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cuckoldmalesub
vanessagrrl
ThePhantom
CAPITALLETTERJ

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.

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1936Storyguy

First Meeting with a CD

A cross dresser experiences his dreams with a man

It was strange, he contacted me first and his profile stated he was looking for a domme or trans to submit to. I guess the hidden desire to please a man won out. We communicated through mail and messenger for months. We even met for coffee and some groping, where I tested his desire for nipple play, some severe pinching and even squeezed his sac to express the control I wanted and what he...Read On

Added: 18 May 2013 | Category: Crossdressing | Avg Score: 0 | Tags: cross dressing  sm  anal  first time  

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CAPITALLETTERJ

Dirty Little Me

Caught, with panties on and my pants down...

Rushing around all day, it seemed like this was starting become a ritual for my Fridays but this particular Friday I would never forget!  Waking up late as usual I flew out the the door as fast as I could, not giving any thought to what I had done the night before. As usual my boss wasn't too pleased but I never really minded his attitude because everything he lacked in personality he made...Read On

Added: 15 May 2013 | Category: Crossdressing | Avg Score: 4.59 | Tags: gym  locker room  older  panties   | 4 Comments

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vanessagrrl

A New Level

Things escalate for Vanessa and her man

Greg and I had been seeing each other for a little while at this point, and things were going great. We had gone on a few dates and I loved how he always treated me like a lady. He made me feel so sweet, sexy, and vulnerable. Tonight was four months since our first night together and I wanted to surprise him with something a little special. I bought a long coat, and I thought it would be fun...Read On

Added: 13 May 2013 | Category: Crossdressing | Avg Score: 4.43 | Tags: crossdressing  buttplug  anal  oral  hormones   | 4 Comments

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cuckoldmalesub

Caught, Used and Loving it Part 2

My descent continues

It had been two weeks since I had been caught and used by the mystery woman and her boyfriend. They had left as quietly as they came, and I was left kneeling on the floor dressed in all my best female clothing, cum dripping off my face, and my own cock dribbling cum on the floor. Since then, I had had only two emails. One was sent immediately after they had left and contained ten pictures...Read On

Added: 10 May 2013 | Category: Crossdressing | Avg Score: 4.93 | Tags: femdom  crossdressing  forced  oral  whore   | 7 Comments

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ThePhantom

My First Time - Part 2, or The Beginning

Once was not enough

It was about two weeks after Halloween that the dreams began. I began to dream about being transformed again. I was able to recall the feel of the silky garment against my skin, the sensation of the nylons brushing against each other as I walked. I recalled all the women at the party who danced with me and rubbed my silk covered ass. "You feel like a real girl," more than one said, and I...Read On

Added: 08 May 2013 | Category: Crossdressing | Avg Score: 4.5 | Tags: nightgown  nylons  thong  heels   | 5 Comments

14
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vanessagrrl

A Great Date

A first date that I hoped might lead to a first steady boyfriend

I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me. It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you....Read On

Added: 05 May 2013 | Category: Crossdressing | Avg Score: 4.79 | Tags: crossdressing  anal  oral   | 7 Comments

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ThePhantom

My First Time

A true Halloween cross-dressing story

I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks. If you parked your yacht and paid the docking...Read On

Added: 30 Apr 2013 | Category: Crossdressing | Avg Score: 4.69 | Tags: halloween  nylons  garter  miniskirt   | 4 Comments

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CourtneyFux

Hitch-hiking Baby Doll: Part Two

Being a sexy girlyboy for a trucker stud leads to lots of sexy pleasures.

I woke my trucker stud up in the middle of the night by sucking on his cock and making it hard for him. When I had him good and hard, I climbed back up between his legs and let him put it in me again. His cock was nice and big and my ass was good and tight. It felt good to feel like a girl receiving anal from her big Daddy. While we lay on our sides in his bunk and fucked, my trucker...Read On

Added: 16 Apr 2013 | Category: Crossdressing | Avg Score: 4.85 | Tags: crossdressing  oral  anal  bisexual  spanking   | 7 Comments

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CourtneyFux

Hitch-hiking Baby Doll: Part One

Hitching a ride with a trucker leads to loads of fun for this sexy little tranny boy.

I hadn't been in his cab for more than a half hour when the driver who picked me up, brought up the subject of sex to me. "Last week, I had a guy and girl riding with me and they both liked giving me blow jobs. And, you know, if I closed my eyes, I couldn't tell the difference of which one was sucking me off. They were both excellent at sucking cock." "That sounds like you had a fun ride,"...Read On

Added: 14 Apr 2013 | Category: Crossdressing | Avg Score: 4.8 | Tags: crossdressing  oral sex   | 6 Comments

15
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CourtneyFux

A Picnic in the Park

Wearing my sexy thong bikini to the park leads to hot action with a big stud.

It was a beautiful spring day, the kind of day a girl starts to think about wearing her new bikini to show off her hot body for lots of men. I was feeling frisky and thought meeting some new men would be fun. There was a county park near my town where lots of men go to meet up for some good blowjobs and hot encounters. I planned to go there today. My new bikini still had the tags on it and...Read On

Added: 10 Apr 2013 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing  oral sex  anal  exhibitionism  bisexual  voyeur  spanking   | 5 Comments

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kyliekained

In Her Shoes Part 3

This is the final part so please read both other parts to this story to understand it fully.

I guided Peter into the main shopping mall in town leading him straight into a shoe shop. The girl in the shop fetched a few pairs for me to try on and I relished asking Peters opinion. He tried not to look too obvious that he was hooked on my shoes and feet. I 'hummed' and 'ahmmed' a short while, telling the girl I was undecided and may well be back later. Grabbing his arm once more we...Read On

Added: 04 Apr 2013 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  fetish  foot  shoe worship  first time  dominant  submissive   | 5 Comments

28
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cumonmybum

My First Time With A Hot Sensual Lady - With A Lovely Cock

A shy bi guy has his first amazing encounter with a beautiful lady who also has a beautiful cock

Although I'd never been with a man before, my online chats and contacts usually ended up being with men - they seemed to be so much more horny and available than women. Either I was doing something wrong or women weren't into online sex all that much! Anyway, for years it's always been a hobby, an indulgence if you like, never turning into real contact, just a fantasy that I look forward...Read On

Added: 01 Apr 2013 | Category: Crossdressing | Avg Score: 4.65 | Tags: oral  cum  transvestite  erotic  lingerie  first time   | 9 Comments

26
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VelvetC

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

Added: 29 Mar 2013 | Category: Crossdressing | Avg Score: 4.88 | Tags: crossdressing  mature  seduction  bi-sexual     | 6 Comments

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VelvetC

Mariah... My Wank Mistress

How I met Mariah, a crossdresser's dream...

We first made contact about three years ago, on one of those dirty dating sites. I was showing my tranny profile, Velvet, at the time, and was being hit on by a bunch of dirty old men, when this "Mariah" person said, "Hi." I was in a pretty sarcastic mood at the time, and was slightly peed off, as the guys I had been chatting to were only interested in one thing, getting their rocks-off. ...Read On

Added: 27 Mar 2013 | Category: Crossdressing | Avg Score: 4.94 | Tags: crossdressing  masturbation  milf  oral  mistress  humour  bdsm   | 5 Comments

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kyliekained

The Night Of A Thousand Dreams

I hope you enjoy

There was a few odd looking drugs laying on the side from a party. Being bored I decided to see what they were all about, I had dabbled before but had no idea what they all were. I had seen someone use a bottle with an inhaler on it, one good slug later I felt good. I looked through my wardrobe and decided that all guys seem to go for the more cute look in a girl. As I was feeling daring...Read On

Added: 21 Mar 2013 | Category: Crossdressing | Avg Score: 3.57 | Tags: crossdressing  drugs  spanking  fisting  weird   | 6 Comments

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