Gay Skirt Stories

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Office Prostitute: Exotic Discreet

by Alluring_Crimson_Shifter on Mar 26, 2019
Gay Male

Monique, a fit and well groomed office assistant straightened her skirt, and pulled her panties out of her ass crack. She licked residual cum from her lips and swallowing once more to clear her throat, enjoying the taste. She said, "Merci beaucoup," and took the money from Mr. Johnson for the blow job. Monique had been earning extra money for showing her bo...

Gilded Cage Ch. 01: Frustration

by sr71plt on Aug 21, 2017
Gay Male

This is a completed four-chapter story that will post by the end of May 2017. ***** "You need to pull the edge of the skirt down more, Alec. I can see your nuts from this angle. And can you hold the perfume bottle more under your chin and tilt your head up a bit more? It's supposed to at least look like it's about the perfume, not you. OK on the head tilt,...

Mardi Gras Adventure

by HerLittlePiggy on Aug 18, 2017
Gay Male

Shelly walked briskly down Bourbon St while I followed close behind. Her fat round ass, encased in a tight, short skirt, swayed from side to side as she deftly navigated through the crowd in her 4" heals. A mass of beads, ranging from small to big, was draped around her neck but they did little to hide her huge, God given breasts. "Show your tits," a group...

Strap-on Fantasy Twisted

by talk_2_me_whenever on Aug 18, 2017
Gay Male

We are at the bar and you are playing great music and I keep coming up to the dj booth to tease you because I am in a short skirt but tonight I don't wear any panties. You are drinking to the point of no return and you called your wife and told her you were going with "the boys" so she didn't have to come and pick you up at the bar. Well needless to say, I a...

My Brother's Keeper

by tvdude17 on Jan 23, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** I look pretty in my mother's clothes, I thought to myself as I stared into the mirror. An old grey skirt of wool was draped over my long legs and an orange top fitted tightly around my flat chest, only sagging where my boobs were supposed to be. I never identified as a woman but s...

Darren & Dean do Dale Ch. 03

by betamale08 on Aug 7, 2019
Gay Male

After we had our steaks, which were perfect I might add. I did clean up again, donning my apron over my top and mini-skirt, where again I was playing little miss homemaker for the two men Darren and Dean while they sat out having coffee and then joining them once I was finished, I came back out to them with three beers, one for each of us this time. I didn't...

Wife's New Job Pt. 01

by jaygreenx on Sep 25, 2017
Gay Male

All rights reserved -- this story is a work of fiction and remains the property of the writer. Chapter 1 Times were difficult. To make ends meet, my wife had taken a job in a lawyer's office. She had been working on her art for the last three years, but our bills had begun to pile up, and we needed the extra income. I was amazed how quickly she got a job -...

A Gay Surprise

by Compdood on Sep 25, 2017
Gay Male

I get home from work one day. As I walk in the front door my wife greets me, dressed in a skimpy little outfit. Her hair is cut in a short bob style and dyed bleach blonde. Her eyebrows are brown as is her bush, which is shaved in a small strip which I can faintly see through the fishnet skirt she has on. It's a smoking hot look that she's kept for a while....

A Day with Daddy Ch. 02

by pjcjb100 on Sep 14, 2017
Gay Male

The email read: "Daddy's little girl has been a naughty little slut, masturbating like that on video. You must be punished for acting like such a little whore. To help you learn your lesson, I have posted your video to Xtube. Come tomorrow at 2 pm so that Daddy can teach you some discipline. I will let the doorman know you are coming. If you behave appropria...

I Thought I Wanted It Rough... Ch. 03

by LonelyVirgin on Sep 14, 2017
Gay Male

How could I have let this happen? Every bit of it was my fault. I was responsible for the gag in my mouth and the handcuffs on my wrists. No doubt it was my fault that I was bent over the corner of a hotel room bed, with my legs bound tightly in opposite directions...spreading them wide. I was responsible for the school girl outfit I was currently sporting,...