Question about frequency

[SoloHotwife4Fun]

Hello everyone, hubby and i have not been on here much due to having to move recently and he has had to focus on work more. But anyway, I have tried n tried to find any recommendations for my question, but I keep running into more “fantasy” answers and almost always assuming the hotwife has a bull/boyfriend. So, here is my question…

How often should I humiliate/degrade him and keep it fresh and not “contrived”? if that makes sense. I am not currently dating anyone but I am looking - the problem is that we moved to a large retirement community (not really by choice, long story) which has resulted in a demographic that is mostly not what I am seeking. Its a no-brainer to continuously humiliate and degrade hubby when I’m dating someone, but its much harder to do that when you AREN’T seeing someone.

I want to also admit that I find it very difficult to maintain consistency humiliating him. For example, a few weekends ago he tried a pair of my panties on, liked them, we talked a little, and I ended up giving him several pairs of panties and suggested he try them full-time. The did that for about a week, but I probably mistakenly did not say a lot about it, so after a week, he went back to wearing regular underwear since I wasn’t saying anything. I don’t know what to say or how often to say it, without it sounding “fake” or “fantasy” like, if that makes sense.

If you are familiar with us (we both have profiles on here), you will know he has an extremely tiny penis and thoroughly enjoys being a cuckold. While he is a natural at being a cuck, I am feeling like being a true “hotwife” is not as natural for me, but thats not to say Im against it and want to do better.

Thanks for any recommendations and will be happy to clarify if I’ve been too ambiguous with anything.

[Long Lurker 34]

SHW4F - You seem to have a lot going on.
- Where you moved to, are you of the same age as the retirement community?
- HWing does not mean your hubby HAS to be humiliated. If he doesn't mind it or enjoys it on some level, then as you do have the opportunity to 'date' then it's only fair to validate his enjoyment too.
- It doesn't have to be complicated. A number of small things done regularly can keep the vibe going.
- As you did with him wearing your underwear. But instead of one week, throw out his and buy him all new female underwear. In fact going shopping and have him right there as you select them. And include some sexy ones for date nights etc.

[SoloHotwife4Fun]

Thank you LL34!

SHW4F - You seem to have a lot going on.
- Where you moved to, are you of the same age as the retirement community?
Lord no! I am 49 and attracted to upper-30s lower-40s men, sometimes lower-50s but not as common. The minimum age in this area is 55, but the average seems to be more like 60s-70s - so honestly, not even close.

- HWing does not mean your hubby HAS to be humiliated. If he doesn't mind it or enjoys it on some level, then as you do have the opportunity to 'date' then it's only fair to validate his enjoyment too.
He wants it and does not appear to be limited by how extreme it is. Part of my problem is that I do love him, so its not always something I strive to do 24/7, and another part of the problem is Im not seeing anyone, so I dont have the “comparison” thing right now.

- It doesn't have to be complicated. A number of small things done regularly can keep the vibe going.
What is “regular”? I am not great at being creative here to keep things fresh or is it ok to say the same things over n over?

- As you did with him wearing your underwear. But instead of one week, throw out his and buy him all new female underwear. In fact going shopping and have him right there as you select them. And include some sexy ones for date nights etc.
So basically remove the option for him…never thought about that approach, thank you!

[Long Lurker 34]

Thank you LL34!

SHW4F - You seem to have a lot going on.
- Where you moved to, are you of the same age as the retirement community?
Lord no! I am 49 and attracted to upper-30s lower-40s men, sometimes lower-50s but not as common. The minimum age in this area is 55, but the average seems to be more like 60s-70s - so honestly, not even close.

- HWing does not mean your hubby HAS to be humiliated. If he doesn't mind it or enjoys it on some level, then as you do have the opportunity to 'date' then it's only fair to validate his enjoyment too.
He wants it and does not appear to be limited by how extreme it is. Part of my problem is that I do love him, so its not always something I strive to do 24/7, and another part of the problem is Im not seeing anyone, so I dont have the “comparison” thing right now.

- It doesn't have to be complicated. A number of small things done regularly can keep the vibe going.
What is “regular”? I am not great at being creative here to keep things fresh or is it ok to say the same things over n over?

- As you did with him wearing your underwear. But instead of one week, throw out his and buy him all new female underwear. In fact going shopping and have him right there as you select them. And include some sexy ones for date nights etc.
So basically remove the option for him…never thought about that approach, thank you!

SHW4F - I get that, so find things to turn his crank because you love him.
- Do some reading and ask questions on the forums here make some notes about what other women do that you could try. Not everything will be successful. Sort of learn as you go.
- Samethings over and over. That's ok for somethings but you should work on expanding activities and what or how you say things.
- you could do the same with PJ's too, get him some female nighties, babydolls etc. Think of regular or sexy items.
- You've probably read somewhere on here about cock cages. Investigate that angle.
- If you want to subtly humiliate him in public tell him he has to walk three paces behind you at all times, unless you point the ground right behind you. In that you are always in front of him. Tell him he will always open doors for you, the one time he go in front. Others might see that as being polite and others would see that as you having more power. Little things.

[kellycuckoldsmark]

My wife Kelly has the same challenge. When she is seeing someone or planning to, the need to build denial, humiliation and the mind games come naturally to her. She finds it doesn't come as naturally when she isn't seeing someone as she isn't a mean cuckoldress she just enjoys the sex with other guys.
We can go weeks or even sometimes months without her seeing someone given life and the difficulty of finding people. Things definitely slow down a little and after times when I would get down because it felt like my needs were forgotten (strange I know) she found that she actually needed to be deliberate about it. So she put a reminder in her iPhone for every couple of days to do something. Examples could be caging me while she plays with her toy and teasing me in the cage and leaving me unfinished; if we go out with friends where she likes the guy (but NEVER sleeps with friends) she makes me wear a cage or a pair of panties. Just generally all the stuff we do when she is seeing someone but the reminders help her with frequency when she isn't as motivated.

Has worked out great for us. As always in this life, communicate and keep sharing each others needs and enjoy.

[WishMeCuck]

Have you thought about exploring new venues?

If he likes to use panties, he may get excited with the prospect of being made a man's bitch (as a humiliation/submission play). I know, not all man that enjoys wearing panties necessarily want that, but quite a few do and many of them are too shy to admit it.
And this is not being gay, it is really another aspect of humiliation and submission that so many cucks enjoy. In a way, kneeing down to suck a cock or bending over to a man can be the ultimate humiliation or submission. And there is the joys of anal penetration which can be really pleasurable, especially to man.

That could open up lots of new things to do. From anal play, to role play, pegging, shaving/waxing his ass, anal stretching, getting him to wear anal plugs, and even finding him a bull. Meanwhile, you could even put him on a cage and say there is no need for his useless dick, he will now get his pleasure from his boy's pussy.

[little sissy Benita]

Every cuckold relationship is dfferent.
How often you should humiliate/degrade him, i can´t say, because i don´t know your situation.
When he like to wear panties - that´s ok - maybe he can wear panties daily.

Does your bf/lover knows that he like to wear panties - is it embarrassing for you cuckold to wear them in front of your bf/lover?

I know how it is to have a tiny willie - i never satisfy my fomer wife - mostly i was ready in two minutes. And i was also not sexual active, for me is cuckolding best for all. At begin it was very embarrassing to accept my new role in the family - as her little daughter. My former wife means, tiny willies like mine belong into diapers - and cuckolds like me deserve treat like little girls/babies.

The embarrassing/humilation faktor was at begin very high - Although at first I only wore these things occasionally (dresses, skirts, diapers and so on).Then the wearing times became longer until it was 24/7.
Maybe you'll get more used to it over time, probably yes

little Benita

[Celesissy]

Have you asked him how he would like to be humiliated? He may come up with things that surprise you, from being dressed as a sissy maid or being gradually turned into an adult baby every night in his own “nursery”. Now those are two of my particular desires and they won’t be for everyone, but I’m sure he will harbour some fetish that he would like you to do to him, and rather than guess, much better to tease them out of him. If you’re unsure when to ask them
In the build up to orgasm when giving him pleasure is in my view the best time for a man to blurt out his secret desires.

[SDB2014]

Have you asked him how he would like to be humiliated? He may come up with things that surprise you, from being dressed as a sissy maid or being gradually turned into an adult baby every night in his own “nursery”. Now those are two of my particular desires and they won’t be for everyone, but I’m sure he will harbour some fetish that he would like you to do to him, and rather than guess, much better to tease them out of him. If you’re unsure when to ask them
In the build up to orgasm when giving him pleasure is in my view the best time for a man to blurt out his secret desires.