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?"
