Gay Surprise Stories

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Bi First Time

by Mercurious on Sep 17, 2017
Gay Male

--This is a true story about my first experience with a gay man. It hasn't been exaggerated, it really did happen this way, and I'm all the better for it. I was in my early twenties at the time. I'd spent the previous day at the beach with my flatmate Karen. To my surprise had she turned up with her girlfriend Angie. Karen and I had lived together for years...

Truckstop Young Wife Neighbor

by Alluring_Crimson_Shifter on Jun 12, 2019
Gay Male

Wendy lived with her husband in a middle class neighborhood. It was a comfortable neighborhood with a convenience store within walking distance. There was a retail strip nearby with hair salon, a barber shop, parts store, and a book store with an arcade. Also there was a truck stop next to the neighborhood across a wooded area. On this sun shiny day Wendy w...

ABS Days Ch. 03

by Indianaboy6555 on Mar 11, 2019
Gay Male

My adventures at the local bookstore were getting more and more interesting, and more and more frequent. I was back in my favorite booth more and more. Then one evening, my world changed dramatically. I was married at the time you see. My wife had some issues that led to a long dry spell. That was what led me to explore my wild side. Quarterly sex just was...

My Gay Crossdressing Vacation Ch. 01

by Flame666 on Apr 21, 2020
Gay Male

It was mid-January and I was getting tired of the cold and I was horny so I started to think about planning a gay vacation. After a lot of thought I decided on Palm Springs in Mid-February. A bit about me, I am a straight looking and acting man 60 years old slim and fit. However, I love cock and like to dress up in panties and other lingerie. A few years ag...

Fuck You Dad Ch. 02

by Nasties on Sep 28, 2020
Gay Male

***This story continues where 'Fuck You Dad Ch. 01 left off*** ***All characters are 18 years or older*** The next morning I woke up, feeling satisfied and happy whilst trying to remember the feeling of having a cock up my ass. I got out of bed to go for breakfast and I put on the same cum stained pants from the day before. As soon as I dad sees me, he tel...

Sacrificed by Curiosity Ch. 06

by sr71plt on Sep 14, 2017
Gay Male

Now I could put the ultimate part of the plan into operation. The brunette was good at what she did. On the date she specified, she had everything set up, and all of her directions, as I had outlined to her, were followed to a tee. We were in her darkened bedroom, stretched out on the bed. I was the one in the black mesh stockings and the spiked heels. I had...

Trucker's Whore Ch. 02

by andrewforfun on Sep 14, 2017
Gay Male

At precisely 5.57pm I was standing at the truckers' stop exit with my small bag carrying an umbrella to make sure I would stand out. I looked around at the unfamiliar trucks, massive beasts of the road and wondered which, if any, was his!. One started its engine and I looked across watching as it slowly jumped forward as its driver slammed it into gear and...

Straight guy gets anonymous massage

by Harryj34 on Apr 20, 2020
Gay Male

I'm a guy in my early 20s and I consider myself straight. I've only ever been attracted to women and don't find men physically attractive. I'm usually fairly successful with girls, I'm over 6 foot tall, in good shape and young looking, however, last year I ended up having an experience I never could have foreseen. I was incredibly horny and had been trying t...

Victor and Samuel Ch. 04

by RedHairedandFriendly on Sep 14, 2017
Gay Male

A biting chill rushed through the door before Victor was able to shut it. His feet were covered in snow; his hair, moist from the falling flakes, clung to his forehead. He dropped his keys on the small table by the door and headed to the kitchen. The darkness was a bit annoying so he flicked on the light and was suddenly surrounded with shouts of "Surprise"...

Sail to the Sun Ch. 04

by sr71plt on Aug 18, 2017
Gay Male

The first time I was with Buddy, we didn't have sex. That was something of a turning point with me. I was a commodity. I had always been a commodity. Men paid for my time. But the time they were paying for always was for the sex. That is, it was until the first time Buddy paid for me. I knew the night he decided to pay for my time. I saw him talking to Hoag...