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Pleasant surprises and disappointments in first gay experiences

Travler99921 said:
I was a late bloomer. I was over 50 when I had my first gay encounter. I was surprised how much I enjoyed some things while other things were disappointing. I could not believe how good it felt just to touch another man's cock. I expected to enjoy having my cock sucked, but it was much better than I expected. The same was true of sucking another man's cock. After the first time there was no doubt I was a cocksucker.

The biggest disappointment was 69. It was not bad, but I much preferred taking turns. Kssing a man was another disappointment.


I am not sure if it was a disappointment or a blessing, but I failed to develop any emotional connections with my male sex partners. That is true to this day. There was sometimes a bit of an afterglow, but it did not last long. I remain hetroromantic to this day.
Click to expand...
Like you I never formed a relationship with my male partners though I enjoyed our encounters very much and repeated our encounters often. I was in love with the act not the person.
 
My first time being sucked by a stranger happened during a hitchhiking trip. After some suggestive conversation about gay sex, he propositioned me, I replied I was curious, ready and willing to try sex with him, and especially if we could do 69. But once we got undressed and in bed in the middle of the afternoon, I was too nervous to get an erection. He was horny as hell, and humped my leg and dribbled on me as he sucked my limp dick. I didn't like that at all, so I didn't suck him, and we both left unsatisfied.
Disappointments 1) That my nerves overcame my desires, resulting in a limp dick

Next time, with a different guy, after a few drinks at his apartment, we undressed each other. I found out that I love chest hair on a man, and ran my fingers through it. He wanted to kiss but I didn't. I was hard as a rock, and he stroked me while rimming me. I'd never had my ass licked before, and I loved it, but I pulled away when I was about to cum, I'm not sure why. After a few times of edging me to near completion, he crouched over me, and positioned his hole over my cock, as if to tease me with his ass, back and forth over my cock head. I could only tolerate that for so long before I grabbed his ass and thrust my cock straight into him, and fucked him agressively. I came hard and fast, and he seemed to like it but he later complained that I was too forceful, and he thought he was bleeding. I spent the night, and he took me out for breakfast in the morning.
Surprises 1) how good rimming felt 2) That men enjoyed anal sex, and so did I, at least as a top (bottoming came later) 3) chest hair is sexy
 
Early 30s, late bloomer. Dead marriage.
Saw a gay guy wanting to suck married men.
His place he'd be waiting naked.

I'd not had a blowjob in 5 years and sex was annually at best.

I entered, a bit apprehensive.

He instructed me to undress. Work shirt unbottoned.

He then proceeded to give me an absolutely amazing blwo job, taking 20 minutes or more.

I came so hard I nearly blacked out.

After that, I was hooked on finding bottoms who just needed dick.
 
Hitchiker69 said:
My first time being sucked by a stranger happened during a hitchhiking trip. After some suggestive conversation about gay sex, he propositioned me, I replied I was curious, ready and willing to try sex with him, and especially if we could do 69. But once we got undressed and in bed in the middle of the afternoon, I was too nervous to get an erection. He was horny as hell, and humped my leg and dribbled on me as he sucked my limp dick. I didn't like that at all, so I didn't suck him, and we both left unsatisfied.
Disappointments 1) That my nerves overcame my desires, resulting in a limp dick

Next time, with a different guy, after a few drinks at his apartment, we undressed each other. I found out that I love chest hair on a man, and ran my fingers through it. He wanted to kiss but I didn't. I was hard as a rock, and he stroked me while rimming me. I'd never had my ass licked before, and I loved it, but I pulled away when I was about to cum, I'm not sure why. After a few times of edging me to near completion, he crouched over me, and positioned his hole over my cock, as if to tease me with his ass, back and forth over my cock head. I could only tolerate that for so long before I grabbed his ass and thrust my cock straight into him, and fucked him agressively. I came hard and fast, and he seemed to like it but he later complained that I was too forceful, and he thought he was bleeding. I spent the night, and he took me out for breakfast in the morning.
Surprises 1) how good rimming felt 2) That men enjoyed anal sex, and so did I, at least as a top (bottoming came later) 3) chest hair is sexy
Click to expand...
That's funny-I didn't realize that I'd find chest hair sexy either until I played with my most recent buddy. I had played with a few other guys previously, but no one that had any sort of significant amount of chest hair until my most recent regular guy. I really find it a turn on to run my hands through it and feel it against me when we are having body contact!
 
I wasn't expecting that the first time I kissed a man it would feel like kissing my dad. Reminder of when I was so young that I still kissed both of my parents goodnight.

I don't know why kissing girls didn't remind me of mom but, that first time, being reminded of my dad's stubbly face was... not thrilling.
 
bijedi said:
I am often surprised at how bad men are at kissing. I think most men would become better at this if they had regular make out sessions with other men.
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So true… but then I wonder if I’m biased because I am so into the softer, more sensual kiss of a woman…
No, most men actually do suck at kissing.
Maybe because they consider it the obligatory requirement of their partner before the cock play begins?
 
well it was my first experience with these guys, I had just met one of them, he invited me to his place. My plan was to give him a blowjob. His roommate was there with two friends, they all wanted to join in.

I found myself naked in front of four guys I had only just met. They could have been a little more kind but we were all horny. They slapped my cock, pinched my buns and said some kind of nasty things about me, the comments could have been worse though.

I found that I was more turned on than usual, although I don’t usually end up naked in front of this many people.

After I had given two blowjobs one of them stood behind me and jerked me off, while the others laughed. He brought me close to orgasm, then he would stop stroking me and they laughed even harder.

Finally the guy I had met earlier stopped stroking my penis and said, if you want to cum go ahead and jerk off for us.

I never realized how horny I would feel cumming while being laughed at.😋
 
I was 31 when I had my first encounter. He was 66. I was really nervous but also excited beyond belief. I liked everything except kissing. He insisted on that at first and I was repulsed, basically
 
First time sucking a guy, I was amazed how close to cumming I got without touching myself. I swallowed him and didn't want his dick to go soft so I sucked him off again. And was still wanting more. Hour or so later I sucked him off again. My dick was ready to pop but I didn't touch it just from sucking him and not touching myself.
 
There were many pleasant surprises for my first time with a guy that extended many, many times.

I met someone on here, we had some sex chats for a couple of weeks, and finally got together. We were both in our earler 40s, he was only with a couple of guys and looking for fwb. IU went to his place, and we had a few drinks talking about it our chats and other things. He was nice and we both felt comfortable chatting and slowly touching each other flirting. I was feeling better and he leaned for a kiss, i wasn't expecting it, but as we started to make out, it was getting so hot. as we go, he asked me to go to the bedroom, i of coursed agreed. he layed me on the bed on got on top of me. i was in heaven when he slowly made love to me; the smooth and thrusting got me to an amazing sex.

the disappointment was the first time we did anal as i thought i wanted it so bad and it would be amazing. It took us a few trys until we got the speed right and it was amazing.
 
rc1989 said:
First time sucking a guy, I was amazed how close to cumming I got without touching myself. I swallowed him and didn't want his dick to go soft so I sucked him off again. And was still wanting more. Hour or so later I sucked him off again. My dick was ready to pop but I didn't touch it just from sucking him and not touching myself.
Click to expand...
An hour or so later and you still hadn’t touched yourself ? I find that hard to believe
 
james2346 said:
There were many pleasant surprises for my first time with a guy that extended many, many times.

I met someone on here, we had some sex chats for a couple of weeks, and finally got together. We were both in our earler 40s, he was only with a couple of guys and looking for fwb. IU went to his place, and we had a few drinks talking about it our chats and other things. He was nice and we both felt comfortable chatting and slowly touching each other flirting. I was feeling better and he leaned for a kiss, i wasn't expecting it, but as we started to make out, it was getting so hot. as we go, he asked me to go to the bedroom, i of coursed agreed. he layed me on the bed on got on top of me. i was in heaven when he slowly made love to me; the smooth and thrusting got me to an amazing sex.

the disappointment was the first time we did anal as i thought i wanted it so bad and it would be amazing. It took us a few trys until we got the speed right and it was amazing.
Click to expand...
I had my own dildo for months so I was ready for the real thing. My partner used a dildo on me and it was the same as mine. Then he used a plug which wasn’t bigger than a Christmas bulb. He pulled it out and I thought he graduated to a larger dildo but then l felt his hands on my hips. It was the real deal! Felt fantastic.
 
Ciceri said:
I had my own dildo for months so I was ready for the real thing. My partner used a dildo on me and it was the same as mine. Then he used a plug which wasn’t bigger than a Christmas bulb. He pulled it out and I thought he graduated to a larger dildo but then l felt his hands on my hips. It was the real deal! Felt fantastic.
Click to expand...
Wow, sounds great!

We were finally got to the point, allowing me on the bottom, spreading my legs, him slowy interesting me and going slowly with his grabing my hips and me humping him
 
james2346 said:
Wow, sounds great!

We were finally got to the point, allowing me on the bottom, spreading my legs, him slowy interesting me and going slowly with his grabing my hips and me humping him
Click to expand...
So you were flat on your back? I would have liked that, too. I was hooded so I couldn’t see anything anyway. I’m shy and he knew eye contact might inhibit me. But I did love his hands on my hips and then on my shoulders as he repositioned himself. I’d never turned on another man like that. He was so into it - sweating and breathing hard. It felt great to bring a man to orgasm just by offering my body
 
Ciceri said:
So you were flat on your back? I would have liked that, too. I was hooded so I couldn’t see anything anyway. I’m shy and he knew eye contact might inhibit me. But I did love his hands on my hips and then on my shoulders as he repositioned himself. I’d never turned on another man like that. He was so into it - sweating and breathing hard. It felt great to bring a man to orgasm just by offering my body
Click to expand...
Yes, i was lying flat on my back. I felt fully comfortable, and we were both so turned on that made it even more exciting.
 
Travler99921 said:
I was a late bloomer. I was over 50 when I had my first gay encounter. I was surprised how much I enjoyed some things while other things were disappointing. I could not believe how good it felt just to touch another man's cock. I expected to enjoy having my cock sucked, but it was much better than I expected. The same was true of sucking another man's cock. After the first time there was no doubt I was a cocksucker.

The biggest disappointment was 69. It was not bad, but I much preferred taking turns. Kssing a man was another disappointment.


I am not sure if it was a disappointment or a blessing, but I failed to develop any emotional connections with my male sex partners. That is true to this day. There was sometimes a bit of an afterglow, but it did not last long. I remain hetroromantic to this day.
Click to expand...
I went to a sauna aged 22, really really enjoyed sucking cock. Also loved being naked, I’d always been paranoid about my size till then.
Biggest disappointment, that day and anytime since I’ve never managed to get fucked( despite trying several times!)
It’s an itch I fear I’ll never scratch cause it’s just too sore!
 
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