I have responded to this question earlier, but didn't provide many details. I thought it would be good to share the details of an incident that became a friendship that shaped my enjoyment of spanking.
Simply put, my parents were quite busy socialising, and they asked a young man called Andrew if he would be happy to look after me when needed. He agreed, and so he became a playmate for want of a phrase, and we would go out walking and playing about in the countryside, and because I knew Andrew well, it could be fun, especially when we took our air rifles trying to kill pigeons or sparrows.
One time, the first time, I was cheeky and didn't listen to Andrew, as my parents had told me to. Andrew got a little angry and threatened to spank me. I continued, and he sat down on a log and told me he was going to spank me and to bend over his lap. I did as told, and he spanked me 6 times using his hand. Once he was finished, I got up and told him it didn't hurt because my dad would spank me without shorts and underwear. Andrew asked me if I wanted him to spank me, and I said yes, but he would have to do it like my dad if he was going to do it. He told me okay and I slipped my shorts down and bent over his knee and he pulled my briefs down and spanked my bare arse 6 times properly.
I so enjoyed it that I decided I would create an incident the next time he looked after me, which I did.
Doesn't matter what the incident was, but Andrew decided I should be spanked, and this time I had to remove my shorts and briefs and then bend over his lap. I didn't have a proper mature willy then, but he noticed I had an erection, and this was the first time he touched me, and I sooooo enjoyed it. Spanking became part of our time together, and I would always be naked to receive them. Andrew eventually got to masturbate me when I started to produce semen, and that changed our dynamic for good.
True story and a lovely personal memory.