Call me Lenore. I have a story to tell that might interest you. It’s about the steps I took, after years of self-restraint, to become sophisticated about sex. It involved engaging an older man that I’d fantasized about for years to be my mentor and guide. To be honest, I seduced him, overcoming some initial reluctance and doubt on his part.

I’ve been curious about sex and interested in it since before I can remember. By the time I was in high school, I had seen pornographic videos on the computer in my father’s home office. By that time, I was also masturbating regularly as well. But the interactions I had with boys were very unsatisfactory. They seemed clumsy and crude. I couldn’t imagine doing things with them that I’d seen on videos. In my fantasies, my lovers were older, smarter, more sophisticated. They also had much bigger dicks than the couple that I’d had in my hands. I was so disappointed in my experiences with boys my age and a little older that I stopped making out with them and developed a reputation as being cold, or perhaps even a lesbian.

There was one man in particular who frequented my dreams. He was a tall, slim man in his 40s who was known by all as the Professor. He had a couple of kids who were a little bit older than me. Adding to his interesting qualities was a personal tragedy – his wife had died in a traffic accident. That was when I had first heard about him.

I looked him up and found a lot of information about him on line. He taught at the law school in the big university in the next town. In addition to a law degree from Penn he had an Ll.D. and a Ph.D. in economics, both from the University of Chicago. He had written an important book on law and economics that was used as a text both in law schools and in graduate programs in economics. It especially excited me that he was such a smart man.

I occasionally saw the Professor in the pharmacy where I worked part-time and in the summers as a cashier and stocker. When I checked his items and rang them up at the cash register, I always smiled and greeted him as Professor. He didn’t know my name but always smiled in return and asked how I was doing. One of the items he bought regularly was condoms – and it made my pussy tingle that they were ultra large size. I’m sure I blushed ten shades of red the first time I rang that item up for him. In addition to the tingle, I was always conscious of how wet my pussy got – that was a reaction that never stopped.

One day not long after I graduated from high school, I encountered him in a local park where I was walking my dog. He had obviously just completed a long run and was relaxing on a bench, doing something on his phone. He was wearing jogging shorts and a t-shirt, both of which were soaked with sweat. It didn’t escape my attention that there was a large bulge in his shorts between his legs. I stood near him and asked if I could talk with him. He glanced up, smiled when he recognized me, and said, “Let me just finish up this message to one of my students.”

This is what he saw when he finished his message and looked up at me.

He smiled and said, “I know you – you’re the young woman who works at the pharmacy.” Then he sort of purposefully looked me up and down, from my eyes to my breasts, to my legs, and then back up to my eyes again. “What did you want to talk with me about?”

“My name is Lenore. There are several things...” My face felt hot, but I had decided what I wanted to say to him when I had the chance and had even rehearsed the exact words. This was my chance, and I wasn’t going to let it pass by. “There are things I think you could teach me that I’ve decided I want to learn from you and from no other man.”

“I’m not sure what you mean,” he said, while carefully looking me in the eyes. But his eyes narrowed a bit, which I took as a sign of either interest or wariness. I hoped it was interest.

I sat on the bench near him, and my black lab, Bruno, sat down too. He was looking at me as intently as the Professor was.

“This will sound weird, but I hope it won’t offend you.” I looked down at my hands, which were folded on my lap – and then I rushed on. “I have fantasized about you since I was just a girl. I want you to teach me what it means to be a woman.” I looked into his eyes and saw them widen. I had definitely gotten his attention.

“Hmm.” He said – and paused. “Look, ah, Lenore, you are a lovely young woman. But I have a girlfriend. And you are way too young for me. How old are you, 20?”

“18, actually, and I have very little experience. But you are the one I want to become experienced with. I want you to be my first.” I paused for a minute, then added, “I know what it means that you buy those particular condoms, and I want that.” I couldn’t help looking at his crotch and noticing that the bulge had grown noticeably larger.

When I looked back into his eyes, he looked away and thought for a minute. “Your offer is certainly enticing. YOU are enticing. But I’m hardly an expert in what you are talking about. Wouldn’t you be better off having someone your own age be your ‘first,’ as you call it?”

“The boys my age are clumsy and awkward, and they seem pretty stupid. I know that you are more of an expert than they are. And I mean it that I have wanted you since I first knew what it meant to have those feelings.”

“Look, I need to get home. Let me think about what you’re saying. You are an appealing young woman and obviously a very smart and thoughtful one at that. But you are very young. Most people would think it was highly inappropriate for me to be involved with you in the way you are suggesting.”

“Can we exchange phone numbers so that we can arrange to talk again some time?”

“Hmm. I’m not willing to give you my phone number. But I will give you my personal email address. It’s wardfranklin78 at gmail.”

“That’s w-a-r-d-f-r-a-n-k-l-i-n-7-8 at gmail?” I asked, spelling it out.

“Exactly right,” he smiled in a not-unfriendly way, got up, and walked quickly in the direction that I knew was his home.

“This is perfect,” I thought to myself. “I know exactly what I’m going to send to him.”

That night I wrote to him.

“Dear Professor Franklin,

“Thank you for talking with me today. First, I want you to know that while I am perhaps a bit obsessed with sex, I’m not just some sex-crazed bimbo. I just graduated as salutatorian of my class and was admitted to all the colleges where I applied. I will be going to Penn’s Wharton School in the fall. There are a lot of ways that knowing you would be good for me. My mind is on one way in particular – but that isn’t the only thing that is important to me and isn’t the only reason I admire you.

“It wasn’t easy for me to say the things I said to you, and they must have seemed highly unusual and perhaps inappropriate. But I want you to know I have been thinking about you and fantasizing about you for years – for as long as I’ve been thinking about sex. You are the reason the boys I know seem stupid and clumsy – I always compare them to you.

“You asked about my age and told me I am very young. Yes, I am young, and inexperienced. But I am not a child. I’m old enough to know what I want. And I will not give up easily.

“A few months ago, I went into that shop out on Rt. 1 and bought myself a toy to play with, something I thought would give me an idea of what it would be like to be with you. Here is a picture of me playing with that toy.

And here is another:

“These pictures are so you will see that I am totally available to you. While I have never had a cock in my vagina or my anus, I have had that big toy in both of those openings. You can see by the look in my eyes that it was you that I wanted inside of me – and I imagined it really was you. It felt good – but I know it will feel even better when it is the real you instead of an inanimate toy.

“I have watched a lot of porn and know what men want – and I have reason to believe that you are no different from other men in that respect. And I want you to teach me how to suck your cock too.

“To finish where this message started, it isn’t just your big cock that I want. You are a brilliant man, and I believe from observing you that you are a kind and considerate one as well. I hope to have a relationship with you for a long time. And I want that relationship to begin with you helping me to become a complete woman.

“Respectfully,

“Lenore”

It was several days before I heard back from him – long enough that my fears of being rejected had grown into a near conviction.

But finally, about a week after that meeting in the park, the following email message came to me.

“Dear Lenore,

“I’ve been grappling with my thoughts about you. There is no question that you are a desirable woman, and that you are grownup and womanly in some very conspicuous ways – but you are much younger than the women who usually attract my attention. Consequently, I have very confused feelings about developing a relationship with you. The world would say the sort of relationship you have in mind for us is not just inappropriate but unconscionable for a man in my position, a man who teaches young men and women who are older than you but still in many ways too young for me to engage in a relationship with.