Joanna, I Love You

My New Neighbor

From the beginning, my parents thought that there was something odd about Mrs. Joanna Pollack, to whom they had rented an apartment on the first floor of our two-family house. Within a few days, they had labeled her with the word "tranny," although they didn't specify what evidence they had to believe that about her. They openly discussed her with me, however.

There was certainly no Mr. Pollack on the scene. However, I soon noticed my own clues that made me wonder about her. In less than a month, I was able to decisively know her real identity beyond a doubt. Or, to put it another way, she was the one who decisively proved it to me.

Joanna moved in at the beginning of the summer of 1992. I was nineteen and had had just finished my freshman year at Rutgers University, which wasn't that far from our place in Edison, NJ. I was still living at home at that point, which certainly saved a lot of money on dorm housing and university meals.

A notable fact that bothered me a lot was that I hadn't even been on a single date with a girl yet. I suppose I wasn't that bad looking, but I tended to be a bit introverted and I had never met anyone I felt comfortable approaching.

Regarding Joanna, I had a general idea of what transgenderism was, but it was hardly of great interest to me. Issues of gender identity were not as well publicized back then as they were later on. Thus my knowledge of the issues involved was pretty basic.

That June, such matters seemed pretty remote, even irrelevant to me, and my sexual priorities were simply about losing my virginity. I saw it in terms of getting a girlfriend, not simply "hooking-up" with one of my classmates.

It would be several years before I even heard the term hook-up. Those certainly happened, of course, but they weren't as close to mandatory at colleges as such arrangements later became.

I knew for sure that I would be in a sexual and romantic limbo until the next semester started in September. I wasn't going to cold approach some girl at a mall or fast food place. It appeared that I was facing a lonely summer.

Joanna was hardly shy, and I often ran into her around our house. Sometimes that happened when I pulled into our driveway in my beater 1985 Chevy Nova that I had bought for my commute to school.

She parked her Mitsubishi Eclipse on the other side of the driveway away from our house. I had no idea where she worked or where she went during the day. Whatever she did seemed to not be on a conventional nine-to-five schedule.

During these encounters, she seemed friendly, even warm, towards me, which was surprising because she had known me for such a short time. My parents and my older sister living upstairs generally minimized or avoided any contact with her at all, so maybe she appreciated my genuine sociability with her. I was usually wary when dealing with new people, but yet I felt comfortable around Joanna.

The first time she introduced herself to me in the driveway, I defaulted to the politeness I had learned growing up and called her, "Mrs. Pollack."

"Oh please, that makes me sound so old. Just call me Joanna."

I had also no idea of what kind of social life she had and what she did when she wasn't in Edison. Later that summer, occasionally a man or woman would stop at by her place for a visit and a couple of them would stay for the night. I suspected that the "Mrs." that she used in her name was made up, and I wondered if there had ever been a husband in her life.

During those early days, I did assess her to see why my parents had formed that opinion about her. I tried not to be too obvious in my appraisals, and she didn't seem to notice how I was looking at her. Or maybe she did notice and she didn't care.

Anyway, I began to think that there was some evidence that my family's conclusion about her was correct. However, my own ignorance was an obstacle for me in understanding her.

In her first week there, she'd sometimes see my car through her kitchen window as I arrived in the afternoon. She would often come out and chat with me on those occasions. During the second week of June, she invited me into her kitchen for coffee. I was still a tea drinker at that point, but she gladly accommodated my preference.

That tea time gave me a chance to look her over more closely than before. She was rather tall, about five-eight, only an inch shorter than I was. Her hair was long and light blonde, but she often had it tied back in a ponytail or held it in place with a hairband across the top of her head. I wondered if that was her natural hair color, but I doubted it.

Joanna always had a considerable amount of make-up on, including eye-shadow and false eyelashes. Thus it was difficult to know exactly what her unadorned face looked like. But while presenting herself as a woman, she looked attractive anyway. I had never been good at gauging people's ages, but my best reckoning was that she was in her mid-thirties.

Another aspect of Joanna that struck me was that she always seemed to be dressed up; I rarely saw her truly casually dressed. She seemed to prefer skirts or dresses, often with nylon stockings. I sensed she put some thought into what she'd be wearing each day.

During that kitchen visit, which went on for about nearly an hour, I got some hints about her true identity. For one thing, she had substantial breasts, which seemed to preclude her merely being a transvestite.

At least, that's as far as my limited knowledge would take me. I knew that some male-to-female transsexuals would have hormonal treatments that would cause breasts to develop. That seemed beyond what most mere cross-dressers would bother with. What I could see of her body was that it was completely free of any hair except for what was on her head.

Of course, I didn't know what was under her clothes, so I couldn't tell whether she had gone through gender-reassignment surgery or, as it's sometimes called now, gender-affirming surgery. Sexuality and gender were sensitive topics even then and they generated a complicated terminology.

Yet I thought, this person has to do a lot of work to stay in character. In fact, I had never seen her out of character. What she looked like in private was unknown to me. Later I figured out that she didn't need to fake anything; she was just being herself.

I did notice some anomalies that my family may have first seen. Her hands and arms seemed to be stronger than I would have expected on most women. That was partially mitigated by the red or other color nail polish she usually had on.

I was surprised that I liked he almost as soon as I met her, and for some reason she liked me. Whether there was any sexual attraction involved with our feelings at that early point was hard to say. I guessed that she must have had difficulties in her life, yet she struck me as being open and unpretentious.

During our first conversation at her kitchen table, I think she sensed the confusion I had about her, and she did her best to ameliorate that. Mostly, she asked about my life and family, and she revealed little about her own experiences.

Before it was time for me to go, she made a personal comment. We had been talking about what it was like at Rutgers, and she said, "I bet you are just slaying all those girls over at your school."

I could feel myself blushing, but I knew I had to say something a bit vague and yet that showed that I was at least in the dating game. "Well, yeah, I guess I'm doing all right."

Her expression revealed that she didn't believe me, but she immediately put her hand down on mine which was resting on the tabletop and then she squeezed it. My first impulse was to pull back, but I knew how rude that would look so kept my hand in place under hers.

"You can do a lot better than just all right, Chris. I want you to know, I think you're very cute."

I came up with a lame response. "Well, thanks."

"Part of it is those intense dark eyes you have."

The best I could come up with was the statement, "That probably comes from my father's side of the family, which is Italian." I thought, dummy, that's already obvious to her from my last name.

"So your mom isn't Italian? She certainly looks it with that almost black hair she has."

"No, her ancestry is German."

I thought Joanna might offer info on her own background, but she didn't; she kept the conversation mostly about me and my family.

Other thoughts went through my mind as we sat there talking. Is she flirting for its own sake, is she really attracted to me, or was she just playing a little game to tease me? I looked into her face again, and she was smiling at me. I knew I was blushing again; I could feel my face warming.

Am I perhaps sexually interested in this Joanna person, despite whatever gender she used to be or identifies with now? I felt some dissonance about that, and I decided, well, maybe I am indeed somewhat attracted to her. Is she actually attracted to me, or is she just having some playful amusement at my expense?

That night I tested my attitude towards her in the most direct way possible. After I had supposedly gone to sleep, I stood next to the bed and I masturbated imagining Joanna kneeling on the floor in front of me. In the fantasy, was wearing the same flowered dress and white shoes I had seen her in earlier.

I had never been blown by anybody in my life, but the image of her red-lipsticked mouth and red-nailed fingers working on my stiff cock worked perfectly. To top off my vision, I pictured her other hand gently stroking my bare buttocks.

The result was a very intense orgasm. I frantically whispered her name as my ejaculations shot out; the biggest one hit the wall just opposite where I was standing. I had never been able to do that before, and once I calmed down I was impressed at my own sexual feat.

A little later I lay there pondering why this person had such an impact on me. Maybe it had something to do with her proximity just downstairs, and the sweet way she had held my hand and smiled at me. I think you're really cute, as she had said.

Well, I thought that she was cute too, despite whatever she once was or what she identified as now.

Many times I had pictured girls I knew having sex with me, including having them suck my cock. However, Joanna seemed more tangible than any of those other women. Those classmates rarely talked to me; I seemed invisible to them. Joanna lived right in my house, and she had given me the only compliment about my appearance I could remember. Of course, was Joanna truly female now or was it a concept formed in her mind? I couldn't say for sure.

I wondered about my own sexual orientation, which I always had identified as straight. And yet I felt the pull of lust towards my gender-bending neighbor. I remembered a Kinks song that had been released over two decades earlier, girls will be boys and boys will be girls. It's a mixed up, muddled up, shook up world, except for Lola.

Or in my case, except for Joanna. It was obvious that the narrator of the song had lost his virginity to Lola, and he seemed to find that quite acceptable, pleasurable even. I had never wondered what I would do in such a situation because it seemed so remote to anything in my life. Now I felt I might go over the sexual verge with this person just downstairs.

That was all beyond my capacity to process then. I lay in my bed, and I supposed I would find out what was going to happen soon enough.

Joanna's Generosity

While the Lola of the song snagged her new lover in one evening, it took Joanna nearly two weeks to get me. I was getting out of my car in the driveway one afternoon when she emerged again from the side door of her kitchen.

I wasn't surprised to see that she was wearing a summery, short-sleeved dress, nylon stockings, and some rather unique blue and red medium-heeled shoes.

Her hair and make-up looked good, although the latter was a bit on the heavy side. Overall, she didn't look like a woman just hanging around the house on a quiet day. Rather, there was an air of self-dramatization about her, as if she was ready for some event that I couldn't quite imagine.

It seemed that my arrival could be that day's event, and I decided to accept whatever way Joanna might handle it. In the kitchen, she invited me to share some brandy with her, which seemed a bit fancy for a Wednesday afternoon.

While sitting at her table I looked for more clues about her identity. Her voice was a bit husky, but a casual listener might not pick up on anything that unusual. It occurred to me again that a transgender person had to be careful to pass as whatever gender they believed was their true self. Yet Joanna always seemed at ease around me.

Maybe she just has some natural acting talent.

Perhaps her life was a form of presentation, I'd call it, but she seemed to have a knack for handling it and she seemed comfortable with herself. I wanted to ask her about what it was like to be her, but I didn't feel I knew her well enough yet to bring up such a question.

At the table, she seemed as fond of me as she had from the day she had met me. I pondered the mystery: what exactly is it that she sees in me?

Then, after about fifteen minutes, she made her move on me, and she wasn't very subtle about it. Later I thought that there was some male directness in the way she acted; perhaps there was a mixture of both male and female characteristics in her psychological makeup. Whatever it was, I had been dealing with girls since high school -- I had even asked a few out -- but by nineteen I hadn't had the smallest bit of success with them.

After all of that fruitless effort on my part, it was Joanna who finally made a pass at me. Maybe calling it a "pass" was an understatement. She got up and went over to the sink and began moving dishes from the drying rack to one of the cabinets. She said, "Chris, I hope you don't mind me asking this -- I know I've mentioned this before -- but do you have any girlfriends over at Rutgers?"

She partially turned to look at me and she smiled. She is a nice-looking, good-natured blonde lady, but I know she is a lot more than that -- or maybe she's just something different. Then I tried to remember my response from the previous week. I fumbled into an answer. "Well, as I said, I'm sort of playing the field, seeing what's out there."

Joanna laughed, and I knew she didn't believe me. Then she saw the look on my face, and she said, "I'm sorry, I'm prying into your business. But if you want to talk to me, I'm willing to listen." I just sat there, pondering what to say, and she indicated the brandy bottle on the table. "Go ahead, refill your glass, think about your response for a bit."

She faced me and leaned back on the sink. When I started on my second glass of brandy I didn't know what to say to her. She knew what to say to me, "If you want me to help you with your problems Chris, I am very willing to do that."

That could mean any number of things, and I felt confused. "Help me with what, exactly?"

"Oh, I think you know what I mean."

I gave a limited hang-out confession. "Okay, I admit that I wish things were going better over there -- I mean at Rutgers, with the girls I mean."

She laughed again, a little more softly than before. "I already knew that."

"How could you guess? Is it that obvious?"

"Look, young guys like you -- what are you, nineteen? -- can't help but brag if they are getting some regular pussy. I hope that wasn't too blunt."

I pretended to be nonplussed by her statement. "No, I wouldn't say it was too blunt," although I it certainly was to the point. Then I had to satisfy my curiosity by re-framing my question. "So what would you do to 'help' me? You still haven't told me that."

"Let me show you something, you'll see."

She faced the sink again and pulled her dress above her waist. She wasn't wearing panties, and I could see her smooth, pale buttocks. Black garter straps were coming down to hold up her tan stockings. I had heard of garters but I had never seen one.

Then she looked back at me, and I wasn't so naïve that I didn't recognize a come-hither look when I saw one. "I have a cute backside, wouldn't you say?" I suspected that she wasn't exposing herself merely to tease me. "Do you like what you see? There's a lot more, you know."

With that, she put her right leg up on the counter, and I saw her balls and semi-erect penis hanging down over the edge. Her genitals were clearly visible against the wooden door under the sink. One of her blue and red shoes was almost touching her cock.

"Pretty nice, wouldn't you say?"

Yes, I did perceive them as quite "nice," although it was much more than that. Something about the sight of male genitals attached to a seemingly female body aroused me, just as it had in my bedroom fantasies As I tried to formulate an answer for her, she said, "Would you be a dear and refill my glass and bring it over to me?"

I did what she requested almost automatically. Meanwhile, she had hopped up on the counter and sat there sideways with her feet next to the sink. As I walked over there, I could see her cock had gotten even stiffer and it was pointing almost straight up.

So I knew in that she wanted me, and she was testing me to see what my reaction would be. In that instant, I made my decision.

When I was next to her, she took her drink with her left hand and used her right one to firmly hold my wrist. I think she wanted to see if I would pull away, but I didn't.

"Chris, I know this is a lot for you to deal with, so just listen to me for a moment." She sipped her drink. "Now, I'm sure that you and your family have known what I really am. But you've been the only one of them who hasn't judged me, I can tell that. I can also tell that you like me quite a bit."

It seemed okay to admit it. "All right, that's true." I was aware that she was probably going to seduce me, and it was beginning to seem like an exciting idea.

She looked down at her stiff shaft. "And I like you too, as you can plainly see. I suppose you have thought about me sexually?"

I answered, but it was difficult for me to get the words out. "If you must know -- okay, I've masturbated at times imagining you." Was I going to get away with saying that?

I certainly was, and she seemed pleased by my honesty. "Oh, you're very sweet, I already was almost sure that you were fantasizing about me. I'm very familiar with what young guys like you do and think. They masturbate as often as they can get away with it, isn't that true? So what do you picture that we were doing?"

I was getting more comfortable revealing my thoughts to her. "For one thing, I like the red lipstick you wear." That seemed a bit vague, so I got more specific. "I fantasized that you were sucking on me -- blowing me, in other words. I could see your hands holding me and stroking me too. That's what I've thought about you."

By this point she had opened the front of her dress and had revealed her breasts to me; she wasn't wearing a bra either. Then she got up and stood in front of me, putting her arms around my waist. That seemed like another test to see if I would recoil from her, but again I did not.

"I can be quite naughty at times. As you have noticed, it's a warm day and I'm not wearing any underwear."

I dared say, "So you planned it that way?"

"Of course, baby, isn't that obvious?" Then she whispered into my ear, "What did you think when you saw my cock and balls?"

I softly responded, "I think that they are..." I couldn't quite say beautiful. "I admit, I like them. I mean, I want to make you come."

"And I'm sure you can do it. Chris, I have to tell you that I like what you've thought about me. I mean I've fantasized about making you come too. We should enact these things in our real lives."