If you remember on his last visit, Sterling, still in college, comes in with his straight, best college/surf buddy Jack, to break into porn. They were all excited about getting paid to fuck pussy! But, as you know we're a ''Pussy Free Zone'' here, and when 'the girl didn't show', the only option Caruso had for them to earn a paycheck was to have sex with each other. Sterling was the dominant of the two, so after some half assed swapped blowjobs, he appointed his buddy Jack as the bottom. After it's all over, he realized that he loved the experience and decided to see for himself what it's like when his butt is on the other end of a cock. So, borrowing a girl's dildo he fucks himself silly... and loves it. He knew that it was only a matter of time until he had the courage to try the real thing. The opportunity came when he was recently approached at a party by another college buddy, Ryan, who tells Sterling that he saw him on BaitBuddies.com. Sterling is immediately alarmed and figures that it's all over for him - his secret it out. But, Ryan explains to him that he's also curious and just wants to be hooked up with ''that guy'', referring to Caruso, because he also wants to do a video. The boys talk and Ryan tells Sterling he's a top and Sterling tells Ryan he wants to bottom - all that was left was to call Caruso to set it up... and that's how we got here this day! Sterling tells Caruso that he thought his prior appearance was going to be a one time thing. But, now that he's exploring his sexuality and loves using a dildo, he wants to enjoy life and if this is part of it he's going to do it. Caruso instructs the boys to strip down, Ryan has the body you'd expect from a 20 year old gymnast, basketball player and all around athlete. At 5'10'' and 135lbs of lean muscle topped off by a beauty of a 7.5'' cock, this southern boy from Mississippi is one damn hottie. We are a bit taken aback watching Sterling strip off, his once very lean, almost skinny body has beefed up considerably - he says from daily protein shakes and working out - and on him it looks hot! He's now a big beefy man with a big beautiful bubble butt and killer thighs, all toned and sexy with a hefty 7.5'' dick and big set of balls. Now that they're naked, Caruso tells them to get going. Sterling goes for the kiss, but then stops and says it's too intimate and Caruso laughs and says ''too intimate - this guy's going to be fucking you in a minute!''. So, the kissing comes to an end and the boys proceed to swapping blowjobs. Ryan sucks Sterling's cock a for a little and then the other boy quickly takes over and starts sucking his bud's cock like there's no tomorrow and it goes on for quite a while. He's finally done and Caruso asks ''So, you like that?'' and Sterling answers ''I loved it!''. But, both boys are anxious to get to the fucking, so Caruso tells them to 'suit up' and go to it. Sterling decides he want to get fucked, for the first time with the real thing, doggy style. Ryan is happy to comply and easily penetrates his friend's hole (the benefits of Sterling's dildo practice) and starts pounding away. But, it appears that Ryan is quickly losing steam, he tires quickly for a young athlete and says he's slowing down because Sterling is so tight and he's ready to cum. So, Caruso lets them take a break and cool down a bit before they go back to fucking. Ryan re-lubes and they take the opportunity to switch to missionary style. Ryan starts fucking Sterling's tight ass again and within just minutes says ''I'm going to cum''. There's such urgency that he just pulls out of Sterling's hole, rips off the rubber and tosses it onto his bottom's torso and jacks a huge load onto him that sprays him from his dick up to his neck! It's now Sterling's turn to bust his nut and you see Ryan helping out by playing with his balls. Notice how Sterling's dick looks lubed and shiny - well that lube is his buddy Ryan's cum! Caruso is still kicking himself for not catching Sterling doing the buddy cum lubing on camera. Both boys are now sweaty and at least one of them is cummy too, so Caruso sends them off to the shower room to clean up. Here we see a touching moment when Sterling initiates a short hug with Ryan and just quietly says ''thank you''. "After the Shoot", there's lots of discussion about the fucking and Caruso lets us into a little more behind the scenes and tells us how super nervous Sterling was about bottoming for his friend, among other things. Caruso then invites Sterling to bring in some more buddies, so that we can all explore "The Evolution of Sterling".