Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

A Ghost of a Chance

by sachiaiko on Sep 14, 2017
Gay Male

Sam was sprawled out upon the potato-chip wrapper strewn floor, one hand half wrapped around a forty ounce of bad, cheap beer. This was not the first time he’d passed out, all alone in his apartment, singing his own sad songs of remorse and self hatred. No, and to his way of thinking, it most certainly would not be the last. It hadn’t been long enough; Sam...

Avery's Desire Pt. 10

by Chancem77 on Jan 30, 2018
Gay Male

Avery and Rick arrived back at the apartment around ten that night. They were both pretty tired, but also excited. Their first date had gone perfectly, even despite Avery being nervous in the beginning. They decided to go to TJ's steak house and buffet. It was a favorite of Avery's but a place that he rarely had the chance to go to. It wasn't overly expensiv...

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...

Dr. Aaron and Officer Brian

by brian420d on Aug 18, 2017
Gay Male

When we met in the crowded living room he was flanked by a big breasted blonde on each arm. It was a Halloween party. He was dressed as a doctor, in scrubs. The two blondes had their asses hanging out of white mini-skirts that came in the nurse costume packages at the Halloween super store. He smiled at me and gestued his head like I should cross the room to...

All Souls' Day

by nomoretears00 on Sep 25, 2017
Gay Male

Special thanks to my editor WickedWendyDru for all the hard work she's done for me these past several weeks...you're one in a million, Your Wickedness! This story is entered in the Halloween Contest, so please remember to vote! * I had just gone on shift when word came through that major traumas were on the way. The ER braced for the seven car pile-up on...

Backstage Romance Ch. 02

by ikhneumon on Sep 13, 2017
Gay Male

* Daniel * I hustled into the karaoke bar twenty minutes late. Kelly's boyfriend, Josh, gave me a shout from behind the bar, where he was serving drinks at top speed to thirsty sorority girls in skimpy Halloween costumes. "Lewis, she's been waiting for you, like, half an hour! Be a pal, get your ass over there and calm her down, or I'm not gettin' any tonig...

Rex's Horny Halloween Pt. 01

by TeamCravings on Nov 27, 2018
Gay Male

(This new story carries on from, The Wonderful World of Rex) *** Lorna snapped one more photo as the train doors opened. The old frumpy, very tipsy businessman's balding head slid up and down Rex's cock with a gurgling sound. It almost sounded like choking really to Lorna's mind as the buzz of the very large crowd began to fill the carriage. Lorna made a q...

Black Eyes of the Fallen

by tamalied on Aug 18, 2017
Gay Male

"Dude, I'm totally going to have the greatest costume for the party tonightZacky squealed as he got his wing stumps attached to his back. Johnny, who had accompanied him to the store just shook his head and laughed at him. Zacky had been talking about how he wanted to be a fallen angel for Halloween ever since last Halloween. Johnny also grinned at the look...

Spellbound

by Gweall on Aug 18, 2017
Gay Male

Zelion glared at the pages in the book in front of him, the words blurring together. He had been studying for three hours straight and he needed a large cup of coffee to keep him focused. He sighed and sat up straight. "Still at it, huh?" Hex walked up to him, sitting at the oak table that stretched across the entire library. "Yeah," he grumbled. "But I co...

Drums in the Night

by KeithD on Oct 26, 2020
Gay Male

Rise, fall; rise, fall. This was usually when inspiration came to me—when I was riding a man's cock. It wasn't working today, though. Inspiration wasn't coming. Guido, an Italian-American hunk, even at fifty, was coming, however. The coming of Guido was well worth working for. I reclined back, grasping his knees, and continued rising and fall on his shaft as...