In the late spring of 1981, when I was nineteen, a woman named Miriam Roston moved into my building. At least I initially assumed that she was a woman. In New York, people generally were non-judgmental and left other people alone.

But this was in the East Bronx, not Manhattan, and after about a month, my family started speculating about her. They used terms like “tranny” and “shemale” to describe her, although they didn’t exactly dislike her either. But neither did they go out of their way to socialize with her.

She lived on the fourth floor and we were on the sixth, so I often met her in the elevator. For some reason, she seemed to like me, and we often chatted a bit, sometimes for a short while in the lobby or out in the street.

My family’s views about her caused me to try to assess her more closely, and I couldn’t pin down what her true gender was. She was a bit tall at about five-foot-eight, and she had light blonde hair which I suspected was not its true color. It was usually styled so that it was down to her shoulders and was held in place with a hairband across the top of her head. At other times she tied it back in a sort of ponytail.

A notable thing about her was that I always saw her dressed up to some degree, although she left the building at different times that didn’t seem to coordinate with a regular job. I was finishing my freshman year at the City College of New York, so I had a somewhat erratic schedule as well.

I also noted that she always had makeup on, sometimes a bit on the heavy side, but it made her look attractive anyway. My ability to guess people’s ages wasn’t that sharp, but I thought she was in her early thirties. Overall, at first glance, Miriam appeared to be a nice-looking but mature lady.

Talking to women was not my strongest point. In fact, I was still a virgin, although I was trying to ameliorate that situation. Miriam struck me as good-natured and friendly, and I found that I liked her too. Her true identity didn’t bother me, and she, I’m sure, caught on to the fact that I wasn’t prejudiced against her in any way.

My attempts to find a girlfriend at City College weren’t completely failing, as that spring I began dating a freshman classmate named Jennifer Saltz. At first, it seemed promising because she was the first girl I had even taken to lunch. Yet it wasn’t a completely satisfying arrangement for me, as I wasn’t getting very far with her sexually.

The main thing we had in common was that she lived only about three blocks from me and we sometimes took the subway together to and from school. After three months, it seemed that she thought of me as more of a friend than a lover.

I was pretty naïve about dating relations, and I also wasn’t the most assertive person in the world. In my mind, I had images of hippie girls from a dozen years earlier who would supposedly ball anyone at a moment’s notice, and more recent stories of “punk” girls who were just as loose.

Of course, few if any of the female students at my school were like that. The sexual revolution had been going on for two decades, I believed, but I didn’t see any signs of it within my personal sphere.

Jennifer certainly didn’t fit my expectations. I soon wondered if I was simply a “fill-in” guy until someone better came along. It seemed that I wasn’t bad looking, but I was only about five-foot-nine and I was on the skinny side. My generation was about the last that didn’t work out in gyms as part of our regular routines.

My new girlfriend was on the quiet side, and she was hardly flashy. Her thick brown hair was her best feature. Getting any affection out of her only happened under duress if I pushed her a bit for it.

We sometimes made out at some place on the CCNY campus, such as in the Finley student center lounges or, since the weather was warming up, outside on one of the grassy lawns. Those were always rather restrained activities, and I never tried to go further than stroking her arms.

A few times I took Jenny out to dinner and a movie, and I always had her back home by 11:00 PM. Once I tried to get more forward with her on such an evening. I directed her so that we could sit in a spot under the staircase of her building just beyond the lobby. I attempted to rub her small breasts through her blouse, but she firmly rebuffed me.

I thought she might even break up with me over that incident, but apparently she didn’t have a back-up plan to replace me either. Thus, she never mentioned my clumsy advances afterwards.

It felt like I was still living in the 1950’s with that unresponsive girl, and I found it baffling. Merely some mutual masturbation would have satisfied me, but we never got close to opening up each other’s clothes.

Masturbation was the only release I could count on, and I usually did it once at night and often during the day in a campus restroom stall if I could get away with it. Sometimes Jenny was the imaginary object of my intense self-stroking, and she appeared in every possible sexual act my fantasies could conjure up.

I was too diffident to buy porn for myself, but friends would give me dog-eared copies of Playboy, Penthouse, and Hustler that they had finished with. Some of the pages were stuck together; they had obviously ejaculated onto the photos. I admit, I wound up doing the same thing to those publications.

Some hope arrived in June when I was able to pool enough money from my part-time jobs to buy a car my grandfather was willing to sell to me for $900. It was hardly an exciting vehicle, a light-green 1972 Buick Skylark sedan, but I knew he had taken good care of it ever since he had bought it when it was only a year old.

Best of all, it had a generous-sized interior, including its rear seat. Immediately I was imagining having a relatively private place to fool around with Jenny, assuming I could find a place to park it with her.

My not particularly naughty girl didn’t share my excitement about my brand-new used vehicle. Nevertheless, I got my courage together and asked her for a very 1950’s-style date, namely to a movie drive-in. There was only one anywhere within an easy drive of us, which was the Whitestone about two miles away near its namesake bridge.

Surprisingly, she agreed to go with me on a Thursday evening. The venue had been “twinned” a few years earlier, but Jenny didn’t seem to care about which of the two available films we saw. The first was a romantic comedy with Alan Alda called The Four Seasons, and the other was a remake of the 1943 film noir The Postman Always Rings Twice.

She seemed indifferent to both of them, so I chose the latter. After three months with her, I was beginning to think, this girl is not simply quiet, she seems to lack any personality at all.

Thursday evening was warm, and I drove over to pick up Jenny at her building. She was waiting outside the lobby, and she came right up and opened the passenger-side door for herself. I noted that she had dressed up a bit in a short-sleeved yellow blouse, a brown skirt, and brown chunky sandals. I got a peck on the cheek as a greeting, and we were off on our cinematic adventure.

I played the radio as we had one of our usual desultory conversations. But the combination of having a car of my own, the sight of Jenny in her skirt, and my own hormones resulted in some very intense sexual thoughts about my dating partner. Her legs were bare, and my mind keep wandering to what kind of panties she might have on.

In fact, I got an erection from my thoughts alone, which is very easy to do at such a young age. I had heard that nineteen-year-old guys were at the peak of their sexual keenness, although that was not something I could verify. I was definitely fantasizing about Jenny’s genitals under her loose skirt, a sight I only knew from magazine pictures.

It wasn’t very realistic, but I was hoping to get a chance to at least feel my girl’s private places, maybe even getting some hand action inside her underpants. It did occur to me how pathetic I had become in my quest for the smallest bit of sexual satisfaction from something besides my blanket or my own two hands.

I had never been to any drive-in before, but I decided to park at the far right edge of the lot. I knew that light from the screen would brighten the interior of the car, and I hoped that having no other patrons parked on that side would give us a modicum of privacy. I even had visions of somehow getting into the back with Jenny and maybe going as far as I could with what used to be called “heavy petting” in the old days.

Of course, I failed totally from the very beginning of my efforts. As the opening credits began, Jenny was sitting close to me, but she was not actually in physical contact with the side of my body. I made my first move by putting my right arm around her shoulders and very gently pulling on her. She did move an inch or two closer to me. Well, that’s a good start.

About two minutes later, I shifted my arm down her back and tried to get my hand near her right breast. She wasn’t particularly bosomy, but it seemed like I had a chance to at least touch something. Briefly, I thought, here it is, the 1980’s, and I’m still thinking in outdated terms like above the waist and above the clothes.

It might as well have been 1954 from Jenny’s reaction to my tentative probing. She slid, or jumped it seemed, across the bench seat so that she was against the door. My arm flopped onto the cushion.

“Just what the hell do you think you are doing?”

I had learned that even if caught in an act with some wrongdoing, I should just lie about it anyway. “Ah, nothing really, I mean I wasn’t trying to do anything in particular.”

“It’s so obvious, you must think I’m really dumb.”

I came up with an irrelevant statement. “I never thought you were dumb.”

I knew enough not to apologize, yet I felt my face warming up with embarrassment. I hoped that she would say something else to at least give us a chance for some further communication, but she said nothing. Perhaps she wanted to get more comfortable because she moved away from the door a bit so she wasn’t sitting on the very edge of the seat.

We sat there, each of us staring at the screen and not saying anything. Jenny had her hands folded in her lap, and I had mine loosely resting on the steering wheel. Then, early in the movie, a scene was shown that made me regret having picked that particular film for the evening.

That scene, of course, was the steamy sexual tussling of Jack Nicholson and Jessica Lange. At first, she seemed to be resisting him, but then she knocked the bread and dough off her kitchen table and taunted him by breathlessly saying, “All right, come on, come on.”

Bad boy Jack responded with some very direct foreplay, getting on top of her and putting his hand under her dress. There were close-ups of him rubbing her pussy through her panties. Wow, she has white garter straps; I’ve never seen those before. In fact, the whole sequence was more explicit than anything I had ever seen, including what was in Hustler magazine at the time.

Lange, as Cora, obviously liked it, because she put her own hand down to guide him, and she got her cute little waitress shoes around his back. My God, they’re going to fuck right there on the table!

My miscalculation was that Jenny, only being human, would respond to this cinematic hotness with some interest of her own. Without planning ahead, I put my right hand down and held her bare left knee.

That time she slapped my hand and jumped away again. “Stop that! Just because of what’s going on up there doesn’t give you the right to touch me.” Before I could respond, she continued, “Why did you take me to see this anyway?”

I thought I had ironclad excuses. “You could have picked the other one. And I didn’t even know what was in this.”

“You’re completely missing the point. You wanted to get your hand into my pants like he was doing with her.”

She had known exactly what I hoped to do. I said another irrelevancy. “Jenny, you and I have been going together for three months.”

“So what? That doesn’t give you the right to do anything dirty to me. Just keep your hands to yourself.”

What an annoying prude this skinny little twat is. My thoughts were not generous, but I was feeling anger as well as embarrassment. Meanwhile, on-screen, Lange had changed position and was coupling with Nicholson by getting on top of him. Why can’t I meet a woman as eager as that one? And it’s supposed to be the 1940’s!

I offered a conciliatory gesture. “We could just leave now if you wish.”

“No, since we’re already here, I want to see what happens next.”

What could top what we were witnessing right then? But we stayed, gazing out through the windshield until the movie’s tragic conclusion. I was determined to say nothing until Jenny said something first but she never did.

We drove all the way back to her building before I finally relented, “I’ll go upstairs with you.”

All I heard was, “Never mind,” and she got out, leaving the door open. I leaned over to close it and I watched her enter her lobby. “You could have closed the door.” Then I said more out loud what I hadn’t dared to say in person. “I know how horny girls get too. And I know you’re going to masturbate tonight imagining that you are Cora.”

That wasn’t too comforting, because assuming that I was correct, Nicolson would likely be the object of her desire, not me. It didn’t matter, I knew, because I was going to masturbate myself when I was in my own bed.

At home, that night, I did it twice, thinking first of Jenny and then Lange. It felt great, but then I had that post-jerk-off letdown of realizing that my fantasy ladies were there only in my head.

The next day, a Friday, I called Jenny’s number and left a message with her older sister. Not surprisingly, I heard nothing back from her that day.

I was too proud to call again the next day, and I was resigning myself to experiencing my first breakup. It wasn’t that I was losing that much. Jenny was in one of my classes, which is where I had met her, but the semester would be over in two weeks.

In the early afternoon of Saturday, I was coming out of my building with no particular destination in mind when I met Miriam coming in. She was nicely dressed in a white dress with a flowery pattern, nylon stockings, and blue medium-heeled shoes. Her hair was in its ponytail configuration, and her blonde bangs fell over her forehead.

“Hey Jeff, how are you doing today? You look a bit down right now.”

I had been almost unconsciously pondering Miriam for a few weeks, and I could detect her warmth and openness. I was beginning to like her in the same way she liked me. Thus, I blurted out an answer. “To tell you the truth, I’ve been having some romantic problems recently.”

She responded with interest to my situation. “It must be that girl from your school I’ve seen you with, right?”

“Yes, that’s her; her name is Jenny. Something specific happened this week with her and I think she’s broken up with me.”

She wanted to hear about it. “If you like, come up to my place and we can talk about it over some coffee.”

I managed to say, “Actually, I’m a tea drinker.”

“So, I have tea too.” I must have been standing there looking confused, because she said, “Jeff, unless you have something planned, I meant right now.”

“Oh sure, I was just mulling over...” I didn’t know what I was mulling, so I followed her back inside.

In the lobby and the elevator, we talked about how I had met Jenny and how we sometimes shared the commute down to the college. I was close enough to catch the scent of Miriam’s perfume. I also noted that she had breasts that were not that large but certainly bigger than what Jenny had.

In her kitchen, she heated up some water and made instant coffee for herself, and a cup of tea for me. Then, she sat opposite me at her table. It was the first time I was that close to her for more than a minute or so, and I tried to assess who she really was.

Her make-up and hair were very nicely done, but I did pick up on a few anomalies I hadn’t noticed before. It was subtle, but there was a bit of huskiness in her voice. He dress had short sleeves, and her hands and arms appeared stronger than I had seen in most women.

Yet it was the content of our conversation that got most of my attention. I was completely honest in describing what had happened in the car and what we had seen in the movie.

“I haven’t seen it yet, but I’ve heard about what Nicolson and Lange do – or at least the outlines of it.”

I decided to be blunt. “The most explicit shots show him rubbing, well, rubbing her crotch through her panties.”

“And you, of course, tried to do the same with this Jenny.”

“She was wearing a skirt, but I didn’t just grab her. All I did was put my hand on her knee.”

“Which failed, I imagine.”

I wasn’t sure why I was confiding my experiences to this person. Somehow, while I was feeling lonely and bereft, it seemed that Miriam was the only one I knew whom I could trust with my story.

She looked away for a moment to think, then she gently patted my hand as I rested it on the table. “Jeff, honey, I want you to know that you’re a very cute guy, but you don’t know a thing about nineteen-year-old girls. They don’t know what they’re doing any more than you do, but in a different sort of way.”

I caught that she had called me honey, but I was also baffled by her statement. “What is it that I’m supposed to know?”

“You can’t be intimidated by them, because they think they are at the peak of their attractiveness.”

Well, I’m at a peak of sorts too. I come out with, “Maybe this Jenny is just a lost cause.”

She laughed at that, “That’s the right attitude!”

A couple of minutes later, she said, “Say, Jeff, I have seen that car you’ve got now.”

“A Buick Century, not too exciting, I know.”

“But the thing is, I’ve never been to a drive-in. The Whitestone is the only one I know anywhere near here.” I knew what was coming next. “I was wondering, why don’t you take me to see a movie over there?”

Was she offering a date with me or just a friendly outing? I speculated that the former was more likely, but I didn’t know how to handle the situation. I didn’t want to refer to her age or gender status, so I said something about myself. “I’m a little too young for you, aren’t I?”

But she took it very well despite the implication that I knew what she had intended. She made a scoffing motion. “Please, I think you need some advice from a mature woman.”

But you’re not a woman. Well, maybe you’d like to be one or, deep in your psyche, you believe you already are. She was smiling at me, and I noted her red lipstick; I could imagine how my cock would feel if it was in her mouth. I’m not gay or bisexual, I thought, but there is something appealing, even attractive about this person.

That fit into an idea I had never expressed to anyone before, namely that sexuality is as much an emotional phenomenon as a physical one. Maybe I wasn’t as straight as I had assumed.

She put her hand on mine again, and that time she pressed down lightly on it. “I’m not trying to make you feel uncomfortable; you can do what you think is best.”

I had already made up my mind. “No, I’m fine with it. When would you like to go?” I must have sounded convincing; I had even convinced myself.

“Anytime that’s good for you. Let’s exchange phone numbers.” There was a notepad on the table and we both took sheets. When Miriam was done writing, she winked at me and said, “Don’t worry, this going to be a lot of fun!”

Later, I had the insight that she might be lonely too. And, the effort she put into her gender role must have been considerable. But she didn’t seem like the complaining type.

I called Miriam later that week and invited her for that Friday. We met in her apartment, but we didn’t linger there. My car was a couple of blocks away and we walked over to retrieve it.

She was wearing clothes that I had never seen before. Her white dress was decorated with red cherries, of all things. The rest of her outfit was coordinated with a red belt, a red hairband, white shoes, and nylon stockings. She also had an open white sweater, so I couldn’t see what kind of sleeves the dress had.

She’s dressed up for me, obviously. Then I wondered about the cherries. Was that some kind of reference, maybe unintentional, to my inexperienced status?

I played the radio in the car again, but it was an entirely different kind of experience than I had with Jenny the previous week. Our conversation was relaxed yet animated, and we talked about music and also about some of my experiences in life.

As I had thought during our coffee/tea date, I again had positive impressions of her. She seemed kind, sweet even, and also completely genuine. I wondered again what she saw in me.

That time I chose the Alan Alda comedy, although I soon found out that Miriam was not on that trip to see a movie. Since we were in the opposite lot, I parked on the far left side that time.

Soon after the opening credits rolled, Miriam moved closer to me and said in a low voice. “What is it that you wanted Jenny to do to you in this car?”

I said the truth. “I was kind of wishing she’d take my cock out and rub it.”