Knowing everything you know now...

[Japbtm]

I have a great routine now to clean myself out before bottoming. Wish I knew how to do it better before, I would have had way more sex! 

[PendragonSpirit]

I don't think I'd have changed the when, necessarily, but I would have adjusted some of the details. My stepdad was the first person to "officially" introduce me to porn (of course, I - being a horny teenager with access to the internet and a computer in my room - had already seen plenty of it..), bringing home magazines for me with full-on fucking and sucking (as opposed to just "naughty photos" of women ala Playboy) and renting videos for us to watch together whenever we had the house to ourselves for a night. Looking back, I'm pretty sure he was putting feelers out to see how far we'd take things, though we never did more than j/o together and comment on each other's dick sizes. So I'd have definitely pushed those limits to see just what trouble we could get into together.

[leatherpunk16]

I think I would have practiced more solo stuff. I was isolated a lot in my youth and 20s, and never did more than jerk off except on rare occasions. It never occurred to me to drink my own piss. Or smear my own spunk on my face. Or put vegetables in my butt. Or even finger myself. I just didn't do those things, and certainly didn't think of trying them. The outlet for discovery just wasn't there, and I had no confidence, so it didn't happen. When I finally got to explore my sexuality in my 30s, I realized I had missed out on SO MUCH. 

If I had come out at 20 instead of 29, I might have got laid way more in college, and actually built some decent memories of the years. I think that's what I regret the most. Missed opportunity that I never knew was there.

[Guest]

When I was 16 and in high school, had a classmate that was gay and on several occaisions he tried to put the moves on me and a few other guys, but it wasn't the thing to be caught doing in our small community, as nothing was a secret for very long there.  It was about that time I found out what girls were all about also, so it was about the furthest thing in my mind becoming involved in a gay affair.  It wasn't until I was in between 24 and 25 yrs old and after my first marriage failed that I had my first gay/bi experience and became increasingly curious.  The very first experience wasn't a good one for me, so it was a few months before the right guy came along and talked me into giving it a try again. That was a bit of a turning point in my life, but still it didn't quit change my mind completely about it, but at the same time, I couldn't shed the curiousity of it. For the next 26 yrs or so I played off and on at the bookstores and a few times at the baths when the mood would strike. It was finally when I was 51 and separated from the second wife things began to fall into place and I really began to come to terms with the feelings, desires, and the person I really was and needed to be.  As they say, "it is all history after that".  Knowing now, what I do, I really wished I'd taken that first chance when I was 16, I think my life would have been a lot better and a lot less troublesome if I had.   

[hntnhole]

Wow ... obviously at that tender age, it was probably unfair of that man to offer his Cock, but - he must have recognized some certain something in you, and couldn't resist.  I've often wondered if young gay kids who aren't even aware of their sexuality yet, give off some kind of signals - unknowingly - who they will grow up to be.  I can't say I agree with what the man did, but in your case, it seems he not only did you a favor, but the rest of us as well.  Maybe I was so oblivious when I was a kid, I didn't recognize subtle cues?  I don't know - maybe I was just too much into kid stuff to recognize?  In any case, I'm happy for you that you found yourself earlier than later !!!

[YourNoLimitsBottom]

Currently 40s, started very late 30s. Wish I had been bolder and started earlier, early 20s or sooner. I ESPECIALLY wish I had had the guts to join the gay couple in college who invited me to have sex with them.

But as others have pointed out, who knows how things would have turned out if things had been done differently. I am probably better off having gone the way I did. I'm definitely making the best of everything I can going forward.

[evilqueerpig]

I knew I was QUEER at 5 years old, even though I didn't know the proper term for it.  At the age of 17, on a summer morning, I knew it was time to find my first man, so I went to the local QUEER/nude beach and when the image of my masturbatory fantasies emerged from the water, I knew I'd found him.  Staring daggers at him worked and when I admitted to being a virgin, he agreed to be my first.  He was gentle and patient, aside from being sexy and sweet and it was an amazingly wonderful experience that turned into a 3 month fling.  Nothing could be better than having a perfect first time.

[got2getit]

On 1/24/2022 at 2:29 PM, pansexualperv said:

I had my first gay sex at 34 and I wish I had taken the plunge a lot earlier. Teens or early twenties would have been ideal 

It was a pleasure to have help you take the plunge all those years back. Loved popping your cherry. Just would have had me chatting you up to take that sweet ass with you in your twenties lol.

As for myself wishing i had taken up some of the more kinky offers i got early on in my hook ups in my youth. Would have now been scoring a like higher on the Gay Sex Bucket List than my 156.

[Pigforcum]

46 minutes ago, got2getit said:

It was a pleasure to have help you take the plunge all those years back. Loved popping your cherry. Just would have had me chatting you up to take that sweet ass with you in your twenties lol.

As for myself wishing i had taken up some of the more kinky offers i got early on in my hook ups in my youth. Would have now been scoring a like higher on the Gay Sex Bucket List than my 156.

Thank you. I always look bad fondly on the fucking you gave me. Started me fucking BB and never used a condom since

[Davidc]

Wanked with a guy under 10 , got fucked by a guy at 13 , tagteamed  a girl with her older BF at 14 or 15 

[mancunthole]

Being close to 60 now, I wish I had understood myself better. I knew in my late teens I liked men. But that was somehow "wrong". After years of playing with toys and not finding satisfaction with women did I wandered into a book store.

It was not until my late 30's that I let a guy fuck my ass-pussy in an adult book store video booth.

It was dirty. I liked it. Dude fucked the hell out of me in that booth. Cum and shit oozing out of my pussy.

While I lived near the book store I regularly went to the theaters in the rear to get laid.

Been slim pickings in the last couple years since I moved away.

[poztwinksrhot]

On 1/23/2022 at 12:54 PM, profwhtforhung said:

Knowing everything you know now, how old are you and when do you wish you had had your first sex?  

Mid-50s, and it depends on how you define sex.

For the first general sexual experience, my first was a very brief 'you show me yours' experience when I was 9yo, with a boy a few years older than I. I wish that he had known more and taken it further, and that he had lived closer so that we could have made it a regular thing, because I really wanted to after that first time.

For the first true 'gay sex', the first time I had a cock in my mouth was because of losing a game with a classmate when I was around 13.  It was only for a few moments and I didn't even put my tongue on it because I wanted him to think that I was straight and resisting.  If I could re-live that night, I'd clamp down on it and make sure that he knew I wanted it badly, as well as what came out of it.  Reality was, I wouldn't be brave enough to do that until I was twice that age.

I envy and commend those who were brave and took action on their own early in their lives.

[Searchingforit]

Knowing what i know now i wish i had given in fully to my desires as a youth and into adulthood. I had my first gay sex at 12 and i suspect the person could see through my facade and knew my secret desires.

Trouble was it was the early 70's, homosexuality was illegal and the peer pressure was such that one did not do 'those' things. So i ended up getting married having kids and it is only in the last 15 years i have embraced my need for m2m sex.

In truth i should have come out and followed the gay lifestyle that is my true nature!

[theplayerking]

I wish the culture had been different when I was growing up in the 80s and early 90s. Younger guys are much more open to experimentation now. I didn’t hookup with anyone in high school and only one person in college because I was not attracted to the gay guys my age that I knew. With apps, PrEP, access to porn and the general change in culture, Gen Z is having much more fun. 

[Pigforcum]

On 1/24/2022 at 2:31 PM, WestPhillyGuy said:

I waited until I was in my 40s...and like you wish I had taken the plunge earlier.

Yeah it's one of my only regrets is not taking cock earlier in life. I knew I wanted to since I was a teen but never had the courage to