I am Ray, 52 keep myself quite fit, medium build, got most of my hair, but it is now all grey. My wife, Claire is 49, short dark brown hair and green eyes, huge boobs, but who keeps herself slim going to the gym and takes care with her appearance after having 3 children who have only recently moved away. I hit a mid-life crisis coinciding with coming in to a little money that I shamefully kept secret from Claire. Even worse as our sex life dropped to almost birthdays and holy days I started visiting massage parlours and this developed to escorts including some of my kinky fantasies. Nothing I was proud of but I tried to convince myself this was better than an affair. Without going in to too much detail Claire found out that I was paying for sex but didn’t know the exact details. I didn’t want her to divorce me, mainly because of our family but also because I genuinely love her. Claire demanded to know all the details. I foolishly thought that I would select the kinky stuff and tell her I did that because I knew she wouldn’t want to do it with me and I was embarrassed to ask. I felt this might go down better than saying I wanted to have sex with younger or prettier females. She demanded I show her so I pulled up the website for the Mistress I went to and she read that. Obviously there were a lot of services available so I told Claire I had paid to be punished like a schoolboy which was true. She knew it hadnt stopped there and asked if I had screwed the Mistress. I said no but we had played with toys which was partly true. Claire was firing questions by the hundreds and to keep her away from the pure sex acts I thought would make her very angry I admitted the Mistress had used a strap-on penis on me. After this Claire refused to talk to me for a full week. She said she was more angry than hurt as could excuse my fetishes but the fact that I had wasted so much cash whilst she was so careful with money and done this behind her back. She said I would have one chance of making it up and she would decide what that was. Over three weeks later Claire called me and said she would forgive and forget but only if I followed her plan to cure me of my nasty little fetish. I agreed and then she pulled up a website of a man who offered corporal punishment to adults. He actually lived in Wiltshire about a 90 minute drive from us. I couldn’t understand Claire’s reasoning but also wasn’t aware then that she had already spoken to him. I was forced to call him and book an appointment for the next Saturday. I was also told to tell him I wanted six of the best and that I wanted a strap-on pushed in my bottom. She felt that if I had this done by a man I wouldnt want it again from my Mistress. This was the deal and I went along with it. On the Saturday I got ready to leave and then Claire surprisingly joined me I guessed she wanted to ensure I didn’t duck out. On arrival the man who introduced himself as Mr. H-J was quite tall and athletic but looked in his mid to late 60s. His house was quite small but it had large grounds and a few brick storage sheds and he lead us to one of them. We entered and it was a little dark with one small window at the end but what caught my eye was an old low back green leather chair in the middle of the room with three crook handle canes beside it. Mr. H-J closed the door and said to me “take all of your clothes off and hang them on the wall hooks then prepare yourself for six of the best”. Claire smiled at me and looked to the hooks as if to say “on you go”. I hesitated and then Mr. H-J barked at me “Do it now or go home. Do not waste my time”. I knew going home meant breaking Claires demands so stripped until I was naked. The air was actually cold and the floor cold on my feet. Mr. H-J picked up a cane and pointed to the chair. “Get right over”. I bent over the back with Claire in front of me. I felt the cold air on my buttocks and legs and the bending over was a strange position. Mr. H-J then started bending the cane and swished it a few practise times through the air and shouted “stick your bottom out further”. Claire smiled at me and for effect then pushed her hand inside her jeans and down to her pussy and said quietly to me “I am going to enjoy this”. However, she then moved to behind me looking at my bare bum. I could just about squint back and see Mr. H-J take a few steps back then staring at my bottom almost ran two steps forward. I saw the cane coming over his shoulder, heard the whistle through the air and then crack on my buttocks. The pain was horrific and twenty times more painful than with my Mistress. I shouted out and my arms came up but Mr. H-J screamed “stay where you are”. Then another run up and the second strike again took my breath away. My eyes were beginning to water as this was so painful. The third stroke landed on the same spot as one of the first two and was excruciatingly sore. I thought I can’t take any more of this but Mr. H-J stopped for a few minutes. Then said “prepare yourself for the last three”. Another run up and a huge crack, this one being low almost at the top of my legs. The fifth strike was on the fleshy part where my bum met my legs and was so sore my legs started to tremble. I had shouted out at each of the strokes after the second and now water was coming out of my eyes. I wasn;t blubbering but I could not help my eyes watering. “Last one” shouted H-J and then I could her the running steps. I just kept me head down and didn’t watch but heard the swish and then burning pain as the last one which I think was the hardest went across the other strokes. I was shaking with the pain. I never imagned it would be this painful when I was caned by the Mistress. Mr H-J said stay where you are. He came around to the front of me with Claire. He said in a quite voice “I thought being caned made your willy stiff ? Doesn’t appear to have happened this time”. Then her undid his trousers and pushed them and his underpants to his knees. He had a thick but soft cock dangling between his legs and started to stroke it. I watched as it began to grow longer and then he pulled back the thick foreskin to reveal a pink and gleaming head. It was now sticking out at right angles and then Claire walked over towards Mr H-J. I couldn’t believe when she held out her hand and held it. She gave it some tugs as it stiffened more and I thought she was going to wank him in front of me. However he pulled out a condom from his jacket pocket and gave it to her. Claire unrapped the condom pulled his foreskin right back as far as it would go and then proceeded to roll it on to Mr. H-Js cock which was now standing pointing straight up and fully erect. Watchng this I now also became erect even tho my caned bottom was still stinging like mad. Claire then held my hands and pushed them down in to the arms of the chair holding them firmly. Mr. H-J then moved behind me and soon I could feel cold cream being placed by his finger in my bum hole. More cold cream then a finger entered followed by another. I got a sense of what was coming. Claire look directly at me and then looked up over me at Mr. H-J. I could feel his hot hardness against my bum hole and then he just pushed slowly but straight in with one shove. I shouted out as it was so sudden and not a little bit at a time as with my Mistress. He was fully in with Claire holding my arms down. He then started to thrust in and out which was initially painful in my anal passage but also the banging of my caned bottom and stripes. The chair was creaking with the pounding from behind and Claire again whispered “I hope you are enjoying this you naughty little boy”. Mr. H-J was taking ages and I wanted him to hurry up as my caned buttocks and anal passage couldn’t take any more. Soon the thrusting became very frantic, there was one big push and I felt the hot cock in my back passage spasm and heard Mr H-J groan loudly. He then pulled out of me quite abruptly which was uncomfortable. Claire kept holding me and said “stay where you are”. I dreaded what was coming next and waited for a while, but bum and arse both stinging with pain. Then I heard the door open and quickly close again. Claire then whispered “Ray, get up, sort yourself out and get dressed. We’re done”. Mr. H-J had gone so I used some tissues ot clean up and then very gingerly put my clothes back on. Claire drove home as my bum was still smarting in the car seat. As we left the village Claire said “I enjoyed that more than I thought I would. If you want to spend money getting your bottom punished we can go back again, but only to Mr. H-J. Do you understand ?” I did but even now I don’t think I could take that pain ever again.