First time with a guy

For me it was in middle school. I used to walk with my buddy to his house after school. We started looking at porn mags together. Then eveventually started jacking off together. That progressed into jacking each other off, then sucking each other off. Eventually, I would try to put it in his ass, but we didn't know anything about lube, so couldn't make it work.
 
First time with a guy was with my first wife.
We got ...... at a wedding and swapped with her friends husband. Her friend fell asleep midway so me and other guy worked on my ex wife.
In the heat of the moment I just went for it and started sucking his dick. Wife was stunned but he got into it by grabbing the back of my head and trying to cram his cock deeper into my mouth.
 
Mine came late in life, at age 55. Met an older guy and a mid-50s woman at an adult theater. I expressed interest in sucking cock. We went to his place. I sucked him and she sucked me. He refused to cum, so kind of tantra thing. I came on her breasts. I wanted to eat her, but she was super sensitive or uptight about us touching her pussy. I wish I had gotten her contact info. She was in good shape for her age and into the mfm sex and probably would be open to more combinations. Never saw her again.
 
  • Like
Reactions: nicebiguy
I have had a few experiences.
First was as a kid with my cousin, we would suck and fuck each other's ass, probably 12 or 13 at the time. We continued that for years.
Then when I was in the service, I went into town and was at a bar. Man sitting next to me started buying me drinks, said he always bought drinks for military guys. He was in his 30's and I was 19. After couple of drinks he ask if I would join him in a booth, we moved and I got in one side of the booth and to my surprise he slide in beside me. Soon he put his hand on my lap and gave my cock a squeeze and ask if it felt good, I told him yes it felt great. After a few more drinks he ask if I wanted to go to his place. I did not have a car so I rode with him and he massaged my cock the whole trip. In his house he poured me a strong drink, I had a good buzz on and sat on the bed and ask me to join him. I did and he pulls some porn mags out, laid back on the bed and he ask me to remove my cloths. I took everything off and laid back on the bed watching him remove his cloths, he got completely nude and sat beside me. Looking at the mags I began rubbing myself. He said let me help and he began pulling my underwear off and as he did he took my cock in his mouth. After a bit I turn my body around and began sucking him. It was great both of us were ...... and soon I came in his mouth, stopped sucking him and jacked him to get his cum, which he sprayed on my face. We lay there for a bit and I felt him slide down a bit a he began licking my ass. I was not into that so I sat up, he remained laying on his belly, and ask me to play with his ass and cock. I was massaging his ass cheeks and reached under him grabbing his cock which was semi hard. He reached back spit on his fingers and put it on his ass and ask me to use my fingers on him. Stopped the massage and playing with his cock and he bowed up as i put a finger in his ass, then two then three. He was in his knees rocking back in my fingers and I was as hard as 19 year old could get. I was on my knees in front of him and he began sucking me off again. He got me good and wet and turned around and ask me to fuck him, was so hot I went for it. I had forgotten how good it felt as it had been years since I last played with my cousin, I was pounding his ass hard and after a while I told him I was about to come, was about to pull out and he reached around and pull me deep into him as I came like a 19 year old. We got up and showered then for the rest of the night we sucked and I fucked him two more times. We got together a few times before I left for Nam, always very hot and sexy.
The last guy I played with was with CCC, we were at an ABS with glory holes. In a booth CCC and I began playing and a very nice BBC poked through the GH. CCC took him between her lips and took him in her mouth.
20130831_020607 2.jpg
20130831_020555.jpg20130831_020549.jpg
After she began sucking on him I got behind her rubbing my cock over her pussy and ass, she pulls the cock from her mouth points it at me and said,"Suck it". I got on my knees took his cock in my hand, it was definitely a BBC and it was at first stretching my mouth, but adjust quick and began trying to get as much of his cock in my mouth as I could. I had a good rhythm going but CCC said I want his cum so I backed away and she took him as deep as she could get him as he began cumming, actually so much that she could not hold it all as I could see it coming out of both sides of her mouth. The cock disappeared from the GH and I sat back, she sat on me reverse cowboy. I was pounding her good, I looked at the GH and the black guy was watching us. I spread her my legs some so he could see my hard cock pumping her pussy hard.
As we left the black was sitting in the lobby, he came over to CCC wrapped his arms around her and was playing with her ass and thanked us both for a great time.
 
My first time was in high school with my life long best friend. Started with looking at porn on sleepovers and touching each other which lead to sucking each other and one night we finally agreed to “practice for girls” and we fucked all night like rabbits.

He was a perfect little twink with an amazing bubble butt and after a few fun nights he became the permanent bottom and would come over once a week after school and I’d pound him 3 times before he would go home.
 
For me it was in middle school. I used to walk with my buddy to his house after school. We started looking at porn mags together. Then eveventually started jacking off together. That progressed into jacking each other off, then sucking each other off. Eventually, I would try to put it in his ass, but we didn't know anything about lube, so couldn't make it work.
Same exact thing for me! Finally I found out about vasoline and I couldn’t get enough of his ass
 
Mine was in my teens - 14/15. My best friend suddenly one day announced to me that he was gay and really fancied me. He tried kissing me but I pushed him away. At the time I thought I only liked girls, but over the next few days I kept thinking about it, and when I did I got hard at the idea. So a few days later I asked him about it and told him I kinda liked the idea. So
We started kissing - and kept kissing for ages. We could both feel each other becoming aroused in our shorts. That first time we ended up wanking ourself - probably too nervous to do anything. Over next few weeks we progressed to stroking each other’s cock and then sucking.

Like a previous poster, we tried fucking a few times but didn’t really work - just ended up cumming over the other kids hole.

Lasted (in secret) for a few years until he had to move away when his dad was stationed overseas. Never saw him again - 40yrs ago.
 
Mine was in my teens - 14/15. My best friend suddenly one day announced to me that he was gay and really fancied me. He tried kissing me but I pushed him away. At the time I thought I only liked girls, but over the next few days I kept thinking about it, and when I did I got hard at the idea. So a few days later I asked him about it and told him I kinda liked the idea. So
We started kissing - and kept kissing for ages. We could both feel each other becoming aroused in our shorts. That first time we ended up wanking ourself - probably too nervous to do anything. Over next few weeks we progressed to stroking each other’s cock and then sucking.

Like a previous poster, we tried fucking a few times but didn’t really work - just ended up cumming over the other kids hole.

Lasted (in secret) for a few years until he had to move away when his dad was stationed overseas. Never saw him again - 40yrs ago.
This got me rock hard! My first time I finally was able to get in my friend I was on top and after a couple of minutes a went to kiss him and he turned away saying “that would be gay”. I was like “dude I’m literally fucking your ass right now.” We’re past gay and he laughed and we started kissing”
 
This got me rock hard! My first time I finally was able to get in my friend I was on top and after a couple of minutes a went to kiss him and he turned away saying “that would be gay”. I was like “dude I’m literally fucking your ass right now.” We’re past gay and he laughed and we started kissing”
Great! I still get hard thinking about it.

After he moved away I convinced myself it was just a one-off and dated a few girls. Then in college I was really good friends with a guy - and we both had girlfriends. He invited me down to his parents house one weekend, but his family were away. He made up some BS excuse about us only being able to ...... in one bed. Innocently I just accepted it. Then I woke up in the middle of the night I realised he was lying up against me and his hand was on my belly. Immediately I started to get hard - he must have felt me shift or something and his hand slid down into my shorts and he started stroking me. I reached over and discovered he was already naked and had a huge boner - he had one of the most beautiful cocks I’ve ever had. Very quickly we were kissing and holding each other tight our cocks rubbing against each other. I sucked him off first and then he drained me.

Spent the whole weekend in bed after that. And from then on we’d play with each other regularly. Still had our gf’s who never knew. Even when we were both married we’d still meet up for a “boys” weekend. Wives thought we were playing golf!
 
Great! I still get hard thinking about it.

After he moved away I convinced myself it was just a one-off and dated a few girls. Then in college I was really good friends with a guy - and we both had girlfriends. He invited me down to his parents house one weekend, but his family were away. He made up some BS excuse about us only being able to ...... in one bed. Innocently I just accepted it. Then I woke up in the middle of the night I realised he was lying up against me and his hand was on my belly. Immediately I started to get hard - he must have felt me shift or something and his hand slid down into my shorts and he started stroking me. I reached over and discovered he was already naked and had a huge boner - he had one of the most beautiful cocks I’ve ever had. Very quickly we were kissing and holding each other tight our cocks rubbing against each other. I sucked him off first and then he drained me.

Spent the whole weekend in bed after that. And from then on we’d play with each other regularly. Still had our gf’s who never knew. Even when we were both married we’d still meet up for a “boys” weekend. Wives thought we were playing golf!
That’s so awesome! We continued fucking through high school with him becoming a permanent bottom. Sleepover nights and once a week after school with a couple of times in college and nobody ever knew until we were both married and during a party night told our wives!
 
  • Like
Reactions: nicebiguy
WOW! How did that go down with the wives? You told both wives at same time??
Yes! They grew up together and the wives had hooked up in their younger days too. And during a night at the house they were saying they were closer friends because they had been together sexually which me and my buddy would never understand.

My buddy and I exchanged looks and I blurted out “we had sex over 100 something times”. The girls were floored and didn’t believe us one bit. We gave detailed stories and they were aroused and stunned.

So we should them what we used to do…
 
Yes! They grew up together and the wives had hooked up in their younger days too. And during a night at the house they were saying they were closer friends because they had been together sexually which me and my buddy would never understand.

My buddy and I exchanged looks and I blurted out “we had sex over 100 something times”. The girls were floored and didn’t believe us one bit. We gave detailed stories and they were aroused and stunned.

So we should them what we used to do…
Awesome. And did they reciprocate and out on a show for you?
 
In my mid 20s and single i went almost every night to a strip bar. I dated for a relative long time one of the strippers and it was fun. When we broke up, she left me, in order to make her angry I fucked with every woman that went there. I was determined to do so. For half a year i missed the bar and when I got back the same old human beings were there except a tall and good loking one. I went for "her" not knowing it was a "him". In bed I was told "she " had her period so we should have anal sex. I gave him the fuck of his life. Next night when I went to the bar every single human there made fun of me because I had fucked a man.
 
  • Like
Reactions: nicebiguy