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Remember Jack? Well, Jack is back after 6 long years! Jack had his first gay for pay experience right here at the studio and now he doesn't really care to label himself. He knew he liked girls but now he loves having sex with guys just as much. And, now that Jack's more comfortable with his sexuality, he's ready to swap positions and bait a straight guy into going gay for pay!

Devin Tyler is this week's straight guy and he's one good looking dude! He's 28, hot, hung, and horny but he isn't very kinky. He tells Caruso that he almost had a threesome but he was too shy so he left. And, even though he's had several girlfriends in his 28 years, he's never fucked any of them in the ass. He even told Caruso that he never really wanted to either...

Caruso knows this might be a challenge so he tells the guys to strip down naked, watch the porn that's playing on the TV in front of them, and work their cocks up. Both guys were rock hard within no time so Caruso stepped out to check on the female talent. He returned with bad news... no girl will be showing up today but if both guys will have sex with each other then Caruso can double their money. Devin quickly reminded Caruso that he doesn't do anal. That means fucking in the ass as well as taking it up the ass. As usual though, money talks and Devin's cock wasn't going down any time soon so he decided to give it a shot and the results are amazing!