Gay Tights Crossdress Stories

168 results
Orientation
Length
Source
Infinite Scroll

Christmas Hunk

by Pelaam on Sep 14, 2017
Gay Male

Based on a picture from Millie and dedicated to her with grateful thanks . Pelaam, December 2007. * Curtis edged carefully in the darkened store towards the figure that was moving around his displays. He might be the Store's Managing Director, but he was more than happy to take on some two-bit, petty thief that thought they could hide away after hours to...

Blackmailed and Seduced by Peter

by johna1441 on Oct 5, 2020
Gay Male

I spent the summer after my last year of high school working at a restaurant on the west coast, at a small resort town on the ocean close in Sonoma, California. I had grown up in a smaller town in the middle of nowhere in Ohio, and wanted to see a bit of the country before starting college in the fall. I also wanted to find a way to forget about my last year...

Nephew's Readjustment

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Cynthia's life had improved drastically in the past two years. Most people would consider getting a divorce at thirty years old pretty bad. A divorce due t...

Dark Stag Ch. 03

by StillnessIsTheTruth on Sep 14, 2017
Gay Male

ROI: Everyone was so surprised that I was the first one out on the balcony this morning. In all honesty, I don't know what brought me here. Upon a second thought, burying my head in the pillows of bed seemed like a better idea but I couldn't leave now. The family was starting to arrive. Mother sat directly in front of me, at a loss for words. My sister and...

Cobalt Blue Ch. 14

by Pelaam on Sep 26, 2017
Gay Male

©Pelaam: February 2008. Four strong-minded individuals were at a round table and arguing as strongly an hour after they had all first sat down. Jaze's team had been given a spate of attacks on female prostitutes to investigate. The victims were little help. They were stunned with tasers before they could get a good look at their attacker. Height, estimate...

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...

Box Shaped Heart Ch. 13

by laurasfox on Jan 1, 2019
Gay Male

Chapter Thirteen - Little Boxes He woke up with the first rays of sun gently invading the room through the curtains. He could not remember ever feeling so well rested. Usually, he was a fussy sleeper, as there always had to be something ready to annoy him, be it a crumpled sheet, a pillow all in knots, or his own mind trying to solve this or that. "Morning...

No Other Life than This Ch. 05

by podga on Sep 14, 2017
Gay Male

It had been gray and drizzling the entire week, the kind of weather that drove Benny up the fucking wall, and by Saturday afternoon he had a severe case of cabin fever and went out running regardless of the rain. At first the run felt rough, his limbs and breathing uncoordinated, but by the time he'd reached the Reservoir loop, he'd smoothed into a fluid rhy...

The Greek Pimp Ch. 06

by sr71plt on Aug 30, 2017
Gay Male

The man put his arm around Rick's shoulder as they left the elevator on the fifteenth floor of the Mandalay Bay hotel casino in Las Vegas. When they'd met in the lobby of the hotel, the man hadn't even maintained eye contact with him other than to nod his head toward the bank of elevators, signaling that Rick was to get on an elevator with him. The john was...

Marlee's Christmas Gift

by sr71plt on Sep 16, 2017
Gay Male

I took one last look at the antique broach, closed the lid of the velvet box, got up from the desk, slipped the box into the jacket pocket of the clothes I'd laid out on the chair next to my studio couch, and came back to the desk. I'd left the drawer open. I took out the worn stack of postcard-size photographs I kept in the drawer and started shuffling thro...