Gay Lingerie Stories

45,061 results
Orientation
Length
Source
Infinite Scroll

Broken In by BBC

by sissyashley4bbc on Jan 15, 2019
Transgender & Crossdressers

My wife, Jena, and I married so young, right out of high school so we were still only 22 when we had our 5 year anniversary earlier this year. Things had gotten a bit stale in the bedroom. We are both very open sexually, but we just found ourselves in a bit of a slump. So open to the extent that we had even tried some threesomes previously, both with an ex...

Innocence Ch. 01

by gummidurango60 on Oct 24, 2018
Transgender & Crossdressers

Graduation Party Today, as I sit in the crowd of my fellow classmate waiting to receive my high school diploma my mind begins to drift until my row stands breaking my concentration. I follow the girl in front of me stopping on the side of the stage. One by one my classmates get called by name and walk onto the stage to receive their diploma. Fortunately,...

Sissy's First Time

by Sonjas_pet on May 23, 2018
First Time

By the time my wife, S, and I had been married for fifteen years, there was not much that we didn't know about each other. If you're going to make it that long, you're going to have to learn to be honest with each other. This is what had led to me recently, cautiously, come out to her as being bi, turning at once tepid physical relationship into one of ongoi...

How I Became a Whore

by cutemorri on Sep 14, 2017
Transsexuals & Crossdressers

Totally true story. I hope you enjoy! * So I had always had this fantasy of selling my body for a man's sexual pleasure. To me there is something validating about the fact me dressed in woman's clothes, lingerie, and acting girly could be attractive and sexy enough for a man that he would be willing to pay me to suck his cock and let him slide it inside...

The Chocolate Room

by johnnieblue44 on Sep 13, 2017
Erotic Couplings

Their eyes met as he walked toward her door, where she stood. They had not seen each other for over 18 months, and at that moment, he remembered just how beautiful and stunningly sensuous she was....the flashbacks began.....his sense of recall became vivid..... He recalled how she once had a gay co-worker tell her that he would consider going straight for h...

Bisexual Black Stud

by Samuelx on Sep 16, 2017
Interracial Love

Marisol Ryan is at it again. The gal just can't seem to keep sex off her brain. This five-foot-eleven, blonde-haired, green-eyed, alabaster-skinned Irishwoman is a sexual dynamo. Currently, she's lying in bed, fingering herself while watching her boyfriend Hector Brown as he slept in their bed. He had come late, and she hadn't known where he was. She'd been...

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

Raymond My First Man Pt. 01

by JoannePare on Sep 16, 2017
Transsexuals & Crossdressers

I work from home and I am a transvestite, it is wonderful to be able to dress as I want and just enjoy life and my work as Joanne. The other day I did something I had never done before and it was so astonishing. I would often rent hotel rooms to dress and spend the night as Joanne and enjoy myself. One such night, a Monday, I was at a hotel and I felt lonel...

The Retirement Party

by DrLuverotica on Sep 18, 2017
Transsexuals & Crossdressers

April 3 Jo had been singing it for days and it was driving me mad! "It's all about the bass, about the bass..." On and on she went until finally I screamed: "Enough already!" "Oh hubby. Do you not like my song?" "Well, I like the way you move to the song." Jo looked hot swinging her big sexy curvaceous ass in a short micro skirt and flicking it up occasi...

Stuck at Home Ch. 02

by grgy56 on Jun 8, 2020
Transgender & Crossdressers

Stuck at Home Ch 2 "Uh... Laura?" I looked back at my girlfriend. I stood there in my bra, panties, stocking and garters and looked for some sort of response or reaction from being found out. I had two outstanding items jutting from me: my hard five and a half inch, uncut erection and my big breast forms. Laura continued to just survey me up and down. I s...