Gay Crossdressing In Pantyhose Stories

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Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...

Pretty Boy

by today_i_am26 on Jul 13, 2020
Gay Male

"Aren't you a pretty boy?" He said with a leering grin. I was on my second day of my new job and I had been tasked to drive the van to an industrial estate in the rougher end of town to collect some items and drop them off to the customer. I had walked through into the warehouse where I was confronted by a man in his late 40's with a strong accent, tattoos,...

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...

Finally, Fucked

by Willing2Do on Aug 18, 2017
Gay Male

Cockwhore that I am I have been giving these two guys blow jobs on a regular basis. Actually I suck them, mouth their balls, rim them, and they often fuck my pussy mouth. Though different both of them have nice cocks. One is married and older, in his 40s. The other is single, 20-something-year-old. The married guy's cock is average - 5-6" long, about 4" ar...

I'm a Crossdressing Cum Drinking Whore

by tcorbin on Aug 30, 2017
Gay Male

Australia and me in the States. I shared every one of my darkest fantasies with him and he loved everyone of them. I had never been with a man before but was driving like hell to meet him at the motel he had arranged. He was finally making it to the states on business and had emailed me a couple days prior asking me if I wanted to get together. Until now it...

Enticed and Humiliated Ch. 15

by FantasizeAndRealize on Sep 14, 2017
Gay Male

Part 15 - Hustling at the Gay Bar I couldn't believe that I had received $50 for giving a blowjob, the previous night! If I could do that a few times a week I would be set financially. I could finish my senior year and then do a Masters program, with no worries about where my beer money would come from! I decided to check out this Buddies gay bar. I was a...

The Boifriend Ch. 02

by AdmiralSquish on Jun 19, 2019
Gay Male

[pre-story]This story's not dead! I was a little stuck trying to figure out what to work on, and I got some comments recently asking for more M/M stuff, and then I got inspired and now here we are. Convenient that the first story to go public in pride month is M/M. Content Warnings: M/M, femboy, sissy, potentially offensive dirty talk Disclaimer: All chara...

The New Order Pt. 01

by Iamkrazy4 on Nov 4, 2019
Gay Male

Part 1: A Bottom's Duty Political strife. Riots. Violent crime. Impending war. These thoughts were all far from my mind as I slowly moved my dildo out of my well lubed ass in my dorm room. I bucked my hips to meet every thrust of my hand as a video compilation of huge clocks flashed across my laptop screen. Finally...it happened. I had a huge orgasm and I...

BBC: Like Son, Like Father

by silkstockingslover on Jul 9, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. Summary: Father catches son sucking BBC & gets very curious. Note 1: This is a NUDE DAY 2019 story so please vote. Note 2: All participants are at least 18-years-old. Note 3: Thanks to Tex Beethoven and Robert for editing this story I'd just gotten home from work and was in the k...

Nephew's Readjustment Pt. 18

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after! Last part. ***** Cynthia took her nephew out again the next day under the pretense of it...