The following piece was presented at Jersey City Writers’ literary event – 800 Dirty Words. Please enjoy.
Wall St. Guy wasted no time sharing his perverse predilection. On the phone, planning date #2, he plowed right in with how much he wanted to have sex with me, anal sex, to be exact.
He expounded on the physical pleasure of feeling his cock stimulating all the nerve endings around my asshole, and how the orgasm from his derriere dalliance would take me to the moon and back. It would be a mistake, he insisted, to not partake of such pleasure between the two of us. And, if it was going to be my first time playing in the mud, I didn’t have to worry because he promised to be extraordinarily gentle.
I was not surprised at his desire to partake in some uphill gardening. He had hinted that his tastes were “exotic and erotic”, and that he usually got just what he wanted, no matter the cost. In fact, his online dating profile described him as, “a mega-successful stockbroker, able and willing to spend on decadent delights.”
I listened politely until he finished his posterior pitch. Then I enthusiastically said, “Yes, let’s do it!”
“What?” That’s great!”
“Yes, let’s do it,” I reiterated. “How many inches can you take?”
“How many inches can you take, and should the dildo be smooth, ribbed, or would you prefer to be pegged some other way?”
“That’s not what I meant,” he growled. “I meant you’d take it in the ass, not me.”
“Well, I wouldn’t want you to miss out on the physical pleasure of feeling a big cock stimulating all the nerves around your asshole, and an orgasm that takes you to the moon and back. It would be a mistake to not partake of such pleasure between the two of us, and I’ll be extraordinarily gentle, so you don’t have to worry if it’s your first time.” I’m glad Wall Street Guy couldn’t see the devilish smirk on my face.
“Are you kidding me?” I’ve done this to women; not the other way around. And it was great! That’s how it’s supposed to be. Would you even know what to do?”
“Well, I’m sure I could find a video online to learn exactly what to do to make your first time awesome. No big deal.”
“Are you afraid? Is that it? I promise, I won’t hurt you,” he said in a tone that was conciliatory and slimy.
“No, I just don’t want to,” I retorted. “What happened to regular sex, if only to see if we like each other enough to get kinky?”
He continued in a sleazy purr, “Well, we’re not like everybody else, so why should our sex play be like everybody else’s?”
I thought a moment, and then said, “OK, you’re right, we’re not like everybody else. So, it’ll cost you $1500.
“What?” $1500? Why should I pay you?”
“Well, you said you make it rain whenever you can’t get something that you really want, so if you really want to ravish my ring, open your umbrella, ‘cuz it’s gonna cost you.”
I had listened closely to his stories of using money to get whatever he wanted, and now the student had become the teacher. Negotiations were in play, and I intended to win.
Wall Street Guy must have been stunned, because he backed down. “Maybe you’re right,” he conceded. “Maybe I’m going too fast. I just thought that you’d be DTF on this. Your lovely booty deserves special attention, and I’ll have that puckered little rosebud at some point, I’m sure. But the next time we’re together, we’ll talk about fucking in general, not just about tagging your tush right away. Maybe we’ll start by me eating your pretty pussy. How about that, Baby?”
I was both irritated and amused. Cocky bastard. “Sure, OK. Let’s save our talk about fucking fun for another time. Sweet dreams, Honey.”
The next few times we got together, we did talk about sex. We talked about it so much that it just didn’t sound fun anymore. And Wall Street Guy wasn’t budging on buggery. He still wanted a free key to my back door.
Negotiations eventually reached a stalemate. Although Wall Street Guy couldn’t get in a posterior poke, he did get in a verbal one. “I thought you’d be fun, but you’re just unreasonable. I need someone who’s down for getting down, not a Debbie Downer.”
Then, we stopped dating, which was fine by me. It was time to leave him behind anyways, so to speak.
Since Wall Street Guy, the “no entry” sign on my rear has been a deal breaker with three other men. I will never understand the beguiling call of my backside, since I’m 5’4” and 116 pounds, and my ass is by no means Badonkadonk. It’s more of a Badonkadon’t.