Chronicle of a date foretold

It had been a month since our last (our first) date.

She got to restaurant first, wearing the outfit she’d bought – that day – to go with lingerie I had bought, sent her, for this very purpose, just a couple of weeks ago. She wore a black skirt, long-ish, but with a really high slit, that converted a conservative length into a radical, daring even, reveal. Similarly, the floral top, long-sleeved, that she had bought looked at first blush like something one might wear to the office, but it tied itself shut (or she had tied it shut) at the base of her cleavage, leaving much of the bra I had bought her visible. Tantalizingly. Fabulously.

When I wrote an outline of the evening, to facilitate my writing of this post, I wrote, “She looked a bit slutty, revealing – high slit skirt, tied, open cleavage top, bra showing.” When I shared that outline with Charlotte, she asked, “I looked slutty?” She didn’t like reading that, I gathered.

The truth is, she didn’t look slutty. She looked… confident, hot, like a woman who was going to have sex shortly. “Slutty” makes some assertion about the number and quality of partners, the discrimination of the person described. Her outfit was anything but cheap, anything but non-discriminating. No, she didn’t look slutty – that shorthand, intended to remind me of how she looked, worked fine for the purpose I was using it, but not at all to describe how she actually looked. How Charlotte looked was… determined, ready, and not as if she was seeking attention, but rather, as if she was providing herself to an intended audience. Very different. Not slutty.

This is the bra I had bought her:

It doesn’t read to me as slutty. It reads, to me, as fucking hot, and, on her, it was.

I walked up behind her – she was sitting at the corner of the bar at which I’d instructed her to arrive a bit before me. I wanted her waiting. I wanted her anxious, eager. As I sat down next to her, kissed her, said, “You look good,” she put her phone down. She had been scrolling through, I think, the current Instagram equivalent of TikTok videos – whatever Facebook calls that. She was sipping a rose, I think. She had ordered me the Oban (one ice cube) I’d requested, and it sat, waiting for me.

The restaurant/bar I’d selected was softly lit, French-feeling. It’s a nice place, and the bar is cozy, small. Perched at its corner, we had some privacy, but only a little.

First things first: let’s try to connect the app on my phone to the remote-control vibrator she was wearing. At first, it seemed like it was working. But then, as it had the first time we’d tried this, it started cutting out. And, in any event, the vibrations provided by this vibrator do very little for Charlotte. “It’s relaxing,” she said, “but not very intense.”

I paused to take in Charlotte’s pretty, pretty face. I had not remembered just how clear, bright, radiant her skin is. Or, how hungry, how penetrating, how open, how pretty, her eyes are. Damn, I thought. We’re gonna have fun.

But back to the vibrator: no matter what I did with the controls, I couldn’t provoke much response in super-responsive Charlotte. It was only a few minutes after we had moved to a table, with more privacy, that Charlotte asked for permission to remove the vibrator from her panties.

Permission granted, she disappeared to the ladies’ room for a moment, and then returned. Her phone she had left on the table, which prevented me from instructing her further while she was in the ladies’ room. “You left your phone here,” I said. “Please go back to the bathroom, and take it with you this time.”

Off she went. Surely, she knew what was coming.

“Take your panties off. Bring them to me. Hand them to me. Please.” I wrote.

These were the matching panties she was wearing, briefly:

Charlotte generally doesn’t wear panties. She does, for me. She was surprised to notice how… exposed… she felt having simply returned herself to her more typical state. “Well yeah,” I said. “Obstacles are hot! Removing them is hotter!”

I palmed the panties, sniffed them – her scent was strong but subtle, sweet. I felt how wet her panties were. Now, my hand smelled of her cunt, too.

I ordered for us: oysters on the half shell, shrimp cocktail, and escargots. (She had never eaten escargots before.) I told a dad joke – one made famous in “Trading Places,” but which I knew from long before even that.

As we ate, we played a game I love: we invented stories about the other diners nearby. There was a foursome – three men, one woman. Was the woman dating the guy to her left? Charlotte imagined she certainly liked him, as she was laughing at nearly everything he said. I imagined that the guy to her right was a “gay-for-pay” pornstar, that she was his girlfriend, and that maybe, just maybe, he was a bit more “gay” than “for-pay.” There was a threesome – three women, two in their 40s, one in her 20s. The older ones looked not unlike the Indigo Girls.

And there was another threesome – three women, all attractive, all very different. One was very MILF-y. One, very trashy, with obvious lip implants. And one, wholesome hot. We agreed they were Instagram influencers, each with a different audience, brought together by a publicist. Or maybe the two blondes were mother daughter, from Idaho, Mormon, and the brunette with the lips was a friend of the daughters.

Then, we flipped the script on the game. “What do they think our story is?” Charlotte didn’t miss a beat. “I’m an escort, obviously,” she said.

“I’m not sure,” I said. “I think that I have a teenaged daughter. Maybe 16, maybe 17. You are her math teacher. We met in the spring at parent-teacher conferences. There was chemistry, but also, propriety. We weren’t going to go out until after my daughter had graduated. And here it is, August, and the math teacher had been away for the bulk of the summer, trekking. In Myanmar.

A brief segue about Las Vegas, which, a former colleague of mine once, said, “has the highest population of nieces of any city in the U.S.” (Charlotte is much younger than me. A violation, even, of the half-your-age-plus-seven rule.)

The food gone, Charlotte wasn’t yet ready to go to the hotel room I had reserved. “It’s early!” she said. And, “I need to drink a bit more.” Charlotte didn’t want to drink alone. We each ordered a second drink.

That second drink crawled by. And finally, finally, we were on our way to the hotel – a 5-minute cab ride.

The hotel was not fancy. It was kind of skeevy, truth be told. But they checked us in, as I lifted Charlotte’s skirt and slid my fingers down her ass-crack, just flicking against her dripping wet pussy. The check-in complete, we got in the elevator, headed to the 6th floor. Finally, finally, we kissed, my hand gripping Charlotte’s throat, pressing her, hard, against the wall of the elevator.

Once in the room, we kissed a bit more. Then, I turned Charlotte around, asked her to lift her hands up against the door, over her shoulders, to step a step or three back from the door, exposing her pretty, round, big ass to me.

I lifted up the skirt (or maybe I had had her remove it – I don’t recall), and I commenced spanking. For a bit, I focused on the right cheek. “Are you doing ok?” I asked. “Please, tell me, tell me, when you need me to stop. Use ‘red,'” I said. For every three or four slaps of her right cheek, I gave her left cheek one. I snaked my left hand down her belly, pressed a finger against her clit, into her cunt, as I spanked. Her ass was growing warm to the touch. Soon, she said, “I need you to stop. I’m done. Red, on that cheek, please.”

The 3 or 4:1 ratio now was ended, and 100 percent of my force was devoted to her left cheek. That did not last long. “RED!” she said.

At this point, I decided it was time for her to make my cock hard a different way. “Play with yourself,” I said. “I haven’t heard, seen, you edge nearly enough in the lead-up to tonight. You’re going to work yourself up now,” I said. She said something about how she can touch herself when she’s alone – why does she need to do that with me.

“Duh,” I said. Or thought. “Because I’M WATCHING NOW!”

There’s something about watching Charlotte’s pleasure that makes my cock especially hard. My cock was hard for hours this evening, but never was it harder than when Charlotte was touching herself for me.

In time, I pulled a pillowcase from a pillow, and tossed the pillow on the floor in front of me. “Kneel, please.” I stepped back. Removed my shirt – a flecked green polo shirt of the softest cotton. I removed my pants – burgundy jeans I haven’t been able to wear in years, but which fit once again. I stepped out of my black cotton boxer briefs. And I pressed my cock into Charlotte’s mouth.

Damn. Charlotte’s mouth, clearly, is where my cock belongs. Soft, moist, warm. Eager. Hungry. Compliant. She played with my balls, she licked, she sucked. I stepped back again, removing my cock from her mouth, and went to my bag. I pulled out some of the rope I had bought. I’d never actually used rope before. I had used restraints of various sorts, but never rope. Some time earlier, though, I’d seen a video, and it had inspired me to fantasize a bit about this evening – a fantasy that required rope. And a magic wand. Which I had procured.

So out came the rope, and I did a passable job of tying Charlotte’s wrists together behind her back. “This is much better than handcuffs,” I thought. Somehow, there’s something both gentler and firmer about the restraint rope, well tied, provides.

Her wrists secured, I resumed fucking Charlotte’s face. Not too hard – I’m just not a violent face-fucker, 99 percent of the time. But I did fuck her face, at length.

“Are your knees hurting you?” I asked at some point.

She nodded. “Yes,” she said. “This is uncomfortable.”

“Good,” I said. “I like that you’re enduring a bit of discomfort in order to give me pleasure.”

And that’s true. But it’s also true that at the end of the day, what I really liked wasn’t that she was enduring discomfort. It’s that she was prepared to endure discomfort, willing to endure discomfort. I don’t actually take pleasure in the discomfort itself.

So, soon, I had her get up, and tossed her on the bed. I had to untie her hands so that I could retie them, this time, over her head, and looped around the pillow. I affixed her ankles to her thighs, as in that video to which I linked in my previous imagining of the date. I knew that Charlotte wanted – more than anything – to feel my mouth on her cunt again. It seems she had very much enjoyed that in our previous evening together. And so I granted her at least a tiny bit of that sensation. But no more.

And then, I got the wand….

[end of part 1]

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