From the moment I hit Elliot up online, he was eager to meet up. It seemed to me like he was in some sort of financial distress, but I didn't know the half of it at first. The second time I fucked him, it was a Sunday night. I didn't really want to go pick him up, but I'm glad I did. Of course he didn't have a car, and he lived so fucking far away that even the ride-share was kinda pricey. I thought I'd try to hide a camera in a bag. It turned out alright, but I really need to buy one of them little square cameras and attach it somewhere inside the car; that would be much easier. Since I agreed to meet up with him even though I preferred not to that night, I got a good discount. He explained to me that he has a meeting with the cops the next morning and thought he'd need the money. He'd already been arrested 8 times in the past year and was on probation. You wouldn't tell by looking at him that he gets into so much trouble: He is 19, has a baby face, and is a sweet guy. He tries a bit to put on a macho persona, but it doesn't really suit him. Once we were back to my place in the bedroom, I didn't waste much time getting my tongue into his straight teenage hole. He seemed to like being rimmed. As a matter of fact, he seemed to like all of it. He was rock-fucking-hard while he was sucking my dick, too. He complained a bit about not liking a dick in his mouth, and preferred anything else but that. So he said. But I could tell he loved wrapping his lips around my pole. Either that or he was just eager to get it in the bum. He is a tight motherfucker so I made sure to get him as loose as I could with my tongue and fingers before I delved into his treasure trove. I used a lot of lube, because he is so tight. Also, I took a bit of time working it in. I really wanted to loosen him up slow in order to go ham on him once his ass was ready. I fucked him in missionary and then I had him ride me. Damn if he didn't whimper like a little bitch while I was barebacking him! He almost sounded like a chick. It's always funny seeing how these "straight" boys act when they are getting fucked. Some of them stay in character and grunt a lot, but some just let it all out. He even bit my pillow as I laid him on his side and started hittin' it from behind. Despite me thinking that he might be enjoying it, he definitely had had enough, because he started asking me when I was going to cum. He did it in a polite way, though, so it didn't piss me off. He was like, "are you close, are you close?" I got close soon enough, and I dumped a nice load deep into his teen hole. He was hard while I was fucking him, so after I pulled my dick out, he got himself off while I was caressing his smooth torso. Afterward, he was all smiles, too. I'm not sure if he was happier that it was over, or that he got the measly amount that I gave him for his time. The next day, I was wondering if my jizz was still inside him while he was meeting with the Sheriff. I hope it was. Regardless, it wasn't a lucky charm for him, because he got carted off to jail and I haven't seen him since. He has called me from jail (a lot) and I even put some money in his commissary account for Christmas. I figure I might get some free or cheap ass when he gets out. Since then, though, I've blocked his number, because he was blowing my phone up after that first deposit. Every once in a while I'll get a text from an unknown number asking for money for him. I'm not sure who it is, but I did put a bit more in just this morning as I was getting the video together. Why? Because his ass is so sweet, and I'm hoping to get some more of it, and the footage made me think how much I'd like to fuck him again. Hopefully he'll be outta the slammer soon.