There is one vide (with condom I'm afraid) from timtales with CutlerX and David, Cutler fucks his ass good and David can hardly handle it (correction... he can't, but Cutler just keeps on fucking him).
And another one (with condom) from papicock with Baby Star and King Dingo where he can hardly handle it, but manages anyway (but still hot).
There was one video I saw with asian boys in pain (also with condom) where I think it was only the one that was any good... and I can't remember which one...
His First Gay Sex: Sean Gold Fucks Jesse Bryce - with condom, but rough and he's in pain
Machofucker - there are some that come close like Black attack, Jiggy man 2, I think one is called Blacked
Treasure Island - there is the scene with Jesso O'toole and Sean Storm (I think cumsloppy buttholes)
and theres Sugardaddu with Arpad Miklos where the boy has a hard time taking the cock...
And Black n large 5 where in the first scene he has trouble taking all that cock...
and rawstrokes with Creampies only allowed, where one of the scenes has a guy that can hardly take the cock and seems to be in pain
... and i think that's it... please let me know if you know of any I missed
In the sucking department I like Gag the fag and one which is called Bone head (and they are treasure Island)