Foreword: This story is partly true and partly fantasy. It is something I regularly think about even 30-40 years after the events that I will describe. There's a bit of background and it may take a little time to get to the "good parts". But the background is important I think.
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Like most other teenage boys, the first "experience" I had with anything sexual was through pornographic magazines. I guess I either looked old enough, or the owners of the shops that sold them were turning a blind eye, because I was able to buy them without any real problems. And while I liked looking at the photos, I was mostly interested in the stories. The stories that mostly did it for me were the "reader's wives" stories. Maybe it was the forbidden fruit, or the nature of the girls may age, who used to blow hot one day and cold the next, or the fact that I was very much an ass man and I loved a shapely bum.
I also had a bit of a crush on one of my teacher's wives at high school. We had guidance councillors and he was also my guidance councillor. And as he lived very close, I would generally go round to his home for our meetings. I even did a few odd jobs around his house and in his garden. His wife, Mary, wasn't what you might call overly beautiful, but she had a great ass. She also had a nit of a bitchy air about her. In fact, as schoolboys do, we would comment about her, with a couple admitting they fancied her, while others said she was a bitch and they wouldn't be seen going near her (though probably, they would all jump at the chance, to be honest). Her husband, Jack, liked a drink. And, thinking back, and based on a later experience (which is the actual subject of this story), it's possible that she came across as a bit of a bitch because he couldn't satisfy her, due to his drinking (or that's how ı like to see it, when looking back and wondering what might have been, given the right circumstances).
Anyway, this story isn't about her, but she was one of the major reasons I got interested in (or actually became infatuated with) older women.
This story is about a very close friend of my mum's. Nicola was a couple of years younger than my mum. And my mum had given birth to me when she was only 19, so I guess there was only 15-16 years age gap between us. My parents use to hang out a lot with her and her husband, Alan. They also had a small son, who was a little bit of a handful. Alan also liked to drink, and much more so than Jack. In fact, it was no secret that he would start with beer early in the morning and move onto harder stuff as the day progressed, when he wasn't working. (In fact he ended up changing jobs a few times - more than likely due to his drinking problem).
Alan and Nicky used to argue a lot. And these were huge fights, in front of everyone. Nicky was a very fiery woman. We got used to seeing them like this. And I actually felt grateful that my parents weren't like that.
As I was growing up and reading stories about cheating wives and noticing how sexy my teacher's wife was, I also began to notice Nicky in a different way. She used to wear fairly tight pencil skirts that rode up above her knee when she sat down. These skirts accentuated her legs and her bum, which was the sexiest bum I (in my short life) had ever seen. So, naturally, I looked. I stared. And her attitude towards me changed too. I guess she must have noticed me staring and realised that I was no longer a little boy. That's when the mild flirting started. It made me embarrassed at first, as it was generally with my parents in the same room. And ı was too young and naive to know how to deal with it. But it did give me a lot of masturbation material.
There was always music and dancing when they got together with my parents, as well as a lot of alcohol. Alan didn't like to dance, so whenever I was around Nicola would drag me up to dance with her. And as I was embarrassed and shy, she used to keep telling me to come closer. By that time, I had learned to prepare a mean cocktail (even though I was supposedly too young to drink myself) and once, when I prepared one for her, she commented, "Oh, that's strong. Are you trying to get me drunk?"
On one occasion, she was getting quite touchy with her husband. And for some reason it annoyed him. He looked at me and said, "Do you want to change places?" And when I asked why, he said, "She keeps pestering me." That got me even more embarrassed than usual, as my parents were sitting there too, and I thought maybe he had also noticed me staring at his wife. Looking back now, I like to think that there was maybe a little bit of a "cuckold" in there. Because there were other instances too, one in particular where he joked about his wife loving to give blowjobs while staring directly at me.
Of the other instances when Nicky flirted with me, the ones that have stuck mostly in my mind are as follows:
There was a film about cheating spouses, with one of the men infatuated with one of his wife's friends, because of her shapely bum. One day he saw her from behind on the street and walked up to say hello. She asked, with a flirty smile, how he had recognised her from behind. This film had just been shown on the TV a few nights earlier. And I bumped into Nicky in the same way. And she asked me the same question, with the same flirty look. Luckily (or maybe not) her son was with her and I could make up the excuse that it was him I noticed!
On another occasion, there was a problem with our water being turned off. She suggested going home and filling up a few bottles to see us through. And said I should go with her to help her. So I was alone with her in their house. She invited me into the shed where the empty whisky bottles were. It was quite tight and cramped and we had to stand fairly close. We bumped into each other, with me finally coming into contact with that gorgeous ass. But that was as far as it went. I was too shy. Maybe she got scared too. After all, I was the son of her best friend. And I was still underage.
Then there was a weekend trip away. My brother was at school in another town at the time. We went down to see him for the weekend and Alan, Nicky and their son tagged along. We all piled into my parents' car, with my dad driving, Alan next to him in front, and my mum, Nicky and I in the back. I was in the middle and her son was in her lap (he must have been around 5 or 6 at the time). He was a restless child. And he moved around a lot. At one time, he actually caused her skirt to ride right up, that I got to see all the way up her legs, to the tops of her tights. I was thinking more masturbation material for me, when she came up with something else.
The men were part of a social club and had meetings a couple of times a month. I was at university by this time but I was home for a mid-term break the following week. There was a meeting scheduled for that week. And Nicky said, "They'll be at their meeting and I'll be stuck at home. You know I love to dance. Take me to a club that night." I was perplexed. I didn't know what to say. It didn't help that she actually placed her hand on my leg and rubbed up and down a few times as she was saying this. But my mum was sitting right next to me. And I knew there was no way I could do that without my mum tagging along. And, of course, there was no way I wanted to go to a club with my mum! I ended up asking who was going to look after her son. And her husband chimed in, saying "Why would he want to go to a club with someone your age?" I was half expecting another big fight then. Thankfully, it didn't happen. And then I decided it was a good time to feign sleep, to avoid more embarrassment. I actually desperately wanted to go with her, of course. Or be alone with her somewhere. But it just wasn't happening.
Then the chance presented itself, out of the blue. And it was like I'd won the lottery.
It was the following summer. I was now 20. And I was going to spend most of my holiday at my grandparents' house by the coast in Spain. Mu uncle also lived there (we're part Spanish).
(Another bit of background here. I had just sen a Tinto Brass film about a cheating wife, prior to going on this holiday. And the woman reminded me of Nicky, both with her facial features and her flirty demeanour, as well as her sexy bum. So this was also very fresh in my mind when going on the holiday.)
My uncle was actually getting engaged and so there was going to be a party. As luck would have it, Alan and Nicola were also in Spain on their summer holiday. They were going to go on to Tenerife from there.
We had the party. And when they arrived, it had been raining and she had got a little mud on her legs. She wanted to wash her legs and went into the shower. But she left the door ajar. And as I was walking past, I saw her with her skirt raised and washing her legs. Not naked or anything like that. Just her skirt raised and her beautiful legs on full view. She saw me and winked at me. And I continued past the bathroom.
That night, Alan came up to me and said, "we're going to a nice resort in Tenerife. Why don't you tag along? It'll be fun. It's got it's own nightclub and pool." I would probably have been too shy to accept, thinking I would have to ask my dad to pay for it and not wanting to upset my grandparents, who I was supposed to be spending time with.
But luckily, my grandmother overheard us and suggested that they could pay for it. So, that was that.
When we arrived at the hotel, we found that they had a family room, with mine being a single, on another floor and at the other end of the hotel. We were going to be there 4 nights.
On the first night, with Alan again having had quite a lot to drink, Nicky said, "He can babysit and you take me to this club. You know I love dancing. No excuses this time." I was getting little more confident by now. I had a girlfriend at university and was no longer a virgin. Plus my mum wasn't around to throw a spanner in the works.
And so off we went. We had a couple of drinks and a few dances and then the slow songs came on. So we continued to dance. Up until then, whenever we had danced, it was the traditional one arm round the waist and the other holding a hand. This time I took the lead and put both my hands around her waist. Well, everyone else there was dancing like that! And I got up close from the start. She said, "That's better. Not so shy anymore!" And we got quite close, with the fronts of our thighs actually touching each other, but I had to try to control myself to make sure my growing erection wouldn't bump into her. I knew the moment it did, it would become a full erection and it could very well ruin everything. I was still scared.
We had a nice time. Then walked back to the main building. She got off the elevator first. We were alone, and as she got off, she thanked me for a lovely night and gave me a quick peck on the lips.
