A couple of years ago I really began researching ethical non-monogamy, poly, hotwifing and cheating wives a lot. I mean all of my porn searches boiled down to those categories for some reason. About then was when I began to recall in detail my own experiences witnessing my mom and dad do the swinging 70's wife swapping stuff. Which lead to long term lovers for my mom. Probably I was getting assistance from my subconscious, looking for answers for me to my celibacy, to get the ball rolling so to speak. Been a long rut. I mostly did not remember all of those parental poly years until I got here and read Des31's entire story and many more. I recollected a few of my parents sex parties over the years but the recent influx of those memories have caused me to journal any small detail into 39+ pages.
Before long I had hired a talk therapist to help me sort out these recovered memories and; "what could be the one thing that caused my arrested developement regarding sex and only trusting my right hand instead of actual fucking?" Turns out trust and patience are my Rubicons. Two things, not one. Over time I tended to hurry the seduction of the women I was attracted to sexually, like I thought I saw my married parents doing with their partners. I would just hear or see my parents fucking their partners, and did not see at all how the agreed upon sex had been arranged. I did not have good examples of how to take things slowly and tended to get shot down using the fast track method to sex, like my parents seemed to do. While drunk I must have exhibited false machismo seduction and scored here and there back then because of it. Just prior to retiring from alcohol and occaisional party favors in 2002, I had lost my mojo seemingly for ever. Most of my sex partners were set-ups via friends. Maybe I never had any game and now I have to learn that part. So sexual patience is one challenge for me as I navigate year 23 of my sobriety. I can't just jump into bed with a woman unless I hire an escort and at this point I will be doing this very soon. My talk therapist and I feel that if I can get the celibacy monkey off of my back then I can perhaps begin to slowly move forward into some great long term sex partnership before I die. Thankfully I do not need chemicals to get hard. So a week long trip to Vegas or Amsterdam is probably my answer. I hate flying as I am a big dude and don't fit well in those small seats comfortably so maybe not. Thinking prostitution is illegal in my home state of Wisconsin I may need to see what laws Illinois has as I am near to that border. Or find a very understanding woman who can coach me for a while and release me back into the wild.
Trust is another big deal for me, tending in my past to lean away from a potential girlfriend when I felt the intimacy and closeness or, to be attracted to women who weren't attracted to me and get shot down. A confusing place to be. So focusing on me and my career choices, and basically missing out on having a wife and kids, am now early retired with an open calendar. Can only hunt, fish, workout and travel so much, to avoid the obvious emptiness at home where I find myself here most days or nights just jacking off again. A bit boring after 31 years of it but it is all that I have for right now.
I recently met a young family through a job that I volunteer at and I at first only got calls from the husband, but the wife began calling me to arrange helping them move into an apartment. Now she calls about helping her to find a used vehicle. She and their youngster were in a wreck, nobody got hurt. No insurance for their vehicle's unfortunate total loss and there was not another vehicle involved in the wreck, so she needs a car before long. The wife said she will pay me to drive her next week 130 miles round trip or one way, not sure yet on the distances to a vehicle she wants to look at. I have pretended to not be attracted to her since January. After the move-in day, we went swimming and she is around 30 looking very good in a swimsuit. Her husband left us at the pool to run errands so I was able to make a lot of eye contact and smiles from the pool as I gave swim lessons to their child, while his wife sat in the sun. Last week her husband asked her to call me for help with the car search and I without any reservation at all said yes to being her transportation. Secretly hoping that we may need a hotel room if the universe wants my fantasy to hotwife this beautiful woman to happen, Lol.
I already know to let her take the lead on this which goes against my alpha tendencies to move too quick and wreck it. I am also concerned about any of my fantasies setting me up for another failure and lost friendships. When I am talking to her and near to her we tend to lock eyes and smile to each other a lot, regardless if hubby is right there. I have stifled one wet swimsuit hug with her before I went home that night after our swim, because I got nervous. She stepped two paces toward me into our very close personal spaces wanting a hug during my goodbye, as her husband turned and walked into the apartment away from us, I only smiled at her. Should have hugged her. Maybe that was a dual lesson on just taking things very slow with a hint of a reminder of an old habit of mine of turning and running from intimacy. But instead I may be coaching myself to no longer avoid intimacy and to just hug her next time. If hubby complains then I did not turn her away, he did. Then it is on him and I was not cock blocking myself through sabotoge and fear. I do not want to fuck this up in either direction. Would like to remain friends with these two really awesome people and would like to find out discretely, perhaps alone in my car with her, if they have an open marriage like my parents did for 22 years. I know husbands and wives talk candidly to one another and would like to just flat out tell her that I like her more than friends. But if she is not interested in friends with benefits with my open calendar and she shoots me down, then to preserve the friendship I would not want her husband to know about our conversation.
I can only hope she brings it up, and it feels like she may bring it up, otherwise it may be a very long uncomfortably quiet car ride next week if I bring it up and she embarrassingly clarifies any mixed signals I received through my filters. OR, the OHW 'pull over and fuck me now' scenario happens. If the latter happens, I will share it with you all here soon after, from my phone, while frantically spell correcting with these sasquatch fingers on a virtual tiny keyboard.

Any tips?