Pantyhose Boy Stories

109,177 results
Orientation
Length
Source
Infinite Scroll

Caught in High Heels

by BigAndy922 on Sep 11, 2017
Transsexuals & Crossdressers

I couldn't believe the feeling as I slipped the pantyhose on over my legs. This was an absolute dream come true and I was living it right now. My friend Julie had gone out for the night with her 15yo daughter and she'd given me the spare keys to her house. She'd had a tradesman doing some work and needed to leave before he'd finished, so she'd asked me to...

Amy Moonlight's Stinky Knickers

by wordyone on Jul 14, 2020
Fetish

I had the panty time of my life. I was assigned the task of photographing the Edinburgh Festival for a fashion magazine, and my accommodation had been sorted out for me by a friend. I climbed three flights of stone tenement steps to a black door numbered twenty-three and rang the bell. The door was opened by a beautiful creature, little more than five feet s...

Decorating Her Dainties Ch. 02

by wordyone on Apr 11, 2018
Fetish

The second of several parts of my story 'Decorating her Dainties'. The reader is encouraged to read each part in sequence. * The very next morning when we were changing into our work gear, Sophia directed me to a paint-spattered retro canvas holdall with a tartan panel. She withdrew a transparent plastic bag which contained a bundle of nylon hose of all sh...

Annette's Barter

by rwsteward on Sep 26, 2017
Fetish

You had to be living under a rock this past year not to know the economy is in the pooper. But even in these economic hard times, people continue to buy houses. So it was when the old two-story cottage beside me went up for sale in the last quarter of 2007. It sat empty for nearly a year until a middle-aged woman purchased the property. That middle-aged wom...

Roommate Dress-Up

by silkstockingslover on Oct 26, 2020
Transgender & Crossdressers

Summary: Straight guy is feminized by female beauty. Note 1: This story is dedicated to the real Mike who requested this story. Note 2: This is a 2020 Halloween Contest Story so please vote. Note 3: Thanks to Tex Beethoven and Robert for editing this story. Roommate Dress-Up "Shit," I sighed, as I saw my outfit for the wedding... I should have guessed s...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

There's Something about Sarah Ch. 01

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Chapter One - Sloane Let's start at the beginning. "The last thing I need is another fucking mouth to feed! And a fucking boy at that!" That was what my Aunt Amanda said when I arrived on her doorstep. "Well we're dirt poor and this place only has two bedrooms so it looks like you're sharing with your cousin," were the next words out of her mouth. I wa...

I Need a Spanking

by addictedtonylon on Sep 17, 2017
Loving Wives

This story is written from multiple points of view. John and Jessica are married. Jill, Marci and Pam are John's employees. This is a long story, but I prefer not to write in parts Thanks to LSEiland for her very helpful editing Jessica: I was at home on a Friday, looking forward to the weekend, when the phone rang around 3 pm. I heard the hushed voice of...

The Cottage Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Mike Harris was seventeen years old when the worst blizzard ever to hit Chelmsford forest struck in December 1986. That is when this story really begins. But first we need to learn a little about Mike Harris before that fateful winter's day. Mike's father had left the family home when he was still a baby. He lived at home with his mother Doris and his older...

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...