Gay Wedgie Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men in underwear getting wedgies.

Wedgied at the Arcade (ch. 2)

By HandyDan 19 Apr 2026

Dan braves the arcade again but lets himself get distracted while his Bully is lurking nearby

9.1 (4) 87 11 Min Comments

Dan's Wrestling Adventures (ch. 3)

By HandyDan 11 Apr 2026

Dan is desperate to get his first win but can he outlast The Twink's endurance?

9.8 (8) 572 16 Min Comments

Wedgied at the Arcade

By HandyDan 5 Apr 2026

Dan heads to the arcade to try and get the Hi-score but someone else has plans for him...

7.0 (12) 1139 4 Min Comments

Property of the Jocks

By Gay Depraved Gooner 28 Feb 2026

An innocent dinner date descends into depravity as my wrestler date and his partner use and humiliate me. I didn’t think that they would care about the size of my penis, but they made me realize the only life I could ever deserve.

7.5 (14) 1357 13 Min Comments

Spontaneous Encounters (ch. 2)

By Robbie Watkins 23 Oct 2025

This short story is part of a fictional anthology series based on my fantasies about everyday encounters somehow turning into sex with a dom-sub dynamic, told from the top's perspective. Each story can stand alone. If rough sex, humiliation and verbal degradation are your cup of tea, this series is for you!

9.2 (12) 1487 16 Min Comments

Cody Burden has a Rough Night

By Pup Wedgie 21 Mar 2025

Cody Burden, a humiliation content creator has a group of his fans find him.

8.7 (13) 5756 37 Min Comments

Sam’s Frat House Invite

By Pup Wedgie 20 Mar 2025

An unexpected invite to the frat house, turns Sam into one of the bros… or so he thought.

8.2 (52) 6055 12 Min Comments

Jeremy Out of Control (ch. 2)

By WedgieLover 13 Feb 2025

This chapter covers the next man to take advantage of Jeremy’s curse. How will he be humiliated this time and what’s to come before graduation day?

6.9 (15) 2994 6 Min Comments

Jeremy Out of Control

By WedgieLover 12 Feb 2025

Jeremy our main character, is sharing his story on the curse laid upon him by his mother prior to leaving his life. It’s hell on earth for him, but pleasure to all others.

7.6 (14) 4321 9 Min Comments

Becoming an Athletic Supporter (ch. 2)

By TXE 15 Jun 2024

After Jimmy's early morning encounter with Ryan, he's woken up by his big brother Brad for a whole new set of experiences.

9.6 (74) 8523 37 Min Comments