Pantyhose Boy Stories

109,177 results
Orientation
Length
Source
Infinite Scroll

Walk a Crooked Milf Ch. 01

by MicheleNylons on Nov 16, 2020
Transgender & Crossdressers

Chapter One - I Don't Go To Church, Kneeling Bags My Nylons For as long as I can remember, I've always loved watching Mrs Cashmore walk to church. To be fair, I've always loved watching Mrs Cashmore do almost anything. But Sundays were special because she dressed for church. A tight figure-hugging suit with a skirt that was not immodest but it was moulded...

Sperm Bank Artists

by wordyone on Oct 29, 2018
Fetish

The mere sound of the door to the flat being closed behind her was sufficient stimulus to cause my cock to start to swell. The explanation was simple, I had learnt to associate this sound as a starter for fun, it indicated my roomie Catherine had left the flat to go to her work. It meant that I could sneak into her room and have a good rummage through her la...

First Explorations

by MrShyTown on Sep 12, 2017
First Time

The boy was newly 18, and had the run of his father's house for almost a full week. His newly acquired, and for that matter his "girlfriend" Melissa, his first ever, was prone to showing up at his door late at night unannounced, essentially looking to make out. The boy didn't mind this at all, of course, but as the living room was bounded by windowed French...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

You Got the Part! Ch. 03

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

I would like to thank Mr_Owlow for all his assistance with editing this story. In typical Riley fashion I was in a bit of a situation. GiGi's T.V. show was a complete success and we were picked up for a second season. America was in love with the cast especially GiGi and myself. We were making the rounds on talk shows and late night. We were doing endorse...

Cougar Fantasy

by stephanie_webster on Sep 17, 2017
Loving Wives

Please ask for permission to post on other web sites or distribute. I'm looking forward to hearing what you think about my fantasy and real life story! Don't be shy, send me an email. I read a story like this on a web site, tried contacting the author, but was unable to get a response. Working at a bank well I have to wear pantyhose every day. I'm also a pe...

Biker Bitch Ch. 01

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter One: Cassie Cassie woke up feeling hungover, hungry, thirsty, beaten and abused. She was still chained to the billiard table in the Beasts of Burden Motorcycle Club clubhouse. She rubbed her ankle where the chain was manacled to her leg. Her nylon stocking had worn through and her skin was red and bleeding. Had it really been four days? Cassie s...

Dottie and Me Pt. 02

by usemetoday1962 on Sep 16, 2017
BDSM

So if you read my last entry you knew about Dottie and that I worked with her in the hospital. I never worried about what I wrote because, quite frankly, I didn't care. Well Dottie found out that some other employees of our hospital also read stories. One in fact worked for her. Chris was a nurse in charge of compliance. She was about 35, 5 foot and 250 lbs....

Laura's Pantyhose

by flim62 on Sep 26, 2017
Mature

When I was 18 my family lived in the English Midlands. My parents both worked for a pharmaceutical firm and they were working at its English subsidiary. We lived in a small village about 20 miles outside of Birmingham. Because both my parents worked they could afford to send me to a public school—which in England means a private school. The school was...