Gay Prostate Milking Stories

5,088 results
Orientation
Length
Source
Infinite Scroll

Cupid's Sophomore Year, Semester 01

by xaviermayne on Sep 25, 2017
Gay Male

This story involves acts of both sex and romance between consenting adult males, so if that's not allowed where you live then you should march in the streets. I'm releasing this story under Creative Commons by-sa-nc license, which means you can do pretty much whatever you want with it, as long as you give me credit and don't use it for commercial purposes of...

Wild Flower Ch. 20

by vanalas on Feb 26, 2019
Gay Male

Comments, critiques and tips are welcome. Hello and welcome to this amazing chapter of Wild flower. Can Miguel fight for his justice while fighting for love? Will he ever get both in the end or will something else get in the way? Find out as Miguel's fight for love and justice continues in the all new "Wild Flower." Feel the passion... *** "What are you...

Let's Make a Deal

by MattyTanner on Mar 25, 2019
Gay Male

*The following account is based on a true story* *** "How about this? I'll make you a deal..." Oh great, Tyler's "deals" were usually nonsensical scenarios where both sides of the deal completely benefited himself. "If you let me have the good bedroom, I'll let you touch my dick." What? Holy shit, where did that come from? He really was drunk. Okay, I h...

Why: Long Night with Ben

by hasnoalias on Sep 16, 2017
Gay Male

All characters in this story are over the age of 18. ***** It had been four days since Dan and Ben had shown up at my apartment, followed by my friend Tim. I had seen Tim every day at school and spoken to him. He was getting better in dealing with what happened to him. He seemed less jumpy and far less depressed. I had been worried about him, for obvious r...

Breaking The Arrangement

by Web Dazell on Sep 17, 2017
Gay Male

My name is Web Dazell and there's a little history to go with this story. I began writing The Arrangement/Breaking the Arrangement back in 2002, posting each chapter on the ASSTR and Nifty websites as they were completed. What is posted below are all of the completed chapters of both stories combined into one. Other than combining the completed chapters, th...

Opposites Attract

by Pelaam on Nov 12, 2019
Gay Male

I walk indolently towards my new temporary workplace. I do not *have* to work, but I am good at what I do and so I take on the occasional placement; this one in a large software company. I will be one of their internal IT specialists. The company has Sales, Finance, Customer Service, HR; a full complement of areas where a faulty PC could cause big problems....

My Brother-in-Law Channing Duke

by perihelion on Sep 25, 2017
Gay Male

It started with the telephone call from Corinne at ten on a Sunday morning, morning for me but late afternoon in Baghdad where she was stationed as an army nurse. "Colin, is that you?" "Yeah, Corinne, I'm glad you called. I've been thinking a lot about you the last few days. You know; the twin connection. I figured something must be going on with you this...

Becoming Mark and Janet's Girly-Boy

by BuckyDuckman on Mar 30, 2020
Gay Male

Who knew taking your turn at washing the dishes could turn sexy? That's exactly how it started as Janet squirmed up close to me, wrapping her arms around me from behind and pressing her chest against my back. I might not have had hands on my back but I swore I could feel her stiff nipples poking me. "Hey baby?" she cooed, kissing the nape of my neck and se...

Her Brother Ch. 01

by tamgreen on Sep 25, 2017
Gay Male

My girlfriend had the sexiest mouth. Nice smooth lips, natural deep pink, full and soft with an impish little smirk lingering perpetually at the edges even when her expression was neutral. She also had gorgeous eyes - warm hazel with little flecks of green and gold. I thought I could die for those eyes. I was sure there was no butt in the world cuter than...

All Fools' Day Foolery

by sr71plt on Sep 14, 2017
Gay Male

[For an earlier story in the NYPD vice detective Mike Kavanagh series, see "Inevitable Case."] Mike Kavanagh stood at the French balcony window of his "seen better times" hotel on Canal Street, looking at the festival parade units forming below him, and then beyond to the western edge of the French Quarter. He was lucky to have found a residence hotel this...