Charlotte’s Kinky Date free porn video

In June of 1975, I made a misguided attempt at a bar pickup in New York. Actually, technically, I did pick her up. I was twenty and she was about twenty-six.

Somehow, I convinced Charlotte to take me back to her nearby walk-up apartment. She cock-teased me by doing a striptease, and then she had me masturbate on a couch as she watched. Then, in a very abrupt and unsubtle way, she threw me out.

At that time, I had a girlfriend named Michelle up at City College. She got me a job as a paste-up artist at a company on West 24th Street; this was only a few blocks from the Albion Bar where I had met Charlotte.

I wouldn’t say I was infatuated with Charlotte, but every now and again I would walk past the bar on Seventh Avenue. One hot and humid afternoon I went past and looked in. There was my dark-haired Charlotte at the bar. I could see her in profile, and I noted the Louise Brooks-style hairdo I had seen before. On some impulse, I went in to talk to her. It was now August and several weeks had passed since the previous experience.

I was grateful for the cool air in the bar. 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 and the ways they presented themselves. I think she had the same straw hat, but now it was on the bar with her sunglasses. She was wearing her regular glasses; I knew she was a bit vain and often avoided wearing them 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 this 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 of 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 assumed 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 of 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 start the game and I needed a moment to get ready. My college-boy self was surprised that Manhattans came in martini glasses.

I had decided to be bold and make a proposition to her immediately. At first glance it seemed like a bad idea, but hadn’t the notorious Rasputin gotten women by grabbing them and fucking the one in a hundred who went for him? I obviously was not that kind of man, but I decided I had nothing to lose by being direct.

But what would I use as my point to entice her? Maybe it was a lucky guess or maybe it really was intuition. I decided to go kinky and propose some BSDM action. I got my courage up and tried to be off-the-cuff about it. “Charlotte, have you ever had a man discipline you?”

“What the hell does that mean?” She had used some mild cussing but she didn’t move away from me.

“What I mean is: if a woman is, call in misbehaving, a man will get her back in line by spanking or paddling her bottom. It could be her boss, her husband.” I didn’t explain why some random guy in a bar would have the authority to do that.

She had turned 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. Am I interpreting this correctly as interest in this idea, or am I imagining it?

She said, “That’s for teenagers.”

“It’s for grown-ups too. Like my girlfriend; she can be quite a snip at times. If she really pushes it, I have to take her over my kneed and thwack her backside.” Thwack sounded like British spanking porn.

“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 crossed her legs. I had learned a bit about body language 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 women, 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 was waiting for her response. She had been looking at me and paying attention as I spoke. 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; she shouldn’t have done that with any man, even one as young and inexperienced as I was. Anyway, I didn’t scoff at her opinion. I said, “Whatever I do, you know you can handle it. We saw that last time.”

“What are you, a sophomore, right?“

“I’m going to be a junior next month.”

“Oh, a big man on campus.” Then continued, “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; that was what came to my mind. I had seen it when she took off her panties in her striptease. I decided that this was not the moment to mention that. I said, “You’re griping about it now, I mean where I chose to sit?”

She snickered at that. A few moments later, “All right, I am kind of curious about what kind of 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 look at her as we walked up the street. She kind of sashayed as she walked; she seemed to go for self-dramatization.

Nevertheless, I was amazed I had gotten this far with my daring proposal.

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 done spanking sessions with girls on sofas or in armchairs. Sometimes I preferred to use a chair like this one.

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 the rims of her sunglasses. Is this a come-hither look or is she just fooling with me?

There were two sofas in the room, facing each other. She sat on a couch – the one where I had masturbated last June.  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.”

I decided to make an end-run around that statement. Instead of confirming or denying it, I just ignored it. I went directly to the point and I would see how she reacted.

“Here’s what I propose to do: I’ll take you over my lap in this chair. Then I’ll spank you on the seat of your nice little denim skirt.” Somehow complimenting her clothes seemed like a good idea. “That will just be a warm-up. Then I'll lift up your skirt and take your panties off – assuming you actually are wearing panties – and I’ll use my hand to beat your bare backside. I'll give it to you pretty hard and for a while too, like several minutes.”

Jesus, was I actually saying these things to a virtual stranger? I wished she had offered me a drink before I had launched into this thing.

“Then as a finale, I’ll whack you on your ass with a hairbrush.”

I didn’t actually know if she had a suitable hairbrush, but I assumed there would be some other implement, like a kitchen spoon, that I could use.

During this talk, I carefully watched her for more clues. I thought I saw a few. She licked her lips and then she crossed her legs. Her demeanor seemed different. She looked tense and maybe a bit nervous. But she didn’t speak to me. I had to press this a bit more.

“You do have a hairbrush here? A wooden one?”

"Yes, I have a hairbrush." Then she surprised me by getting up and retrieving it from the bedroom. When she was back she didn’t hand it to me; she dropped it on the floor. Then she stood and 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-one degrees out in the street; how did she manage this cool appearance? She also looked intensely sexy now.

I noticed that she still had her hat one. I thought it was time for a forward pass and I hoped she caught it. I asked her, “You still think I don't have the nerve to do this?”

“Yeah, basically, I don’t.” Was that an opening? I tried to exploit it.

I said, “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."

I thought that she might be lying about this and she might be thinking otherwise. I said, “So you think this is just a lark?”

She didn’t answer but she did come over and placed herself over my lap.

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

Wow, am I really going to discipline and dominate this woman I hardly know? We didn’t even have a safe word. My girlfriend Michelle and I had a safe phrase, which was 'chicken pot pie.' That seemed unmistakable as an attention-getter during a session. Neither one of us had used it yet.

I was pretty tense and nervous myself, but I couldn’t back down now. I had put my left hand on her lower 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 ahead, give it your best try.” I thought, I'm going to do more than just try.

I started by spanking her on the seat of her skirt. She made a few soft noises from the pressure of the impact. By that point, I had an erection that would stay intact throughout the rest of the session.

I asked, “Is this having an effect?”

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

I wasn’t going to linger in the over-the-clothes phase. Without comment, I flipped her skirt up. She had nice panties. They had 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. Is she anticipating the next part?

Charlotte's ass somehow looked bigger bare than clothed. She had no tan lines. I found out later that 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 wanted to take her attitude down a few pegs. I wasn't thinking of it as some kind of joke. 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 left a handprint on her right cheek and another on the left; she groaned with each one.  I was convincing her of something. I got a rhythm going with the spanking. I wasn’t one of those guys who use both hands.

Her grunts were more insistent now that she was getting it her bare rear end. Then she started to wriggle around and she said, “ouch,” or, "ow,” after each stroke.

“Still think this is a stunt?”

“No, it hurts. How long is this going to go on?”

“As long as I think necessary.” I added, “I suspect you are going to lose more and more of your snippiness as this goes on.”

As the spanking continued, she started to move her feet on the floor. Then she brought her legs up and waved them around. I did notice her nice sandals. I used my left hand now to grip her around the waist and keep her in position.

“Charlotte, you’ve been a very naughty lady. Take your discipline like a big girl. By the way, baby, your ass is reddening very nicely now.”

She replied, “I can only imagine it.”

Her skin was pale, and the contrast between that and the spanked areas was noticeable. I wondered how much of this she could take. I wasn't sure that my own hot and sore hand could take it, but that was the price to be paid.

I really should have kept better track of the time then. Her feet were on tiptoes. She squirmed around and rocked her hips back and forth. All of this felt great on my unseen boner. She also whipped her head around and her hat flew off.

I decided it was time to stop for the moment and go into lecture mode.

“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.’ ”

“Okay, okay, 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 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.

“You can rub your ass now.” She reached and back and grabbed herself.

She said, “It feels so hot back there. You could fry an egg on me.”

I laughed at that. “They used to say that about sidewalks in the summer, like in the Daily News. 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 curious to know how the next step would go.

I said, “There's something so pleasing about exposing the buttocks of an arrogant woman and using a good spanking to put her in her place.”

“You’re kind of fucked-up, do you know that? How do you come up with these things?”

“You know it’s a common fetish. And don’t kid me, I suspect you like it more than you’ll admit. I bet your pussy is wet right now.” I noted that her legs had drifted apart and a few dark pubic hairs were sticking up.

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

“We'll see, maybe later. Now, my dear, it’s 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 ten. What do they call that, ten of the best?”

“It sounds like ten 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. “You haven’t, not quite yet.”

She indeed got up to retrieve the brush. She could have walked away if she wished. Instead, she positioned herself on my lap again and said one word.

“Please.”

“Please what? You want twelve? Fifteen?”

“Oh no, ten is – perfectly adequate.”

As I had implied, I did use moderate swings on her. Yet the sound of it was loud in the room. She moaned and yelled. I could see that I was bruising her in a few spots. And yet I kept going beyond ten; she didn’t object. I didn’t keep track of the number.

When I was done I said, “Okay my dear, you can get up now.”

She jumped up and immediately gripped her own ass again. She glanced back at herself, “Look at what you've done to me?”

“I’m looking all right.”

And she looked back at me. She finally lifted her glasses so I could see her whole face. There were tears in her eyes and I saw anger and humiliation. Maybe there was some expression of lust too.

“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 gotten that drink earlier so I could savor this moment. She probably would have given me one if I had asked, but I was rather distracted then.

She went over to the wall here 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.

Then I had to top myself. “From the way your ass looks, I don’t think you’ll be on any barstools soon.”

That got through; she looked over her shoulder and her look was venomous.

I said, “What is that look supposed to be? Is that your version of a bad girl’s pout?”

She silently mouthed something and I could read her lips, fuck you.

I laughed at her, “I should hang a sign on you, 'I’ve been spanked because I’ve been such a bad girl.’”

I customarily didn't prolong this stage. I had one more act planned for this comedy/drama, but I was considering dropping it. Maybe I had had enough amusement for today.

“You can rub your bottom again if you wish. Corner time is over.”

In a moment she was back on the couch again, looking at me from the same position as before. She seemed to be careful about placing her battered ass on the cushion.

She said, “So what happens now?”

“What do you think is going to happen?”

“You tell me; it’s your show.”

It was an opening perhaps to continue my plan. Then she said something that triggered me, made me decide to do that final act. What she said was perhaps not that bad. But it set things in motion.

She said, “So, you got to live out your jerk-off fantasy. Was it everything you hoped for?”

“Well, it was really for your benefit, not mine - but yes, it was very satisfying.” I didn't let her get the next word. I said, “I am feeling kind of hungry. I think I’ll go over to that Chinese place on Eighth Avenue.”

She seemed puzzled. I continued, “I know I have to deal with waiter service but it seems worth it.”

“Well, I’m going too.”  There was more than a bit of worry in that.

“No, I am going by myself.”

“But then you’re coming back here, right?”  It seemed that her voice was firming up.

“No, I’m going home after that.”

“Are you going to see that girlfriend of yours?” Somehow that would be an acceptable excuse, I guessed.

“I’m not, I just have some things to do. What did you expect?”

She said, “I expected that maybe, no, not maybe, but definitely, you would bang me.”  She had a strangely formal tone in her voice. I thought of some rich lady dressing down an employee of a country club.

“Oh, I see, you admit that you’re horny now.”

“Well, Christ, that's what you wanted, right?”

I amazed myself with what I said next. “Too bad. It’s like I had to do with myself last time. Go wank yourself, you selfish twat.”

Why did I have so say something that nasty? What ugly part of myself was I revealing with that? I had launched a grenade into a minefield, just to see the explosions. These were indeed impressive.

She stood up, “You little fucking asshole, you’re finally getting your revenge.”

“It’s not really revenge.”  I was shocked by how fast I was losing my nerve.

Now she was loud, very loud, “If you are getting out of my house, then get the fuck out now!”

That seemed like good advice. I got up and moved so that the couch was between us. Even though the mines were now exploding through a chain reaction, I launched one more grenade.

It came out sounding like a schoolyard taunt, “You bitch, you’re such a cock-tease.”  That wasn’t fair; she had been just about to prove me wrong, but the point of no return had passed.

She got a bit quieter now, which was even more menacing. “You see that window?” That was the one with the air conditioner on one side. “It’s three stories up. If I send you out that way, you'll break your neck, at the very least.”

She was moving to go around the couch. I moved quickly towards the door. As I opened it I heard, again not too loudly, “I could absolutely kill you right now.”

I admit, I was afraid. I believed she had the physical strength to take me on if she was motivated - and she was obviously motivated. Having the apartment door between us was not enough; the building door wasn’t enough either. As I walked along the block I kept looking back to see if I was being followed.

Why have I blown my chance to have sex with this woman? I had, just for the fun of emotional experimentation, acted like an asshole and then I became a coward. I already had a girlfriend. I could have found entertainment in reading, going to Mets games, and continuing my love affair with Michelle. Or maybe I should have done something productive, like putting in more hours at work.

When I got to 23rd Street, I calmed down a bit. I knew she wasn’t going to come through the streets of Chelsea hunting me with a knife from her kitchen. I tried to delay making the next decision. I glanced at the subway entrance where Michelle and I had our first kiss the previous year. When I couldn’t stand to wait any longer, I dialed Charlotte from a payphone. I had somehow gotten her number during the previous visit.

“Hello?”

I jumped right in, “Charlotte, would you like me to get something for you? I'm right here by the restaurant.”

Her voice came through level, normal, “Sure, let me think.”  Then I got her order; it was a simple matter to memorize it. I said, "As soon as they have it ready I’ll bring it over.”

“I’ll be here.”

When she opened the apartment door, we looked warily at each other. Her hat was off but her glasses were on her face.

She said, “Come on in.”

I sat down on “my” couch and put the bags on the coffee table. She sat next to me, on my left. I didn’t apologize, but I immediately got into explanations, “These games can get pretty intense.”

She replied, “I know that; I thought I went in with my eyes open.”

“It may take a day or two or maybe, even more, to unwind completely.”

She nodded, but she didn’t respond immediately. Then she offered, “I masturbated when you were out. I think you knew I would.” Somehow I was bothered that she had shared that with me. I had to stifle saying, I’m sorry.

I noticed that her underpants were still on the floor. I tried to lighten things a bit, “So you did a Broadway boogie-woogie?”

“Excuse me?”

I pointed down, “The design on your underwear, it looks like the painting.”

“That’s because the design is the painting.”

“Really? Where did you get them?”

“On Bleecker Street; where else could you get Mondrian-themed panties?”

We relaxed a bit at that. She lifted her skirt and took my hand, “Here, feel how wet I am.”

What I really wanted to do was kiss her, so I did. Then she put her head on my shoulder and sobbed. She pulled back and I saw that she was crying real tears. I had really hurt her, not with the brush but with my words.

She said, “I know this is kind of silly.”

“No, it isn't silly. We seem to really get off on messing with each other’s heads. I think you admitted last time that you enjoyed it in some way.”

We pondered that for a moment and then I looked at the bags of food. “That smells pretty good,” I said.

“So what do you want first, the food or the sex?”

I didn’t hesitate, “The sex.”

There was nothing tentative about what we did; we just grabbed each other. She said, “Sit on a footstool, and I’ll get on top of you. I’ve got to be careful with my sore ass.” There wasn’t exactly much foreplay. After she had undone my pants, she lifted her skirt, got on me, and I slipped into her. As she bounced on me I lifted her blouse and I tried to undo her bra strap.

She said, “Here, let me do that.”

Sometimes it’s nice to be pushing up into a woman instead of pushing down into her. She put her arms around me and put her boobs against my face.

We both seemed frantic. I’m sure she made a lot more noise than I did. As her climax approached, she lifted her feet off the floor and spread her legs wide. She braced herself by holding on to my shoulders. I in turn held her around the waist so she wouldn’t fall over. The sound she made at her peak was a long keening note, like, “Ah-h-h-h.” It was quite loud.

Her enthusiasm inspired me to quickly come too. Just as I reached that point, I said one of those silly coital statements. “You took your panties off for me, so I’m going to put a hot load up into you!”

When we were done, we didn’t look at each other. In a few moments, she got off of me and sat on the sofa. In in turn went over to the other sofa facing hers. Now our eyes did meet. I don’t know what my expression was like, but she looked stunned. Also, she was disheveled with her tits hanging out and her skirt up around her waist.

I wondered if this was going to be a one-day stand. Then she said, “You’re going to spend the night here, right?”

I had to decide if I should commit to that. What benefit would I get from a longer-term relationship? There were downsides: Charlotte being older and presumably more mature; then there was Michelle to think about.

I blurted out, “Of course I am staying here.”

*****

The next morning, after our breakfast of Cheerios and coffee, she gave me a large manila envelope.

“What is in this?”

“It’s a photograph; take a look at it later. I want this back, so take care of it, but you can borrow it for a while.”

I shrugged and accepted her vague answer as part of her quirkiness. Later, when I was on the subway, I opened it and took out the photo. It was not a snapshot; it was a large print, a black and white picture in portrait mode.

It showed a much younger Charlotte standing in what seemed to be a schoolyard or park. I flipped it over and someone had written, “Graduation, Middlesex Middle School, Darien, CT, June 1963.”  I pondered how this serious-looking girl had evolved into the woman I knew now.

By the time I was fourteen myself, in 1969, Charlotte was twenty and starting her hippie year in the East Village.  That July, I went to Boy Scout camp for the last time.

Anyway, I wondered, why had she had given me this photo? Somehow I didn’t want to think too closely about that.

I looked up and noticed that somebody - almost surely an adolescent - had changed the roll signs in my car. According to those, I was riding a nonexistent FF train traveling between the improbable terminals of Far Rockaway and Brighton Beach.

I used to do that myself in 1969 - change the destination signs for some kind of fun. It wasn’t malicious, although it may have disoriented passengers along the route. I just wanted to see a train roll out with an unusual set of signs.

I looked back at the photo and it struck me that Charlotte was - maybe unconsciously - trying to emphasize the age difference between us. Did we perhaps both understand that eventually there would be an expiration date on our relationship?

I thought, that doesn’t matter yet. For the moment we have each other.

#######