Freshmen: Issue #216 – Derek Caravaggio & Cristiano Cruzo Flip-Fuck


This first taste of newcomer Cristiano Cruzo breaks our own rules. This flip-flop double day special with Derek Caravaggio (KinkyBoys Web Choice 2020 “Best Solo” Nominee) comes prior to his official introduction which you will see early next year.

This is still an early scene for him, as well as his very first flipflop.

Cristiano is not submissive, however he does like to take guidance from more experienced guys. Derek is happy to oblige. Derek planned to be the top for the first part.

However, once our eager newbie began to eat his ass, he became willing- even eager- to change his plans as Cristiano gently slides his dick in to start fucking. As this is Cristiano’s first outing, we’re keen to hear your thoughts on our hunky newbie.


The urban dictionary defines “flip flop” as “When two guys are having sex and they both take turns being the bottom.”

While this may be so in real life, porn world works differently as we generally film these over two days with the boys alternating roles each day.

So, we rejoin Derek (KinkyBoys Web Choice 2020 “Best Solo” Nominee) and Cristiano the morning after their first tryst. Cristiano surprised us and Derek when he took on the role of top. Now it is Derek’s turn to show the newbie how it’s done. For now, we believe Cristiano is better as a bottom than top.

However, given his eagerness to top, we feel he’ll get better and better. There’s a lot of guys wanting to get a taste of his big fat dick that are hoping this is the case.

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