“What a pleasure,” I said. Natalie looked good, just a little bit tumbling out of her dress, the goods on display, but I was nervous.
This was a dating site date, and I had lost count of how many of them I’d been on recently. All the things women complained about were things that I, as a red-blooded American man, was experiencing from the ladies: Women lying about their age, women wanting to be pen-pals forever, women showing up looking way different from their pictures. Women carrying some industrial-strength baggage. There was ghosting and tears and women who used too many teeth during blowjobs. And then there was the one who never came back from the bathroom after what I thought was a friendly discussion about who we were voting for in November.
As I sat in the corner of the dim old-man bar (drinks were cheap and heavy on the alcohol content — only recently had the bartenders reluctantly stopped serving weapons-grade cocktails in jelly jars), my back to the wall so I could see what was coming, my expectations weren’t so high.
“Frank,” she said.
“I sure am,” I said.
She sat down close to me in the round booth and leaned over to give me an affectionate squeeze. I liked that. People who are physically affectionate put me at ease. I draped an arm around her, pulling her close, and said, “Now that is a dress.” “Oh, this old thing?” she said, beginning a quote from my favorite old movie, “I only wear this when I don’t care how I look.” I laughed. “I was a little nervous, I have to admit,” I said. “But I think we’re gonna be fine.”
We ordered drinks and a plate of fries to absorb them. The waitress looked like she was on our side. Natalie never quite stopped pressing her thigh to mine, and we ate and talked that way, with her occasionally stroking my arm or leaning in to press her breasts against me, or me lazily playing with the hem of her dress, inching it ever up her smooth, taut leg. It was one of those dates that just felt comfortable from the get-go, and I wondered how this was different, both more erotic and more wholesome, from dates where I’d find myself balls deep in someone and still feel no connection.
“I could feel the fine, fine razor stubble of her mons. She’d shaved it, but not today.”
The only red flag was the occasional hiccup between the data in our texts and emails and what popped up in conversation. “Oh, for some reason I thought you were from Philly,” I’d say (turns out she was from Jersey), or “I could have sworn you said you were Irish,” she’d say (I’m German). To be honest, I’d been on so many first dates that all those profile questions and drink orders were blending together like all the margaritas I was buying.
The important thing was that we were hitting it off in person and the only tension either of us was feeling, three or four drinks in, was how we’d keep the night from ending at the bar. Somebody had to make a move, and I just couldn’t bring myself to say something cheesy, like: “So, do you want to get out of here?”
But she was on it. She had these long curls resting pertly atop her cleavage and I said, “Bedhead must be a problem for you,” to which she very sweetly replied, “You’d better mess up my hair.”
“OK, let’s go,” I said. She got up quickly, I left a hundred on the table for what was probably a $70 tab, we got in my car, and she languidly brushed my growing cock through my pants throughout the short — and increasingly treacherous — ride to my place.
Once inside my apartment she lifted her arms like she was at the top of a roller coaster. In a split-second I knew this was so I could pull her cheap dress over her head, which I did. I reached around to grab her naked ass (because of course she wasn’t wearing panties) and slam her closer to me. She was at my belt with small, practiced hands, knowing that she needed to lift my pants up and over my towering erection before she pulled them down again.
I mean, you’re always going to love your first high school girlfriend, right? But give me a woman who knows how to remove a guy’s pants without breaking off his dick or zippering him to unconsciousness every fucking time.
After a brief fumble with our clothes I carried her — quite gracefully considering the circumstances — to the bedroom and dumped a sprawled hot pile of Natalie on the bedspread. I had to get at her and so I buried my head in her puffy pussy lips until I felt I couldn’t breathe, holding onto her fantastic tits as I did so, like I was drowning. She grabbed my head and pressed it farther into her vulva. I could feel the fine, fine razor stubble of her mons. She’d shaved it, but not today. She wasn’t expecting tonight’s date to lead to my place. That made me feel great, and I ate her ‘til she came, her thighs crushing my ears. Then my lips and my cock followed each other up her body. I kissed her, feeling her mouth respond to the taste of her own juices, and eased my cock into her waiting pussy. She gasped.
“I’ve got a condom on, Natalie,” I said.
“Fuck me, Frank!” she said. “Fuuuuuck meeeeee…”
And I did. I fucked her until I felt her body tensing, or my body tensing, and then I’d stop. I’d think about the NBA draft, which gave me a buffer of about 15 seconds, then I’d start fucking her again. When I couldn’t take it any longer I got to my knees, raised her ass, threw her ankles over my shoulders, and long-dicked her until I shot my load deep into the whirling recesses of her orgasm.
What seemed like minutes later, forehead to forehead, we had to ask.
“So you’re not Natalie?” I said.
“No, I’m Jessica,” she said. “Jessica from Tenafly. And why did you say your name was Frank?” she said.
“I thought you said I was ‘frank’ because you caught me staring down your dress,” I said. “My name is Kevin. Jessica, I’m Kevin. Would you like to go on a date?”
“Yes,” she said. “You can see how my bedhead looks tomorrow at breakfast.”
Wherever Natalie and Frank are, I hope they had a good time.