Chapter 9: Arlene’s First “Real Date”

That weekend, the first of the new school year, I saw both of my “girlfriends,” and I tried to make comparisons between the two and what I seemed to be doing with them.

My new paramour, Arlene Keller, had met me in a high school English class. After five days of ignoring me, we got into bantering and I, foolishly, had boasted about my summer relationship with Molly. Of course, I changed her age to be the same as mine, but I mostly told the truth about how I had met her in New Jersey.

By the end of that Friday, we were on the roof of Arlene’s building, performing what I’d call mutual masturbation on each other. Maybe I should just call it a handjob and a finger fuck, but I hadn’t expected the abruptness of it all.

I had some sexual experience, but emotionally I was still a kid, unsure of my feelings about Arlene. With Molly, I wasn’t an adult either, but we treated each with respect. My first sexual contact with her had been abrupt too, but she was thirty-nine, a single mother (divorced), and a school teacher. I assumed that she would know how to handle me. Over the course of two months, I was proven right.

I don’t know much about that Arlene girl, and what little I had seen had been contradictory. My first impression of her was that she was morose about something, but it wasn’t easy for anybody to be fourteen. Her later sassiness or boldness seemed to be a bit faked.

Her precociousness had especially surprised me, but Molly had warned me that girls could be just as sexual as boys under the right conditions. I had just never seen that before for myself.

Molly herself was rather even-tempered, and I had never seen her in a truly bad mood. Arlene had already shown me that her moods were, at least, unpredictable.

When Arlene and I came down from her roof on Friday evening, we went to sit together on a bench on Pelham Parkway. For the first couple of minutes, it was a bit awkward for me and I suspect it was for her too.

Then she seemed to get her wits together and took the initiative again. “Hank, take me out for a date tomorrow, I mean a real date.”

It struck me that she was inviting herself to go with me, but that didn’t bother me. I figured I knew what a “real date” was, and I said, “We should go to Fordham Road and see a movie and then have lunch.” I made up the order of those activities on the spot.

She brightened and said, “Sure, that sounds great.”

Fordham Road was easy for both of us to get to, and I wasn’t ready to go with her on a longer Manhattan trip. “I have to check to see what’s playing down there.”

“Let me give you my phone number; get back with me when you get home.” She even had a piece of paper and a pen in her purse. I was getting the feeling that she was the kind of person who could handle various contingencies.

I said, “Okay, let’s aim for one o’clock then.” That was also an arbitrary decision on my part.

I was aware that Arlene was doing it somewhat backwards by asking for a movie date after we had performed manual sex on each other. But I had already experienced Molly’s very sudden seduction of me, so perhaps I could deal with unexpected events too.

And Arlene did have dinner or whatever it was with me before taking me to the roof. Molly had merely spoken to me on her porch bench for a short while before getting into some very wild and kinky activities that resulted in both of us having orgasms. That had happened in her living room. At least she had offered me a soda first.

Anyway, Arlene seemed more relaxed then, so we held hands and kissed for a while. At that moment, a normal, age-appropriate teenage make-out session seemed just fine.

That night I had to wrangle some extra money from my parents. I decided against telling them I had a date the next day. The only place I could have met a girl was at my new school, and I had only been there for a week. Instead, I told them I was going someplace with Mark, my buddy from junior high who had also been admitted to my specialized high school.

Another thing I had to be concerned about was picking a movie and keeping track of the film rating system which had only been in effect for less than a year. I doubted we could get into an R-rated picture that required anybody under seventeen to be accompanied by a parent or “adult” guardian. It seemed very unlikely that I could pass as Arlene’s guardian, adult or otherwise

The next level up was PG, which stated that parents were urged to give “parental guidance.” I remember joking with Molly about movie ratings, and how some kid might say, “Mommy, why is that man putting his penis into that lady’s mouth?” She appreciated my sense of humor which was one of the reasons I imagined I was falling in love with her.

It seemed that as the male I should just choose the movie and present it to Arlene as a fait accompli. I looked through my dad’s copy of The Daily News and found that an ideal PG move, Take the Money and Run, was playing at the UA Valentine. It was the first movie fully scripted and directed by Woody Allen. What could go wrong?

Being the worrywart that I tended to be, when I made my call I had to find out first if Arlene has already seen it and if she had even heard of Allen. I didn’t want to look for a fallback plan.

After I had presented my choice I heard, “Oh Hank, that sounds perfect.” Perfect! Maybe this teen dating thing wasn’t so difficult after all.

On Saturday I took the bus up to Fordham Road and met Arlene outside the theater. I was going to stick to my plan to see the movie and then have lunch. She had dressed up again, but her blouse, skirt, and sandals were not the same ones from the day before.

She was quite affectionate, and she held me and kissed me for a minute or so. Also, she seemed to be in a good mood, better than she had been during most of the previous week.

In the theater, we held hands, but I didn’t attempt any further moves on her. She obviously liked the movie and I did too. I’ve seen it more than once since then, and it had some memorable pieces of comedy. One of my favorites was when Allen and his escaped chain gang colleagues are in some woman’s house and they have to pretend that they are not all linked together.

Later, Arlene and I had a meal at a luncheonette down the street. Our talk was more natural than I had expected; we discussed our families and our former schools among other things.

Then, just after we had finished eating, she suddenly sexualized the conversation. “So, Hank, you told me some interesting things about this Molly girl you knew over the summer.”

I noted that she had used the past tense, which was probably a good thing. I needed to keep those two as far apart as I could. I knew what she meant, but I still said, “I did?”

Arlene showed no trace of coyness or shyness. “Yes, you described the oral sex you two did together.” She certainly was direct.

“I suppose I did.” Sure you did, you careless dummy.

“You both must have enjoyed it.”

Why deny it? “Ah yeah, we did enjoy it.”

“Well, Hank, now that you’re going with me, I’d like to do that with you, I mean what you’ve learned from her.” I realized that I must have been pretty convincing with my fondling of her the day before.

“When and where is this supposed to happen?”

“I think you already know that. I will be his afternoon, on the same rooftop where we were yesterday.”

I couldn’t help it, but I was blushing. I was also getting a rather insistent erection.

She had to do more thing to seal the deal. First, she put a hand out and held one of mine. Then she said, “I am wearing a very cute pair of panties today just for you.”

I almost said, I bet they’re getting damp right now, but I certainly knew enough not to say that. Besides, I could look into her face. She wasn’t smiling, but I knew what an expression of female arousal looked like when I saw it.

Then I thought, as I had previously, she’s offering you all sorts of good things. Go and take them.

I tried to be as casual as possible as I said, “Today sounds fine. I’m up for it.”

On the bus ride over to her neighborhood, she seemed bubbly, but she didn’t get excessively physical with me. At her building, she unlocked the lobby door and we rode up in the elevator. I remember the smell of lubricating oil from the electric motor.

When we stepped out on the roof, a feeling like agoraphobia came over me. It was earlier in the day that time, and I noted the vastness of all those roofs under a bright sky. She took my hand, and she led me to the same low platform behind the top of the elevator shaft.

Arlene immediately began to hug and kiss me as we stood there. I felt her hips rubbing against the front of my trousers.

Something changed in my mind and some of my nervousness left me. As we smooched while standing there, I thought, all right, the hell with it, let me be bold with her. If this girl wants to get down and dirty, then that’s just what I’ll do. In fact, I’ll start by doing whatever I please with her and see how that goes.

Thus, I did what I had always wanted to do with girls. First, I put my hands under her skirt, then into her underpants from below. I squeezed her buttocks, and she obviously liked that.

“All right, let’s see what those pretty panties you have been boasting about look like.” I put a hand into the waistband, and I just pulled them off her body. They fell to her ankles, and she stepped out of them. They was weren’t quite as skimpy as I had imagined but they were a nice pink with white dots.

“Do you like them?”

“Oh yeah, they’re very cute.” They were even cuter lying on the asphalt of the roof.

I ran my hands all over her lower body, squeezing and rubbing whatever part of her I wished to handle.

“Hank, that feels so good, I mean the way you are touching me.” She hung onto my shoulders, and she continued to grind her pelvis against me.

“Yeah, honey, that’s the way to do it, move those sweet hips of yours.” That was never the way I had expected to talk to a girl, but it seemed exciting anyway.

She giggled, “I can feel how stiff you are getting.”

“Part of it was those nice panties you were wearing. But, I want to see more.”

Without asking for permission or even mentioning what I was going to do, I unbuttoned her blouse and then reached behind to unbuckle her white bra. My experience with Molly had made that last maneuver, often troublesome for young guys, easy for me to do.

As her pointy breasts and nipples popped out, I bent down to put my mouth in position to suck on them. She moaned louder and continued to hang on to me. Then I went lower again, and I put my right hand between her legs and fondled her damp pussy.

All of those girls I had known who wouldn’t have anything to do with me; well, I’m getting my share now. They all had panties and vaginas under their skirts which I had never seen. Now I had this one giving me access to everything she had and she was loving it too.

In a few minutes, I was ready to move on. I wasn’t talking in my usual way, as I said. It wasn’t exactly that I was being rude, but I was being blunt and assertive in a way that was different from my normal self.

“Okay, Arlene, have a seat. If you want to get a pussy-licking, then that’s what’s just what I’m going to give you.”

“Yes, Hank, I’ve never had one before and I’m dying to find out what’s it like.”

“You’ll like it, I’m sure of that.”

She perched on the edge of her brick platform while I lifted her legs up and out. Her thighs felt warm and smooth under my touch. As I knelt there I put my mouth on her and did everything I had learned with Molly. Arlene was only the second woman I had ever tasted, and she didn’t seem much different. That was fine with me.

It was fine with Arlene too, based on the way she held my head and moved her crotch around. “Oh yes, this is just the way I hoped it would always be.”