Gay Crossdressing Halloween Stories

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At the Movies

by Michele G on Sep 14, 2017
Gay Male

Everyone knows Bobby and I are friends, but the don't know how close of friends were are. He's known about my crossdressing for sometime because we have been lovers for that long. One weekend my folks were away Bobby called me and asked if I'd like to get dressed up and go to the movies. At first I balked at the idea of going out in public dressed up, even...

Frat Party Costume Sex

by SluttyBisexualGuy on Mar 2, 2020
Gay Male

This is the story of how 19 year old Caleb Jensen found himself in the sexual predicament of a lifetime. It was the fall rush season and Caleb had been accepted as a pledge at the USC frat of his choice: Tau Kappa Epsilon. Their off-campus reputation was legendary and they threw incredible parties that people talked about for weeks. The girls that attend...

My Inner Slut Ch. 03

by SlutAlexR on Oct 15, 2018
Gay Male

Well, no doubt about it: I was a slut. I had sucked my first cock; I had been fucked hard in the pussy; I wore girlie clothes for my Man; and here I was, his load drying on my face, ready to leave the house. Todd had laid out a few things he wanted me to wear during the day. Skinny jeans, a tight white t-shirt. Nothing too drastic there. But I had to wear b...

My Gay Crossdressing Vacation Ch. 02

by Flame666 on Apr 21, 2020
Gay Male

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some e...

The New Order Pt. 04

by Iamkrazy4 on Apr 21, 2020
Gay Male

Part 4: On The Road to Love There I was, on my back, a dick in my butt, mouth, and both hands as I laid on table they had brought into the locker room. Around 3/4ths of the football team, and the coach stood around cheering as they celebrated their upset victory over our rivals. My throat and ass were sore as this onslaught had been going on for over an h...

All Hallows Eve

by SamCateu on Oct 29, 2010
Gay

Today is Halloween. You, John Doe, are to be at a Halloween party tonight. However, you have forgotten to buy a costume. Upon realizing this, you rush to the nearest costume store. The limited selection is rather slim, considering it's the day of Halloween. In the men's aisle there is only one costumes to pick: a vampire. However, feeling that perhaps you ca...

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Halloween Job

by timtrack on Aug 18, 2017
Gay Male

Throughout college I took several opportunities to work what could best be described as seasonal jobs to give me some extra spending money. So at the beginning of the school year, I'd work at some of the last festivals of summer, Oktoberfest, then Halloween and usually some extended work for the holiday season. It sometimes paid cash but always allowed for m...

Halloween Revisited

by sack on Aug 18, 2017
Gay Male

David felt a heaviness in the air as he hurried toward the hidden wine cellar. The sky had turned inky black and a few stray raindrops stung his face in the overcast gloom. It was Halloween, and night was swiftly falling. David had taken his strongest flashlight, complete with new batteries to cut through even the pitch black hiding place he had recently dis...

A Manly Costume

by Bethyboo on Sep 14, 2017
Gay Male

Joey, Bill and Morty. The three amigos back in town at the same time for the first time in 30 years. They had been best friends, and had gone through first bicycle crashes together. First girlfriends, first drinks and unfortunately that one time they had gotten hold of some stink weed when they were 15. That was a memory all three friends would rather forget...

Gay Mascot Halloween Masquerade

by andtheend on Aug 31, 2017
Gay Male

College football mascot has gay sex with his best friend. Chris and Jeff were lifelong BFF's, best friends forever. Chris was gay and Jeff was straight. Jeff always teased his best friend about being gay. Chris didn't take the good natured ribbing from his friend seriously, it was only his best friend goofing on him, which they constantly did with everythin...