JackinChat forums are temporarily in read-only mode. Will be back soon!
Message Boards
Index » Sexuality » Rainbow Room » First Time Gay Experience
Page: of 3   next > 
TonyIsBi123 Novice Jackinchatter

10 posts since 2022-11-22
63 year old bisexual male from MA, USA
TonyIsBi123's Avatar
Would love to hear about 1st time experiences. Was young when I had my 1st. He was only 2 years older than me and we were camping, He convinced me to sleep naked as he said the cowboys used to do it. What the hell did I know so we did. As he slept he got a hard on and started to moan blow me blow me over and over.
Not sure what came over me but I couldn't resist and leaned over his body and started to suck him off. Before I knew it he shot his load into my mouth catching me by surprise and gagging me so I spit his cum out all over his cock.
The next morning he laughed when he saw his cum covered cock and said he must have had a wet dream. I told him no he didn't and that I did that to him. He didn't believe me and told me to prove it.
So I sucked him off again, this time when he came I swallowed quite a bit of his load. After that, I became his regular cocksucker until he moved away a couple years later.
Add a reply Quote this post
User is offline Send Message to User View User Profile
Demigxx Amateur Jackinchatter

122 posts since 2014-07-23
49 year old bisexual male from Northumberland UK
Demigxx's Avatar
First time was a sex shop with cabins in Helsinki when I was there with work. Probably late twenties at the time. I'd had a couple of drinks and went in there and found a cabin, was just sat watching porn wanking, aware that there was a gloryhole next to me although cabin next door was dark. The thought turned me on a lot and has no-one was in there that I could see so whilst looking at the porn I was watching, ladyboy stuff, I pressed myself against the wall and shoved my throbbing cock through the hole. Within a second a tongue touched my balls and slid up and a hot mouth was on my cock. Felt so good but so surprised! I came very quickly, best bj I'd had at that point, never had someone literally suck the spunk out of me like that. I knew it was a guy as I felt the moustache and as I left he came out of the cabin looked at me and licked his lips, was incredible.
Add a reply Quote this post
User is offline Send Message to User View User Profile
ShortFuse Professional Jackinchatter

1248 posts since 2019-11-03
52 year old bisexual male from Nashville, TN
ShortFuse's Avatar
First for me is when I was 15yo. Watching a porn with my best friend. We both got horny and took turns going to the bathroom to jack off. Later that day we watched more porn and decided that since we'd see each other naked, and we weren't gay, that we would jack off as we watched the video. That turned into jacking each other which turned into sucking each others cock. He didn't like sucking my cock, but the minute I tasted his cock I loved it. He had agreed not to cum in each others mouth, but when he tried to pull out I grabbed his ass and pulled him in. I felt his warm load squirt into my mouth and heard him moaning. I swallowed every drop.

He was shocked and made fun of me a bit calling me a "fag", but he was happy to let me suck him many more times after that. He said, "You suck dick better than my girlfriend".
Small dick chronic masturbator
Add a reply Quote this post
User is offline Send Message to User View User Profile
Doug55 Skilled Jackinchatter

647 posts since 2017-05-22
59 year old homosexual male
Doug55's Avatar
Wasn't it the most beautiful sexual experience
you ever had??????????stroke
I am your bottom
Add a reply Quote this post
User is offline Send Message to User View User Profile
TonyIsBi123 Novice Jackinchatter

10 posts since 2022-11-22
63 year old bisexual male from MA, USA
TonyIsBi123's Avatar
You never forget yuor first!
Add a reply Quote this post
User is offline Send Message to User View User Profile
UncutBiBud Novice Jackinchatter

7 posts since 2022-12-06
39 year old bisexual male from BC, Canada
UncutBiBud's Avatar
Well, the first time I ever did anything sexual with a guy I was in my early twenties. I had read about some men who jerk off with each other and still identity as straight. As a then identifying straight guy, I was really curious. I was very nervous to bring up the topic with my friends, but I eventually had an opportunity.

One night I was playing some computer games with a good friend, and he was never the judgy kind of person, so I carefully mentioned how I read that some guys watch porn and jerk off together. He said that he had done it! Not only that, but he had received and given a blowjob. I was shocked, but very curious about it. He then asked if I would like to try something like that then and there. I hesitantly said yes, and he said jerking off or blowjob? Naturally, I agreed to a blowjob.

So we went over to the bed, and he went down on me. I couldn't believe I was doing something like that with another guy, and a friend at that. But it felt really, really good. I didn't last too long and came in his mouth, which he swallowed. Then it was my turn...

I really wasn't sure what the heck to do, but I figured I know what I like done to my cock so I'll just do that. I was taken aback by how smooth his cockhead felt in my mouth, and I was surprised by how his cock did not have a taste at all. I don't know what I expected, but it wasn't that. I must have done a half-decent job, because he came after a few minutes of me going down on him.

It definitely was an interesting experience, my first time with a guy. But by far not the greatest. I was only curious at the time and dealing with a lot of social stigma in my head about the whole situation. But I kept exploring and doing things, and eventually I came to terms about how normal it is to do things with any gender, provided that it is safe and consensual. I've had some awesome times since then, but I'll always remember that first time.

I am new to the site, and so if anyone is interesting in chatting about that time, other times, or really anything at all hit me up. Sexuality is an awesome topic I enjoy talking about.
Add a reply Quote this post
User is offline Send Message to User View User Profile
Unregistered ?



Unregistered's Avatar
I've had an outdoor nudity fetish since I was 13-yrs. old. I grew up in Deerfield IL north of Chicago and went to Deerfield High School. If you check it out on Google Maps, you'll see that the high school sits on several acres of land...surrounded by several athletic fields.

When I was in college, I used to walk around the perimeter of the high school totally naked late at night. During daylight hours, I walked around the perimeters of the athletic fields in the nude.

When I was 19, in between my freshman and sophomore years in college, I got caught by an older married guy (maybe 50-something?) on a Saturday afternoon. He'd found my pile of clothes and hid them, telling me I could have them back if I gave him a blow job, which of course I did. He was huge...about 8" cut. I struggled with him orally...choking and gagging and sputtering on his thick cock. He pulled out of my mouth and ejaculated all over my face. Then he made me lick his asshole.

He gave me my clothes and called me a "fucking faggot." I never knew his name, and I never saw him again.

It was fucking awesome!

cockstrokeeyeshotrazz
Add a reply Quote this post
User is offline
RobBanks Amateur Jackinchatter

382 posts since 2021-05-28
67 year old curious male from MS
RobBanks's Avatar
Maybe I was 13, 14, I don't know, can't remember now. Long story short, we were "camping out," which entailed us staying out all night. This guy I was with -- I'll just call him D -- he was, I later learned, a bit of a teen burglar; he knew there was a vacant house in the neighborhood that was for sale and had been for some reason left open. We went in there, just hung out for hours. He had some whiskey that, I later learned, he had purloined from a house in the neighborhood. He drank, I didn't.

He started complaining of being hot and removed his shirt. Not long after, he complained of being hot again and removed more clothing. He kept asking me if I was hot too. Eventually, totally clueless, I started removing clothes.

He asked if I liked massage. I said I didn't know what that was. He had me lay face down on a bed made from our clothes and he began caressing me, my back, arm, ass cheeks, legs, this light, feathery touch that made my skin quiver. It was delicious.

I was so, so very hard and inflamed; my young cock was raging. We changed places, me telling him I wanted to do the same for him. I caressed him for a long time and then we changed places again. When we did, I put my hand down and, yeck, put it in ... something sticky. I didn't know what it was right then, but I worked it out in my mind pretty soon: he had cum while I was caressing him.

I asked whether he did frontal massage. He sighed, said he didn't usually but he would this time. And he began caressing me again, this time as I lay on my back. He leaned over and took me in his mouth. He didn't know what he was doing; he just held my cock in his mouth, not moving.

Later we changed again and I did the same for him. I never came, though, and we didn't see each other much after that.

Months later some other kid razzed me that I had sucked D's dick. So D, being the prick son of a bitch that he was, went and told people that I had gone down on him, conveniently leaving out the part that he initiated it and went down on me (if you could even call that going down).

Anyway, D seduced me. Why he went and told somebody else, I don't know. D is just a jerk, I guess.
Add a reply Quote this post
User is offline Send Message to User View User Profile
Hairybi Amateur Jackinchatter

209 posts since 2013-12-28
72 year old bisexual male from Utah and California
Hairybi's Avatar
We are born with certain sexual desires, and we can be imprinted early in life by sexual experiences. From the moment I saw a shirtless man, I was interested in men, but being raised in a conservative religion and city, going gay was not an option. I was masturbating around 8 or so, before pubes.

When I was 11, an older cousin (16 or so) suggested we shower together when I was at a sleepover with his younger brother. I was fascinated with his hairy cock that looked like a beer can to me. He had a patch of chest hair between his nips. He suggested we soap each other and rub bellies together. Of course, our erect cocks got in the way. Soon, we were masturbating each other, and sleeping nude in his twin bed. I often wondered how he knew I'd be interested and discrete.

That led to action with a young neighbor who matured early like I did, experimenting in a tree house he built, circle jerks at Boy Scout Camp, and later one on one action in high school with a friend. We would date high school women and look at porn afterwards. Funny, I can still remember the scent of my young neighbor when we played and can describe his cock and my high school friend's cock in detail.
Add a reply Quote this post
User is offline Send Message to User View User Profile
tribeca Amateur Jackinchatter

348 posts since 2010-01-29
83 year old homosexual male from NYC
tribeca's Avatar
I agree "we are born with certain sexual desires." I always knew I liked men, but never did much about it with anybody. However, growing up in New York City did have one great advantage - the mensrooms on the city subway system.

When I was 10 or 11, I happened to go into one, in downtown Manhattan, to pee, and saw the guy next to me wasn't doing that. He had a hard-on and was playing with it. I was intrigued, but too afraid to do anything.

A week later I went back to that mensroom and there was a different guy, but doing the same thing. This time I stayed and let him see I was jerking as well. I didn't let him touch me, though he wanted to. I don't think I came that time, but a few weeks later, at my home station's mensroom in the Bronx, I did cum.

Maybe a week later there was a guy who looked like a movie star (actually, like Peter Lawford) whom I let touch and play with my dick, so I guess that was my first real gay time. He jerked me off with one hand and himself with his other. My orgasm was so strong I nearly fainted.

I ended up getting hand jobs and blow jobs at various subway station mensrooms for decades. (I eventually gave them as well.)

It wasn't until I was 17 that I had an experience that involved intimacy and romance.
always willing to help a nice guy
Add a reply Quote this post
User is offline Send Message to User View User Profile
Unregistered ?



Unregistered's Avatar
tribeca, your mail box is full.
Add a reply Quote this post
User is offline
Doug55 Skilled Jackinchatter

647 posts since 2017-05-22
59 year old homosexual male
Doug55's Avatar
Maybe 5 lol
I am your bottom
Add a reply Quote this post
User is offline Send Message to User View User Profile
Unregistered ?



Unregistered's Avatar
Doug55 said:
Maybe 5 lol


Pulling each others "tails?"
Add a reply Quote this post
User is offline
bdginky Novice Jackinchatter

38 posts since 2022-06-03
39 year old curious male
bdginky's Avatar
Had my first real experience recently. After going to the adult bookstore near me for a bit I finally met a guy who wanted to set something up outside of the bookstore. First few times we would meet up and watch porn while jacking each other off. We would take turns edging each other until we both were ready and then would lie beside each other and finish other off. Finally one night I asked if I could suck him and he quickly agreed. I teased him with my tongue, sucked the head all the things I like and I made sure to never get him too close to the edge. After a few minutes he was begging for me to let him cum so I started sucking him faster and harder as I began to feel his hips thrusting as well. It was so hot when he finally unloaded in my mouth and I sucked out every drop.
Add a reply Quote this post
User is offline Send Message to User View User Profile
Unregistered ?



Unregistered's Avatar
Summer of 8th grade. Camping with a friend. It's a long story, but eventually we graduated from jacking to frot to humping and sucking. Not much more.
Add a reply Quote this post
User is offline
Page: of 3   next > 
Index » Sexuality » Rainbow Room » First Time Gay Experience