TASSP: I spanked a boy and I liked it

…but if he was wearing cherry Chapstick, I didn’t find out. And he wasn’t a boy; he was definitely a man.

At TASSP, one of the events I definitely wanted to attend was the male/male party, for various reasons. First of all, I love spanking. But more importantly, I wanted to experience spanking from and to a man, so I could be more accurate in my writing of male/male scenes.

The party wasn’t heavily attended, I think because (a) most of the men at TASSP were strictly heterosexual, be they bottoms or tops, and (b) men are more heavily socialized, at least in the US, to not want to explore things with other men (whereas women have a much easier time of it). When I got there, two scenes were going on, and I started talking to an older gentleman. Eventually most of us ended up in one of the side rooms, just chatting, and one man was basically instigating the entire discussion. However, no spanking was happening, so finally he said something to the effect of: “I’m going in the other room to check on something, so you all figure out why you’re here.”

When he came back, I told him why I was there, and we went into the other side room to negotiate and play. We decided to start with him bottoming.

Sidebar: this gentleman went by Sabina. He sometimes cross-dresses at parties, and at this event he was wearing a fancy dress, corset, panties, and stockings (when dressed in men’s clothing, he goes by a different name). We did discuss pronouns, and I have to admit I was still a little confused when we finished that part of the discussion, so if you’re reading this: I apologize for any misused pronouns.

Due to Sabina’s height, we decided to have him laying down over some pillows. I lifted the dress and began spanking through both the corset and panties. I had to go harder than I might normally to make it through both layers of fabric, and remember by this point I was dealing with the aftereffects of spanking two iron butts (one of them only six hours prior) as well as giving an extremely hard hand spanking less than an hour prior. So it wasn’t long before I switched from my hand to a boudoir paddle (very similar to this one).

Sabina liked being spanked hard, so I did that. The paddle was loud, and I whacked not as hard as I could but pretty darn hard, and I got plenty of good feedback… including the fact that Sabina was getting turned on. We discussed that briefly — not that it was happening (which I was totally fine with), but that he had spent many years divorcing sexual arousal from spanking. In other words, not getting hard during spankings. But whatever I was doing — whether it was how I spanked, or the fact that it was a new experience, or that maybe he was attracted to me and wasn’t expecting it — I had broken down the barrier between spanking and sex and he was quite aroused.

While I spanked him, I told him to go ahead and feel what he needed to feel, to be aroused, to enjoy it, and he was making a lot of very encouraging motions and noises. It was honestly pretty hot that I could do this to a man on my first try.

After a while, I had to stand up (I was kneeling on the bed, and my hamstrings were starting to hurt a little), so I switched to the hurling stick. It’s longer, so there was also the leverage aspect of the swings, and I know it was hurting him, but in a good way. We continued for a while, until I realized it was getting close to eleven and not only did I have plans for 11:30ish (with Clarine) but I also still wanted to get spanked.

We wrapped up the scene, and hugged, and talked a little bit about how we were both feeling. I said that I was also interested in bottoming, but he was so spacy from the scene that he felt it would be unsafe for him to top me, which I completely respected. Unfortunately, by the time we were done, there was no one else in the suite, so I didn’t get spanked. It’s okay, though, because I did gain a new experience, and I met a very nice person who I would be more than happy to play with again.

I’ll admit that one of my concerns about male/male spanking was that I’d have some sort of irrational “hump” to get over, but there was no such thing. That suggests to me that if I have the opportunity to spank a man in the future, I won’t have any issues doing so.

Overall, a very good experience.

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