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Crossdressing

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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.

86

My night as my wife's sissy boy

My wife surprised me, and how! It Was a night I will never forget.

The last few weeks had been extremely busy and my wife and I had very little time to spend with one another.  We needed some alone time so we made arrangements for the kids to spend the night at their grandparents house.  My wife asked if I would mind dropping them off by myself as she had a few things she like to get ready while I was gone. As I pulled into the driveway I...Read On

78

My First Time in a Dress

How I Became a Crossdresser

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday....Read On

32

Caught

i was caught by my Hated(at the time) Step-father

I see all these girls with the first time or the first time they got caught dressing and it turns me on looking back and thinking of mine. Well I was young when I started getting into my moms and soon to be step sister’s clothes. My mother divorced my father when I was young but never really knew my dad do to the fact that he was always in the military and my mother was tired of moving...Read On

42

A Visit

Husband dresses up for his wife so that they can have a little fun during the weekend

My wife knew of my enjoyment to wear women’s lingerie when we married and over the months that followed our honeymoon she had often wanted to see more of me dressed up.   I always enjoyed these times although they were not as frequent as I would have liked them to be. One Friday, after a rather long and difficult week at work, I returned home and was greeted by a tender hug and a loving...Read On

31

First time with a man

I have been crossdressing since the age of 11 years old. I never really considered myself anything other than straight. Up until I turned 19. I often fantasized about other guys when I was dressed but that's as far as I took it. The year was 1984 and one day I decided to stay home from work to play. I get dressed up in a pair of purple satin string bikini panties,matching bra,black...Read On

42
Audio version available

Panty Slut

Caught wearing my panties, he soon gets a taste of his own medicine

You little bitch! I can’t believe you're wearing my panties again. Do you want to be a girl? Do you? Well that bulge in your panties tells me you're lying. Come on in here Jennifer. That’s right, I told Jennifer all about you jerking off in my lingerie. I don’t think she believed me. Stay right there so Jenn can see what a little sissy you are. Isn’t he...Read On

64
Audio version available

In My Panties!!!

Sarah discovers Larry's secret.

Larry and Sarah were your typical yuppie couple working two professional careers. Larry a techno wiz was the research and development department head at a local manufacturer while Sarah was the office manager at a local Saturn car dealership. Their weekends off work were filled with their hobbies of camping and outdoor fun. Both loved nature and enjoyed their time together on beaches and in...Read On

32

A great experience as a crossdresser

Glorious glory hole session

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie. I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie. One of my...Read On

51

Little Black Dress

The events were all the result of a lost bet.

I pulled in the driveway, and saw that my wife was already home. My thought was that she’s home early. I unlocked the door and went in. A few feet inside the door was my work stool with a box on it with a note taped to the top. I opened it and started to read. Hun, I’ve decided that tonight is the night I want to collect on our bet. You are to follow...Read On

36

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

23

My first halloween night as a teen CD!

My first time i dressed up like a chick and how lucky i got that whole night

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I...Read On

28

Caught dressed like a sissy slut

My girlfriend was away for the weekend so I had the place to myself. I was feeling incredibly horny so I went through her knicker drawer and decided to dress up (which I've enjoyed many times before). I put on a really tight, pink thong, black fishnet stockings and suspenders, and her black mini skirt. I looked at myself in our full-length mirrored wardrobes. God, I looked so sexy and...Read On

23

With the wifes help

wife takes me for my first gangbang

Last night I finally lived a long time dream of mine. My wife Melody of three years came home from work around 7pm and told me to follow her upstairs. Once we arrived in the bedroom, she laid back on the bed and spread her legs wide for me. She was dressed in a long white light cotton dress with a floral print and a belt cinched at the waist. The dress fell long enough to conceal most of...Read On

41

The Party

It happened one halloween

I am a closet cd. It was Halloween. My wife called from work and said she wanted to go to a party at a friends house. It was a costume party. She said she had a costume and I was to wear one as well. What, I don’t have one. Yes you do, your going as a girl. But I’ve never done this. Well you’re going to tonight. No one will care because it’s a costume party so get dressed...Read On

21

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

8

me and my boyfriend

my day with my boyfriend

hi yesterday my boy friend came to my house when i was alone and he had brought a pair of pink salwar kameez and a red silk saree with matching lingerie. when he arrived at home i was very happy as we both were alone for whole night at my house when he came i had just come out of bathroom after having a shower when i was taking my underwear to wear he stopped me and handed the panty he...Read On

62

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that would be perfect. I really wanted...Read On

46

A Taste of my Girlfriend's Dildo

I'm caught - and made to love it.

I can’t think of anything I’d rather be doing than sneaking into my girlfriend’s wardrobe while she’s out and trying on her lingerie. The moment she leaves the house, I head for her garter belts, bras and knickers. I don’t have anything to put into her 36C bra cups, and my cock barely fits her panties but all that silk, satin and lace is irresistibly sissy and feminine. On the day...Read On

32

Mom's Boyfriend

Once mom and dad's divorce was final I moved back in with mom into our house. Dad had purchased a townhouse a few miles down the road. Being 17 and staying with my aunt and uncle had given me the freedom to do and act as I pleased, so I made no bones about telling mom that her son was a crossdresser and enjoyed sex with men. She really didn't say much and pretty much told me that as long as I...Read On

36

Dressed Up and Used

Young Crossdresser gets Fucked again

     This is a continuation of my first story "MY First Time in a Dress".  I love reading your comments, enjoy!      I avoided Dan for the next few days by playing sick.  I was not ready to go over to his house again yet.  My ass was so sore the next day I had to have some relief.  I was still having a hard time comprehending what really happened.      I finally went to his house...Read On

6

A Maid Story

Paul lives out his maid fantasy

It had been a long day and Paul was tired.   After a week of traveling and a full day of meetings, Paul was ready to unwind with his wife, Marie.   They were what many people might describe as soul-mates. They were best friends who shared their deepest, darkest secrets with one another and who regularly consulted with one another on a wide variety of topics. Their love life had...Read On

46

The Panty Princess

Dominant girlfriend discovers her love for submissive boyfriend

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. ...Read On

33

I become my wife's girlfriend. The beginning.

My name is Tony and I'm a regular straight guy. This is the story about my life as the part of lesbian couple, and yes, I'm aware of weirdness of this statement. During the first period of our relationship our sex life was fantastic, a man's dream. At this time I wasn't aware of my dark fantasies, our sex was very good and I thought of us as a very nice couple. And then, something like...Read On

8

Caught and the Consequences

Husband caught dressing and the wife's retribution

‘What the hell do you think you are’   I just lay there not knowing what to say and I am sure going very red under my make up.   ………..   I will go back many years and start at an earlier age.   For as long as I can remember I have cross dressed, always in private, without my partners or girlfriends knowing, totally in the closet,...Read On

35

Chrissy's First Black Cock

Chrissy gets fucked by a big black cock for the first time

  After I awoke from a deep slumber of a much needed nap, I laid there recounting memories from the night before with Todd. I got out of bed, walked to the kitchen and grabbed a soda from the fridge before sitting down on the sofa. As I sat down, a pain rippled through my ass, reminding me of the brutal fucking I had received from Todd. I sat there smoking a...Read On

10

First Time Dressing

Helping a friend find his inner female

A few weeks ago my gay friend Paul phoned and asked if I would go out with him on Friday night. My husband John and I have known Paul for ages and we knew he was getting over breaking up with his long term boyfriend so I happily agreed. John stayed until Paul came round so we could all have a drink together and then he went off with a couple of his mates. After John left we had some more wine...Read On

20

Caught in a Prom Dress

I Should of Listened to What my G/F Said!!!!

If you can remember the stories LUCK RAN OUT AND I GOT CAUGHT then good this has escalated from there if not please read it first. It was a few weeks before my G/f college prom and said had her prom dress all prepared and hung up in the spare bedroom where i stayed. (her folks where very strict) As you can probably guess by now i wanted to try it on, it was a gorgeous gold long dress...Read On

31

I become my wife's girlfriend. Part II.

This day at work was unusually tedious and seemed like it was never going to end. At the beginning I occasionally dropped my boss's cup and the coffee poured on floor, but luckily the cup survived. After this some guy stepped on my toe and caused me much pain, I bent to touch it and suddenly had a feeling like my butthole was cut by the string of thong. Later my boss was very angry all the day,...Read On

7

Keep Silent or Be Caught

Remember be silent or be caught!! Last year my girlfriend got asked to be a bridesmaid. She of course sed yes, this ment she would have to have a bridesmaid dress. Now all cross-dresser has a dream of wearing a wedding or bridesmaids dress and i couldn't wait for her to get it and try it on. The dress was a gorgeous white satin dress from Bhs. The top was strap-less and had a...Read On

22

Dad Catches Me With His Friend

From an early age like most I started to get a desire to wear womens clothing. I would always take my mom's thing's and put them on and masturbate in them. The feeling was nothing like I have ever felt before. Around the age of 16 I had gotten a job and started buying my own things,lingerie and such with the money I earned from the job. Prior to that,around the age of 13 my mom had left...Read On