Copyright© 2015 by Caractacus
Fiction Sex Story: Chapter 1 - His girlfriend had told him to take care of any "damsels in distress" while at college
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.
I started to unbutton her blouse, she reciprocated, undoing the buttons on my shirt. I hit a snag when I wasn't certain of how to deal with her bra. So I moved down to the button on her jeans, and lowered the zipper. We moved apart so that our shirts could be removed, and she undid her bra, before dropping her jeans and panties. I know its cliché, this was the first live pussy that I was ever looking at. Her light brown bush wasn't exactly sparse, but it wasn't in desperate need of a trimming just yet.
I pushed her down onto the mattress that we had made, and wanted to jump straight in, but she stopped me and said, "Slowly, I'm nearly ready, but you'll still need to get me there."
I remembered some of the in my mind mostly misinformation, that we had heard in sex ed.; it was technical, but never clued us in as how to make all of that technical work together. Basically, you could say it was knowledge without understanding.
I moved over to lie next to her body, and started kissing her tits. My hands were moving up and down her torso, playing with one tit and then the other, while I kissed, licked, and nibbled on the other tit. She moaned a bit, and I moved down, I was kissing her belly button, but could smell her arousal, that wasn't doing any favours to my cock.
My very inexpert ministrations were not enough to get her off, that first time I tried eating her. I licked through her labia, and tried to find her clit. After a while, my tongue was getting tired, and she decided to rather just pull me up, and let me fuck her. My diamond cutter, that's how hard it felt, sliced straight through her hymen. She shrieked, I suddenly realised what had happened, and I stopped. After a few seconds, she told me to carry on.
I started a slow in and out rhythm, but before long, I was jerking fast short jabs, I was on my way to getting my rocks off. I blasted inside of her. "Oh fuck, I didn't get you off, did I?" She was not the happiest looking of girls at the time. "I need to make this up to you, oh fuck, you are on the pill, aren't you? I never even thought about tha..."
She shushed me. "Yes, I am on the pill. And yes, I think that you do owe me. If you aren't willing to taste yourself, and maybe some of my blood, then use your fingers, maybe we could try for a second round."
The second round was infinitely better. After a quick shower, where we just played, I took her back to the mattress. I laid her down, before pushing my face into her pussy, and I asked, "Won't you tell me what to do, where to go, what you really like?"
By the time I actually got my cock back inside of her, I had gotten her off a few times, I had coaxed her clit out of its hood, and generally learned a bit more about female anatomy. The second go-around was also when she cleaned me afterwards, with her tongue, I got hard again, and then spurted a third time, this time into her mouth. She had also learned a lot more about the male body, including the fact that she was to keep teeth away from my dick.
When we rejoined the party, almost no one had even noticed that we had been gone, and that wasn't because we were the spares, but because everyone else had also been taking advantage of the situation – no parents, where we were all on our own cognisance.
Over the next close on a year, we went out fairly regularly, we got better and better with time. She relaxed, and learnt to enjoy my ever improving attempts at fore-play, and having realised that the best way to make me us better lovers was for us to critique our performance, and she would tell me how I could improve, inform me of what I could do to improve, to make her feel better, and I would do the same.
We continued going out together, until her parents divorced and her mother moved them back to her hometown, where her parents were.
Caroline and I had discovered several other aspects of dating, sex, and so on, together – things that could be just as important. After seeing something, we would discuss our mutual feelings regarding whatever had occurred – there was the almost-star baseball pitcher, who childishly constantly belched in front of everyone, who couldn't understand why the only girl who was willing to go out with him, was one of the tattooed, pierced Goth chicks. Or the star quarterback, who picked his dates up in a rusty old pickup, that was twice his age, with the front seat collapsing underneath him, let alone adding a girl on the bench as well (it looked like a ratty old piece of crud, but it hadn't been built to be a Rat Rod, it was just a piece of shit).
We had also discovered the joys of attending concerts, and plays, even the ballet and the opera, and visits to museums; this often meant dressing up, rather than just wearing jeans and T-shirt at the milk-shake parlour or the roadhouse, or ten-pin bowling at the mall.
I had then found myself subscribing to such things as men's style blogs on the internet. I was able to learn a lot more about what women might want, what they might expect, whether in a casual escort, or the man that they wished to marry. It wasn't just money, but the well-budgeted, well thought out use of it – stylish, but not necessarily expensive clothing; a smart-looking, but not necessarily 'SMART' watch, definitely no excess bling, a clean car – simple things that came with being a man, but it was up to me, as a man, to gain her attention, and keep it.