Straight guys; what was your first experience experimenting with a guy?

[foundacoolsite]

I'm thinking in-person. Curious for the stories, if any. Did you decide it wasn't for you? Gone back for more? Or just a fond memory in the rear-view?


For me, I was 20. (29 now) I was in college and I stumbled onto a reddit post about a dude who had been done a lot of uh, work, for pay through craigslist. It was an AMA. He was straight, and he talked about how shocked he was that guys wanted to suck him off. He felt like he should be paying them. He was adamant, "you gotta screen for crazies, meet up in person, be okay with saying no if they start asking for weird stuff". I didn't wanna do anything for pay, but I thought one day "I could try this. Nothing is stopping me. Apparently dudes want this." I got an app (wasn't about to brave craigslist) and chatted with people. One guy was respectful enough to take it slow. I was very clear, not trying to do anal stuff or anything. Surprising how much that pissed some people off. Anyways, the one guy chatted with me for several days. I didn't have the courage to actually pull the trigger for a while. This guy was older than me, maybe 40 something, super built, smaller dick tho, and I think he liked the idea of a college guy getting a new experience. Maybe he liked my dick. No idea. he was patient. Finally one day I texted and said I wanted to try something. He had me over, we went into his bedroom and he shut the door. Honestly I was so stupid, this guy could've been crazy or something. So he turned around, just dropped his pants and boxers, "well, what are you waiting for, get naked!" There was his dick, soft, just hanging there, getting hard. That was a first. I didn't really care too much, but want sure how these things were supposed to go, so I dropped my shorts. He really loved my dick. Again, I was just shocked by how easy it was to find a mutually beneficial meetup. I actually went the step further and we jacked each other some, but obviously I didn't know what I was doing so he stopped me and just told me to enjoy. Blew a load all over him, made a huge mess. I left, he smiled and waved, I got on with my day.

 

[hotguy88]

I had an online friend about a decade ago and we went on a trip together and pretty soon we were naked in the shower playing with each other's cocks

 

[hotguy88]

Then when I was in Vegas a couple years later I smoked weed for the first time and got my massive cock almost blown off my body by some dude on Grindr in my hotel room and that was the first time I ever had a screaming orgasm in my life and I've been hooked ever since on both although I still love tearing up some pussy

 

[theaveragedude]

Met a guy thru squirt. We still meet up, and I’ve become someone who really enjoys getting and giving head and being rimmed. Plus I discovered I’m vers, because I enjoy riding a hard cock now and then and well as topping a tight warm ass.

 

[hotguy88]

Now I'm doing fucking insane loud DP almost every weekend with my best friend on some tight pussy. No words. We both have absolutely massive orgasms inside her. Best sex I've ever had

And usually he sucks me off during the week

 

[zaratoga]

I love these tales.

 

[FrankieGuile]

I'm thinking in-person. Curious for the stories, if any. Did you decide it wasn't for you? Gone back for more? Or just a fond memory in the rear-view?


For me, I was 20. (29 now) I was in college and I stumbled onto a reddit post about a dude who had been done a lot of uh, work, for pay through craigslist. It was an AMA. He was straight, and he talked about how shocked he was that guys wanted to suck him off. He felt like he should be paying them. He was adamant, "you gotta screen for crazies, meet up in person, be okay with saying no if they start asking for weird stuff". I didn't wanna do anything for pay, but I thought one day "I could try this. Nothing is stopping me. Apparently dudes want this." I got an app (wasn't about to brave craigslist) and chatted with people. One guy was respectful enough to take it slow. I was very clear, not trying to do anal stuff or anything. Surprising how much that pissed some people off. Anyways, the one guy chatted with me for several days. I didn't have the courage to actually pull the trigger for a while. This guy was older than me, maybe 40 something, super built, smaller dick tho, and I think he liked the idea of a college guy getting a new experience. Maybe he liked my dick. No idea. he was patient. Finally one day I texted and said I wanted to try something. He had me over, we went into his bedroom and he shut the door. Honestly I was so stupid, this guy could've been crazy or something. So he turned around, just dropped his pants and boxers, "well, what are you waiting for, get naked!" There was his dick, soft, just hanging there, getting hard. That was a first. I didn't really care too much, but want sure how these things were supposed to go, so I dropped my shorts. He really loved my dick. Again, I was just shocked by how easy it was to find a mutually beneficial meetup. I actually went the step further and we jacked each other some, but obviously I didn't know what I was doing so he stopped me and just told me to enjoy. Blew a load all over him, made a huge mess. I left, he smiled and waved, I got on with my day.

Isn't the title of the thread a contradiction in terms? Or, is it a trick question with the only correct answer being, "never." Or, as the post in the Erotic Stories section would suggest, a fantasy?

 

[captaindarling69]

I found a guy on grinder who was in the same town. Met him on a bridge, said its my first time. He pulled out his soft girthy cock and tried to get himself hard. Stop I said, I like it like that. Got on my knees and began to suck his beautiful dick. I felt it throb in my mouth as I pushed my tongue into his foreskin licking and sucking his tip hard. Finally I had a cock to suck on for the 1st time. He grabbed the back of my head and began thrusting, I opened my throat and let him do as he wanted. Then I started to wank and suck him as he was getting bigger and harder. But to my surprise, he stopped me said he needed to get home because his boyfriend would be suspicious. I let him go and that was that. Can't say I wasn't disappointed though, I didn't want to be someone who helped him cheat, I didn't know until he said. And also really wanted to at least make him cum.... as he did say I was amazing at it before he left.

 

[TwinkCrush]

I found a guy on grinder who was in the same town. Met him on a bridge, said its my first time. He pulled out his soft girthy cock and tried to get himself hard. Stop I said, I like it like that. Got on my knees and began to suck his beautiful dick. I felt it throb in my mouth as I pushed my tongue into his foreskin licking and sucking his tip hard. Finally I had a cock to suck on for the 1st time. He grabbed the back of my head and began thrusting, I opened my throat and let him do as he wanted. Then I started to wank and suck him as he was getting bigger and harder. But to my surprise, he stopped me said he needed to get home because his boyfriend would be suspicious. I let him go and that was that. Can't say I wasn't disappointed though, I didn't want to be someone who helped him cheat, I didn't know until he said. And also really wanted to at least make him cum.... as he did say I was amazing at it before he left.

That’s weird. Was it really going to take him THAT long to cum? What a shame you didn’t get the load. Have you had better experiences since then? I hope so.

 

[678wsb]

Do you have any more stories?

 

[shilderia]

Plus I discovered I’m vers, because I enjoy riding a hard cock now and then and well as topping a tight warm ass.

I would crave to see you doing this (both things)

 

[lucasmate]

I was staying on the floor at my mates house one night. He got out of bed to use the bathroom, when he came back he stood over me legs on each side and he was naked , he then squatted on my chest with his dick right near my mouth and just said suck me off. Was my first time

 

[altaa_sa]

I was sucked off while drunk in bed at a house party. I didn't think much about it. The memory was always blurry. I vaguely remember "a head" under the sheets, the feeling of being sucked. We were sleeping in one bed. I remember walking to the bathroom to wash off dried semen and saliva from my cock and my belly not fully comprehending how I got it. I hate it that it happened. That pushed me into a closet for years.

 

[steveh9]

I went to a men's only bathhouse and was sucked by a guy there for the first time It was so great it made me want to suck a dick too. so I did, three of them, on my first visit there

 

[BC22x15]

A number of years ago I was regularly attending a swing club with my then girlfriend. From there I (not my then GF) received an invite to join male female couple for a hot tub at there place. Now I have had threesomes and more during the swing parties but never any interaction with the men. I perhaps should mention I have an uncut cock 8.5" x 6" circumference. I arrived and was offered a drink as we walked to the hot tub area. They both stripped naked and got in and I quickly followed. Both of them were on onside and I on the other side. The jets were running bubbling away obscuring the visibility in the water, I'd say within a minute I felt a hand grasp my semi erect cock, my first thought was "My she has a strong grip". I then looked up and he was smiling, she was a little out of reach for her to be gripping my cock, I then came to the conclusion that this may enter (pun intended) an area I have not been. He pulled himself over to me, lifted my now boner out of the water and started sucking while she watched. They both tag teamed sucking for about 5 minutes I think, hard to keep track of time..... Next stop was the living room where every position was sampled although I was not fucked, they just wanted me to probe their cavities with my cock.
I lost my anal virginity with another couple, she pegged me, he fucked me (not a big dick), had my first TRAIN position experience which I found wild.

 

[friskydawg]

Met a guy thru squirt. We still meet up, and I’ve become someone who really enjoys getting and giving head and being rimmed. Plus I discovered I’m vers, because I enjoy riding a hard cock now and then and well as topping a tight warm ass.

Thinking of the first time you got rimmed.......did the guy just dive into your hole unexpectedly or did he ask first? I guess what I am asking is, what it unexpected on your part? Did you go love it immediately?

 

[bar4doug]

Thinking of the first time you got rimmed.......did the guy just dive into your hole unexpectedly or did he ask first? I guess what I am asking is, what it unexpected on your part? Did you go love it immediately?

Completely unexpected, and no, I wasn't asked... and I sure as hell didn't complain.

Getting chubbed right now thinking about that day...

 

[luke_ttx]

I knew I was attracted to guys all my life. Growing up in the "bible belt" I fought my attraction to guys, got married, had kids, yada, yada. Then along came the internet and boom...awakened desires in me that I had been suppressing. Jerked to a lot of gay porn over the years buy left it at that. Then I downloaded Grindr and started chatting with guys but never went beyond trading pics.

Finally on a business trip one time, I got the balls to finally take the plunge and cross the line and meet up with a guy. I was in my mid-forties and he was a college student in his early 20's. I picked him up, we drove around and chatted a bit, then came back to my hotel. Chatted a while, then started making out. Very hot, passionate make out session. This moved to us slowly undressing each other, then taking turns doing oral to each other. First dick I had ever touched and gotten into my mouth. Plus his mouth was doing amazing things to my cock as well. We started to 69 and then he started rimming me. AMAZING feeling. I then started rimming him. We ended that night blowing our loads down each other throat. Then we went to sleep and held each other all night.

The next morning, I woke him up by suck on his soft cock while he slept. It got hard in my mouth and soon we were making out, trading oral, rimming each other like crazy. I asked him if I could fuck him and he said yes. I topped him and the sex was amazing.

Afterward, I took him back to his dorm then packed and headed for the airport to head home. Needless to say, I couldn't have asked for a better first experience. And it such a great first that it has now been far from the last.

 

[friskydawg]

Completely unexpected, and no, I wasn't asked... and I sure as hell didn't complain.

Getting chubbed right now thinking about that day...

Yes, it feels awesome. I was asking because I rimmed a straight guy once and he went crazy because it felt so good. Afterward, though he weirded out and kept saying "nobody has ever done that to me before". It was like he was having second thoughts (even though his reaction while I was doing it spoke for itself....literally) as a straight guy having let someone near his hole. I never saw him again (but would have since he had a great ass) and have always wondered if he craves having his ass eaten again and if he ever has. I hope that your hole has gotten lots more attention since that first time.

 

[friskydawg]

I knew I was attracted to guys all my life. As a kid, I picked all my friends based on how cute I thought they were and dated girls in high school if I thought they had a hot brother that I'd get to be around. Growing up in the "bible belt" I fought my attraction to guys, got married, had kids, yada, yada. Then along came the internet and boom...awakened desires in me that I had been suppressing. Jerked to a lot of gay porn over the years buy left it at that. Then I downloaded Grindr and started chatting with guys but never went beyond trading pics.

Finally on a business trip one time, I got the balls to finally take the plunge and cross the line and meet up with a guy. I was in my mid-forties and he was a college student in his early 20's. I picked him up, we drove around and chatted a bit, then came back to my hotel. Chatted a while, then started making out. Very hot, passionate make out session. This moved to us slowly undressing each other, then taking turns doing oral to each other. First dick I had ever touched and gotten into my mouth. Plus his mouth was doing amazing things to my cock as well. We started to 69 and then he started rimming me. AMAZING feeling. I then started rimming him. We ended that night blowing our loads down each other throat. Then we went to sleep and held each other all night.

The next morning, I woke him up by suck on his soft cock while he slept. It got hard in my mouth and soon we were making out, trading oral, rimming each other like crazy. I asked him if I could fuck him and he said yes. I topped him and the sex was amazing.

Afterward, I took him back to his dorm then packed and headed for the airport to head home. Needless to say, I couldn't have asked for a better first experience. And it such a great first that it has now been far from the last.

What an awesome introduction to man-on-man sex you had! It sounds like gay porn taught you a lot and you were able to jump right in. Good for you.