First load in a very long time

There's a guy I'd messaged a couple of months back on a particular site. Hot profile and pics, way better than average, and very close to my ideal body type, thin with a little definition and not too tall. We messaged quite a bit then, but otherwise didn't have any contact since then. I get another message from him around the end of May. We do a whole lot more messaging this time about lots of things and bit by bit I'm probing for information. We're both versatile tops, but he mostly tops. From his pics, he has a cock that would be a perfect fit for my hole. But his profile also says "Safe Only" so I'm trying to find out if he might fuck me bare.

sdsk8rboi: when topping, where do u like to unload?

sdhotboy: haha, i'll unload anywhere

Possible, but not conclusive. Later:

sdsk8rboi: thought i'd show you some pubes, haha.;) when topping, do u like a hole that's smooth, a little hair, doesn't matter?

sdhotboy: i LOVE pubes ;)...urs r awesome dude, really doesnt matter...in fact i think if its shaved the "stubble" can probly b uncomfortable

At this point I'm thinking he might just fuck bareback. How are you going to feel stubble while wearing a condom? You can't feel much of anything. Then later once we've made plans:

sdsk8rboi: whatever we do, i want some of your cum in my butt. ;)

sdhotboy: ok!! ;p


After a week or so of lots of messaging, way more than for any sort of typical hookup, we arrange to meet the following weekend and have him possibly fuck me. This was not the endless stream of messages that often go nowhere, but more the getting better acquainted before actually meeting variety. On a Sunday evening, we meet at a secluded location. I won't say where except to note that San Diego County is a big county and there are plenty of secluded locations, even with all the people. Nothing sleazy about the location either, not that there's anything wrong with that either. The location is secluded, but not quite secluded enough for me to be totally comfy. No surprises from his pics, totally hot. We seem to mesh well otherwise too. I'm very comfortable with him, though not totally comfortable with the location. We sit there together mostly talking for a couple of hours about lots of things, about half naked. Not totally naked because it was kinda cold. We don't do much more than suck each other and nobody cums. Naked, in person, as in his pics, he has a most awesome body and cock. We're both fine with not doing more then. I'm slightly nervous about the location and also concerned that it might have gotten messy if he'd tried to fuck me then. I didn't want it to be that way. You try to prepare properly, but it doesn't always work out as planned.

However, otherwise it worked out great and we agree to meet the next weekend. This time I'm a lot more comfortable. I'm already totally comfortable with him, but now I know the location and this time it's a little more secluded. It's also not as cold so that's good too. He plays with my cock some and then sucks me some. I then suck him some. He asks me if me if I want to have him try to fuck me, leaving me an out if I don't. Though I haven't bottomed in a very long time, I very much want his cock in my ass and his load too. He's told me on more than one occasion that he's not that experienced, so I guide him through the process. I haven't bottomed in a long time and my hole is very tight. I apply lube, then gradually work in one finger, then two, then three. I ask him if he's okay with being on his back first, letting me ride him as it's usually easier for me to loosen up more in that position at first. He's fine with that. I apply lots of lube to his hard, BARE cock and more lube to my hole, take a hit of poppers, then begin to lower myself onto his cock. It feels good, but there's definitely some pain. I lower myself about half way down, then pull off and apply more lube. We keep doing more of this for a few more minutes as I loosen up. We finally decide that for him and for me, on my stomach will work best. More lube is applied. When he goes in most of the way, there's quite a bit of pain, but only half way, not so much. He adjusts to going in not so far. I ask him if he'll be able to cum that way and he says he will. He gets a decent rhythm going, mostly going in about half way but occasionally farther. There's a little bit of discomfort, but mostly it feels really good. After a few minutes I say, "I want your load in my hole". Less than a minute later he says, "I'm cumming" as he starts to unload, First there's the feel of more smoothness as the cum starts to act as lube, then the warmth. He tells me that he's so glad he didn't JO the day before as he was able to cum faster. I think it was a big load too as I was still expelling bits of his cum for almost 24 hours. Afterward we talked for awhile longer and were there for over three hours though it didn't seem nearly that long. We'll be meeting again soon. I want that second load.