Prostate Milking Stories

30,157 results
Orientation
Length
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Infinite Scroll

The Deal Sammy Made for Rent

by TheLastBrothelontheLeft on Mar 2, 2020
Fetish

Whimpers escaped his lips. In between, he breathed in air in gasps and moans. Each one muffled by the pillow that his face was buried into. Behind him sat a beautiful person. A pair of hands gloved in white latex. They had slender effeminate facial features. Their body was lean and muscular. They seemed almost ethereal, bathed in the dim light of the bedroom...

Milked By Three

by Kessler on Sep 18, 2017
Fetish

Linds and I were addicted to this newfound fetish called Milking. I think she gets into it more than I do. In fact I know she does. Her friend Joan turned us on to it and since that day Linds has been milking me as often as possible, sometimes three times a day. Several months had passed since my initiation when Linds approached me with a wonderful opportuni...

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...

Mommy's Gentlest Touch

by milkydreaming51 on Oct 30, 2018
Erotic Couplings

I make my way exhaustedly into the house. It's been a long day at college classes and things aren't getting much better for me below the belt. I stumble into the living room, dropping my bag as I do, and kicking my shoes off. That's when I see a woman waiting on the couch with her legs crossed staring directly at me. She's Columbian, average height, not sk...

My First Milking

by Bakeboss on Sep 13, 2017
Fetish

When Mistress first put me into chastity, she said it was for a trail period. She soon found out it not only keeps me from abusing my worm while she is out it also keeps me more attentive to her needs. Another plus was that now I had to sit to pee, I have always had to relieve myself this way while Mistress was around, but she suspected when she was away I d...

FemCon 2048 Ch. 01: The Pegging Seminar

by shankinauthor on Dec 24, 2019
Fetish

Note: All characters featured in this story are over 21 years of age or older. Note 2: Thank you to blackstallion21 for helping me edit. FemCon 2048: The Pegging Seminar ~Background~ Every 3 years in mid fall, a female domination convention is held in a major city in the United States. A few decades back most cities would feature protests against this k...

Me And My Online Master

by ftpmike1980 on Sep 16, 2017
Letters & Transcripts

This was a chat with my master. Online Master: Hello, lad. Hope you are being a good boy, Michael. Michael: I am doing well. Hope you are doing well. Online Master: Glad to hear you are doing well, Michael. I am also. Let me know when you are ready to play again on cam, lad Michael: ok. sorry we haven't been able to meet up online. i've been busy with...

Wife Re-Trains Her Husband!

by Freakboy80 on Sep 12, 2017
Loving Wives

Tim and Nancy had been married for over ten years. Tim was a construction worker and Nancy was a nurse. For the first few years of marriage everything was great, but as time went on Tim became more and more unhappy in their relationship, and started becoming aggressive towards Nancy. On a few occasions Tim, in a fit of rage hit Nancy! Tim was a "mans man" ki...

Mistress Milks My Prostate

by cainuseeme1980 on Sep 14, 2017
BDSM

We arrived at dinner for some relaxation time. Mistress has enjoyed a good week and was looking forward to a nice glass of wine. I should explain that my mistress enjoys tease and deny, being her favorite games. She usually enjoys 10-12 hours of it and then finds great pleasure watching the huge load my cock releases for her, but this week she enjoyed the...

Dominating my Husband!!

by johnemerson30 on Sep 18, 2017
BDSM

I dominate my husband with prostate milkings and strap-on discipline!!!!!! Now that that's out of the way, a little background information on how we got to this point in our lives. I am not your typical leather-clad dominatrix that you see on TV. As far as I'm concerned, all that leather is just for show! I am your typical normal, unassuming housewife tha...