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[This role-play is part of the Charlotte’s Sexy Web series, but I gave it a separate name. Another of those is here.
Charlotte De Havilland is a perennial student who is finally getting her bachelor’s degree at the age of twenty-seven (she started at the University of Connecticut in 1967 and is finishing at City College of New York). The narrator, her boyfriend, is another student at CCNY who is approaching the age of twenty-one at the time of the story
Michelle is mentioned by not depicted here; she in other stories such as the one here.]
It wasn’t until April 1976 that Charlotte and I got around to performing her long-proposed naughty rich lady with her chauffeur role-play game. To do that correctly we would need a car, which neither of us owned. We considered renting one but we had an alternative to consider first.
She asked me, “Why don’t you use your dad’s car? I know you borrow that one quite a bit.”
He worked overnight and usually drove back by nine in the morning. That, however, had some difficult implications.
I told her, “You know I can only use it during the day, and believe me, fooling around in a car during daytime is a lot more difficult than after dark. I’ll have to scout out some locations first.”
That week I borrowed it for a few hours of on-site research. I had to find something within reach of Charlotte’s apartment in the Chelsea section of Manhattan and yet it had to be secluded during the day.
I started in my home borough of the Bronx and drove first to the Bronx Terminal Market. The produce wholesalers there were usually finished with their work by three in the afternoon, which gave us a tight schedule to deal with. I drove across the borough to the Hunts Point section which had a lot of warehouses, wrecking yards and other small businesses of that sort. There were a fair number pedestrians on the streets and I didn’t see anything promising.
This is like looking for a location for a movie shoot, I thought, and that gave me an inspiration. I remembered a place from a 1972 police thriller called The Seven-Ups. The final shoot-out had been filmed in the north Bronx adjacent to Amtrak’s Northeast Corridor. I had been there once on foot to check out the scene and I knew that it had access from a public road, Pelham Parkway.
I drove up there and found a wide-open gate. On the other side was a deserted area with a few small dilapidated buildings near the tracks. After I turned right and drove a short distance I found some bushes that partially hid the car.
I got out and stood around there for a few minutes pondering the location. To the north was a drawbridge across the Hutchinson River, to the west was a large housing development called Co-op City. It appeared that the apartment windows were too far away for anybody to see into the car if they even noticed it at all.
While I was there two passenger trains went by, one in each direction. They seemed to be moving too fast for anyone on board to see anything. I remembered a scene from the movie, right at this spot, where Roy Scheider appeared to do his own stunt. His detective character dashed across the tracks in the last moments before an oncoming train speeds through.
What Charlotte and I were going to do wasn’t completely risk-free, but it seemed like things were in our favor. We didn’t need all day, just an hour at most without interference. Americans, I thought, don’t just go to the poorhouse in an automobile, they turn them into boudoirs too.
The next day I reported back to Charlotte as we sat in the Finley Hall cafeteria. She did have some memory of the place from her own train trips, but she accepted my conclusions from my detailed reconnaissance. Then we talked a bit about the characters and the game we were going to play.
She was going to be somebody named Mrs. Ruxton. I asked her, “How old is she supposed to be?”
“You can’t ask a lady her age, you know that.”
“Come on Charlotte, we’re taking about your character.”
She thought about it for a moment, “Okay, let’s make her about thirty-eight, thirty-nine?” That would be eleven or twelve years older than she really was. “And she’s definitely divorced.”
As Mrs. Ruxton lived in Manhattan, Charlotte figured that she didn’t own a car; rather she called a limousine service whenever she didn’t take a taxi. I would basically be playing myself, except I worked part-time as a driver for this company while I went to college. I had become her favorite, thus now she asked for me each time she booked a rental.
It seemed like a workable plan. I would drive down to Chelsea to pick her up, then she would have some pretext for being driven in a northeasterly direction. We would have about forty-five minutes for conversation on the way there and probably about the same amount of time, I hoped, for trackside fun and games.
Driving Miss Entwistle
On a sunny Tuesday the following week I was parked at a hydrant outside Charlotte’s building. bostancı escort Perhaps Mrs. Ruxton was a bit eccentric to be living in a third-floor walkup, although since we were just playing “let’s pretend” maybe I was supposed to imagine this modest place as a luxury building complete with doorman.
I knew we were doing a let’s pretend with my dad’s car. Although nearly as big as Cadillac or Lincoln, what I had really brought downtown was a dark green 1968 Pontiac Bonneville. When he had gotten it as a used vehicle it still had rear fender skirts, but over the years rust had destroyed the brackets holding them in place and now the wheels were uncovered.
My only concession to looking like a professional driver was to wear my usual blue sport coat plus a tie. After I parked I stood outside on the passenger’s side, the side facing the curb.
My “customer” came out at the appointed time and walked down her stoop. Most of her outfit seemed to be familiar parts of Charlotte’s wardrobe: a tight green skirt, green and white blouse, a light-gray blazer, and white heels. She had her usual Louise Brooks hairstyle and her dark-rimmed glasses. The only item I didn’t recognize was her white hat. What do they call that style, a cloche?
She spoke first, “Hello Paul, how are you on this lovely day?”
“I’m fine, Mrs. Ruxton, I’m so glad you decided to use Lioness Limo again.”
The Lioness Limo name was an inspiration that had come to me while I was waiting for her.
She replied, “There’s a reason I always use Lioness, which I will tell you about in a moment. Oh, do you like my hat? I think it makes me look like Audrey Hepburn.”
“Yes, it’s a really – ah, nice hat.” Although she had dark hair and was only slightly above Hepburn’s five foot seven, Charlotte never reminded me her. There was no impression of delicacy about her and she seemed somehow taller than her actual height. She reminded me a little of Jackie Onassis now, an image I had gotten from her before. When I really wanted to flatter her I would bring up Cyd Charisse.
“And I know it’s not Memorial Day yet, but I decided to break the rule and wear white shoes today.”
I had never heard that bit about shoe colors. “Well, I won’t tell anyone if you don’t.”
She said, “Anyway, I’m dressed in my ensemble to be out and about this spring day. I’m ready to go!”
She approached and I opened the rear passenger side door for her. There was a substantial dent in it, the result of my dad sideswiping a parking garage pillar, but she took no notice of it. I got in behind the wheel and started the engine. The back seat of this car was rather low and her skirt had ridden up when she sat down. As she crossed her legs I could hear the sound of her stockings rubbing together.
“So, Mrs. Ruxton, where would you like to go today?”
“Oh please, we’re practically friends, isn’t this the fourth time you’ve driven me?” We hadn’t discussed that detail of the story but it seemed plausible. “I’d like you to call me by my first name, which is Olive.”
I don’t think I had ever known an Olive before, “Yes ma’am, I’ll do that.”
“And that word ma’am too, it’s just so formal. Makes me feel matronly in fact.”
“All right Olive, then what is your destination please?”
“Well, I have a few small errands to do, but since it’s such a lovely day, I’d like to just go for a drive for a while. Say, to southern Connecticut.” That was well thought-out, because I-95 in that direction passed right by our train yard trysting place.
“Of course, let’s go.” I drove down the street and waited to turn onto Seventh Avenue.
“I was going to say, I always ask now for you when I call the company. You’re my favorite driver. In fact, if you’re not available on a certain day, I consider changing the reservation.”
That seemed oddly flattering. I liked being appreciated for this let’s-pretend job. As I started around the block to get to the West Side Highway, she asked me, “Do you mind if I smoke?”
“It’s no problem, go ahead.”
I had never known Charlotte to smoke before so I wondered what she was going to do. She pulled out a cigarette holder from her purse and then planted a doobie in it. So that was it; she did smoke pot on occasion, although she was hardly a burnout case.
“Excuse me ma’am, I mean miss. . .”
“It’s Olive, remember?”
“Yes, Olive, that might not be such a good idea if we get stopped.”
“I know Paul, but you’re such a careful driver, the odds of that of infinitesimal.”
I was glad she appreciated my driving skill, but there was a fourteenth Murphy’s Law of driving and drugs. If you only had pot in a car once out of thousand times, that would be the time you got pulled over by the police. I wished I had checked the tail lights and turn signals that morning. Still, it was novelty to see a cigarette holder being used that way.
On the way over to the highway she was telling me about herself. “Now my ex-husband, Mr. Ruxton, a Mister ümraniye escort bayan Clarence Ruxton, you know what I say about him? ‘I didn’t marry him for his money, I divorced him for it.’ “
I chuckled at that quip because I had never heard it before, although it was one of those standard jokes that go around. She continued, “I’m thinking of going back to my maiden name, which is Entwistle. Now the Entwistles were not upper class, merely upper-middle.” I had heard Charlotte discuss the American class system before. “My father was an anthropology professor at Yale.”
Charlotte’s dad was actually a lawyer but that was close enough. I noted that she was only taking a few puffs on her joint; it was probably a good thing she was going to moderate her use of it today. We were now heading north on Twelfth Avenue under the rusting hulk of the abandoned elevated highway.
“The Ruxtons were old money, big money. They made their fortune in anthracite coal in Pennsylvania, and from one of the railroads that hauled it. You’ve heard of the Delaware, Lackawanna and Western?”
“Yes I have.”
“They advertised themselves as the route of Phoebe Snow. Their jingle went like this:”
“Said Phoebe Snow,
About to go,
On her way to Buffalo,
My dress stays white,
From noon to night,
Upon the route of anthracite”
This was all familiar; I had talked to Charlotte a long time ago about how the singer Phoebe Snow had been inspired to name herself after seeing old boxcars in New Jersey.
We went up a ramp onto an intact portion of the highway and emerged into the sunlight. She said, “Excuse me, I have to put on my sunglasses.” Then, “I’m sorry, I’ve been talking only about myself. I’d like to know more about you. You’re such a hardworking young man, putting yourself through college this way.”
It was strange to hear myself described as “hardworking.” That may have been true for schoolwork, but not so much for paid jobs.
She asked, “What is like at CCNY?”
“We’ll be able to see it from the highway in a few minutes.” That seemed irrelevant but Olive didn’t notice the non sequitur. Instead she asked me, “I imagine you have some girlfriends up there.”
I had to decide how to play that. “There were a few, but none since last November.” That was true except for Charlotte herself of course. I glanced over to my left at the sunlight sparkling on the Hudson River. It was indeed a pleasant day, a good day to bang an older lady in this roomy car – if we got away with it.
Olive didn’t have a follow-up but rambled on about other topics, like how it was that the “ethnics” – presumably including Italian-German-Irish me – had built America. She also declared that the Kennedys were “vulgar,” including that “odious Ted.” “What he did with that girl at Chappaquiddick was just inexcusable.”
She went on, “I don’t care if they have their compound on Cape Cod, they just seem trashy to me.” That must have been Olive’s opinion, because I never heard Charlotte complain about the clan. Meanwhile, I pointed to the City College science building visible on the hill to the right.
“God, what a hideous building,” she exclaimed.
We were on the ramp up to the Cross-Bronx Expressway when Olive decided to capitalize on her earlier query, “Paul, do you mind if I ask you a personal question?” She didn’t wait for me to respond. “I was thinking, it must be hard for a healthy young man such as yourself to go without a girlfriend for so long.”
How would my limo-driving alter ego respond to this? I decided to say silent for the moment.
She said, “I know about loneliness myself, although God-knows, Chuck – that was Clarence – was nothing to write home about.”
We entered a noisy section of the expressway, “under the apartments” as the traffic reporters called it, which was like being in a tunnel. When we came out a minute later she asked, “Do you ever think about me when I’m not around?”
“What do you mean, Olive?”
“I mean do you think of me at night, when you’re in bed.” I let that pass, and she continued, “Because I sometimes think of you, of being with you right here in this car.”
The real me was getting turned on by her comments. Part of my mind was admiring the great way Charlotte was playing this. She had the acting and directing skills to create the scene that was developing.
She rubbed the surface of the seat next to her. “I love the smell of leather, it’s so sexy.” It was actually black vinyl, and the Pontiac had that musty old car smell that I didn’t find unpleasant. She then asked me, “Do you like my stockings?” I knew enough to say yes, which was certainly true. Anyway, Charlotte rarely fished for compliments.
She said, “These are not pantyhose you know. On a day like this, I like to wear garters with belts. It makes me feel – hot, sensual. Here, take a look.”
I took a glance back. She had hiked up her skirt and spread her legs. I could see everything she had mentioned, the white garters, kartal escort the belts, all the way to her white-panty covered crotch.
The traffic was sluggish in this stretch – it wasn’t bumper to bumper, but we had slowed to less than twenty-miles per hour. I used the mirror to look at her again. She had pushed her sunglasses up and she was smiling at me. Her cigarette holder and joint had been put away, which seemed like a good idea at this point.
A few moments later Olive’s hand appeared over my right shoulder holding her panties. These were basic white briefs. “Here, have a sniff, although I did put them on fresh this morning.” She was right behind me, leaning on the back of the seat.
I figured that I should follow all reasonable client requests, so I put her drawers to my nose and caught a faint whiff of her aroma. Then I carefully placed them on the seat next to me. By now we were moving down the middle lane at about ten to fifteen-miles per hour. The car was hemmed in by tractor-trailers left, right and to the rear.
“You don’t mind if I play with myself, do you?” I don’t know why she asked, because she had already leaned back and gotten started. Her feet where up on the seat and she had both hands working on herself. As a chauffeur, I didn’t know how to handle this situation. I didn’t want to appear indifferent, but neither did I want to seem overeager.
A moment later she had taken a hair brush out of her purse and she was moving the handle in and out of herself.
“Ah, Olive, I was wondering if any of these truckers might see you.” That was not a worry I had to make up.
“Oh, let them look if they want. It will give them something to jerk off about at the next rest stop.”
From my position I couldn’t see into the cabs of the trucks on either side of us. I guessed the guy behind us might blow his air horn if he noticed what was happening. Maybe Olive should order a car with tinted windows next time. Meanwhile she remained talkative through the early stages of her self-pleasuring.
“We’re such puritanical society when it comes to masturbation I would say. Everybody does it but no one talks about it. Self-abuse, what a strange term. Anyway. . .”
She took a moment to think, “You’re such a nice young man, and I know you haven’t any poon in some time now.” I was always pleased when one of Charlotte’s characters, women in their thirties or forties, called me “young man.” It accentuated the real six-year age difference between us.
She went on, “You’ve always been so polite, you never made a pass at me even though I wished you would.” I hadn’t realized what an exemplary employee I had been. “However, I bet you have a big erection right now.”
Even if I was on the job I owed her some male honesty, “Olive, that is an understatement.”
She laughed, “Don’t worry, I can take care of that. I’ve got some moves that those coed snips don’t know about.”
That must have been a swipe from Charlotte at my now departed girlfriend Michelle. Despite all our talk about open relationships jealousy did surface at times and she still had some resentment against her now-departed younger rival. In any case, that was all moot now. I glanced back again to see exactly what moves she did had. One of her hands worked the hair brush while the fingers of the other circled her clitoris. She stopped long enough to blow an air kiss towards me.
Where were we now? I noted we were leaving the trestle over the central Bronx and entering another of the open cuts. Thousands of people had been displaced from their apartments to build these six lanes; Charlotte and I had talked about that before.
She said, “I’m not one of those ladies who uses vibrators; I can do just fine with my trusty brush and my own nimble fingers.” I was wondering how long Olive had gone without getting any poon of her own. “How about you?” she asked. “Who do think about when you stroke yourself? Maybe old girlfriends, or maybe me sometimes?”
I evaded the question, “Well, various people. Porn sometimes, I admit that.”
“That’s completely understandable,” and she giggled. “You could call it porn-tang! Anyway, I hope I’m not distracting you too much,” she said.
I did my best impression of a nonplussed employee, “It’s fine, think nothing of it.”
“You’re an excellent driver. Not many of them could deal with their customers so well.”
Then she said, “I have a serious issue for you.” She paused before going on, “Maybe you do want me, for real? I would very much like it if you were with me. Today would be great if you can find the time.”
I glanced back at her. Her expression was hard to decipher, but I caught a bit of concern in it as if she was worried I might reject her. Like a couple of other women I knew, Charlotte was an impressive actor in role-plays. Olive Ruxton was fully there in my back seat.
“Yes Olive, I would like to be with you too.”
Then Olive was preoccupied with touching herself. I knew from witnessing this before that she could come in about ten minutes if she was in the mood, and she definitely seemed that way today. At the rate we were traveling we would have plenty of time before we reached the Pelham Parkway exit. If need be, I could always bypass it and make a U-turn later.
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