My First Gay Prostate Orgasm Stories

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My Prostate & Me

by lord_jefe on Sep 18, 2017
Anal

Well, it all started about 20 years ago. I'm not sure if you know how tech support works. For me, I had either 10 calls or none. One day—I had 15. This is why tech support people burn out so fast. I had worked my ass off. I was tired, horny and had no girlfriend. So I went to a rental girlfriend place that I'd been to once or twice before. You walk in and t...

Call Me, Lover! Ch. 02

by twistedthoughts1978 on Sep 14, 2017
Transsexuals & Crossdressers

This is the second chapter of an ongoing fantasy. All people mentioned are 18 years of age or older. I recommend if you are just reading this that you read the previous chapter (Call me, lover.) to get the baseline. It has been almost a year since that Friday afternoon when my whole life changed. The year has flown by with how busy I have been. I had been...

Search for a Great Prostate Massage

by massageguy64 on May 29, 2018
Fetish

This story meanders a bit, through a number of experiences, but the end is a bit shocking. At least for me. This story, like all my stories comes from my personal experiences. Including the final one which was just this afternoon. All of the names and locations have been modified. ***** My first submission started with me standing outside an asian massage...

Massage What?

by MightyCasey on Sep 19, 2017
How To

How to initiate prostate massage into your relationship. This is what worked for me without a large amount of ass-pain, pardon my pun. I'm not obsessed with my prostate or anything, but it's nice to have a wife doesn't mind giving me an occasional prostate massage. My wife of twenty five years Gwendolyn is a real cutie, she has always been a great lover...

How to Buy a Sex Toy - FOR MEN

by Noira on Sep 25, 2017
How To

Author's note: This is for you, anonymous! You asked, you receive! Now you too can know just as much as I know about male masturbatory aids! — Fap... fap... fap... sigh... fap... fap... sigh... aw, is my poor little baby getting sick of using his hand to jerk off? I'm sorry to hear! What is that you say? You can't get laid? Awww. But that's okay! Because...

Not The First Time He Imagined

by super_chicken on Sep 13, 2017
Fetish

He was a 22-year old virgin. He hated it. He didn't know why girls didn't like him. But he had ideas. He couldn't understand why guys he knew who were even shier than him could get chicks. He could meet girls. He had friends who were girls. But he could never take it to the next step. He could never show his interest properly. Part of this was because he had...

How to Ejaculate Like a Young Man

by Whispor on Nov 26, 2019
How To

I've always been self-conscious about the size of my penis and testicles. I'm on the small-to-average size, but always been able to sexually satisfy all of my lovers. One aspect of my sexual function that I've always been personally proud of has been the volume and force of my ejaculations. The amount of semen I would produce can only be described as "copiou...

Domination by Tentacle

by SpagettiMaster on Sep 16, 2017
Sci-Fi & Fantasy

~Note: This is one of my idle fantasies while on a vacation. This content of this story is largely gay and prostate/cock sounding, so if you're not interested you can read another excellent story on this site :) Enjoy~ ***** I awake on my back feeling cold metal beneath me. It is not entirely uncomfortable, as the metal seems to curve around my body, leavi...

New World of Prostate Play

by awired50 on Sep 12, 2017
Toys & Masturbation

I come home from work and see that the package I ordered has arrived. It is in an nice case that could easily be slipped on a bookcase and look normal. I open the box and examine my new prostate device. The Aneros Vice. I put the batteries in the vibe and experiment with the nine different settings. The device itself is made of silicon and feels very nice....

Permanent Slavery Journey Ch. 06

by SubWes on Jul 13, 2020
BDSM

Upon owner's order what follows is the story of this slave's (age 60) path to permanent slavery. And the life, 7 years in May 2020, of slavery. Owner's Order: Write the story of your history with female domination. How it led to my taking permanent ownership of you. What your life of slavery has been. This one time you are released to be, and must be, tota...