Gay Sissy Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

Counselling Changed Our Marriage Ch. 03

by Quietoldie on Dec 25, 2017
Transsexuals & Crossdressers

The fourth joint Interview Emily sits comfortably in the waiting room, texting and smiling. There is no question in my mind with whom my lovely wife is texting, nor much less any doubts about the lewd and obscene content of their texts. Emily looks totally ravishingly beautiful, dressed smartly in her business attire, her generous breasts bobbing up and do...

Mistress Melanie's Gay Bar Antics

by Spar on Sep 16, 2017
BDSM

The clothes pins on his nipples were killing him ... and he loved it. He'd come to learn, over about three months, that he was Mistress Melanie's Pain Slut. Often he wondered what it was he sought more: the pain; the humiliation; or Melanie's approval. She had the ability to expertly dole out a measure of each in a way that kept him coming back for more. Hel...

Glory Hole

by GateKeeper_A on Jun 11, 2014
Group Sex

Last month, you had discovered that your local adult novelty store had a glory hole. Since that day, that glory hole has been all you can think about. Every time you close your eyes, you picture a cock sliding through a hole towards you. Every time you masturbate, your mind is filled with fantasies of strange men's cocks. You shudder with a mixture of trepid...

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Superstars Rise and Superstars Fall Ch. 01

by felicia_rene on Oct 6, 2020
Transgender & Crossdressers

Superstars rise and superstars fall 1 Part 1 of 4 By Felicia Rene This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy the story Synopsis: The underlying theme is transformation and sexual punishment of the main character for his anti-gay womanizing feelings. For his heinous actions initially making h...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

The Cuckold is Black This Time

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

After months of hesitation and much soul-searching, a momentous decision finally got made. The big Black dude burst into Mistress Chocolate's den in downtown Ottawa, Ontario, and told her of his rather unusual request. The six-foot-tall, gorgeous Black Canadian female dominant listened to him, and then agreed to make his most forbidden fantasy come true. It...

Bambi Takes Over

by bambidoll1 on Jul 17, 2019
Transgender & Crossdressers

The morning sun crept around Darren's dark blue curtain, barely illuminating his apartment. On his bed lay a simpering little black sissy slut, covered in her own cum. Her eyes were closed but she was stirring—Bambi's sleep would be over soon. Her platinum blonde hair was a mess. Her bright pink lipstick was smeared. Her plump lips were heavy and her holes w...

A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

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It Happened in Mexico Ch. 03

by Angelscuck on Sep 16, 2017
BDSM

Angel watched the video of her husband in disbelief. Kelly had never shown any signs that he was gay before yet hear he was, begging to suck Joaquin's cock and to be fucked in the ass and looking like a sissy drag queen. It hurt her when her husband said he didn't want her anymore and called her a whore. She felt disgusted at the sight of him being fucked,...