I agree, it’s a hard one, but if all us jerks work together, we should be able to pull it off.
I’m reminded of an old episode of Dennis Miller Live. Jon Stewart was the guest, and their conversation had gotten onto the topic of when Jon was young and “discovering himself”. He recounted how one day he was masturbating so vigorously that he thought he’d seriously hurt himself (“It looked like I wasn’t circumcised anymore.”); he freaked out and asked his mother to take him to the doctor.
Perhaps Leo, while uncomfortable, is counting his blessings (“At least I haven’t injured my penis.”). Mind you, I haven’t read the source material, so I’m just going by the out-of-context snippet.
I’m almost certain that was David Spade, though it’s possible they both told stories like that.