Gay Prostate Stories

30,137 results
Orientation
Length
Source
Infinite Scroll

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Roommate Dress-Up

by silkstockingslover on Oct 26, 2020
Transgender & Crossdressers

Summary: Straight guy is feminized by female beauty. Note 1: This story is dedicated to the real Mike who requested this story. Note 2: This is a 2020 Halloween Contest Story so please vote. Note 3: Thanks to Tex Beethoven and Robert for editing this story. Roommate Dress-Up "Shit," I sighed, as I saw my outfit for the wedding... I should have guessed s...

Why I Crossdress!

by readtaboo on Dec 12, 2018
Transgender & Crossdressers

Oh thank god! I hadn't heard from from him in three days and was beginning to think I'd blindsided and lost him altogether. When the phone rang, I lowered my voice to a whisper, "Patrick?...I'm home...yeah, I'd like to see you too!" More than you know. We simultaneously decided that mixing a quick drink was the single greatest idea either of us had conceiv...

The Molly Virus Ch. 03

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

*Jeri... I still got a few looks as I came in from the cab and to my room. Word seemed to have spread a little about me and my transition. The few looks I got were more dumbfounded and not getting it instead of like hateful and I'm pretty sure there were eyes on my ass as I went up the stairs to my room. Jack's there listening to music on his headphones lo...

Chip Wendy Dan Nancy Carl - Story 01

by BrokenPenis on Jan 6, 2018
Transsexuals & Crossdressers

Chip was a lonely nerdy mechanical engineer, about 33 years old. Looked like he could be Matt Damon's younger brother. Lived in his own home in a nice development. Had no wife, no kids. To the right side, there was a couple, Carl and Nancy. Just behind his house, was Daniel and Wendy. Most of the rest of the neighborhood was in their 60s or older and did not...

Gaping Young Black Wife on Beach

by Alluring_Crimson_Shifter on Sep 26, 2017
Anal

A good looking straight young black couple from Dearborn, Michigan decided to go to the beach for the weekend, just to get away from it all and relax. Avery said, "Let's go up to Otter Creek Beach near Sleeping Bear Dunes National Lakeshore. It is near a ghost town by the name of Aral. We can catch some rays and then do some exploring. It is only a couple...

The Intellectual Pansexual Ch. 05

by PeterDeRuthyn on Jan 15, 2019
Group Sex

"That was intense," Taylor said. "But I felt so fucking sexy." "You look it," Josh agreed. "And trust me, the benefits to your sex life are going to be amazing." The two boys were leaving their morning yoga class, Taylor's first. Skin-tight tank tops and tights clung to their lean bodies. Taylor had had to borrow a pair from Esteban, which made them look e...

Not Gay, Butt... Ch. 04

by Sacanaz on Sep 19, 2017
Group Sex

Time 4 Ron and Jessica had become more and more sexually adventuresome in the past couple of months, each trying to please the other with new and exciting ideas. They had finally bought and tried a strap on for Jessie, and they had tried myriad positions and situations. On this particular evening Jessica had a big surprise for her husband. She talked h...

My Warrior Returns

by sarah_siddons on Sep 3, 2017
Erotic Couplings

In the previous chapter When a picture isn't good enough you finally learnt of my love for Izzy and how I was left crying on the steps waving her goodbye. This may be the last episode in this series since I'm within six months of coming up to date. Again many thanks to all those offering encouragement. * With Izzy gone, my life felt empty so, 'booting-up'...

Foreplay Gets Erotic Role Play

by Alluring_Crimson_Shifter on Sep 14, 2017
Anal

"Hi Denise, you are looking pretty today. I could swear you look prettier every day, but that would be impossible," said her friend Francis another teacher. "Oh thank you Francis, I do try to take care of myself." "So what do you do in your off-time. Surely you don't grade papers all night?" Francis liked her friend and wanted to know more about her, maybe...