My early sexual (and dating) career was pretty unimpressive; frankly, I didn't really know what I was doing in those departments. But over time I gained confidence in and awareness of my sexuality. I also gained some pretty kick-ass dirty photos that I took of myself - if I do say so myself - for the fun of it (they are among my profile photos here). When my last long relationship ended, I decided to try putting those two things to good use with some online adult dating.

A couple of years of lots of fun ensued; my stories of "The Time I" in this blog have/will mostly come from that period. Including this one.

Now, I was all for one-time meets through my online dating. But I was more interested in ongoing partners that I got along well with in nonsexual ways too. Friends with benefits. That said, my ideal was to have more than one FWB at the same time: for more sexual variety; so that I was more likely to get booty when I wanted it; and, yes, for the conquest aspect of it. Because multiple simultaneous FWB's is a pretty fucking cool thing to pull off.

Over time I learned how difficult it would be to get one good FWB, much less multiple ones at the same time. And yet, fairly early on in this period in fact, I did manage to make one such friend, and then another shortly afterward. Both were great, and easily met my needs, if you will, so I didn't feel the need to look for any more than that.

For a while, anyway. The thrill of meeting someone new, and of potentially achieving an even bigger conquest, soon got the better of me. As luck would have it, another good opportunity came along, and boom! Three simultaneous FWB's.

M. was the first one. Black, tall, fit, considerably younger than me (she liked her guys older). HUGE tits. She got very wet and was an easy cummer; she almost always came at least twice, and sometimes three times in a session (never more than that, though). She was super cool and fun to talk to, which we did for quite a bit before every bout of sex. She also had the downsides of pussy juices that I did NOT like the smell of, and a tendency to scratch my back all up while she was in the throes of ecstasy (eventually I got her to keep her nails short to get rid of that problem); but her positives easily outweighed these negatives. My FWB relationship with M. was the longest by far; we did our thing about once a week for over a year.

K. came onto the scene a little later. She was fairly short, with a broad build (though she was fit; she ran marathons). Large and nice breasts and nipples. Very pretty pussy, with blonde carpet to match her drapes. She had pale skin that become very flushed in the chest and cheeks when she had an orgasm. As with M. I really got along with and liked hanging out with K. Personality-wise, she was very much my type in terms of the kind of person I like to date. And in fact, our FWB relationship felt a lot like dating. We had non-sex activities (we even got together one night without fucking!). She cooked for me. We took turns hosting. It was nice. And it was frequent; we had a couple of trysts a week. But it didn't last very long - it was over after a little more than a month.

T. was tiny, and her figure was literally girlish (except for the nice round ass). Her tits were also tiny, although her nipples, surprisingly, were very large. She was Mexican, though not obviously so since her hair was very curly and she colored it blonde. T. and I got along fairly well, and we even had a couple of outings (a movie, meals out) that made it feel like we were dating. I didn't relate to her as well as I did with M. or K., though. Part of that was due to a slight language barrier (English not being T.'s first language; and I do speak Spanish, but it's not my first language either) and the fact that we came from different backgrounds. And whereas outings with M. and K. were regular, they were maddeningly rare and inconsistent with T. Over the course of several weeks we only managed to get together three times, thanks to the difficulties of her coming over from the suburbs and having various other things going on in her life (which I never knew the full extent of). They were three very nice times, though.

Three good (to great) simultaneous FWB's; I really lucked out there. The actual overlap between the three of them was a short-lived two weeks or so, but during that period I was constantly amazed and thanking my stars for the whole thing.