Confession by Miss Vixie

A recent RL encounter (true story):
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I'm at a local dungeon at a women's-only party. I've already had one play date when Caitlyn comes outside where I am, to have a cigarette. That's what I'm doing. The sweat is still on my breasts from spanking and flogging Carrie. I'm naked from the waist up.

Eventually I ask Caitlyn if she'd like to play, and we negotiate the scene. It's obvious from our talk that she's something of a pain slut. This looks like fun.

I lead her inside to a spanking horse. She strips down to her panties and takes her place. As I carefully tie her in place, I wonder if I'll get to remove those panties later.

Her breasts are small, too small to permit extensive clothespin play, but I start off by putting a couple gentle clothespins on her nipples. I tell her it's up to her when I remove them. She's skinny as a rail, but with a nice little ass.

After a few experimental spanks, I get out my deerskin flogger. I start going at her lightly for a couple minutes.

"How's that, dear?" I ask. She wants more, and harder. I oblige.

On it goes, with me checking on her every couple minutes and her asking for more, and harder, each time. I continue to oblige her. Eventually I'm flogging her harder than I've ever flogged anyone, and she wants more. And harder. Finally she's satisfied with the pain level. Oh, my!

That ass is starting to get nicely red, I noticed. I've worked up quite a sweat with the flogging and I need to switch tactics to conserve energy. So I go to spanking.

It's actually easier to apply serious pain by spanking than with a deerskin flogger, so this is something of a rest break for me. But I know I won't be able to keep it up for long. So I switch strategies after maybe ten minutes of the spanking.

"Would you like to cum, dear?" I asked her. "Yes, please, mistress."

"Good girl", I say. "And, mistress?" she asks. "Yes?"

"May I have some pain with my orgasm?"

I think I can manage that.

I don latex exam gloves. She's too young to have an allergy, really, but I ask anyhow. She denies it. I slooooowly pull down her panties.

I get out the lube (I always have a tube in my kit) and start to gently lube her up, starting at the clit and working gently inside. Soon I have two fingers inside her, then three, then four. "Fuck my hand, dear" I tell her needlessly. She's already doing it.

I wouldn't care to say how many times she came, but it must have been two or three times at least. I keep her suspended in ecstasy for ten or so minutes, then finally I must quit. My back is starting to hurt from the position I'm in. I untie her and she dresses, smiling at me as she does. We head outside for another cigarette.

She's half my age, so I'm not considering her for a relationship or anything. Turns out it's a good thing I didn't get attached, as she moved to San Francisco from here (Los Angeles) a week later. We're still friends on Fetlife, though.