Gay Nylons Stories

105 results
Orientation
Length
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Infinite Scroll

My Gay Crossdressing Vacation Ch. 04

by Flame666 on May 11, 2020
Gay Male

I slowly opened my eyes, remembering what had just happened over the past 24 hours, I woke up looked at the time, it was just before 7 pm. Earlier I had decided to start getting ready for my date with Paul and John around 7:30 so I got out of bed to get started. I was going to start with a shower and because I had a bit of extra time decided to take off my b...

Black Cock Worship: A Man's Fall

by silkstockingslover on May 1, 2018
Gay Male

Summary: Straight guard learns of black inmate's power over all. Note 1: This is dedicated to the real Ken who retold this surprisingly largely true story. Note 2: Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Prologue: I'm the prison guard and Kareem Mwangi is the prisoner, so you would have thought I had the upper hand, and until...

Jason's Costume

by nylondad on Sep 17, 2017
Gay Male

The following story is true. It occurred fifteen years ago. By virtue of the fact that yesterday was Independence Day jogged my memory. I had married a woman with three sisters. All but one of the sisters had kids. The oldest sister Carolyn (my sister in law) had a son by her first husband named Jason. He was a pleasant kid who grew up in with Carolyn and h...

Made A Man(In And)Out Of Me Ch. 02

by Cicero6 on Aug 18, 2017
Gay Male

Well, it had been three days since the party and I still felt like I’d been ridden hard and put away wet. Monday came and went and thankfully Kelly had not mentioned anything about the party. By Wednesday, however, I received a phone call from her at work. “Sweetie, I am wondering if you’re planning on doing anything this weekend,” she asked. I thought fo...

Fucked

by TerriC on Aug 18, 2017
Gay Male

It hurt. It hurt a LOT!! Every thrust was painful, even with plenty of lube. There was no numbing, no getting used to the feel. It was just painful. Yet, I let him keep going, it had to feel good at some point. An hour ago I was buzzed chatting online, horny as always when I drank. I loved drinking and chatting online, it was harmless fun, playing a role wh...

My Gay Crossdressing Vacation Ch. 02

by Flame666 on Apr 21, 2020
Gay Male

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some e...

The Bear and His Cub

by BigWig69 on Aug 18, 2017
Gay Male

I received a text from the bear, late one night in summer. The message was simple and to the point. Meet me at my place. Shave your cock, balls, legs and ass and if I find a single hair, I'll spank you blue. Dress according to my instructions; I want you wearing white nylons, tight, hip high. A white cotton thong, a super short plaid school girt skirt, gree...

The Shoe Store

by PhRedSonya on Apr 17, 2019
Gay Male

I have always enjoyed the feel of pantyhose on my legs, ever since I was a little boy. My name is John and I love to wear women's clothes underneath my work clothes. I am 5'8", have a slender build and keep my legs shaved all the time. When my friends ask why, I explain that it helps when I swim. Today, after work I had decided to go and check out the new sh...

Hard Worker Ch. 11

by tzael2003 on Sep 16, 2017
Gay Male

Victoria told me last night to get to work early to be in at 6am. So here I am at work, I'm wearing nothing but a red mesh garter belt holding up smokey seamed black silk nylons and truly whorish red shoes, with ankle straps, thick platform and seven-inch spike heels. The red of the open toes shoes match the red polished of my toenails. My seven-inch dick is...

My Journey into Bisexuality Ch. 01

by kinkymmale on Aug 18, 2017
Gay Male

This is a story about my first bisexual experience, but before I get into the details of what happened, let me explain myself a little bit first: I am a 26 year old married man that has been married to a beautiful wife for 3 years. Our sex life has been incredible! I have always wondered what it feels like sexually from the woman's perspective since I first...