Gay Crossdressing Stories

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Infinite Scroll

Three-Way Banter

by MoronTheDivine on Sep 1, 2017
Group Sex

I don't know if you could call what the two of us were doing dancing, as much as just that drunken bumping and grinding that dancing eventually gets reduced to. Either way, I was enjoying the hell out of myself. I wasn't really that drunk, but alcohol, in my mind, always gives me a justification to be brash with people. Generally I'd be too shy to dance, or...

Catching Up

by RedHairedandFriendly on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: The following story is based on a fantasy that a Litster posted on the Fetish and Sexuality Central Forum. I spoke with the Litster, gained permission from them to write the story, as well as discovered they would enjoy reading it in 1st POV. I told them I would try writing it in 1st/3rd person POV – if that's the right way to say it? I do ho...

Donkey Boy William Ch. 08

by heavenlyKK on Sep 25, 2017
Exhibitionist & Voyeur

Jane came out of the bathroom clad in a white bra and yellow, patterned panties. "Come on, let's go," she said, looking into the mirror, applying the final touches to her hair. William stirred, but didn't move. "Come on, time to get up." Jane went over to the bed and threw the blanket off of him. "Holy cow, you are up...Woodie-alert!" William smiled. "How...

How I Met My Wife

by Godscountry on Sep 13, 2017
Transsexuals & Crossdressers

When they ask, I tell people that I met my wife on the internet. I'm sure they assume it was on a dating site. But the full story is much more interesting, how she came to own me and how I came to worship her as my wife. I'd been single off-and-on for a long time. 28 years old. I had a decent job in engineering. I've had a few good girl friends, but nothin...

Cleveland Dreams

by Dreamer971 on Sep 13, 2017
Erotic Couplings

Earlier this year I had to travel to Cleveland for a business trip that would last a few days and straddle a weekend. My wife was excited because her best friend Penny lives there; she immediately had visions of us both spending the weekend partying with her. Our daughter's schedule intervened, however, and kept her from joining me. She said that I should st...

21st Century Subterranean Slavery Pt. 08

by Reavantwo on Sep 13, 2017
BDSM

Back in the lineup One-eight-six felt wild and untamed on her first day back in the lineup. She deliberately stumbled within the chain gang next to the board walk. She stopped now and then defiantly yanking the chain in front of her, forcing the slave behind her to crash into her back. When the guard lashed her she spat in her face leading to more lashes. B...

Secret Lover Ch. 02

by samsfantasy on Sep 25, 2017
Transsexuals & Crossdressers

The next morning I woke up. As my eyes adjusted to the light, and my brain took it's time recognizing where I was, it began to think about last night. I remember Colleen kneeling on the floor in front of me, her tits covered in my cum and smiling, saying "this changes everything." I turned my head, there she was, still sleeping, still looking hot, and makin...

Keep It In The Family Ch. 02

by Amandawilliams on Sep 14, 2017
Erotic Couplings

I had fucked Peter some fifteen years ago and now I had just fucked his son, also named Peter. Both had been doing building work for me, the elder when I was married and the younger now I was divorced. The father and I did it when I was living in a large rambling house in Chigwell, just outside London in Essex. With the son it was at was at my duplex apartme...

A Nhyte with Rhona

by Darlantan on Sep 26, 2017
Celebrities & Fan Fiction

Author's note: I know it may be politically incorrect to refer to a female actress as an actress, and that such distinctions may be deemed wrong, but it's my story, and I'll be politically incorrect if I want to. I'm making a stand against the over-regimentation of our world, and something like Literotica should be simple and straight, at least that's what I...

James: Mr. Nude International Pt. 05

by doubledigit on Sep 13, 2017
Exhibitionist & Voyeur

The day broke sunny and warm. It was a perfect day for getting naked and strutting one's stuff for the wealthy and mostly middle-aged patrons who were gathered to attend the breast cancer awareness fundraiser. The presumption was that the ladies would be titillated enough by the sight of the well-endowed males to open up their checkbooks and make a sizeable...