Charlotte’s Sexy Web Ch. 03


[The previous role-plays with Charlotte (the “bar pick-ups”) are here and here. A story with another character mentioned in this story, Michelle, is here.

Part 1 of this story contains the domination/sexual aspects of the game. Part 2 is a conversation between the two characters – a sort of emotional aftermath.]


For a period during my sophomore and junior years at the City College of New York I had several girlfriends going at once. Nowadays that is called “spinning plates” but back then it was a happy set of coincidences caused by the fecklessness of everybody involved. For a while I had a good time with open-relationship fun and games; everybody knew what the others were doing. I did suspect that the situation wouldn’t last forever but I was too young to worry about it or even fully understand what was going on.

One of these women, Charlotte De Havilland, was a perennial student at the age of twenty-six when I met her; I was still nineteen then. She was scheduled to graduate in June, 1976, a year before I was, but I rarely thought about what would happen after that.

She was tall and dark-haired and since she had grown up in an affluent Connecticut town she seemed very classy to an outer-borough New Yorker like me. When I wanted to flatter her I compared her to Cyd Charisse or Ava Gardner; when I wanted to tease her or simply bug her, I referred to Joan Crawford.

Under her polite and calm demeanor she had a pronounced kinky streak. She knew about the role-playing games that the other women had invented and she went on to create her own. It turned out that she had the knack needed to plan and act in a complex game.


We enacted our third role play game in October, 1975. At that time National Lampoon’s September Back to College issue was out, and my girlfriends had seen it and commented on – favorably, to my surprise.

The most notable thing about this issue was the cover drawing of a professor using a slide rule to spank one of his female students. Her skirt was up, her panties down around her knees, and she held a term paper with a big red F on it.

I was hanging around with Charlotte one day in her apartment in Chelsea, looking at a copy of the magazine.

I said, “I saw this on a newsstand at Penn Station, but I didn’t have the nerve to buy it.”

She found that amusing, “Really? I just up and got it in some store.”

“What did the guy there think?”

“I don’t know and I really didn’t care.” When I first met her I noticed that she was on the quiet side and I assumed she was a bit shy, but she often proved me wrong.

She then said, “So what do you think of it?” She knew I had had a few kinky experiences of my own in the last year or so.

I shrugged, “That girl on the cover, except for her hair color, reminds me a bit of Michelle.” That was one of the other girlfriends, and Charlotte had met her more than once.

“Oh yeah, how so?”

“Maybe, I guess, the same type of ass. Kind of tight and athletic.”

She laughed at that. “I get it. I know you’ve put a few whacks on her butt and she’s put a few on you. Now, I’ve got few scenarios for the two of us. I’m sure you want to hear about them.” I nodded as she leaned forward. “They’re based on this picture. For the first time out we’ll switch it, I want to be the professor and you’ll be the student. How does that sound?”

I didn’t need much for a sale but I pretended to think about it for a moment. “Okay, that sounds promising.”

“Now you may get a somewhat sore behind but there’ll be a payoff in the end.”

I knew enough not to ask her what that was. The creator of a role-play had the right to spring some surprises. I said, “Sure Charlotte, I’ll put myself in your capable hands.”

“Pun intended?”

“Of course, what did you think?”

She asked me, “So when was the first time in your life when you realized you had a kinky streak?”

I said, “I do remember that. I was pretty young, maybe ten or so.”

“That young? Spanked by a tutor or a governess? You know, like in The Confessions of Rousseau.”

“We didn’t have tutors or governesses in the Bronx. We did have TV, and there was the Million Dollar Movie on Channel 9. One day they had this thing on called Land of the Pharaohs.”

“I’ve seen that, I mean the second half. That weird stuff at the end, where they all seal themselves in the tomb.”

“That scene gave me the willies,” I said. “Especially since they didn’t tell Joan Collins, the princess I mean, what was happening. Anyway, the scene I mean was near the beginning. Jack Hawkins is the pharaoh; of course having an Englishman as an ancient Egyptian just seems to work. So somehow this princess gets in trouble with him and he sends her down to the dungeon to be whipped.”

“Ah, the mean pharaoh and the naughty princess scene.”

“I’m surprised he didn’t do it himself, but I guess pharaohs got a little jaded after a while. So Ataşehir Yabancı Escort they actually show Joan Collins getting punished, she’s tied to a column with her arms over her head. She’s got this bra or halter top thing on, or whatever they had back then, and this big guy is whipping her bare back.”

“So that got to you.”

“Oh yeah, the scene was only a few seconds long at yet it set off some circuit in me. I didn’t even know what sex was yet.”

I hoped that Charlotte would offer her own origin story for her fetishes, but that wasn’t forthcoming. So I asked about the game. “Okay, so how old is this professor of yours supposed to be?”

“Early forties I guess. .

I did a quick calculation to get an insight into the character I would meet: born in the 1930s, got her higher education in the 1950s. That was a very different generation from mine.

“She’s literally old school, then.” I said.

Charlotte grinned at me, “That’s right, as you will certainly find out the hard way.”


Part 1

The role-play was to occur in mid-October. She was going to use her own apartment, a third-floor walk-up in the Chelsea section of Manhattan. This would be a stand-in for an office on campus. There was a desk in the far corner of the living room that would be her main prop.

I was going to be a student asking for an incomplete for my final paper. She said to me, “I’m going to be pretty harsh on you. But if you can take it I think the rewards will be worth it.”

We had a safe word, or should I say a safe phrase, which was “chicken pot pie.” She hadn’t used it during her turn the previous spring and I wondered how I would handle things when my time came around.

I arrived at her front door late one afternoon. It was a rather cool day so I had a jacket on. I was carrying a notebook and one other book. The setup was that she was having office hours and I would be arriving unannounced with my request. I knocked on the door instead of ringing the bell; that seemed more likely for a college office.

Professor Charlotte or whatever her name was supposed to be opened the door. She was wearing one of her business outfits: a dark suit, white blouse, heels, her glasses, make-up tastefully done. Looking at Charlotte always gave me a surge, a feeling that I had really lucked out in snagging such a fine-looking woman.

Now, however, she wasn’t smiling at me; she gave me a stern look.


“Excuse me, Professor, I’m Paul from your French history class . . .”

She interrupted me, “I know who you are. I’ve been meaning to speak to you.”

Her demeanor seemed brusque, brittle even. She turned to walk to her desk; I assumed I should follow her. As she sat down at her desk she gestured for me to sit in a chair next to it. She crossed her legs and her skirt rode up well over her knees. I could hear the rub of nylon against nylon and I tried not to get rattled by that – but I did anyway.

“You haven’t turned in your final paper yet. Grades are due the day after tomorrow.”

“Yes, ma’am, that’s why I came here, to talk about that paper.” I never called professors sir or ma’am but it seemed like a good improvisation now.

She looked at me over the rims of her glasses, “Any chance you could have it here by tomorrow afternoon?”

“Ah no, I’m only about one-third of the way through.”

“One-third? I gave the details for that assignment eight weeks ago.”

“Yes, ma’am but I’ve been doing a lot of things, like with the newspaper.”

“One of the things you been doing is taking this course. I’d be well within protocol to fail you in two days.”

“I know, I was hoping you’d give me an incomplete; I could have the paper to you by next week, next Monday at the latest I think.”

“And why should I do that for you if all the other students have done their work on time?”

“Please don’t fail me; I’ve never failed a course before.”

“There’s always a first time for everything. I’ll have to give this some thought.”

Actually she only thought for a couple of seconds and then she said, “Go and lock the door.” When I came back she gestured for me to sit down again in the same chair.

“Now Paul, I will consider giving you an incomplete, but first I will punish you quite severely for your – frankly, your inconsiderate attitude, just blowing off the course and expecting me to bail you out. If you can take that to my satisfaction I will grant you more time to finish your paper.”

“Thank you, professor . . .”

“Don’t thank me until you find out what my conditions are.”

She took a wooden ruler out of the desk drawer, “See this, eighteen inches of hardwood?” I noticed that it said New York Board of Education of the obverse side. She began stroking it, one hand sliding up and down the length of it. For the first time she smiled at me.

“I going to give you about ten whacks with this across your Ataşehir Yeni Escort bare behind. Have you ever been spanked before, even by hand?”

“No ma’am, I haven’t.”

“Then you’re in for quite an experience. I bet your bottom is twitching at just the thought of it.” She was right about that.

She stood up and said, “I you want you to stand over here and drop your pants. Your underwear too. Bend over the desk. If you don’t want to do it, you can get out of here right now.”

I did as she asked. When getting into position I noticed the feeling of air around my uncovered body and I liked the knowledge that this woman was gazing at me.

“So you want an incomplete, is that correct?” She gave me a couple of soft smacks with her ruler. “The nerve of you, waltzing in here and presuming I’m going to save your sorry ass.”

“It’s not like that, ma’am . . .”

“Shut up. You’ve going to have earn your damn incomplete. And that’s if I’m in the mood for it.”

Charlotte reached out and squeezed each of my cheeks. “There’s not a lot of padding on this skinny ass of yours. Well, too bad for you I’m afraid. I’ll warm you up with a bit of hand spanking first.”

She put her left hand on my back and promptly begin with her right one. I found this kind of thing to be rather mild, more pleasurable than painful. After a short time, about a half-minute, she stopped and rubbed me a bit. “Yes, you’re definitely warm now, I can feel it.” Then she looked me over again, “You’ve got an erection, you dirty little punk.”

“I can’t help it. . .”

“I said be quiet, I know how to deal with that. You’ve getting the ruler now; stick that butt out. Higher.” She pushed down on my back to get my head down and then she slid my jacket up so that it was out of the way.

“I want you to count out the strokes, as in ‘One, I’m sorry madam.’ Got it?”

“Yes professor, I understand.”


Before I could reply she had swung back and then brought the ruler down on me. This paddling was different from what had come just before it. The wood had real bite as it caught me on the ass. It probably wasn’t the hardest blow she was capable of but she certainly got my attention

“Ow, one, I’m sorry ma’am.”

She gave me six before pausing. I could hear her breathing heavily. I suspected it wasn’t just exertion; maybe she was excited by this.

“So what have you been doing to waste your time this semester? Running around with that little snip on the paper, that Michelle slut?”

I felt that I had to defend her, “She’s not a slut.”

“Really, I think you’ve fooling yourself. I know for a fact that she’s banging other guys behind your back.”

This Michelle bashing seemed strange. Yes, Charlotte was playing a role – yet I had never heard such hostility from her. Was she perhaps revealing jealousy that she didn’t dare talk about in her real life?

“I’ve seen her sneaking guys into the men’s room down the hall.” I presumed that this was supposed to be Wagner Hall although she hadn’t specified it. Michelle may have told Charlotte about our one time there months before. Had she really been in there again with others?

Before I could spend any more time pondering this, she gave me my next four whacks.

“I see you’re up on tiptoes, always a good sign in these things. But let’s face it, if could see your own ass now. . .”

I heard her laugh, then she said, “How about a few more to sweeten the deal?”

“No, ma’am, I think . . .”

I got three more, “Okay, good luck, a baker’s dozen.” She pinched a sore place on my bottom, which definitely hurt.

“Please, ma’am, don’t do that.”

She went into a baby-talk voice, “What’s a matter, little Paulsy has a sore bottom? Should I kiss it and make it all better?”

I couldn’t help but chuckle at that. She said, “You have these interesting circles on you now; I’d say they’re in the red-purple spectrum.” Then she said abruptly changed her tone, “Go ahead, stand up, you may rub yourself.” I didn’t need any further encouragement. I grabbed my own ass if it might fall off, which is in fact how it felt.

She gave me a bit of time to soothe myself. Then she said, “Stand in the corner and put your hands on your head.” I only had to move a couple of feet to get there. She was standing behind me.

“Listen, my fine young scholar, you ask for an incomplete again and the colors on your rear are going to be black and blue. I’ll beat you until my arm gets tired.”

This seemed like pretty nasty stuff even by the standards of the games I’d been playing. I tried to inject some humor into the situation.

“Well, professor, maybe it would be best if I didn’t take any more of your courses.” She did laugh at that.

“I’ve done this to several other students, all males. Funny, none of them turned me down.” She sneered, “Men are just naturally perverse, I suppose.” I thought, as opposed to you? Ataşehir Masaj Salonu I dared say, “Maybe you enjoy it too, don’t you?”

“That’s none of your business. I have no comment on it.”

She went over the side of her desk; she was close to me, close enough to touch. I looked over at her.

“What are you looking at?”

“I’m looking at you, professor.”

She pushed her glasses back on her head. I knew she did that so I could see her better, see her eyes.

And her eyes looked wild. I couldn’t quite interpret her expression. She was obviously jangled, excited. There was sexual excitement but there was something else there too. She still held the ruler but she may not have been aware of gripping it. Her arm twitched a bit. I was sure now that this wasn’t an act; she had liked punishing me.

Then she said, “And what do you see? Do you think I’m attractive?”

I knew she wanted me to look more closely. I had known her for nearly ten months now, but I felt again that strange role-play sensation – that she was truly this character, someone not Charlotte. I had thought of her as a refined lady from Connecticut; that was a side of her that I was familiar with. She wasn’t merely “nice” because of a good upbringing or because she felt it was expected of her. Her warmth towards me had been genuine. Yet I was curious about what else she was going to reveal today.

I said, “Yes, I do think you’re attractive, very much so.” No ma’am or professor now.

Anger flashed at me. She put her glasses back in place, “You bastard, you think you can just come in here and fuck me?”

“I never said that.”

“No, but I did.” I was truly confused now. She continued, “I teach here, I’ve worked for this, I demand some respect for it. I’m not one of those coed twats you’re used to banging around here.”

I thought, Charlotte, baby you’re really rolling with your role.. But I had seen this before, from her and from other women I had played games with. I remembered Michelle’s kinky yet affectionate office lady character

I was getting erect again in her presence; she noticed that and said, “You’ve got some nerve, being in my office and showing off your cock.”

I decide to play it cool, “So what are you going to do about it?”

As if to contradict her own statement she grabbed me by the hips and turned me around. Then she was down on her knees and started kissing my cock. Okay, I thought, a blowjob is worth a quip. As I ran my hands through her dark hair I said, “Professor, am I still getting that incomplete?”

She pulled back and stood up. “I’m thinking about it.” I thought, oh no, my blowjob had been quickly canceled. But actually I didn’t have anything to worry about. She pulled me over to her desk and she sat down on it. She yanked her skirt up; I looked at her and saw she had a black garter belt and straps holding up her stockings but no underpants.

“Professor, you not wearing any panties.”

“Well I’m a full professor here, it’s one of my perks is that I don’t have to wear them if I don’t want to.” All that and tenure too, I thought.

As I stood between her legs I assumed one of my perks was that I could touch her; I found that her cunt was very wet. I had known how aroused she could get from being spanked but I hadn’t known how much switching roles could do the same thing for her.

She looked down at me and said, “I suppose you want to put that into me?” Before I could answer she said, “You guys are all the same. Well, let’s get to it then.”

After stroking me a few times to ensure I was hard enough, she grabbed me and pulled me in. She was aware that my ass was sore and she was careful about where she placed her hands back there.

“Professor, you’re such a hot lady, you know that?”

“Am I now? You have no idea how nasty, how filthy I can be.” This was getting down a bit lower than I had been prepared to go; I decided that we should just enjoy the sex and deal with any drama later. I said, “Do you like this?”

“Oh yes, very much.”

We had our arms around each other which was more like our real affectionate selves than any impromptu teacher-student coupling would really be like. But then again, maybe these two characters could really become fond each other.

It only took a few minutes for us to finish. Her legs got higher and spread out as she approached her climax. I tried for a little more humor, “Ma’am, may I come in you?”

“Oh yes, you most certainly may.”

After we both came and I pulled back she still seemed tense, tenser than I had ever seen a woman who just had an orgasm. And I knew she had had one by the amount of noise and fuss she had made.

I said, “Kiss me, please.”

She stood up and grabbed me. The kisses from Michelle’s characters seemed to be based on acting techniques. This one seemed spontaneous. She kissed me like I was going to disappear in two minutes, which if I had really been her student would have likely been true.

She looked into my eyes. “You don’t know what it’s like, I sit here by myself and masturbate.”

Who is talking to me? Was this at least partially about the real Charlotte in this real apartment? I was sure at least there was no Mister Professor in her character’s life.