Oldest Gay First Time Sex Stories - Page 4

First Time Meeting Gay Guy in Swim Team Tryouts

With each day it turned out that he was hard in the locker room as we changed... and my thinking was that it was over me because I was the only one in the locker row with him! I had been taking every oppurtunity for the two weeks of tryouts to talk to him as we were waiting to be picked up... and I was almost DEFINATE that he was gay... so since the last day of swim try outs were the last day of school before the winter break I thought I would make move then. Unfortunatly he didn't show up on the last day, or I may have just missed him... because we were only looking at the list for who made the cuts (neither of us got cut)
2.6 815 words 4 mins locker room

Short Story About First Time Threesome at Prom

So while Darren bounced up and down on Josh's dick, I took Darrens dick in my mouth and sucked him off until he shot his hot stream down my throat. Then Darren got off of Josh's dick and layed stomach down on the bed and gave Josh a blowjob. I kneeled down just below Darrens ass, opened his muscular buns and pushed my dick all the way in Darrens tight ass. After a few minuts of fucking his warm butt, I shot inside him and a few seconds later Josh shot his load into darrens mouth. After we cleaned up and got dressed they told me that the story we would tell everyone else is that we all went to get something to eat and to this day that is what everyone else thinks.
3.5 695 words 3 mins

First Time In Military School

Rick loved to horse around and wrestle, and I really did not mind at all because he was close to me and I put up a good fight but I let him take me down most of the time. I have always been really well built and worked out and stuff and one night after lights out and we were doing our thing he had me pinned down and he asked me, "Why do you always let me win?" I looked up at him and asked, "Do you want to know the truth?" He said yeah and I told him, "Because I like having you on top of me." He looked at me a little strange and started to smile then came closer to my face and said, "You know, I like being on top of you."
3.7 804 words 4 mins balls sucking  blowjob

Short Story About First Time Sex with Army Man

The railroad tracks and a small running stream divided the park. I had to use the bathroom in rather a hurry and run in and saw this man peeing. He didn't mind me seeing his cock which to me was a big piece of meat. Well I finished and run out but the thought of that cock stayed in my mind.
3.4 480 words 2 mins big cock  blowjob

First Time Short Story

Touching him in so intimate a way snapped something inside me, and, giving in to my newly-awakening sexual appetite, I slowly lowered myself to my knees in front of Mark. I could see his whole body now, and I thought briefly of allowing him to wake up to my caresses. But I realized that, good Catholic boy that he was, Mark would flip out and our friendship might never be the same. I couldn't risk it. Still, this might be the only time I would ever get this opportunity.....
3.1 636 words 3 mins

First Time Sex With Married Bi Man

I lead him into my bed room. I take his shirt off and we lie on the bed. He has my shirt off....and starts to unbutton his pants. I say "Let me do that", I begin to undo his belt and just as I'm unzipping his pants.....I look at his and say "a present to unwrap" and we both laugh. I unzip and he raises his hips so I can get his pants off. He takes his underwear off real quick! I would have liked to do that slowly but the guy was as hard as a rock....So, I understand....I take my clothes off real quick! Soon we are both strip naked!!! and were lying next to each other pressed real close. I feel his hairy chest pressed against my almost smooth chest....Oh, I've waited a long time for this!!! I love a hairy man what a turn on!!
3.4 1723 words 8 mins hairy  big cock  cowboy  shower

First Time Frat Brother Story

I had allegedly gotten a single to take conquered babes to after parties...though Mike was a babe definitely worth conquering :-) There were a few occaisions that he and I basically got caught with our pants down! There would be an unplanned knock on the door, and we would either have to pretend there was nobody in the room (a difficult task, given that there was moaning coming out of the room just seconds earlier), or hope that we could get our pants on fast enough to make things seem kosher. .... Despite a lot of great firsts, after Mike and I broke up it took me over 2 years for me to accept the fact that I was gay. I know where he is now though...he's a great friend, and I'll never forget him and my first time.
3.6 775 words 3 mins fraternity

Short Story About First Time With Transvestite

Had only had sex with a man once before, curtesy of a glory hole at my college, a concept I couldn't resist. But years had gone by, and I was living in the city, working at a store 6 days a week, and rarely going on dates. When I realized she was a he I laughed and apologized for making a mistake.
3.9 332 words 1 mins latino  blowjob  glory hole

Short Story About First Time Getting Jerked Off

I had never really been interested in guys before and had quite a few different girlfriends at that age so I never was horny for long. I was always able to find a girl when I wanted one because I've always had a good sized cock and girls at that age are very curious. I immediately went back to sleep.
3.4 598 words 3 mins twink  teen

First Time Jacking Off in Adult Movie Theater

After about 10 minutes of this I got up and sat in the seat next to him. I looked strait into his eyes as I started to stroke the insides of his hairy thighs with my free hand. I moved up and down his thigh with a feather touch while he was rubbing the bulge in his shorts. I eventually moved my hand to his crotch. I could see that he had pulled his shorts up as tight as they could go. Most of his ass cheeks were hanging out. I imagine his shorts were rubbing on his asshole each time he squirmed is his seat. This made his bulge evem more promenent.
3.1 621 words 3 mins

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