hooooooookay this is a messy topic (no pun intended) to deal with. Truth is, no matter what mykel73, myself, or anyone else says here, the fact is that we are all just pulling guesses out out asses (again, no pun intended. i really need to stop punning lol)
Instead of asking a bunch of total strangers on what it sounds like purely based on your P.O.V (Point Of View), go and talk to him and ask him where, when and how he loosened his ass up. Explain to him that no matter his answer you will accept him etc, and he will tell you, though he may be lying. If he says outright 'I've been masturbating with anal play' or something along those lines, without hesitation, then he is most likely telling the truth. If he tries to avoid answering, or he hesitates alot and/or stutters, then he's most likely lying.
To me, it sounds like he's either doing it himself, or he has found a shemale, or possibly another male, around town to experiment with; But as i said, it is just a wild guess. All in all, it depends on how good you are at reading people when the react. Also, watch his eyes when he answers. If they point down and to the left, he is lying through his teeth, but if they point up and right, then he is telling the truth. Just my 2 cents
