After running my business for 15 years I was finally at a place where I could find someone to take over many of my day to day responsibilities. This would free up time for me to work on my personal life. I had long neglected putting much effort into looking for a life partner and I had become lonely  I decided that what I wanted was to find my partner as well as live out my fantasies. I had fantasies of sharing my partner with other men. It grew from years of porn, prbably started with stories in penthouse letters and the idea has always turned me on, but in order for this to be enjoyable, I needed to have a relationsip with my partner, it was about more than just sex and te lifstyle was something I wanted to share with my partner. I posted an ad on craigslist. Mandy responded. She said she was intrigued by my post.  Mandy did not fit the image of the person I expected to respond to my ad. I thought I would only get responses from a woman that was slutty, promiscuous, experienced n the lufestyle or maybe a woman looking for a sugar daddy.  Mandy was a sweet, shy, innocent school teacher with an open mind and a bit of a kinky It took a couple of months before we were able to have our first date. We spent a couple of months emailing and texting. Sharing our experiences. I shared details of my perverted but unfulfilled cuckold fantasies. We met for drinks at a nice bar. She had wine, I had a couple of Arnold palmers. We had a great time, we had chemistry and a definite mutual attraction.  Our second date I booked a room at a nice hotel on the beach. We had a nice romantic dinner and talked about next steps. I created a profile in adult friend finder and we started looking for men.  This proved more difficult than expected. Lots of fakes and flakes out there.  We decided to visit a swingers club. It was fun. We just watched the first night. It was exciting seeing the sexy people and meeting new people.  Curtis We decided to redouble our efforts and look on Craigslist. We found Curtis there. Curtis was a gentleman. He was patient with us. We met him for a cocktail. I saw Mandy kiss another man for the first time that night. We met again for a dinner. The sexual tension was off the charts. It was hot seeing them interact while sitting in the booth with the three of us. After that we scheduled a play date. I booked a night at a nice hotel. It was on Mandy’s birthday. Mandy and I had a steak dinner and then met Curtis in the hotel bar. We took him up to the hotel room where I watched Mandy have sex with Curtis. It lasted two hours and was one of the most exciting experiences of my life.  She was worried about how I would react when my fantasy became real but was reassured when she saw how much I enjoyed it. After Curtis left we had sex but I was so excited that I didn’t last more than two minutes, lol.  Surprisingly, Mandy wasn’t too interested in seeing him again. She told me that Curtis was in the military and would be repositioned in a few months. Mandy preferred someone she could see and play with regularly. This was something I hadn’t thought about. I thought I would just watch Mandy fuck a random guy once in a while, she had other plans. I had to adjust.  We started looking for a new guy. Disappointed with the fakes and flakes, we decided to attend a couple of private swingers parties. They were fun and whether we found a guy to play with or not, we had a good time. We didn’t have much luck in finder ng a local guy to play  with on a local basis until we met Jay.  He found us on Craigslist. He had no experience in the lifestyle, but The three of us learned about the life restyle together. We met and played fairly often. Mandy liked him. We would rent hotel rooms to meet and play. Sometimes I would sleep in the other bed and wake up to the sounds of them fucking.  At times, I would feel insecure and try to find another guy for Mandy. In reality, I should have just supported her and what made her happy. I think he ended up looking for something different than what we all wanted.  After Jay, we went to going to a couple of swingers parties and looking for guys. We found an Indian Dr that was younger. Mandy lived his accent and thought he was sexy. We played with him a few time over a few months and had fun with him but it ran its course.  Then we met the married guy. Mandy was against being the other woman but this guy was different. They texted quite a bit and seemed to have a good connection. She was willing to overlook that he was unhappily married. We talked about a new dynamic where Mandy would see this guy alone. I would get them a hotel room to play solo. It was both scary and exciting to me and something she wanted to experience. But when Mandy shared her text conversations with him, I reacted poorly to say the least. I felt on the outside. As if she didn’t share the experience with me. In reality she was honest with me and I regret how I reacted.  I feel that she resented me after that and she was right to do so. It was a good opportunity for us to experience new things. From there, we started working in our own connection. We didn’t look for a new guy. We built our relationship and I proposed to Mandy. Thankfully she accepted and she wanted the same thing.  We still looked for new men to meet. But that part of our life waned over time.  A couple of years later, Mandy was out of town and I texted her to ask how she felt about getting back into the lifestyle. She responded by telling me she missed playing and would like to play with other men again, but she had a new request, she wanted to play solo. She wanted to be able to go on dates. Play alone.  We started talking about it. Role paying sending sexy scenarios about her having a boyfriend.  We wrote up a new profile on our swingers website and in adult friend under. In it she says she wants to find a man for romantic dates. If all goes well, it might even become a life long affair.  It was a bit scary to me but also exciting. We would lie n bed sharing scenarios while we masterbated together. The more we talked about it the more I found myself encouraged ng her to take thinks further. This it what Mandy seemed so want all along. I was completely supportive and finally ready for this as well.  We found a guy, D, who seemed to be a good fit.  D had experience in the lifestyle and he was looking for a long term relationship with a hotwife.  Mandy met him for drinks new and they had a great time me. The only issue was that he couldn’t see Mandy as much as she wanted. He was available for one weekend a month. Mandy wanted more than that.  It was too me to start looking again but that’s when my health issues started. I had a stroke followed by heart bypass surgery. The I got diagnosed with prostate cancer.  I was in Lupron, an anti testosterone drug for 6 months. It took away my libido , gave me hot flashes and made me emotional. It also shrank my cock and balls. It was over a year before the effects finally wore off. The only permanent side effect is that my cock and balls are smaller.  I regret not having fulfilled mine and Mandy’s fantasies. I feel I want her to date romantically, spend nights and weekends with another man, or just casually play with other men. I regret that I haven’t been more supportive to make these things happen. We are getting older now. I’m 61. I feel like we are running out of time.  I want to write a lengthy biographical and erotic story to share with Mandy