Gay Prostate Milking Stories

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The Male Room

by WatchingAndWaiting on Aug 18, 2017
Gay Male

This is the story of my first time with a man. And my last time... So far. I was always curious, even when I was very young. Looking at men in magazines, especially if they were in revealing underwear and had big, well-defined bulges. I had messed around a little as a kid, but nothing more serious than 'you show me yours and I'll show you mine'. But as the y...

I Love New York Ch. 01

by PeterPanics on Aug 18, 2017
Gay Male

With a long sigh I zipped up the last of my luggage. Four hours of packing and two massive suitcases later, I was finally done. Looking around my now empty apartment, I felt a little empty knowing that my time in California was through. Time for another ending, I suppose. I had to remind myself, as I hoisted the giant bags onto my bed, that I was chasing m...

Free Your Mind

by bi golly on Aug 18, 2017
Gay Male

I knelt on the floor before him, naked. His pants were open, his cock was full but not hard. I scooped up his balls in my right hand, his cock in my left and ran my tongue under the velvet head. I slipped it into my mouth, sucking a little, lapping a little. How had I gotten here? I was in the mega bookstore and the books about sex were just around the corn...

Mindless

by iSublime on Aug 18, 2017
Gay Male

Imagine a large dark room filled with entrancing electronic music punctuated by flashing lights. Deep bass throbs in the ear. On the dance floor a meadow of arms and legs sway in the audio breeze, and despite ample air-conditioning the atmosphere is rich with sweat and sex. Somewhere in that primordial sea of bodies I dance. Topless, sweaty, and with what I'...

From Gay Husband to Slave Pt. 01

by assguzzler on Apr 3, 2019
Gay Male

My husband Winston and I were married when I was twenty two and he was thirty. I told him of my submissive fantasies and he role-played with me some at the beginning of our marriage but for the most part he showed little interest in D&S or Domination. We had a good marriage but we often fought as we both tried to dominate the other when it came to who would...

Manly Persuasion Ch. 01

by Ryan Carlyle on Apr 3, 2018
Gay Male

Author's Note -- Dedication - To JC, with heartfelt thanks. This is YOUR story. You asked me to write it and I did. So, my friend, this is for you. ### Prologue ### A cool stream of air blew across the back of my neck. Seconds later, his lips were close to my ear. "Are you ready?" I didn't answer. "Are you sure you want it?" Was I sure? I mean . . ....

Austin's First Time

by Lovetolisten on Sep 14, 2017
Gay Male

Austin and I have been friends forever. We talk about anything and everything. I talk to him about failed dates and he tells me about his most recent conquest. Ours is a friendship born of an awkward attempt at something deeper that just didn't work out. But even the best of friends have secrets. He knows most of mine... including my darker side that sends...

Banging a College Boy

by mstrhole on Aug 18, 2017
Gay Male

I usually leave the "young stuff" alone. And I don't mean jailbait. I'm no chicken hawk. It's just that I generally prefer guys closer to my age. Call it a comfort thing. But one night I was out of town and cruising Squirt and this 20-something college boy messaged me: "Hey Daddy ...'sup?" I would ordinarily ignore an opening line like this, but I was really...

Derek Pt. 03

by TAHammer on Apr 27, 2020
Gay Male

Everybody was decked out in cowboy boots, jeans, and bandannas at the afternoon barbecue. Of course, Derek with his sleeveless button-up shirt, tight jeans (with a big buckle belt), and cowboy boots looked like the Playgirl cover model for the cowboys issue. Everyone watched him swagger around the patio. Karen gave him a cowboy hat, and every gay guy and str...

Cramp

by MirageLM on Aug 30, 2017
Gay Male

NOTE: Just a fantasy. Just for fun. Everyone is of age. Everyone is consenting. Anatomical details may not be exactly correct. Just enjoy it, okay? ***** You're on a business trip and after a long day decide to use the hotel exercise room just to wind down. You change into a pair of shorts, a tee, and your gym shoes and take the stairs down to the room jus...