Gay Costume Stories

398 results
Orientation
Length
Source
Infinite Scroll

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...

Historic Costumes

by MSTarot on Aug 18, 2017
Gay Male

The phone has been ringing off the hook for the last week. "Historic costumes," I paused and waited for the inevitable question given it was October. "Yes, ma'am, we do rent for Halloween. No, we only carry costumes from pre-nineteen hundred." I rolled my eyes at the Hanna Montana as a slut request. "Yes, we have several pirate costumes in stock." Holding...

Timber Pack Chronicles Ch. 01

by robcub32 on Sep 25, 2017
Gay Male

Parker Montgomery put his contact lenses in and took one last look in the mirror. He blinked twice, letting the plastic lenses settle over his green eyes. He ran his hand through his hair. The short and spiky dark blond hair was as good as it was gonna get. At least the messy style hid the stupid cowlick on the crown of his head. He was dressed simply in a...

Midnight Masquerade

by Xathandra on Aug 18, 2017
Gay Male

Getting out of his car, Mark turned to look at his sister, Katie, shaking his head. Once more she had talked him into another crazy idea and he couldn't quite figure out how she'd done it. Ever since they had been young children, his twin had the uncanny ability to bat her eyes at him and get him to do her biding. He contemplated getting back into his car an...

Weekend with the Boys

by billluc on Aug 18, 2017
Gay Male

Growing up I did a lot of the normal things guys do, checked out playboys and jerked off with a buddy. One time we took two pairs of his sister's panties and wore them. We never touched each other and we turned our interest to girls. I also checked out the other guys in the locker room but never acted on anything. Then in college my roommate and I had a thre...

Spiking the Eggnog

by ladynina23 on Apr 1, 2020
Gay Male

*All characters are above the age of 18 "Shhhh! You're family is going to hear us!" I shushed my boyfriend before going back down to swallow his cock to the root again. We were at his Mom's house for her yearly Christmas Dinner. About two hours had gone by when Ryan snuck up behind me. After five cups of eggnog, Ryan cornered me under the mistletoe and sai...

Gloryhole Illustration

by MVP6 on Jul 15, 2020
Gay Male

In my last letter I wrote about my first experience sucking cock. It was really great and if you want to read about it the title of the story is "Costume in a Costume." In this letter I will share my next interesting experience: It was now August and I was anticipating Halloween which would be here soon. This year I was planning to dress up as a woman aga...

Halloween Rabbit Holes

by hornyyoungboylovesolder on Jan 15, 2019
Gay Male

I had seen some men, one man many times, and was having a lot of fun. The one guy I was seeing constantly was 58 a bit of a belly, but an amazing cock. After a bit he had gotten me into cross dressing. It started with panties. Then stockings and heels. Leading to bras, skirts, and wigs. Eventually I was putting on make up, eye lashes, lipstick, the whole nin...

Buddy

by MVP6 on Jul 15, 2020
Gay Male

This is my sixth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. Maybe not my best but it has an important message. In my first letter "Costume in a Costume" I describe how I dressed as woman in a Halloween costume to trick unsuspecting men into letting me give them my fir...

Carnival at Viareggio

by sr71plt on Sep 14, 2017
Gay Male

All characters are over 18. ***** "I've never looked out on the Tyrrhenian Sea before. All in all the beaches of Viareggio surpass those we have visited in Venice. Perhaps we should just stay here longer." "I couldn't help but overhear you, sir," a well-dressed young gentleman, complete with white suit, vest, and white bowler hat and shoes called over fro...