Chapter 1

That summer, the summer of the year between high school and going off to college, was fun. I rebuilt a car, with the help of my father, my uncle, and a neighbour, who happened to also be my best friend. Jerry has been my best friend since about second grade, when we moved into their neighbourhood. In a way, I was almost afraid to tell him about the fact that I had taken his sister's cherry, and when I wasn't with him, I was spending my time with her. She was going into her junior year, just turned seventeen.

My name is Robert MacDonald, most often just called Rob. I am about five foot eight tall, and might not grow very much taller. I weigh about a hundred fifty pounds, my build not too athletic, but I was slim, rather than weedy. My hair is dark brown, but when I look at both Dad and Uncle Jack, mom's brother, I know that there is a good chance that what is not grey will be bald and what isn't bald will be grey by the time I am in my mid-thirties. I was just about to turn nineteen, myself, in a little over two months' time, and was on my way to college.

Rachel, a month or so ahead of her seventeenth birthday, had come onto me several weeks before graduation. She claimed that she had had a crush on me forever, well at least for the last eleven years, since I had moved in next door.

By third grade, since we went to the same school, Jerry and I had to escort her to school, she was going into first grade; of course we were boys, had no time for girls, yet ... and she was (in our minds, at least) a spoiled brat.

By the time that Jerry and I were going into our junior year, I had already lost my cherry. While I was not a jock, I mean I swam, but I wasn't on any of the ball teams, but neither was I a nerd, although I came consistently in the top ten percentile of our grade (that was in the whole school district), and I did play chess; but I hung out on the fringes of the popular crowd.

That may have been due to Jerry's being on the JV football team, him being a jock. And where he went, I was able to also go. That is not to say that we were anything other than friends; we were equals, brothers-in-arms, and the rest of the team accepted me. I was always included at parties that the real nerds could only dream of. It was at one of those post-game parties that we both lost our virginities; Jerry had gotten Sally, a cheerleader; while Caroline, her best friend, not a cheerleader, but like myself not quite falling into the nerd category, had decided that I was possibly her best choice. I never told anyone about us, I felt that if I could spread rumours about her, then I would deserve to have the honour of being on the wrong end of any reciprocation.

Caroline was what might be called a plain Jane, she was pretty, but not stunning. She had mousy blonde, brown hair, worn shoulder length and straight with a slight curl at the ends, and brown eyes. While her face was oval, and fairly unremarkable, she did have a body of note. She stood about five foot five in her bare feet, and probably weighed close on a hundred and ten pounds. Her C-cups complemented a gorgeous hourglass figure. Her biggest problem was a matter of self-esteem, with a more outgoing personality, she could have been a cheerleader herself, and she actually wouldn't have needed too much makeup to pull it off either.

Hey, I wasn't exactly Mr Gregarious, myself.

Our first experimentations were awkward to say the least. While she had this idea that there might be a chance that I could be gentle, she didn't trust me enough to relax in my presence. That first time, I think I may have hurt her, but she never said anything.

The party was taking place at Ed's house, Ed was the team captain, and his parents had gone out, allowing him to have a small private party. Sally was a new cheerleader that year and had brought her best girlfriend to the party. I had accompanied Jerry, this year's new starting running back. There were seven couples after Jerry and I split, and got together with a girl each.

I had had a small sample taste of the punch, it had a very bitter aftertaste, and almost immediately I was feeling a head rush, and when Caroline asked me to get her some, I didn't quite refuse, but I did comment on the fact that it might not be the best idea, and since we were already keen for each other, were we still needing any extra Dutch courage.

She agreed, and led me to the poolside cabana, and I spread out some towels and the chaise cushions on the floor. Caroline was a little nervous, but she wanted to do this. She asked me if I had ever had a blowjob. I answered in the negative. She said, "well, I have never given one either."

The naïve "nice person" virgin inside of me was about to tell her that it wasn't necessary for her to do anything she didn't want to do; while the "never even been kissed" teenager wanted to shout "whooee!!!" My internal debate didn't take long, before I asked her, "is there anything that you have done?" At the time I wasn't thinking of how rude or insensitive a question could be.

She seemed surprised, and maybe a little hurt, probably that the boy she had chosen for this all-important event might have been trying to backtrack, but my mind chose just then to get fully engaged in what was happening, and I asked her, "do you want to be eaten? Why don't we do things together, why not share with each other?"

Her face brightened. I stepped closer to her, and lifting her chin, I kissed her. Her mouth opened up, my tongue invaded, and then our tongues were duelling. It was then that I realised that most porn, or at least anything that I had ever seen, didn't show us how to get from the clothed state to undressed, and definitely not how to do it with any semblance of dignity. I was in unfamiliar terrain.