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Jon68 From Vanilla Couple to Chastity Journey

member_55883c037a · 2026-08-27T20:33:29.000Z · 0 replies

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member_55883c037a Newcomer Thread starter
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2026-08-27T20:33:29.000Z #1

Hello all. My wife and I are relatively new to the world of chastity, and after discovering this community, we wanted to share our journey. I’m Jon, and my wife is Chris. We’ve been together for a long time (dot dot) and have shared 25 years of marriage. Truly soulmates in every sense.

We are both in our fifties, and calling our sex life ‘vanilla’ would be an understatement. I’ve always considered myself the more adventurous partner, while Chris openly admits that anything beyond missionary position is perverse to her. That said, despite the vanilla nature of our intimacy, we certainly enjoyed one another.

Everything shifted roughly four years ago when Chris began menopause and started experiencing significant pain during penetration. She visited the doctors repeatedly. We tried creams and lubricants, but it didn’t help much. There were countless herbal remedies, endless lube applications, and frequent doctor visits with little result.

As several years passed without enough discussion between us, we stopped trying to penetrate altogether. Over time, we both felt our relationship drifting apart. I was desperate to find a solution that would keep us connected, fearing the end of what we had.

I looked into porn sites for ways to enjoy sex without penetration—remembering how vanilla Chris is. Chastity caught my eye; although I’d seen it before and wasn’t initially interested, this time I took a closer look. Then came the lightbulb moment: perhaps chastity could work for us.

My logic was simple: if I am locked up because I’m not quite ‘good enough’ to have sex with my mistress, maybe that’s the answer we need. How naive of me! After much nervousness and sweaty palms, I sat Chris down and explained I wanted to wear a chastity cage. My hope was that she would behave in such a way that I’d be denied orgasm until she said so, always feeling ‘not good enough’ for her.

Chris looked at the device, made a face, but agreed purely out of desperation for our relationship’s sake.

After several weeks and trying different devices, we found a cage that was comfortable, and we settled into lockup. By the first week, I noticed a significant shift in my behavior: I became more tentative yet much more focused on Chris. As frustration grew within me, so did my desire to please her. Soon enough, I was showering her with affection, which she clearly enjoyed.

We moved at a pace—admittedly set mostly by me—which might have been too fast for Chris initially. Researching porn sites early on helped confirm that I was diving deep into chastity. While Chris went along with it, I could tell her enjoyment was somewhat limited at first. After several months of being caged about two weeks before release, small changes in Chris began to appear.

She started realizing we were getting along much better. This is when she became more assertive and confident outside the bedroom as I worked hard on becoming submissive. As the months rolled by, I watched this shy, vanilla girl transform into a woman who was increasingly confident, assertive, and dominant—not just in our daily lives but in bed too.

Before my eyes, Chris grew week by week into a powerful figure. She went from being someone who only had sex with the lights off to becoming a Mistress happy wearing leather and suspenders over Skype, demanding I watch her play with her toys while she locks me up when away from home.

Looking back at our vanilla years versus now, we seem like two completely different people. I am kinder, gentler, far more submissive, and definitely my Mistress’s slave. She is strong, confident, dominant, and very happy to discipline or punish her slave whenever it suits her.

That concludes my chat for now; we are pretty much up to date. Before I go, I’d advise all the guys and girls just starting their chastity journey: anyone can change if they truly want to. As a couple navigating this path together, I learned that you get better results moving at the pace of the more reluctant partner rather than pushing too hard. Good things come to those who wait.

I hope you enjoyed reading our story. Feel free to ask anything!

Stay safe, Jon and Chris.

member_40e7b90037

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