Gay Prostate Stories

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Husband's Transformation Ch. 02

by Prematurelimphubby on Jul 3, 2019
Transgender & Crossdressers

Brett woke up the next day with the sun shining in through their bedroom noticing his wife wasn't in the room with him. He stepped out of bed, put his panties from last night on and walked downstairs for coffee. He saw a note on the counter. "Good morning Britt, I had to run and get a few things from the office. I should be home soon. Take a relaxing ba...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

Picking an Indy Car Girl in Club

by unique_cabelas on Aug 20, 2018
Transsexuals & Crossdressers

Sam has a little secret, he does not mind getting some of the shemale cock. After a night out with the lads he disappears from the group down the road to a gay night club. Sam has never been in a gay night club and feels a little out of his depth. He has had a few drinks so is feeling relax and sits down scoping out the club. Looking around the club his eyes...

Diane Milking Sean Ch. 02

by stacey_lynne on Sep 25, 2017
Fetish

Needless to say Diane's panties became my most prized possession. Working all day, very successfully now, if I may brag, I looked forward every evening to come home, take our her panties, and masturbate. No matter what I did, how I did it, nor where I did it, the pleasure was never as intense as it had been when Diane had milked me. The few girls I dated w...

The Alpha Who Made Me a Sissy Ch. 01

by HB77 on Jul 31, 2019
Transgender & Crossdressers

So there I was again on all fours in his bed. My peach coloured thong panties pulled to the side, and my daddy behind me with one hand on my hip and the other Gripped onto the back of my red corset. Chad relentlessly filling my ass pussy with his gorgeous rock hard 8" as I moaned "oh daddy, oh daddy don't ever stop fucking me, I love you" over and over in my...

The Lawn Rangers Ch. 10

by texaswade on Sep 14, 2017
Group Sex

My girlfriend Claudia had called me and my best friend out. We'd been having gay sex for several months in secret. In an effort to get Claudia and her twin sister to fuck each other, we agreed to have sex in front of her. Apparently our enthusiastic fuck gave away our secret. John and I looked at each other in dismay. "What are you talking about?" John a...

The Captain

by fuckwriter123 on Sep 16, 2017
Anal

I've been playing rugby ever since I was a kid and now that I've just started University I've joined their team. I've been to a few of the sessions and am starting to get to know the guys on the team. The team captain is a big guy called Joseph, but a lot of people just call him Joe. "Right guys lets finish there, hit the showers," our coach said. He in hi...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

Paradiso Ch. 10

by SlyKink on Sep 19, 2017
Fetish

Day 3 Continued Sara and I arrived at the spa a half an hour after leaving our room. It was still early and there weren't many people out in public fucking just yet, even though it was shaping up to be a beautiful day. We stopped only once to watch a foursome consisting of two men and two women, none of whom wore anklets. One pair was going at it missionary...

Becoming More Feminine Pt. 02

by bottumguy84 on Feb 11, 2019
Transgender & Crossdressers

(Editor's note: This one isn't as long as my last story, the main character is getting a first name, and I'm going to incorporate a few requests from readers in the last story) *** Jason, Dan we're back. I barely was able to open my eyes when I heard Jen say, "Dan"? I finally woke up enough to realize what happen, Jason's arm was draped around my waist an...