Pantyhose Crossdressing Stories

7,638 results
Orientation
Length
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Hotel Encounter Pt. 01

by Jay876 on Aug 20, 2019
Transgender & Crossdressers

Jay was a 5 foot 10 Indian boy, he has longish hair and he is a little chubby. And this is the story about how he lost his virginity. He was sitting at home browsing through the gay apps. His hand slowly rubbing his dick. Just enjoying the erection. When suddenly he received a message from an older white man. Jay had always fantasied about being with an old...

Curse of the Living Clothes

by calx86 on Jan 8, 2020
Fantasy

There are several stories out there involving living clothes but I want to leave this open to allow many collective authors to be as creative as possible. For example, you can write a story about clothes simply coming to life and stripping their wearer, leaving them nude and embarrassed or maybe the living clothes forces someone to wear them and turns them i...

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Encounters of a Crossdressing Slut

by KAshton on Sep 16, 2017
Transsexuals & Crossdressers

This is an introduction to my crossdressing experiences, touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever. I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like sli...

The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...

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...

Cocksucker: Crossdressing

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Straight man is forced to cross dress and suck cock. You do not need to read the first parts to enjoy this story about a straight man crossdressing in San Francisco. In case you are curious about how he ended up in this situation here is a brief summary of the first two parts of the "Cocksucker" series: Chris, a married straight man, is stuck at t...

The Awakening Ch. 03

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part Three - The Cost of Doing Business The woman is slim. Mauve satin blouse, navy-blue skirt, black high-heeled pumps. The hem of her skirt teases the backs of her knees. Taupe stockings with black seams. She's attractive; heavily madeup and her black bob is obviously a wig but of good quality. She falls to her knees and smiles. A faceless man approaches...

Home in the Hills Pt. 02

by ValoryG on Dec 16, 2019
Transgender & Crossdressers

Jonathon had to endure two weeks of waiting until his next session, if it could be called that, with Nora. Nora -- a name that might've once seemed unexciting, now seemed sexually tinged and full of possibilities. Nora began to play a major role in his masturbation fantasies, until what he was imagining departed greatly from the real woman. At some level he...

Fetishville (Adding Encouraged)

by VioletWinters on Sep 26, 2017
Fetish

Welcome to Fetishville! I am Violet, the mayor here. I know you're eager to start so let's get to it. To begin with your adventure, press the "Start Game" button on the right and find your fetish. It is pretty straight forward. If your fetish involves dominating, select [Dominant]. If it involves being dominated or being submissive, select [Submiss...

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Sicily's Lesbian Son Pt. 02

by SubtleDeviance on Jan 29, 2020
Transgender & Crossdressers

Story contains themes of crossdressing, feminization, incest, and anal play Dante awoke with a little tent in his white lace panties, excited about the day to come. He smiled to himself and stretched across the clean white sheets, wearing one of the babydolls his mother bought for him, sheer, white and sexy. His bed had been the only place he could safely...