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Okay, now you guys can shoot me some advice (long read…again)

Ambition92

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Hello all! In my previous post I simply introduced myself and my current situation regarding my sexuality. I didn't want to be one of those people that posts a thread every week, and this will only be my second, but I'd really like to get some perspective on my "new" situation. This of course seemed like the best place to get that perspective.

I frequent various gay dating/hookup sites (A4A, Manhunt, etc…) much to my dissatisfaction seeing as I've never in fact been with or "hooked up" with a guy. With that said, I have met some really cool people in the last couple of years but never actually met up in person with them (mainly due to where we're located and being to far away from each other). Anyhow, this brings me to last night. I looked at a few profiles on one of these sites and one in particular caught my eye. The profile was vague but based on his stats he seemed to fit with what I was looking for in a guy. I didn't expect much, but low and behold I got a message back!

The conversation was pretty basic for an hour or so before I asked if he had Skype, to which he did. Once we got on Skype we continued to chat via text and even exchanged face photos of each other. We both liked what we saw and continued chatting, which is when I found out that he's only here until after New Years because he's house sitting for a friend. It struck me as odd that he'd be away from his family over the holidays, but it turns out he's actually from out of the country and studying in a different part of Canada. I voiced my sadness because it seemed like we were hitting it off and then he suggested that we meet up in the next week. I was thinking the same thing so I suggested we meet up this coming Friday. We plan on meeting at a mall that he is close to.

Now, as I've already stated I'm so new to this. I've never met up with a guy before and for all I know it could just be hanging out and that's where it end. The thing is, this guy is gorgeous. Shortly after we made plans I asked if we could video chat. We did and he was even more handsome than his picture let on! He is exactly my type. I'm not particularly a "hottie". I've been told I look handsome and am charming, but only from middle aged women I work with and a few girls I fooled around with before. I'm also kind of chubby. I even told him that in case he wanted to back out and he said he didn't mind because he's not perfect either.

I just keep thinking "Why the hell is he interested in me?". If you read my previous post, you could probably tell that I'm a bit over-analytical and I tend to jump to conclusions instead of seeing how things unfold. In the back of my mind I keep thinking this won't happen and if it does, maybe he's not what he seems. I just really don't know what to think anymore. Which is why I'm here. What do all of you think about this? If it works out and we meet, should I treat is as a date?

If I didn't clarify anything, just ask and I'll try my best to explain. Thanks for reading guys, hopefully I don't come across as cray in this post.
 
don't think. ;)

you met on a hookup site and he's already told you he's only around for another couple weeks, so don't go into the encounter expecting to meet the love of your life or anything (I mean, it could happen, but statistics probably aren't on your side). be yourself, relax as much as you can, and treat it like hanging out with any other friend.

if you guys end up having great chemistry and it escalates from hanging out to "hanging out," just trust your gut and go with it if you're feeling like it. (and if you're not feeling like it, get out of the situation)
 
He likes you. Why are you complaining? :lol:

Although my first preference is for someone that's fit and not chubby, I find it funny that the guys I've been dating lately in the past, and now are a bit chubby, but fucking gorgeous in my opinion *|* Maybe he's in the same boat as I am. I can overlook the not so perfect body as long as I like how he looks and how we connnect ;)

Go for it man with no expectations and just enjoy being with him. Watching a movie with him might be a good idea so if you two ever feel frisky you can feel him up the leg with some reasonable privacy. (Find a non-popular movie so the theater doesn't have a lot of movie goers :lol:)

Good luck! And tell us how it went.
 
Haha, thanks for the advice guys. And yeah, I'm trying not to over think things. At best we'll meet up and just hang out…maybe something happens, maybe it doesn't, but I have to at least go for it. Worst case scenario is he flakes on me and I finish my Christmas shopping.
 
Just relax as best you can and enjoy yourself. Since this is all new treat it as a learning experience.
 
Hope it's a fun time for you.
 
Meet him. See what happens. Make sure you have a friend who knows who you're meeting up with and where you're meeting them. And buy condoms... just in case.
 
In a pleasant update I can say I had a VERY fun time today. He was a really cool guy all around, and it's a real shame that this will probably be the only time we're going to see each other, but you never know I suppose. Overall, today was a day full of firsts for me and it was thoroughly enjoyable.
 
In a pleasant update I can say I had a VERY fun time today. He was a really cool guy all around, and it's a real shame that this will probably be the only time we're going to see each other, but you never know I suppose. Overall, today was a day full of firsts for me and it was thoroughly enjoyable.

^You know that we want more details than this... :-)
 
On a little side note, I think it was the combination of eating beforehand and nervousness but I literally felt like I was going to throw up on my way to his place. I powered through it though and kept everything down :-)

Once we got to his place we cracked open a couple of beers, sat down (on two separate couches) and talked for a little bit. It wasn't really good small talk at this point, I just kept pointing things out in the place he was staying and using my sense of humour to lighten the mood. Eventually I went to the bathroom and had a small "pep talk". I sat down again for a minute before moving over to the one he was sitting on. I made a joke about it being "not so subtle"…What can I say, I hide behind my humour. Anyways, I finally ask "What should we do?" And we tease each other a little about who should make the first move. Eventually I go in for one and we have a nice little make-out session on the couch.

This quickly brought us to the bedroom where we made out a little bit more. I then unbuttoned his pants and went down on him. I came back up and kissed him again (this happened a lot!). He eventually started sucking me, which felt amazing. Then I asked him to turn over and I started rimming him. I've always wanted to rim somebody so this was a lot of fun. After rimming him for a bit we played a few more rounds of suck, kiss, suck until he asked if I wanted to fuck him. I was very much on board with this, so I did. It was an interesting experience because I'm not hung like a horse or anything and he's taller than me. It took a few positions to find the right groove. After fucking him for a while we just jerked off until we came. I took a while, chalking it up to performance anxiety.

On another side note, in what was probably the most intimate moment of the entire experience, after jerking myself for a while after he came I turned to him and laid real close to him. Our faces were so close and every so often we kissed each other really gently. The feeling of our breath on one another's mouth was so intense and sexy. That's what sent me to pleasure town and I came while doing that.

After that, we cracked open a couple more beers and just talked for a while before I headed home. I made sure to kiss him one more time before I left.

So there you all have it! My first experience with a guy and I no longer have my "V card". It was fairly unexpected. If you asked me if I thought this would happen last Saturday I would have laughed in your face. I'm actually kind of bummed out this morning knowing that nothing can really develop from this. He was a really awesome guy and somebody I totally would have been open to a relationship with. I never went into this expecting anything more than a hook up, but there's definitely a standard in place. Hopefully I won't have to wait so long for the next round!
 
Apologies for kind of just jumping right into the story. There was a little more to it, but it got cut off when I copy and pasted what I wrote because the site logged me out. I also apparently can't edit the post because I passed the 10 minute time limit…

Anyways, we just met up at the mall first, ate some lunch and we talked for a bit before he suggested we go to his place for some beers. The key element in this part of the story was that I was really nervous leading up to everything, which is where first paragraph above comes into play.
 
That's actually a good first time experience. He sounds like a nice guy and hopefully the two of you can stay in touch even if he has moved away.
 
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