Stories Of Women Milking Men's Prostate To Orgasm Stories

369,575 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Mrs. Swanson's Boarding House Ch. 07

by 0ra11yfix8ed on Sep 25, 2017
BDSM

Mrs. Swanson watches as her housekeeper instructs two candidates for the position of assistant housekeeper after the three young men and the three young ladies participated in the ceremonial first milking of Mrs. Morton's son Carl. "What do you think?" Mrs. Swanson asked her long time friend Sara Lee Morton. The two ladies were sitting in the parlor watch...

March Madness Ch. 06

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

A Glorious Hole

by bigdaddykingdavid on May 7, 2019
Fetish

I want to share something that I have experienced recently because it has enhanced my sexual pleasure tremendously. By accident I discovered a type of sex that is a variation of a common fetish and modified it to fit my preferences. Even in its basic form however there are several aspects involved that I believe most men and women will find arousing. The...

Enlarging Hubby Ch. 04

by Buffwriter on Sep 25, 2017
BDSM

So Much Semen *** Eric *** "Year?" I asked hesitatingly. "Oh, yes, enlarging Pat and Brian didn't happen overnight. That first quarter inch on Brian was easy, the rate of growth slowed down after that. I think we mostly stretched the ligaments in his penis out over those first weeks, letting more of his internal penis hang on the outside. His actual growt...

Jack and Jill Pt. 04: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

He looked in the mirror, clean shaven with blonde wig and full make up, he was unrecognisable to himself, his false eyelashes fluttered back at him, his shoulders, his hands and his Adam's apple all gave him away on close inspection, but from a distance he was passable as a woman. He couldn't believe he was doing this, he was terrified of going out in public...

The Clan Pt. 03

by Bullwip on Sep 14, 2020
Erotic Couplings

... She began to tug and squeeze at the root of him, generating a rich foamy lather in the process. His phallus expanded, filling her hands quickly, reaching out and upwards to nearly three times its flaccid length in less than a minute. It was the change in girth that impressed her, however, more so than the length. She mused briefly what it would be like t...

When Sara Met Bob Ch. 04

by yellowfrog on Sep 14, 2017
Fetish

PART IV: Sara sculpts Bob's lovely penis Days turned to weeks, weeks turned to months and Sara derived ever-growing joys from milking Bob's prostate. The implanted micro-devices gave Sara the ability to massage his prostate remotely, be it from a distance in the same room, to the other end of the bar at the shemales saloon they frequented often, and even ov...

The Versatile Student Ch. 01

by atlanticsexual on Sep 16, 2017
Fetish

My hands trembled as I opened the envelope - I read it - experiencing immense joy but also stressed out of my skin - I had been accepted to the UWO [University of Western Ontario] business school for their MBA program. So, I'll have to live in London Ontario for the next few years. Where will I stay? How can I afford it? I already had a student loan for my...

Dressed for Disaster: The Prequel

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

Dressed for Disaster: The Prequel Pat Summers put his suitcases on the bed, and made a quick survey of his room. He noted with approval the full-length mirror on the back of the closet door, and he poked his head into the bathroom to inspect the bathtub and vanity. Not overly luxurious, but they would do. First things first. He opened his computer case and...

Paradiso Ch. 08

by SlyKink on Sep 19, 2017
Transsexuals & Crossdressers

Day 2 Continued My head was buzzing with alcohol and anticipation as we walked back to our room; Sara, Jessie and I. I intentionally let myself fall behind a couple of steps so I could watch their asses sway from side to side as they walked. It was a lovely sight; Sara's toned body with its fair skin and dark hair flowing down her back and Jessie's curvaceo...