Painfully shy couple take first tentative sexual steps

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My parents got divorced when I was 8. My older sister wanted to stay with my Mum. Whilst, surprisingly for those times, I chose to live with my Dad. For a few years we muddled along together until, when I was 11, he met and moved in with his new partner, Jayne.

It was, as is almost invariably the case, a difficult transition for us all. But I grew very fond of Jayne. My Mother (and my sister) had been a little brash and forward. Whilst my Dad was calmer, serious and much more reserved. And I was, in many ways, a carbon copy of him.

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Jayne was a much better fit for my Dad. And, as I came to realise, probably for me too. She was quiet, almost diffident. Dressing and acting very conservatively.

So, at the age of 18, in my final year of school, I was happy and contented (though sexually frustrated) with our current living arrangements. Certainly happier than I’d been when my parents had been constantly rowing a decade or so ago.

I went to an All Boys grammar school in our small town. It selected on academic achievement. So it probably contained more than it’s fair share of studious, socially awkward, pupils. But, even by those standards, I was an outlier.

I was in the top 10% academically. But in the top 1% for shyness and clumsiness around girls. I loved the opposite sex. But I had absolutely no idea how to talk to them. Probably because I had absolutely no confidence at all in my physical, or particularly social, prowess.

Jayne came with a “plus 1”. She had a daughter, Sally, her only child from her previous marriage.

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Sally fitted in well to our rather dull quartet. She went to the equivalent All Girls grammar school. Sally was just a few months younger than me and we were in the same school year.

Probably taking a lead from her Mum, Sally did nothing at all to enhance her looks. Her dark, almost raven black, hair had a corkscrew perm. And huge, “milk bottle top” spectacles. Both of which, looking back on, even years later, she still cringes about. Her skin was pale and (unlike my acne scarred complexion) almost perfect. But, because her hair was so dark (and as I was to discover she was quite hirsute) it showed on her arms and legs. Which I came to realise she was really embarrassed about. All of that said, strip away the dodgy perm, glasses and unwanted hair and beneath it I suspected (and subsequently came to discover) she really was extremely attractive.

What she did have, though also did her best to hide, was an absolutely killer body. Partly genetics I guess. But also, in large part, down to the hours she spent swimming competitively each week.

I can clearly recall going to see Sally in a swimming gala. As she stripped off her tracksuit and took her place on the starting blocks at poolside I was astonished how shapely and womanly she looked. Everyone competing was fit. But I honestly thought Sally had the best body of them all.

Whilst we were not blood relatives, the character similarities between us were uncanny. Sally was bookish, extremely clever and hard working. She also, like me, seemed to lack any confidence about her looks. And was painfully shy with boys. So there were certainly no boyfriends on the scene. In fact, she seemed to have few close friends at all. The two of us, I’m afraid to say, were rather “grey” characters. Largely in the background, certainly in social settings.

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