I brought back Corey our designer/makeup artist from BrokeStraightGirls.com, because he wanted to do another shoot for us. He loves the straight boys and getting them to do things that they wouldn't tell anyone else they tried. I decided to pair him up with Derek, who has been with us before. He has a girlfriend, who has not find out where all the extra money has been coming from. Now, Derek has done a solo shoot, his first oral experience with a guy, and looked at taking things a step further. We talked about him doing a strap on shoot with a girl. Corey said that he would line a girl up to do the shoot, but right before the shoot she bailed. In the hopes that we could still make something happened, I just figured that we would supplement the dildo for a real thing with some more money. When I brought up my proposal to Derek he was not having it, he even threatened to leave. I found it fascinating that he would let a girl bang him in the ass with a strap on, but that he wasn't going for the real thing. Derek was very strapped for money and I knew that he needed to get himself out of a crunch, so if I just hit the right dollar amount that he had in his had in his head. We settled on him topping a guy instead of taking it for now. Once we settled on an amount I figured that we could bring in Tyler to do the shoot. I asked Derek what he spent his money on that he has made, and he said that he paid for Lasik surgery. To get started I had Derek strip down out of his clothes, and he was left standing there naked. Taking a seat on the couch, I told him to play with himself for a minute to get hard. I noticed that Derek still shaves his pubs, and that he has a tone body. While he was stroking I asked Corey if he wouldn't mind helping Derek out with some head. Corey was excited at the chance, and so he stripped off his shirt and got down on his knees. Using his tongue, he licked Derek's balls to get him turned on. Then, he took over control, and started to give head. It took no time for Derek's cock to get hard as a rock, and about that time there was a knock at the door. Tyler came in and took a seat on the couch besides Derek, and it showed to be a little awkward. I brought up the fact that we really wanted to see Derek get fucked, and didn't know if Tyler would want to help out with this being Derek's first time. Tyler seemed down, and Derek wasn't making a scene since I was changing what we had discussed. Taking off his shirt, I told Tyler to give Derek oral for a minute, and that was when I told Corey to join in as well. Both guys were down there sucking and licking Derek's dick, and he loved it. I left them alone for a while so that they could just help Derek relax before we got to the point that he would get to take a dick in his ass. When we got to that point, I told Tyler and Corey to go ahead and get all the way undressed for us. That way we could get the fucking started. I had them give Derek a couple of pointers for his first time, and Derek laid on his back with his arms behind his head. Tyler got his cock hard, and he started to push his way in. I just reminded Tyler to go slow, and Derek seemed to be taking the pain pretty well. Tyler started to work up a paced, then he was able to pick up some speed. To help make him relax a little more Tyler played with Derek's cock to help it feel better. Corey licked Derek's nipples and then took over stroking Derek's cock to have a purpose in the shoot. Tyler started to pick up Derek's legs and lift them higher in the air, so that he could do a little deeper fucking. As the legs came off the bed, Derek's breathing started to get faster and louder. With getting to go deeper, Tyler even let out some moans while he just kept up a constant speed. The best was when Tyler got Derek crunched up in a ball, and with his ass up a lot higher, Tyler was able to get his cock in as deep as possible. This was causing Derek to be in some more pain, and there was just something hot about it. What was great about Tyler was that he was treating Derek like a little bitch, and being more aggressive with it. I didn't want to waste much time, I told Corey to get a condom on. When they switched I wanted there to be as little pause in fucking as possible. This way Derek wouldn't freak out and make us stop with a long pause in between. Corey pushed his cock right in there and just started to go really fast ignoring Derek yelling out. Tyler even made a comment about how rough Corey was being for always being a bottom. Tyler stroked his cock, and Derek's as the same time. The guys were so into fucking Derek, that they didn't want to stop fucking the virgin hole. Derek just kept yelling out the money to remind him why he was doing it. When I panned over Derek's face he was actually opening up his eyes a little bit, and Corey was really going to town on Derek's ass, and loving it. He made a face at me too that he wanted him to take it. They worked themselves down, and Corey pulled out about to cum in Derek's ass. I didn't want that to happen, and as Corey was about to spray his load, it just went away. I told them all to take a position, so that we could see them all get off. Derek was the first one to shoot his load right on his stomach, he came all the way up his chest. Followed by Corey who shot his load clear up to his nipples and I guess the fucking had him horny. I didn't even get panned over to Tyler in time to catch him shooting, but his load hit him on his face. All the guys did a great job, and I complimented Derek on taking the cock like a champion for his first time.