Gay Shemale Surprise Stories

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Surprise at the Door

by Luckystiff2112 on Aug 18, 2017
Gay Male

This just happened to me today! But it all started last night. My buddy came over and we sat around shooting the breeze; took a ride in his hotrod- a '69 RoadRunner! Way cool! We came back and proceeded to get pretty drunk. So I fed him, gave him some water to sober him up some, and then he left. I was home alone now. My wife is away for the weekend, and wh...

Long Time, No Suck Ch. 04

by Stontstr on Sep 1, 2017
Gay Male

That weekend was amazing. I felt really great about my relationship with Marc. Cloe, Stephanie's girlfriend, turned out to also have a surprise. See, she turned out to have a rather nice penis, a nice extremely large, uncut penis. Cloe had even named it, Clarence. Marc had to go back to town on business for several days, but Stephanie said he knew all about...

Bob Handles Mark's Huge Tool Ch. 01

by scrotus on Aug 18, 2017
Gay Male

I had long fantasized about being involved in a sex situation with more than one guy. I had done several three ways with a woman (two guys and one girl) but they never involved the other guy and I performing on each other. In recent years, I've developed an insane desire to move beyond my several male-male encounters and add a third guy in. This is because o...

First Cock Came From Old Friend

by Trinni69 on Aug 31, 2017
Gay Male

It was Saturday and I had nothing to do so I decided to go for a drive. I got into my car and headed out of the city in no particular direction. After driving for a while I realized I was close to Jim's house. We have been great friends for years but have not seen each other for a long time. I decided to surprise him by dropping by unannounced and see if he...

My Inner Slut Ch. 06

by SlutAlexR on Oct 30, 2018
Gay Male

Daddy had been gone for a few days. He was away on a business trip. We communicated frequently, and he reminded me a few times that he had a surprise for me this coming Friday. So I waited anxiously for the end of the week. On Friday morning, I received a text: "Hello luv. I have been in contact with your Owner. We will pick you up at 6 tonight. But be ready...

Curious and Horny - 22m

by toddmac781 on Dec 25, 2018
Gay Male

One night a few years ago, bored and horny as usual, I found myself stroking my cock to some porn and decided to peruse Craigslist. The usual posts were there. Old guys trying to find some younger cock, a few weirdos, and the usual straight guys testing the waters. One post stood out to me. 'Curious and horny-22m.' I clicked on it and very frankly he expla...

My First Gloryhole Visit

by Gregjm on Sep 14, 2017
Gay Male

I visited a gloryhole for the first time last week. I was not very experienced as I have only sucked off a few shemale escorts before, and they usually don't cum because of hormonal treatments. But I was quite curious after reading about them on the web. I chose 11:30 on a holiday Friday in a sex shop. When I got there, there were a number of cars in the lot...

My First Cock in Years

by Bostonsnowball on Aug 18, 2017
Gay Male

As I was driving home after a weekend away, I started thinking about going to the Paris Theater. I was feeling very aroused since I hadn't jacked off in several days, I needed to feel a pair of lips on my cock. I had been there before and always had some guy slobbering on my cock within 15 minutes of walking through the door. I parked as close as I could, t...

Business Trip

by Diego99 on Jul 16, 2019
Gay Male

This is a true story of my 1st experience with another man while away on a business trip. Names only have been changed for privacy... *** I'm 32 years old married with kids and have been straight all my life - up to now. My curiosity about experiencing with other men started years ago because of watching porn. I was initially into lesbian porn, then threes...

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...