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...

Behavior Modification Institute Ch. 12

by NancyPan on Sep 12, 2017
Fetish

I was back in my room after an exhausting day of training. The prostate stimulating butt plug had been removed. I longed for the sensations it had provided me, and I had asked Madam Christina to leave it in. She had only smiled and said, "So easy, so easy; but no I will not leave it in. You will have to earn the pleasure you have learned that your ass can pr...

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...

Finally Receiving

by 1mbibry on Feb 6, 2018
Loving Wives

Finally on the Receiving End For years I've fantasized about being pegged by my wife. Years ago I even bought a feeldoe and did my best to talk her into using it with me. She simply wasn't into it. It was awkward. I think she was worried that I was about to "come out." She didn't want to "be the man" in our relationship. So with that failure my desire was...

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...

Me and My Bullet - At The Mall

by KennyTurk on Sep 13, 2017
Exhibitionist & Voyeur

Ever since I can remember, I've been addicted to daring public adventures. What began with that natural teenage interest in seeing how much you could get away with has grown over the years into regular journeys out... journeys that start out quite ordinary but somehow always seem to turn into full scale panic-driven thrill seeking - the risk of being caught...

Strange Feelings

by ChrisLePaige on Sep 16, 2017
Transsexuals & Crossdressers

This is my first story about my life as a sissy. To be specific, it's the first story I'm writing for my Mistress knowing she is going to have me share it with the rest of the world. I've written plenty of journals, stories, and research papers for her, but always with the understanding that they were private, shared only between the two of us. Mistress rec...

Intimate Shower

by Siamese246 on Dec 12, 2018
Loving Wives

She grabs his hand as it heads down her tummy to her pussy. "Hold that thought" she says, getting out of bed "Come shower with me." Bemused he climbs out of bed and follows her to the shower. Turning on the shower and waiting for the water to get hot, he pulls her toward him for a kiss. His tongue invades her mouth, pushing against hers, probing, inquisitiv...

The Intellectual Pansexual Ch. 04

by PeterDeRuthyn on Jan 14, 2019
Exhibitionist & Voyeur

Taylor woke to the morning sun falling through the window on his face. Josh's body nestled against his, his morning wood tucked neatly between his roommate's thighs. He dragged one foot up the runner's bare leg, stroking him. Josh giggled. "Good morning, yourself," he mumbled, and rolled over to kiss his bedmate. Their swords crossed, making both of them sh...