According to family legend, my grandfather made serious money in his thirties. He decided to retire from the big city and move to a seaside town with a growing reputation as a surfing paradise. The intention was that my father, who was eleven at the time, would have the ultimate childhood. He bought a big house overlooking the bay and invested money in holiday homes, bars, and restaurants.

Grandad quickly became a mover and shaker in the town, and as a side-effect, my father became a catch. My mother, who was the queen of the year above him, took his virginity on his sixteenth birthday and six months later, fell pregnant with me. Grandad was not happy, but supported them in getting married. He also helped my father in carving out a career for himself.

The fact that he didn't get higher qualifications wasn't a problem, as Dad was an IT wizard. Initially, he helped local businesses with computers and broadband. As he got more experienced, Grandad helped him with his contacts in the city, getting decent contracts and staying cheap. Dad stayed in the spare rooms of many of his old friends during the week.

Initially, Dad left on Monday on the first train, returning on Friday evening. Over time, this time got shorter and shorter, sometimes only twenty-four hours at home.. Eventually, my parents gave up trying to patch up their relationship. They got divorced around the time I was nine. We were living in a big house overlooking the bay close to Grandad. As part of the divorce, Dad signed over his half of the house to me in trust with Grandad.

Mum remarried almost immediately to a guy who had spent much time at the house in the last few years. He thought he was marrying a pot of gold, but it turned out differently. To stay living there, he had to be good to me; otherwise, the house would be sold, and I would live with my grandparents with a nice trust fund. I ended up with two step-sisters, much younger than me. It was all good.

Over the next ten years, I saw my father around twenty times a year. Most of this was related to the sports team we both supported. He got hold of season tickets at weekends, and when there were home games, I would make the trip up on the train. He started living in a small one-bedroom flat, but after a couple of years, he moved into the penthouse apartment where he and Sophie now live.

After the move, I became aware that he had girlfriends. They were rarely there in person, but the toiletries in the bathroom and the flimsy underwear in the washing basket were a giveaway. Ok, I was a bit of a pervert when I was younger, but what horny fourteen-year-old isn't going to check out the silk knickers or bra of their potential stepmom. I thought I was pretty standard.

The big thing with the girlfriend was the summer holiday. Dad explained that one of his clients could not pay their bill for some software his firm wrote. So he got two weeks a year in a luxury villa with its private pool instead. It was set in a complex with bars, restaurants, and bigger pools. I would spend my time playing in the big pool with kids who came every year and sneaking into the villa to catch Dad's girlfriend topless.

Initially, there was Debbie, blond and big-chested. Then we had Helga, the ice maiden who walked around in a thong, white-haired and flat-chested. After that came Alice, a brunette who shouted at me when I saw her tits. Each year was the same. Dad got a new girlfriend just before Christmas, occasional sights of her in April and May and then the holiday in July. Shortly after that, they split up.

I always figured it was me. The only similarity of the girlfriends was that they were twenty-seven. Dad explained that she would understand his lifestyle and be ready to live together at that age. However, each year, I got a little closer in age to his girlfriend as the gap to him got bigger. Finally, when Sophie arrived, and he got married, she was closer in age to me than him.

I would say that Sophie was the best. Unfortunately, she had lost both her parents, and she was an only child. As a result, she was keen to know me from the start. We got on well. She even helped me with problems I had with girls. She also guided me on fashion. She was more like a big sister than a prospective stepmom. We hugged a lot, and she persuaded Dad to keep my bedroom for me, with clothes I just wore in the city.

I should also point out that Sophie was easily the hottest girlfriend he had. She worked out quite a bit. She did Pilates and Yoga, so she was very flexible and graceful. Her breasts were neither too big nor too small, and her nipples seemed permanently erect. She also had the habit of wearing slightly too few clothes. On the summer holiday, she went topless the whole time and didn't cover up when I came back.

She also didn't break up with Dad like every other girlfriend in August. She was still there the following Christmas. She even came to Grandad's for Christmas dinner. My grandparents loved her too, and we were all happy when Dad explained they would be getting married in the following May. Dad swapped his two weeks in the summer for one week in May. I was the best man, and it would be just seven of us at the ceremony.

It was my last year in school, so I was studying hard. As a result, I only went for the weekend with my grandparents. Sophie's two best friends, Zena and Claire, were there all week. They were the same age as her. It was amazing the day before for a nineteen-year-old boy. I was sunbathing with three hotties, all topless. Even Grandma was in a bikini, and life was good.

On the day itself, the ceremony and dinner afterwards were grand. We all drank too much champagne, and after it got dark, Zena, Claire, and I got an Uber back to the villa, leaving the two married couples in town. We were all drunk when we got back, we moved on to shots, and all of a sudden, the hot tub was fired up. The two girls stripped off and goaded me into getting in the tub naked with them,

I think this is the point where I mention that I have a big dick. You may wonder what the problem is. I wish I had a big one too. Now I agree with you, but at that point in my life, a big dick was a problem. My young girlfriends were scared shitless. How will that thing fit in my mouth, in my pussy? I had managed to lose my virginity with a visitor last summer, but to me, it seemed more trouble than benefit.

Zena and Claire seemed very impressed as I stepped into the hot tub, naked and erect. I was drunk enough not to hide it or feel self-conscious. They started calling me Donkey Boy and have done so ever since. After giggling and joking around, Claire asked if Sophie had seen it. When I mentioned, of course not, they decided they needed to take pictures for her.

So Zena got out, dried off and went to get her phone. Claire and I stood up, she grabbed it with both hands, the head of my cock still visible. Zena took pictures and another of Claire failing to get her fingers around it. She sent them to Sophie right then and there. I figured that some porn fantasy was now going to happen, but unfortunately not. After ten minutes of piss-taking, the girls got out, explained they were lesbians and went to bed.

Since our bedrooms shared a wall, I spent most of the night beating off whilst sounds of orgasms came from the other side. They were very noisy and very horny. It was very late when they finally stopped, and I could too. I wanked myself off so many times I was sore in the morning. And hung over. It was only a few hours before my grandparents collected me for the airport.

I thought about the near miss many times in the following weeks as a distraction from studying for my exams. We had also agreed that I would not visit Dad until they were over. Eventually, they were over, and I could spend the rest of the summer with the severe task of surfing every day if I could. And I was hoping to find a girlfriend who could cope with my size so I could get some decent sex.

I was surprised when, just after my exams were completed, Sophie rang me. She had never rung me before, usually joining in calls from Dad. Could I do her a big favour? A friend of hers, Rachel, and two other couples were renting one of Grandad's cottages for a long weekend. Could I take care of them for her? Show them the best waves and sort out the wetsuit and board rental. Take them to the liveliest nightlife.

I was thrilled to do something for Sophie. She seemed to do loads for me. Leading Rachel around was not a difficult job at all. She was a hot girl in her mid-twenties, probably an eight and a half. They sorted themselves out with a takeaway on Friday night and we met up on Saturday at nine. The five of them got into their car and I directed them to the next bay. It was a long way by car, but only a short ride on my bike.

When they got there, I had already changed into my wetsuit. I sorted them out with suits and boards at the hire shop. Since that too was owned by grandad, I got a big discount. I then gave them some informal lessons. I had done this before with visitors. You had to show them how their body needed to be and move on the board. Plenty of opportunity for a little extra touching, especially on three hot girls in small bikinis.

Their boyfriends seemed fine with it, given that I gave them the top tip. Go commando under a wetsuit. It clings and shows off your body in the best light. Don't hide it with trunks. After all, women wear yoga pants for exactly the same reason. A lifetime of surfing had given me an almost perfect ass, strong legs, and a flat stomach. A wetsuit showed them and the shape of my cock off to perfection.

I directed them to the right restaurant on Saturday night and agreed to meet at ten to take them to suitable bars. However, only Rachel wanted to go drinking, and dancing. She ground herself against my now hard cock. Soon I was walking her back to the rental. She had her arms around me and we made out a couple of times. I knew where all the hidden back alleys were, so we kept private.

One thing led to another, and I woke up in her bed the following day. She was delighted with the size of my cock. She enjoyed it a lot that night and most of the next day. I was worn out when they left for the city on Sunday afternoon. She told me she would provide Sophie with a full report, and if she ever went surfing again, she would look me up. I felt on top of the world for the next month.

About two weeks later, Dad phoned and told me that he and Sophie were visiting his parents that weekend and asked if I would come for dinner on Saturday night. He had a proposition for me. I had the suitable grades to attend the college I had initially chosen, but he had an alternative for me. He lectured at the college close to his home, specialising in IT. It had a high-profile IT course.

They would offer me a place after chatting to the board and with my results. I could live for the next three years with him and Sophie, free of charge. He would pay me a lot of pocket money rather than having to work for my beer money. He had recently changed his work, moving into home electronic systems. It meant he was away a lot midweek with clients and developers. Keeping Sophie company whilst he was away would be my job.

It seemed a total no-brainer for me. Working by staying in and studying or watching TV with the hottest woman I knew seemed like the perfect chore. Dad was also saving money because the college course was free, swapped by him doing an extra few days of lecturing. It was all agreed I would surf for the rest of the summer and join them in the city to live in September.