The Wimp and the Deb - Cover

The Wimp and the Deb

 

Chapter 1

Romantic Sex Story: Chapter 1 - The story of a misfit but highly intelligent schoolboy and computer genius who has a fascination for a girl who is part of the richest family in the area. She is beautiful but seems to be a flighty socialite until circumstances change and she is faced with challenges she never expected, How are their lives going to interact and will there be a romantic outcome? Explicit sex may well form an integral part of this story.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   DomSub   FemaleDom   Spanking   First   Squirting  

Rory (The Wimp)

Hi my name is Rory McGregor and I have just finished my third year at High school in a small English town. You might as well know from the start the kind of guy I am. I'm a loner and a wimp, tall and skinny and probably less muscle than a jelly fish. I am an only child and live with my widowed mother. I can't talk to girls never mind date them. I don't have any friends and the most exercise I get is when my fingers flash across the computer keyboard. That takes me to the upside.

I may be tall and skinny but from watching other guys in the gym and in the changing room at the swimming pool I guess I am rather well endowed in my sexual organs. My cock is about seven and a half inches long and is so thick I can't lose my hand around it. Not that it does me much good since I am still a virgin, though I have to confess it does get regular exercise as I masturbate frequently. But I will tell you more about that later when I finish telling you about my other virtues.

I am also computer genius; I can hack into other computers with some serious safety systems. There are clever people out there trying to prevent people like me from invading their systems, but as those of you who have been struck down by computer viruses know there are also geniuses like me who can break through their safeguards and get into their secrets.

I am also brainy. I am a whizz kid at maths I stroll through physics and chemistry and languages come easily to my lips. I have never had anything less than an A in the whole of my school life. In secondary schools in England we start at the age of eleven and then in our fourth and Fifth year we study for our GCSEs and in the sixth and seventh year study for our A Levels. I don't expect anything less than A grades with any of these.

It is because of this that I won a scholarship to one of the best public schools in my area. Now that might confuse some people. Public schools in England are really private fee paying schools, the big ones like Eton, Winchester and Harrow are perhaps the most famous, but there are hundreds of smaller ones all over the country. Around Manchester where I live, Church Hill School is one of the best and always comes well up the academic league tables that are now published regularly. This means that there is always a great demand for places and to win a scholarship there is quite a feat.

A scholarship still places a demand on the parents of children attending these schools. The regulations regarding school uniforms are strictly enforced and have to be bought from the prestigious shops which are more expensive. Since we are pretty low on the income scale, it is fortunate that my mum cleans one of the big houses in the area and Mrs Barlow, her employer has a son who is two years ahead of me and goes to the same school. Mrs Barlow was delighted when my mum told her that her son had won a scholarship to her own son's school and she passes down his stuff to me. We must have been about the same height at each stage and my mum is a dab hand with the sewing machine so she can always adjust them to fit my slighter build.

It was this that led me into a life of crime. I did not mind being poor and the uniform meant that everybody dressed the same so you could not tell from appearances who were the really rich kids and who were the very poor. But other things gave you away like accents and not being able to enrol for certain school activities if you could not afford the extra fees that these required. Most people on scholarships integrated very well as their parents could afford to meet the extra costs and they had the social skills to make themselves acceptable to one or other of the groupings that form in any school or in any society for that matter.

However, as I said right at the start I was a born misfit. I did not fit in anywhere. This meant I got a bit of bullying in the early days, but the school had a robust anti bullying policy, so it never got out of hand. It was also helped in my third year when the son of the town's leading light and the star of our rugby team discovered I was a computer whiz kid. He was having trouble with his laptop crashing and had lost some material that he needed for one of his projects he came to me and asked if I could get it back for him.

I found out the reason why his machine crashed and fixed it. I was also able to restore the lost documents. After this he always spoke to me when passing and once or twice stopped at the place where I usually ate my lunch sandwiches to ask advice on how to do various things with his computer. Since His family were the main employers in the town and since a lot of the other employment depended on the success of their enterprises, this seemed to give me some kind of status and I was left alone.

You might be wondering how this led to my life of crime. It was one of the articles he was producing for his study. It drew attention to the fact that banks profited to the tune of millions of pounds from accounts that had been opened by people and then for some reason or another were left untouched. Perhaps it was because the person had died or moved away and forgot about it, or perhaps lost the details of it and being such small amount they could not be bothered going to the trouble of doing something about it.

Whatever the reason it seemed there were many such accounts. I decided to have a look at this and sure enough when I got through their safeguards I was able to access these accounts. I set myself a standard. If an account had lain untouched for twenty years and had less than one hundred pounds in it, then I would transfer that sum to an online account.

In order to be able to do this I opened an Isa on the internet. Isa's were tax free and would not attract the attention of the tax man as long as you did not exceed the yearly limit imposed upon them. Since you could only have one, I opened one in my own name and another in my mother's name and was able to deposit a yearly amount in each.

The limit at that time was around Five thousand pounds in any one year. So between the two accounts I could deposit ten thousand pounds in any one year.

I was not avaricious, however, and settled for much more moderate sums which enabled me to get anything I needed without bothering my mother. My desktop computer was now a state of the art and my mother, who knew nothing about computers, never noticed. My laptop was in the same category but had a battered looking case so that I was able to fool my mother into believing that a schoolmate whom I had helped with computing problems had passed it on to me because he had upgraded his own laptop to a much higher spec.

I rationalised this activity by telling myself that I was not really robbing anyone but the banks, who in turn were stealing the money from their customers by not chasing them down and making them aware that all this money was sloshing about in the banks coffers. To trace my activities if they ever found out about them we would have to go through so many false trails I had set up that they would need to be very clever to do so.

I told you right at the start that I was useless with girls. That did not mean that I didn't know anything about female sexuality. The internet is a wonderful place for learning about anything, including how to please a woman. There were sites that described female sexuality in all its intimate details with pictures and instructions on how to stimulate and excite them and I studied these avidly.

There were also the sites with erotic stories and again I was a regular reader of these also. I liked romantic stories, fantasy and sci-fi and bdsm, though I could never see myself being able to order a woman to do anything and totally lacked the confidence that would make such a lifestyle a possibility for me. That was certainly the case where the woman of my dreams was concerned. She was the daughter of the richest family in town, and the sister of Tom, the guy who had asked for help with his computer.

Their father seemed to have the Midas touch and everything he attempted succeeded even where others had failed. He had inherited a factory that made parts for the motor industry, and under his guidance they hand machined parts to tolerances that enabled him to win contracts from the Japanese for their factories in this country and gone on from that to export them to their factories in Japan also.

He had taken over a local group of failing supermarkets and turned them into places that rivalled the big multinationals in the area. He did the same with a chain of betting shops by upgrading them into the kind of places that punters wanted to spend time in and not merely bet. With the advent of David Cameron's government he was in the process of bidding to take over the role of supervising the community service sentencing programme.

His argument being that if he was allowed to privatise it, not only could he do a better job than the local council but because of the many businesses he controlled he was in an ideal position to offer jobs to one time offenders and thereby prevent them from reoffending. My bet was that he would get it and succeed in this too just as he had done with everything else.

This brings me back to his daughter, Rebecca McFarlane and my dreams. She is a fairly average student but the queen bee of all the social activities. She is also a very talented athlete in track and field and in the netball team. She also plays the flute in the school orchestra and is a leading light in the drama society. More important to my masturbation fantasies however she is about five feet eight tall with gorgeous long legs, a fantastic bum, and a neat waist, beautifully developed tits and a face that would have launched as many ships as Helen of Troy. In other words she is drop down dead gorgeous and way out of my league.

Hey, one is allowed to dream even if you know that the dream will never materialise. One thing is certain, I know that in the coming year she will still again have a central and a starring role in my fantasies. So it is back to school and the start of serious study over the next two years for our GCSE's. In those classes we share I will continue to ogle her behind her back and dream of the things I would like to do to her and for her.

Rebecca. (The Debutant: a socially desirable mate for a man of the same well to do class.)

My name is Rebecca McFarlane and I can't believe I am sitting here in this packed church crying. That coffin sitting in front of the altar contains my big brother whom I idolised and loved. He was everything a girl could desire. He was a hunk and girls threw themselves at him but he never took advantage of them. He had a steady girlfriend who would now be as devastated as I was. He was a great athlete, a first class scholar and the apple of my father's eye. He was being groomed as the heir apparent to all our business ventures and would gradually have grown into that role and would have been as successful as his dad had been.

My mum and dad were sitting beside me stony faced, but I knew that inside they were feeling the same grief and pain that I was feeling. At the end of the third week of his first term at university he had gone climbing in the Scottish Hills with the university climbing club. In my opinion a stupid macho sport if ever there was one. When I told him that once, he had laughed and said that some of the best climbers in the world were women.

The worst part of it was they had made the climb and were stowing away their gear at the top of the ascent when somebody had accidentally kicked his rucksack which then threatened to slide over the edge of the cliff. Instinctively he had dived to save it and slipped on the ice and gone over the edge himself. The mountain rescue people had got him to hospital in Fort William but he had been in a coma and a fortnight later he had died without recovering consciousness.

What a stupid waste of a brilliant young life and my heart was breaking. Our family has suffered the most tragic of losses and would never be the same. Little did I know how right I was and that for me, much worse was to come. On the second weekend after the funeral, my father had told me he wanted to see me in his study after breakfast. When I entered he was staring out the window with a haunted expression on his face. When he heard me enter he turned towards me and beckoned to a seat which had been placed in front of his desk.

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