First Time Gloryhole Stories

351,036 results
Orientation
Length
Source
Infinite Scroll

The Sweet Taste of Honey Pt. 02

by airoralover on Sep 14, 2017
Transsexuals & Crossdressers

In Part One I had moved into my aunt's apartment while I looked for a place to live at university. On my first day I had discovered her vast array of deliciously fluffy mohair and angora sweaters and had started to wear them and then began wearing her underwear. One Sunday morning she caught me wearing her clothes while lying on her bed masturbating and afte...

Eight Candles for Eight Rides

by jennanips on Sep 2, 2017
Erotic Couplings

*This story is a work of fiction. All resemblances to any person are purely coincidental. All rights reserved by author.* Special thanks to my "partner in crime" (and other things,) author NotReallySure. * Deuce opened the simple blue card to find a pair of Disneyland tickets inside. He looked up at his girlfriend, Rachel, with a big smile on his face. "B...

Gifted Bk. 01 Ch. 04

by JoshuaGlynn on Sep 15, 2017
Novels and Novellas

You know all the usual stuff, don't read if it's illegal or you don't like sex or sex between two males offends you. All characters are purely fictional, and any likeness is coincidence. Joshua Glynn reserves all rights to this story, the characters, and the world they live in. This story is about an 18/yo boy struggling with the gifts that he possesses, a...

Journey into Cuckoldry - Perfect Ten

by JennyGently on Sep 18, 2017
Loving Wives

It was another bright Sunday morning, two days after Alice and I had seen Carmen and Steve going into the cinema with their new potential conquests, Julie and Gary. The kids were at their usual soccer practice so we had taken the opportunity to go to the gym together. Alice had booked her favourite spinning class while I had intended to spend an hour working...

Boys in the Attic

by Roustam on Sep 15, 2017
Transsexuals & Crossdressers

Shortly before I began my junior year at SUNY Binghamton, I rented a room in a boarding house near the campus. I was tired of dorm life. The noise and the lack of privacy during my first two years at college had always been very annoying. My roommates were tolerable, but they tended to invite friends over at all hours for parties or long, dull bullshit sessi...

String of Luck Ch. 06

by MrIllusion on Sep 16, 2017
Exhibitionist & Voyeur

For those of you still wandering if I managed to make myself sexually decent for the night following my discovery of Aria: I did. Somewhat... On a regular day it wouldn't have been difficult to be hard, all night long, for two women as gorgeous as Nella and Aria. But the afternoon with Aria had been quite draining. I managed to fuck each of them, but I relie...

Rocky's Kingdom Ch. 05

by tcwild100 on Sep 16, 2017
Novels and Novellas

AUTHOR'S NOTE: This is the fifth in a continuing series of stories about what is essentially a very high-class prostitution business in Asia, with the headquarters in Manila. 'Rocky' is the chief -- you could call him a pimp in other circumstances -- of the very large consortium which includes operations in many Asian countries. Although each section can st...

From College Student to Submissive

by ColleteSarkozy on Oct 12, 2017
First Time

I cannot believe I'm on a plane on my way to start my new life as a Submssive. How did I get here? What am I expecting from this stranger? Who would've thought an Ad in the paper would have me even consider being a sex slave. This is how did I got here. It started with me, a somewhat to-myself 20-year-old sophomore with a double major in chemistry and biol...

Ready for Master

by blondesubmission on Sep 12, 2017
BDSM

Ready Goosebumps run up my arms and down my spine as you buckle my collar from behind. "Is that too tight, baby?" You ask me as you push your hips into my bottom from behind, pushing me up against the door. "No," I respond. "It feels perfect." This brings a smile to your face. I can't see it, but can feel it against my neck as you bury your face into t...

Black Women Still Love Black Men

by Samuelx on Aug 18, 2017
First Time

My name is Steve Cherenfant. I sometimes wonder why so many young white women think all the black men on the planet are into them. With so many sexy black, Asian and Hispanic women out there for a tall, good-looking and college-educated brother like myself to choose from, why bother with some silly white bitches? Whenever I walk through my college campus, I...