Gay Pantyhose Sissy Stories

820 results
Orientation
Length
Source
Infinite Scroll

Steve's First Gay Sex Ch. 01

by stevemike08066 on Dec 12, 2018
Gay Male

My name is Steve, and I recently turned homosexual, and I now serve a very tough, but fair Master who loves and let's me cum as much as needed. This is the story of how I was not only turned gay, but also submissive. I was having dinner with my girlfriend one night, and we're about to leave when I had to use the men's room. Now to describe myself, I'm 5'...

Curiosity Fucked the Straight Guy

by silkstockingslover on Sep 25, 2017
Gay Male

Editor's Note: this story contains incest content. NOTE 1: A special thank you to Estragon and Goamz86 for editing this lengthy multi-chaptered journey. Curiosity: Fucked the Straight Guy I can't explain for the life of me when I suddenly became curious. I mean I am 44 and have never found any man remotely attractive. Oh sure, I can tell when a man is goo...

Sunday Morning Deja Vu

by thebikinilover on Aug 18, 2017
Gay Male

I woke Sunday morning with a nice hard cock which I felt obliged to stroke to orgasm. I love the feel of nylon on my cock and walked over to my underwear drawer to rummage through my pantyhose collection. I decided on a natural shade and sat on the bed to pull them on. I balled up the left leg and placed my foot in the toe. Gently pulling the pantyhose up t...

Pantyhose Seduction

by nylondad on Sep 17, 2017
Gay Male

I was single and aged 26. I had been engaged for two years to a beautiful woman but the relationship had gone stale for each of us. We had lived together in a garden apartment for two years and she chose to move out and was staying with her parents until she could find a new place. I was sad as I missed her but felt relieved with the knowledge that the word...

A Fitting Surprise

by thebikinilover on Aug 18, 2017
Gay Male

I had a wedding of a friend to attend and needed a new suit for the occasion. This was Thursday afternoon and the wedding was tomorrow! Although leaving it late, I was sure I would get a suit off the rack as my size is fairly average. Traffic in the city was heavy and time was tight getting to the shop before closing, but I arrived at 5.20 with ten minutes t...

Sissy's BBC Submission

by tawnysuede on Sep 19, 2017
Gay Male

Chapter 1 - First Contact "Tyler! Snap out of it - you're staring again, and he's noticed!" Jack's voice whispered hoarsely in Tyler's ear as the hot water from the shower drummed across his back. There were just the three of them left in the shower now. Basketball practise had been over for more than half an hour and the most of the players were showered...

30-Days of House Arrest Ch. 02

by bjmichaels on Dec 4, 2017
Gay Male

It was hard to concentrate on washing the breakfast dishes and cleaning the kitchen. Mister G was in one of his playful moods and couldn't seem to keep his hands off me. He massaged my shoulders and back and occasionally a hand would slip beneath the waistband of my shorts and claim possession of a buttock, squeezing and pinching it. Needless to say, I wou...

That's My Good Boy

by Submissivegoodboy on Sep 21, 2020
Gay Male

Bethany and I arrived at the hotel early that morning. We spend the day talking, snuggling, kissing, giggling and getting ready. Around midday I go into the bathroom and shave my body, we want me to feel extra sexy and feminine for my first time with another man. Mmmm as I come out naked and smooth Bethany giggles and jumps up and runs over to me. After sl...

Research Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

Please read Research part one first. ***** "So in summation I submit that although a certain portion of the male population engages in homosexual acts, they aren't homosexual at all. No, they are under-endowed males who wish they could have heterosexual relationships but whom women shun. Through aggressive parenting, peer pressure, and social activities th...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...