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.
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He takes the condom on (out of frame) and get's ready to fuck.
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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…
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Then there's a cut, and now he's jack-hammering the other pledge
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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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