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I could have also called this entry "The First Time I Scored a Hookup through Sharing My Pictures Online", but what I went with was more catchy, no?
Still, that aspect of the story was a big deal for me. Before the time I'm writing about, it had never even occurred to me that I meet someone for sex by talking and sharing pictures online. Which is funny, because I had already taken pics of myself - including some that are in my profile here. And I had taken them with the intent to post them online. But my only goal had been exhibitionism, and to see how people would react to my nakedness.
To that end, I posted the pics to a dick-rating website. And lo and behold, I got plenty of good feedback - comments and ratings - on them. Pretty much all from guys, though. Then, as now, the (gay) guys on these kinds of website far outnumber the women.
But after a while I did get some attention from a female or two. One of these very much got my attention, because she had some pictures of her own posted, and they were nice. I managed to get a dialogue going with her, and we soon moved our contact off the site, to email with more pic exchange.
But even by that point I wasn't thinking in terms of hooking up through this. Not seriously, anyway. And that's because A. lived in Montreal, while I was south of her border in Chicago.
But there was a chance! I visited my dad in the northeast once every year or so. I was due for a trip, and it wouldn't be a huge deal to add a jaunt to Montreal to the itinerary. A big deal, yes: two added (international) flights, staying at a hotel for a couple nights, and above all doing all of this without knowing for sure if things would work out with A.
But I was single and horny, and A. in particular made me especially horny - and that feeling was mutual, as she liked the visit idea. So I went for it.
I couldn't possibly explain all of this to my dad, so I kept it a **** from him - and from everyone else in my life, for that matter. Which was stupid, yeah. But here I am, alive and well to tell the tale. Anyway, the idea was to complete the trip to visit my dad, and then fly to Montreal rather than to Chicago. I'd stay two nights in Montreal, hopefully meet A. and have awesome sex, and then return home.
There was a hitch before I even got to Montreal. I figured my dad and I would part ways at the airport, and I'd check in for my international flight without him ever being the wiser. I didn't count on my dad wanting to prolong our visit by waiting until I checked in and, I guess got to the security checkpoint. So yes, inevitably, he learned that for some reason I was going to Canada rather than home. That was awkward. Ditto explaining the whole thing to him, which I inevitably had to do. He was very cool with it, though. Thankfully. I didn't need a big guilt trip and to go along with the already kind of risky trip.
But after that things went great. I met up with A., and she was just as hot in person as she had been in her pics. And she was still down for hanging out, to be followed by "hanging out".
A. was in her late 20's, slim and fit - she worked out all the time. And she was arab. That was good for me, as I love women with dark hair and eyes, and dusky skin and an exotic look. She had all of that in the best way.
A. ended up being a little conflicted about actually hooking up. Well, why not? This was our first time meeting, after all. So even when things started to heat up, back in my hotel room after a dinner (which she treated me to! I guess she considered me her guest), she played coy and was tentative. But that didn't last. Next thing I knew, we were making out, and A. was lying on the bed as I got on top of her, my hard-as-hell erection pressing into her for the first time. "There you are," she said to me with a sultry look. Up until that point she couldn't have been sure if I would live up to my photos, if I was really sporting the size displayed in them. That moment of my bulge hard against her was enough to prove to her that all would be as promised, and that comment from her said as much.
So we got naked, and got into it. And it was so, so hot. One moment from that night that is burned in my memory: A. on her back, her long silky raven hair laying out around her head. I had only just penetrated her and slowly started stroking. And her face had a look of lust and pleasure that bordered on looking like terror. I was almost alarmed for her because of that look - but mostly very turned on.
By the way, A. had big tits, which was nice, although their shape was a little odd. Big nipples, too, and they had a curious look of being kind of pinched at the base, as though she had tiny rubber bands around them. They were fun to lick and suck.
We only had the two nights to work with, and we made the most of them. The next night we had dinner again (and A. paid again!), but some hookah smoking (actually called shisha, as I learned). A. was literally giving me a taste of her culture - the dinner had even been to a restaurant of her home country's cuisine. On top of that, we went to her place after the dinner rather than to mine, so I got to see how she lived, and some of the special things she had from her home country. But never mind that cultural stuff: the sex was again great. Pretty straightforward - not even oral sex by either of us, if I remember correctly - but super hot.
I had a morning flight to follow that decidedly late night, so it was a groggy trip. Worth every bit of it, though - expenses and all. A. and I kept in touch for a bit after that, but it inevitably fell off when it became clear that we wouldn't be able to see each other again any time remotely soon. And so, we never did see each other again. But that image of her beautiful pleasure-terror sex face lives on in my memory.