Men, What was Your First Time Like? Did you Enjoy it or Regret it?

In hindsight it was perfect. With my girlfriend, who was a virgin, and it hurt her. I stopped. It took us a few tries until she was comfortable. But we went through it together. I learned early on that sex is a team sport.

Best 30 seconds of my life

My first time was with my first wife on our wedding night. It was very enjoyable, but not earth shattering.

first time I tried to rub her pussy with my fingers like I watched in the porn (make her squirit). well obviously it was painful and not enjoyable for her. luckily for her we didn't have the chance to actually make sex because her parents came back home. so i left still as a virgin
my other first time was with another girl and after a brief warm up the time for penetration came. here I have to mention the for some weird reason my biggest scare as a virgin was how I will slide my dick inside her pussy. something made me believe that this is the hardest and trickiest thing in sex lol. so when I grab my dick and place it just at the entrance of her vagina it instantly went soft. I ran to the bathroom trying to resurrect it but all was lost.
my real first time was with another girl. this time I got smarter and decided to sit and let the girl slide it in her pussy. lol and she did it and she started to ride me like crazy and after like 10second I came. I tried to stop her but it was too late lol
I had this fear about penetration with the next couple of girls...

Assuming first full intercourse, it was intensely awkward and cramp-inducing due to poor positioning but enjoyable regardless. It was the first time for the both of us. Second time went much, much smoother and was far more enjoyable.

I wouldn't say I regret it... but not sure it was worth the $150 either. We never even got to use the jar of peanut butter.

I didn't enjoy my first time. I wasn't sure what I was doing and came too quickly.

She wasn't very tight at all and it was awkward and sweaty.. She was rather chubby so it was hard to spread her, find the hole and get it in.. Overall it was pretty disappointing, although it took about 25 minutes of thrusting I did manage to cum and so did she a few times.. She enjoyed it more than I did

I kinda did regret not waiting, but shit happens I guess

It was the best 30 seconds of my life. ᶘ ͡°ᴥ͡ °ᶅ/

I feel very lucky. My first time was with a more experienced girl who was WAY out of my league looks wise. She was totally cool with everything and even told she was impressed with how long I lasted for it being my first time. I am sure she was lying, but hey :) it was nice.

It was fun and lasted a long time - like 4 hours. She was older than I, and on the pill. Def not a virgin, though we never dated or anything again. She had a boyfriend turned out. We've bumped into each other over the years and get along fine - but I doubt she has any clue she was my first.

It was very intense and out of control. We completely lost our heads and just went for it. That was the good part. It was also rather awkward because both of us were inexperienced. I came, she didn't. She said something like "that's it?" She and I had a laugh about it later after much more practice.

it was, meh...she was a virgin, and I didn't want to hurt her, used a lot of lube, but that didn't help..can't enjoy it knowing your partner is in pain, so I stopped...

Lol, like others have said, it was over before it started. I remember seeing the surprise/dismay in her eyes at how quickly it went.

I was hideously nervous, but I loved it even though I found it nearly impossible to reach orgasm.

Disappointed, all the hype, wasn't as I thought it would be, but; became much better over the years

14,, and i was ecstatic
i dont think guys in that age are capable of regret of sex

Was quick. Awkward. Made her get on top; maybe a mistake

It was enjoyable. Not the greatest thing ever. But it was alright.

I am going to say it was good.. I enjoyed it very much

Was ok, wasn't amazing

It's not happened yet 😃

I enjoyed it very much

Loved it!