Gay Sissy Cheerleader Stories

955 results
Orientation
Length
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Infinite Scroll

The Talent Scout

by eviltwin52 on Jun 5, 2019
Gay Male

The day I first met him was like any other day. Riding the Metro to work I was suddenly jostled out of my reverie by some one bumping into me from the back. Turning I found myself looking up at a ruggedly handsome man. His steely grey/blues seemed to pierce into my very being. I wanted to look away but was unable to do so. After a few seconds that seemed to...

A Kept Sissy Boy

by keptsissy on Sep 19, 2017
Gay Male

"You need your butt paddled, don't you?" When I responded to his 'Dominant Male' ad I knew what I wanted, what I might be in for. I masturbate to nothing other than being used by a real man. But I didn't know this man would exploit that completely at the time, be as good at it, as addictive as he is, make me his full time sissy 'girl'. It started out two...

Stick Shift: C.S.P.

by zackjack on Sep 14, 2017
Gay Male

I watched, rigid dick in hand, as the smaller man squatted in front of the handsome stud who hit the vape cig between his fingers in obvious expectancy of some good head. Both men's ebony skin aided their blending into the shadows which added to the mystique of my visual. The diminutive dicksucker knew his way around dicks in general and this 'cocksucker pa...

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...

My New Daddy Ch. 01

by sissytoy20 on Feb 13, 2018
Gay Male

I'm 21 years old and I attend college but I still live at home for financial reasons. I've always been fem and young-looking for my age. I like to cross dress, but I don't usually dress fem in public. I've just found that it can be difficult for some straight folks to take a young male who likes to be a sissy slut. So you can imagine my surprise when I was r...

It Could Be Worse Ch. 06

by eviltwin52 on Sep 14, 2017
Gay Male

In chapter 5 Leon took control of what he called his new sissy and fucked Cin into submission. We both became addicted to his superior black cock. Besides falling for his cock, Leon's predatory nature was evident. He wants Cin and I to prostitute ourselves for him. In the throes of black cock lust, we agreed. It could be worse Part 6 "Did you remember t...

I Turned Myself Out Ch. 04

by drmweaver705 on Sep 14, 2020
Gay Male

All characters are over 18. This story contains bisexual and cuckolding activity as well as fetishistic name-calling. If you don't enjoy these things, this might not be the story for you. *** Porn seduced me early in life and, even as a married man, it commands part of my loyalty to this day. It happened that I became bored, or maybe just desensitized, to...

Fantasy Out Of Control

by gbr2004 on Aug 18, 2017
Gay Male

I'm a divorced man living in Las Vegas. Recently retired, live alone and live a relatively normal life. I'm in decent shape for my age, 5'8", 180, and stocky build. I have been straight for the majority of my life. For the last few years, I have started to think more about getting together with another man. It goes beyond just this, as I want to be submissiv...

Beauty and the Beast Pt. 01

by Suzzique on Dec 17, 2017
Gay Male

I hesitated a long time before I advertised on Craig's list. I was 18 and had left school two months before. I had a place at university for the following October, almost a year ahead. I was living at home and had a mindless temporary job in a solicitor's office that made no demands on anything but my time. I'm a very shy person and no one knew I was gay exc...

Fraternity Slut

by oskarwild on Sep 14, 2017
Gay Male

College was great! High school sucked. And Sam was glad to leave it behind. He had been an awkward boy in high school. Short and skinny - only five-six and a hundred ten pounds - and pimply-faced, he had never been able to attract the hot girls that the jocks were able to get. But things began to change when he hit his eighteenth birthday shortly after gradu...