I found a similar scene in HazeHim: Flash Jacking Around Town (HM6817):
So, this pledge is fucking a fleshlight next to another pledge's ass. The frat bro points to a condom and tells him to take it on and fuck the other pledge instead.
He takes the condom on (out of frame) and get's ready to fuck.
His cock is semi-hard at best, but he does his best to work it in, slides back out, tries to get it hard, gets back in…
Then there's a cut, and now he's jack-hammering the other pledge
In the closeups, you see that the condom is gone and his cock is now unprotected and rock hard
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He fucks for a good while, before pulling out when it's time to cum. Now he rubs his bare cock up and down the ass crack
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He sprays cum all over the pledge, from his neck to his crack
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