girl who shared my love of lingerie.

My girlfriend Lisa and I met at a club when both fairly drunk. She came home with me and we fucked on the first night. It was nothing special but she was desperate to get with me and would put out anytime I wanted, so we carried on dating for a few weeks. The sex was ok, mainly because she would do whatever I wanted, including fulfilling my fetish by dressing up in lingerie and heels every...Read On

11

The Pool Man

I fucked the pool man

It had been several months since I moved away from the big city. It was hard moving to a city with not a lot of people I could hang out with or be with. I had become really good at dressing up and having anal sex, but was becoming more and more restless of not having a regular, daily thing with someone.  I began fantasizing about being with the pool man. He was always friendly when he came...Read On

11

My First Experience With A Man

My first experience with a man and he made me crossdress

It happen when I was 18 years old. I was working for a clothing company at the time and it was a slow Tuesday morning. As I was folding clothes, a tall (I’m 5’5 he was 6’2) light skinned black man approached me. He introduced himself as Sam. He looked like he was well into his forties but was really fit. He inquire about several clothing articles in our store and slowly the conversation...Read On