This is a sequel to
Queen of Diamonds.
While driving for an outfit in New York called Lioness Limousine, I had a customer who was both delightful and exasperating at the same time. Holly Sykes was a thirty-eight-year-old divorcΓ©e who started asking for my services every Sunday in the last spring of 1976.
For the first two sessions she decided to mix kinky BSDM activities with various sexual acts - in the car. On the first outing, she took me to the back seat where she paddled me with a hairbrush on my trousers and then on my bare behind. Then she had me go down on her; after that I masturbated as she watched.
On the second journey she whipped me with a leather implement called a quirt. Like before, this was in the back seat and on my bare buttocks. Then we had oral sex: I licked her cunt again and she mixed things up a bit by giving me a very satisfying blowjob.
These had to happen in fairly isolated areas during the middle of the day. The first time she picked a warehouse district in Brooklyn while on the second excursion I found an abandoned train yard in the Bronx. Yet it was still a bit exciting or nerve-racking thinking about get caught. We obviously had to get things done quickly and not indulge in leisurely love-making sessions.
That actually was the main reason I found Holly annoying to some degree. She only saw me in the car once per week while I was acting, technically, as her employee. She saw me briefly in a restaurant and in her apartment, but our dating situation was rather limited.
Also, being twenty-one and lacking a girlfriend, I was eager to actually consummate our relationship and get my cock into her pussy. Instead, she ran our relationship as she so saw fit. I was developing affection, maybe even love, for her and I resented being treated as a sort of gigolo. I had never considered myself as gigolo material, but yet I was cast in this narrow role. It was galling to consider being used by her and then forgotten, apparently, for the other six days of the week.
On the third Sunday I made my usual drive to East 21st Street in the Gramercy Park neighborhood of Manhattan. This time she didn't wait for the doorman of her building. She came directly to the passenger-side rear door and got in. For some reason I didn't know yet, she had requested one of the few Checker cars in our fleet. Checkers were usually taxi cabs, but a few were also owned by car services and private owners who used them as their personal cars.
I actually liked the brand. In that pre-SUV era they were the tallest passenger vehicles on the road; the basic design hadn't changed since 1954. If they were maintained properly - and many yellow taxis weren't - they were a reasonably competent car to drive.
When Holly got in I forgot about the vehicle and concentrated on her. She was a tall, shapely woman with dark blonde hair. Every time I saw her she was well-dressed; no weekend sloppiness for her. Today she had a sleeveless blouse with a matching, fairly tight skirt. These were blue with a white dotted pattern. She had a straw hat, a white bag, white gloves, white high-heels and tan stockings. As usual she looked great.
This time when she got in I didn't use the tongue-in-cheek "Good morning, Mrs. Sykes" routine from previous weeks. I just said, "Hello Holly, what's up? Where are we going?"
I immediately sensed her tension. She said, "Just drive down the block; I'm not sure where we should go."
I put the car in gear and drove off. "How about we just cruise around Manhattan a bit while you think about it."
"That's fine Paul; wherever you think best." She immediately launched into, "I have something - an issue that is really bothering me."
Knowing her as well as I now did, I assumed that this was a pretext for something else - something sexual I hoped and assumed. She wasn't going to welch out on me this week - probably - although I was getting to know her unpredictableness.
I put on an air of calm and relaxation, "How about we play the radio? You know, it might make you feel better."
"That would be - okay, if you wish."
"If it's okay with me? My dear, you're paying for this trip." I deliberately avoid getting too intimate with her by calling her sweetie or baby, although I had used those terms with her before. It seemed a bit early in the trip to be using them. I flipped the switch and the radio came on in the middle of the Eagles "Desperado."
"Hey Holly, we heard this last week. You even sang along."
She hesitated for a moment, "I really don't feel like singing."
"You were very good at it, remember?"
I didn't get anywhere with my complement. She had something more pressing on her mind.
"So Holly, talk to me then."
Or give me another blowjob soon.
That would be good, although I wanted more than that from her. I would have to find a suitable - and relatively secure location - for that kind of thing.
"Paul, can I trust you with some personal information?" At this point we were still aimlessly moving down 27th Street. We were almost at Eighth Avenue.
"Of course, you know me." For some reason I said a phrase that went, approximately, "My bonds are as safe as J.P. Morgan's." I couldn't place it, but perhaps it had been in an old movie.
I didn't bring this up with Holly, but some intuition told me that money would be involved in her affairs. I guessed correctly.
"This is very hard for me to admit," she said. "I have had some financial setbacks."
"Okay, so . . ."
"The fact is that I've not been able to pay some of my bills, including what I owe to Lioness Limo. Actually, I'm in arrears to them right now."
I knew this had to be part of some piece of fiction she had cooked up for me. She had never been behind in her payments. Even as a mere driver, I would have heard about that. I was aware that the company did not extend credit to anyone. And in any case, I knew enough about her finances to understand that she was not short of money.
At first I thought:
what is my role in this narrative supposed to be?
I obviously didn't have money to lend her, and even if she did have a debt, I had no influence over the company or its policies. I decided to play it straight and see what her game was. I already understood it would have something to do with me.
"Gee Holly, that's too bad. Is there anything I could do?"
"Well, obviously for somebody like me, it's the guilt that is most troubling. I'm not used to being - call it a deadbeat. It goes against my upbringing and character."
I thought,
welcome to the real world, Holly, where we proles dwell and struggle with money.
Also, I was getting a bit impatient; it was taking too long for her scenario to be revealed.
"As I said, what do you want from me? Or do you just want. . ." I almost said,
do you just want to vent?
That seemed a bit harsh and abrupt. Instead I said, "Do you just want a sympathetic person to listen to your problems?"
She was actually wringing her white gloved hands while she sat in the back. She was a pretty good actress, but she was being a bit melodramatic today.
"It would be good if you could help me expiate my negative feelings." Nice big word she used there. "In other words, you should punish me for my misdeeds.
Now it was starting to come together, although I thought this narrative was a little clumsy by the standards of her previous ones. It was an inversion of her earlier complaints that I was the miscreant who needed the punishment.
I stayed calm and collected and decided not to say anything. I had driven in a big circle and now I was heading east through Chelsea to what would later be called the Flatiron District. I didn't have to wait long.
She said, "What I really need is a good, sound spanking to show me the error of my ways."
This all wasn't too surprising as I already had seen her kinky side in action, although previously she had only used it on me. I played a question and answer game with her.
"You mean you want to be beaten on your backside?"
"Yes, of course."
"Should it be on your bare behind?
"Absolutely, that's the only way it could be effective. You could take me over your knee and use your hand on me. I mean good and hard, uninhibited. Then you should consider an implement, like your belt of maybe a shoe.
This was a lot of information to process. I looked back at my mature but attractive passenger and I was aware of the impact she was having on me. I already felt sexual excitement at the prospect. The big question was, what else would I get out of it? She had always brought me to orgasm after punishing me. Well, technically, the first time I had brought myself to a climax while she watched and commented.
I had to close the deal. "Holly, based on your previous preferences, you want this to happen in this car, today I mean?"
"Yes, that would be best. There is plenty of room in the back for this." That explained her request for a Checker today
I thought about the logistics for a few moments and I said, "You know, instead of driving to some remote location in the outer boroughs, this could be done locally, somewhere near here."
"Really? How would that be done?"
"Let me look around, I'll show you."
In those days, before the real estate boom, a lot of smaller buildings in lower Mid-Manhattan had been demolished and the land lay fallow as parking lots. In a few minutes I found something suitable.
It was a narrow but deep parking lot with a number of trucks parked in it. It was surrounded by old loft buildings that I assumed were mostly unoccupied today. There was room to drive a car through and park in the back behind the trucks. It gave us as much privacy as we could hope for in this situation. And, as usual, we didn't need the whole day.
Holly seemed impressed after I had parked and turned off the engine, "This is really almost ideal."
"Let's hope our luck continues to hold out. Stay there, I'm coming back to you."
The Checker's back seat had a huge amount of legroom, and Holly's long legs would not be impeded by anything. I sat there and removed my jacket and rolled up my sleeve to show I meant business. Holly demonstrated no affection towards me, but I knew that could come later.
"Paul, I really appreciate what you are doing for me."
"Don't get too comfortable. I'm going to give you a long, hard thrashing." That word seemed like something lifted from British spanking porn. The English Vice, although it seemed more prevalent than I once imagined.
"It's going to hurt, isn't it?"
"It's supposed to hurt, that's why it's a spanking."