Gay Lingerie Stories

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My Sexual Story Ch. 01

by bisexual_slut on Sep 14, 2017
Erotic Couplings

This is a true story; only the names have been changed to protect everyone's privacy. I am in my late 30's, of slight build almost girlish type body with an 8.5-inch cock between my legs and it is almost as thick as my wrist. I am writing this as I recently confessed to my wife of my sexual activities but as she is not all that open-minded does not want to t...

Caught in a New Life Pt. 01

by Fibaro on Apr 20, 2020
Transgender & Crossdressers

(Hello everyone, this is a story that has been written for a very special reader of mine.) Intro Monroe Smith had everything pretty well figured out for himself. He was 43, his hair was brown and slightly greying, but his hairline hadn't really receded thanks to the hair implants he had done about a year back. He had never been a big guy when it came to mu...

Sissy's First Trip Out

by thinksissy on Dec 24, 2019
Transgender & Crossdressers

*This is my first story so please comment as much as possible to let me know what you think. Thank you!* Kenny had always been obsessed with women's underwear. It all started out pretty innocently, well, as innocently as can be expected when masturbation is involved. He used to look through women's fashion catalogues and drool over the lingerie and bikini s...

Shattered

by kayla_femboi on Sep 16, 2017
Transsexuals & Crossdressers

The following story is mostly true. I changed the names for the sake of privacy and maybe spiced up the details a bit. A little background about me: my name is Brian, although when dressed i feminize me name to Brianna. I was a closet crossdressing sissy. I had always been effeminate growing up and a bit confused sexually. I never really dated girls. Inst...

Katie's Exploits Ch. 01

by swingingpuss on Sep 16, 2017
First Time

When I saw him for the first time my breath had caught in my throat and my heart had palpitated. Sitting amongst the other professors he looked like a cat among pigeons. His 6'2 frame emanated raw sexual power and as he seemed to be teasing a blushing older female professor his sea green eyes crinkled merrily and deep grooves in his lean cheeks had dimples p...

New Beginnings

by Sunnyskies on Sep 12, 2017
BDSM

Erica was 26, overachieving, well-educated, and beautiful. She worked in the finance department of a very successful and profitable fortune 500 company. Erica had quickly earned the respect of others in the industry and was rewarded well with promotions and bonuses in the five short years of her career. She had every reason to be thrilled and excited about t...

Under the Gaze of the Sirens 02: Unknown Desires

by jakladd on Dec 2, 2019
Transgender & Crossdressers

We were in Minneapolis for a conference, 3 nights Tuesday through Thursday, leaving Friday morning. Our firm was a top producer of components for fiber optic technologies. Flew in from Orlando, got settled in the hotel, then on to registration and a meeting in the afternoon, dinner with a few co-workers from around the country. Ran into Warren from the main...

Goodbye Sis, Hello Bro

by Deborah on Sep 16, 2017
Humor & Satire

("Goodbye Sis, Hello Bro” is yet another true episode in the sexual story of my life. I am purging my soul. Telling of my past "sins" is part of my repentance.) "Goodbye Earl" by the Dixie Chicks made it big at the Country Music Awards. "Goodbye Sis" is my favorite tune. Kevin and I met online. We both frequented a certain erotic bulletin board. Soon frien...

Caught Wearing Panties

by pantyhigh on Aug 13, 2019
Transgender & Crossdressers

I often wear panties under my shorts when I go fishing. Today I was wearing some pink lacy panties and I had a pink lacy bra on as well. Just walking or standing around no-one could tell I was wearing them but when I bent over to take a fish off the line my panties might show if my shirt were to ride up a little and I think my bra line would show through the...

Becoming Jessica

by Lovely_Jessica on Sep 25, 2017
Transsexuals & Crossdressers

It all started after I told Emma I no longer wanted to have children one day after work on a Friday evening. Over the past few months we were actively trying to procreate after 5 years of marriage. We originally never wanted children, but that apparently changed after her proverbial "baby clock" starting ticking. Don't get me wrong the sex was great and we w...