A night on the town with Charlotte (part 1)

As (it seems) is usual, Charlotte arrived first.

I had selected a restaurant that was, literally, a 30-second walk from her apartment. (Not that we were going to her apartment. I had arranged a hotel room for us.) I had eaten there before a few times, most recently, about three months ago with the doe-eyed beauty and another gentleman we know. Our food had been delicious, and the combination of quality and convenience (for Charlotte) was dispositive.

Charlotte texted to ask if she should be early or on time. (I fucking love that question.) I told her to arrive on time, that I expected to be on time, and that we had a reservation. Under my (real) name. When it became clear I would be about five minutes late, I texted: “I’ll be five or so late. If they seat you, please order me a Johnnie Walker Black on the rocks.”

I arrived to find Charlotte sandwiched between two other two-tops. On her right, a non-descript couple that I barely remember, to be replaced soon enough by two attractive 30- or 40-something women. And on her left, a… couple? I wasn’t sure. The woman, sitting on Charlotte’s side, was attractive, and, I would guess, in her late 30s or early 40s. She actually bore a striking resemblance to a woman I had worked with about 30 years ago, which confused me a bit; she looked a bit like this other woman might have looked 10 or 15 years ago. This woman was talking with a man, less attractive, in his… early 20s? I couldn’t read their relationship well, but they were talking a lot about California generally, and about crimes against Asians in California.

Charlotte was fucking hot. She wore black tights, a green dress, and had on the back of her chair, a coat that, later in the evening, she said made her feel like a hooker. I asked her if she liked feeling like a hooker. “NO!?!” she said. “So why do you wear a hooker coat?” I asked. Which she took as confirmation that I thought it looked like a hooker coat. (I didn’t.)


Under the hooker coat, she wore black tights, black panties, a black bra, and a shimmering, short green satin-y dress. Her hair, as ever, straight and shiny. Her nails painted black. Her lips bright red against her pale face. Her teeth toothpaste-model straight and white.

I had one scotch, and she had two glasses of wine and was put out that I didn’t have another scotch. She doesn’t like “drinking alone.”

“You’re not alone!” I said. “I’m right here.” And, I showed her the THC tincture I had placed beneath my tongue just a while earlier. And… later I had more scotches.

“You did a lot of preparation for tonight!” Charlotte said. I had told her that I was preparing, twice, with about thirty minutes apart, earlier in the day.

“Yes!” I said. “I was making this envelope….” I showed her a standard white envelope, filled with fortune-cookie-fortune sized (or slightly longer) pieces of paper.

“What’s in that?!?” Charlotte asked.

“You’ll see….”

After oysters on the half shell, shrimp cocktail, and four delicious scallops – all of which we shared – we stepped out into the cold and took a cab to the hotel I had booked – a five-minute ride. We checked in. The customer service rep told me that I have “the best name ever.” Which, actually, is true. And which, actually, I’m told not infrequently by anyone who sees it for the first time. And is in customer service or retail or marketing.

“How many keys would you like?” he asked.

“Two,” I said.

I handed Charlotte the key to room 509. “Head upstairs, please. Come for me. Twice. And then text me.”

“Do you want me to record myself?” she asked.

“Of course!” I said. “And send them to me.”

I wondered how many orgasms Charlotte has had beyond my auditory experience in recent months. It can’t be many.

My phone buzzed in five minutes or less. “Thank you!” I wrote. “I’m listening now…. Please stand, facing the hindow, hands up high, legs spread wide. I’ll be there soon enough.”

“Okay,” she replied.

I pressed “play” on the audio that had just arrived in WhatsApp.

Charlotte’s breathing, and moans, started to come out of the speaker. I held my phone up to my head, hoping to switch the audio from the speaker-phone to the more private speaker dedicated to my ear alone. But that’s never worked well for me with WhatsApp audio. I don’t know if I am alone in this experience, but whenever I press the phone to my head while listening to a WhatsApp audio/voice message, it just stops. So I pressed “play” again, and held the phone in front of me. In the hotel lobby. As I walked to the elevator.

No one was that close to me. And the volume was pretty low. But. Charlotte’s wasn’t.

As I stepped into the elevator, Charlotte reached her first crescendo. I waved my key over the elevator panel and pressed “5.” And Charlotte had begun approaching her second orgasm by the time the elevator doors closed. When they opened, and 509 was right across the hall from the elevator, I turned up the volume on my phone, opened the door, and stepped inside to find Charlotte posed as directed.

The excellent view on arrival

I reached around the front of the dress, pinching a nipple. Hard. I reached between her legs and pressed a hand up against her (warm, wet) cunt. I could feel both through her tights. I lifted her dress to give me a better view of her pretty ass.

Charlottes ass

And as I took my first orgasm from her with my hand, through those tights, I gripped her neck tightly with my other hand and turned her face to me, and kissed her. Hard.

I took another orgasm or two from her with my hands by that window, turned her around, and tossed her back on the bed by her throat. And grabbed the wand I had asked her to bring.

Before I lowered the wand on her cunt, this is the view I was fortunate enough to enjoy:

Charlotte decided not to share this And I respect her wishes But its your loss

[Editor’s note: when I reached this point in my writing/editing, I asked Charlotte to come for me. Right now. And she did. Enjoy!]

I did lower the wand, though, on her cunt, and held it there until I elicited my first of several “red” utterances from Charlotte. [I remember Veronique once telling me that I was “misusing” the safeword concept, that “red” ought to bring a scene to a close, not simply a pause. And in many other contexts, with many other partners, that might be true. But that’s not how I use safewords. And it’s not how my “scenes” go. If a partner of mine were to say, “We need to stop, seriously,” that would be enough. I wouldn’t need a safeword. Because once “red” has been uttered, we’re in a wholly different conversational space. Veronique practiced a more defined, more broadly shared, version of BDSM/safewords – and probably a safer one, for those whose scenes are more extreme. But for me, my system seems to work fine. And I’ve never had a misunderstanding.

In any event: after a bit, I sat myself down in an armchair, and instructed Charlotte to walk to the front door of the hotel room, to get down on her hands and knees, and to crawl to me.

We had discussed crawling (and collars, and leashes) in the context of a discussion of a sex party we plan to attend in a few weeks. Charlotte has a bit of an ambivalent relationship to crawling for me: on the one hand, she appreciates and enjoys the theatricality, the submission. On the other? She just. Thinks. It’s. Funny.

So as she crawled to me, she giggled.

[Side note: why don’t hotels that aren’t hot-sheets places have a “sex lighting” option? The lighting is just always so hard to get right.]

When she reached me, I had her (try to) remove my belt (she needed help), and start to tease my cock through my thighs. She kneeled in front of me, I eased my cock (hard) out of my black boxer briefs and jeans, and she lowered her wet mouth onto me. “JESUS!” I moaned. “Every man whose cock you ever suck from now on should send me a thank-you note. You were fucking awesome at this when I met you, and you’re 100x better now!”

And she is.

Charlotte worked my cock for ten, maybe fifteen minutes, before I brought out the envelope with which I had teased her earlier. “Pull one out,” I instructed her.

The first she pulled, as I recall, read, “You love sucking cock, and it’s been a year since you did, because you were in an all-female environment (school?).”

She laughed.

Over the course of the evening, Charlotte sucked my cock a lot, and, periodically, either she or I would pull out, and read, a new instruction:

You are a nun, being forced to suck a priest’s cock. But you believe deeply in the sinfulness of what you’re doing.

You are a nun, deeply enamored of the priest whose cock you are sucking, and whose cock, you imagine, will bring salvation.

You want, desperately, to be able to reach orgasm JUST by sucking my cock.

You are my boss, taking something you want from me, because you can. [She took my hat, reading this instruction completely differently than I’d intended.]

You’re competing in a contest to see who can suck a cock (my cock) the longest.

You’re competing in a contest to see who can make her man (me) cum fastest.

As if you’re about to begin a long prison sentence, and mine is the last cock you’ll see for years.

Like you believe you’re being filmed secretly for a movie about women who give great head.

There were others, but these are the ones we drew from the envelope. [Close readers will recognize that all these have been mentioned in my various “How to suck my cock” posts from years ago.]

At some point, Charlotte became convinced that all of the entries in the envelope had to do with sucking my cock. She was [ding ding ding ding ding!] correct!

All this was before we went to the strip club. For which…. tune in for part 2.