Gay Lingerie Stories

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Jock Princess Ch. 03

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

I sat quietly in the office with Kate and sort of explained things. "I met a guy, I met this really pretty beautiful guy and I...I well thought that he'd make a good girlfriend...a sissy type." She looked at me. "Sissy?" "It's like a sort of trans thing and a gay thing it's a very submissive bottom thing." "You're into that?" I nod. "I am...was...am."...

Becumming Lisa

by Sweetlisatv on Sep 16, 2017
Transsexuals & Crossdressers

I have always known deep down that I am a transgender person, born a guy but never felt happy in my body and because of this I knew something was not right, this is my story of how I have got to the stage of my life. This is all true and edited for Literotica's readers, I pull no punches at all and have experienced a interesting life so far. I hope you en...

My Life

by jimhaullis on Sep 16, 2017
Fetish

Please tell me what you think! I'm I the only married man that enjoys having his wife in pantyhose? Am I the only man who is lucky to have a wife that enjoys role playing? * Start: I'm not sure really sure when it started or how it started but for as long as I can remember I've loved pantyhose. My mom worked at a bank during the day and at night in a rest...

Hypnotized, Maybe?

by hypnocd on Sep 13, 2017
Transsexuals & Crossdressers

"You want to what?" "I want to try to hypnotize you. C'mon man, it's nothing worse than some of the other stunts we've done together." This, coming from Cliff. Sure, he's my roommate but sometimes I think he's plain crazy. "Yeah, and how many of them did you start? And then try and tell me how many went right. Why should I trust you with this? For all I kn...

Caught in Ex-GF's Underwear Pt. 01

by HiddenThoughtz on Oct 6, 2020
Transgender & Crossdressers

Hello everyone...welcome to my crazy kinky life lol. This origin story takes place right before my 21st birthday. This all started when I finished my junior year at college. School had ended and I was taking summer classes so my workload senior year would be easier and I could enjoy my last semester. My two roommates had gone back home to work for the summe...

A Bride's Sexual Lingerie How To

by ErnstBlofeld on Sep 13, 2017
How To

A Bride's lingerie A guide on bridal lingerie and how to consummate your marriage while wearing it As told to the author after a six hour marathon love making session at the Hotel Monte Carlo, 2001 Before I start this primer on wedding night sex and lingerie, I would like to clear up some misunderstandings that our lingerie ignorant culture has been spre...

Dressed To Please Kate Pt. 02

by jealouscuck on Sep 25, 2017
Transsexuals & Crossdressers

Kate and I went from newlyweds to a loving dominant/submissive couple. I had been introduced to feminization and really loved to be dressed totally. We had close friends who had actually introduce Kate and ultimately me to the lifestyle. While most of our life was "normal", we became very active in the alternate lifestyle. We would go shopping with me dress...

Making a Sissy Jock Pt. 01

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

My life changed about a year after I was done college. I'm Mason, or I was and I used to be a football jock all through high school and played all through college and after all that I kind of just never got picked up. So...what do you do with a physical education degree? Most guys taught gym or coached some places. Me? I got a massage job at a spa. There...

The Alpha Who Made Me a Sissy Ch. 01

by HB77 on Jul 31, 2019
Transgender & Crossdressers

So there I was again on all fours in his bed. My peach coloured thong panties pulled to the side, and my daddy behind me with one hand on my hip and the other Gripped onto the back of my red corset. Chad relentlessly filling my ass pussy with his gorgeous rock hard 8" as I moaned "oh daddy, oh daddy don't ever stop fucking me, I love you" over and over in my...

Cumshot Addict

by monsieur_venus on Sep 14, 2017
Toys & Masturbation

Johnny had always preferred the money-shot endings of porn movies to the acrobatic positions and over-acted, fake-sounding enthusiasm of the rest of the scene. By the time he got to college, he had discovered streaming porn sites where fellow cumshot-lovers uploaded compilations of their favorite happy endings, conveniently edited together to maximize jackin...