My [Almost] First Time (Warning: Long, but good.)

Recently, I made the decision to try and meet guys to fuck. I had always imagined my first time would be special. That it would be something memorable, and not just a suck-fuck-and-leave type thing.

Being on this site for a few months has helped push me towards being ready to finally do it; what an asset. I've read up on a ton of various threads in these forums, ranging everywhere from safe sex, to relationships, to checking out different profiles and guys in the show off forum. I've also developed some great online relationships with people in the chat room, since I am a regular there now.

I would get people telling me or asking me "you must always have someone in your bed" or "how many guys have you fucked?" And my answer would always be "I'm a virgin." You can imagine I got sick of saying that pretty quickly.

I felt mentally ready to start my sex life, I just couldn't find guys who I wanted to fuck. That's been a problem for me. Being a college aged guy, and attracted to men more than double my age. I've always been physically drawn to much older men, and that's been a big source of insecurity for me. Call it weird, call me a freak, whatever. That's the way it's always been for me and it's been a struggle trying to embrace my attractions.

But now I was finally ready. I joined an older-younger dating site about a month ago, and started messaging random guys who turned me on or looked interesting. I was very cautious, making sure I communicated with the guys a ton before even considering a face-to face meetup.

Last week, I was chatting with phoenix1, a friend of mine here and fellow chat regular, and was feeling very down after a prospective hookup fell though. I just said "fuck it, I'm gonna meet someone else to fuck."

Anyway, I messaged a guy I found very cute on Saturday night asking if he wanted to hook up. He replied affirmative and we decided to meet that Sunday afternoon by Bryant Park in Manhattan.

E, let's call him, was 100% Puerto Rican, although I thought he was white from his profile. Fifty years old, he stood 5'9" with a cute-and-handsome at-the-same-time face, had a goatee and salt and pepper hair along with a good beefy body. Right away, he emanated a great and friendly vibe - like a human being and not an internet sex drone. Major points right there (and take note, all you fucking weird drones lurking on here). "This isn't what an anonymous hookup is supposed to feel like," I thought.

We walked around Bryant Park for a little, looking for somewhere to sit or maybe grab a cup of coffee, until after a few minutes he invited me to his office, which was a few blocks away. It was empty, and we smoked a joint. After some more small friendly chit-chat and getting to know each other conversation, he put his hand on my thigh. I cornily and tongue-in-cheekly said "so what do we do next?"

Both of us stood up, and we started kissing. The mood changed and we got into it - hard. Pun very much intended.

One note: kissing for me is electric. I enjoy kissing as much, or more than, any sexual act. The feeling of tongues interlocking, noses breathing warm air on each other's faces, hands running through hair takes me to another level. It also takes my erection to another level.

We took off our clothes after a few minutes. He said my body was perfect and immediately started kissing my slim, furry chest and abdomen. I unzipped my pants and pulled out my hard, uncut cock. Both of us were completely naked, and he took a step back to admire me in all my nude glory.

Being inexperienced, you'd think some of this might feel awkward and unknown to me. But not once did I feel that. E was very selfless and passionate, putting me first and making sure I was pleased. I took little cues from him and pleased him as well.

We took turns sucking and massaging each other all over, kissing in between it all. It all felt right. Eventually, we blew up an air mattress (how convenient, having a blowup mattress in an office), threw some sheets on, and went at it more there. We smoked another joint, did some poppers, and continued.

I had my virgin ass played with, fingered, and eaten for the first time. E knew what he was doing down there. We 69'd, I fingered him, we kissed some more, and did everything but actually fuck.

We went at it from 3 in the afternoon until 7 in the evening, with several breaks in between. But you know what my favorite thing was? Cuddling with him. We took turns being "the spoon" and then we made out some more (noticing a theme here?), face-to-face, lying down. I peeked open my eyes every now and again to look at him as we were kissing. Pure bliss. The feeling was mutual with me.

It was special because he cared. It was special because he was a great guy, cute, funny, loving and all. I genuinely felt an emotional and physical bond with him, even after only a few hours together. He felt the same with me.

After we did our thing, we went to go get pizza, then see Men in Black III. The movie sucked, but we held hands throughout, kissing occasionally, but mostly just caressing each other's arms and legs.

*How about that, a date in reverse: screwing around and THEN dinner and a movie.

It was 10 o'clock on Sunday night and I had to get home. We said our goodbyes, had one final kiss on 41st street right off of 6th avenue, and then went on our way. Both of us decided we wanted to do it again. Fucking duh.

And how fitting, all of this falling on Puerto Rican Day in New York. I had myself quite a Puerto Rican Day.
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Comments

Wow, Stringer. That is just awesome and as I said to you on chat has actually brought tears of happiness to my eyes. I am so glad for you that you were able to go through this experience with someone who could treat you with respect, gentleness and in a caring way.

OK, so I am also a little jealous of him - but he seems to have been the right kind of guy to take you that first step in exploring your sexuality. So what if you guys didn't go all the way - there is plenty of time to experience that. Just learn from each experience as they happen!

Anyway, I am really glad for you - and it is good to see you smiling so much!
 
I'm insanely jealous of that lucky lucky guy who got to fool around with you :p

As i told you, sounds like you had an amazing time! Glad you enjoyed it my friend :)
 
Hey bud, I'm really glad that you were able to find someone to give you a good time!

Personally, I wouldn't have considered you a virgin in the first place, to be honest. There is so much more to sex than penetration! But if that's really what it takes to take your virginity, then so be it - but you shouldn't deny that you have some sexual experience under your belt... Especially after this meetup. ;)

I'm still happy for you, though. I hope that things follow through with this guy.
 
String-face,
I'm so glad you had an awesome experience like that.
It's great to be able to explore safely and happily.
Heart you.
 
I am really glad you found such a nice guy ! It is great your first time was with someone like him who takes good care of you. You seem to be a lovely person :) I wish your next times with him to be as good, if not better.

*thinks of how his first time will be*
 

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