Very long request for advice!

Hi, new here (after lurking for a while), and would appreciate any advice or perspectives on where I/we are up to, what it actually is that I'm trying to head towards, and how I might get us there. Partly I'm trying to think things through out loud, so apologies in advance if this is long and/or boring! If no one replies, at least I can do some thinking.

* tldr: I've admitted my cuckold fantasy (mostly) to my wife, stuck after a little progress, and not sure where to go from here. *

I'm 45 and my wife Anna is 46. We've been married for almost 20 years, and have 2 kids still just preteen. We're both public-facing professionals (so there's an extra barrier to this lifestyle), and our life is very busy.

Like most long relationships, we've had our share of ups and downs. We almost split (or did for a short period) a few years ago, but things are emotionally better now than they probably ever have been. Our sex life is extremely limited at the moment and has been for ages, partly due to our kids (both are neurodivergent and need a lot of managing) and partly due to work and stress - when we have time together though (and assuming we don't immediately crash out!) we still have good sex.

Anna is extremely conscious of her age and weight - she's curvier than she wishes, but I've never liked skinny girls, and she is constantly assumed to be in her 30s, but still often feels bad about how she looks. I should also say (and this isn't my bias as her husband), she's always been a total stunner - her fears are so misplaced. She also doesn't know, because it would have been weird to say before and now feels implausible, but I've always had a massive thing for large, older ladies, even very large and into their 60s - pretty much from adolescence. So she's more and more sexy to me the older and larger she gets, but she doesn't really believe it.

Over the time we've been together, I've very slowly tried to figure myself out sexually. I'm very broad and very curious. Despite being very intrigued by trans women, I identify as 100% straight - I'm attracted to femininity exclusively. I'm also very loyal, never having played away (if we edit out a few kisses here and there). I guess I have a strong voyeuristic streak as my (previous but lifelong) primary sexual fantasy was watching two women have sex together - not with me.

The cuckold thing crept up on me because (although she initially told me the opposite because she knew it turned me on), Anna is, sadly, also 100% heterosexual. Much as I wanted to fantasise about watching her with another woman, this fantasy faded as I realised she was only pretending, and it didn't do anything for her. However, that fantasy did introduce the idea of me watching Anna have sex with someone else from the very start of our relationship.

I can't remember how my imagining of Anna with another woman somehow became an increasingly intense cuckold fantasy, but it so did. Confusing, and at first very 'out there' before I realised there were words for this. It quickly became fantasy number one.

Anna, despite loving sex, enjoying attention from others, and being at least partly willing to fantasise with me, is mostly quite conventional. She likes to be controlled in the bedroom, but that's something I'm not the best at - we might both be at the same end of the bdsm scale! - and she does like the danger of being seen or caught. She has admitted to me that one of her best fantasies is to have a 3 or 4some, being fucked by 3 men at once - this is brilliant, and is the one area where she might at least imagine having sex with someone else - but whilst fun and definitely something I'd be up for, I know it's not something Anna can picture doing in real life, and her fantasy is that I'm involved. Beyond that, though, she's quite conservative, even judgy.

I introduced my cuckold fantasy, maybe 10 years ago, by the cowardly means of telling Anna about an extremely erotic dream about watching her with another man, and saying how surprised I was that it was so erotic I came. It was actually partly true, but certainly wasn't a surprise to me, and I admit I 'improved' the dream to fit with what I know to be her tastes.

Since that point, it's been out there, but not always fine. At first, she went with it a bit, as a new fantasy. We talked it up in the bedroom, and I got Anna to come really hard thinking about it a few times, but it wasn't always ok, and sometimes can make her feel worried or confused. Sometimes she will say something like "I just wish I was enough for you on my own", or other times will ask something clearly designed to check whether actually I'm the one who wants sex with men (I'm not), or if I'm just looking for a hall pass (I'm not). Alcohol tends to change things quite a lot, but even then it's still not very predictable how it might go down - and it's almost always me who brings it up.

I know what you're thinking - she's just not into it! It happens! Either save it for alone time, or get divorced and find someone who is into it! But I wasn't at all into it previously, actually I'd say it was a real turnoff (the straight version). And actually now I'm laying my thoughts out here, I realise that I'm hanging onto the hope that this all isn't just me partly because some of this for me has developed because of Anna.

For instance, she has a very clear 'type' when it comes to men. Sometimes she's teased me in the past because someone on TV or in the street was so obviously her type that we both knew she fancied him. I'm a bit her type, but I know I don't tick every box.

Also, Anna likes attention, especially from men. Good, you might think - but I haven't had very much success using that as a way in. AFAIK Anna is faithful. It's possible she dated during our separation, but she claims not, and even if she did I hugely doubt anything happened . ...... times have definitely been more interesting in the past - before my turning on to this, there were some times I look back on and wish that could happen again.

...... Anna is probably the way to go here. It's not that she gets so ...... she can't consent or anything - just very quickly her morals seem to change a bit. Not totally different, just - a bit. In the past we've, for example, ended up at some guy's house, who clearly wants to get into my wife's knickers, and takes every opportunity to be alone with her - but that was before, so I was not happy. ...... Anna seems to flirt without realising it, and seems genuinely unaware that this wasn't 'we just went back to a guy's house so we could carry on drinking' (which is what ended up happening), but actually from the guy's perspective something else entirely.

What a twat I was! There were fairly regular situations like that at one point, and all I could do was get angry and jealous! We'd go home arguing instead of horny. I'm hard now just thinking of what could have happened. I try to convince myself maybe something did, at least once or twice, but I really don't think so.

I've tried to recreate those situations since realising what was being woken up in me, with mixed results. Probably the closest was quite recently, and for once I was right on it, but tbh I think the only two people up for it were me and him - Anna was just sort of doing her thing. Also it was awkward because all our friends were around. But it did lead to some progress in

Anna got heavily chatted up by a guy in his 20s and didn't tell him where to go - a couple of friends alerted me, and I told them I'd keep an eye on them (which I very much did!). Then the guy came over and said he needed to apologise as someone had told him the girl he was coming onto was a married woman and I was the husband. I think he was scared I'd suddenly drag him outside or something, but instead I took the chance and said something like "hey, I don't own Anna - she's hot, so men do speak to her, don't worry. To be honest, as long as they're gentlemen I quite like it. Look after her and it's not up to me what happens!" As he went back to Anna I think I said "good luck" or something.

I then tried to hide the bulge in my trousers and at the same time field curious responses from friends (I pretty much admitted it turned me on when she got chatted up). Sadly it didn't continue for much longer - I don't know what was said, but I think probably he was braver and more direct after we spoke, and then maybe Anna said she wasn't interested.

However, not very long after that, one of us brought that night up again, and we had a little bit of a conversation. I think maybe I'd mentioned it with a wink a few times, and then on one of those occasions Anna decided to stop batting it away. It wasn't everything I hoped, but it gave me some MAJOR material to fuel my fantasy. I will try to capture the essence here.

So I think I said something flirty about the amount of time she spent talking to some guy who was both her type and younger than me, and Anna responded with something about me having to keep on my toes. I laughed and said I think I like being kept on my toes. Anna said something about me not even noticing that she was being chatted up, and I laughed and said "of course I did, I even spoke to him at one point!" - which surprised her.

"Well, he gave me his number when he left, so maybe you need to speak to him again!"

Fucking hell! She said it in her joking/not joking winding me up voice, but I think it was intended to make me panic. It half worked, but I managed to keep my focus. "Really?! Jesus. That was brave of him. Especially after talking to your husband!"

"Why didn't you stop him or take me away?" she asked.

"I thought it looked like you were ok, and I kept an extremely close watch on you." I replied.

"Weren't you jealous?" she asked, sounding slightly hurt.

"Oh god yes!" I said straight away, smiling, and added "jealous and turned on!"

She looked at me. "I don't get how that works."

"Neither do I. But it does seem to."

"What, like it turns you on when guys fancy me?"

"Yes!" That didn't feel too weird. Then I thought for a moment and added, a bit quietly, "And when you fancy them."

She studied me, possibly looking for signs I was winding her up. "You like it when I fancy other people."

I couldn't quite read her. Suddenly anxious, I filled in the silence: "I know it's weird. I don't know what it is, but ever since that dream..."

She knew which dream I meant. "So it turns you on to think of me with someone else."

She's not giving me much to go on here! I'm right out on a limb. Not sure if I'm climbing a mountain or digging a hole. "It really does. It's just so.... erotic. You're so sexy to me, I just love to see you being sexual. And if it was with someone who wasn't me, it's like this intense extra feeling, like anger and jealousy somehow add to the excitement..." I was losing faith in my words. I was still getting very little back.

" So you'd have let him fuck me?" Anna remained hard to read, though looked slightly hurt again. She loves to tease, but there's always a very fine line between that and meaning it. I think sometimes she doesn't know.

My mouth was dry. I was so so so turned on by the conversation, and at Anna's words I thought my jeans might literally burst open, but I still wasn't sure what Anna was thinking. I knew what I was thinking though, and I didn't want to waste this possible opportunity.

"Maybe" I answered, trying to sound sexy instead of scared. "Maybe I'd have watched."

The ground shifted slightly. I think Anna decided to jab my jealousy to try to bring me back to my previous familiar, mildly possessive self. "Well," she said, "you should be careful. You know I wouldn't be interested in just having sex with someone without a relationship. I'd need more than that."

Oh, Anna. If you were trying to put me off, you've messed up big time. You've wandered into the middle of my hottest fantasy! I've realised that my ultimate fantasy isn't all of the sexual extremity pictured by most men in these internet niches, but something stranger: I want my wife to have a boyfriend. Like, a proper one, with romance and going to work and family events together. I don't get it at all, but I even get turned on by the thought of him ...... over in my bed with Anna, with me on the sofa listening from downstairs.

I want to help her get ready for dates, and sit all night waiting by the window with a hard on until they come back. And, hotter even than watching my wife get fucked by another man, I constantly fantasise about her making out with him. I think part of it is that I love the thought of being married to a slut; but somehow the best version of that for me is a married woman who has a boyfriend. That's hot as fuck to me!

But because I think it was intended to turn me off, like it would 99% of other men, as well as me a few years ago, I didn't fast forward to offering to phone him right now, and instead came up with "Wow. ....... That's an interesting thought."

At this, Anna was a bit more readable again. I think she decided at that moment that I was in 'anything you say will turn me on even more' mode, and it was no longer a helpful conversation. Which is probably true. I can't remember exactly how it ended, but I knew I'd at least confessed to more of my fantasy than I ever had - and was still married afterwards!

So if anyone is still with me after all that, any thoughts or advice would be very much appreciated!

Is this fantasy entirely coming from me?

Am I missing anything obvious about my approach or Anna's response?

What's your best guess at how Anna is feeling about this at the moment?

And if there's any hope for this fantasy to become anything more than that, what would you do if you were me to try to progress it?

Thanks for the time and space to think like this.