As part of the series of stories that eventually became “Bobbie’s Good Boy”, there was one where two people explored spanking and anal play. For the life of me I can’t find it anywhere; I was going to rewrite it and make it the next part of the Bobbie saga. I probably still will — it’s going to involve the main character’s first threesome when I do — but shortly after I finished “Bobbie’s Good Boy” I had the inspiration to write a sequel, “Bobbie’s Bad Boy”. The first part involves the main character being paddled for misbehavior. Here’s what happens next:

“Good boy,” she told me, looking appreciatively at my half-hard cock. Then she took hold of it with her lube-filled hand and started to stroke.

I got fully hard after that. “Very good boy,” she said.

I knew she didn’t want me to have an orgasm, because she wasn’t paying attention to my ass, but I tried to enjoy what she was doing anyway.

Once I was fully slick, Bobbie wiped her hand on one of our sex towels and then climbed onto me. She lowered herself onto my hard cock, settling her weight on my hips, and I whimpered; Bobbie was, as I’d said, a bigger woman, and my ass already hurt a lot. At least we didn’t have to use condoms; she had a birth control implant, and she’d taken me with her to the lab for us both to get STD tests, so there was nothing to worry about.

Bobbie began to rock gently on me, not really riding so much as easing herself back and forth. I knew she wouldn’t come from this, but I also knew she liked the feeling of being filled up with my cock — which still surprised me; I was only average, nothing special in that department. I guess, though, average is average for a reason.

I didn’t care all that much while I was inside her, though; she was smooth and slick — the lube helped — and she let out happy little moans as I hit her g-spot, which she’d pointed out to me early on in the relationship and said “I like when you touch me here.” For my part, I tried to ignore how much my ass hurt — I was sure it was bruised in at least two places, judging from the heat and pressure I felt — and just let Bobbie do what she wanted. She liked to be on top; she liked to be in control. And, for my part, I was happy to give up control to her. She liked me to be her good boy, to be submissive to her (I was learning the terminology when we had time to talk about it), and I had no problem with that.

After a while, Bobbie climbed off and laid on the bed next to me, face-down, legs apart. “You know what I want,” she said.

I did. It was something I’d literally never considered doing before, and something I hadn’t really even wanted to do at first. But Bobbie only asked for it after a shower, and I knew she was clean, and anyway once I got the courage to try it, I found that the pleasure she received far outweighed any discomfort I might have had.

In other words, I spread her open and fucked her ass with my tongue.