Diary of An Unrepentant Sex Addict

Thursday, November 29, 2007

OK, Cupid, Maybe You CAN Get Me Laid

I've actually had very little success with the OKCupid matching site. And that's a shame, really, because I love their tests and I think their approach to questions (allowing multiple "right" answers, weighting the importance of various questions) is probably one of the best thought-out of the dating-website diaspora. And yet, until this week I'd never gotten lucky with anyone I met there. A number of first dates, but rarely a second date.

And then, this happens. I'm currently in Denver, and will be for a few more days. Last year, when I lived here for a few months, I'd tried to date a little using OKC (and a few others) as a source, to no avail. I don't remember how I found the particular ad, but after moving back to California I stumbled across an ad from someone in Boulder. An almost idea match-- polyamorous, close (-enough) to my age, and many shared interests including Russian. I sent a brief e-mail that basically joked, "Where were you last year when I was in Denver for 8 months?" Funny-enough, she wrote back and said I should drop her a line next time I was headed to the area. So a few weeks ago, I did. But this story actually isn't about her, and you'd probably prefer I get to the sex part, anyway...

When I wrote to her, as is the wont of OKC I saw a few suggested profiles for people in the same general area that are similar (by OKC's measure) to the person I just wrote to. One of them really caught my eye, as her views on sex and poly relationships was very close to mine. I was hesitant, though, because there was a larger age-gap than I would normally pursue. But I sent a fairly harmless message anyway. She replied and seemed to be really interested in me. We exchanged some OKC messages, and moved one evening into actual chat. Started on OKC, moved to Yahoo IM. I still wasn't sure she was actually interested in getting together, but the chat was enjoyable.

Then it started getting slightly suggestive. I was being a good boy, I swear! But after a bit, I had to start teasing a little in return. You know, like self-defense. Sorta. Anyway, so we decided to meet somewhere last Saturday, after she got off work. Picked a nice, reasonably-quiet bar. I got there and immediately recognized her from her pics. Oh yeah... pics. Did I mention that by way of teasing me, she had sent me links ("private guest passes", in Flickr terminology) to several Flickr photo sets she had, that were carefully locked? And for good reason... these included several strip-tease sets, a set from her first orgy (which also proudly pointed out that she herself had organized it), and a set called "not alone", that comprised of pics of her with others (but which did not belong to the orgy set). As George Takei would say, "Oh my."

So, yeah, after deciding that despite a clear case of mutual lust (I had only a few pictures to offer, but sent them in order to be fair) it would not be wise for one of us to drive the 30 or so miles to the other at 2AM for a quickie, we made the Saturday plans. And so it came to be that I was having a pint of Guinness (food of the gods), across from her and her simple white wine. We talked for hours, joking, flirting just a little. And as it was getting late, we left and went to my car (well, the car I borrowed from the friend I'm staying with out here). At this point, I was hopeful but a little unsure... aside from semi-anon hook-ups on Craigslist, my actual dating-life has been pretty cruddy for quite a while. This person was neither a professional, paid to tolerate my advances, nor a fellow CL cruiser, who may have simply decided that I was "good enough" for that evening's efforts. No, this was a real, ordinary person with fairly ordinary dating instincts. But as we sat and contemplated each other, I boldly made the move for a first kiss. And 10 minutes later, we broke off long enough to consider our dilemma:
  • Driving to my place was out because (a) it was 30+ miles away and (b) my friend was already annoyed that I had made a date to spend time with someone other than her (despite the fact that we are only friends, not romantically-involved, and despite the fact that in previous visits she herself had tried to get me laid... I don't understand, so please don't ask...)
  • Her place was out because she currently was living with a parent while returning to school after a few years' break
  • There was no doubt we needed to find someplace, and fast
So we did something I hadn't actually ever had to do before: we found a cheap motel, and rented a room solely for the purpose of sex.

Once in the room, we didn't waste any time. But that was largely because we didn't have a lot of time to waste... it was already late, and she had to be up early Sunday for work. But we had enough time for my two favorite Latin words. Who am I kidding... for me, there's always time for going down!

After we spent more time making out (this time, doing so while deliciously undressed), I kissed my way down her body and took a moment to gaze at her V. Very nice, indeed: neatly trimmed, without any actual shaving. I could play to my heart's content without worrying about either stray hairs or razor stubble. So I went in and started in on my usual tricks and technique. I know I've said it over and over, but I fucking love going down on a woman. I don't know why, maybe because I got conditioned to consider it "forbidden fruit" earlier in my sexual history. But it's just heaven for me. So, I'd made sure she knew that I was a lover of this activity, and also more than happy to go as long as it took for her to get off... I didn't just consider it some obligatory foreplay. And she had warned that she rarely gets off from just oral. But that's OK... I'm just lovin' life, for now. Licking, suckling the clit, lightly nipping the labia, long slow broad strokes of my tongue. After a while, at her request, I work a few fingers into her and start massaging the general area of the G-spot (which I tend to have more trouble locating than the clit itself). But sure-enough, after about 20 minutes or so, she stops me and tells me that she thinks she'd have a better chance of getting off if I continue to use the fingers inside her, but let her work her clit with her own fingers. You know, some guys might take offense at this, or at least feel like they weren't effective. Not me. I'm just happy to see my partner get off, especially if I can have a hand in it (oh, that was a bad pun... sorry). And after another 5 minutes or so, I got what I wanted to see: her in the throes of a great O, so much that almost her entire body lifted up from the bed.

Then it was my turn. As sometimes happens, I had gotten very focused on what I was doing to/for her, and my own excitement had... faded. But she had bragged about her oral skills, and felt the need to back up her bold words. And she did. I can no longer point to a single person as the hands-down "best" oralist I've had the pleasure of enjoying, but she was pretty damn good. When she took me over the edge, I felt almost as if I was coming so hard my feet were shrinking.

Alas, at that point I knew I was spent for the night, and she still had work to dread, err, look forward to. So we parted ways, me driving her back to the bar to get her car, and her saying good-night with a hungry kiss that made me wish it were 3PM instead of AM. But part we did, and drove back to my house and she to hers. Neither of us knowing for sure if our schedules (hers consisting of school and work, mine consisting of remote website work and house maintenance/repairs) would let us get together again.

Turns out they do-- tomorrow morning. And on that note, I need to get some sleep :-).


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