I have always found writing to be very therapeutic as it gives me an outlet to express my views and ease my stress. As a Libertarian living in 2020 I am constantly under stress. As the title implies I have had a fascination with the Male Chastity lifestyle for several years. It has always been a fetish to relinquish control of my genitals to a strong female partner. As someone in my mid 30s I just came out of a 15 year relationship that sadly ended in divorce. Our Sex life in the beginning was very vanilla and would occasionally venture into very light BDSM. My previous partner was never into the Domineering position in the bedroom. In 2016 I had mentioned to her about possibly giving Male Chastity a try but she was not respective to it at all even with my attempts at persuasion. I waited until early 2018 to bring it up again and after much discussion she relented and allowed us to give it a try. For about a year my orgasms were under her control. She would attempt to indulge my other fantasies including anal stimulation and light BDSM of bondage but nothing beyond that. Our Marriage had been suffering outside of this activity for some time and she started to develop some severe mental issues that had manifested some years prior due to some tragic events. In March of 2019 I put the Chastity cage away and ceased all activities related to it (As well as other lifestyle changes) and attempted to save our marriage. My attempts were in vein however and in September 2019 She asked me for a Divorced which I decided was the right thing to do as all my attempts to try and help her were going nowhere and she was no longer in love with me. ...... After a few months of loneliness and giving Bachelorhood a try (I had great support from Friends and Family during this time BTW) I decided to throw my hat back in the ring and dip my toe into the dating pool and see what was going on. I happened to come across the love of my life. I found a Beautiful Woman who is Sexy, Smart, Funny, Independent, and very much drama free. We have been together for five lovely months and I have had the most wonderful time of my life (COVID issues aside of course.) I have come to discover she is a very passionate woman in the bedroom and even at the last year of my Marriage my Sex life has gone from Zero to Eighty in a short amount of time. She is somewhat kinky but has absolutely no need or desire for sex toys as she views them a "cheating" since two people should be able to make each other feel good without them. Of course, the chastity bug has bitten me again and I have wanted to be locked again for some time. All of my previous cages are still stored away in my bedroom and waiting to lock away my Cock. I have mentioned my fetish the first time early in our relationship and she was a bit taken aback by it but she kind of joked that "what guy would willingly let a girl lock up his dick." I said nothing after that. Last weekend I brought up the topic again and asked if she would possibly be interested in being my Keyholder. She was a again taken aback but had no idea about the mechanics of a cock cage. So I asked if she would like to see me in one. She said sure and I had her take a seat in my Bedroom. I then pulled out three different cages; A knockoff Pink Holy Trainer, A Knockoff CB-6000 in clear red, and a Chinese Metal open cage (magic locker type.) Her eyes went wide when she saw them and and I used the key to take one of them apart. I showed her how it worked and asked if she would like me to put one on to demonstrate? She said "Uh.........sure." As I was putting my balls through the ring (using the metal cage) Her jaw dropped when I was finished and as a I was pulling my cock through the ring she asked "Doesn't that hurt?" I replied "Not at all." I then used cut pantyhose to pull my cock through the cage and crabbed the key with the magic locker and clicked it shut. I then put the key down and stood up so she could see. She then reached up and cupped my package. She asked "What happens if you get hard." "The cage won't let me get hard" I replied. I then described the Pro's and Cons to each cage in regards to stealth, hygene, comfort, and other factors. After talking about it for 20 minutes she said she needed some time to think about it. She said she had no idea about being a KH or what Male Chastity would entail. I told her that there is a very deep well when it comes to this arrangement and if there is a level 1 through 5 I would max out at a 2. One of her favorite movies is 50 shades of grey and I am not looking to be a Submissive in a Femdom dynamic. I'm more looking for a Woman to take control of my orgasms and decide when and if I get to Cum and in what fashion it will happen. After my dick had been in the cage for the 20 minutes she asked that I remove the device. I did as instructed and asked her what she thinked. She said she's not too keen on the idea as it looks painful and that she doesn't like something like that being attached o me without coming off easily. I told her I always keep an emergency key with me and I have worn one for three solid weeks without issue. She still wasn't sure but said she wasn't too comfortable with it. I left the conversation their and we went about our day. Yesterday we were talking in bed and I drifted the conversation in the chastity direction again. "You are still on that aren't you? Why do you want your dick locked up?" She said. "I guess its just the thrill of having someone in control of my sexuality, I especially want it from someone whom I trust and would share the experience with me." I said. "Hmmm, I don't know, I'll need to really think about it, My Sister is an expert on all things sex and if she hasn't heard of it I'll be shocked. Let me ask her if that's of." She said. "I have no issue with that, there are a couple of websites that offer basic guides on what male chastity is about and some advice for new keyholders, would it be alright if I send it to you? "Yes, that will be fine." .... So that's where I am at, I possibly may be getting a new Key Holder. If she ultimately decides against it I will drop it completely as her love is way more important than a sexual fetish. But if she agrees I will ease her in slowly. I'm not looking to be Cucked or Fucked in the Ass via a Strapon by this woman but rather share a sexual desire with her and see if she enjoys it. We'll see what happens.
You have certainly found a caring woman who was willing to listen actively and hear you out... that in itself is a gold mine. Best of luck in your journey!
Start off slow. Make a game out of it where you lock in the morning and she holds the key all day until you earn an unlock. Let it progress from there.