Cross Dressing Stories

72,522 results
Orientation
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Infinite Scroll

Men's Sexual Confessions: The Group

by PositiveThinker on Sep 15, 2017
Loving Wives

Best Buddies Sexual Peccadilloes A group of men and women sit around talking candidly about their sex lives. I'm Paul, the host of this party. Thanks for stopping by to read my story. We were all sitting around the big screen plasma TV watching the Super Bowl one year. I had invited all of my best buddies to watch the game with me. There were 21 of us guy...

Dressing for Larry and Friends

by loneguy01 on Jul 17, 2018
Transsexuals & Crossdressers

After an encounter with Larry, he suggested that I might like cross-dressing for a future date. That was something I had never considered. Although I am pretty much a total bottom when it comes to gay sex, I wasn't particularly femme nor had this ever occurred to me. However, Larry's suggestion excited me and I tried it and liked it very much. "Dressing for...

MaidSally Episode 02

by cd2the9s on Sep 16, 2017
Transsexuals & Crossdressers

As I explained in my first episode, I am a kept Cross dressing Maid-servant for my Master who I also refer to Mr. G. (or G). My Master provides for me and makes my life comfortable. For this, I provide him with a willing and compliant servant. Master keeps me quite busy with daily chores and things and he uses me as he wishes. Sometimes he lets others use me...

How I Became Victoria

by Vicktoria2 on Sep 16, 2017
Transsexuals & Crossdressers

This story is pure fiction but you never know do you. How I became Victoria I began cross-dressing early but didn't fully dress until I met a nice gentleman at a gay bar. He was in the movie industry and thought I would indeed make a pretty lady and would teach me how to please men. He provisioned me with lovely outfits and a friend of his taught me makeup...

First Time Dressing Up

by CaramelBlack on Feb 7, 2018
Transsexuals & Crossdressers

I've never had a fetish for female clothing, but I did feel extremely sexy when I first had the opportunity to luxuriate in it at home alone. I began dressing as a girl at 12, but it wasn't until I was 18 when I dressed up completely for the first time. When my parents went away for the weekend to Atlantic City, I took advantage of the opportunity to explore...

For My Little One Ch. 1

by mj3168 on Sep 17, 2017
BDSM

We had gone shopping some more. We were in mall, showing off and teasing each other (and those around us) in public. This time, in the lingerie store things had heated up a bit more. This time, when you asked the sales girl to help you with the clasp, you reached out and ran your hands along her hips and onto her tight little ass. You pulled her body tight t...

Hot Sex Instead of Dancing Ch. 08

by SusanJillParker on Sep 12, 2017
BDSM

Please give me the support of your vote. * Bound to the bed and blindfolded, instead of taking her dancing, Walter gives his wife, Linda, what she really wants, hot sex. With her on her back naked and helpless, Walter imagined his wife, Linda, tied to the bedposts at her wrists and ankles. In the way she was staring at him was the same way he imagined him...

Neighbors Delight Ch. 02

by gummidurango60 on Dec 25, 2018
Transgender & Crossdressers

My emotions were full throttle after my session with Aaron; after a few beers he broke me down, fucked me, and now wants to take me out on a date. My problem is I've never been out in public let alone on a date with a man... nor do I have the wardrobe to support it. I entered the code and opened the secret compartment inside of my closet. Looking through...

You Can Always Say No Ch. 01

by AngelCherysse on Sep 25, 2017
Fetish

I have always considered myself a liberated woman. Rising through the business ranks to become a Vice-President at a major media consulting agency was just one of many goals I set, then met. I don't see any conflict between that and being a 'girly-girl'. I'm not ashamed to admit; I have used my raven-haired beauty and generous natural charms to advance my ca...

The Making of a White Sissy Slut

by AfroerotiK on Sep 18, 2017
Transsexuals & Crossdressers

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by sayi...