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

[+ Robster]

I can answer this question regardless of what the definition of having sex is.

 

I was 23 the first time I did anything with anyone. And we pretty much did it all that night.

 

He was about 20 years older than me. I subscribed to the local newspaper at the time, and he had written a letter to the editor that they had printed, responding to an earlier letter they'd printed from someone complaining about the "gay lifestyle". I still can't believe I did this, but I looked him up in the phone book and called him, to tell him how much I had enjoyed his letter. The first time I called, I chickened out and hung up when he answered, but the second time, I got up the courage to talk to him, and we had a really nice conversation, for quite a while. I mentioned that I was a virgin, and he invited me over to his apartment the following night. I can't believe I did this either, but I went, and wound up having sex for the first time. We did some things I really enjoyed, and some other things that I didn't, but I was just thrilled to finally be having sex with someone, lol. We had sex a couple more times after that, and remained friends for a few years.

 

Rob

[+ TheKnobGobbler]

Not counting the blowjobs I used to give to my cousins or to the couple of friends who sometimes stayed the night, my first time was during the summer of 1987 when I had just turned 14. I had been accepted to a state-run residential high school for gifted and talented students, but my dad was too cheap to help foot the tuition. So, I got myself a summer job to start earning the money to go to school. HE took the rest of the family on a week-long vacation to Disney World and left me home alone so I could take a cab to and from work. (I should preface the rest by saying that my dad was a monster who beat me and my brother so badly that there are photos of our welted and bruised butts on file in two different sherriff's departments.)

 

Two days before they were to return, on a Friday night in June, I got out the phone book, looked up the number of the only gay bar in our little city, and I called the bar, asking the bartender who answered, "Hi. I was wondering, are there any really attractive guys there tonight? Like an older guy? Maybe in his 30's?" He gave me a slow, quizzical reply and confirmed that there were indeed several men there matching that description. So, I asked if he could put one of them on the phone. He obliged.

 

Without knowing the first thing about this guy, I asked him if he was interested in popping the cherry of the neighboring town's Chief of Police's oldest son that night. He seemed pretty keen. So I gave him the address and waited nervously about 2o or 30 minutes for him to show up. When he did, I remember taking his hand at the door and leading him down the hallway through to my Dad's bedroom at the back of the house. We went in, undressed each other, and climbed into my Dad's atrocious 1980's king-sized waterbed with the huge, ornate wooden shelves for a headboard. That's where 14-year-old me took his first big ol' cock up the ass with the help of a totally perverted (hindsight is a bitch) 30-year-old statutory rapist. I *hated* it the first time. It hurt like fire. Maybe it was the cum he left in me that first go around that made the second time more enjoyable, but round 2 was everything I'd hoped for. Mission accomplished!

 

Dad and the step-fam got back that Sunday afternoon, each of them wearing their stupid mouse ears and looking like sunburned stupid. I just paraded around with a shit-eating grin on my face for pretty much the rest of that summer. I never told him his bed had laid the scene for his big, gay son's deflowering. I've been saving that little nugget of golden information for his deathbed. In case there's any chance the old bastard might pull through whatever finally gets him headed down the chute to hell, I want to be able to recount this story to him and help him shuffle off this mortal coil and reap his final reward for being such a remarkable father.

[+ quoththeraven]

The "what is sex" issue doesn't matter for me; I wasn't able to or interested in performing a blow job until my late 30s and the first time I was penetrated or had an orgasm with someone else's help happened in October of my sophomore year at college. A year later I'd also tried, and enjoyed, anal sex with a fellow student whom I dated for a year before an amicable breakup that didn't foreclose subsequent sexual encounters.

[Bargara Leatherboy]

I was 16 went to the bathhouse in my city, Saturday afternoon, got picked up by an older chub guy, no cabins or cubicles, but a group room, had some action, the earth did not move but I certainly became a regular.

[+ Italiano]

I was born and grew up in Milan. When I was 14-15 I used to go sometimes by myself to a seedy movie theatre where they showed straight porn movies.

One day in the dark a man sat close to me, I could feel his knee keep touching mine, I will never forget how my heart was pounding, I could feel his hand getting over my lap towards my crotch, I was hard as hell, and as soon as he touched my crotch I came inside my underwear and pants.

As soon as the lust of the moment disappeared I felt so shameful that I ran away. I realized I had a big stain on my jeans (always a big shooter here..), so before arriving home I threw some coke on it and told my mom I has spilled a soda on me ...No idea if she ever bought it, but she played like she did.

 

When I was 17 somehow I became acquainted with this married man in his 40s who owned a ties shop. We had a strong interest in common (opera), he liked to invite me to his shop and during closing time (at that time stores would close for lunch at least 2 hours) and play for me records of one particular opera singer he (and myself) loved. He was sort of an opera guru for me, telling me stories and teaching me to appreciate more and more opera.

It was quite clear he was attracted to me, I knew I was gay, never had sex so far and desperately wanted to, but honestly I wasn't attracted to him at all.

One day eventually he made his advances quite obvious and told me to go with him in the back store where he had some blankets on the floor, and of course everything happened. I remember I didn't particular enjoy the event, it also hurted to be fucked, and even if a bit shameful I was glad it finally happened.

I used to have girlfriends but nothing happened apart kissing and some mild fondling.

 

At last when I was 19 I went to Paris for 5 days in a hostel with two (straight, and totally unaware of me liking men) friends. It was my first trip abroad from Italy.

One day we decided to separate for few hours to do whatever each of us wanted. Of course I went to Pigalle, the "sex" area, and I went immediately to a gay movie theatre (my first!). A beautiful guy in his early 20s sat close to me, we began to touch each other (I had learned not to cum immediately!) and he invited me to his room in the University Campus where he was a temporary student, few blocks from there.

He was Hungarian, handsome sexy and hung, we spent 2 unforgettable fabulous hours. It was so intense that even if we never saw each other anymore we kept writing to each other.

I recently found him on Facebook, he is in his early 60s and he sent me a pic.....

I prefer to remember him as he was.

Edited October 1, 2017 by Italiano

[amused1]

17, best friend, woodpile in the back yard.

[+ Billsboy4]

I was 15, with my male cousin in his parents bedroom

[Becket]

Guess I'm one of those who does not have clear memories of the "first time." At some point, though it was an older cousin at a sleepover. I think they called it "buggering" back then. Recall I didn't like it much. Always been more interested in the back than in the front. (It confuses the hell out of the boys at Swinging Richards cause I usually ask them to turn around in a lap dance as I enjoy back, shoulders, ass, etc.) Fun thread. Thanks. Cranks up this old brain.

[Lookin]

Hell, I can't even remember the last time. http://www.boytoy.com/forums/public/style_emoticons/default/unsure.gif

[+ azdr0710]

Hell, I can't even remember the last time. http://www.boytoy.com/forums/public/style_emoticons/default/unsure.gif

 

 

looks like you forgot (!) to put in your usual visual......

 

 

[+ quoththeraven]

17, best friend, woodpile in the back yard.

You sure this wasn't a game of Clue?

[Jakeenct]

I was 12, seventh grade, private school, fellow classmate who I usually walked home with somehow we got into a conversation about sex. I cannot recall the content of the conversation that led up to our meeting that evening but we met after dark in a wide-open field adjacent to a major New York City airport (totally out of sight). I think it started out with the "show me your dick" exchange but also keep in mind I was not aware I possessed the power of "ejaculation" yet. So we dropped 'em, he took a leak, by then I was hard as a rock. He performed his 12-year-old version of oral (in all honesty you could have looked at my dick a that point and I would have shot all over). I shot three times by his hand and the discovery blew me away. This guy had a lot more on the ball sexually than I did as he began complimenting me on my dick. He never came and my feelings toward him after were not the greatest; I was really confused. Today when I think about that event, it's with absolute pleasure !

[+ José Soplanucas]

Hell, I can't even remember the last time. http://www.boytoy.com/forums/public/style_emoticons/default/unsure.gif

 

I have reached out to all my underground sources and this time I have surpassed even @BabyBoomer . I proudly present everyone to @Lookin 's first documented sex act. Which means that the actual first one may have taken place even earlier:

[Lookin]

I have reached out to all my underground sources and this time I have surpassed even @BabyBoomer . I proudly present everyone to @Lookin 's first documented sex act. Which means that the actual first one may have taken place even earlier:

 

Hold on, I'm getting a faint whiff of olive oil. http://www.boytoy.com/forums/public/style_emoticons/default/rolleyes.gif

[amused1]

Hahaha While I did have a thing for the Professor on Gilligan's Island, Professor Plum never did it for me. And, I have yet to try appliances so that limits weapons. I have done it in pretty much every room of every place I've lived though. Maybe Sex Clue is the next Shark Tank million$$ idea?

[Pepper Young]

Remember it like it was yesterday. I was 14, the other guy, older. Cheap motel by the freeway. Had a blast.

[Mydavid]

The first time I had sex is with my wife, I was 29 and after we got married.

The first time I had sex with a man, I was 36, I will remember it forever.

[+ poolboy48220]

First time was with a female friend, former co-worker, after I'd taken her to my new job's Christmas party. She was one of two women I've had sex with in my life. First time with a guy was a glory hole in a bookstore, he came in my mouth and I was freaked out about AIDS, I got tested the next week and made up a whole story about how it happened.

 

First real interactive time with a man was with an escort, I'd spent a month working up my nerves and perusing the ads. The guy was very sweet, knowing it was my first time.

[Bearofdistinction]

I find it interesting that some don't remember their first time.

 

I was 14-15 but easily passed for 18 - Cut Classes and went to small adult cinema with a sign out front that said "ALL MALE" there was a balcony with old couches - and an 18-20 yo all-American boy sailor and I think we played for several hours/days . . . ahhhhhhhhhhh

 

Long before AIDS he taught me about why using condoms for anal was important something he learned in his travel to exotic places asses and faces.

[liubit]

My first male kissing and sucking was with my best friend, when we were both 15-16. Boy, did I have a crush on him. Unfortunately, he, not so much. Although it was awkward, I enjoyed it enormously. However, he felt terribly guilty about it, and he quickly “dumped me” as best friend. Sad.

 

My first “real” sex was with a girl, when I was 17-18, and I didn’t really enjoy it. Fast forward to my late 20s. By that time I had come to terms with my being gay, and I had my first true male encounter when I fucked a cute boy I met at a bar in NY. I had a total blast. The rest is history.

[bostonman]

Through my adolescence, I had a few chances to do some simple fooling around stuff with a few neighborhood boys and also a school friend of mine named Tim. (I mentioned Tim in the recent thread about Hugh Hefner, as a copy of Playboy helped one of our sessions along lol.)

 

But - how many of you actually had your first orgasm as the result of fooling around with someone?

 

His name was Jay. He lived down the street. I had just turned 14 and still hadn't cum yet. He was year or two older, but also a bit behind in school. I won't go through the whole saga of how we first got into stuff, but I did get him to show me what it looked like when he shot cum, because I was so curious about it. We'd meet after school every now and then and sorta fool around - mostly j/o stuff, but then one day I asked him if he'd be into experimenting with sucking. I sucked him first for a while - not to completion though. Then he tried it on me.

 

I was laying back on the bed, enjoying his first attempts at giving a blow job. It felt really good. But I also felt really nervous - that kind of butterflies in my stomach nervous - I think partly because I was worried my dad might get home soon and we might get caught.

 

But then that feeling in my stomach seemed to intensify. And all of a sudden, without any warning, I started to pee in Jay's mouth. Except - you guessed it - it wasn't urine. I remember, like it was yesterday, the feeling of two big squirts going right into his mouth, and me feeling powerless to stop it from happening. It was then that he pulled away, and that we both realized the stuff still shooting out onto my torso wasn't piss - it was thick and white - I knew immediately what it actually was. It had finally happened. And it had taken my friend to get it to happen, to the point where he actually swallowed my very first sperm shots. (He was, as you imagine, rather shocked to have done that, but he seemed ok with it, even though he didn't do it again.)

 

But my stomach feeling was also right in terms of my instincts - as I was cleaning up that first load, I heard the car pull into the driveway - my dad was home. We got cleaned up and dressed in lightning speed. I think then we went for a bike ride, lol. Ah, youth...

 

But I will never ever forget that moment when I started to shoot...even though at first I didn't realize it was cum.

[+ azdr0710]

But - how many of you actually had your first orgasm as the result of fooling around with someone?

 

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!

[MikeBiDude]

Through my adolescence, I had a few chances to do some simple fooling around stuff with a few neighborhood boys and also a school friend of mine named Tim. (I mentioned Tim in the recent thread about Hugh Hefner, as a copy of Playboy helped one of our sessions along lol.)

 

But - how many of you actually had your first orgasm as the result of fooling around with someone?

 

His name was Jay. He lived down the street. I had just turned 14 and still hadn't cum yet. He was year or two older, but also a bit behind in school. I won't go through the whole saga of how we first got into stuff, but I did get him to show me what it looked like when he shot cum, because I was so curious about it. We'd meet after school every now and then and sorta fool around - mostly j/o stuff, but then one day I asked him if he'd be into experimenting with sucking. I sucked him first for a while - not to completion though. Then he tried it on me.

 

I was laying back on the bed, enjoying his first attempts at giving a blow job. It felt really good. But I also felt really nervous - that kind of butterflies in my stomach nervous - I think partly because I was worried my dad might get home soon and we might get caught.

 

But then that feeling in my stomach seemed to intensify. And all of a sudden, without any warning, I started to pee in Jay's mouth. Except - you guessed it - it wasn't urine. I remember, like it was yesterday, the feeling of two big squirts going right into his mouth, and me feeling powerless to stop it from happening. It was then that he pulled away, and that we both realized the stuff still shooting out onto my torso wasn't piss - it was thick and white - I knew immediately what it actually was. It had finally happened. And it had taken my friend to get it to happen, to the point where he actually swallowed my very first sperm shots. (He was, as you imagine, rather shocked to have done that, but he seemed ok with it, even though he didn't do it again.)

 

But my stomach feeling was also right in terms of my instincts - as I was cleaning up that first load, I heard the car pull into the driveway - my dad was home. We got cleaned up and dressed in lightning speed. I think then we went for a bike ride, lol. Ah, youth...

 

But I will never ever forget that moment when I started to shoot...even though at first I didn't realize it was cum.

Haha first time I came I thought I was pissing in my sleeping bag as a Boy Scout friend next to me in his sleeping bag was showing me how to stroke! Even though I thought I was “peeing” I was conscious that I really didn’t want to stop moving my Hand!

 

I was 11 or 12? Never had a wet dream that I can remember, I chalk that up to early masturbation?

[+ Hoover42]

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.

[bostonman]

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

 

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

 

I knew a set of triplet boys in high school - very cute, and assumedly all straight, but I do remember fantasizing about wanting to blow them. And also if they ever at least played comparison games with each other, lol.