Cross Dressing Stories

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A Little Help for a Friend Pt. 02

by DrLit on Sep 15, 2017
Fetish

If you read my story, A Little Help for a Friend, you realize my wife and I used a three way to help a friend get back to having sex again after a tragedy. That friend, Julie, wanted to take us to Key West on a wild sexual adventure. All I needed to do was two expensive bikes for her; one a very expensive carbon fiber triathlon bike and the other nice road b...

Cindy's Makeover

by CindyUSA on Sep 16, 2017
Transsexuals & Crossdressers

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only started dressing five years ago. Many cross-dre...

Black Sissy For White Goddess

by Samuelx on Sep 16, 2017
Interracial Love

Finally, I feel like I am where I belong. Picture this, if you will. A big and tall, muscular Black man clad in a pink tutu and frilly White panties, my face fully made up and my lips properly rouged. I am kneeling before a six-foot-tall, slender red-haired White chick and sucking her strap-on dildo. My Mistress Amelia Heinrich smiles at me as I suck her dil...

Something Had To Change

by sublocked on Sep 16, 2017
Transsexuals & Crossdressers

This was not going the way Diane had thought it would or should. Basically nothing, and yet everything, had changed in their marriage in the last six months. She watched him now, sitting on the sofa, drinking a beer, unshaven, and between picking his nose and scratching his ass, she wasn't sure what his biggest pleasure was. At least he was fit. There was...

Freddie Becomes a Cross-Dresser Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

Now, that I bought everything that I needed to transform myself from a handsome and modest man to a beautiful and sexy woman, I realized that I had completed the easy part in buying the clothes, the makeup, and the perfume. The difficult part, of course, would be dressing up like a woman without having a woman there to help me. I certainly did not want to as...

Hot Sex Instead of Dancing Ch. 02

by SusanJillParker on Sep 12, 2017
Toys & Masturbation

Please give me the support of your vote. * Walter masturbates himself while watching his shapely neighbor cleaning her kitchen in her sexy nightgown. Bill worked long hours as a desk sergeant and wasn't always home to care for such a beautiful woman. As far as Walter was concerned, if Tiffany was his wife, he'd never leave her side but realistically, he'd...

High Heels and Stockings Tryout

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

High Heels and Stockings - First Time I blame Literotica, or credit it, as the case may be. I've always been excited by women's sex clothes -- high heels, stockings, panties, and skirts, and have shot lots of loads fantasying about how hot women look all dolled up. Then I came across Literotica, and started reading all the nasty, filthy stories about cross...

Halloween Cross-Dressing Bash Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

"If I knew you a bit better, I'd tell you the other half of the story relating to the name of the shop and what my ex-husband tricked me to do, but it's a bit risqué and I'm embarrassed that I fell for it," she said with a sexy laugh. "I'm too trusting and it's only something that I would do. I should have known better," she said hanging his dress back on th...

Halloween Cross-Dressing Bash Ch. 08

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

She looked down and saw that he had an erection. "All you guys are the same," she said shooting him a cold stare. "Here I am pouring out my heart to you about what my ex-husband did to me and you have an erection." "Sorry." "Do you realize how humiliated I am to find out that I blew every man in my community? Then, to find out that I blew my husband's fo...

Dressing Up For My Wife

by dirtyjoe69 on Sep 13, 2017
Transsexuals & Crossdressers

My wife and I had a bet on the football game that pitted our two rival teams against each other. It was a horrendous day for my team and hers slaughtered mine 31-0. It was the same bet we always have with each other. It is a bet where no one really loses because it ends up with us having wild kinky sex. On earlier bets we have had, she has had to let me fuc...