Do You Remember The First Time You Had Sex And With Whom?

[+ Hoover42]

Damn! Did they know about each other all being with you, or was it all secretive?.

 

Apparently, my friend told the next oldest brother about me right away, because just a few weeks later, the older brother convinced me to invite him over the weekend! They were the only two who knew about our secret for quite awhile. It wasn't until I was 15 when the news got out to the other brothers.

 

Eventually, one of them found a diary that I had been keeping where I described my fun weekends in great detail and suddenly the cat was out of the bag. From then until graduation I had all the dick I could handle.

 

Sadly, the first brother felt I had betrayed him with that stupid diary (he was right!) and he was furious with me from then on; he actually tricked me to come see him one night soon after with a plan to beat me up. Luckily, he ended up just yelling at me for ten minutes. Ten years later I discovered he had become a Baptist minister!

[bostonman]

Apparently, my friend told the next oldest brother about me right away, because just a few weeks later, the older brother convinced me to invite him over the weekend! They were the only two who knew about our secret for quite awhile. It wasn't until I was 15 when the news got out to the other brothers.

 

Eventually, one of them found a diary that I had been keeping where I described my fun weekends in great detail and suddenly the cat was out of the bag. From then until graduation I had all the dick I could handle.

 

Sadly, the first brother felt I had betrayed him with that stupid diary (he was right!) and he was furious with me from then on; he actually tricked me to come see him one night soon after with a plan to beat me up. Luckily, he ended up just yelling at me for ten minutes. Ten years later I discovered he had become a Baptist minister!

 

Quite an intrigue, lol. ;-)

 

I'm PM'ing you if that's ok...

[+ Gar1eth]

I was 41. It was with an escort that I can't think of the name of right now. He even had to teach me to Fr kiss.

 

Gman

[P Gren]

The summer after my tenth birthday, an older friend and I were having a sleepover at my house (trailer, actually) all weekend. For fun, I devised a fantasy where the two us had superpowers and were hunting an evil force out to destroy civilization. We played this game all weekend, and were pretty much in character the entire weekend. At one point, my friend and I were trapped by the evil force and I was compelled through some invisible force to suck his dick for a few minutes before I managed to free myself from the compulsion and disable the force that was binding him to the bed.

 

We played this game many times over the remainder of the summer.

 

p.s. He was one of seven brothers, all but the youngest of whom I managed to suck off before I graduated high school.

Sounds like "hoover" is a name you came by honestly

[+ bashful]

When I was 9, no more than 10 years old. There was an older kid who lived down the street. He was about 12, maybe 13. It was 50 years ago, so I don’t recall a lot of details, what happened first, or the sequence of events, but I remember 3 things. Whether true or false memories, I can’t tell you.

 

One was we were in his room (a basement bedroom) and we were on his bed, and each of us had our hands down the other’s pants fondling each other. I didn’t know it at the time, but I think what I felt from his dick was precum. I don’t remember thinking that anything we were doing was wrong.

 

Another time, he wanted me to watch when he took a shit. He squatted away from the toilet, towards me, and I saw it just beginning to slowly come out, then, he turned around and sat on the toilet, and I left the bathroom.

 

The other time I remember, it was summer, and we were in his pool (one of those 2-3 foot above ground pools that never lasted for more than a summer). His parents were sitting in lawn chairs about 20 feet away, and his mom was talking to us. We were both at the edge, facing them, next to each other, just our heads above water. He put his hands in my bathing suit, and I in his, all while he was talking to his mother.

 

From that point, all my experiences were with women. I enjoyed them. It was not until almost 60, I decided to “try before you die”, and experience and adult man/man experience, when I also hired for the first time. And yes, I enjoy them too. However, as of this post, I’m still an anal virgin.

[+ Gar1eth]

I was 41. It was with an escort that I can't think of the name of right now. He even had to teach me to Fr kiss.

 

Gman

I just remembered his name. It was former porn star Dallas Taylor although long after his glory days. At the time he had the largest tallywacker I had ever seen in person. And even after all my experience, I think he'd still be among the largest.

 

 

Gman

[BaronArtz]

With a priest. His name was father John. At boarding school in Belgium. I was about 11. He gave me a glass of brandy, a cigar then he unzipped his pants and showed me his cock. He then masturbated while he fondled my ass (I had my clothes on). There was no other interaction. I don't know if this qualifies as 'sex' but I didn't forget it - and I am 58 now.

[Chuckball]

I was visiting a friend at his parent's cottage. We were both 16 and had earlier in the evening double dated with some girls in the area. Upon our return we found the parents had overnight unexpected guests. My friend and I had to share a bed. We started by asking if one another had ever slept in the nude. That led to us taking off our undershirts and eventually comparing dick size by touch. Both of us were rock hard. We decided we would explore each other further. We went into a 69 position and my friend suggested I put my mouth around his penis. As soon as I did I shot my load all over his face. Within a few seconds he unloaded on me. We quickly cleaned up and never talked about the incident again.

[OCClient]

I did not have sex with that woman!

 

Well I guess I'll count sitting on the couch in his dorm room, lights off. I was his pal. Watching TV with the lights off, he'd curled up to recline so I eased his legs over, stretching his legs out onto my lap. I was in lust with him, but I loved him too, his prince valiant looks. Starting to pet his legs, and continued stroking up to his thighs. He had gym shorts on and a jock. My hand had a mind of it's own and soon found it's way further and further until eventually I reached his velvety smooth skin of his beautiful rump. I enjoyed that real estate for a while but finally continued on to his cock, brushing against it through the pouch of his jock. In the dim light of that little TV I saw his eyelids open and look at me. Then I stopped. I wish he would have reached for my hand and brought it back to him. A few years later he wanted to re-enact that night on the couch in his basement, but I was in a different place and was done playing with straight guys.

Edited October 3, 2017 by OCClient

[+ Italiano]

With a priest. His name was father John. At boarding school in Belgium. I was about 11. He gave me a glass of brandy, a cigar then he unzipped his pants and showed me his cock. He then masturbated while he fondled my ass (I had my clothes on). There was no other interaction. I don't know if this qualifies as 'sex' but I didn't forget it - and I am 58 now.

 

Bastard. (The priest, not you)

[bostonman]

Well I guess I'll count sitting on his the couch in his dorm room, lights off. I was his pal. Watching TV with the lights off, he'd curled up to recline so I eased his legs over, stretching his legs out onto my lap. I was in lust with him, but I loved him too, his prince valiant looks. Starting to pet his legs, and continued stroking up to his thighs. He had gym shorts on and a jock. My hand had a mind of it's own and soon found it's way further and further until eventually I reached his velvety smooth skin of his beautiful rump. I enjoyed that real estate for a while but finally continued on to his cock, brushing against it through the pouch of his jock. In the dim light of that little TV I saw his eyelids open and look at me. Then I stopped. I wish he would have reached for my hand and brought it back to him. A few years later he wanted to re-enact that night on the couch in his basement, but I was in a different place and was done playing with straight guys.

 

I had mentioned that I had a few little encounters with a friend named Tim when I was 13 or so. Your story reminds me a lot of something that happened with him - I think it was the first time we experienced any sort of intimate touching. And it's probably a moment that led him to try seducing me a few times later on - though looking back on what happened with Tim, it's amazing to me that we didn't go further. One of the big regrets of my life that I somehow didn't encourage him more, lol.

 

Anyway - we're at Tim's house, watching TV on a couch in the basement recroom. It was summer, and we were in shorts, so his legs were exposed. He was sitting cross-legged, so one of his feet (he had sneakers and socks on) was right near me. I'll never know what my impulse was here, but at one point I somehow started working my hand under his sock and just kind of rubbing underneath. Nothing was said between us, no eye contact - and I do seem to remember wondering what the hell I was doing even as I was doing it, lol. But I was doing it, and he wasn't stopping me. Eventually I stopped and took my hand away.

 

And that was it.

 

It could be that he was as surprised by the touch as I was (especially being such an odd choice of places to touch him, lol) and just didn't know how to react to it. Given that we did try to do more fooling around in the future, he certainly wasn't offended by the touch. Maybe he was too afraid of being caught if we started something more, with his parents upstairs. Maybe he just wasn't sure what he wanted. Maybe it's just that we were both 13 and so unsure of ourselves (though I tend to think that Tim was more sexually curious, and possibly more experienced, than he let on).

 

But, it's one of those sweet moments I'll never forget. And I do fantasize about it...always wondering what would have happened if he had encouraged me to rub him some more, etc. (As an adult, I do have a foot fetish. Back then, I wasn't aware of it. But it would have been fun to imagine me getting to explore Tim's feet, lol...who knows?)

[BasketBaller]

A girl I'd known all my life and I decided at 14 or so that we would be boyfriend and girlfriend. She was the daughter of family friends and we'd played together ("play" as in childhood play) as long as we could remember, and we were very comfortable with each other. I think my rationale was to impress my friends, in part, as well as to further suppress any inkling that I liked guys. So we were a "couple," which didn't mean much, I don't know that anything was different. But eventually we decided we should be more romantic, and we started kissing when we were alone. It was very experimental, and there was lots of laughing and asking each other what worked best, but we got so we were pretty seriously kissing. And from there to touching, first through clothes, then putting hands under shirts or down pants. More than once I had to stop her before I came, and finally didn't stop her in time and came with her hand on my dick. I remember being so embarrassed but she was fascinated, and wanted to know what it felt like-- as I began to shoot she thought I was in pain. The next time we were alone at her house we got naked and the intent was to make out, and I was able to learn more about female anatomy and what made her happy. But having gotten to that point we figured we should go al the way, and we fucked. I came very fast, but really never got soft, and a second round lasted longer. (No condoms, stupid kids!) There was no turning back from that, and we fucked whenever we had the opportunity for a few months, practicing and assessing what each of liked best. Then we both decided that we were having fun but not in love, and gradually moved on to dating others for real. But I know I was a better lover because we'd been so open with each other. When I started sleeping around a lot, again mostly to impress my buddies, she told me she was worried about me, and that slowed me down a little because I trusted her.

 

We're still in touch through our families, and I consider her an old friend.

 

The first time with a man was when I was 31, after I had accepted my attraction to guys, and after several years of watching gay porn and getting more and more curious about bottoming, I hired an escort to fuck me with the idea that I'd get it out of my system and could move on. I was turned on by hung guys in porn, so I, perhaps unwisely for an anal virgin, hired John from Atlanta aka Smalltown John. But he was so skillful and sensitive, that while it was hard to take at first, I left his hotel room with it very much NOT out of my system, I knew I wanted more.

Edited October 2, 2017 by BasketBaller

[mike carey]

I was turned on by hung guys in porn, so I, perhaps unwisely for an anal virgin, hired John from Atlanta aka Smalltown John.

Well, you didn't accept any sort of half measure. I have looked at his ads and mused about meeting him. Kudos, bb!

[BasketBaller]

Well, you didn't accept any sort of half measure. I have looked at his ads and mused about meeting him. Kudos, bb!

He's a great guy. I think I was subconsciously setting myself up to hate it, so I could continue hiding my urges. I remember the surprise of how hard a man's body is compared to a woman's, and the scratchiness of his face when we kissed despite his being clean-shaven. When he entered me I did hate it, and almost stopped him. But ironically, since it was "just trying it one time," I figured I'd tough it out. As he began to fuck, the experience was mind-blowing, painful but sensations I'd never felt before too. It got better and better until he moved me onto my back, and even with some pain, it felt incredible. I don't think I was very cogent at the time, but I look back on that moment as the point I knew I was a bottom.

 

Part of the reason I'd put it off so long was a perception that bottoming is submissive, which didn't appeal. But in the moment it didn't feel submissive, it felt like mutual pleasure, and as I said, I left reeling with emotions but very aware that it was right for me.

[+ Avalon]

Here is John's info

 

https://rent.men/John_Atlanta

[+ poolboy48220]

I've seen John a couple times but after some bad experiences in Detroit (lots of guy cancelling/flaking on him), he doesn't come here any more. Sad.

[+ poolboy48220]

In the vein of early missed experiences:

 

In my early 30's, I met a co-worker at a work outing (ok, the company bowling league) and thought he was hot - looked a bit like tom cruise (like he looked then, in the 80's). We became friends, and a couple what-I-think were missed chances....We hung out in his basement apartment one night, both wearing nothing but the lycra shorts popular for workout then. We laid on his bed and watched "Dangerous Liaisons". I was wondering, and tempted, but still way too much in the closet to initiate anything. Another time, we were part of a group renting a condo for a ski trip, and he & I would be the first ones there; he mentioned a couple of times looking forward to hot tubbing naked; which we did, but nothing happened. We were also the last ones there, but still, nothing happened. He'd mentioned being friends with the gymnastics team in college & working out with them, I had fantasies of what went on after the workouts.

[manorbrown]

I was 15-16 years old and was one of the managers on the high school football team...one of the wide receivers on the team was legendary for his large penis (his nickname was Big D (his name was Dennis but he was only 5' 7"...))... I would always try to take a look at it in the locker room but never saw it...one day after practice I caught him in the woods smoking weed...he grabbed me and started cursing and threatening me with bodily harm if I told the coach...thought he was about to whip my ass but he looked at me with a strange look and said something like "oh, I see what you like/are.." and he took his penis out....and the rumors were true...it got hard quickly and i sucked it until he came...I'll always remember how much cum he had...damn near overflowed my mouth...also, I'm almost 60 years old and have dated many men but don't think I've ever seen a penis as big as his...it was long and thick...of course immediately afterwards he threatened to kill me if I ever told anyone so I spent the remainder of the school year avoiding him as much as possible....

[+ José Soplanucas]

I was 15-16 years old and was one of the managers on the high school football team...one of the wide receivers on the team was legendary for his large penis (his nickname was Big D (his name was Dennis but he was only 5' 7"...))... I would always try to take a look at it in the locker room but never saw it...one day after practice I caught him in the woods smoking weed...he grabbed me and started cursing and threatening me with bodily harm if I told the coach...thought he was about to whip my ass but he looked at me with a strange look and said something like "oh, I see what you like/are.." and he took his penis out....and the rumors were true...it got hard quickly and i sucked it until he came...I'll always remember how much cum he had...damn near overflowed my mouth...also, I'm almost 60 years old and have dated many men but don't think I've ever seen a penis as big as his...it was long and thick...of course immediately afterwards he threatened to kill me if I ever told anyone so I spent the remainder of the school year avoiding him as much as possible....

Shhhh, you just told. You may need to enter the witness protection program.

[+ Gar1eth]

He's a great guy. I think I was subconsciously setting myself up to hate it, so I could continue hiding my urges. I remember the surprise of how hard a man's body is compared to a woman's, and the scratchiness of his face when we kissed despite his being clean-shaven

 

In the interests of full disclosure, I must unfortunately admit that my body is pretty soft. Having a physique like Wimpy from Popeye will do that to you. I do however usually have a beard-and even when clean shaven am at least a little scratchy.

 

But scratchy is all to the good. My neck is one of my erogenous zones. Feeling a man's beard or 5 o'clock shadow on my neck during foreplay usually sends tingles down my body.

 

Gman

[Good Grief]

Shhhh, you just told. You may need to enter the witness protection program.

 

[BaronArtz]

Bastard. (The priest, not you)

 

Indeed. Thank you for your comment. Now that I reflect on this, it would have been totally UNTHINKABLE for me to discuss this with my parents. Can you imagine?

[+ Gar1eth]

I just remembered his name. It was former porn star Dallas Taylor although long after his glory days. At the time he had the largest tallywacker I had ever seen in person. And even after all my experience, I think he'd still be among the largest.

 

 

Gman

 

He was definitely older when I saw him. The strange thing is that now when I think back 15 years-and just by coincidence October is my loss of virginity month-my recollection of what he looked like is that of a blond Robin Williams although not quite as hairy.

 

yeah, pretty rare, I'd presume, because of almost all of us having regular wet dreams at age 13/14 ?? before ever messing around with somebody else......

 

I remember, as I felt a wet dream coming on in my sleep, trying to quickly wake up for good so I could enjoy the feeling while really awake and aware......never really made it in time!

 

My wet dreams would usually disturb me having an erotic dream-most likely just kissing a handsome guy in my dream (is that gay?). When I came, I would unfortunately wake up.

 

 

Gman

Edited October 3, 2017 by Gar1eth

[+ poolboy48220]

A friend told me about "Lucid Dreaming", I bought a book on it with the express intent of seeing if I could make myself have more erotic dreams. I never finished the book, no more so than I did "Meditation for Dummies".

[+ Italiano]

 

My wet dreams would usually disturb me having an erotic dream-most likely just kissing a handsome guy in my dream (is that gay?). When I came, I would unfortunately wake up.

 

Gman

 

Oh man those wet dreams!

It was such an amazing feeling until waking up and realizing that that hot guy wasn't really kissing you and/or touching you all over!

And on top of that, had to deal with the annoying glueish feeling in your pajama pants and having to decide if to get up from bed and clean up, or go back to sleep and deal with that sticky mess in the morning....

I think I had my last one in my 30s.