While I was looking for some photos of spanking on the internet I came across a web site where people who wanted to be spanked could meet people who liked to spank people. The site was free to join and I had always wondered how much different it would feel to have someone spank me as an adult instead of spank myself, as I had done from time to time since I got spanked as a teenager so I thought I’ve got nothing to loose so I joined. I looked at some of the posts and found there was a bloke about 20 miles from me willing to spank naughty boys and a few people seemed to have commented he had spanked them and respected there limits so I sent him a message, I told him I hadn’t been spanked before but I had spanked myself a few times and would like to try being spanked. He replied to me and we exchanged a few emails to discuss what we both might want from a meeting if we did meet, I told him I was shy and he said that although he preferred the person he is spanking to be naked it was up to me if I felt I wanted to be or not and he would respect my limits but he would like me to at least take down my trousers so he could spank me in my underwear. He asked me to phone him and we discussed my limits again and agreed that I would at least try to take down my jeans so we arranged a time and date for me to meet him. I got his road and rang him as we had arranged and he met me on his drive and showed me to what he called his punishment room. His punishment room was basically a conservatory with ordinary single glazed windows at the side of his house and only a few feet from the road so although once we went in he shut the curtains so no one could see in I’m sure his neighbour and anyone walking past would hear what was going on. We sat down and talked over what we both expected again and I told him I would like to start being fully clothed but I would let him spank me in my boxer shorts if I felt I could, he said to feel a proper spanking I should at least be in my boxers but really a proper spanking should be on the bare bum but that was up to me and we would only do what I was comfortable with. I then said that I would like to try having my bare bum spanked but didn’t think I would be confident enough to with a total stranger, he said “we’ll see how you get on but its up to you” then he told me to get over his knee and started to spank me on my jeans. After a little while he asked me to take my jeans down and get back over his knee, I undid them and pulled them down to just below my bum got back over his knee and he spanked me on my boxers. Then once he had spanked me some more he asked me how I was feeling and if I wanted to continue, I said I would like to be spanked on my boxers some more but still wasn’t sure about anything else, he said I should take off my jeans and tee shirt I thought what the hell its no different to being at the swimming pool so I stripped off to just my boxers and got back over his knee. After he had given me a good spanking like this he asked if I wanted to be spanked properly on my bare bum, I said “I kind of do but I just can’t bring myself to take my boxers off or even down in front of a stranger” so he said if I wanted he could take them down then I could feel a proper spanking but didn’t have to take them down. I don’t know why but that seemed like a good idea as I really did want to have my bare bum spanked and this way I didn’t have to take them down so I asked him if he would spank me some more with my boxers still on but then to pull them down a little bit and spank me. He gave me a few more spanks then I felt him take hold of the waist band of my boxers and he waited a few seconds so I could tell him to stop but I didn’t say anything and I could feel him pull them down but instead of just pulling them down enough to just expose my bum he pulled them down so far that they feel to the floor around my ankles an spanked me on my bare bum. Next he told me to stand up and said I should try the strap now that I’m naked and go bend over the desk where he did use the strap on my bare bum. When he had finished we sat there with me still naked and he asked if I would come back again as I should be alright with having my bare bum spanked now, I said I would like to meet him again but probably not for a bit but if it was alright with him I would still like him to take down my boxers which he agreed to. I went to see him several times over the next couple of years and each time I got a bit more confident and tried new things, the next time I saw him I was so turned on I touched my cock without thinking about it and he said he would love to watch me wank as he spanked me so I did, then another time he played with my bum and asked if I wanted to try having a butt plug in my bum so I tried that and eventually I said I would like to try anal sex so he shagged my arse. Every time after the first I have ended up wanking off while he uses the strap on me till I cum.