Over Hill & Under Dale

Copyright (c) 2003: All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved.

Writer's Note: Why does our society, which values professional counseling and training, leave sexual training to chance? What if inexperienced young men were mentored by sensitive mature women? This piece is purely fictional, and attempts to be entertaining, but all you guys and gals that read it, consider your own sexual experiences and relationships. Guys: what might have been different, if you had a tutor like Donna? Gals: under what circumstances would you be willing to coach an inexperienced sexual partner, as did these women?

Consider the usual warning: this story contains sexually explicit content. Do not read it unless you are an adult.

Chapter 1: Donna Is Recruited

The month of June was the beginning of the summer recess from my third grade teacher's job, and I was terribly bored. I couldn't afford a vacation trip, and my lover, Rob, a college history professor, was gone on a twelve-week archeological dig at some Mayan temple in the Yucatan. Fortunately, the rest of my summer turned into a very interesting and sexually satisfying time. For this, I have to thank Caroline, my close friend and condo neighbor, and her nineteen-year-old son, Dale.

The exciting time began over a Saturday lunch in early July, at Caroline's place. She is a single mom of forty, eight years older than I. Unlike my ex, who continues to be generous and supportive, her husband divorced her ten years ago, and left the state to avoid alimony and child support. Fortunately, she got a sales job with a software startup that took off, and she is now financially comfortable. About six years ago, she bought the condo next to mine, and we soon became close friends. I have enjoyed watching her son, Dale, grow from a skinny, confused adolescent into a very handsome, young man of nineteen. This May, he graduated from high school, and has a swimming scholarship from the University of Michigan. "Donna," Caroline said to me after taking a bite of her sandwich. "I'm really worried about Dale. Since last week, he's just been moping around the house, and night before last, while we were cleaning up the supper dishes, he told me that he's changed his mind, and now doesn't want to go to college this fall."

"Did he tell you why?" I inquired.

"Only after much prodding. It turns out that he went to a party at a girl's house last week. Three other boys and four girls were there with him, and, as I understand it, some precocious kids took advantage of the fact that the parents weren't home."

"Oh, God. Did they do drugs, or get into underage drinking?"

"Dale says no, and I believe him. What happened was probably nothing more than what you or I did when we were that age. Some of the boys and girls went upstairs to the bedrooms for some heavy petting or whatever. Dale is so inexperienced, when one of the girls approached him, he told me that he had no clue what to do. So he panicked and left, and now he figures that he is the laughing stock of his school crowd."

"Every boy and girl feels sexually awkward and clumsy at first, Caroline. Having a comfortable intimate relationship with someone takes practice, just like any other skill. Why is it that our society feels that young virgins will somehow have an epiphany and suddenly become good at something they've never before attempted? Did you try to tell him all boys have the same fears of performance? And did you tell him how good- looking he has gotten to be? God, with his swimmer's physique, he attracts me."

"I tried, but then Dale brought up how abusive and crude my ex, Kevin, was to me, and how I've tried the dating scene only to attract losers. He said that with his genes and upbringing without a father, he wouldn't be able to handle the pressure of dating and sex in college, along with the academics."

"God, Caroline, that is a humdinger of a problem. I assume that Dale has had the usual high school sex ed classes and knows the physical mechanics. Have you considered having a school counselor try to talk to Dale?"

"I don't think that Dale is going to open to any stranger about this problem. But I did discuss it with my older brother in Ohio. He was always great for me when I was a naive teenager and needed advice that a parent is incapable of providing."

"I depended upon my older brother in the same way, Caroline. What did your brother say?"

"He amazed me by relating a story of how he had a similar experience like Dale's, when Larry, that's my brother, when he was eighteen. He said that he really fell apart when he tried to make out with a girl and she laughed at his clumsiness. But then my mother's younger sister, Jessica, was sympathetic to his feelings, and she took it upon herself to teach Larry how to be a great sex partner."

Caroline took a sip of her coffee before continuing. "Larry claims that a few weeks of discrete coaching from Aunt Jess transformed him from a no-confidence loser into someone who could really turn on the girls. Until now, I never understood how it happened."

"That's an interesting story, Caroline. I never seriously considered it before, but I can see how effective it would be to have an experienced woman coach a young man in how to attract and please a woman. For generations, our society has been loaded with boys and men who act as if they are great studs, but who really are just ignorant jerks."

Caroline chuckled while I went on. "You and I have shared some of our own unfortunate episodes with clumsy men. For most of them, probably all they ever learned was from reading pulp novels and letters in adult magazines. I consider myself very lucky to have found Rob. He is the most considerate and pleasuring lover that I have ever had, and there were a number before we met."

"Unfortunately, Donna, there aren't too many guys like Rob, and it's probably because most guys never learned much when they were young. Imagine if every young man had some empathic woman who would coach him in how to become a great lover."

I thought for a moment. "If that could happen, there would be a helluva lot less unhappy women, and a whole lot fewer affairs and divorces, that's for sure. But that's beside the point. Why did you ask me to lunch today? You always do that when there is a favor to ask of me. And I do want to help, so just tell me what you want me to do."

Caroline blushed, hesitated for a few seconds, and finally spoke very softly, as if she were afraid to have me hear what she was going to say. "Actually, what we are talking about is to the point, Donna. The day after my brother told me about his tutoring from Aunt Jess, Dale and I were watching TV. It was some silly romantic sitcom, and I asked him what kind of woman attracts him the most."

"And what did he say?" I asked.

"He said, 'someone like Mrs. Hill.' He's attracted to you, Donna. And that's when I got this wild idea."

She took a deep breath, then looked imploringly into my eyes. "Donna, would you consider doing for Dale what Aunt Jess did for my brother?"

I choked on my coffee, astonished at what Caroline had just asked. "Caroline, are you serious? We are best friends and neighbors, and you're asking me to teach your son about sex! Think of all the possibilities and their consequences!"

Caroline put her hand over mine to calm me down, and let her speak. "I have considered, Donna, believe me. I think of the possibility that a normal young man is losing his self-confidence and esteem, the consequences of which could be a lifetime of unsatisfying relationships with women, or worse. I also think of the possibility that a woman, who is my closest friend and whom I trust with my whole heart, could be compassionate to the point of giving herself to this young man for the purpose of teaching him how to become a confident and sensitive love partner. The consequence of that is the brightest of futures for him."

What she said made me consider things from a perspective other than my socially conditioned upbringing. Caroline was correct: Dale, like so many virginal young men, had no way of becoming a skillful lover other than trial-and-error, and for most men, that resulted in lots of errors. And hadn't I just said to Caroline, at least philosophically, that early coaching could eliminate many unhappy relationships? Here was one of those opportunities to walk the talk.

I imagined how I would teach Dale to become a satisfying lover. My lack of sex from Rob's absence must have taken over then, for I began fantasizing how his youthful, trim body would feel coupled with mine. Caroline's voice brought me back to reality.

"You're considering the idea, aren't you, Donna?" she said with a grin. "You were smiling like the Mona Lisa. Believe me, when I thought of you and Dale, doing ..., well, you know, my first reaction was that it was outrageous. But then, the concept began to seem better and better. Here is Dale, very much needing help, and who is attracted to you, and here you are, a beautiful and experienced woman, who could be trusted to do all the right things."

She touched my arm with her hand, and used her best sales approach on me, anticipating my objections and emphasizing the attractions.

"The risks of discovery are minimal, Donna, since we are long-time next door neighbors. And only day before yesterday, you admitted how horny and bored you're getting with Rob away. Just imagine how exciting it could be to get it on for the summer with a young hunk. It would do your libido a lot of good, as well as be the greatest gift you could ever give to Dale and me."

"Well, Caroline, even though I have to admit that the idea is beginning to intrigue me, I'm still not certain. There are so many things to consider. I know one thing for sure: I absolutely refuse to try and seduce Dale. He would have to understand completely that his experience with me was only for the purpose of his sexual training."

Caroline persisted until I agreed that she and I would broach the idea to Dale that evening, over dinner at my place. There were quite a few blushes and h'mm's and err's before the two of us coherently communicated to Dale what we proposed. When he eventually comprehended what was offered to him, it was very touching and endearing to see how relieved and grateful he was.

"Oh, gosh, Mrs. Hill!" he gushed. "You are the greatest. I'll do whatever you ask, or tell me to do. And I do understand – no one other than us three will ever hear about this. Thanks ever so much, Mrs. Hill. When do we get started?"

After I saw the look on his face when he realized that his problem had a cure, I knew that I was going to help this young man, no matter what others might think. I smiled reassuringly at Dale, then at Caroline.

"Well, Dale, I'm not yet sure how, let alone when, to get started. But I'm a trained teacher, and this is certainly a form of teaching. So I will do some research and create a lesson plan, much like I would for any class preparation. Give me, say two weeks, and then we'll begin."

"That's OK for me, Mrs. Hill. The only summer obligation I have is my training and competition at the swim club, but I get home by noon. What works best for you?"

I smiled at him, touched and flattered by his eagerness. "I think that our kind of training is best suited for evening hours, Dale."

For the next two weeks, I used the Internet and the local library to research the topics of human sexuality and clinical sex surrogates. I developed a lesson plan and training strategy for myself, and a reading list for Dale to study. I also made a list of things I wanted Caroline to do. When all that was completed, I went to Caroline's place in the evening to talk to her and Dale. I described my lesson plan, with its goals and steps, and what I expected from them. We agreed on Tuesdays and Thursdays for each week's training sessions. Dale was eager to get started, and both he and Caroline agreed to their parts in my plan.

I rose from the chair in their living room, and gave Caroline a hug before going over to Dale. "Before I leave, Dale, let me ask you a question. Do you notice anything different about me tonight?"

Dale stared at me in confusion, his eyes scanning me head to toe. I noticed that his stare lingered on my breasts and hips. To give him a hint, I put my hands on his face, and made him look me directly in the eyes. "What difference do you see, Dale?" I asked again.

I could see the light of recognition in his face. "Your eyes!" he exclaimed. "They're blue! You're wearing colored contacts, and you also have used violet eye shadow. You look beautiful, Mrs. Hill."

"Excellent, Dale. A caring man always notices the things a woman does to make herself more attractive to him. And it will be important that anytime we meet, you notice my eyes. Whenever you see me wearing these contacts, and this shade of eye shadow – you think of me as Donna, your girl friend. Any other time, I am Mrs. Hill, the lady next door. We can't have any embarrassing mistakes in this, or some terrible gossip may develop. And also, Dale, when these sessions are over, you'll never see me wearing these contacts and eye shadow again, ever. Do you get my meaning?"

Dale nodded, and Caroline hugged me once more. Then she went to her son, and tenderly kissed him on the cheek.

"Dale, honey, you are so lucky to have such a wonderful girl friend like Donna. Just do whatever she tells you, and enjoy this summer. Oh, and if ever I ask what you and Donna did, you just tell me, 'Mom, I'm an adult, and it really is none of your business.'"

I returned to my place, thinking about my new male protégé. Dale is just over six feet tall and about 170 pounds, with the hard muscular body of a champion swimmer. He has dark hair, worn neatly just over his ears, with a great tan and flashing white teeth. "He is going to excite quite a few female hearts and bodies," I thought. Later, before falling asleep, I could sense my own body warming from dreams of being his first lover and how I would teach him all the little things that get me highly orgasmic.

Chapter 2 Lesson One - Training Begins

I first needed to get Dale's self-esteem improved, and also to become comfortable with me as a girl friend. For that, we spent the first week's two sessions in shopping for a complete change in Dale's wardrobe, from shoes and shorts, to slacks and shirts. Since I was supposed to be his date, I let him drive my Miata to the mall. On the way on Thursday, I expanded my lesson from just shopping.

"Today, we have two objectives, Dale: completing your wardrobe, and practicing how to approach women to get them interested in you. So let's begin with talking about clothes."

By the time we reached the mall, he understood that he is an autumn, and the brown hues best compliment him. Once in the men's department of the mall anchor store, I deliberately made Dale make his own selections, encouraging him to act on his own, and to begin thinking of himself as a young adult, not a high-schooler. There were a few times when I had to be critical.

"Uh, uh, Dale. Tight pants and jeans were designed for riding horses, not getting romantic with a girl. Think how awkward it will be to take off your pants, if she gives you the go-ahead. Hopping around the floor, or sitting down and tugging will be a huge turn-off. Now, go back and look some more, and show me how much you've learned."

This time, he came back to where I was sitting wearing an outfit of olive colored Dockers with pleated front, topped with a tailored sport shirt of muted brown-orange plaid with button-down collar. He had also replaced his jogging shoes with brown tasseled loafers and tan socks.

"Oh, my, Dale! What a terrific outfit that is. Now you look like a real collegian. This weekend, I want you to get some more clothes like that. So now, let's shift the lesson from clothes to work on the skills of approaching and attracting a woman. I am going to go to the Food Court and get myself a cola. We'll pretend that we came to the mall separately, and that you are interested in dating me. Your challenge is, in the next ten minutes, think of how you will approach me, and get me interested in you. And I must be interested enough to agree to go off someplace with you, so you can ask me for a date."

"Dating rule number one, Dale: what you say when you first approach a girl, is very, very critical. Guys can be so clumsy or corny then. The wrong words, and most women will just think, 'get lost, loser.'"

"That's my whole problem, Donna. I never know what is the right thing to say at that moment."

"There is no one right thing, sweetie. You just can't have a dumb line. What I want you to do is think of some reason for you being in the Mall that will make a girl, namely me, begin to appreciate your inner qualities. To do this, you must keep the conversation on something that shows that you are interested in her inner qualities as well."

"As a trick, Dale, never ask her questions that can be answered with a word, or yes or no. Always begin with something like 'What do you think,' or, 'Why do you suppose.' That way the other person is being drawn out, and you are showing that you're interested in what the other person thinks or feels."

With that last piece of advice, I left Dale to get a coke at the Food Court, and sat at a table to await his return. I was halfway through my drink when I noticed him threading his way around tables and chairs. He looked my way, flashed one of his turn- on smiles, and waved.

"Well, hi there, Donna. How nice to see you once again. What brings you to the Mall today?"

I tried to pick up on his play-acting. "Oh, hi, Dale. I'm just trying to find some good summer sale bargains."

"What stores have you been in?" Dale asked. "I noticed some neat tank tops and low-cut shorts in Kohl's that would really look good on you. Say, Donna, how much time do you have? I have a small dilemma, sort of, and with your good taste, you could really help me out."

"Well, I'm not sure, Dale. What's your dilemma, and how do you think that I can help?"

"It's like this, Donna. I want to buy my mom a little gift, just to try to say how much I appreciate her. I know that she likes aromatic candles, but I'm not sure what aromas women like. I know that whatever you'd like, my mom would, too. What would it take to have you go with me to the candle shop in the East Wing, and pick out the perfect scent for her?"

He gave me another of his dazzling smiles, and I spontaneously jumped out of my chair and hugged him.

"Dale, honey, that was just great! You have a future as a salesman, just like your mom. I especially liked your last question. It never really gave me a chance to say no, and why would any girl not want to go with you to show you what scents she likes?"

Dale was delighted with himself, and his confidence jumped up enormously. He looked straight into my eyes. "Hey, wonderful blue eyes, what would it take to get another hug? This time, I'll be ready for you."

I laughed, and gave him a more ardent embrace, pressing my breasts into his chest. I took his hand, and we walked out of the Food Court. Along the way to the candle store, Dale occasionally stopped to point out something in a store window, asking my thoughts and opinions about some object or if I admired its design.

After purchasing a candle for Caroline, following my recommendation of the aroma, we left the Mall and returned to my place. We sat together on the sofa in the living room, sipping a soft drink and chatting about the lessons at the Mall.

"It was a very productive week, sweetie," I said. "Your blue-eyed girl friend is very much impressed with how quickly you picked up on my coaching. With your new appearance, and your confident style, it should be easy to attract girls on your own." "Donna, you are so easy and comfortable to be with. But somehow, it's different with the girls my age. Oh, I apologize, I didn't mean it the way it sounded."