The Hershey Highway

My current favorite and I were getting started last night, and as we're lying there feeling each other up, she asks me "when are you going to stop being such a wuss and fuck me in the ass?"

We've had this conversation before, but she's never put it quite that way, instead just sort of hinting that she'd really like it, that it gives her a full feeling and other such stuff that I usually consider stripper shit.

As she makes this comment though, I can already feel myself shrinking, and since her hand is there, so can she. So I make the usual objections, and she's like "oh will you stop, it's not that bad. It's not like you're gonna be doing it bareback." I'm still not going for it, and so she goes to her bag and pulls out this dildo and some lube and asks me, since I like to watch her play with herself, to use *that* on her while she's doing it.

I agreed, making sure she understands that any...incidents will likely result in her not getting paid, as I won't be able to deal with that and probably won't even be able to keep it up. She just kind of rolled her eyes at that one, but said it wasn't going to be a problem.

I *do* like watching her (and most women, for that matter) playing with herself, and she's definitely a shower when it comes to orgasms