Gay Underwear Stories

6,363 results
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Infinite Scroll

Beary Christmas

by austexmale on Aug 18, 2017
Gay Male

My family opens Christmas presents on Christmas Eve, and my eighteenth Christmas was no different. We opened our presents according to age. The oldest go first, youngest last. This builds suspense for the youngsters, and keeps them from ravaging the house with their new toys while everyone finishes. My aunt's new boyfriend was my type of guy, but I was sti...

Influencer to Sex Slave Ch. 00 - Prologue

by dreamymark9 on Apr 3, 2019
Gay Male

Author's note: This is erotic fantasy and completely fictional. The main character, Jack, is a fictional, generic social media star / influencer, and is not a real person. As always, would love to get feedback in comments and messages. ***** For Jack, moving back to his hometown was risky, but something he really wanted to make work. He'd spent years build...

Knowing Myself is Riveting

by Servpet on Jan 8, 2019
Gay Male

Somehow, I ended up at a birthday celebration with my cousin, Susan, who had actually been invited. Her "boyfriend" couldn't attend, so she asked me to be her companion for the night. It was a casual event but classy. A band played soft jazz and some people danced around while the bulk of the celebrants mingled around the pool area. There was soft lighting...

Tales of Dick Ch. 06

by Bjsroxxs on Sep 1, 2017
Gay Male

Chapter 6: Beach Day ***Everyone in this story is fiction and is at least 18 years old or older*** ***** The next day I woke up to my brother's head resting on my shoulder. I slightly pushed him off, trying not to wake him. I glanced at the clock and saw it was still early in the morning. About 24 hours earlier, I was in the same position with two guys. N...

My BIG Sexual Awakening Ch. 02

by Andrsn on Jun 8, 2020
Gay Male

In the morning I wake up horny again. This is new. Daniel is already up, I can hear him in the kitchen listening to music. I grab my towel and head to the door to take a shower but something stops me. A temptation. I take off my clothes and wrap the towel around myself, my semi hard morning wood clearly outlined against the towel. Walking towards the door ma...

EDM After-Party

by RoyMarksman13 on Feb 25, 2019
Gay Male

Danny was shirtless when I arrived at his house - still undecided on whether to wear a blue or white tank top to the concert. He was hot in every sense of the word. He was 6'2" and ripped from head to toe, the result of playing hockey his whole life. I was always jealous of him. My body, on the other hand, refused to grow taller than 5'8". And while I'm in...

The Indebted Butler

by MelvinMhk on Aug 18, 2017
Gay Male

It had been almost two years since I had loaned Jake money so that he could travel overseas that summer with his friends. I knew then that he may never really be able to pay me the money back, but I didn't want to deprive him of the experience of going abroad with his friends. One of the things an eighteen year old needs to do is see what other countries are...

The Red Jockstrap

by Coxswain on Sep 14, 2017
Gay Male

This is a true story, as told to me by an Army buddy. The names, places, etc. have been changed. "Just keep your underwear on, son. Don't take off any more than that, and you'll stay out of trouble." My father told me that when I was seven or eight, when he caught my cousin and me "playing with each other." Never forgot that. Even in the years when I didn'...

Fishing with My Buddy

by Jbearisthe1 on Jan 29, 2019
Gay Male

Bruce was my neighbor, and basically my best friend. About ten years ago my wife and I moved in next door to Bruce and his wife. The women hit it off before we even unloaded the moving truck. That weekend, Bruce and his wife had us over for dinner. That's when I found out Bruce likes to hunt and fish just like I do. After a couple weeks, he invited me fishin...

Caught with a Wedgie

by marriedhubbi on Oct 8, 2019
Gay Male

I never knew that my straight-laced life could take such a turn. Until that day I thought my hidden life of masturbation would remain undiscovered forever. You see, I have an unusual way of masturbating. When my wife and kids are out of the house, I often head to the bedroom and strip to my underwear. I prop up a couple of pillows in the middle of the bed,...