His hole looks a bright red and not in the least bit damaged yet. It's always a wonder to me that a user who is 22 years old can have a pristine hole - most of the time this is not the case. Well, he might have gotten this far with his cherry intact, but it's the end of the road for this untapped resource. Just to add to his humiliation (I could see his roomie watching the whole ordeal), I have him lube me up and try to stick it in himself. He wasn't successful, so I shove it in myself. It took about the average amount of time to get him loose enough to fuck. Once I start really fucking him, ...

His hole looks a bright red and not in the least bit damaged yet. It's always a wonder to me that a user who is 22 years old can have a pristine hole - most of the time this is not the case. Well, he might have gotten this far with his cherry intact, but it's the end of the road for this untapped resource. Just to add to his humiliation (I could see his roomie watching the whole ordeal), I have him lube me up and try to stick it in himself. He wasn't successful, so I shove it in myself. It took about the average amount of time to get him loose enough to fuck. Once I start really fucking him, he starts with the wincing and faces. That might work on most people, but not on me. I repeatedly pull all the way out and dive back in, making sure he gets it deep.