Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Getting to Know Ourselves Better Ch. 05

by noody2005 on Sep 1, 2017
Group Sex

He pulled back from our embrace and slowly licked his way down my chest until he was on his knees between my legs. Moaning I felt his tongue just touch the tip of my cock and felt his hands on my ass as he licked the oozing precum. "Tastes nice" he murmured making me glance down just in time to see his hand encircle my cock whist the other was still on my...

Cupid's Arrow

by boo56 on Sep 1, 2017
Group Sex

"Man, why not? You tell me you haven't been laid in six months. You're thinking about hitting on Melinda at Club 400. I know with Melinda you'll get drama. I'm not so sure you'll get laid. You should come with me to Kathleen's. She's really nice and she's really horny. She wants to do some kind of cam-room porn with two guys. And, I guarantee you'll get laid...

Train Trip Turns Into Adventurous

by kinkycapitalcpl on Sep 17, 2017
Loving Wives

When I found out I was going to Toronto for business for a week I wasn't looking forward to it. I didn't like the thought of flying, I don't have anything against flying but I just don't like it. When I found out the client I was going to visit was right downtown I thought maybe I could take the train. That turned out to be one of the best ideas I've ever ha...

Living

by campmaster on Aug 30, 2017
Group Sex

Mike peered over Gabrielle's shoulder as they both read the email. Both were excited beyond words, yet ever cognizant of the fact that it was still only an email and that the true test would be in meeting the couple in person. Such was usually the case when meeting people through these internet personals sites. On the screen, this couple seemed ideal. Both w...

Beautiful, Beautiful, Beautiful Ch. 01

by ExperiencedStoryteller on Sep 14, 2017
Humor & Satire

His thought flew through his brain crashing into reality. He really was staring at a naked helper. He had been Santa Claus for 44 years and never seen anyone like her. He was now 74, so he had seen naked moms and older women who had just had too much egg nog. He had seen a cross-dressing grandfather/mother. He had been blown by a drunken grandfather/wannab...

Down But Still Up For Fun Ch. 05

by BobBaker on Sep 17, 2017
Mature

There are no characters in this story that are less then eighteen years of age. This story is pure fiction. Any resemblance to any real person, living or dead, is coincidental and was not the intent of the author. *************************** I lay there beside Mercy and Carol, mesmerized by their beauty. They were sisters, but they really did not look that...

Opening Night

by HowWideHowDeep on Sep 17, 2017
BDSM

"Opening Night" Per your written instructions, I've undressed and cleaned myself out thoroughly. I'm on the floor, ass in the air, kneeling on a towel with my knees spread widely apart. Laid out on the floor near my feet are two long rubber gloves and a brand new, but opened, tub of Crisco. At my head is a pair of headphones, an iPod, and a blindfold. A fe...

Road Trip

by NorthCoaster on Sep 13, 2017
Group Sex

As he exploded in her mouth she felt the car slow a bit, bearing to the right. She wiped the last remnants of his pleasure from her chin and sat up, taking a look at the rest area around them. They both needed to compose themselves so he picked a remote parking space in the RV lot and put the car in park. To their mutual chagrin, a small Winnebago pulled int...

The Poker Party

by cockster21 on Sep 13, 2017
Fetish

Me and Kristen like to invite friends just go hang out on Friday nights. We usually rent some movies, drink beer or have a poker game. That night, Kristen had invited 5 friends over for our poker game: Dave, Catherine, Alex and Vanessa. Alex is a high-school friend of mine, a 6ft. tall man with short dark brown hair. Vanessa is Alex's girlfriend. She is...

An Edible Journey Ch. 02

by NigelOW on Sep 16, 2017
Fetish

Our edible journey continues. Like any journey where you only have a vague or perhaps imagined, ultimate destination, ours ended up with some unexpected twists, turns, and decidedly slick and slippery curves. Little did I know that by unleashing my wife's inner slut, I also awakened something of a dominatrix in her! And maybe a bit of hidden submissive in me...