Gay Shemale Mistress Stories

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A Naked Encounter

by Pissdrinker on Mar 6, 2018
Gay Male

Please note that although this is a true story, I have omitted that we used condoms, we always play safe. Despite whatever Lucy may tell you. ***************************************** Sometimes in winter, if we're not travelling, I go for long walks down the beach nearest to our house. Dave, my boyfriend, often stays at home but occasionally accompanies me...

Long Time, No Suck Ch. 04

by Stontstr on Sep 1, 2017
Gay Male

That weekend was amazing. I felt really great about my relationship with Marc. Cloe, Stephanie's girlfriend, turned out to also have a surprise. See, she turned out to have a rather nice penis, a nice extremely large, uncut penis. Cloe had even named it, Clarence. Marc had to go back to town on business for several days, but Stephanie said he knew all about...

An Unquenchable Thirst Pt. 01

by jam7227 on Aug 18, 2017
Gay Male

My story starts like most people's. I grew up in a home where you were told to act like a man. My father would often rant about how faggots were ungodly people doomed to hell. I was taught lusting after a man was the worst thing a male could do. I joined the Marines at seventeen; the manliest profession I could think of. I enlisted into the infantry and was...

My First Visit to a Gay Club

by girlboybootsie on Sep 14, 2017
Gay Male

One Friday night, feeling courageous I decide to do what I have long fantasized about, and go to a male sex club in San Francisco to lose my virginity. I slip on a pair of shiny pink silk bikini panties, which hug my tight buns and wrap a matching pink satin garter belt with lace trim around my waist. I then roll sheer white stockings with French backseams...

Never Mentioned Again

by sr71plt on Sep 14, 2017
Gay Male

"Shit, the way this snow is falling, I'm not getting my rocks off tonight." "Steady as she goes, Chuck. Lucky for us there are bars close to the ship. Let's try this one." Naval Petty Officer Three Ryan Stevens pushed open the door of the bar and ushered Naval Petty Officer Two Chuck Adams into a dimly lit bar, filled with smoke and with muted and fuzzy Co...

Bi-Curious to Cock Sucker

by osodd_boi on Aug 30, 2017
Gay Male

I looked forward to meeting Mistress D again, but wondered what it would be like. I had shared so many of my deepest fantasies and desire. Things that I wanted to experience but was also terrified would. Mid-morning I called Mistress D's phone and got her voice mail. I left a message that I would like to see her tonight if possible, and asked her to call me...

First Time with a Dominatrix

by WuLiMaster on Aug 18, 2017
Gay Male

I always found it interesting how total strangers could get into deep conversations while seated side by side on an airplane. I guess it's a way to pass the time, realizing that they will probably never meet again. The smooth looking man seated next to the attractive woman on the other side of the aisle was describing something and I wondered if he was spinn...

Society 1.2: Modernus Experiens

by TitianaPrisca on Sep 16, 2017
Gay Male

"Ah, alone at last, my darling Mistress Elena," Jacob teased flirtatiously once the last guest had left. Elena laughed and waved toward her boys. "Not quite, my darling Master Jacob. There is this pretty little toy that I'm eager to train." "Yes, little Jason. Handsome choice. And a star. I'd like to check out his folder again, beloved." Jacob thanked Sien...

This Thing Called Life Ch. 05

by noodneighbor on Sep 14, 2017
Gay Male

The ride back from the frat to the hotel was a whirlwind of information and feelings. The ladies were celebrating my first job and saying how well I did though Ashley teased that she missed my "tits" which were now sitting in the back of our vehicle. Flavia, pressed against me in the back seat suggested she liked me both ways just fine, which I enjoyed until...

Made A Man(In And)Out Of Me Ch. 03

by Cicero6 on Aug 18, 2017
Gay Male

Chapter 3: The Auction Within minutes of Kelly's request, she was again sound asleep as though she was completely comfortable with the idea we were to confess. I shut the blinds to prolong the night and still could not sleep. At some point I faded and did not awaken until noon. Kelly was up and dressed before romping onto the bed. I quickly pulled the sheet...