My life in chastity and moving from a fun cuckold to a real cuckold

Discussion in 'Introductions' started by joecool722, Jul 8, 2016.

  1. joecool722

    joecool722 Member

    Sep 18, 2014
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    So where to begin.

    I’m 37 now and I’ve been into kink since I was a kid.

    I was online before the internet, downloading porn when it was still acquired over old modems and BBS’s.

    As a young kid I was always excited about bondage. Since I was years away from having any type of partnered interaction, I stumbled upon self-bondage. That eventually led me to Altarboy’s site and it was all downhill from there.

    I got into computers and started working professionally in that field when I was 17. I never really had any luck with girls during my teenage years and eventually went down to “Boystown” in Laredo where prostitution is legal and lost my virginity to get it over with.

    When I was 21, the company I worked for transferred me to another state and I met the woman that would soon be my wife/mistress.

    We started dating and were kinky from the word “go”. She was engaged to someone who was long distance and dating someone local. I joined in dating her and on our first date she told me she was kinky, and she had never been faithful to a man in any of her relationships. (She was 30 to my 21 and divorced). I told her I had no problem with that as long as I got to watch. She liked that answer and off we went.

    I disclosed my chastity fetish which was in full gear by then and she had no issues with it. Our first sexual encounter involved me going down on her (first time ever for me) while she had phone sex with her fiancé.

    Eventually she ended things with her fiancé and her other FWB who was local and we moved in together. She never really played with anyone else for until about 3-4 years in. She always had permission. We got into the local BDSM scene which was very large and active in the town we were in and she started playing various people. She met one guy who had a huge cock (9in, no exaggeration). She would play him and then give him a handjob at local kind parties and we would get a crowd of women gathering to look at the huge cock.

    After a lot of discussion, Judith disclosed that she was really a size queen. I was by far the smallest man she had ever been with (4.5 in) and playing with this new guy had reminded her how much she really enjoyed a big dick and wanted to fuck a man with a big dick. This wasn’t something she said lightly or casually and it was really only after a lot of prying. Years later when she was much more comfortable with our dynamic and her dominance, she told me that when we first had sex she was terribly disappointed. I was really small and didn’t last very long. I was very trainable and she trained me to give really great oral so that was the basis for continuing on our sexual relationship.

    So the years went on. We played with BDSM, we played with other people, we played with chastity. I bought a CB-3000 when they were still being custom made. Over the years we never really found anything that worked.

    At about 10 years into our marriage, my wife started playing people more often and I became a willing cuckold. She had technically cuckolded me with the guy with the huge cock many years prior, but they only had sex a couple of times.

    This time she had found what started off as a bull and eventually became a poly partner. He was also submissive, but he is a real man’s man. I’m 5’8”, chubby, not very physically fit etc. Her new guy is 6’3” and I shit you not was in the Special Forces in the military. Very much the Alpha male. She was still the Domme, and we were both her slaves, but I was on the bottom in every possible sense of the word. Eventually things became very serious with him, she formally collared him and he moved in. For about 3 years, we operated as a very fun Femdom/cuckold/poly triad. Later after much discussion, we decided that the roles would more formally change and I would no longer be considered her husband, I would be her cuckold. We would legally stay married for the various benefits that it affords, but to the outside world, he would be her husband. I didn’t wear a ring any longer and he did. It was quite a wild experience.

    Right about that time I was fully cut off from penetrative sex with her. With one exception a few years ago, the last time we had sex was Dec 2009.

    Unfortunately, the fairy tale didn’t survive indefinitely. I started struggling with depression and health issues and after lots of counseling and what not, we agreed that things were over. Last time we had any sexual contact was April 2014, so it’s been over 2 years now.

    Being poly, we didn’t take the typical approach to our separation though. We are still legally married and we live in a very large house. She lives in the large master suite with her new “husband” and I live in a second master on a different floor. We have a very good relationship now, but not in a romantic sense. We are good friends, we share expenses, we are there for each other and things are good. I spent the last couple of years working through my depression with a therapist and now feel like I’m getting on the other side of things and looking at dating etc.

    I guess it's kind of the be careful what you wish for cuckold edition. For at the end of the day, I have essentially become a real cuckold. But probably not in the really unpleasant way.

    So anyway, that’s the general story of me, so far.

    Specifically going back to chastity, my history is as follows:

    First chastity device was an early era CB-3000. Quickly found that it was not secure at all as I’m a grower.

    I got pierced with a frenum piercing to hopefully secure a chastity device. That never worked. Did a PA, same thing. Problem I always have is aside from only being 4.5in when hard is that I’m an extreme “grower” so when I’m flaccid I’m practically inverted. So any piercing related security measure always ended up being too painful when I got flaccid.

    We even did a series of Jacob’s ladders (3 ladders of 7 rungs each) in an idea that we would eventually put rings through them all and then do chainmail rings to connect the ladders. Cool idea, but they all migrated (grumble).

    Tried a Lori’s tube during all that and of course it didn’t work due to the pull on the piercing. Tried a handcuff style steel tube thinking I’d secure something around my waste to keep it on, but at the end of the day, I was still able to get out.

    Then found out much to my annoyance that since I wasn’t very big, after a week or two of chastity I was one of those people that could wiggle the CB-3k and eventually squirt.

    We pretty much gave up on devices at that point and decided to go the honor system route. My record for longest time without an orgasm is 46 days, and that was on the honor system.

    Mixed in with all my chastity fantasies where fantasies of being a eunuch or having a penectomy (I wanted to make sure I still kept the desire). This led to learning about elastrators and banding and eventually penis banding. We did a lot of that for a while and found that if I banded very deeply, right at the pelvic base, I would be completely numb anywhere I could try to masturbate. I had finally found a way to actually be chaste. Of course (for better or worse) we came upon that discovery just as our relationship had transitioned out of the sexual/romantic version.

    So I had a working way to be chaste, but no one to be chaste for.

    I have a lot of experience with banding and have done lots of it over the years, so I’m happy to provide advice on it, although BlueEyes has covered it pretty well in the forums. Wish I had found a post like that 10 years ago!

    Anyway, so that’s me!
    seasoned likes this.
  2. xcitedsisssy

    xcitedsisssy cd/sissy michelle

    Jun 18, 2008
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    Well @joecool722 that was quite the introduction. Anyway welcome to the Mansion.

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