Charlotte’s Sexy Web Ch. 02

May 1, 2024 // By:analsex // No Comment

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[The first chapter of this is here. It describes Charlotte as a twenty-six-year old perennial student at the City College of New York. Her boyfriend, the narrator, is six years younger.

A role play with another girlfriend – Michelle – is mentioned in the story and described here.]


In the first days of August 1975, right after I came back from a month-long trip out West, Charlotte and I were hanging out in a coffee shop.

I said, “I’ve been thinking of my own role-play concept. Everybody else seems to create some, so I got one of my own now.”

“That’s great. Tell me about it.”

“It’s a sequel to what we did in June, the pick-up game at the Albion Bar. I, or he, comes back and finds her there again.

“He’s he stalking her?” It was interesting how we had figured out that we were talking about the characters we played. Like Venn diagrams those characters only partially overlapped our real selves.

“Not really, he swings past the bar on occasions and at the second time she’s there.”

“That sounds promising. In fact, I’m really impressed.” She wasn’t faking her anticipation here.

I said, “I have some ideas about this but I’m not going to tell you about those now. I’ll be in the lead and you’ll follow. Think you can deal with this?”

“Of course, I can deal with it.”

I thought, maybe you can’t. For the most part she hadn’t experienced the more disturbing results of role playing that I had seen.

We worked out a weekday, late afternoon deal just like the time before. The appointed day was even hotter and more humid than the first one. This time I was grateful for the cool air in the Albion. My clothes were different but just as bad as before. I’d have been hard-pressed to find anything better in what I owned.

I strolled over and sat to her right again, but this time I went to the stool next to her.

“Hi Charlotte.”

“Hey, look who just walked in.” She seemed pleasant enough but I caught an undertone, something like, look what the cat just dragged in. She continued, “What have you been up to?”

“I work right over here on 24th Street, part time. I do paste-up for a typesetting company.”

“How did you get that?” She seemed to be just filling in conversational space.

“My girlfriend works there; she got me in.”

“That’s so cute; it must be fun to have her there.” There was a contrasting nasty and nice tone in her voice.

I looked her over; I loved noticing the details of women I was sleeping with. I think she had the same straw hat, but now it was on the bar with her sunglasses. She was wearing her regular glasses, which I knew she often avoided if she didn’t have a specific task at hand like reading a book. I guessed the task now was to see my face during the game.

I continued the rest of my hot-weather Charlotte inventory. She had one of her trademark hairbands, this one white with red dots. Her blouse was a white pullover, sleeveless; her skirt was light blue denim, short enough to be interesting but not enough to be brazen. I always wondered if women ever used the back pockets on skirts like that.

And finally there were brown sandals instead of white ones. Overall, it was a fine balance between sexy and subtle. My next move after collecting these facts was to compliment her. Was she fetching, delightful? I ordered my drink now to give myself a bit more time to think. It was going to be a Manhattan, a cocktail I had never even seen before.

“Anyway, Charlotte, you look great today.”

“Well, thank you!” I thought she might add, not that I care what you think.

“We sure had a notable time when we met here back in June.”

“Oh that; look, so I had a few laughs at your expense. And you really have nothing to complain about.”

“Really? How so?”

She lowered her voice, I assume so no one could overhear her. “That peep show thing I staged for you. Remember?

“I remember. I also remember how you got rid of me.”

“Come on, I was grouchy. It had been a long day. You can’t be that sensitive.”

There’s the door; I’m showing it to you. That had been one the things she had said during that game. Was that such a big deal or not?

My drink arrived and the timing was perfect. I was just about to push the game up a notch and I needed a moment to get ready. My college boy self was surprised that Manhattans came in martini glasses.

I had a question for her, a proposal actually, and I tried to be off-the-cuff about it. “Charlotte, have you ever had a man discipline you?”

“What the hell does that mean?” Her first, mild cussing. Of course the real Charlotte knew what I was talking about. I had firsthand experience with her taste for that kind of activity.

For the game I had to come up with the right word for a part of the female anatomy; I didn’t want to overplay it at the start. “What I mean if a woman is, call in misbehaving, a man will get her back in line by spanking or paddling her butt.”

She had turned Ataşehir Yabancı Escort her face to me and I was alert to what her reaction would be. She blinked and I’m sure she swallowed hard. There was a quiver in her legs and she squirmed on her seat; then she opened and closed her thighs a couple of time. It was my familiarity with the real Charlotte No. 1 that gave me clues of what to notice about this role playing Charlotte No. 2.

She said, “That’s for little kids.”

“It’s for grown-ups too. Like me girlfriend; she can be quite a snip at times. If she really pushes it I have to take her over my knee and thwack her.” Thwack sounded British and I knew Charlotte had an interest in all things Anglophilic.

“I’m not sure I believe you, but even if it’s true your girlfriend sounds weird.”

“No, she knows she needs it, she knows it’s for her own good. Right on her bare ass, knickers down as they say in Britain.” I leaned forward and said quietly, “And she likes it too.”

Charlotte No. 2 crossed her legs. I had learned a bit about body language in recent months and I always noticed what women did with their limbs. She started kicking the bar panel, not hard but steadily. I waited for a reply but she went back to her tonic drink.

I tasted my Manhattan and tried to form an opinion about it. Then, as I had the floor, I did my bit as a tavern pundit. “It’s not just a physical thing, it’s emotional too. People have guilt and other difficult feelings. This allows them a release. That’s why people, especially woman, often cry during a spanking. It’s not just the pain, it’s a cathartic experience.”

Now that I had demonstrated my liberal arts training, I waiting for her response. She had been looking at me and paying attention to me. She finally tried for nonchalance, “Okay, so what?”

“I think that you could use such an experience; I think you have some feelings you’d like to get out.”

“And who would do that for me?”

I came in at a slightly indirect angle, “I’d like to talk to you about it. Let’s go to your place and I’ll tell you what I think.”

“Oh, good try.”

“I’ll give you a different kind of incentive. You’ll get a chance to mess with my head again, and that was fun.”

She shook her head, “I won’t admit to anything like that. Besides, I don’t think you have the nerve to follow through even if I gave you the chance.”

A direct challenge; Charlotte No. 2 should have known not to do that with any man, even one as young and inexperienced as I was. I let her have her opinion for the moment, “Whatever I do, you know you can handle it. We saw that last time.”

She said, “I wonder – well I wonder if today is such a dull day that I’d actually . . .”

She didn’t finish her sentence so I let her think about it as I tried my Manhattan again; I was probably too young to appreciate its taste.

We sat in silence for perhaps a minute. When she did speak it was, “Why did you think you could just sit on the stool next to me”

Because I’ve seen your cunt was what came to my mind, but that would be too much. I said, “You’re griping about it now?”

She snickered at that. A few moments later, “All right, I am kind of curious about what kind nonsense you’ll come up with.” She gestured towards the door. I was going to abandon half of an expensive drink again but there were more important matters to consider.

This time she wore both her hat and sunglasses in the street. Also, she wouldn’t talk to me. She didn’t start a conversation and I sensed I shouldn’t either. This gave me the attention to notice that she walked differently. No. 2 kind of sashayed as she walked. No. 1 didn’t go in so much for self-dramatization.

We were quiet going through the streets and up the staircase to her apartment. Inside she got the air-conditioner going without the fuss of last time. I sat in an armless chair by the far wall. I had already done this with her numerous times on a sofa or in a chair. For some reason I preferred to use a chair for this session.

She was looking out the window even though there was little to see except the building across the way. Then she looked back at me over her shoulder, over the rims of her sunglasses. Was this a come-hither look or just fooling with me?

When she sat on the couch – my New York Times couch from last month – she went through her purse and got her regular glasses on. One leg was up on the cushions so that she could look down the length of it at me. She said, “What I think is, you’ve had some intense jerk-off fantasies about me, starting with the night you left that time, and now you want to tell me about them.”

My response went around that directly to the point, “Here’s what I propose to do: once you’re over my lap, I’ll spank you on the back of your nice little denim skirt.” Complimenting her clothes seemed like a good idea. “Just as a warm up. Then you’ll get my hand on your bare backside.” It seemed good to vary the words; backside sounded Ataşehir Yeni Escort more blunt, perhaps. “I’ll give it to you pretty hard and for a while too, like several minutes. And then I’ll finish with a hairbrush, maybe ten whacks with that. I’m sure that will get your attention.”

During this I carefully watched her for more clues. I saw one: she briefly licked her lips. But she didn’t speak at the end of my little speech. I had to press this a bit more.

“You do have a hairbrush here? A wooden one?” Of course I knew she had more than one.

“Yes, I have a hairbrush.” Then she was up and retrieving it. When she was back she didn’t hand it to me; she dropped in on the floor. Then she leaned on the end of the couch and folded her arms.

I had a thorny problem to solve here: how to get her from the local to the express track. Just looking at her distracted me. It was ninety-six degrees out in the street; how did she manage this cool look? I remembered the first time I saw her when she walked into my class. She was dressed for her job, she had a blazer and slacks and shoes with heels. And yet there was a certain – humbleness was not the right word, but her attitude may have been: this is where I have to be, so here I am.

I think I had fantasized about her just twice between September and November. Maybe it was the way the breaks went, but the women I knew would not attract undue attention if they were just in school or an office or on the street. But when they emerged from the crowd – well, Charlotte looked intensely sexy right now.

She still had her hat one; I suppose Charlotte No. 1 remembered I liked it that way. I asked her, “You still think I don’t have the nerve to do this?”

“Yeah, basically I don’t.” An opening?

“Then come over here and find out.”

“All right, why not? I’m not worried, you don’t have the strength in your arm to do any real damage.”

Baby you know that just isn’t true, you know first-hand that it isn’t. I said, “So you think this is just a lark?”

She didn’t answer but she did come over. I think she fell out of character a bit; Charlotte No. 2 should have been more tentative when placing herself on my lap. There was a bigger issue: how was this gap in plausibility bridged? Why did No. 2 actually do this?

I came up with: Charlotte No. 2 has heard about this or read about it and was considering it long before I mentioned it in the bar. I remember her shuffling her thighs, kicking the bar panel. Later I would have to ask No. 1 if my guess was correct. If it had been, I would praise her for her fine gamesmanship.

“So here I am,” she said. “Punish away.”

I had done this with her before and she had switched and done it to me, so we knew what to expect. We even had a safe word, or rather a safe phrase that we had agreed to many months ago: “chicken pot pie.” That had been my contribution; it seemed unmistakable as an attention-getter during a session. It had turned out that neither one of us had used it yet.

I had my put my left hand on her back, at the bottom of her blouse. I said, “Are you sure you’re ready for this?”

She looked over her shoulder at me. “Go head, give it your best try.” I thought, I’m going to do more than just try.

I started in on the seat of her skirt. She made a few soft noises but I knew that it mostly the pressure of impact that was affecting her. I did that for less than a minute. By that point I had an erection that would stay intact throughout the rest of the session.

“Is this having an effect?”

“Hah, you’ve hardly put a dent in me.”

I wasn’t one to linger in the over-the-clothes phase. Without comment I flipped her skirt up. Nice panties, some design on them that reminded me of a Mondrian painting but that probably was just a coincidence. I said, “Let’s skip the over-the-panties part.” I quickly lowered those to her ankles. She said quietly “Oh” or “Ah;” her legs quivered. Those were Charlotte No. 1 reactions that could not be stopped.

Charlotte’s ass somehow looked bigger bare than clothed. That was fine with me; in fact I believed almost any female ass was fine. There were no tan lines because she avoided going to the beach or pools.

“I remember this from June,” I said. “You have a superb ass.”

She laughed, “You should grovel before me in gratitude, just to see it.”

I had this impression of spanking Charlotte No. 2; I really felt I had a grudge with her and I wanted to take her attitude down a few pegs. I wasn’t thinking of it as playacting now. What did the “sound” in sound spanking mean? I’d have to look it up later. I’d then know that synonyms would include solid, convincing, satisfactory and persuasive.

I started convincing her of something. Her grunts were more insistent now that she was getting it her bare rear end. After a couple of minutes I stopped and rubbed her now sore bottom. “Does that feel better?”

A moan, “Yes, I admit it, it does.”

I said, Ataşehir Masaj Salonu “I expect you are going to lose more and more of your snippiness as we go on.” That word wasn’t as loaded as bitchiness.

“Rub me more and maybe I’ll make it worth your while.”

“Trying to be coy I see? I don’t think so, not just yet.” I got back to spanking her; in another minute her feet started to move around on the floor. I thought, great sandals. One her hands gripped the chair leg and the other my leg.

“Charlotte, baby, your ass is really reddening nicely.”

She replied, “I can only imagine.” Charlotte No. 1 wouldn’t have to imagine.

I knew she – or at least the Charlotte I knew – could take a lot of this, almost an indefinite amount. I wasn’t always sure that my hand could take it, but that was the price to be paid.

I really should have kept better track of the time then. Around the five minute mark she was on tiptoes and she had raised her hips to make a better target. These were also Charlotte No. 1 characteristics that I knew well.

“How long is this will this go on?”

“As long as I want it to. Do you want me to stop?”

“I’m not really sure.”

“So you like it after all?”

“Yeah, I do, I think.”

“Well, I certainly like it.” It was soon time to lecture, to make the lessons clear. I stopped for the moment.

“Now, are you going to be a polite lady from now on?”

“You’ve got to be kidding me.”

“No, say it, ‘I’m going to be a polite lady from now on.'”

“Ok, ok, I’m going to be a polite lady from now on.”

“Also, you’re not going to bring men home and mess with their heads.”

“You came and got me, twice, remember?

I said, “That’s doesn’t matter; what does is what happens when you get back here. Now say it.”

She complied, “I’m not going to bring men home and mess with their heads.”

“That’s good. Maybe you should just stay out of bars for a while too.”

She looked back and glared at me, but I had started rubbing her bottom again. That was almost universally enjoyed by every spanking aficionado. I saw her expression melt.

She said, “It’s so hot back there, you could fry an egg on it.” That was a quip I hadn’t heard from her before.

“They used to say that about sidewalks in the summer. Anyway, my sweet Charlotte, you do have an amazing rear end.”

“You said that already. And get a good look, because this is the last day you will ever see it.”

“What, no more peep shows? I’ll just have to prolong this one then.”

I got back to whacking her and I included the tops of her thighs a few times for variety. Then I stopped, mostly because I was getting impatient for the next steps.

I said, “There’s something so pleasing about taking down the pants of an arrogant woman and putting her in her place.

“You’re kind of fucked-up, do you know that?”

“Don’t kid me, you said like it too. I bet your pussy is soaked right now.”

“Well don’t touch it, that’s not part of the deal.”

“We’ll see, maybe later.” I noted that her legs had drifted apart and a few dark pubic hairs were sticking up.”

I said, “Now, my dear, time for the hairbrush.”

“You aren’t really going to do that, are you?”

“I said I was and I’m keeping my word. I’ll go easy on you. I’ll only give you six. What do they call that, six of the best?”

“It sounds like six of the worst. I’ve already got the gist of this I think.”

“You mean of chastisement?” I was fond of that word although it was a bit pretentious. “Not yet you haven’t.” I knew Charlotte No. 1 could take a lot more than six of these but Charlotte No. 2 was new to this. Nevertheless I got right into solid whacks. On the second one she said, “Please.”

“Please what? You want ten, twelve?”

“Oh no, six is – just fine.”

When I was done I had an urge again to feel between her legs even though I had sort of promised that I wouldn’t. I knew what I would find anyway.

“Okay my dear, you can get up now.”

When she did she immediately gripped her ass and rubbed it. She looked back at herself, “Look at what you’ve done to me.”

“I’m looking all right.”

And she looked at me, or rather both Charlottes did. She finally lifted her glasses so I could see her whole face. There were tears in her eyes and I saw anger and humiliation and lust and even love in them. She had a talent for role playing but she didn’t have Michelle’s ability to completely go into a character and stay there. Michelle’s slips were minor and rare.

“It’s corner time now. Stand facing the wall over there and hold your skirt up.”

“What is this, grade school?”

“No, think of it as a finishing school for wayward ladies like you.”

I pointed with the hairbrush. She went, flipping her glasses back down and stepping out of her panties so she wouldn’t trip on them. I wished I had poured a drink earlier so I could savor this moment. Actually, she probably would have given me one if I had asked but I wasn’t going to break the flow by having one of us go into the kitchen.

She was over there next to the whirring air-conditioner. I said, “I think you’ll be a better person from now on.” She gave an exaggerated sigh, and I myself was struck by how ridiculous my comment was.

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