The Undelivered Spanking

Every male spanko, I’m sure, has a regret about the woman he should have spanked, but didn’t. J at The Orgy certainly does.

Seems that when he was a senior in high school, there was this hot sophomore girlfriend who cheated on him, and confessed. At that moment he held all the power cards in the relationship, and so he guilted her into giving him head to “punish” her.

But what he wishes he’d done is spanked her properly:

It was 1:00 in the morning when she finally finished telling me she’d cheated on me. Instead of both of us getting naked, though, and having oral sex, I now wish I’d done something different.

I wish I’d told her there was something I couldn’t do to repay her while we were in the house – during sex, she was good at keeping quiet, so even when she came, she didn’t wake anyone up. I wish I’d brought her out to my car and hidden us underneath the car cover.

I would have brought something with me. While cleaning out my parents’ garage a few months prior to my relationship, I found a couple of huge wooden paddles that went with a swimming-pool game I’d completely forgotten about. I purloined all four of them. I’ve spanked with them, and I’ve tested them on myself.

I would have brought one with me. Jennifer would’ve known what was going on, but she was so desperate to keep the relationship alive and well that she would’ve come with me. Trust me on this.

I would’ve had her take all her clothes off. I could never get enough of the fact that this beautiful woman wanted to be my girlfriend, and I loved seeing her naked. Then I would’ve had her lay across my lap as I sat in the middle of my backseat. I would’ve told her how upset I was. I would’ve chastised her for a few minutes.

Then I would’ve laid into her with the paddle. I would’ve smacked it into her ass over and over. The paddle itself is big enough to cover almost her entire ass, but I would’ve alternated cheeks. I would’ve told her this is what happens when she misbehaves. I would’ve told her I was upset, that cheating is wrong, and that I never would’ve cheated on her. (I didn’t, by the way. Ever.) I would’ve watched under the weak dome light as her ass grew pink, then bright red.

And I would’ve listened to her yelling that she was sorry, that she wouldn’t do it again. I would’ve held her in place with one hand, maybe wrapping my arm around her waist as I whacked her ass over and over.

I eventually would’ve stopped when I thought Jennifer had had enough. I would’ve gathered her up into my lap and held her and felt the heat of her ass even through the shorts I was wearing. I would’ve consoled her and comforted her and told her never to cheat on me again, and that I didn’t like to punish her.

Of course, that would’ve been a lie. I love giving spankings. Even when I’m punishing someone, I still enjoy doing it.

After Jennifer had calmed down, I think I would’ve tried to have sex with her. And I’m pretty sure she would’ve assented.

And I would’ve probably come quickly, feeling her scalded ass cheeks against my thighs.

Live and learn, J, live and learn….

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