Oral rough and trucking
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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-seven-year-old divorcée who started asking for my services every Sunday in the late spring of 1976. For the first two sessions she decided to mix kinky BDSM 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 getting 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 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 reasonable 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, this is your trip.” I deliberately avoided 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 word is as safe as J.P. Morgan’s bonds.” 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 this narrative. I had 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.
“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, do 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.” Rather hackneyed dialogue, I thought. I was sure this was not Holly's first time being whacked as somebody's bottom girl. I was just glad that it was my turn now.
She sat on my right side, “All right,” I said, “Let’s not take all day with this.”
She had an unexpected question, “Should I keep my hat on?”
I didn’t have to think for long, “Yes, Holly, let’s do it that way.” She kept her white gloves on too.
It had been a while - nearly a year - since I had spanked a girl, but I remembered how to do it. I said, “Now Mrs. Sykes, place yourself over my lap and pull your skirt up.”
She put herself there and I liked the feeling of solidity as her body pressed against me. I had a surprise as she reached back and yanked her skirt up. Her tan stockings were being held up with a garter belt and straps. The garter was generously proportioned and it was sort of like a crotchless girdle. A sheer pair of tight white panties covered this. Everything in fact was white except for the straps, which were yellow.
“Wow, Holly, you have a nice retro look going.” It certainly was different from the pantyhose that had become ubiquitous.
“I like wearing this kind of thing in warmer weather. I like the feeling of the hot air coming off the sidewalk and rising up around my hips and crotch. It makes me feel - sexy and powerful.” She looked back at me and smiled, “Sometimes I just wear a garter-girdle without panties. Or I have a skirt or dress and no underwear.”
“Why don’t you do this more often for me?”
“I promise I will; this is only like our third meeting.”
“Anyway, are you ready for this?”
“As ready as I’ll ever be.”
I yanked her underpants down below her knees and looked her over. Her buttocks were larger than I had expected. Some middle-aged spread, I thought, ungenerously. The skin of her ass and thighs had a nice creaminess. I knew they’d look quite different in a few minutes
I pushed down on her back with my left hand and then I held her around the waist.
“Listen honey,” I said. “Raise your behind up more.”
She pushed with her white shoes against the floor and raised her backside further. Rather than wait any longer, I raised my right hand and gave her a big smack on her right check. She said, “Oh my God,” and I saw the red hand print I had left on her. I had decided she didn’t need a warm up, and I continued to hit each cheek in turn.
She moaned and grunted a lot. At one point she said, “I do know that I deserve every bit of this.”
“Well, Mrs. Sykes, you’ve been a very naughty lady. We’ve got to be sure it never happens again.”
I hit the back of her thighs sometimes for variety. Within a short time her skin was reddening quite noticeably. She started to move around, pushing with her shoes on the floor. She also started to bounce up and down more. At one point she whipped her head around and her hat came off and landed on the seat.
I noticed some changes in myself. My spanking hand was getting quite warm and more than a little sore. I had rarely used the technique of using both hands. But the most dramatic item was the huge erection I developed, which always happened in one of these sessions. I was sure she could feel it poking up inside my pants.
She was breathing heavily now and her whole body moved in tandem with my blows.
“How much longer is this going to go on?” She asked.
“As long as I think necessary.”
Her redness deepened in spots within the ovals I had made on her buttocks. “You’re bruising me, I think,” she said, which was probably accurate. I then saw something that gave me a cue as to what to do next. Her hindquarters were up and I could clearly see her cunt. She was very wet and glistening down there. As I spanked, more creamy stuff started to appear there.
“You depraved lady, you're getting turned on by this, aren’t you?”
“I can’t help it; it always happens this way.”
Shortly after that I decided to stop, and I briefly rubbed her blazing ass. She moaned and I knew she liked that.
“Would you like to rub your own behind, comfort yourself a little?”
“Oh yes, it feels like it’s going to fall off.”
She reached back and grasped her own buttocks. She looked back and said, “Man, you really did a job on me.”
“That’s what you wanted, and that’s what you got.”
Then I decided to finger-fuck her, which went very well indeed. I had heard of girls who could climax from just the spanking but usually it required somewhat more than that. I put my right hand into her and used one finger on her clitoris while the others probed her vagina. It didn’t take long for her to reach orgasm.
“You’re making me come!” she said, which was a redundant statement but I liked hearing it anyway. She raised her hindquarters higher and used her gloved hands to push against the seat cushion. The sound she made was a caterwauling that was not intelligible.
Then she collapsed on me and simply breathed without saying anything. I rubbed her bottom for a short while and got into a pensive mood. As I stroked her cheeks I said, “Anyway, it’s time for you to get the belt.”
“Oh no, I’ve already taken my discipline.”
“And you liked it way too much. Don't worry, I’ll be merciful. Six of the best and that’s it.” How did the English invent these ridiculous expressions?
“Get over the jump seat.” The jump seats were two folding chairs in the back so a total of five people could fit in that area. Today they would violate every safety regulation but Checker was allowed to keep them until it went out of business in 1982.
“Okay, I’ll do it.” She got up and opened one of the seats; then she planted herself across it. Briefly I felt sorry for her; it wasn’t entirely nice to whip such a well-rounded behind. But BDSM wasn’t for the most part about being "nice.”
I pulled her panties from her ankles and left them on the floor. Then I took my belt off and gave her a hard swipe across both cheeks. She yelled something and banged her white high heels against the floor. Now she had an even stripe across the earlier damage. Then I remembered the enthusiastic ways she had used her hairbrush and whip on my poor ass. I decided she could take five more.
She cried out with each stroke. Then she briefly hung there quietly except that she was breathing heavily.
“I think you’ve made up for your mistakes and indiscretions.”
She surprised me by rolling onto the back seat and lying there face up. She used her gloved hands to cover her pussy, which would have been visible with her crotchless undergarment.
She looked at me and said, “Don’t think you have the right to just fuck me now.” I didn’t know if she was bluffing, so I said, “I never thought that was guaranteed. But let me show you something that you should consider” .
I was kneeling on the floor; I undid my pants and let my erect cock spring out. “Maybe you should think about this”
She smiled at me; I thought that I might simply get, like last week, a blowjob out this. But she took her hands away from her crotch and said, “That’s a nice big cock. All right, go ahead, put it in me, fuck me.”
This was a very abrupt and direct coupling. I got on top of her and she spread her legs wide. One of her feet rested on the top of the back cushion. I just pumped into her as quickly and deeply as I could. I made a noise with each thrust and she whispered a few words of encouragement. I thought to myself, you’re finally going all the way with Mrs. Holly Sykes.
She didn’t come this time, but it didn’t take me very long. I arched my back and chanted, “Holly, Holly,” as I ejaculated into her. Then I lay on top of her
Within a few moments I had the discomfiting thoughts that always came after car sex or any sex in unusual places like rest rooms. It was: what am I doing here - my pants are down - and what have I just done? Maybe I was a conventional kind of guy who preferred sex inside residences.
Holly was looking up at the ceiling, not at me. I couldn’t stand the unease I felt so I uncoupled from her and sat up. She did the same. I guessed she wanted some affectionate contact so I put my arm around the bare shoulders and pulled her closer. She seemed to like that; she kissed me on the mouth.
Then we both seemed at a loss as to what to do next. I stared through the windshield at the back of the truck in front of us. A sign on the back door said Lentz Trucking. My irrelevant comment was, “I used to know someone in high school named Lentz, Margery Lentz.”
“I wonder if it’s a relative?”
“Probably not.” Then I let out a loud, somewhat overly-dramatic sigh.
“What’s the matter?”
I knew exactly what was bothering me. “We’ve never been on a real date.” I had been to a bar with her for a short time, and I had a late lunch in her apartment the week before. I had been disappointed when she had dismissed me both times.
She said, “How about what we’ve been doing? Aren’t those dates?”
“Not really. We don’t actually go anywhere not connected with a trip in a Lioness Limousine.”
She contemplated that for a moment. “You really are a romantic sort, which is sort of endearing. Maybe we could go somewhere right now. It’s only one o’clock.”
I did have an inspiration. “Have you ever been to The Cloisters? It’s not a long ride from here.” The Cloisters was a museum of Medieval art maintained by the Metropolitan Museum of Art.
“That would be great. I haven’t been there in at least six years.” That was about the same for me.
I looked at her high-heeled shoes and said, “You’re not going to be comfortable walking around in those.”
“Not to worry; I have a pair of sandals in my bag.” And indeed she did, sturdy looking ones with thick soles.
She got in the front with me and we drove off and left the trucks that had provided us with such excellent protection for our escapade. It wasn’t the first time these admirable lorries had done this; they have provided similar privacy for our first stunt in Brooklyn. And I had parked with various girls in cars over the years and trucks parked on commercial streets had given us some cover there too.
As we drove out of the lot I asked here, “Aren’t you going to put your panties back on?” I already knew the answer but I wanted to hear her explain it.
She was in her talkative, frisky post-sexual - actually now it was truly post-coital - mood.
“I’ve never told you that I like being out and about without panties.”
“You mentioned it a little while ago.”
“Yes, sometimes I’m wearing a garter-girdle like now, but as I said, sometimes I have a skirt or dress with nothing underneath. After a few minutes out I get so turned on that I can hardly stand it. My pussy gets so wet it’s virtually dripping.”
“Why don’t you do this for me some time?”
“I am, sweetie, right now.” It seemed that I had known her longer than a few weeks. She continued, “Sometimes I sit on a park bench and imagine what men would think if they knew what I was doing. Sometimes I imagine that someone, maybe a cop, will discover my lack of underwear and spank me right there on the bench where everyone could see me. That would be both so shameful and so delightful at the same time.”
“Do you ever flash guys?”
“I guess I’m too cautious. I cross my legs and push them together so that my cunt is compressed.”
“Do you ever have an orgasm that way?”
“No, but when I get home I masturbate like crazy. The first time, the merest few flicks of my clit and I go off.”
I was getting erect again just imagining this. Today we really should go to her apartment later for that proper fucking she had mentioned before. She seemed to still be chatty, so I asked her a question. “Why do some girls like being spanked so much?” Not all of them of course, but those that did were often wild for it.
To my surprise she had an answer, “Because being hit on the buttocks causes blood to flow into that area, and it makes the genitals tingle. That is particularly true of the vulva and vagina, which are more exposed in that position.”
It was such a clinical explanation and yet I was impressed. “Thank you, Professor Sykes; you really know your subject.”
We drove west and then north under the abandoned hulk of the elevated West Side Highway. Then we were up on the Henry Hudson Parkway. It was a splendid late spring day and the sun shone on the Hudson River. Holly sat close to me and had an arm around my shoulders. This was usual when we were leaving the scene of one of our indiscretions.
Now she commented on our vehicle, “This is certainly a strange car.”
“Yeah, it’s sort of primitive I’d say, like a Russian truck. But the view from the driver’s seat is great.”
In another mile or so I said, “There’s City College up there” and I pointed up the hill on the right side. The only building visible was the modern but ugly Science Building. “Have you ever been there?"
She replied, “Not in years; I’ve heard it's pretty shabby now.”
“That’s mostly true, but it’s still my school. The Harvard of the Proletariat is what it used to be nicknamed. You don’t necessarily need a fancy campus.”
I thought more about it, “Actually, the South Campus, which used to be Manhattanville College, is sort of bucolic.” And it was doomed too; there were long term plans to demolish it, but it would take years to finally do that and replace it.
We reached the museum which was located on one of the highest points in Manhattan. We especially like the various courtyards, or “cloisters,” which had been built with architectural features salvaged from old or damaged European buildings.
Afterwards we bought ice-cream sticks and strolled around the grounds. We stood leaning on a wall and we looked up and down the length of the river from Jersey City to the Tappan Zee Bridge. For some reason the topic of Henry Hudson came up; he was the first European to sail all the way up the river. Holly pondered that and asked, “I wonder if he said anything significant about it.”
It was quite impressive where we were; the high cliffs of The Palisades were on the opposite shore. I vaguely remembered a quote and I repeated it, “One cannot fly like an eagle with the wings of a wren.”
Actually, I had screwed up and I had quoted somebody from the 19th Century with a similar name to Hudson's. I didn’t mean to, but Holly seemed to like it anyway.
I thought more about her as we stood there holding hands across the top of the wall. The afternoon sun shone on our faces. She looks even more attractive out here in the open. Previously I had mostly seen her in vehicles and buildings. Plus, she had the advantage of not wearing panties; they were stowed somewhere in her white bag.
Meanwhile, she had forgotten all about her fictional financial problems. I gave her a pat on her fanny. “Hey, be careful, it’s a little sore down there.”
I almost apologized but I didn’t. “You took it all pretty well. By the way . . .”
She noticed my hesitation. “Yes, what is it?”
"I’d like to come down to your apartment later today and have something more than potato salad like I did last week. And I do love your retro look with the garter and straps.”
“All right, I see where your mind is at. And yes, sometimes the older ways were better. And you'll definitely be seeing more of it this summer.”
“You know our relationship is different now.” I was going to say we had fully consummated it. Instead I said, “I’d say we busted its cherry but good.”
She laughed at that, “Relationships don’t have cherries to bust - although, okay, I get it. You must really want to fly like an eagle.”
“ 'Fly like an eagle, let my spirit carry me.' ” The song had only been released a couple of weeks earlier. I put my arms out and started to flap them.
“I’ve got all my feathers in and I’m ready to go.”
########
The bit about being “as safe as J.P. Morgan’s bonds” is from the novel The Day of the Locust.
Dani
- 08.01.2022
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- Spanking
