Whore Diaries, round two

Man fucks woman; subject verb object. – Catherine MacKinnon

He stands before me, muscled and tattoo’d, in worn leather work boots and dirty jeans.  He just paid me four hundred dollars to be mean to him and shove things up his ass. I just told him to undress. And he is stalling at the pants.

Thwap, I slap my new leather and fleece paddle against my hand. It’s nice. It has a sturdy character, and soft fuzzy stuff on it.

He jumps and shrugs, looks up at me. “This is the embarrassing part.”

I shrug like I don’t give a shit about his embarrasment, but I wonder what it is. Small dick? Something kinky? Or some kind of disfigurement? Once a man in a wheelchair wanted me to make fun of him for not being able to walk and I couldn’t do it. 

He is bright red when he finally drops his pants to reveal pretty pink latex and lace panties bulging out around something huge.

Staring at him with his tattoos and muscles and dirty jeans down around his ankles, blushing down at his lacey pink panties, I think I have arrived. I’m not sure where, but I’ve definitely arrived somewhere.

I laugh. I know all about sissy boys. The other day I told someone I am a hundred years old in stripper years. Practically translated that means that I’ve encountered every possible fetish, and even if it is different unclothed, it’s not that different.

“Awww, what a cute little slut,” I tell him, pulling his panties out a little to peek in. It’s all cock, shoved into a huge steel cock ring, which makes me really glad I’m not the kind of whore who would be stuck trying to fit that monster in my vagina.

I dress him up in some stripper clothes and make him parade around while I make fun of him. He loves it. How does this happen?

When he’s as humiliated as I’m going to make him, I have him kneel and cuff his hands behind his back with the new leather cuffs that vibe review sent me. I’m suprised by how nice and sturdy they are – there’s always the potential, in those mainstream kits, for cheap flimsy stuff – but these are nice.

There was a little whip in the kit, and I brush it gently all over his body, occasionally swatting at him with it. I make my breath match his breath – I learned it from energy psychology, but it works great for sex work, too. Now I can feel his feelings and mine. He quivers when I run the whip up his skin, trace a tattoo with it, and humps the air spontaneosly when I fwap his penis with it.

Finally, when I think he’s about to explode, I bend him over the bed and stand behind him with my strap on. He works himself onto it quickly, and I stand still while he fucks himself on it. My legs are a little spread for stability, my hips tilted so the strap on rubs my clit every time he pushes into it, and looking down I think this must be what it’s like to be a man. To look down and see some slut underneath you, to be the subject to her object.

Weird.

When he’s about to come again, I step back and cuff him to the bed posts. I climb on top, woman fucks man, and shove an even bigger cock into him. He moans and writhes and gasps in ecstasy, and right before he comes I pull out, shove the stubby g up his ass on full vibration, and grab his cock to give it a few pumps.

He explodes into a huge orgasm that leaves him giggling for ten minutes.

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