Gay Pantyhose Crossdress Stories

103 results
Orientation
Length
Source
Infinite Scroll

Birth of a Cock Sucker: 1980's Teen

by silkstockingslover on Sep 19, 2017
Gay Male

Summary: Straight shy guy walks into an adult theatre in late 1980's. Note 1: Thanks to Robert, goamz86, and Wayne for editing. Note 2: All participants are at least 18-years-old. Birth of a Cock Sucker: 1980's Teen Who: Me, a young naive guy What: A story of how I learned I was a natural cock sucker Where: Toronto, Canada When: 1989 How: Wel...

Bob Handles Mark's Huge Tool Ch. 01

by scrotus on Aug 18, 2017
Gay Male

I had long fantasized about being involved in a sex situation with more than one guy. I had done several three ways with a woman (two guys and one girl) but they never involved the other guy and I performing on each other. In recent years, I've developed an insane desire to move beyond my several male-male encounters and add a third guy in. This is because o...

A Natural 'Gurl'

by sexyR2 on Aug 18, 2017
Gay Male

Yes, I know that it has been a few years since I last posted. I was busy. I hope, however, that this new story makes up for the delay. It is in a new category for me, gay male instead of gay female like two of my previous submissions. Enjoy! Debbie, er, sexyR2... ***** Today... When the somewhat urgent knocking came to the door, Debbie knew in an inst...

Gay Students at Private School Ch. 02

by walterio on Feb 12, 2019
Gay Male

SUNDAY IN THE DORM Sunday morning, Jeremy and Cody woke up late. In fact, they were too late for breakfast. They were still tired and feeling a bit constipated which was understandable from all the anal sex at the principal's home. First Cody and then Jeremy went down the hall to the bathroom to take their morning piss. They didn't need to shower as they ha...

Straight No More: Getting Ahead

by silkstockingslover on Sep 25, 2017
Gay Male

Straight No More: Getting Ahead Summary: Straight man's interview includes taking cock in both holes. NOTE: This is a NUDE DAY 2014 contest story so please vote. Thanks: Richard, goamz86 and MAB7991. Straight No More: Getting Ahead This was the biggest opportunity of my career. A shot at joining the most respectable law firm in Seattle. I had already go...

The Birth of a Sissy

by sissymedic1426 on Sep 14, 2017
Gay Male

After some careful planning and serious consideration I had made the decision that I would use my parent's birthday present to me to travel to Orlando, FL. They have a University there and tons of other things to see. For a kid from a little town in NC it felt like the biggest city that I could visit and still be safe (they have the house of mouse what's the...

Falling for My College Roommate

by Str8SensitiveGuy on Jul 27, 2020
Gay Male

My name is Tommy. I grew up in a loving, close-knit family. I always had the support of my family and friends. When I was 16 years old, I came out as gay. My parents and my siblings had no issues accepting me for who I was. I was very fortunate. We lived in a small suburb of a big city. It gave us the feel of a small town with the convenience of everything...

Straight Teacher Turned

by silkstockingslover on Sep 25, 2017
Gay Male

Summary: Straight teacher is turned by two ex-students (1 black, 1 white) Notes: Thanks to goamz86, Robert, and MAB7991 for editing. ***** I was in a bar in the big city an hour from where I taught. One of my favorite eighties bands was playing and although my wife didn't want to come, I wasn't missing it for the world. I wasn't in the bar five minut...

The Tailor's New Shop Boy

by ThomasStevenson on Nov 18, 2019
Gay Male

"Gotta go, this is my stop." Philip fired off a farewell text to his friend as he got up, shoving his thick, hairy, tan feet into his flip flops. He didn't bother adjusting his singlet, which continued its slide down one of his muscular shoulders, slouching halfway down one side of his beefy rugger's physique. A dusting of reddish chest hair made a thin "t"...

Born to Suck Ch. 03

by rmdexter on Sep 19, 2017
Gay Male

As I heard the other boys coming in, I rushed down to the dining room and was one of the first ones in line for lunch. As one of the councilors filled my plate, I saw Mrs. Nesbitt take a tray of food and a drink down the hall for Mr. Jarvis. Whereas the other councilors always ate with us, Mr. Jarvis nearly always took his lunch alone in his office. I felt...