Gay Shemale Mistress Stories

370 results
Orientation
Length
Source
Infinite Scroll

Three Strikes Ch. 07

by Mrsgnomie on Oct 8, 2018
Gay Male

I knew I wasn't going to see Shane on Saturday or Sunday since we hadn't made plans and he didn't have my phone number. That was the gamble when playing hard-to-get. Sometimes you're actually hard to get. Sure, there was a part of me that hoped he'd get my number from Drew and call me, but he didn't. We'd probably see each other Monday between practices, an...

The Intern

by markindy on Aug 18, 2017
Gay Male

This story is primarily about man-to-man sex, but it does feature an MMF episode. Just a "heads-up" for those who prefer gay-only stories. The Intern ++++++++++++++++++++++ My sex life was ok, but stagnant. Over a year after my divorce, I still hadn't found another woman I felt I could have a long-term relationship with. I loved my ex-wife very much, and...

Kiss the Darkness Ch. 06

by Chancem77 on Mar 16, 2020
Gay Male

Brother Neil held the lantern high so that Christian and Alexander could see through the thick darkness that covered the monastery grounds. He led them to a small cottage within the courtyard behind the gardens. "The guest house has already been cleaned and made ready." He smiled at the couple. "Breakfast will be served in the main hall at sun up. I've taken...

Bittersweet Irish Cream Ch. 06

by Kabba118 on Mar 30, 2020
Gay Male

Trigger warning: It gets intense as there is talk of rape and sodomy, and murder in the next two chapters. I PROMISE it ends in a happy ending for these two, they just have to get there. Thank you for those who are hanging in there so far, showing them love through your votes and comments. If you are starting here in Chapter 6 you missed their whole love sto...

His True Self

by readandreact on Sep 14, 2017
Gay Male

Note: While the name of the protagonist is the same, this story is not a sequel or prequel to my story Virgin No More. It's much closer to the truth of my actual first time than the other though. I parked my car in the driveway with a slight sense of resignation, not wanting to be here. I was at my former co-worker Donald's place for dinner, agreed to in a...

Wrangler Butts Ch. 02

by reddirtwriter on Sep 25, 2017
Gay Male

Darrin drifted awake as the early morning light shifted through the uncovered window. He ran through the events of the previous evening, smiling as he felt the slight tug of the dried semen on his chest hair. Luxuriating in his memory, the realization came that he was alone in the bed. Cautiously walking from the bedroom, Darrin called out softly, "Mitch?" P...

An English Boy Gets Turned Out Ch. 02

by RustyRover on Sep 14, 2017
Gay Male

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous di...

To Our New Applicant

by thick1191 on Sep 24, 2019
Gay Male

To our new Applicant—After You've applied You're reading this introduction because you've self-identified yourself to us in writing, as a prospective Club cocksucker. We have furnished this writing so that you can ruminate on your prospects before your scheduled interview meeting. You need to understand that at your interview meeting this script will be fol...

Kiss the Darkness Ch. 07

by Chancem77 on Mar 16, 2020
Gay Male

A vengeful heart "The night falls without a sound, cold and alone are we. The light for which you sacrifice yourself flares once, then dies, devoured by the all-encompassing darkness All hope must sicken and fade. My soul thrives no more. How could you abandon me? Demons surround us, crying, we have lost our way." ___________________________________...

Speech and Debate Pt. 07

by DAMackey on Sep 25, 2017
Gay Male

When my eyes opened on the morning after my first workout session with Daniel, I wondered if I had been transported to some kind of medieval torture chamber while I slumbered. Or if the Black Death had made a sudden come back and ravaged my body overnight. Maybe small pox? Or Polio? I was engrossed in a pain the likes of which I had never experienced, neve...