Prostate Orgasm Stories

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Crossdresser's First Anal Orgasm

by ksha on Sep 16, 2017
Anal

A young man still experimenting with his body, found a new fetish he enjoyed quite a lot. He found the joys of anal masturbation. He had heard rumours of an orgasm so wonderful it would leave you shaking afterwards. He was in search of his very first prostate orgasm. This is the story of the first time this young man would discover the joys of prostate pleas...

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 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...

Vacuuming Is Fun

by dooboige on Sep 18, 2017
Toys & Masturbation

"One of my chores in my house is vacuuming. My wife does the dusting, and other such things, and I follow her around with the vacuum. Sometimes, I'll instead do the vacuuming the next day, especially if I'm planning to work at home and we're cleaning late. Some years ago, I read a story---maybe it was in My Secret Garden---about a woman who did her househo...

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...

First Multiple Sissygasm Today

by JessC on Sep 16, 2017
Transsexuals & Crossdressers

I had my very first multiple sissygasm. I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice la...

Sex Shop

by rampe on Mar 18, 2020
Fetish

I am a single guy about forty years old. I don't have regular sex contacts so I often masturbate. Sometimes I like to have something extra in my solo games. I have bought some accessories like lube, gloves and anal toys. My ultimate goal is to have a prostate orgasm which I never have had. I have a few prostate toys and they feel good but orgasm without to...

The Photographer's Trap Ch. 02

by ElizzyViolet on Jun 25, 2019
Transgender & Crossdressers

Elizabeth here; lots of people wanted another one, so this is the second part of "The Photographer's Trap". Reading the first part is probably a good idea. You'll see some toys and butt stuff in this one, unlike in the previous. Happy reading! ~~~~~ ~~~~~ Since that Saturday morning, Timothy started to find himself wearing panties underneath his ordinary c...

Special Massage

by Doctor O on Sep 25, 2017
Erotic Couplings

"Hey, Missy, this is Steve." "Hi, Steve. Need to schedule an appointment?" "Yeah, I'm really tied up in knots," was the reply. "Any chance you can see me this afternoon?" "Yeah, I have an opening at 3:30, will that work for you?" "No, sorry. I've got a client coming in then. O...K...well, maybe I can catch you next week. I'm pretty busy. Tell you what; I...

Cowper's Gland (The Ultimate Lube)

by jasliz on Sep 15, 2017
BDSM

My wife is very kinky; I'll say that right now. She likes dominating me and teasing my body until I scream for release. She says it's for research... her own. Since she calls it research she institutes 'controls', basically the controls are me tied up so I can't touch her or myself. She made me set up a table in the basement with padded straps for my wrists...