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Teen (18+)

This is a sequel to Protected By Lentz Trucking, Queen of Diamonds, and Mrs. Sykes’s Last Brooklyn Exit.

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I was sitting one day in a bar with my older, classy-lady girlfriend, Holly Sykes. I had met her while I was driving part-time for a car/limo service called Lioness Limousine. She was one of my passengers and we got involved in “activities” inside the car when she rented vehicle for the day. She definitely was the one who initiated the affair.

After a few weeks we got into a more conventional relationship that involved real dates. Before that we only had various BDSM and other sexual activities when she rented a car. I was the one who insisted that we take this to a more serious level; I didn’t want to just be her “boy toy.” At that time, in the summer of 1976, I was twenty-one and she was sixteen years older than I was. Somehow, for a while at least, we clicked together.

She was fairly well-off and lived in the Gramercy Park section of Manhattan. I knew that some of her money came from the divorce settlement with her ex-husband.

She was a tall, attractive woman and she had a knack for always dressing well. Beyond that, she was just interesting and fun to be around. One Friday, after I had come down from summer session classes at City College, we went to the Cedar Tavern in Greenwich Village.

When I had a date with her, I tried to dress a little better than my usual 1970s college-boy slovenliness. No Converse sneakers, for example. We were sitting at a table when she said, “I have a friend, her name is Tiffany Harris, and she is interested in some, ah, kinky activities with a young man.”

“So there are more of you out there. Does every lady on the East Side have some sadomasochistic preference?”

“Well, she certainly does. I can tell you the general outlines of what she wants.”

“Okay, satisfy my curiosity. What exactly is it?”

“It would sort of be like we have done. She’ll book a car and ask for you. Then, as I did, she’ll come up with a pretext for a, ah . . .”

I knew already, “An ass-beating.”

“Yes, that’s it. She’ll have that pretext of course.”

“Of course, there has to be one of those.”

“It will probably be that you are fooling around with her college-age daughter. You, know, oral sex with each other and so forth.”

“Does she actually have a daughter?”

“Yes, but she made up a fictional character named Betsy, who is supposed to be eighteen. The real one is actually older than that. I can tell you what she’ll do to you next.”

“Okay, tell me.”

“She’ll take you in the back seat and paddle you. Like I did, but she’ll be harsher.”

“What you did had quite an impact.”

“Yes, but she’ll be worse. She said you’ll be purple, or black and blue, when she’s finished.”

I tried to be sarcastic but I failed, “Sounds intriguing.”

“Then, if she’s satisfied with you, she’ll invite you to another session in her apartment at a later date. She’ll put you over a couch or desk and cane you. First on your trousers, then on the bare buttocks.”

I expressed some skepticism. “I’ve heard that canings are really painful.”

“Yes, that is probably is worst implement there is. They punish prisoners in Singapore and Thailand and such places with it.” Before I could object she broke in, “But she really knows how to use in properly. She won’t use maximum force and she won’t permanently injure you.”

That didn’t sound very reassuring. I had another issue to bring up. “Is she then going to ask for some – something sexual afterwards, like oral sex or intercourse?” Holly had done that from the very beginning.

“Yes, it’s practically guaranteed.”

“I guess nothing in life is truly guaranteed. Where did you meet this lovely person?”

“She was one of my roommates in college.” Yes, Bryn Mawr, one of the Seven Sisters.

“Nice co-incidence that you met your – well, someone with the same tastes. Is there a Mister Harris around?”

“No, she’s divorced, like I am.” But she had a real daughter somewhere. I wondered if she knew about the games her mom liked to play.

I asked, “Do you have a photo of her somewhere?”

“Yes, I have one right now in my wallet.” She took it out to show me. Tiffany was a tall woman, thinner than Holly. She had short dark-blonde hair. And she was actually fairly attractive.

Holly said, “She’s also a ‘switch,’ like I am. When it comes to thrashings, she can take as good as gives.”

“Amazing how you two found each other.”

I sat there for a little while in silence. Finally I said, “All right, Holly, I’ll consider it.”

*****

The next Sunday I was driving to Manhattan from Long Island City. I was going to pick up Tiffany at her apartment on East 79th Street.

She met my car at the curb and got in before I could get out to open the door for her.

I noted the short, dark-blonde hair I had seen in the photo. Just like Holly, she was istanbul escort a snazzy weekend dresser. She was wearing a short, sleeveless gray dress, and she had some kind of wrap, I’d guess you’d call it, draped over her shoulders. This thing had what appeared to be fake black fur with had a long, dark-gray sash attached.

Her stockings were dark and her shoes were black high-heels. There were black gloves that almost went to her elbows. Like Holly, she was a total MILF and she obviously was classy. I wondered what her personality would be like. I knew she was about to start a game with me so I wouldn’t know her true self right away.

She must have taken a hint from Holly’s playbook, because she was quite cool, almost frosty, from the beginning. She spoke before I could, saying , “Hello, Paul.” Something about her tone hinted that she already knew me, which of course wasn’t true.

“Good morning, Mrs. Harris.”

She had another one of Holly’s moves. She said, “I’d like you to take me someplace where we can have some privacy in the car.”

I had expected this, and had already chosen Long Island City because it was just across the 59th Street Bridge. It was also the location of my company, so I thought I knew the area.

Before I could say more she got right into her issue with me, the pretext for this game. She said, “What you have been doing with my daughter, it’s totally unacceptable.” I wondered how I had even met this girl, much less dated her. “My Betsy is only eighteen, and you are, what – twenty-one? You should know better.”

I had to find out what she meant, so I put on a pretense of innocence, which wasn’t hard because I was innocent. “I’m not sure I know what you are talking about, Mrs. Harris.”

“You know what I mean, do I have to get explicit?” Then, that’s exactly what she did. “I know you’ve been indulging in oral sex with her. You lick and kiss her genitals; it’s called cunnilingus. Then you have her suck on your penis until you ejaculate in her mouth.” She could have just used the term “blowjob,” but she seemed to enjoy describing the details. I was also amused that she was pretending that I wouldn’t be able to define cunnilingus.

I couldn’t think of how to respond, but she had something for me. “You are probably wondering how I know about this.” Yes, now I am wondering. “She gossips with her friends, and they have told me for her own good.” A bigger question was how a guy from The Bronx who drove for a car service got to be with this Betsy person. The story seemed a bit wobbly; I was used to Holly’s better constructed fictions.

“I’ve also heard that you proposed doing it Greek style with her – penetrating her anally.” Wow, this is some pretty hot stuff. I thought of joking with, at least she won’t get pregnant that way, but I held my tongue.

We were entering the lower level of the bridge – looking for fun and feeling groovy, indeed.

She continued her lecture, “Now I’m going to handle this in my own way; I want to make sure you end these activities and stay away from her. That’s why we’re going out here.” She must have deduced that Long Island City was our destination.

I dared ask something, “How are you going to do that, Mrs. Harris?”

“We’re going to park out here, and then I’m going to give you a proper thrashing with this.” She went into her bag and pulled out a hairbrush. And this was one mean-looking one. The head was a rectangular piece of wood that looked to be twice the size of the one Holly had paddled me with.

She said, “First you are going over my lap and getting at least ten strokes on the seat of your pants. Then you’re taking your trousers down, and I’m going to beat you until my arm get tired.”

By buttocks twitched, both in anticipation and in fear. I wondered what kind of sexual act we’d do for an encore. She just had to say more, “You’re going to be seriously bruised. It will be difficult to sit down for a while.”

I considered saying, fuck this shit; I’m taking you back. Maybe it was the prospect of some hot sex act afterwards that kept me going. What if she doesn’t offer anything today?

I shrugged and figured I’d go through with it. Maybe I was actually intimidated by her and I didn’t want to challenge her.

Long Island City was indeed quiet that day, but I had misjudged how open it was. I couldn’t find a hiding place to tuck in the car. For a moment I considered driving down to Maspeth and seeing what that offered.

I drove around and, in desperation as I went north on Jackson Avenue, I turned into a little side street called simply Queens Street. It was short and dead-ended at the Long Island Rail Road tracks. There were a few cars parked on it but no trucks to block the view. I decided it would have to do.

I drove down to the end and parked the big blue Buick Electra on the right side facing the tracks. I waited for Tiffany’s opinion of my choice but she didn’t offer one. I turned off escort bayan the engine and she gestured with her paddle. “Come back here so I can discipline you properly.”

I almost sighed as I got out and got in the back with her. She immediately pulled me over her lap and pushed my jacket out of the way. Then she rubbed her ominous hairbrush over my behind.

“You are a very perverse young man. I bet you masturbate all the time too.” I thought, and what do you do, Tiff, when you have some spare time at home? I had never known a Tiffany and I was just guessing that she might use that nickname.

She slid her implement along my thighs. I heard, “Are you prepared to take your punishment now?”

I tried to be nonchalant about it, “Yeah, sure.”

She immediately raised her arm up high and brought her brush down on me. It seemed that she put some force into the stroke and I got a solid whack. It was only the first one, but I gasped and wriggled after the hit.

“As you can see, or rather feel, I don’t believe in warm-ups. Now I want you to count each one so I can keep track.” Isn’t that her job? At least I didn’t have to say, thank you, ma’am or some such thing.

As promised, I got nine more on my pants. The cloth was thin and offered little protection. I couldn’t help but say “ouch” or whatever before mentioning the number. Her brush had some real bite in it

“Don’t move around so much. This is just the beginning.” Then she said, “All right, young man. Undo your trousers and take them down. Your underwear too.”

When I was back in place, he briefly ran her brush along my body again. “It’s a pity I have to punish such a nice, tight ass, but that’s the way it has to be. It’s a little on the thin side, but I think you can take it.” She put her left hand around my waist; she pulled my pants down even lower. Then she immediately got into whacking me with her toy. The sounds of the impacts seemed quite loud in the Electra’s interior.

I think she avoided using maximum force, but it hurt a lot anyway. She got a steady rhythm going. I couldn’t avoid yelping and bouncing around with each stroke. She said, “Stop making such a fuss. There are English schoolgirls who take a beating better than you do.”

I didn’t know how she’d confirm that. She continued, “Get your ass up higher; take it like a man.” I pushed my feet against the floor and tried to comply with her request. She continued to chastise me, getting back to sexual themes. “I’m sure you masturbate way too much. Did you ever do it thinking of me?”

Well, I couldn’t have really done that because I had just met her. But that wasn’t how the storyline went, so I made up something, “Yes, Mrs. Harris, I admit I have.”

“You really are a shameless young man. Meanwhile, you are exploiting my daughter.

Through some kind of male pride, I didn’t want to complain about my spanking, although it was intense. But she stopped for a moment and asked me, “Is this getting through to you?”

“Yes, Mrs. Harris, it sure is.” I was almost going to ask the standard question – how long is this going to go on?, – but I stopped myself. Yet I couldn’t avoid groaning or whatever each time her brush came down on me.

I lost count and stopped doing that, but she didn’t object. She seemed to go on for a couple of minutes. When she stopped, she said, “I would rub you, but you’re probably too tender back there for that. You can try yourself if you wish.”

I did so carefully, basically only touching the sides of my hips. I tried to look back at myself. She laughed a little at that, “Oh, you look quite different, I can assure you of that. It’s sort of on the red-purple spectrum. I won’t say you took it well, because you didn’t”

I did feel somewhat upset and angry with her and I had an unkind thought, yeah, bitch, wait until I get a crack at you. Then she said, “You may get up now.” I did and I was kneeling on the floor. She moved forward on the seat and said, “I want to show you something.”

She lifted her dress and spread her legs. I saw another of Holly’s tactics. My classy Mrs. Harris had a black garter and straps to hold up her stockings, but no underpants. I could clearly see her pussy. She was breathing heavily and her voice seemed a bit choked. “Notice anything unusual?”

I was breathing heavily too. “Of course; you don’t have any panties on.”

“Well, if I don’t want panties, I don’t wear them.”

I was struck by how fast and direct her next actions were. She got down on all fours on the floor and raised her behind. As with Holly, her backside seemed bigger when exposed than I had expected. All she said was, “Move forward.” I did, and she started to grind her bare ass against my bare crotch. I was instantly erect, hugely so.

I felt her pussy and found it to be wet. “Mrs. Harris, you enjoyed all this, didn’t you?”

“Call me Tiffany. And yes, it always happens to me.” She moaned and rocked while I fingered Bostancı escort her.

I said, “Do you want me to lick you as well?”

She managed to reply, “No, I’m doing fine. Do you want me to rub you?”

I was already rubbing myself, “It’s okay; I have it well in hand.”

Then she looked back at me. “I want you to fuck me, from behind. It feels so dirty that way. I don’t need more priming; I’m ready to go.”

The customer is always right. I grabbed her hips and entered her. The drive-train hump in the floor was between us, but she put her feet up on it and I had a good angle on her.

I was very fast and uninhibited in the way I banged her; I was still feeling emotionally voluble and I said, “Okay, Tiffany, now you’re going to get it but good.” She made lots of noise and it didn’t take her long to come. When she did, she was so loud that I imagined that, even with the windows closed, someone could hear it in Queens Plaza three blocks away.

Then I came, and I said her name over and over. I think I commented, without much originality, “You dirty lady, you don’t wear panties!”

We relaxed, and after a bit I pulled out of her. She looked back at me and said, “What are you smirking at?”

“Oh, I’m just looking at your pussy. I left a big creampie in it.”

She giggled, “Silly, that was the whole point of this.”

Then she surprised me by turning around and coming over to me. As we kneeled on the floor, she grabbed me and kissed me, passionately. I kissed back.

When she let go, my peripheral vision caught some movement outside. I looked out the back window and saw somebody loping down the sidewalk on our right side, the passenger side. Who is this fucking guy and what is he doing here? Tiffany and I hurried to get our clothes in some kind of order.

He was a tall black man, maybe in his forties. He wasn’t carrying anything and he didn’t seem to be in a hurry to get anywhere. He passed the right side of the car and kept going. When he reached the tracks, he made a left turn and walked along the right-of-way.

I said, “If he had arrived ten minutes earlier, even five minutes . . .”

“What could he do? He wouldn’t call the police.”

“No, but this is New York. People like to let their inner asshole run free. He could have knocked on the window, leered at us.”

“All right, it would be embarrassing but then he would go.”

“Speaking of which, that’s what we should do too – go.”

Sitting on the front seat, even with the generous General Motors padding, was painful but I was able to bear it. I wasn’t surprised when she got in the front with me. I got the car started and I turned it around and left Queens Street, heading for the 59th Street Bridge. Slow down, you move too fast; you’ve got to make the morning last. Actually, it was afternoon now.

She sat pressed up against me. We got to talking about music, and she brought up Vince Taylor, who was once considered the British Elvis Presley and was one of the influences on rockabilly music.

She said, “I like that song, ‘Brand New Cadillac.’ ” I was sort familiar with it; The Clash would cover it a few years later.

I asked her, “Do you like Dion and The Belmonts?”

“Yes; you must know their neighborhood.” Then she continued, “They got away with a lot in those days but they were subtle about it. How about ‘Runaround Sue’? We know what she was doing.”

“I was thinking of Buddy Holly with ‘Midnight Shift.’ “

“It was pretty obvious what ‘working’ late on that meant.”

Then she said, “You know what was an amazingly dirty song? ‘The Harlem Shuffle.’ ” I didn’t know it because the Rolling Stones hadn’t covered it yet. She described in for me, “It came out in 1963 by these two guys named Bob and Earl. It’s quite explicit in what it describes. The lovers are on the floor, and she’s on top of him.”

“I’ll have to check up on that one.”

She was actually charming me now. The talk came around to more sex. She said, “I do have an English schoolgirl outfit.”

“What does that look like?”

“You probably do know. They wore neckties, jackets, straw hats, that kind of thing.”

“Knee socks too?”

“They did, white or black or maybe gray. Plus, regulation knickers.”

I didn’t know what that meant, so she explained it for me. “In each school, all the girls had to wear identical underpants. They would be green or blue or white or whatever. And if they were caught with something else on, the headmistress would introduce them to the cane.”

That seemed intriguing, so I asked, “Would you wear this outfit for me?”

“Of course, and maybe I’ll be naughty and wear non-standard knickers.”

I tried to imagine what she would come up with. Then I said, “But I’m, you know, male.”

“We can stretch it a bit and say that as a teacher you could discipline wayward girls.” I knew Tiffany would have the equipment needed for this scene.

I suggested we go for lunch and coffee in Manhattan. When we got there, I wanted to ask her more about what Holly had said about me, but I decided against it. I did imply some knowledge about Holly. “What is it with you ladies and the crotchless garters or girdles and no panties?”

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