Gay Sissy Anal Stories

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Bicyclist Champion Lingerie Secrets

by Alluring_Crimson_Shifter on Jan 16, 2019
Gay Male

Eric was riding very fast hoping no one would notice what he was wearing for a racing jersey. His jersey though colorful, was actually lingerie so light it breathed well and was virtually transparent. He did not plan on stopping so nobody could see he was practically naked. At least while he was in the riding position you could not see his cock and balls. He...

Packing in Tight Places Ch. 02

by drmweaver705 on Jun 8, 2020
Gay Male

All participants are over 18. I entered the code to unlock the door to the storage warehouse with trembling fingers and not a little trepidation. After all, strange as it may seem, the last time I was here, a week ago, I was taken roughly from behind. My anal cherry had been popped by a man whose face I had never seen. I came twice from this man's violation...

Nephew's Readjustment Pt. 14

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas week began with a morning session with his new plastic lover. While the bathroom made things easiest if he was willing to work, morning wood wasn'...

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...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

My New Daddy Ch. 03

by sissytoy20 on Mar 6, 2018
Gay Male

The buttplug that Sam had unceremoniously forced inside my tight asscunt had hurt like hell, but I'd enjoyed the feeling of being forced open with no warning. The little, pink butt plug wasn't very large, but it had felt like a giant donkey dick in my ass. It had flashed by in Sam's hand so quickly, maybe it was larger than I thought. It felt huge in my butt...

Sissy con carne

by WinterBreeze on Sep 26, 2017
Gay

You've always known inside that you we're far less heterosexual than everyone might think. It's been a long time since you imagined you were the man getting sucked and fucked in the porn you watch you can't help but imagine taking delicious juicy cock into your mouth and even your ass you'd love to feel these pleasures for real. Luckily fortune seems to be i...

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Job Evaluation -The Christmas Party

by VeryCuriousIan on Mar 18, 2020
Gay Male

It was now over a month since Ian's last disciplinary problem and he had at long last got his act together. He was now one of the best employees in the office. Even Carol, his hated line manager, had to admit he had turned over a new leaf. Although she still loved to call him a little cocksucker anytime she could to cause him maximum embarrassment. Ian's...

Demographics

by male_sharmota on Sep 16, 2017
Gay Male

I woke up a bit before sunrise and climbed down the ladder of my bunk bed. My roommate laid sleeping in the bottom bunk next to my wife. I looked at myself in the mirror on the wall. My middle-aged body was still in good shape. The legs, ass, and chest were well shaved to provide a clear view of my smooth white skin. So was my face. My neatly trimmed bush lo...

Nephew's Readjustment Pt. 15

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas was able to refrain from masturbating that night and the next morning, but only because of the tenderness of his ass. Without access to his genita...