Prostate Plug Stories

26,965 results
Orientation
Length
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Infinite Scroll

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Working at Burger King

by jeffss45 on Oct 15, 2017
Exhibitionist & Voyeur

A Not-Typical Night Working at Burger King Many years ago, I worked as an assistant manager at a Burger King while I was in college. It was a good job for me at that time. The job was made better once I realized it was just a college job for me. It was also where I met Karen, my girlfriend through most of my college years. We hid our relationship from the...

A Husband's Submission Ch. 01

by Playnhrd on Sep 19, 2017
BDSM

My wife Lynn and I have been married several years. Lynn is 5'7," 120 lbs. near 40 years old, a slim dishwater blond with nice tits and a very firm ass, works out daily, dresses conservatively, but loves to put on sexy under things, lingerie is very much a turn on for her. She is a sweet and very pretty lady, rather quiet and passive most of the time, even s...

PVC Sissy Whore

by Dostoyevshe on Sep 16, 2017
Transsexuals & Crossdressers

One day I was bored and horny so decided to cruise around a local adult store and find some action. I squirted a good amount of lube into my ass, slipped in my favourite 3 ball butt plug and put a pink chastity cage on my tiny cock. I wore hot pink lacy panties and bra, a tight PVC miniskirt, high heels, a pink jacket and heavy makeup like a whore, complete...

The Rules of a Scheduled Encounter

by playfulsin on Feb 7, 2018
BDSM

Part 1: You pick me up and we are on your way back to your house in your car. As I get in you slide your hand under my ass as I sit down and give my left ass cheek a nice little squeeze as you lean over to kiss me briefly before we take off. You pull your hand out from under me and place it on my lap as we kiss, squeezing at my crotch to feel my cock. We h...

Retired and Horny Ch. 02

by JustALittleCrazy on Sep 16, 2017
Mature

In the morning, I wake first. I'm lying there and thinking this is the point where I usually take off or break up with the woman. I'm falling for Whitney already and the way she looks me in the eyes, I think she might be right there with me. But I have no desire to be without her. No matter what happens in the future or if she lets me have her ass, I know I...

A Need To Experiment Ch. 04

by cmbhere on Sep 16, 2017
Anal

*I am now at a point where I can split the story line and pursue a couple of different paths. I would like some feedback on which way to take this.* Thursday! It was Thursday! I had waited all this time to see what Bob and Linda had planned, and it had finally arrived. Well almost. It was only Thursday morning, and I had to get some work done before I too...

Blue Moon

by ash_rigby on Oct 12, 2020
NonHuman

Note: The human in this story is explicitly an AMAB (assigned male at birth) nonbinary individual who uses they/them pronouns. Words for male genitals are used for them, but they are not a man and any suggestion of that in the comments is not welcome. This piece is not intended to fetishize trans/nonbinary people (I'm a nonbinary trans person), so any commen...

It Took Eleven Days Ch. 02

by Whitegarage13 on Sep 16, 2017
BDSM

Usually I'm against planned sex, planned and scheduled sex lacks the passion and intensity I thrive on but recently I discovered prepared for sex can be just as intense. It all started while I was away on a long business trip. My wife thought it would be funny to send me dirty pictures while I was working. A nice tit picture, then a kinky panty picture, the...

M and H Ch. 05

by therealultimatedarkone on Sep 16, 2017
Anal

The doctor's appointment was almost over, Mari just needed her temperature taken and reflexes taken and everything would be done. She was sitting on the paper on the padded doctor bed/table/thing. She had on a paper gown, back open, exposing her supple skin and new oroburos tattoo on the small of her back. That was a whim, NOT drunken, but an idea that came...