Tell us about your first time with a guy

His name was Palo. We were both in the Legislative Youth Program. He was a few years older than I: very cute, dark curly hair, dreamy eyes.

An overnight train from Paris to Rome. He got off at Pisa, after getting off twice before then. Paolo. A dancer.

I was left alone in the cabin/couchette between Pisa and Rome and remember the freedom, the liberty, the promise I felt as I stared at the sunny skies and expansive sea. I opened the window and the cabin filled with the sounds of the train and the light Italian breeze.

A very special moment, to be sure. His kisses were freedom.

Our tryst was too spontaneous for anal and I didn’t kniw what to do so I did what he said. I humped the cleft of his butt with suntan oil and blasted all over his back!

[quote] I humped the cleft of his butt with suntan oil and blasted all over his back!

Link?

Surprise anal.

R2 wins the thread.

R3 nice description

He was a beefy (not fat...muscular but not ripped...like a linebacker) guy with dark, curly hair and a mustache...beautiful dark eyes. Lots of kissing with our hands exploring each other's bodies. I remember getting naked and my hands on his butt (I am really into men's butts). I remember groping his butt as we kissed and sliding my fingers down his crevice. I can still feel the thrill of doing that. We jerked each other off. I came quickly, and then he did. And then I got scared...what the fuck did I just do? It was a mix of emotions. I was out of college...mid 20s..23 or 24. He held me tight. I think I cried.

1983. I never knew his name. I was 17, and he said he was 16. Met in a library after he observed me furtively reading books on homosexuality. We went into a men’s room stall and I sucked him off until he exploded in my mouth. I swallowed. Ahhh young romance.

I was newly 21 and decided to go to a local bathhouse. The first time I went, I was shocked by the number of men who were having sex right in the open. I was too shy to participate, but my dick was fully hard the whole night. A few days later, I went back. This time I was sitting naked in the steam room, which was really a cave, carved out of the ground and lined with stone. I was sitting there until a random guy walked over and put his hand on my dick; it responded. I reached out and took a hold of his. He asked if I wanted to go to his room, which I did. That night I discovered the joys of oral sex ( giving and receiving), kissing uninhibitedly, and getting finger fucked. That began my life of debauchery.

It's a long story, and I don't want to be judged or analyzed, so I won't go into details. Let's say it was a fun and enlightening summer.

Not all of us would judge or analyze, R11.

I did it all

I met him at the candy store! He turned around and smiled at me. You get the picture?

[quote] I was newly 21 and decided to go to a local bathhouse. The first time I went, I was shocked by the number of men who were having sex right in the open.

But, it's wrong! [italic]Shockingly[/italic] wrong!

Yes, we see.

Tent sex.

my first time was awkward and while he was tender, I wish it'd played out far differently.

I consider my 'first time' to be years later when I knew more of what I was doing and the guy was way more compassionate, giving.

With the same-aged neighbor's boy, starting out with mutual jerking off when we much too young, frankly. (Still children, in fact.) We met up occasionally to jerk off and blow each other during our teens, even fucked once later when we were around 17-ish. I think we stopped seeing each other around my 19th birthday.

[quote] Tent sex.

Was the tent a top or a bottom?

There was no anal, so I guess it was a “side”.

I was 16 but lied and told him I was 18 when we chatted on Adam4Adam or maybe it was Manhunt. Told this story before on here.

Parents were out of town. He came over and I blew him. I don't even think I came. I remember how excited I was when he arrived and the smell of the Irish Spring soap on his body. After I did the deed, i told him I was actually 16 and he booked it out of there. I begged him to meet up again but he said no. Until one night he invited me to his campus apartment, about 3 months after I blew him. The place was a mess and a garden unit so damp and dark. He let me blow him but wanted to fuck me. That wasn't on my radar at all. I let him try but it hurt too much and I he wasn't patient. He claimed he had to meet up with friends so asked me to leave.

After that I used Craigslist , Adam4Adam, and Manhunt to get more men. Unbeknownst to my parents, I would sneak out and drive to dark lit farms or random guy's houses, or even an hour away in Indianapolis (when my parents were away) for hookups. I always topped and used a condom. But, I craved the attention and didn't think beyond my cock.

Sadly, I don't even remember my first fuck topping or bottoming. I kept a mental list met up with like 16 men before turning 18, they didn't care or loved the idea of fucking with a teenager. My luck, I met a boy my age a month before I was off to college. I wish he could have been my first and only because having a healthy relationship, though short, was magical. I don't regret most of the other hookups, except for that Marine that gave me my first STD. Was fun explaining that away to my parents as I went to the ER when the puss turned to bloody discharge. Beyond that, I was lucky to make it out alive from all those encounters in strange men's homes.

Working on a history project at his house, we were both 14. We blew each other after the poster board was completed.

My father used to work an afternoon shift and most nights when I was between the ages of 12 - 15, he would come to my room and fuck me when he got home from work. I was always face down and pretended to be asleep. Then he’d shower and tell my mother he didn’t shower at the plant because he rushed home to be with her. I left at 16 as soon as I could get out of there and started charging people to do what my father had done to me for free all those years.

He kept bragging about how big he was and when we whipped ours out, we were the same size. I think he was bummed he didn’t win that competition.

I can’t tell if R24 enjoyed it or not.

I was just shy of 14 and a few of the older guys in my neighborhood were on a kick of making prank calls to local businesses, often joking about sex or offering a BJ just to see what they'd say.

We called an auto body shop and I knew (sorta vaguely) who the owner was - handsome Italian guy with some gray at the temples. He had a short, beefy (but solid) body and a face kinda like Chris Meloni. Would not have been out of place on the Sopranos. He answered and when we asked he told us "yeah, well you come and get it if you want." Probably joking.

But somehow, I had the nerve (not something I often had) to call back a day or so later and basically said, my friends called you as a joke the other day but I'd be serious. I remember him saying, "Really?......well, fuck yeah." I didn't have a car so he met me at a park and drove me to his shop about half a mile away. It was intoxicating - the smell of gas and oil, and then just getting to unzip his overalls and see his hairy body. His dick was fine, not the biggest or shortest I ever had, but probably perfect for my first time. I managed to make him cum twice while I was there. He was amazed when I told him it was my first time.

I can't believe I did that at that age. I really can't believe some of what I did before I moved out and went to college. But it was a different time. Even with it being the 80s, I just never had a sense anyone was going to hurt me. It all felt like a very secret club and as a new member a few of the older members took their time to show me around!

That's nifty, r27.

R28 is fat and ugly and unfuckable and can’t imagine that attractive people ever have sex

It may sound "nifty" but it happened.

I was kinda spoiled living where I did when I had my first bunch of experiences, too. Lots of second generation immigrants - Italians, Eastern Europeans, guys who were very macho and/or had big endowments. I thought that was available everywhere but it kinda ended up being very specific to the rust belt region where I grew up.

R30 did you score anymore primo rust belt cock?

I met him at the candy store.

Verificatia of sizemeat?

R32 A literal candy store?

R34 Yes. He turned around and looked at me.

Black guy from the health club with 4% bodyfat. Chest was 1.5x time the size of waist, omg. Big legs, too.

R12 No. We WILL judge.

Met a guy on one of those phone chat lines in the late 90s and went to his house.

He suggested we hop in the shower, and I figured that’s what gay guys must do.

Got naked, got in the shower, he touched my shoulder, and I shot buckets of cum on his leg.

Wow, r38, you must've been tender to the touch.

R38 was it done for you after you shot? Or did you rally for round 2?

The Yankees were burning Alanta.

R40 - I freaked out and lied and said I needed to leave to see my girlfriend.

He was kind enough not to laugh openly at me.

I’ve never come that easily again. But it sure confirmed I was gay.

The summer I turned 13. It was hot and humid and I was reading on the front porch; I was the only one at home. A couple guys who were going to be seniors rode their bikes past a few times, then stopped to ask if they could swim in our pool. My dad used to let the football players jump in after practice (we lived across the street from school), but he said before he left that I couldn’t have anybody over to swim since no adults were home. I told the guys that my dad had said no. After a few “C’mon, man”s, I acquiesced . I went into the house to get the key to the gate. They said they just wanted to cool off and they were true to their word. After ten minutes, they got out of the pool.

They had stripped to their underwear to go in, and after, one put on his shorts and t-shirt. The other asked if I had a towel he could use. The other guy got on his bike and left, and one followed me into the basement. I handed him a towel and he asked if he could shower off the chlorine in the shower right there. I said okay, and he took off his underwear and washed off. I tried not to stare, but I guess I too obvious. I popped a boner as did he. He turned off the water and said it would be nice if there was a girl there who could blow us. I don’t recall what I said, but he lifted his dick in his hand and said, you could do it. He stepped over to where I was standing, pushed my shoulders down and I sat in a chair, he stood in front of me, put his hand under my chin, and guided his dick into my mouth. Like a fish to water, I started bobbing my head up and down. He pulled out momentarily and I thought he had cum, but he was just leaking a ton.

He was surprisingly gentle, in retrospect. He slid his dick in and out then announced he was going to cum and did I want him to shoot in my mouth. Before I could answer, his load flooded my mouth. I think I swallowed all of it. He handed me the towel he used to wipe my mouth. Then he dressed and told me not to tell anybody what we just did. Then he left.

It was at Harvard.

I was an uptight , deluded Catholic boy. Waited until I thought I had found someone who would love me forever. After four months of dates, we finally had sex. It was a letdown. Scared me off sex for a few years. That first sexual partner / dear guy committed suicide fifteen years ago.

When I lived with my dad. My stepmother’s cousin’s adopted son. I was 12 or 13. He was 14 or 15. I spent the night at his house and we were lying on the bed in the dark watching movies. I felt his dick on my ass and thought “here we go…” we used Vaseline for lube and he had a huge thick 9 inch curved cock. It hurt so bad I almost passed out. After that we fucked regularly for a few years, until I moved back with my mom.

Kinda sad, R43. Bittersweet.

Wow, I wish my 1st was like R43 ‘s

After a frat party, first week my freshman year. One of the brothers asked if I'd rather sleep over at the house instead of walking back to my dorm. Of course I would. I woke up in the middle of the night, feeling his mouth moving up and down on my cock, which I then proceeded to do to him. God, it was so delicious to have a rock-solid cock in my mouth.

Finally, I was sucking cock. The year before, I'd dreamed of doing it with these two guys named Bobby whose lockers I was in between in my HS pool locker room. It was a dream come true, and he was sucking my cock too.

How were you at a fraternity party the first week of freshman year, R49? Fraternities don't usually invite freshmen unless it's rush week and that isn't the first week of classes.

It was the early '70s, r50. Frats were quite unpopular at that point in time.

R43

So for all of you who posted here, do you feel the first guy, or first few guys you were with, sort of "imprinted" a particular type that you liked? Or was it the opposite - not a great experience and you looked for the opposite for future hookups?

I kinda think my preferences in men were really shaped by the first few years of hookups that I had.

R53, I have always favored white guys with medium brown to dark brown/black hair, and the first guy I had sex with fit that description. Every guy I'd been attracted to before that was of similar coloration. Jewish and Italian guys go to the front of the line every time. Irish and English sometimes, too. This has remained my type, and it's also what I look like (dark brown haired, mostly Irish Euromutt).

I'm not sure if my first time was the show me yours I'll show you mine in 5th grade, Or the stumbling attempts at blow jobs in 6th grade, Or the straight experimenters in college.

Or the first gay guy I had sex with at 27 years of age.

A conundrum. What say you all?

Good stories!

R55 probably not the show u mine, but maybe the bjs

We met in clown school, had sex with the noses on- he showed me how to get all the greasepaint off my cock afterwards.

I had a friend who I messed around with starting around 14 until we were 18 and went off to different colleges. Mostly just jerking each other but eventually progressed to mutual oral. Never any kissing or tenderness. I always felt guilty about it. Stayed in the closet all through college. Looking back, I missed out on a lot of hot cock action from guys who made passes at me. At the time, I was oblivious.

Finally came out when I was 26 and was fixed up with a guy who was 7 years older than me. I consider him my true first time. He was great for a first time lover. Taller than me, dark hair and eyes. After a few dates, we spent a weekend together, naked most of the time, kissing, sucking, rimming, fingering, and fucking. He said I was a fast learner! We were together for a while. My first real love, but we had some differences that weren’t going to work for us long term. Even after we broke up and started seeing other people, if we ran into each other, the chemistry was just too strong. I blew him in the bathroom at a party. He rimmed and sucked me off in a closet at his work! He eventually moved away. I haven’t seen him in 20 years. Right before he moved (to be with a guy he met online), I went over and we got together one last time.

I’ve been with a LOT of guys since, and I’m married now to a great man, but I do still think about that first love. And all the hot sex we had!

Was a late bloomer - think I was 24. Pretty sure I met him on AOL. He was traveling in my area for work. He was older, maybe 35-40? I just wanted to get it over with. I met him in the coffee shop of his hotel. He took me up to his room. He kissed me with bad coffee breath. He arranged us in a 69, with him on top. I was petrified. He came in my mouth and I openly dry heaved. I can't even remember if I came. I got dressed and bolted.

Late bloomer here, too. First time was when I was 22 or 23 back in the early 1990s. I worked in computers and lived in Santa Cruz, and read about bulletin board systems for gay dudes, so I got a modem and checked it out. Talked to a nice sounding guy and decided to go up to see him in SF. We got along really well, and he knew I was a complete newbie, so we really just hung out and he was a complete gentleman. Hung out so long that I ended up staying over, and I ended up molesting him the next morning. We really only did hand stuff and kissing that time. He came down to Santa Cruz the next weekend and that's when I got introduced to everything - oral, anal, frottage, etc. He was a perfect person for my first time.

I knew I was gay from an early age but being in a Conservative, Catholic family I innately knew it wasn’t something I wanted to pursue until I went away to college. Call it survival instinct.

I knew my best friend was gay but we never really talked about it but we went to the movies all the time and listened to the same music and were both in choir and drama club. All the trappings were there.

In our senior year of high school he started going to gay bars downtown (major urban area) with a senior who was pretty much out (this was 1983) and eventually I went with him a few times. Of course we were under age but somehow got in, a few old men would buy us drinks - Amaretto Sours. My friend loved the attention but me, not so much. I would go sit in the car and wait to leave. It wasn’t my scene at all. I was 16 years-old. My friend started dating this guy who was probably twice our age and they had sex together. It was totally illegal. I guess it was paedophilia, technically, but my friend though under age was not a child. He was very willing and knew exactly what he was doing. But it definitely seemed sleazy.

Anyway, the summer after we graduated, my friend was all sad and we made out one night. Another night he gave me my first blow job, from a guy. (I lost my virginity to a 16 year-old girl when I was 12 and she gave me a blow job as well.) My friend was very controlling- probably like the guy he’d been with - and didn’t want me to move while he was doing it, etc. I remember thinking it was all right, I didn’t mind that it happened but I didn’t want to be with him really and I was counting down the weeks before I left to go to school out of state. He tried but I didn’t keep in touch with him. Couldn’t wait to be rid of him.

I'd share, but my story is so unseemly that even jaded DLers would be shocked.

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