After a pretty nice Thursday at Oasis, I was ready to enjoy Friday to the fullest. I started the day with breakfast (with Spankees #1 and #4, as well as one from last TASSP and Oasis) and then a volunteer shift, helping to set things up for the early afternoon classes, and then it was time for a scene.

Spanking #4

Via the Oasis thread on Fetlife, I started corresponding with a guy who wanted to do a fairly heavy scene. He claimed to be a heavy bottom, and even though I warned him that doing a heavy scene on Friday might not be the best option he still wanted to go ahead with it. I resolved not to overdo it regardless — I can give a hard spanking without causing damage. He came to my room and we started a role-play scene in which I was a disciplinarian who had some sort of unspecified friendship/relationship with Spankee #4, and I’d caught him hiding four speeding tickets that he’d been collecting for six weeks. He was very good at wordplay, and actually made me laugh a couple of times, but we kept the scene going and eventually I got him to see the error of his ways and understand that he was going to be punished. We’d previously agreed on bare-bottom, so I sat down on the bed with my implements at hand, had him come over, and after pulling down his shorts and underwear I put him over my knee.

A side note — as I was doing that, he “warned” me that he had some “after-market equipment”. I had no idea he was trans* — it hadn’t come up in conversation. Ultimately it didn’t matter; he wasn’t the first trans* man I’ve spanked and he certainly won’t be the last. His equipment was held on by a harness, which we left in place.

I spanked him first with my hand, fairly hard, while lecturing him. I think he was surprised by how intense the scene was, even though I wasn’t going as hard as I could. Once he was warmed up, I switched to the hairbrush, and that was when things started to click for him. He was apologizing, saying he wouldn’t do it again, responding in all the right ways. Not that that changed things; he also got several swats with the wooden spoon.

I was planning to go longer, but I was getting a feeling that he was moving from “this is a fun punishment scene” to “this really hurts” and I didn’t want to push him too far. So I swapped out the spoon for a small wooden paddle about the size of my palm, and told him that, since he had four tickets and hid them for six weeks he would get ten swats, and he’d have to thank me for each one. These swats were the hardest yet, and he definitely got the message — while kicking and crying out quite loudly.

After the spanking, there were hugs, and then we ended the scene and talked for a while, going over how it had gone and what our thoughts were. I gave him some water, and we hugged again, and I saw him several times over the course of the party. I would say we’re, if not friends, definitely more than acquaintances at this point. and I’m sure we’ll play again.

Spankings #5 through #14

I spent the afternoon with my long-distance partner, and then it was time for Roleplay Roulette. At that event, the tops dress up as characters of their choosing (I went with my Squirrely Dan costume again, although I forgot the hat) and the bottoms choose who they want to be spanked by. They also fill out a bingo card with various costumes on it, and the first person to fill every square gets bragging rights. I gave ten spankings at the event.

• 5. Spankee #2 from Thursday sought me out. She was wearing a pretty accurate reproduction of a Rockford Peaches uniform from the original League of Their Own movie, and she got spanked over her panties while over my lap.
• 6. A gentleman that I met at TASSP was also at Oasis, and he was dressed as a jester. His bells didn’t really jingle when I spanked him (over his pants, over my lap), but it was fun regardless.
• 7. DD, who I’ve spanked at every party I’ve been to since TASSP 2022, was not wearing a costume, but I spanked her anyway, on the seat of her denim shorts.
• 8. DD and my long-distance partner are friends with an older gentleman from the west coast, and this time around he brought his regular spanking partner. She wasn’t wearing a costume either, but she still got spanked on the seat of her panties.
• 9. A friend from Atlanta, who I used to play with more frequently, attends a lot of spanking parties. She was dressed as a unicorn, and she requested a spanking, which I happily gave.
• 10. Next up was a friend from the Deep South who I met at Lone Star last year. She wasn’t in costume, but she had a magical dress that lifted right up out of the way when she bent over my lap, revealing some very revealing panties. So it was basically a bare-bottom spanking, although she wasn’t technically bare.
• 11. A gentleman dressed as a bicyclist went over my lap next. I think his bike shorts were a little padded, which to my mind defeats the purpose of getting spanked, but you do you.
• 12. A woman a little older than me (maybe in her fifties?) was dressed as a butterfly and she was up next. She told me she was floating a little bit afterward, which was very gratifying.
• 13. A professional spanker — who has acted in videos before — apparently was feeling like bottoming a bit. She requested a light spanking with her skirt up, and I obliged.
• 14. Finally, a woman I met at the surprise party on Thursday was dressed as Little Red Riding Hood. We talked, and I asked her if she wanted to be saked. Over the knee, skirt up, and away we went.

Spanking #15

I’d tried at TASSP to make plans with someone to do a flogging scene, but we weren’t able to link up. Fortunately, we were both coming to Oasis, and we continued our negotiations until we finally met at the vendor fair. Later that evening, we found some space in one of the hospitality suites. She ended up wearing only a thong, face-down on the bed, hair out of the way. There was a little spanking, but this was primarily going to be a flogging scene, focusing on her shoulders, back, bottom, and thighs. It went on for quite some time, working our way up in intensity until she was floating and shivering — which she assured me was completely normal, and didn’t mean that we had to stop. We did eventually stop, though, after… half an hour? Maybe 45 minutes? I wasn’t keeping track. It was a good scene, though.

Spanking #16

This was a short one and I hesitate to even include it, but it did happen. I was fiddling around with my dick stick — creating a conversation piece out of it — and a woman I was sitting near was interested in it, both from an aesthetic perspective as well as a “let’s see what that feels like” perspective. After a few test swats, I finally landed one really good one on her right outer upper thigh. She was quite pleased, and afterward I let her play with the stick like it was a magic wand.

Spanking #17

Back at TASSP, I met a woman who I actually first made the acquaintance of at TASSP 2022, when she bought one of my books. At the TASSP 2023 vendor fair, she declined to buy a new book because she hadn’t read the first one. Later that night, we chatted a bit, and before we played I made a deal with her: if she doesn’t read the book by TASSP 2024, I could bring her up on charges at Corporal Punishment Court. Well, she escaped that fate, because when we were talking at Oasis this year she told me she had read the book. She didn’t escape being spanked, though; I put her over my knee and spanked the seat of her panties with my hand for a good long while. I also gave her several licks with my tawse, which she enjoyed, before finishing with four swats from the scene-ender. She complimented me on my hand spanking abilities — which always feels nice to hear — and then we hugged and said good night.

And that was it for Friday. I rejoined my long-distance partner in our room and there was some… stuff… that happened before bed. It was, after all, our first anniversary, and she likes to repeat on anniversaries the things that we are celebrating. I was only too happy to do so.

Read more about Oasis 2023.