Gay Shemale Surprise Stories

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Room Serviced Pt. 09

by bigblue212 on Jul 6, 2020
Gay Male

Knock, knock. Carson tapped on the bathroom door. "You ready?" Mr. Armisen asked. Carson didn't say a word. A short while later Armisen emerged from the bathroom, a white robe around his shoulders, a glass of wine in hand. His long, flaccid cock dangling from his hips like a sword. He furrowed his brow as he hobbled into the dimly-lit bedroom, his ankle...

Home Alone

by superglide52 on Aug 18, 2017
Gay Male

It was pretty much just another day at home. Sitting here surfing the internet. Normally I would be at work or out riding my Harley, but today I had the day off from work and wouldn't you know it was raining, so no riding today. My wife was at work today, so I couldn't even talk to her. I often rise early and surf the net, play games and stuff. It is just m...

Oral Friends Ch. 04

by oralfriend on Oct 13, 2017
Gay Male

Oral Friends Four – The Surprise The week after the big fishing trip was moving slowly for me. I found myself missing the companionship that the three of us had shared at the cabin. To be honest I was also missing the sexual excitement I had enjoyed too. I suppose it was the ability to do anything I wanted, within reason, and have it accepted enthusiastical...

Imprisonment Ch. 02

by AgentK on Oct 9, 2017
Gay Male

Friday morning came too early for Justin MacDowell, who looked the picture of misery as he sat working at his desk in his small office at the prison. He'd barely been able to sleep since Wednesday, when the warden had discovered he'd been skimming money from the sales of prisoners' belongings to auction houses. The only way he'd been able to keep his job, an...

Cleaning Day

by kudzu41999 on Aug 31, 2017
Gay Male

Gilbert called my parents and asked if I could come over to help him. He was an elderly retired gentlemen whom my parents had befriended at my church. Since I was desperately in need of spending money and Gilbert was so generous with my older brother, I consented. Spending time with elderly men was not something that appealed to me, but I convinced myself th...

House on Park Ch. 02

by sr71plt on Aug 17, 2017
Gay Male

Eric must have enjoyed the polishing job we'd done on the trunk of his Tempest, because when I'd finished shooting off into him, he said, "Well, Peter, if you'll get this beautiful body off mine and stop entertaining the neighbors, perhaps we should go in and shower." "I want to fuck again. I want you to fuck me," I said, without moving. "That's not out of...

First Time In Front of My Wife

by glmike523 on Sep 14, 2017
Gay Male

One of the best days I ever had with my wife, sexually that is, is when she watched me suck a cock for the first time. At the time we were married about 15 years and from the beginning she had always said to me she would like to see me with another guy. Little did she know that I actually craved to have sex with a man. Earlier in my life, before being marrie...

My Best Birthday Present

by showtime20042005 on Aug 18, 2017
Gay Male

"This is going to be the best birthday present you've ever had," Billy said, as he drained the last few drops of his coffee. I had been lamenting for weeks about the approach of my 40th birthday and Billy had taken me out for a birthday lunch to cheer me up. During lunch he kept hinting at a surprise birthday present, a present that would definitely involve...

Daddy's Little Nurse Ch. 02

by ElioV on Aug 22, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** It's been a few weeks and I am finally getting better. No more casts and my ankle is only a little sore still. But never mind that. I am still thinking about my son. He jacked me off. HE JACKED ME OFF. And I haven't even thought to do something for him until now. After he grad...

Cum Slut Ch. 02

by whbonney on Aug 28, 2017
Gay Male

After my first week of sucking cock, I sat back and thought about what I had done, and decided that I actually enjoyed it immensely and loved the taste of warm cum directly from it's source. So, the next thing I knew I had to do was become good at it. About two week later, the third guy that I had sucked wrote to me and we decided to meet again. This time h...