Posted by: check868 | April 26, 2008

The “Good Boy”

Yesterday, I met a guy at my favorite bar. He was older, and he said he’d be wearing a blue suit. I was imaging something horrible, like a car salesman in a bright blue suit, but he was a distinguished looking gentleman in a suit so dark blue that I walked right by him because I thought it was black. And he was in his 50’s. At least.

I told him I was expecting something tackier when he described he’d be wearing a blue suit, and he looked offended. “I had lunch at the Four Seasons today!” he said, as though the tacky were not allowed through those sacred doors. Oh yeah, and this guy’s rich. He’s looking for a “relationship” (he’s married) where he buys me whatever I want. Theoretically. But we’ll get to that later.

We started talking about sports and he made a reference to the Giants making a deal with the devil. There was a pause, and I was like, “Did you ever see Damn Yankees?” His jaw dropped. “I thought you’d be too young to get that!” he exclaimed. (If you are too young to get it: it’s a musical from ye olde golden days of Broadway musicals about a baseball fan who sells his soul to the devil in exchange for his team winning the World Series. Hilarity ensues.) We talked about musicals, and he declared that if I wanted to go to any, he’d buy tickets for me and a friend to do so.

After a beer, he asked me to be his mistress, probably in all senses of the word, although I didn’t inquire. After two beers, I suggested we head back to my place. He readily agreed.

I sat in my lounging chair and told him to take off my shoes. He had never worn Converses before, obviously, and it took him a couple tries. “I have to go to the bathroom, and I’d like to go on you,” I told him when he had muddled through.

“Oh yes, oh thank you!” he said. He stripped out of his clothes and kneeled down on my kitchen floor.

“I’m not going to pee on you on my kitchen floor!” I said. “Get in the tub.”

I stood over him, and with two beers in me, it was easy. “Oh yeah baby, oh, you were saving that for me, weren’t you, baby? Oh, thank you, baby!” he whispered. I hate it when anyone other than my ex calls me baby, so I should have nipped that in the bud, but didn’t think to. When I was done, I leaned forward, just brushing his face with my pubic hairs, then leaning back as he tried to lick me and laughing at him. “Oh, I’ll be such a good boy! Next time, if I’m a good boy, will you let me drink it? I’ll be such a good boy!” I just laughed at him. He was so ridiculous, this old married lawyer sitting naked in my bathtub calling himself a “good boy.”

“Get up,” I told him. “I’m going to flog you.”

We showered off, and then I put on just a button-down shirt (I love that look: naked except for a button-down shirt) and took him into the bedroom. I took out my flogger and started wacking him with it as hard as I could. In part, I was being so rough because I was thinking about how annoying the guy who sits next to me at work is, and how much I would love to rip his buttocks to shreds. I was also thinking about how this was my Friday afternoon, my chance to relax, and I was spending it with this crusty old guy who kept calling me “baby.” Finally, I’m just a sadist and I liked the way he was yelping.

I stopped once in a while and felt how hot his butt cheeks were getting. “You’re barely pink,” I told him, cupping his ass in my hands. I started rubbing it, then rubbing his asshole. I got out my strapon and slipped it on. “Rub yourself,” I ordered him. I knew from personal experience it felt better that way. I slipped a lubed-up finger inside him and teased him, letting his sphincter relax. When he seemed relaxed, I pushed the head of my (fake) cock against his hole and continued to massage around the edges. He tensed up, but I didn’t push any farther, and after a couple seconds he relaxed again and pushed against it himself. I let it slide in very slowly, not pushing it in myself at all, just letting it go in a little bit when he pushed against it himself. I love receiving anal myself, so I know how important going slow is.

Once it was all the way in, I started thrusting against him. “Ah, you’re so big, you’re so big!” he kept moaning into the mattress. It felt nice, but I need to get one of those strapons with a vibrator in the base so I can get off, too. After a bit, I didn’t think he was going to come, so I slid out and he collapsed on the bed. I realized I had forgotten to put a condom on my strapon, so it now had little brown specks on it I would have to clean off. Lovely. I should have made the old perv lick it clean.

As he got dressed, he said, “So, this is the touchy part… I’d like to give you a little something… I don’t want you to feel under-appreciated, but I don’t want to give you false hopes, either. How much were you thinking?” I didn’t want to say… I mean, what if I said $500 and he was planning on giving me $1000?

“I don’t know… it’s hard… pricing myself… what were you thinking?” (the people I’m doing BDSM with don’t know I’m an escort).

“$200,” he said, as though he were Nelson Rockefeller.

Your lunch probably cost more than that, I thought bitterly.

He saw my expression. “What were you thinking?” he asked.

“I don’t know, more like, $500?”

“No,” he said, and that was that. What could I do, turn him upside down and shake him?

So, today I went and used his money to buy two-thirds of a corset. He kept going on about how he wanted to make my life easier and happier. Dude, $200 is okay, but it doesn’t buy jack shit in the city. He kept saying how he wanted me to get manicures and pedicures, he’d pay for it. At the place I like to go, a manicure/pedicure combo costs about $100. The corset he mostly funded was nice, though. The other third was money I got from the asshole foot fetishist last weekend, so when I wear it I will remember to be especially mean to cheap bastards and assholes.

Anyway, I’m going to tell him I bought 2/3rds of a corset with his gift, see what he says. I don’t like him much, so if this isn’t going to be more profitable, I’m probably not going to see him again.



  1. You’re awesome. 🙂

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