I brought Michael (Mike) back for another shoot, because I wanted him to take things one step further than the last shoot he did. When Mike arrived at the studio I had him take a seat on the couch and figured we would talk until I confirmed that he would do what I had planned in the shoot. I asked Mike if he was ready for my surprise and he had no idea what I was going to ask him to do. Starting out, I asked if he had been enjoying the money that he had been making and Mike responded that he had spent most of it on doctor bills and made a car payment. The last shoot he did was oral, and he admitted that giving head wasn't that bad. I had him remind the members who he was--19, straight, and currently without a girlfriend. Coming clean with Mike, I wanted him to try anal sex, and when I told him I would pay him $1000 to have a dick up his ass, he turned me down. Then, I offered for him to try doing the fucking and he still wasn't all that excited about it. Going back and forth, I could tell that he just really wasn't sure about it. That's when I decided to bring in Drew, and when I called out for him there was a knock at the door. In walked Drew taking a seat on the couch and I explained all the different work that he has done since he started here with Broke Straight Boys. Introducing the two of them to each other, there was some awkwardness there, but the two of them shock hands. I explained to him what was planned for the shoot and that Drew was down for doing anal. Knowing that this was going to be Mike's first time fucking a dude, he did say that he would give it a shot. While I put on some porn, I asked them to get undressed down to their underwear. Both of them stood up and undressed at opposite ends so it was hard to film them both. Taking a seat on the couch, they reached inside their underwear and started to play with themselves. As they worked on getting hard, I noticed that Mike kept looking over to see how Drew was coming along. Last to come off was their underwear and when those came off Mike's cock was pretty much a full boner. I asked Drew to go ahead and start sucking on it to get him as hard as possible. Drew worked on giving oral to Mike and after a few minutes I asked Mike if he was enjoying it. His response to me was yes, and he seemed to enjoy watching it. I complimented him on how nice his cock looked and the guys were ready to get the fucking started. Taking a moment they got the couch into a bed, and grabbed a condom to put on. Drew started in the doggie-style position and Mike was able to get his cock in Drew's hole with one solid push in. Mike worked on trying to pick up the pace, but seemed to have some cock issues. He took a moment off camera to get hard again and was able to start fucking again. The guys were good about changing the positions on their own and I think Mike was just a little afraid to get too rough with Drew. I kept telling him that it was okay to pound Drew hard and to go fast, because he can take a good fucking. Watching Drew on his back was the best position for the penetration shots, and to see more of the boys' bodies. Since things were going so well up until this point, I asked Mike if he wanted to try receiving anal for a minute. He wasn't too sure, but I offered him the $1500 that he wanted in the beginning of the shoot, and told him that Drew's dick wasn't a monster cock, so it wouldn't be that painful to start with. As soon as they gave me the green light, I had them change positions and had Mike do it on his back. Drew pushed his way inside Mike's super tight hole for the first time. Reaching back with his hand Mike applied pressure to Drew's leg when he went too deep. When Mike took his hand away Drew started to pick up the speed and was fucking him a lot harder. Mike even started to moan and at one point he even said that he had had enough. I tried to see if I could get him to do just a little more of fucking Drew, but instead he was ready to give me a cum shot. The guys readjusted on the bed to sit against the wall, and as I filmed them jerking off I noticed that Mike was watching Drew jerk off. I asked Drew to suck and play with Mike's nipples to help him get off. That seemed to do it, because seconds later Mike shot his load like a fountain, cumming all over his stomach and chest. Afterward I told Mike that I had to give him kudos for at least trying a dick up his ass for the first time, as well as fucking. I hope to see them do more shoots soon.