My new beginnings with a new partner

As you may have seen from my older posts, I was previously married and in a consensual cuckold dynamic with my now ex-wife, which led to some incredible experiences. We've since divorced, but we've maintained a positive friendship and now enjoy our separate lives here in Australia.

I've recently started a relationship with an incredible woman — I'm completely taken by her, both her beauty and who she is as a person. For a long time, I tried to push aside my past cuck interests, but naturally, conversations about past relationships and experiences came up. She shared that she enjoys attention and has, at times, given in to that temptation, which opened the door for me to be honest about my own past dynamic.

She's intrigued by it all and the psychology behind it. While she's made it clear that humiliation isn't something she's comfortable exploring, she has said she'd consider aspects like chastity if there's a genuine connection involved. It's honestly blown my mind —
the idea that this amazing woman might be open to exploring that side of things with me while we continue building what we have together.

We're now working through what the chastity dynamic might look like — how long, what feels right, and making sure it's something that's genuinely rewarding for both of us.

She gets plenty of attention and plans to explore that gradually, starting with a bit of flirting and seeing where real connections might develop over time. What's really surprised me is how much thought she's already put into it — she's been looking into FLR dynamics and the idea of keyholding, not just over me but potentially extending that dynamic to other men as well, which adds a whole new dimension to things.

She's approaching it in a completely different way to my ex, and it's exciting to see how naturally it seems to fit her mindset.

I'm hoping to keep sharing updates like I have in the past and bring you along for the journey
Droopy and Miss

This is exactly the kind of journey people love to follow here.

What really stands out is how naturally this is evolving for you — no forcing, no rushing, just honest conversations and mutual curiosity. That's usually where the strongest dynamics come from.

Also respect for being open about your past and giving her space to shape this in her own way. The fact that she's already thinking about FLR and keyholding on her own says a lot — that kind of mindset can take things to a very deep level over time.

And honestly, starting with connection, trust, and small steps (like flirting and attention) is the smartest way to build something long-term and real.

Curious to see how your version of this dynamic develops — especially since it's already clearly different from your previous experience.

Keep the updates coming. I have a feeling a lot of people here will relate to this path.

A second bite at the cherry! Lucky you! ...with a different journey.

Looking forward to hearing more.
Interestingly, someone dislikes my work enough to take the time to give me minus points!

AI used protect my Princesses 👸face identity. Back when I first posted my cuckold journey we has to use Microsoft Paint 😂. More pics to come on our journee
Droopy and Miss

She looks stunning and I love her key nestling in between her glorious breasts. No wonder she gets so much attention ❤️😈 x

Your new partner looks fantastic. I'm really looking forward to seeing how things develop. There's something magical about every new beginning....

Testing the waters tonight... heading back to one of her old haunts—the kind of place where the drinks flow, the music hits just right, and inhibitions tend to slip. I'll be by her side to start, but at some point I might disappear into the background... let her feel the room without me right there, watch from a distance as the energy builds and see exactly what unfolds when she thinks no one's watching.
Droopy and Miss

Photos she uses to tease me
Droopy and Miss

Me and my Princess out in the CBD... and she's pure trouble tonight. Every step she takes, eyes lock onto her—men can't help themselves, slowing down, turning back for that second look. And she knows exactly what she's doing. That little smirk, the way she leans in close to me, brushing past just enough to tease... it's all deliberate.
She's soaking up every ounce of attention, letting it build, letting me feel it too—keeping me right on edge while she plays.
And later... I'll disappear. Let her think she's alone for a while. Watch from a distance as the tension unfolds... see who gets brave enough to step closer, and just how far she lets it go.
Droopy and Miss

So last night was fun! Princess gots lots of attention and she loved it!! So did I!!When I finally went off for a while with her knowing she got a lot of attention.
We spoke during the date how we go forward, she is going to let things happen naturally and she has said she will " attract and not chase
We have decided together Chastity will happen once she goes on first date and finds a connection.
I have looked back on my old posts and realised that everything has changed especially with the ability to connect to people ,social media etc and how easy it is for people to contact each other because the only way really was this site when I first had cuck fantasies.
Looking forward to see what happens
Droopy and Miss

So we discussed chastity play and some release schedules that could work.
This is all hypothetical at the moment but she did say and something that is horny and scary at the same time!!!!
" Careful what you wish for "
She jokingly said maybe twice a year!!! If she is satisfied by her lover's
She has a lot of friend requests on various social media platforms and some are brave enough to ask her to meet for a drink but at the moment nobody is peaking her interest.
Watch this space!
Droopy and Miss

So 11pm Monday night here in Australia, late night phone call with my girl, potentially a date this weekend with someone who has been asking her out for a drink. I so wish I was in chastity cage right now!! It's going to be a long week to see how this develops
Droopy and Miss

Careful what I wish for !
Tried a new cage which I have the key for compared to my old one which my partner has the key to the padlock for but sent the photo to her , which I'm sharing with you now.
Waiting for her to decide which cage she wants me in for the week as potentially has a date this weekend!
Thoughts??
Droopy and Miss

shankly
The new cage suits you better. Give her the keys for that one.

Thanks for the take, Montypython. I gave the smaller cage a run for a few hours and—somehow—managed my way back into freedom. The other one's a different beast altogether... anti pull-out pin and no easy escape. That one keeps me very honest. Think it's time we upgrade to something properly secure if we're serious about long-term chastity—something that leaves no doubt who's in control.
She's definitely warming to the whole keyholding dynamic... the idea that I can't get out unless she decides I can? That power shift has her curious—in the best way.
Things are heating up on her side too. She's got drinks lined up Thursday with a younger guy she's into... that should be interesting. Then another date Saturday—someone who slid into her Facebook. Details are still unfolding there.
Can't lie... the thought of her exploring, having options, maybe even multiple lovers—it's got a certain edge to it that I'm starting to really enjoy
Droopy and Miss

Hopefully get more details soon! On the dates with potential suitors
My girl is picking me up and giving me a lift to an appointment in the city.
We live separately and have joint custody of ******** from our previous relationships.
So trying to juggle a home, kids on a joint custody agreement and somehow have a relationship and a cuckold one on the side is a bit to juggle, but fun also 😂
Droopy and Miss

Apologies for no update.
Sadly life events have meant we have paused meeting anyone this weekend
Still in Chastity
Droopy and Miss

Love your updates. We both enjoy your story and your journey

As long you're in chastity, all good. Keep us updated.
it might be painful

Yes still in chastity. Sorry for no updates, she was supposed to go on date Thursday and Saturday but sadly we had to change plans quickly and sorry won't explain ourselves on this platform.
Hopefully in the next week things will change and we can share photos and updates of her adventures
Droopy and Miss

Update
Sadly we have had to pause our new relationship/ adventures
My girl still has her suitors chasing her but for now she will not follow through with anyone.
You folks will be the first to know
Droopy and Miss

So big update
Has dinner plans this Thursday with an old work colleague who fancies her but my girl is not interested but at least she is tipping her toes in.
Biggest update she is flirting with a fireman who is 10 years younger who has a hot body in her words, photos have been exchanged and she loves texting him in my company, hopefully a date at the weekend!!!
Droopy and Miss

So happy to hear you've been able to restart the cuck lifestyle, even if it's facing some hurdles. But it'll all be worth it! I remember reading your older posts as well so I know just how much it means to you to have a hotwife keyholder. Best wishes for your lives together moving forward.

Photo from her date tonight
Caged and frustrated
Sadly wasn't there to help get her ready due to living separately and family commitments
But OMG she looks hot!
Droopy and Miss

She's very hot and willing to be fucked

So her initial tipping toes in the water went well!
He was a perfect gentleman and treated her amazingly, she has mixed feelings about it so will see what happens
Her next date is the interesting one 10 years younger and a firefighter and she is getting excited at future events she always smiles when he texts ! But I've been here before with potential young men so trying to keep positive for her as this is all new to her!!
Will keep you updated
Droopy and Miss

Bravo Shanks
And thank you for sharing your new exciting adventure.
I only tend to dip infrequently these days, but it is great to see one of the long time posters still here.
The excitement and dare I say it slow "Progression" must have you constantly on edge and a wonderful open partner to share the journey with.
Much respect