Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Cruise Ship Cuckold Ch. 09

by Angelscuck on Sep 14, 2017
Novels and Novellas

Angel and I were pretty much left alone for the rest of the cruise. We had a wonderful time, visiting the islands, walking on the beaches, playing in the surf and enjoying the sites of Hawaii. We also enjoyed the ships facilities. We went to the nightclub shows, swam in the pools, watched first run movies and enjoyed the amazing cuisine offered almost twen...

Soccer or Succor Ch. 02

by techsan on Sep 12, 2017
Mature

Author's note: The following story is a work of complete fiction. Any semblance to people, real or imaginary, is purely coincidental. Thanks to Literotica reader Signore Calcio for the story idea and encouragement. Also thanks to Copperbutterfly for her editing expertise in making this story easier to read. Aaron Chambers: I knew there was something differ...

The Triple Blowjob

by Carnevil9 on Sep 14, 2017
Group Sex

"I've decided. I want a triple blowjob for my birthday." "What are you talking about?" She looked up from her book and gave me that "what are you babbling about now" look. "You said I could have anything I wanted for my birthday. And I've decided that I want a triple blowjob," I told her. She rolled her eyes. "And what exactly is a triple blowjob?" "That...

Black On Black Pegging: Somalis

by Samuelx on Sep 11, 2017
Fetish

I think the well-being of the international Black community would be much improved if Black men and Black women simply learned to communicate with one another. My name is Dhakiyah Falak Dawson. I was born and raised in the City of Ottawa, Province of Ontario. The only daughter of an immigrant mother originally from the City of Mogadishu in the nation of Soma...

Erika's Toy

by Dback69 on Sep 26, 2017
BDSM

Forty year old Daniel caught the eye of the nefarious Erika Reeves the minute he entered the Scottsdale Arizona saloon. Daniel who kept himself in shape with daily workouts on the health club treadmill was exactly what the younger Erica was prowling for. Erika divorced for two years had hit the alimony jackpot, which allowed the 33 year old redhead plenty o...

Sunday Afternoon

by xqzxxx on Sep 17, 2017
Loving Wives

"The house feels empty. And I do too." She said. I had enjoyed her and her husband's hospitality only two days before. Although they'd sent nice "thank you" notes, and we'd said we'd do it again, I really didn't expect it this soon. "Stan went fishing today and I'm here all by myself. I enjoyed Friday night more than anything I can remember in years. Would...

Take It Like a Skater Boy

by rckplsky on Sep 19, 2017
Celebrities & Fan Fiction

I can't believe that Avril Lavigne is at my mall! Her new CD "The Best Damn Thing" just came out and she's promoting it with this mall appearance. I heard about it on the radio about a week before it was going to happen. I'm so excited that I'm going to meet her. I've been a fan of hers for a long time. I have all her CDs and even some bootleg stuff of hers....

The Gentlemen's Panty Club Pt. 04

by joefelton on Sep 13, 2017
Erotic Couplings

As I was driving home from the meeting, I thought about the important club members I'd met. There was the honorable mayor of San Francisco, Justin Roberts, and the renowned opera tenor, Mario Sunseri, as well as the president of the San Francisco Ballet Company, Constantine Chekov. I'd met university presidents, and the leaders of the local bar and medical a...

The Balcony Ch. 02

by brian473317 on Aug 31, 2017
Exhibitionist & Voyeur

Sunday morning Ken woke up early; at least early for a Sunday. It was 8:00 am and he was wide awake and grinning like a fool as he thought about last night. Seeing Katia nude had been thrill enough. Her body was gorgeous with her long black hair hanging in ringlets as far as her C-cup breasts; her triangle of jet black hair framing her pussy. Even thinking...

Lessons in Love

by Nabla on Sep 2, 2017
Erotic Couplings

Natalia and I will be married six years this July. In that time our relationship has blossomed and grown, particularly our sex life. We have explored our deepest fantasies and made them a reality. My arse has always been a turn on for her. I always found that surprising as I considered it nothing special. When we first started to go out she would wait until...