I reached around him to stroke his cock, which was already beginning to regain its firmness.I stopped for a moment to get the KY gel I had in my toile... bag, (I have this because I like to finger myself when I masturbate). I took the tube and poured some gel into my hand. I rubbed as much as I could onto his ring and then probed my finger inside him. Josh welcomed my finger into his rectum with a loud groan.I explored his anal cavity with my finger for a minute or so. I then smeared my precum. ”I hesitated several minutes going back and forth over doing it or not but that cash won out over my fear of any pain.“Give me the money and there are rules.”“Sure man, anything you say.”I took the cash from him jamming it in the right front pocket of my jeans.“Rule one: if it hurts to much the deal is off and you get your money back. Rule two: if I tell you to pull out and you don’t get it out fast enough you lose your money. Rule three: don’t forget rules one and two. Got it?”“Yeah, I got. When Rose went to junior high school, I thought she’d probably follow in her sister’s footsteps. Both girls were overly endowed. I blame the hormones in chicken breasts. I assumed I’d be struggling to keep her home before she reached eighth grade.But she fell in with a crowd that took life seriously. Not that there was never any questionable activity, but by ninth grade they had solidified into a unit. They even created an agreement to govern their dating. I was impressed. It was the first sign. Actually, it's more me having to control the urge to impale myself. Shallow sex is sloppy, it all seems to run out. Better to plant the seed deep. Heck, did enough of that too!Enough that I'm quite tender and a bit raw at present. I guess there is no getting used to that tennis ball sized cockhead. I'll take it while I still can.Stacy turned out to be an out of control cock hound. I got a report she spent the 2 days after the wedding with Osei and Kristen. I need to get on the phone.