Pimped Out Sissy Stories

353,644 results
Orientation
Length
Source
Infinite Scroll

Little Crafter Ch. 01

by Samhainchild on Sep 13, 2017
NonHuman

She worked through the night, again. The studio looked as though it was waiting patiently to be bare and painted crisp white once more. She'd begun a lease on the place the previous year for a small fortune each month, but the building was in an ideal location for her needs. Close enough to the city for work purposes, and far enough out in the sticks to put...

Getting Intimate with a Pillow

by therosebard on Sep 26, 2017
Toys & Masturbation

In the haze of between sleep and awakening, there is a sexual hum humming throughout my body. Night time just seems to bring out the lust. Lust is coursing through my veins. Soft skin still fresh from a cleansing bubble bath yearns for that intimate touch. A touch that can send my lust from neutral gear to overdrive. I'm sandwiched between my mattress and...

Sympathy Head

by thehumpman on Sep 12, 2017
Loving Wives

Once in a great while my wife likes to go out with some of her fellow girlfriends. They usually go out and dance, have a few drinks, usual girl talk. I can always look forward to a great night of sex when she gets home cause she is usually a little buzzed and ready for action. Around one a.m. I heard a taxi pull up to the house and what sounded like a lot of...

Chloe's Gangbang

by Idyut on Sep 13, 2017
Group Sex

Chloe looked at the note again. It said to meet him right here but she was getting cold and this was not the best part of town. Then out of nowhere, four black men showed up and asked one simple question. "Is you Chloe?" I drove fear and excitement deep into her heart. Will a brief nod, she was swept up and all but dragged into a nearby house. Without a w...

Taken Her Fist

by fistme on Aug 31, 2017
Fetish

My wife and I have always been adventurous with sex, but taking her fist was a challenge we both wanted to take. We started with ordering a new but much larger butt plug. The new toy towered over the other butt plugs that we had played with. This new toy was something entirely different. The plug was eight inches high and 3 1.2 inches across. In addition to...

Review: Boss's Orders

by velvetpie on Sep 16, 2017
Reviews & Essays

Erotic Confessions, Vignette: "Boss's Orders". Starring Ava Fabian (as Jacqueline Stone). In "Boss's Orders", a young lawyer enjoys a seductive date. * * * * * Jacqueline Stone is a writer and is a beautiful brunette with C cup-sized breasts and dark brown eyes. She begins this episode in an open cream-colored robe and she pauses in her living room to op...

Long Day of School

by Jay_nice on Sep 16, 2017
Toys & Masturbation

Being a new College girl, I hadn't met any guy I'd like to be with. I'm effect of this, I hadn't gotten any in a while. I had only gotten oral sex anyways. I was trying to save my virginity for the perfect guy. I went to Pitt, and I lived about twenty minutes away from the main campus so why would I wasted money on a dorm? Anyways, today was filled with long...

Ruby & I Ch. 01

by ohumwow on Sep 1, 2017
Group Sex

It was a warm summers night, and I had been in the city with my boyfriend Stefan. I had been shopping and purchased a nice dress, that showed off my large tits. It left little to the imagination, and knowing that I was about to surprise my boyfriend, I decided to leave my underwear at home. We arrived at the bar, and we grabbed a table in the middle of the...

Bar Stars Ch. 01

by TheWastelandRanger2247 on Sep 17, 2017
Group Sex

Ch.1 – Ginger It had been a slow night at the bar for you, no interesting people and the music the wannabe DJ, had everyone off the dance floor. You had just begun to think that this whole night would be a bust when the a soft touch on your arm got your attention. You turned around to find a petite blond bombshell smiling at you and holding out a pair of s...

Roommate Ch. 02

by WhoAmI99 on Sep 12, 2017
Exhibitionist & Voyeur

Chapter 2: Double or Nothing We asked if she wanted to keep playing, and she said that of course she did. This time, we told her that she would need to have sex with the winner. She looked a bit taken aback by the escalation, but agreed. As we played, both Larry and I lost our boxers. Both of us had raging hard-ons at the prospect of fucking this beautiful...