Prostate Cum Stories

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Cock Caged for the Weekend

by English_peter on Jun 26, 2019
Fetish

We had been living together now for some months since I had awakened a new sexual side to Susan. She had let me try all sorts of positions and kinkiness but now it seemed that she had decided that it was her turn to take charge. It was Saturday morning and we had planned to go to the local shopping centre mainly because Susan had a private appointment at an...

Medical Exam

by JWalker7 on Sep 14, 2017
Transsexuals & Crossdressers

I'd just finished my second interview for a new job and now it was time for a physical. I was nervous, really nervous because I knew that I was going to have to have a prostate check. My biggest fear was what would happen if I got an erection during the exam? And what if it was a male doctor? All these thoughts where going through my head. I didn't want to e...

The Visit Ch. 05

by stateofdenial on Sep 14, 2017
Fetish

He had not heard from his Mistress all week and began to wonder. Plus, he had not heard from Tweets until he got a message around dinner time to come over and clean up. As usual he undressed and went to work like every time before this one. Half way through she had him stop so she could get her obligatory orgasm from him and then milk his prostate as he was...

Satisfaction

by Houstonrn on Sep 13, 2017
Anal

I winced as the tip of the very realistic dildoe pressed against the opening of my ass. Twelve inches long and almost two inches in diameter this was the largest object I had ever attempted to experience anally. Even though the fake cock was greased, and I had already used my fingers to stretch the anal opening, its entry was difficult. Inward then back out;...

Locked

by NoFearGenderqueer on Aug 21, 2018
Transsexuals & Crossdressers

This is the single worst thing that has happened to anyone ever. This is the single most terrible thing that could conceivably ever happen. These were the first thoughts Tommy had after he saw the key to his chastity device disappear down the sink. He had only put them there for a second. He thought that they would be perfectly safe sitting on the side. He h...

Laura's Femdom Empowerment Ch. 04

by Long2bLocked on Jan 15, 2019
BDSM

Chapter 4 Going Pro It was late January and I decided it was time for some new excitement. I had broken up with Jared a few months prior and I wanted a new sub guy to torment. I was thinking about the best place to find a submissive guy and suddenly I remembered Leesa looking for costumes the previous Halloween. She wanted me to go to the party as a domin...

Hotel Panty Slave Pt. 01

by hotelpantyslave on Sep 16, 2017
Fetish

As a traveling consultant, I have found fun ways to indulge my fetishes while on the road. Because I stay at the same hotel for 12-18 months at a time I can leave a bag there with my favorite clothes and toys which means I don't have to take them through airport security every week or risk my wife finding them. Although my fetishes are not that wild, she has...

Five Positions Two Loads

by lynntg0444 on Oct 21, 2019
Transgender & Crossdressers

It took six months from my first blood test until surgery was prescribed. Unfortunately this was only a slightly feminizing surgery - I was diagnosed with prostate cancer, and the simplest solution was a radical removal of the whole organ. Needless to say, this was extremely depressing as I had become accustomed to mind-blowing orgasms through prostate stimu...

A Virginal Challenge

by HeroFizzer on Jan 7, 2018
Transsexuals & Crossdressers

"I keep telling you Jason, no." "But I've been asking for months!" "No!" "Please? I always wanted to pop someone's cherry!" "I swear to god-" "C'mon, Mary, we've been going out for five months now, it's not that big a deal!" Jason and Mary walk the busy sidewalks of This City at night, having just finished dinner. Mary sighs as Jason continues to plead...

Solo Stud

by Guy521 on Feb 26, 2019
Toys & Masturbation

His semi hard cock strains against the fabric of his tight gym shorts. He strokes his cock through the thin fabric and whimpers as his sensitive rod grows to full length. Standing up, he removes all his clothes. He brings the sweaty crotch of his shorts to his nose and inhales the masculine juices that has soaked the fabric. His cock is rock hard now. Glanci...