First Encounter

[Luvcutdick]

My best friend and me at his parent's cabin in the early 70s. We both had girlfriends and a happy sex life but when showering together in a large shower after an afternoon fishing we compared the length of our hard dicks.
He started stroking my dick and I took his dick in my hand and stroked him. After we got out and dried off we got on a bed and began sucking each other. He sucked my cock first and then I sucked his big dick. He was very thick and pretty long so I became horny and wanted his cum in my mouth. He pulled it out before cumming and sucked me until I blasted a load in his mouth.
After I came he laid back on the bed and I sucked him until be sprayed a huge load in my mouth. I'll always remember my surprise at the force of his cum into my mouth as it was my first.
We continued to suck each other and topped and bottomed for each other many times. He was a great bottom with the ability to take my 7" with no problem. His thickness took me a while to get him all in but was pleasurable in time. After marriages we never played again which I have missed.

Good to hear that you both had opportunities to experience this side of your life. Your passage describes many similarities to my first j.o. / b.j. buddy. Due to his very big size it was hard for me to take him anally.

We both married and it cooled after that. We are still in touch all these years later

And we both always shot globs of cum, many times right over our heads. Clean up was always a bit messy.

Although no longer one of my fantasies, what happened stays clear and fondly in my mine.

 

[curious323]

First and only time was about 10 years ago. Finally found a guy close by on Craig’s list and got up the nerve to actually have him over (lots of chats previously that I always cut off before it got far). He came up to my place and we just talked for a while. Then, he asked what kind of porn I liked and we started watching some porn. I was too shy to actually do anything, but eventually he just took his pants down and was rock hard. I then got undressed as well and didn’t take long to work my semi into a full on erection. At first we just jerked a little, then I got up the nerve to ask if I could touch his. First time (and only) that I touched another cock, but definitely liked it. His cock was similar size as mine, but slightly thicker. It felt strange to touch another cock, but good. We jerked each other off for a while and then back to jerking ourselves. I knew that he was into watching guys cum from our previous discussion about porn, so I asked if he wanted me to cum on him, which he did. I came on his chest and that got him off immediately. I got us both a towel, we got dressed, and that was it.

 

[Luvcutdick]

First and only time was about 10 years ago. Finally found a guy close by on Craig’s list and got up the nerve to actually have him over (lots of chats previously that I always cut off before it got far). He came up to my place and we just talked for a while. Then, he asked what kind of porn I liked and we started watching some porn. I was too shy to actually do anything, but eventually he just took his pants down and was rock hard. I then got undressed as well and didn’t take long to work my semi into a full on erection. At first we just jerked a little, then I got up the nerve to ask if I could touch his. First time (and only) that I touched another cock, but definitely liked it. His cock was similar size as mine, but slightly thicker. It felt strange to touch another cock, but good. We jerked each other off for a while and then back to jerking ourselves. I knew that he was into watching guys cum from our previous discussion about porn, so I asked if he wanted me to cum on him, which he did. I came on his chest and that got him off immediately. I got us both a towel, we got dressed, and that was it.

I remember the guilt the next day after the first time both my buddy "did each other". There was a 2 week pause, but then we picked up again; glad we did

 

[thinkimightry1]

I'm still working on my first time... Same as others , I have gay thoughts till I cum...then I feel guilt..Then the next time I'm alone and horny... I'm back to watch'n gay/trans porn...But, I'm starting to lose the guilt/shame shit... As of last year, I started talking to a guy on-line and we are trying to iron it out...He's married and I'm not...He has three or four under his belt...But, only thing is , he wants car-play or to meet up at an ABS.....it being my first time I don't think that would work for me...Also, I think that if I got off first, I'd lose my desire to do him.... So .. I will have to suck him off first...I just want a place that I can relax and enjoy it...After I get a few down, then maybe car-head...To go camping , biking...hiking would work wonders for me... I think after the first one it will get easier.

 

[bi2]

I'm still working on my first time... Same as others , I have gay thoughts till I cum...then I feel guilt..Then the next time I'm alone and horny... I'm back to watch'n gay/trans porn...But, I'm starting to lose the guilt/shame shit... As of last year, I started talking to a guy on-line and we are trying to iron it out...He's married and I'm not...He has three or four under his belt...But, only thing is , he wants car-play or to meet up at an ABS.....it being my first time I don't think that would work for me...Also, I think that if I got off first, I'd lose my desire to do him.... So .. I will have to suck him off first...I just want a place that I can relax and enjoy it...After I get a few down, then maybe car-head...To go camping , biking...hiking would work wonders for me... I think after the first one it will get easier.

Just my thoughts on your first time, dont do it in a car. Also focus totally on him cumming first, you will be naturally excited regardless.

If you can, have a wank in the morning if you are meeting someone for the first time in the evening to take the edge off when you first meet up.

Just my thoughts, others may offer different opinions here.

 

[thinkimightry1]

Just my thoughts on your first time, dont do it in a car. Also focus totally on him cumming first, you will be naturally excited regardless.

If you can, have a wank in the morning if you are meeting someone for the first time in the evening to take the edge off when you first meet up.

Just my thoughts, others may offer different opinions here.

Thanks... I can relate to what you said....

 

[HorseHung40's]

I was in college. He was on the swim team. We became friends, then sex buds. We were "friends with benefits" to each other, long before that term ever came into use.

 

[briacon429]

I'm still working on my first time... Same as others , I have gay thoughts till I cum...then I feel guilt..Then the next time I'm alone and horny... I'm back to watch'n gay/trans porn...But, I'm starting to lose the guilt/shame shit... As of last year, I started talking to a guy on-line and we are trying to iron it out...He's married and I'm not...He has three or four under his belt...But, only thing is , he wants car-play or to meet up at an ABS.....it being my first time I don't think that would work for me...Also, I think that if I got off first, I'd lose my desire to do him.... So .. I will have to suck him off first...I just want a place that I can relax and enjoy it...After I get a few down, then maybe car-head...To go camping , biking...hiking would work wonders for me... I think after the first one it will get easier.

I agree with everything Bi2 said. I would add there’s nothing to feel guilty or shameful about. If you get turned on by gay/trans porn, or if you want to try stuff with a guy, that’s totally natural. I know it’s normal to feel nervous (and I did too, when I was starting out!) but you don’t want to let that get in the way of your enjoyment.

I guess what I’m trying to say is, do it when you’re ready. You might still have a few awkward moments, just like any sexual encounter, especially when you’re trying stuff for the first time. But that can be sexy in its own right, and you hit the nail on the head: make sure you can relax and enjoy it!

 

[deleted779386]

I was young, early teens and exploring. I developed early so there was always some intrigue over my dick which back then was bigger than my friends. My cock was big, curved and I could cum, my friend although the same age wasn't so developed so was fascinated by it. It was the old truth/dare game which ended up with dicks in mouths and repeated for a few months before he lost interest as he didn't want to be "gay".

 

[deleted11061721]

I quickly mentioned my first time in another post but will go into more details here

I was in my late 20's and in between girlfriends and was very curious about being with a man. This is over 20 years ago and there wasn't so many internet sites around like there is now. I found a swinger's magazine at a local smoke shop, bought it and found an ad from an older man (in his 50's or so) looking to play.

I contacted him and he replied back and after a bit he invited me over to his place. I finally had the courage to follow through and I drove to his place. He let me in, we chatted for a little bit and because I was so nervous I think he thought his hot tub in the back yard would help ease things. We undressed in front of each other and walked out to his private backyard and he had his hot tub going.

It was night time in the summer. The SF Bay Area nights are on the colder side so the hot tub was giving off a lot of steam and we quickly got in. We chatted some more and he made the first move by rubbing his hand on my thigh. He asked me what I wanted to do and I said I didn't know because this was my first time. He moved in closer and started stroking me and I did the same and rubbed my hands all over him.

I noticed that he didn't get hard but I was of course. After playing in the hot tub he asked me if I wanted to towel off and go into his bedroom and I said I'd like that. When we got out of the hot tub and I was toweling off, he leaned down and started sucking my cock. It was amazing and I felt like I was in heaven because he knew what he was doing. He stopped and I remember him telling me that he couldn't help himself (while smirking).

We moved inside to his bedroom and I laid down on my back and he straddled between my open legs and gave me a great blow job. I came pretty hard and we just laid there for a bit and I left after that. I did feel some guilt or shame but I later contacted him again and we met and fooled around in his hot tub and I tried going down on him. I couldn't get very far because he couldn't get hard but I gave it my best

He later moved away so I didn't see him after a while.

 

[socal1967]

My first was with my three best friends. A game of truth or dare led to the fun. No hesitation at all by any of us.

Yup, for me I was super young at sleepovers. "Truth Or Dare" did it every time.

 

[goander]

Having my cock sucked by a stranger in a steam room.

 

[latinluva]

I walked into a steam room and came out with cum all over me, not sure what if they were gay, bi or straight and married. Just shocked that a couple of guys made me horny as fuck and that was how my first experience went down. I was thinking it would be a lil more romantic, rather than slutty.

 

[CaptainGrey]

I was 16 when I lost my virginity and only dated women until I had my first time with a man at 20. From the moment I did it with a girl, I became obsessed with the idea of doing it with a man as well. I've tried going on dating apps a few times, especially Grindr, but never found the courage to meet a man until I literally craved for it and felt absolutely ready. I only dated men for a few months after experiencing it. The pleasure of exploring new things in new ways made me feel like I was experiencing sex again for the first time. Until I got bored of being intimate with men only and started meeting people of both gender again.

 

[goldscorpguy]

Strictly speaking my first m2m was in my mid teens when I used to stroke with my best school friend on sleepovers. My first adult time was only twelve years ago and although I've mentioned it on another post, I enjoy telling the story. It happened in a hotel sauna whilst on a vacation in New Zealand, a long way from home. The sauna was in the male locker room for the pool and gym. It was late evening, after a workout. I went into the sauna and there was one other guy stretched out naked. Fortunately the sauna wasn't particularly hot, as I usually can't stay in them for long. I laid out on the bench at right angles to him, and we started to chat. He was a similar age to me, slim and pretty toned. I learnt from our chat he was an airline flight crew member. As we chatted he nonchalantly started to stroke himself and as I watched I started to harden. I felt very self conscious at first, especially as another hotel resident could have suddenly walked in, but gradually my hand slipped down and I started stroking myself too.
After a few minutes of this he got up from his bench and moved over to my side. His hand replaced mine. It was so sensuous as he stroked me and I soon lost all my nervousness. Then he leaned forward and sucked me, while his middle finger slipped inside me. It felt like all my birthdays had arrived in one go!
After several minutes of this and with the heat of the sauna I felt the need to sit up on the bench, so he moved around in front of me. This gave me my first chance to stroke his now very hard manhood. As he moved closer, I leaned forward and sucked the head. His precum tasted sweet like my own. My hands moved to grasp his bum cheeks as I got used to his cock in my mouth.
My brain was doing reality checks, this really was me with a guy's cock in my mouth in a hotel sauna. I couldn't tell you how long we spent but we swapped round a few times from me doing the sucking to his mouth on me. We were both so turned on, I think if another guest had walked in on us we wouldn't have stopped. I remember at one point he was standing between my knees and I could feel his cock brush over my hole. It sent tingles through my spine, but I knew I had to say no to unprotected sex. If he had magically produced a condom I would have let him fuck me, of that I'm sure.
He was the first to cum, shooting his warm jizz over my chest. I came soon afterwards. We both walked out into the lock room, where the cool air really hit me. After showering he left and our paths never crossed again. When I was digging around in my wash bag for deodorant I felt the familiar foil square of a condom which I had forgotten was there. If only he had stayed a second night!

 

[flatiron]

My GF of 10 years broke up with me, and in a moment of raw honesty, I admitted to myself that I was bi. I set up a grindr profile. A few weeks later, I’m talking to a guy on grindr while getting extremely drunk, and I invited him over. He came in, I kissed him at the door (first time I’d ever kissed anyone with facial hair), I offered him a drink. We sat down and talked bullshit for a few minutes, then I started grabbing his dick. Sucked him off, he came, he left. Don’t think I ever saw him again. He was really sexy, too.

 

[flatiron]

I walked into a steam room and came out with cum all over me, not sure what if they were gay, bi or straight and married. Just shocked that a couple of guys made me horny as fuck and that was how my first experience went down. I was thinking it would be a lil more romantic, rather than slutty.

that is so fucking sexy. so many questions!

 

[hotguy88]

Getting my cock sucked. I couldn't believe how good it felt. I screamed when the orgasm hit

 

[Buddie]

Having my cock sucked by a stranger in a steam room.

Nice

 

[Bob filascio]

Mine was in the highschool locker room. There was this pretty hung latino boy (who I'd always guessed had a big dick but never really had proof of until the encounter). I had been being kinda flirtatious for a while with him and I guess he finally got he hint one day and was curious. I was really nervous that he was just tricking me until I had his big dick in my mouth. It felt weird at first. Like I remember thinking that there wasn't enough room in my mouth for all of it but I really enjoyed it. I blew him for a while then he decided he wanted to go a step further and he took my virginity. To this day he's the biggest guy I've been with.