Gay Crossdressing In Pantyhose Stories

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Can I Borrow Your Boyfriend?

by knowsbetter on Mar 2, 2020
Gay Male

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions. "B...

Exploring My Bi Side Ch. 02

by bscurious1 on Oct 19, 2020
Gay Male

Randy and I kept up our meetings, sometimes weekly sometimes two or three times a week, just depended on our schedule and how horny either of us were. We always met at his house in his home studio which offered us a lot more privacy and freedom. As I had stated the massages pretty much stopped but he would still give me one when I needed one or just wanted o...

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...

I Once Was Lost But Now Am Found Pt. 02

by eviltwin52 on Oct 5, 2020
Gay Male

In Part 1 I found a friend in Leon. Having lived the greater part of my life alone, maintaining my bond with Leon was the most important mission I'd ever had. Sucking his cock was my way of showing him my appreciation for his comradery. He didn't ask me to do that. He didn't tell me to do that for him either. All Leon did was nudge me in the right direction....

My First Time Ch. 02

by doctrtic on Aug 18, 2017
Gay Male

This is part two, Michael had me in hose on all fours and was milking and edging my cock. Ch. 2 The Seduction "AAAHHH" I swooned, my head spinning, I want to cum NOW I was thinking. Michael was not thinking the same thing he was an edging master, he was going to bring me to the brink of orgasm and have me begging him to let me cum. He started slowly...

Coming Out on the Swim Team Pt. 07

by walterio on Jun 17, 2019
Gay Male

ESTABLISHING A ROUTINE The first week for the freshmen was always a challenge. They had to balance class time, training, homework and sex. They were for the most part too tired the first week for nightly sex. In fact, they waited until Saturday to have sex in their dorm rooms. On Sunday they were in the training room for massage foreplay and group sex. Coa...

Just a Game Ch. 02

by tamgreen on Sep 14, 2017
Gay Male

Pete woke up alone, and the apartment smelled amazing--something delicious was cooking. He tottered unsteadily to his feet and looked down at himself. He was wearing nothing but a t-shirt and a furious hard-on. He pulled on a clean pair of boxers, stuffing himself awkwardly into the fabric tent before trudging to the kitchen. Dean was standing at the stove n...

My First Anal!

by MrJimJim on Aug 18, 2017
Gay Male

Once I had finished giving my first blowjob, I knew it wouldn't be my last. In fact, I stopped counting! One of the guys I sucked on often was nice. Latin, firm, long slender cock just perfect for being naughty with. We had been together enough times we were comfortable in each others homes. We would fool around at his house or outside in the rain. I would...

My CD Slut

by eljayb on Jan 23, 2019
Gay Male

Sweet encounters As a sexually active 77 year old I have recently been attracted to the lovely world of Crossdressers. Not that I wish to dress myself but I enjoy the company of those who do. In my travels I found this interesting personality called Chrissie. Age 64, CD/TV/TS. After we exchanged messages and emails for a while, I felt we might get on well...

The Hapless Detective

by idsweaterguy on Sep 16, 2017
Gay Male

Chapter 1: I parked my car four houses down from the house the man I was following had parked in front. I watched the middle-aged man who was about six-two and wearing a brown fleece jacket, jeans and a brown baseball cap get out of his car, throw a backpack over his shoulder and walk up to the front door of the non-descript but rather large house in a newe...