First Date Sex

Another late-in-life thing that I first experienced after moving out west, is the concept of casual sex. Or maybe it's better to say that what I experienced is an introduction to the idea that there is a whole world available where there doesn't need to be so much formality, ceremony, and decorum putting boundaries around your when and with whom you're allowed to have sex with. Up to that time, to me, sex was something that you did only after getting into some semblance of a relationship with someone. You dated them for a little while, letting the physical part of the relationship grow, and then you talked about having sex. Usually a couple weeks or so of dating involved before actually doing the thing. I mean, I should say that I wasn't a naive person. I knew that casual sex was a thing and that it was something that people did. And to be clear it wasn't that I ever had some sort of moral objection to just having sex with someone, casually, just because you wanted to. I actually always kinda liked the idea, it's just that none of my interactions ever really went that way. All my dating, for whatever reason, was of the sort where both parties were aimed at finding a relationship. So it was always with a sort of care and formality, and anxiety that I'd start dating someone. Two people more or less scared of one-another, to be honest, was my dating norm. You know? Like, okay, we do the first date thing. If that goes well we have a more formal date and have more in-depth conversation. If we advance to a third date then you can kiss me. If we both liked that then on the fourth date maybe we find a place to make out, etc. Maybe a couple weeks later if you do all the right things you can put your penis in me, but no promises, we'll see how it goes. Really conservative, and honestly for no apparent reason that I can think of. I was just sorta convinced that was the way you were supposed to do it. Weird, right? Like who ever made those rules, anyway? When I moved out west, I made a lot of big shifts, and got introduced to a lot of new things. And in general, the whole dating scene was vastly different. It really felt like a whole new world -- the way people met one another and hung-out was different. There were larger groups of friends that would be all acquainted with one-another, for example, and it seemed like there was a lot of very casual dating and much less formal rules around it. The use of dating apps like Tinder and OKCupid was much more prevalent, and it seemed that people were dating ALL the time, like as much as many times per week with different people. Within a few months I'd started-in a bit with the dating scene, and early on I had a couple different occasions where it was really nice to dispense with a lot of the formality around it all. It was way more fun! Like, rather than "dating," it was more like just meeting a friend for a drink and just seeing what's what. Like, what do you think? Wanna see where this goes? On a particularly fun fourth outing with a guy, we went to a dance club, got a little tipsy, made out in the parking lot, and I ended-up letting him nail me in the back of his car. A little crazy. The sex was a little awkward and not really that great, but it was FUN. It felt CRAZY naughty. The first time I ever really cut loose and totally talked dirty, during. Something about the naughtiness of it grabbed me, all 'oh GOD yeah, FUCK me!' I think I'd known that guy for just over a week, and that was the soonest I'd ever had intercourse with someone after first meeting them. I loved thinking about it. The next day and for several after it was like 'holy shit did we actually fuck?!?' Not too long after that one, I was corresponding on OKCupid with a guy for quite a while -- quite a while longer than normal before actually meeting them in person. We had some really great conversations online, but kept missing one-another as far as meet-up timing. He wasn't at all shy about letting me know that he was really physically attracted to me, from my photos, and the way he put it I thought was incredibly endearing and sweet. When we finally met-up for late afternoon drinks and snacks, it was truly one of those amazing moments where you can just kinda SWIM in the chemistry. Like, he wasn't the most gorgeous guy in the world, and I'm not the hottest woman in any given room, but the magnetism between us was crazy-heavy. Right from the start I wasn't myself, and was just feeling so turned on. Our conversation was AMAZING!! I can't even really remember exactly all the stuff we talked about, but it was like right off the bat there was no small talk, we just had serious emptathy for one-another. I don't know how else to explain it. It was sweet, kind, fun, giddy, soft, gentle, effervescent. The space between us was redolent with delicious, sensous, sumptious romance. One weird wrinkle was that we'd both ridden our bikes to the place and as it turned-out we were close to each other. I asked if he wanted to take a little spin with me -- maybe we could find a cool spot to watch the sun set over the city. (To be clear, I knew exactly where I wanted to go: a little secluded park space on a bluff overlooking the river and with a view of the cityscape. I knew it would be an amazing spot to make out). He heartily agreed. We sat down on a bench together and I swear I don't think we said three words after sitting down before our lips were smashed together. It was so thrilling! It felt like the first time I'd ever kissed someone, I'm not kidding. I was absolutely flushed with arousal and a deeply satisfying warmth. It felt SO good! It was amazing on every level. It felt like getting high. I was lost in the way those soft, warm, wet kisses felt. Damn. It became to awkward to continue on the bench, so we transitioned to lying on the very small, grassy hillside. The evening was slightly chilly, but warm enough to be out in it. We continued making-out, tongues deeply entwined with one-another (that sounds so corny but it is definitely descriptive). His hand was on my hip; I took it and placed it on a breast. Soon both were there. The space was private enough and it was dark enough that I lifted my shirt and pulled my bra up. It felt so hot to show him my tits. And I had never so completely enjoyed the feel of hands on my boobs as much as I did in that moment. We were getting to the point where we were gonna have to decide if we were going to call it a night or take it somewhere else. I think I said something dumb and very simple like 'would you like to have sex with me?; He said yes, and I asked if he could tell me anything to reassure me it would be safe. And I loved what he said because it was really what I needed to hear which was that if I had any doubt then I should just act on that and do or not do whatever I felt okay with. It wasn't a rehearsed line -- it came from the heart, and I decided right then that YES! 100% I wanted to have sex with him THAT night. We had to negotiate on the logistics -- we decided we weren't comfortable just getting on with it right there outside. I was living with roommates at the time and I didn't want to go through the awkwardness of bringing some dude that I'd obviously just met back to my room. He lived alone so we rode over to his place. The whole way over I can remember having HUGE jitters, but I was SO excited!! It was so much fun, all of it. Getting naked with him felt so deeply satisfying. He had a GORGEOUS body! Seriously athletic, and -- oh my -- a lovely cock! Every fiber of my being confirmed to me that I'd made the right choice to go home with him. But still, at the back of my mind, the wheels were so crazily turning over! All the old habits! Like, babe, this is your FIRST date with this guy! The kinds of questions you're supposed to be answering are what kind of music you like, not 'is it okay to cum in your pussy?' Like, when I was getting ready to go out earlier that afternoon, I was not thinking that I was…