Gay Wearing Nylons Stories

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Girlfriend's Dad Ch. 04

by Markf on Sep 25, 2017
Gay Male

While my high school girlfriend and her mom were gone on summer vacation, I had ended up being seduced by her dad. My summer job consisted of taking care of their home and pool, so I was not raising any suspicions at home. Everyday I would bicycle off to the Engle's. And every day I would spend my time sucking and fucking with Mr. Engle. I had progressed to...

My Gay Crossdressing Vacation Ch. 06

by Flame666 on Jun 9, 2020
Gay Male

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night. I remember...

My Gay Crossdressing Vacation Ch. 03

by Flame666 on May 11, 2020
Gay Male

I woke up. My bra undone, panties covered in lube and my nylons pushed down my legs. I felt as if I had been used. As I became more aware, I realized that I had been used and really enjoyed it. On the first day at the gay resort after getting dressed, I had walked over to a gay bar and been picked up by a nice guy, named Paul, just a bit older than myself. H...

Life on the Gay Side Ch. 02

by walterio on Dec 4, 2017
Gay Male

ANNIE LOOKS LIKE AN ANNIE Quincy had been bust all week at work and he looked forward to a relaxing evening and sex with Annie. They had not had sex in a couple of days and Quincy was thinking of that marvelous ass on the drive home. He had no idea what Annie had planned for him that evening. As Quincy was driving home, Annie was getting ready. Annie excit...

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...

A Night at the Movie turned me Gay Pt. 02

by jamtby on Oct 12, 2020
Gay Male

Entering the room immediately caused my stomach to churn with excitement. Something about entering a place where strangers are in control and you anticipate being involved with sexual activities. The what, why, and how remained a mystery. This only added to the combination of nervousness and excitement. The woman with a strangely deep voice said, "Welcome...

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...

Party with Wife and Her Lover

by colleenslittletoy on Sep 14, 2017
Gay Male

My girlfriend of six months came home all excited. This was a good sign I thought because I was afraid things had been getting a little dull lately. It seemed like she wasn't really into our lovemaking sessions and they were getting fewer and fewer. "I need your help!" she exclaimed when I asked her why she was so excited. "There is an important business di...

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...

MMF First Time

by Erotic Celt on Aug 18, 2017
Gay Male

From the moment I arrived I knew I was in for a treat. A sexual experience that would last with me forever. Janet had always been a sexual dynamo, and she could never get enough sex and was always trying out new things. I had only been going out with Janet for six months, and I already felt incredibly relaxed with her. Sometimes, I found, it could take years...