Cross Dress Stories

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Halloween Cross-Dressing Bash Ch. 06

by BOSTONFICTIONWRITER on Sep 14, 2017
Transsexuals & Crossdressers

Gloria left the store in the capable hands of her store manager, Sharon. After paying for his purchases, with Gloria giving Bob a very generous and unexpected 20% discount, Bob followed her car home in his pickup truck. He was just as excited to maybe have a sexual affair with her as he was with the thoughts of trying on the clothes he just bought. They sto...

Do You Know A Cross-dresser? Ch. 02

by BOSTONFICTIONWRITER on Sep 13, 2017
Reviews & Essays

Do you know a cross-dresser? I bet you do only you'd never know it. I ran into my friend Stuart over the holidays. I haven't seen him since I saw him in Marshall's clothing store last winter when he was dressed as a woman, albeit a super sized woman. He was a bit cold to me and I don't blame him. We had a polite conversation asking after our wives and kids...

Hot Sex Instead of Dancing Ch. 12

by SusanJillParker on Sep 12, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Wanting to look pretty, Walter has the uncontrollable urge to dress as a woman again. Sunday, the day of rest, Walter reflected over all that happened during the weekend. Linda had hot sex with his three friends, Jim, Henry, and Tom. Tiffany abandoned wearing her sexy nightgown to clean her kitchen in her even mo...

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...

Changes Ch. 02

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

Notes to Reader: (1) A lot of this is fiction; much is fact. (2) Cross dressing in marriage is a difficult situation; acceptance of it comprises three entities: husband, wife, couple. (3) Nobody CHOOSES to be a cross dresser, so please don't demean yourself (the reader) by macho dismissal and criticism. Lawyers, plumbers, truckers: anyone can be one. Most...

Using Halloween to Dress as a Queen

by andtheend on Sep 19, 2017
Transsexuals & Crossdressers

A time to wear a costume, Jerry uses Halloween as his excuse to dress as a woman. Jerry loved October, his favorite month of the year, by far. The Fall was his favorite season, too. With the colorful array of leaves that crunched underfoot and the multi-colored canopy overhead, he loved the cool crisp air that made his nipples as hard as his cock. Whenever...

Celebrating National Nude Day Ch. 06

by BOSTONFICTIONWRITER on Sep 15, 2017
Transsexuals & Crossdressers

"Okay, who's next? Who celebrated National Nude Day with this contest in mind? Who wants to share their story with the group? Is there anyone else with a story before we close the competition and take a vote for the winner?" Everyone looked around to see who else had a story and who else had their hand raised. "Also, let's not forget the rules. You must be n...

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...

Do You Know A Cross-dresser?

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

Trans-genderism: Cross-dressing I never considered writing a story about cross-dressing until I was confronted with it. I just recently found out that a friend of mine who I have known for several years is a cross-dresser. He's a good guy, a family man, is married with kids, and, by all accounts, appears normal. Whatever that means? Yet, what is normal? Am...

Im Not Finished Yet

by HappyDom on May 2, 2018
BDSM

Jill and I had been invited to a condo at the beach to spend Saturday night with some new friends. Although we haven't known this couple long, we really hit it off with them. Each time we get together it feels so comfortable that it's like we have known each other for years. They are both very intelligent and the conversation is always fluid and interesting....