This is a sequel to
The Kinky Mrs. Grunewald.
I decided to post it in two parts.
In this part: After his abrupt, strange, and highly-charged BDSM encounter with his mature history teacher, high school senior Tom D'Amato has a leisurely conversation with her over drinks. He is one of a handful of scholarship students at an expensive private school, and he has never felt comfortable there. He is too naΓ―ve to realize how common older-women/younger men matches are, even if many of them don't last very long.
The second part of the story is about his next visit to her office on the following day, which I will post very soon. That contains the actual BDSM scene plus more. The location for this is in New York in the late spring of 1973.
******
When we got to the bar, I was still feeling uneasy, but Judith looked quite calm and composed. How many times had she been involved with students at the school? There was a yearly rotation of male seniors she could pretty much grab at will. I suspected that they didn't put up much if any resistance to her charms, especially if she used the bogus punishment lure that she used on me.
Are all men are basically sluts? I had read that from a woman writing somewhere. I knew I could easily be had by Mrs. Grunewald, and it wouldn't take much more prompting on her part. We were already into the initial stages of our affair. As soon as she had demanded to spank my bare behind, I had felt the first quiver of anticipation. It was really an offer in the form of a demand that she had made to me when I first entered her office.
I didn't have too much experience with alcohol, but I was glad to have it available for that meeting with Judith Grunewald later. I had never been on a date before and I wasn't used to sitting alone at a table with a woman, much less someone Judith's age.
It was a strange date, one in which we had already engaged in the first sex act, namely me ejaculating onto her lap. She had talked me into that first, and then later she had brought me to the bar. I was aware that she was in charge of what was happening between us. I wasn't sure I was comfortable with that, but I had no choice. Maybe I liked the situation more than I would admit to myself.
I thought,
just relax, you're going to be okay with whatever she comes up with in the next few days.
It some ways it was preferable to deal with an experienced, mature lady rather than a girl my own age who knew as little about sex as I did. If that had been true, I suspect there would have been a lot of fumbling around on both our parts.
Judith ordered a cosmopolitan while I perused the liquor menu. The simplest thing would have been to get a beer but I figured that I would look a bit unsophisticated with one of those. She must have noticed that I was a bit puzzled because said, "Why don't you just get a Manhattan?"
"All right, that sounds good." I had heard of the drink but I had never had hard liquor before nor did I know how that particular cocktail was made. We chatted briefly about school topics until our drinks arrived. Mine was in what looked like a martini glass; it contained a dark liquid.
She must have noticed my expression, because she asked me, "You do know what's in it, right?"
"Of course I do."
As I would notice later about her, she seemed to know when I was fibbing but she wouldn't call me out on my attempts to appear more worldly. Instead, she simply told me the main ingredients. "It's got rye whiskey with vermouth and a few other things. It's pretty strong, so go easy with it."
I wanted to know what was in her drink but I wasn't going to ask her. I tasted my own and it seemed pretty good. After we had sipped our drinks for a few moments, she pushed her glasses to the top of her head.
I knew why she had done that; she wanted me to see her uncovered face again. I tried not to flinch from her gaze. I was still unsure of how I should deal with her, but I had already gained -- perhaps not quite confidence, but maybe I'd call it a little assertiveness about being with her.
After all, she had given me an orgasm that afternoon, which was pretty heady stuff for a guy my age. Well, I arguably gave it to myself, but her spanking my ass at the same time had sexually inspired me. I wasn't in the same state of mind as when I had walked into the building that morning.
I noticed again that Judith wasn't a delicate-looking woman, and that went for her face too. Of course, I tried to imagine what she looked like twenty years earlier when she was near my age. She gave me a few moments to look back at her, and then she said, "I guess I owe you my age. I mean I'm not one of those ladies who makes a big deal about it. I'm thirty-nine right now."
I did a quick calculation in my head, and I knew she had probably been a high school senior around 1952. She was still pretty good-looking, but I concluded that she must have been stunning back then. It struck me that had I been that age at the same time, she likely wouldn't have had anything to do with the likes of me. Now that she was older and probably lonely, maybe a young guy like me didn't look like such a bad deal, even for a fling.
Rather than dwell on that, I said, "So your college class must have been, what, 1956?"
"Yes, I was Barnard, '56." That was the year after I had been born, in fact.
Yet I was impressed, "Barnard is a really good school." Had I had been older, I would have been more careful about giving out compliments.
She shrugged, "Well, we all had to go somewhere." Perhaps I appreciated that she wasn't bragging about it. Then she said, "So Tom, could I ask you a few things, mainly about your experiences at Pierpont? These questions might seem a bit personal."
I tried to appear relaxed too, even though I didn't feel that way. "Sure, go ahead."
"Well, I've noticed that your, ah, dating experiences at Pierpont have been pretty much non-existent."
How the hell did she know that?
I didn't realize that women were usually well attuned to social circumstances like that one.
"No, I've had a few dates." I didn't say where or with whom.
As before with the drink ingredients, she knew I was fibbing, but she pressed ahead. "Most of the girls at our school are pretty stuck-up, although they try to pretend that they're not. I know it can be a bit difficult for the scholarship students here, and there are only eight of you in your class."
She had pinpointed one of my issues with the place. I complained about it, "Right, and only one of them is female, that Cynthia Brillstein girl. I've tried to chat her up, but I haven't gotten very far."
"And she's painfully shy, I know. But, in any case, you don't know how to approach women."
That rankled me a bit. Yet the truth was that Judith had approached me, although in a very unconventional manner. "So Tom, what do you think of me, I mean as a woman?"
How am I supposed to answer that?
I didn't realize that this was a common test women would use on men, although perhaps it was a bit unfair to use it on somebody my age. Probably it was purely instinctual of her part.
Anyway, I didn't want to say that I had spun some fantasies involving her already. At eighteen, one will masturbate about just about anyone who might be plausible. I answered as honestly as I could. "I'm not sure. I guess I mostly thought of you as my teacher."
"But I'm not just your teacher, am I? I mean, this afternoon I saw, well I saw you climax and it was quite a sight to behold."
Wow, that was pretty blunt.
From the way she was grinning at me, I knew she didn't mind getting me somewhat rattled. I did my best to hide it with a joke, "Well, you certainly did your best to make it happen." I almost couldn't believe I had said that, but she chuckled and seemed to take it very well.
"And you certainly enjoyed every moment of it!" Right then, she ordered another cosmopolitan.
Yeah, like you need another one of those.