My wife and I (M36/F35) have been married for a very long time (High School Sweethearts). I realized a while back that I had the fantasy to watch her having sex with other men. I wanted to watch her face as other men took her, and I enjoyed the thought of her making other men cum. We have talked about this in around about ways for five years now. I wasn't until my recent trip away that we got serious about it, and she started to read online and research how this fantasy and lifestyle was more present and common than she thought. She started to understand and accept what I meant, realizing that it wasn't merely to push her away onto another guy so that I could easily "cheat" or divorce her for being unfaithful. We Joined Reddit and she began posting random comments or photos and was quickly taken back by the number of responses she got. I asked her to sext with a couple guys and she was hesitant as she still felt wrong exposing herself to other men and their request. She ended up (over a couple weeks) getting 3 men to cum to her and she realized quickly she loved the confidence it gave her. I did my absolute in supporting her (Mind you I am still away) and showed that I was not jealous or upset, but rather turned on and excited for her. She admitted that with my absence, she was really horny and thought she would be willing to experiment with another female, and we set off on Reddit once more to try and find a candidate. Through some time and back and forth, it seemed we could only get attention from couples (age I guess? or just the nature of Reddit?) She decided she wasn't ready for contact with men, and we sort of let it settle out. after some time of not really finding any woman for her to explore a different sexuality with, and a lot more conversations of our thoughts and feelings, we decided to look for a man for her to have sex with. It took a lot of honesty, understanding, research on how to make it work, and trust but we found two different guys that understood our goals and respected the nature of our requests and we started to plan and set up a meeting. (Luckily it was 2) The first guy was going to meet but ended up ghosting her the day of, which really upset my wife, so by the next weekend my wife had set up with guy #2... as luck would have it, she ended up not being able to meet as her monthly body obligations decided to show up early.. Guy#2 understood, and it would be another 2 weeks before the chance to meet would happen. Fast forward to past Saturday night and she booked the hotel, had a new outfit that made her feel pretty and a little slutty and met with this guy. This is huge because she did all this on her own (with long distance support from me). She suppressed all her fear and anxiety and made this ginormous leap forward alone. I was so proud of her. (We decided together after the pros and cons debate, that we would be okay with going this route). She video chats me the whole event, from meet up with the guy, the walk down the hotel hallway all the way to the guy cleaning his cum with a rag off of her ass. (I decided to hold off on any of my own personal gratification until she was alone and could watch me do it for her as we replayed what happened). When the guy left, we started talking and going over our emotions and making sure that there were no instant regrets and general remarks of where our heads were. Then she admitted to me that she wasn't able to get off.... for various reasons she didn't cum and felt like this whole night was a waste of time and effort ... I felt like shit ... I was so upset for her because we are in this together and here, she is doing everything alone and at the end of it, I was the only one who enjoyed it... I quickly told her to not leave the hotel and instead we both got back on Reddit and started reviewing previous chats of people we liked. At the same time, I got back on a community and started looking at newer posts. We quickly found a guy we both liked, and she shot him over a message with her boobs flashed and got a response back. After some quick back and forth she agreed to meet this new guy (previously unvetted) at a bar and see how they felt. I stayed on the phone with her through everything up until I heard her say "Hi" and she let me go so she could go into the bar and chat. Roughly 45 minutes later she calls me (she was texting me "check ins" to let me know she was okay) and let me know that this man was very laid back, seemed really easy to talk to and had an immediate connection with. She wanted to fuck him. They decided that it would be more comfortable for them to go back to his place and not the hotel. I talked with her on her drive to check out the hotel and as she got back to his house. He was fully aware that she was married and that her very first attempt at being a hotwife and getting into a swinger lifestyle had gone less than desired, but she failed to mention that I wanted to see it all via video chat. After letting him know, he did not like the idea of that kind of exposure (I understood, he had no idea or understanding for the most part what it was about for us, more than my wife had full permission to get laid and it was his job to redeem it for men everywhere). We agreed that as long as she sent me pictures of her working on him from his point of view that I would be okay. An hr. and 20 minutes later with 2 videos and 5 pictures sent, I got an "all done" "LOL" text... I was immediately relieved because I knew she was happy, and it meant that she had to have had an orgasm... She called me on her drive home, and we went over everything. She had a great time and was so relieved that it went as well and smoothly as it did. She was relaxed and into it and ended up having two orgasms with him. We talked a lot more still and went over a lot of the things we have learned. She enjoyed the easier meet and greeted at the bar, as it didn't take weeks of planning, but still believes it's better to contact guys via internet and see there cock first (she is picky). While I am in complete understanding and acceptance of how and why it went the way it went, I have realized that I am now a little nervous on how easy it was for her to go get rebound sex (but I can honestly say I trust she will not as she has proven many times over that we are a team). but still... also I did not like the fact that I never got to see the guy she had sex with more than just his cock in her mouth and vagina. (But the smile and enjoyment she had on her face was well worth it) I have assured her that I am blown away and flat out amazed at how strong and beautiful she is. My thoughts of this fantasy were confirmed as being able to sit back and see her reactions and face was quite possibly the best thing I have seen ever. We have been very honest and open as we have discussed this, we know nothing is going to go perfect starting out. She has realized that this is something she can really enjoy and knows it was never a weird motive setup. This weekend my wife went from a woman I married, that honestly thought admitting out loud that someone was attractive was wrong, to a woman that booked a hotel, was left unsatisfied and met a stranger at a bar and went to his place to fuck him. (I know that scenario is like every 23-year-old single female, so it's not groundbreaking... but for my wife and us... 6 months ago was unimaginable). We are still undecided and pondering the idea of going full couple swap or her becoming a unicorn. She has expressed attraction to very certain woman with very certain personalities so finding the right couple may become a unicorn search in itself. She is very jealous of me flirting or the idea of me showing any attention to other woman and to be honest right now, I don't know that I could handle trying to please a woman other than my wife, when my whole goal is to just hold on to her and watch as she has great orgasms. I don't know if this completely fits the swinger mantra, but I do feel as though she has earned her anklet, and I am searching now to find something special / meaningful to buy her to commemorate and show how proud and truly in love with her I am! Thanks for Reading, fill free to message me thoughts, concerns, tips or advice.