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I didn't start out to do that. I was just out sitting by the river reading on my kindle when I realized that it had gotten dark out and that I was out after curfew. I was sitting under a gazebo in a place that for some reason, didn't have any lights. As I was sitting there trying to decide what to do, when two of our homeless guys wandered up. They were both younger black guys and pretty typical. They just kind of stood off to the side for a long time and I just ignored them and kept reading. Finally one walked up and asked if I had any change. I have no idea where this came from but I told him $50 for each of you if you fuck me raw right now. I was as shocked as he was. He just stood there and looked at me, then went over to his friend. They converses a but then they both came up to me and said "lets move a little farther into the dark". My heart was a ponding. There I was in the dark, sandwiched between two homeless guys. The second guy took charge. He put his hand on my head and pushed me to my knees. "Go for it faggot". It took a bit, he mad multiple layers on, but I got his cock out. About 7 uncut inches. He pushed my head into his crotch and it was all I could do not to gag. He hadn't washed in a a bit. I got used to it as he got hard in my mouth filling it nicely. My brain was shut off at this point and I have no idea how long he fucked my mouth. He then grabbed my hair and pulled me to a standing position, bent me over the railing and pulled my shorts down. I heard his spit and felt a wet finger in my ass. The finger pulled away. A dirty rag was stuffed in my mouth and then all the sudden all 7" of that hard cock were shoved in my ass all the way to the hilt. Oh my god. (now I know they the gag, I screamed). he just stayed there for a bit then started fucking me. It was rough at first, but is got smoother,, and it felt like there was lube there all the sudden. There was no finess, just raw fucking. He lasted a good 10. min and then he grunted and shoved it deep in me. As he pulled out he smacked my ass hard. The other guy now grabbed my hair and pulled me to the grass and pushed me onto my knees and told me to to get an my hands and knees. The first guy came around and put the cock that had just exploded in my ass into my mouth. Well I now where the extra lube came from. I could taste blood. He laughed and said. "Well If you think that hurt, wait till you feel this". The second buy must have been stroking as I was getting fucked. I could tell there was someone behind me and I felt this monster hit my ass. He put it to my hole and started a steady relentless push. If there wasn't blood and cum there he would have ripped me open. It seems like it took forever but he bottomed out and then just started a steady attack on my ass. he lasted another 10 min so and then he pushed in and got even harder all the sudden. He just stated here balls deep for what seemed like ages. As he pulled out I hadn't really recognized the fact the first guy was hard again. He pushed me flat onto the ground and just started fucking again. The second guy hit my face with his softening cock and I swear that thing had to be 11" and pretty think. I stretched my head up and started trying to clean him off as I got fucked again. He never really got soft and mostly because I wasn't flexible enough to reach it all, couldn't get it lal in my mouth. The 1st came in me again and then pulled out. The monster cock wasn't really interested in any more. As they pulled their pants on, I reached into the pocket on my shorts and pulled out all that was there and I tossed it onto the ground and fell back. Have no idea how much was really there, but they were happy. I wonder if they are going to be looking for me as much as I'm probably going to be looking for them again. I've let homeless guys fuck me before, but this was the first time like this.

I've been messaging on-and-off with this guy, and a few days ago he told me he'd always fantasised about seeing a guy jerk off for him - and then using the guy's cum for lube and fuck him directly afterwards! "Well," thought I... "I have a cock, I have an arse... I can help with that, right?" So a few evenings later I showed up at his apartment, got naked on his bed and started putting on a show for him while he was sitting in a chair in front of the bed. You know; wanking myself furiously while licking a finger wet and then fingering myself. He told me to get up on hands and knees and then he took over, milking me from behind while rimming my hole. He ordered me to make sure that when I came I'd catch my load in my hand and not waste a drop on the sheets of the bed - and pretty soon I did just that! Damn, it feels good to cum with a tongue in the arse... He told me to stick my hand backwards between my legs so he'd have access to my cum - and then he began fingering my load into me, little by little. When he was done with that he took my hand and folded it around his hard cock, lubing it up with the last bit of my cum left in my hand, and... Well, you know how it goes; the willing bottom slut takes a few deep hits of poppers, the top begins pushing his hard cock head against the hole and at some point it says "pop" - at least mentally - and the cock enters... And yes, it IS harder to take a cock once you've cum, but so be it. I had said I would, so of course I did. And it was hot as hell to know my own load was lubing my hole! Of course he came deep inside me, which was even hotter, and by then I was fully turned on again by getting fucked, and even squeezed out a second, smaller, load as he did. Once again I caught it in my hand, and as he pulled out he saw my hand with the sperm presented between my legs just as the first time... He forced my hand up flat against my hole and worked it around a bit, smearing my load on my hole and buttocks - and then he once more began rimming me, seemingly very much enjoying the mix of our sperm on and in my fucked-out hole. NICE! And I wasn't the only one who thought it was nice, because suddenly he pulled his face away from my arse and once again his cock entered me! Bonus... We hadn't discussed that in our messages - but then, nor had we discussed me cumming twice, so hey; it seemed only fair that I should have to take his cock again!... The second fuck was shorter than the first, and it definitely felt like he just wanted to dump a second load for the sake of it. Quick, frantic pounding deep into me, and within minutes he was moaning as he shot his second load in me. This second time around I was too spent after cumming twice to even get hard, so my limp cock dangled uselessly under me as his cock gave a few last thrusts before he finally pulled out. My hole felt sore, open and sogging wet - so with mission accomplished I got up, got dressed and left.