I know that this is going to sound rather unfair, but I want to be honest about some of my experiences. I’ve found it odd how a new relationship with a woman can vary so much in the way it gets started. I'm thirty-seven and have gone through a long marriage which was followed by a divorce. I had eight girlfriends before that.

Sometimes I pursue a certain woman for a while, and nothing happens. Often they are not honest about their real intentions and yet they dangle sex in front of me to keep me around for various reasons that I won’t go into here. I know they don't owe me anything, but I often feel that they are not being honest with me. I'm not a saint, and I don’t like being strung along by them.

Perhaps it’s just part of the modern dating and mating game, but this lack of honesty seems to have become more common recently. Sexual attitudes have changed a lot since I left college fifteen years earlier, and not for the better.

And, yes, I know that men have been playing their own tricks since the Cro-Magnon era or some such distant epoch. Some basic trust between the genders had lessened, and now everyone seemed poised to exploit everyone else. By 1992 I had become rather cynical about the whole dating scene

The reason I’m bringing up this topic is that there is another kind of woman. The odd thing is, I won’t even be trying to date them, much less screw them. They will be coming after me and making it clear that they are absolutely ready to go. And many of them are not looking for one-night or even one-week stands. That is fine with me because there is still some need for romance in my jaded soul.

I met one such woman in June 1992  after a long dry spell. It was at a highly unlikely place for romance to bloom: an auto-driving school. My role in that organization, The Supreme Driving School, was as one of the instructors. I don’t know why this lady picked me, but she knew what she wanted and she got it.

In addition to being divorced, I was also between my usual jobs in publishing. Driving instructor jobs have a high turnover rate because let’s face it, it’s not much fun trying to teach various nervous and incompetent people how to handle an automobile. Instruction in parallel parking was one of the more unpleasant tasks involved. But at least it was at a slow speed and relatively safe. And believe me, accidents involving driving students are not uncommon.

I found that the job was very easy to get. All I had to do was go out with another guy and drive around with him for about a half-hour. I also had to pass a written test like the DMV gives, and one has to be pretty dim not to ace that particular exam.

So I found myself out there trying to teach people how to handle a motor vehicle on the roads of America. I must have had some knack for the task because it was mostly a bearable job. All of our cars were 1991 Ford Taurus sedans. These weren’t the most compact cars available but they weren’t as bulbous as the next generation which had just been released the previous fall.

There was an extra brake pedal on my side – the passenger side – but no additional steering wheel. I had to lean over and grab the regular wheel more than once to avoid a crash. 

It was in such a blue Taurus that I met the woman, one of my students, who is the subject of this story. She was standing on the sidewalk in front of her house when I drove up. Her name was Meryl Reinhold and she was twenty-nine years old. Out of habit, I suppose, I made a quick assessment of her. She had the look of the girl next door who also happened to be a fairly big girl. She wasn’t really fat, but man was she round. I didn’t know how round until I saw her naked at a slightly later date.

Her reddish-brown hair was cut short so that it covered her ears although it was also rather messy. She had plastic-framed glasses. Perhaps her best facial feature was her toothy grin. She projected a genuine warmth with her smiles. Somehow I had a good feeling about her from the moment I met her.

We greeted each other and I slid over to let her in. She was wearing a white blouse which she had unbuttoned almost down to her waist. I tried to determine if she was wearing a bra or not. Considering the size of her breasts she certainly needed one. The rest of her clothes consisted of blue jeans and white sandals.

There is one more aspect of Meryl I should mention. She didn’t get very stoned, but she would take a few puffs of the evil weed before her lessons. She claimed that it helped calm her nerves. I caught a whiff of the drug when she first got in.

Smoking that stuff was a bad idea before driving lesions, but she seemed lucid enough and I didn’t call her on it that day. Probably I was just too passive to make a big deal on the issue. It certainly would have been within my job duties to do tell her not to smoke the stuff. I wish I could say that her use of marijuana helped me get into her pants by our third lesson, but she was completely straight on that day.

Meryl had already been out three times with another instructor who had just quit. I told her, “Meryl, just drive around the neighborhood for a bit so I can see how she how you are doing. Don’t go on any really busy streets yet.”

Her driving talents seemed mediocre at best, but I didn’t have to grab the wheel and I only had to use my brake pedal once. She seemed to be a bit hesitant during this excursion. I wondered how I should handle my instructions for her.

But something else was distracting me from my duties. Meryl seemed to have taken a shine to me from the very beginning just like I had with her. I thought, She's just one of those naturally voluble people. It didn’t seem that I had any qualities that could possibly be attractive to her. My divorce had put a pretty big hole in my sexual confidence.

She would often touch me on my right arm and a few times she would rub my forearm or put her hand on mine. At one point we stopped to get take-out at a fast-food restaurant. She asked me, “Paul, do you mind if we parked in the back of the lot and talked for a bit?”

“Sure Meryl, that would be fine.”

We talked about our lives. She had graduated from the state college with a degree in English a few years earlier, but she had never earned enough money to move out of her parents' house. Now she was studying graphic design at a community college in the hope that she could get a more lucrative career.

During this talk, she turned to face me, and my spidey sense told me that she wasn’t just flirting, but rather she was on the verge of making a pass at me. She kept fiddling with her open blouse and touching her bare chest in the gap. She noticed me looking at her, and she smiled during my gaze at her bare flesh.

I was suddenly aware that I had an erection, and I didn’t necessarily want one then. I was still trying to focus on my job.  Maybe Meryl noticed something because she changed the topic and asked me about my divorce more than a year earlier. She said, “Do you ever miss your ex-wife?”

“Well, we had some rough times together, so I wouldn’t say I missed her.”

Meryl thought for a moment and said, “That’s not quite what I meant. What I meant was, do you miss her physically? Or to be blunt about it, do you still want her sexually?” Then she laughed at her own boldness.

Well, she had point. Getting laid regularly was one of the few advantages of a dying marriage, or at least it had been true of mine. I felt my face get warm as I blushed; I couldn’t admit anything like that to Meryl. She noticed my discomfort and said, “I’m sorry Paul, I didn’t mean to embarrass you that much.”

I got back to business, “Meryl, we should get back on the road. I mean, you’re are paying Supreme for this time.”

“I know. Maybe in the future, we can talk more about . . .” For a second she was unsure about what to say next. “I mean we can talk more about intimate matters as we get to know each other better. How does that sound?”

It sounded pretty good. It wasn’t just the physical contact I missed; I was craving female companionship of any sort. And this Meryl: I was already getting a sense of her sweetness and good nature. We’ll see how this goes. Maybe if this girl makes a play for me, I should accept it.

For the rest of the session we drove around and I guess I instructed her as best I could. She was a little wobbly when entering a wide boulevard. “Meryl, always check your mirrors during a move like that.”

“I know, I need to keep that in mind.”

When we finished and got back to her house, she said, “Paul, I always want you to be my instructor. Can that be arranged?”

“Yeah, if you call ahead, probably it can be worked out.”

She leaned over to kiss me and I thought it would be on the cheek. Instead, she turned my head with her hand and landed it on my lips. Just before she got out of the car, she said, “By the way, I think you’re really cute.”

When she was gone and I was driving away, I was aware of the strong desire I had for her. That night, I masturbated imagining her straddling me on the mattress. I ejaculated a thick stream upwards and it came pattering down all over me.

I still didn’t know why she would want me, but I understood that I didn’t need to know the reasons. If a woman showed interest, that was enough.

*****

Meryl didn’t waste any time in making her play for me. For the next session a few days later, she booked an hour-and-a-half, which was longer than usual for a lesson. This time she was wearing a denim skirt that revealed her knees. I made a note of her chunky lower legs. She saw me looking at her, and she smiled. “Do you like what you’re seeing?” I had the feeling she had smoked some pot that day as she had during the previous session.

I figured I had nothing to lose by telling the truth. “Okay, Meryl, I do like what I’m seeing.”

Her grin widened, and she said, “I think you’re a really sweet guy.” I still wasn’t sure what I had done to justify that praise.

About a half-hour in, she made her move, and she moved faster than just about any other woman had ever done with me before. We were driving past a lot full of truck trailers when she said, “I’m going to drive in behind these trucks and we can park.” I didn’t get a moment to protest; she just turned into the place. She winked at me, “You do know what it means to park with a girl, don’t you?”

“Parking” had a slightly antique 1950s sound to it, but I knew what she meant. It implied sex in a car, which could be anything from a make-out session to full intercourse. Of course, I didn’t know what the actual activity would be in this case.

We were completely surrounded by truck trailers, which offered us a degree of privacy. She turned off the engine and looked at me, but not for long. In a moment, she turned towards me, lifted her skirt, and spread her legs. I looked and saw that she wasn’t wearing panties. Her crotch was shaved and I saw her slit clearly as it cleaved her plump crotch.

I’ve never been very good at coming up with quips for such situations, and my comment was rather feeble. “Meryl, you’re not wearing any panties.”

Meryl found that amusing. “But I do have a pair, right here in my purse.” She took them out to show me. They appeared to be very ordinary white underpants. Then she had her arms around me and she was kissing me. During our make-out session, I rubbed her thick thighs but I didn’t attempt to touch her pussy. She already had the answer for that.

“Paul, how about we get in the back seat and have some fun? I think you know what I mean.” I thought, Meryl, you’re paying for all of this time, but when a woman makes an offer like that, financial matters seem to be much less important. What we did in the back seat was not merely heavy petting; it was mutual masturbation. She took my cock out and stroked it while using some hand lotion to lubricate me. My right hand was deep in her cunt, fondling her clitoris and the other parts of her genitals.

The results were predictable. When I ejaculated, most of it landed on the seat. A few moments later she was crying out, “I’m going to climax right now!” She spread her legs out, waving her sandaled feet in the air. Some kind of noise came out of her throat as she gyrated her hips around my hand. Her head shook so much that her glasses flew off.

Then it was over, and we had our arms around each other. It seemed suddenly very quiet, and the shadows from the trailers were spreading over our car. We didn’t say anything to each other. It was as if the suddenness of the act had stunned both of us into silence.

She got her voice back first, “Wow that was really intense.”

“I’d have to agree with you on that.”

Since bent over to retrieve her glasses. “Paul, I want to tell you something about myself, about my sexuality.”

That sounded like a worthy topic, but I was trying to be practical, I said, “We could just go and finish the lesson, then meet later at a diner or something.”   

“No, I’m too distracted, I couldn’t concentrate on driving lessons.” Before I could respond, she said, “Living with my parents, I don’t have any privacy. Could I ask you, what is your living situation?”

“I have a roommate, but it’s a two-bedroom apartment, so it’s not so bad.” I neglected to tell her that I had never invited a woman up to my place.

Meryl was pressed up close to me, with her bare legs across my lap and her right arm around my shoulder. I was feeling very relaxed, and yet I wanted to get going. “Are you sure you don’t want to continue the lesson?”

She ignored me, “I have to tell you about myself, and it’s difficult to do that. But I feel I can trust you, that you’ll understand me.”

“Sure, go ahead, I can handle it.”

She hesitated and she seemed to be getting her courage up to tell me about it. Then she said, “Okay, there is no point in dragging this out. You see, I will only have sex with a man anally and orally.” She giggled, “After a shower of course!” Then she put her hands in the air and wiggled her fingers. “And, as you just found out, manually too, I’d call it. But I’ve never had a man penetrate my vagina, I mean with his cock. Do you find that a bit strange?”

I did find it strange, but I was at a loss about what to say about it. I was sure that I never heard a woman say that before. Finally, I came up with, “Okay, since you were the one to mention it, what is your reason for this?”

“It just seems important to me to be a virgin until my wedding night. I’m sure it has something with the attitudes my family instilled in me.”

“But you’re not really a virgin, except in the most technical meaning of the word. I mean, you have been letting men . . .” I didn’t know how to continue.

Meryl was very blunt, and I had to admire her for that. “Oh, yeah, I do let men – what is that expression? – corn hole me quite freely.” She seemed to find that quite funny.

It was one of those conversations that was so strange that I almost didn’t grasp the weirdness of it. I said, “But you don’t get any pleasure out of that.”

“But I do, you just saw that. If you put your hand down there and fondle my cunt at the same time – well, I will quite reliably have an orgasm.”

For a second I thought this all was a put-on, some kind of elaborate joke. She had more to say on the subject, “In Greece and other places, girls will preserve their virginity by only having anal sex.”

“First of all, this isn’t Greece, and secondly, I think they’re basically kidding themselves.” Yet I knew what her next move would be – I’d be invited to be her next lover in that manner.

I was right, and she was quite blunt about it. “Paul, I want you to do this to me, during our next lesson together. Have you ever had anal sex before?”

“I have, a couple of times with this girl I knew in college.”

“Was it her idea or yours?”

I said, “Mostly mine, I guess. She was pretty indifferent about it.”

“Well, believe me, this is definitely my idea.”

“Why not just come over to my place?”

“I’m not sure, I just want our first time to be in this car.”

This girl seemed to have some money to burn on not learning anything from the Supreme Driving School. I also caught her phrase, “our first time.” She obviously wanted me to stick around for future trysts

I looked down at the seat, and I saw the seminal mess I had left on the cloth seat cushion. “I’m going to have to clean this up, which won’t be easy.”

She laughed, “Well, sex is a very messy business, isn’t it!”

After that, we sat in the front, listened to the radio, and chatted for a while. When it became time to leave, she said, “So I’m going to book some time with the car for the next session. Are you willing to do this?”

I thought, I’m lonely and sexually frustrated, and so is she. Why not just go for it?

“Meryl, sweetie, I’ll be there, I promise.”

She smiled at me, “And I promise that you won’t be disappointed in what we do together.”

*****

A few days later I picked her up for the big event. She was more dressed-up than previously, and she was wearing a blazer and a short black skirt. As we drove off, I asked her, “So where are we going for this?”

“I’d say that lot with the truck trailers. It’s almost ideal.”

When we got there we sat in the back seat and made out. At one point I undid her blouse and bra and I saw her wonderfully round breasts.

She said, “Nice tits, right?”

I decided it wouldn’t hurt to praise them. “Among the nicest I’ve ever seen.”

A bit later, she said, “If you don’t mind, I have a plan for the first time. Before you penetrate me, I think you should go down on me.” I must have looked confused, because she continued, “I’m very orgasmic that way. I’m sure you know how to eat out a girl’s pussy, isn’t that right?”

I tried joshing with her, “Of course, I’ve had plenty of experience doing that.”

A stray thought occurred to me that I didn’t tell her about. Maybe, since she’s never been penetrated vaginally, she’s developed an extra sensitivity to having a man’s mouth and hands in her cunt. Pure speculation of course, but I still believed it was possible.

I noticed something else, “I don’t think you’re at all stoned this afternoon.”

“No, I’m not; I want to concentrate on what I’m doing.”

Soon she was sitting against the rear seat cushion with me kneeling on the floor in front of her. She lifted her skirt and took off her lacey little black panties. Her legs were bare; she had no stockings on.

My oral sex act on her went very well. Soon she was waving her legs around in the back of the car. I noticed her strappy black shoes and her red toenails in the air above my head. When she climaxed, she grabbed my head and moved it against her own writhing crotch. She moaned in pleasure and, in the last moments when she could still talk, she praised my cunt-licking abilities.

When it was over, we sat quietly in the back and just lived in the moment. Finally, she said, “All right, let’s do this. You’ve had anal sex with a girl before – that’s what you told me.”

“It was like maybe twice, and it was at least fifteen years ago.”

“Okay, so you’re not a complete newbie at this, but I think you need some refresher lessons from me.”

“I remember that she wasn’t very interested in the whole thing.”

She laughed, “Well, I am! Don’t worry, I’ll guide you; I’ll tell you everything you need to know.”

Meryl removed her skirt and dropped it on the floor next to her panties. Then she got up on all fours on the back seat and waved her ass at me. She looked back at me and said, “To start with, I will fluff you, rub my behind against your crotch. Drop your pants so you are bare." When I had down that she looked back at me. “You look pretty stiff already!”

I complimented her again, “You do have a lovely big round ass.”

“Why, thank you. I think so too!”

Eventually, she reached back to rub some lube on my stiff cock. “Now, be careful going in. Just push slowly until you feel the muscle give way.” She giggled, “Sorry I had to be so clinical about it. Now when you’re in, take it easy. You may not want to go in all the way to the hilt or thrust too rapidly. Do you think you’re ready?

“As ready as I’ll ever be, I guess.”

“Now, I still want you to fondle my pussy, as I’ve said before. It’s possible I may climax again.”

She reached back and lubricated my cock. Then I aimed for her hole. I pushed against it, and suddenly it opened and I was inside. She grunted something at the moment of penetration. My right hand went down and fondled her pussy; my left hand gripped her hip.

I had forgotten how tight it was in a woman’s behind, but it felt very good on my cock. No vagina had ever felt like her anus did. I tried to get a rhythm going and rub her genitals at the same time. She gentled rolled her backside against my front. I heard her moaning, but I didn’t know if it was from the penetration or from my stroking of her genitals.

In any case, it didn’t take long for me to ejaculate into her. I probably was already charged up from my oral sex with her. I could feel a large amount of semen spurting out of me. Meryl noticed it too, and she said, “That’s it, Paul, it feels so hot. Put all of it up into my not-so-little rear end.”

When I was done, we then sat there together, side-by-side. After a few moments, I said, “I don’t think you came yourself.”

“No, I didn’t, but sometimes it just goes like that. You more than made up for it with your mouth and tongue before.”

There was something I had to know. “Is it possible for you to come by just be being penetrated anally?”

“Not very likely, I need the manual stimulation too.”

It seemed like a very prosaic conversation for such a topic. I held her and I wanted to say something like, Meryl, I love you. But did I really love her? I hardly knew her outside of this car. I did like her, but our relationship so far was mostly a physical one.

I asked her, “You still have a half-hour left. Do you want to drive?”

“No, I’m not interested in that right now.”

“You know, at some point, I have to take you for your road test.”

For the first time she looked worried, “And if I pass that, it’s the end of my professional relationship with you, isn’t it?”

“Yes, your connection with the Supreme Driving School will be over.”

She hesitated a bit and then said, “But I don’t want my connection with you to end. I mean, I still want you, I want to be with you. Do you understand that?” I looked over at my bottomless Meryl with her skirt and panties on the floor. I knew I had just left a big cream pie in an unusual place in her body. But was she just a fling to me, or something more serious?

I thought for a second. I had been alone for quite a long time. This Meryl had an unusual predilection, but she was sweet and sexy and I could keep her if I wanted her.

I made up my mind. “Yes, Meryl, I want us to stay together.” I added something that was perhaps unnecessary. “I think we need each other.”

She smiled, put her arms around me, and kissed me. As we sat there holding each other in our blue Taurus, she asked. “So, how did it feel to have your first anal sex in over a decade?”

“Meryl, it felt just great.”

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