Gay Prostate Exam Milking Stories

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I Get Married

by hotdaddy9 on Mar 7, 2020
Transsexual

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home and...

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The Island Ch. 01-02

by hydrangealawrence on Oct 21, 2019
Erotic Couplings

THE ISLAND, PART 1 My ears rang and everything hurt. My mouth tasted like metal. The world was a frosted window smeared with Vaseline. Slowly things came into focus. I was alive, and still inside the plane. I looked up. I looked to the side. I could barely move my neck. The pilot's side of the Cessna was ripped apart like someone took a can opener to it....

Compulsion ballbusting

by Sammy on Jul 28, 2019
BDSM

Anna was gonna have the best day ever she had managed to find a way to compel people to do anything she wanted but it only worked on boys so when she got to her middle school that day she was ready. In her homeroom class she knew exactly what she would do she would compel a bunch of boys into coming to her house so she could do what she pleased with them. In...

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Learning from Stacy Ch. 04

by monkeykinglives on Jun 2, 2020
Erotic Couplings

Ch. 1 Two work friends become kinky lovers. Ch. 2 First dominance and submission, and public sex. Ch. 3 Three days of rough sex at a rented beach house. Ch. 4 The Spanish Inquisition and dark art. Ch. 5 Opera and sex in Amsterdam. * This is a true story. It is as true as my memory and story craft can tell it. It is the story of how an ordinary divorced...

My First Ladyboy

by TheSevenSeas on Apr 20, 2020
Transgender & Crossdressers

She was my first. Before I tell you more about her and how I ended up in bed with this gorgeous creature, I should probably make a couple of things clear. First, I am a straight, alpha male. Ex-military, been through a few wars, worked in Africa for a while, have been married and never even looked at another male in a sexual way. Still don't, as there is no...

Dominant Hot Wife

by pantycum99 on Aug 31, 2020
Loving Wives

I went into the living room to peek out the window only to see the ups man driving away, and noticed a small package on the front porch. I got the package and began to open it only to find two sets of hand cuffs, and another box that contained what it said was an anal training kit. I opened that box and inside was three anal plugs from small to large, and a...

The Reversal

by Shadoe827 on Dec 17, 2019
First Time

He walked into the living room, and saw her fast asleep on the couch. She was wrapped in her favorite blanket... "Baby," he whispered, kissing her forehead and squeezing her ass gently. She woke slowly, wiping the sleep from her eyes. A huge grin spread across her face, and she rolled out of her blanket cocoon onto him. As they hit the floor, he heard a lo...

Baby, It's Bedtime Ch. 01

by Misskiss24 on Jul 14, 2020
BDSM

His first rimming. "Hey babe, it's time for bed." I call out as I begin dressing for bed. I am wearing nothing but a tiny, red, strappy scrap of lace. My bush pops out of the sides and the thin back strap rubs against my asshole. My heavy breasts sway over my stomach as I fondle my nipples into erection. I can hear my boyfriend getting out of the shower as...

Master's Femboy Maid

by KittyAshleyy on Apr 14, 2020
Transgender & Crossdressers

Ocean blue eyes looked back at me as I looked myself over in the mirror. My Master was hosting a get together of his like minded friends and had told me to dress in my best maid uniform. That was a black maid dress with a skirt that barely covered my ass, white gloves which reached past my elbows, a small white apron and fishnet stockings with a black garter...

Bob and Sara... and Theresa

by idlefantasies on Apr 14, 2020
Group Sex

Theresa has been a long time friend. I shy away from the "friends with benefits" title so commonly used to describe relationships because she has been so much more. A mutual friend introduced us at a party about ten years ago. I drove her home after the party and ended up spending the weekend. We share a lot of interests including swinging together and separ...