Pantyhose Gay Stories

28,408 results
Orientation
Length
Source
Infinite Scroll

Night One

by Tess_PartySlut on Sep 16, 2017
Transsexuals & Crossdressers

I spent the day with nervous jitters, after you told me what you wanted to do. I was to be your sissy slut and venture to the glory holes to suck cock for you. I rushed to the hotel after work, to begin getting ready. I knew I really needed you to complete the Tess transformation, but I would do my best. Three razor blades later, a good portion of the fur wa...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Eustace Johnson's Private Secretary

by andtheend on Sep 19, 2017
Interracial Love

Susan's first job was working for a powerful, wealthy, albeit perverted, black man. Oblivious to the horde of Christmas shoppers in his store below and with the music of Nat King Cole's Chestnuts Roasting on an Open Fire playing so much like elevator Muzak in the background of his private office, Eustace Johnson, a big, black man, had enough of his new, whi...

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...

The Proof is in The Pudding

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

When my girlfriend of two years mentioned she liked to watch female impersonators perform, I seized the opportunity to confess my lifelong addiction to cross-dressing. The expected reaction of disbelief was no surprise but her reply of, "Well, let me see you dressed," was although welcomed, a bit of a setback. I'd not planned the truth to be revealed at suc...

Cross Dresser Flashing for Nude Day

by SuperHeroRalph on Sep 16, 2017
Transsexuals & Crossdressers

This is a Nude Day contest story. Please vote. * Having fun flashing the sexy, pretty neighbor his pantyhose clad cock on Nude Day James, a cross dresser, had some sexy flashing fun planned for Nude Day. Taking a long sensual and sensuous bubble bath first, wanting to look pretty, feel sexy, and smell divine, he took his time getting ready by shaving, wax...

The Game Ch. 03

by MicheleNylons on Feb 11, 2019
Transgender & Crossdressers

Chapter Three - Translucent 22 September 2007 Petra awoke mid morning; she felt a little hungover and her anus was tender. Vignettes of the previous evening played across her mind as she lay in the bed under the pink satin comforter; she had a morning hardon tenting her panties which she lazily stroked as she recalled Mick ravishing her right here in this...

Wearing Her Clothes

by TheEvelyn on Sep 17, 2017
Celebrities & Fan Fiction

This is going to be the best Halloween ever! I took off from work early to avoid the holiday traffic; it's always crazy on Halloween, with people becoming absolutely desperate to dress up as a nurse or a caveman or a pirate. Rushing around, going to their parties... I'm not going to a party; I'm spending Halloween on my own. I have a plan... I also have the...

Friends Finally Connect

by OultawHoseAndStockings on Sep 14, 2017
First Time

Everyone in this story is 18 or older and any resemblance to people real or fictional is coincidental. * I am a slightly chubby band nerd and generally just a nerd with a life-long fetish for girls in pantyhose or thigh high stockings. I don't know why but I just love the way women look in them. My love life up to this point was basically non-existent. I h...

A Special Night, Laci's First...

by Sissy_Chantel on Nov 27, 2018
Transgender & Crossdressers

Prologue: My name is Lawrence, I'm a young 40 something widowed white male, living a heterosexual life. However I have my feminine side, her name is Laci and as such I am a transvestite. I have preferred the long classical term of transvestite for a genetic male who dresses in women's clothes. But crossdresser also works as well. As a transvestite in my fu...