Gay Shemale Surprise Stories

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First Trip to the Fantasy Boutique

by toddmac781 on Apr 3, 2019
Gay Male

A rainy, fall afternoon I made my first trip to the Fantasy Boutique. It's an adult bookstore in the edge of Philadelphia with toys, DVDs, magazines, and also has private dances, private viewing booths, and a three room theater. I walked in casually enough, and made my way straight back to where I realized they had girls giving private dances. On the opposi...

Second trip to the Dream Boutique

by toddmac781 on Apr 3, 2019
Gay Male

This is a true account of my second trip to the Dream Boutique. A Friday night, after doing some work with friends, my horniness got the best of me. I pulled up to the Dream Boutique around 1:30 am. It's open 24 hours, far enough from where I live, and always frequented by horny guys looking to get off. I went to the cashier to get a two dollar bill that...

An Executive Learns His Place

by Luctari on Sep 14, 2017
Gay Male

My phone dinged, an email from Tim, guy in our IT department. What the hell was he doing sending something to my personal address? How'd he even get it? I opened the message. Luke, I have an important matter to discuss with you that I don't think you'd want to talk about in the office. Meet me at the Motel 6 near the airport tonight at 7pm. Tim Who the...

To Serve You. Pt. 02

by mkh78 on Feb 10, 2020
Gay Male

This is a just a fun fictional story from the mind of the author. All characters are over 18. Enjoy. It is now fifteen months since we met and I am still my boyfriends "slave". Our first date brought us to this odd master and slave relationship. Although you may think it's "sick" for a 34 year old man to "own" a 27 year old man, we are both consenting adult...

Straight Boy to Bi Bottom Ch. 01

by young7inchfun on Sep 14, 2017
Gay Male

This is my first story. Please feel free to leave constructive feedback and let me know if I should continue. The following is a true story, with minor embellishments, of my first gay experience. Everyone in the story is an 18+ consenting adult. NOTE: if this story encourages you to use Craigslist or another online site, please be safe. My biggest tip is i...

Thomas's Long Hard Night Ch. 01

by wanderinjoekidd on Aug 18, 2017
Gay Male

He should have never gone to the bookstore in the first place, he should have just went on home to his wife, and listened to her bitch and whine about ... whatever. But, he went, and was he ever sorry now. He had cum in his hair, on his face, in his ass, and he wasn't sure where his underwear or his socks were. And the taste in his mouth was awful! The man...

Experimenting with Cock

by abiguy on Sep 14, 2017
Gay Male

What happens in this story is true. Only some names have been changed. Enjoy. See the bottom for my contact details. :) _____________________________ I was 22 and at the time did not have a girlfriend. I had a habit of jerking off at least once a day if not more. Starting masturbation at an early age made me bored by "normal" porn star videos. Leading me t...

Glory Skills

by glory_first on Aug 18, 2017
Gay Male

Finally finding enough time last Thursday morning and mid-day to run a number of errands, it was possible to finally revisit a newly (re)discovered gloryhole. Going into the porn shop around noon, it was about as empty as during the last visit, on a Saturday mid-afternoon. After paying and entering the long and dimly lit hall, a couple of men could be seen...

On a Run Ch. 01

by yeaimbored on Sep 16, 2017
Gay Male

I bent over to tie my shoe when suddenly I felt a hand on my ass and a voice say, "well what do we have here Johnny?" I instantly tried to stand up, but another hand on my back pushed me back down. "You'll stay there for now, I like the view," the man said as he rubbed my ass through my spandex running shorts. I was terrified, I knew there were at least two...

My First Times

by RonMurphy on Dec 17, 2017
Gay Male

If you look me up in an anthropology book you'd see that my species is Homo suburbanis. I live in the perfect neighborhood, in a perfect house with two perfect children. My wife is pretty, not beautiful but I often catch my neighbors staring at her lustfully. I am convinced that my wife could be the CEO of any Fortune 500 company - she runs the household as...