Gay High Heels Stories

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Orientation
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Infinite Scroll

Bottomed Out Ch. 02

by capresque on Sep 14, 2017
Gay Male

When I awoke, it was dark, but I couldn't tell what time it was. For a moment I couldn't remember what had happened and why my whole body was sore and sticky with fluids. I felt my arms and legs being released from the ropes holding me spread eagle on the bed. I was shoved off the bed onto the hard floor. With one slap on my ass I was reminded of all that ha...

The Hanky Code Pt. 16

by His_fag_wife on Sep 14, 2017
Gay Male

Melinda opened the door to a very large guy, not tall but fat almost round. He waddled in smiling and sweating profusely. He carried a large Gladstone bag giving him the air of an old fashioned Doctor. Mistress Caprice said "Welcome Mr Smotherer, I hope you're pleased with your pig." "Ohhhhh yes, she looks perfect, I really have worked up a sweat on the wa...

Caught, Blackmailed and Loving It! 002

by CSK on Sep 14, 2017
Gay Male

It's amazing how one day of laying out naked can change one's life. If you haven't read my first account of how my life changed, please read chapter one and then come back. If you have read it, you will know that it left off with me and Heather making out in a pool while her father (Mark) fucked me in my ass and his friend Jack fucked her in her ass. After t...

Hotel Night

by guy_manuel on Aug 18, 2017
Gay Male

It was my first time crossdressing. I have no gender identity issues or anything, I just wanted to try it. But I also wanted to have a little fun since I was sure this would be the only time I'd do something like this and I hadn't gotten laid in a while. It probably wasn't the smartest idea, but if literotica had taught me anything it was that Craigslist was...

True Love Found

by scrotus on Sep 25, 2017
Gay Male

Jeff and I had been hanging out for about six months. We didn't live together but we might as well have. We spent a lot of time together when we were able. I am a photographer and I frequently am on the road doing shoots. Jeff is an engineer and has to travel once or twice a month. When we found ourselves at home, we usually were together. We never planned...

Puff Adder Pt. 02

by anaidmap on Aug 18, 2017
Gay Male

Oliver "Meet me at the car park in five. I'm the red Shelby. Heading home early." Hmm, weird, An leaving school early? Wow, she hadn't bunked a class since high school… Maybe she couldn't wait to see me. I couldn't wait either, so I moved into a jog towards the car park with my phone still in my hand. When I made it there I couldn't help but laugh....

Decoy

by sr71plt on Aug 18, 2017
Gay Male

"That must be his plane now. Now, remember what you've been told about what your role is." Floris Bourek leaned back in the cushy backseat of the Lincoln MKT Town Car and turned to look directly at the Lebanese beauty sitting beside him. Jamila Maloof, model thin, with long, silky auburn hair, and light-brown, flawless skin, flashed her fluorescent-blue nail...

Rick Needed a Beer, Gets Much More Pt. 10

by Iwanttwo on Jul 31, 2019
Gay Male

"Sue, I like having a hairy body, I admit Tim looks really hot smooth, but I don't think that's for me." "You didn't want to put on the pink panties I got you last night, and ended up loving how you look in them, like a sexy cocksucker, didn't you? We are going to shave you, and then I have some really sexy things for you to wear." After arguing for a whil...

How Adam Became a Sissy Fuck Toy

by SlutFucker510 on Dec 2, 2019
Gay Male

For most of his life, Adam was your run of the mill straight guy. He was only attracted to women and when with a woman, he was always in the dominant role. He loved rough sex and being aggressive, even borderline abusive, to the girl he was fucking. He was proud to be a hard fucking, dominant, straight male. That is, of course, until he moved to San Francis...

From Alex to Lexi Ch. 03

by oskarwild on Sep 14, 2017
Gay Male

Awakening Lexi lay in bed with the morning sunlight streaming across his naked body. He was in the fetal position and he could see Max, his new Daddy, lying on his back next to him, sound asleep. Daddy's arm was over his head and Lexi could smell the pungent odor of Max's underarm. They had worked up quite a sweat last night before finally falling asleep....