Prostate Massage Stories

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Robert's Yearly Exam

by dudpar on Sep 14, 2017
Anal

I have to endure a yearly prostate exam since I've been 48 years old; this is my fantasy of how a prostate exam should be given. Ok, I have been putting it off for about two weeks; I'm just was having a very difficult time bringing my self to call Dr. Steins office for my annual prostate exam. Maybe the doctor's name will give you some idea about how much f...

Intro to a Dream Made Real

by Phallicphun on Sep 15, 2017
Transsexuals & Crossdressers

Jim had known growing up that he enjoyed bi-sexuality. But he had never found a man attractive the way women were to him. For example, he never found himself wanting to kiss a man, but he liked holding a hard cock as much as he enjoyed touching a wet pussy. He really enjoyed sucking a dick as much as he loved licking a hot hard clit. After moving to a new...

Mistress Jones Ch. 02

by TF2123 on Sep 25, 2017
Fetish

Tuesday went by way too slowly. I was really looking forward to my exam at the nurse's office. Miss Jones wasn't only a science teacher, but she was also the head nurse of the school. The four school nurses were three very attractive young teachers and the school's receptionist, who was a plump woman in her mid-40's, yet still very pretty. I had only been to...

Trip to the Doctor's

by BaldAndNerdy on Sep 12, 2017
Erotic Couplings

Note to readers: This is my first attempt at an erotic story. I would love to hear any and all comments (positive and negative), just as long as they aren't blatant bashing. All characters are over the age of 18 and any similarities to real life people is completely coincidental. So now, I hope you enjoy. _______________________ Josh was the kind of guy ev...

Six on One

by twoofer on Feb 13, 2018
Group Sex

1. The brown wooden door had a glass inset that distorted the images coming through it, like the ones used for shower doors or bathroom windows. It suited the second floor of the slightly run-down building on Mine St. The glass announced Therapeutic Massage in three inch black letters and underneath it said "Richard Dillon, MsT" Beneath Richie's name was "E...

My Wife is My Sex Instructor

by DrLit on Sep 12, 2017
Erotic Couplings

My wife and I met when I was 34 and she was 29. We both had been recently divorced after two years of marriage. Her husband was not great in bed and had been unfaithful. She had never had an orgasm. My wife had sex issues after the birth if our first child and the sum total of our sex life was her jerking me off to avoid fucking. I owned a health club. My w...

The Last Frontier - I Hope Ch. 01

by massageguy64 on Jun 19, 2019
Erotic Couplings

So if you have read my work you know that I mostly write about my experiences getting massages, mostly Happy Ending massages. These are all true stories, and I hope my writing reflects that. While a lot of these happen while I travel for business, they also happen at home in Texas. Sometimes they are basic hand job happy endings and sometimes they are full o...

First Erotic Massage

by Brian6588 on Sep 12, 2017
First Time

I have been a follower of literotica for 5 years now. I have been very fortunate in my sex life and have had a lot of unique experiences. I have always wanted to submit a story of one of my encounters but composition has never been my strong suit as I was a numbers type of guy instead. I submitted a story called "My Mothers Cousin" and it was published. Ther...

Diane Milking Sean Ch. 03

by stacey_lynne on Sep 25, 2017
Fetish

"Priapism is a potentially painful medical condition, in which the erect penis or clitoris does not return to its flaccid state, despite the absence of both physical and psychological stimulation, within four hours." Setting the rules: Sean A few months into the marriage I went to visit my daughter Samantha and her new husband, Sean. All was going very wel...

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...