Gay Sissy Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

Girls Like Girls

by TransPunkPrincess on Oct 31, 2018
Transgender & Crossdressers

"I'm not coming out," Lisa called from within the bathroom. Mary rapped on the door again. "Come on," she cooed, "you can come out, babe. I wanna look at my wife." "No, you don't. I look ridiculous. I look like a clown, I look like an awful clock. I'm not coming out." "Baby, you're beautiful, I promise. Come on out and let me look at you." There was a lo...

Wife Controls My First Bi Experience

by Judge60 on Mar 26, 2019
Fetish

First, let me thank "HeyAll" who functioned as my "volunteer editor" on this story. His assistance was invaluable to the process and to the content itself. I thank you, sir! BACKGROUND: Approximately two weeks ago I placed a notice in the Literotica Personals. My "Profile" read as follows: "Introduction I am a 65-year-old man and have been straight my en...

New Year's Evolution

by PiperHamlin on Jan 16, 2019
Loving Wives

While I was working on a darker story for a different category at Lit, I hit a wall. Being stumped, yet still wanting to write, I switched gears and decided to write this. It's a flash story and late for the intended holiday, or it's early for the next year. ***** I like the holidays and I hate the holidays. Holidays in my world mean being around extende...

Bisexual Jamaican Manhood

by Samuelx on Dec 19, 2018
Group Sex

Jamaican men and Jamaican women are super opposed to bisexuality, gayness, lesbianism, and anything that's not rigidly straight. If you're gay, bisexual or lesbian, the island of Jamaica is definitely not the place for you. Whoever believes this pile of crock has obviously never met Sandrine Johnson, the Jamaican-born Canadian dominatrix who is making waves...

Jimmy

by ValoryG on Sep 9, 2019
Transgender & Crossdressers

When my husband brought up the idea, I was aghast. Here I was, six months pregnant, it was summertime in upstate New York (think heat and humidity), and our home on the edge of the woods had small rooms. Maybe the fact that we have two bedrooms (and no kids at the moment) gave him the liberty of coming up with his proposal. No, I’m not working, unless you...

Pretty in Pink

by jealouscuck on Oct 8, 2019
Fetish

I always remember thinking how bland men's underwear was compared to women's. In the animal kingdom, the male usually has the prettiest colors. Not so in people. I suppose traditionally, men's underwear is supposed to be functional while women's are fashionable. I was a late maturing kid. I was probably about two years behind some of my classmates. When I d...

Bimbo Beer - Girl's Night Out

by HllyOne on Aug 27, 2019
Transgender & Crossdressers

Juniper pressed her head to the bar's counter with the force of someone hoping to sink into it. "You know a good psychic? I need to work out which past life committed enough genocide to make karma feel the need to screw me over so hard." Mary looked down at her friend from the other side of the bar. "Oh come on, it wasn't that bad." "Really? What could be...

The Best Day of My Life Ch. 02

by HarleyLongshanks on Sep 21, 2020
Transgender & Crossdressers

So there I was laying on the floor of one of my fraternity brothers' rooms. In a dress and stockings. Handcuffed. Blindfolded. All willingly. Choking on the cum some guy who had entered the wrong room had shot down my throat after face fucking me for twenty minutes. I was briefly relieved when I heard the chains holding my arms outstretched were undone and...

Filthy Mail at San Quentin

by homerdepot on Nov 26, 2019
First Time

On the bus to San Quentin, Don was thinking about what went wrong. Here he was, an educated person with two engineering degrees and an MBA. He was going to prison. The judge was kind, and gave him only 16 months, but he still had to shutter his lucrative consulting business. And a felony doesn't look good on your resume. Don's felony was minor, and is not im...

The worst maid ever

by juanstalvern00982 on Nov 12, 2019
Fetish

This is a super-nasty fetish fic. Warning for all sorts of nasty shit ahead. Mud, food play, watersports, garbage play, all that good stuff. Don't keep reading if any of those things don't interest you. Its gonna happen regardless. * It had been luck that Elana got this posting. A friend from high school had mentioned that one of her friends saw the postin...