Gay Master Sissy Stories

3,801 results
Orientation
Length
Source
Infinite Scroll

Andre Finds Love Pt. 03

by eviltwin52 on Aug 18, 2017
Gay Male

See chapter 2 where my father-in-law fucks me while my wife is away on our honeymoon with her black lover. For those of you who wanted to know what happened to joanie in the final chapter of "It Could Be Worse", the mystery is solved. ***** Part 3: Tomorrow, I thought to myself happily. Lee Anne will be back tomorrow. And her black lover, Leshaun. I...

Master and Slave: The Meeting

by Harry_Ballsack on Aug 18, 2017
Gay Male

Please note: This is unofficially the first story in a series of stories about Slave and his meetings with Master. It was not a planned series, it just morphed into it. On to the story. The sub stood at the door, butterflies in his stomach. He has exchanged emails, and chatted and even talked a couple of times on the phone but now it was the moment of tru...

Coming to Terms

by HerLittlePiggy on Aug 18, 2017
Gay Male

I stood naked beside the bed. My hard cock jutted straight out from my body betraying my excitement. "I have never done this before," I said softly. "But it excites you doesn't it?" "I guess so," I answered as my cheeks flushed red with embarrassment. "You guess so? It's a yes or no question. Does it excite you?" "Yes," I replied honestly as I cast m...

The Joy of Submitting

by loneguy01 on Aug 21, 2019
Gay Male

I had recently answered an ad seeking a submissive cocksucker. I am a total bottom and had experimented with cross-dressing but never really got into the dom-sub thing. However, the ad intrigued me and I submitted myself to a hung black man in his hotel room. The experience was exhilarating and I yearned for more despite being apprehensive about the possible...

A Boy, a Daddy and two Tuxedos

by ThomasStevenson on May 21, 2019
Gay Male

"That suit makes u a horny little lad, doesn't it?" It was another text from Mr Matthews. Thomas was out at a bar with his co-workers, and he'd just sent Mr Matthews a picture of what he was wearing: a fine navy pinstripe three piece suit with a bright pink and blue striped tie and a lavish pocket square spilling out of his breast pocket. So Thomas texted...

Danny Darling Ch. 05

by bjmichaels on Sep 14, 2017
Gay Male

"UNBUTTON YOUR SHIRT AND OPEN YOUR SLACKS, YOU LITTLE WORM!!" she screamed in my ear. I stood there stunned; frozen in place. I couldn't believe the abrupt change in Mrs. Nelson's demeanor. The normally sweet, good-natured woman had never made even the slightest derogatory comment to me, and she certainly never raised her voice when she reprimanded me for...

Master and Slave - Meeting Again

by Harry_Ballsack on Oct 11, 2017
Gay Male

This is chapter 2 of an unofficial series of stories around a bi-curious guy that explores his submissive, panty and lingerie wearing side with a Dom that he met online. I hope you like it. * Here he was again, his palms were sweaty and his heart felt like it was beating 100 times a minute. The butterflies came back as he reached out and knocked on the...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...

Bringing Out the Sissy in Fred

by 0ra1Master on Aug 18, 2017
Gay Male

"Yessss.., ooh yesss, aahhh! yesss! That's it! Thaat's iit! God it feels good, so good! Ohh Sammy! Fuuck mmee! Yessss, yessss, fuuck, fuuck, yesss!" Mary Pats nails were digging into my shoulders; her ankles were hooked on my ass cheeks. I wasn't sure who was riding who but it was what it always was, a great fuck. "Give it to me Sammy! Harder...., h.a.r.d.e...

Curiosity Fucked the Straight Guy

by silkstockingslover on Sep 25, 2017
Gay Male

Editor's Note: this story contains incest content. NOTE 1: A special thank you to Estragon and Goamz86 for editing this lengthy multi-chaptered journey. Curiosity: Fucked the Straight Guy I can't explain for the life of me when I suddenly became curious. I mean I am 44 and have never found any man remotely attractive. Oh sure, I can tell when a man is goo...