Question for the mistresses, goddesses and KH's...

Not regularly but I do like getting him to wear other outfits.

 

Personally while I love having my guy locked up and desperate for release, I'm not a fan of dressing him up as a sissy or crossdressing.

In my mind he's a man and that's how I want him to look. I just want to also be able to make him insanely horny and increase the anticipation of when when/if he'll be allowed to cum.

But that's just my take, and to each their own.

 

Sorry for answering o my KH wife's behalf
She never liked the idea of my cross dressing or using any of those women's cosmetics
She likes and has always liked to see me as a (caged) man

 

jemima already cross dressed long before we met. she doesn't really look too good as a man.

 

I like my man to be manly and strong. It gives me more of a rush knowing that I control something very powerful and stronger than me. I use the cock cage to tame the wild beast and holding the key makes me very powerful. That being said, I do like it occasionally when he is dressed up in women's clothes for the humiliation and fear of being seen, side of it. I always threaten him that I will parade him around outside or in front of my girlfriends... even though I have never done so.... ...yet, that is.

 

I only went down the path of crossdressing and sissy/feminisation training after I discovered my husbands fetish for panties and other silky lingerie and female things. I realized I could leverage it as another tool for my control. Its not really attractive or a turnon for me, but the results are, so thats why I do it.

Ms Karen

 

I discovered I liked it by accident after I used it as a 'security measure'. I had to work and he went out to a bar. I have insecurity issues, so I figured if he wore my underwear, he'd be too embarrassed to undress in front of another woman or she'd freak out and kick him out. I came home and saw him asleep in the bed with just my underwear on and thought it was cute and sexy, so I woke him up and had my way with him.

I asked him why he wore it to sleep, and he said he wanted me to see he didn't take it off in the bar. He didn't like wearing it when he went to the bar, which is how I learned about male chastity.

I started dressing him up more and more just for sex, but I also discovered he was more submissive when he was dressed up. I don't have any problem getting him to dress up because he associates it with sex thanks to the early days of me dressing him up. He even has special lingerie and dresses for discipline or play, but if I tell him to dress for a disciplinary session, he does it right away. He might complain a little bit because he doesn't want to get a spanking, but he always goes and gets dressed.

Also, I have a ritual for him when I'm putting him in disciplinary chastity where he has to put on lingerie reserved just for that.

So yes, turning him into a sissy is a major part of chastity and me controlling him or disciplining him for masturbating and watching porn.

 

Nope, big turn off for me and I would suggest, most women. I might just about stretch to making him wear a pair of panties for a laugh, but never have.
I think it's a major issue for guys trying to get their wives interested in chastity. When I search for anything online I not only find chastity info but cuckolding and cross dressing mixed up with it. Both of those are an anathema to many women and so it really frustrates your chances of getting them into the chastity part.
For example, I have been here a few weeks now and it's been quite friendly and informative. But then I clicked on the gallery for the first time this weekend.
OMG... if I'd clicked that before now I'd have never visited the site again, and I'm VERY kinky.

You can sell chastity to a woman on lots of positive benefits, more intimacy and more orgasms and oral sex being my particular favourites. However it takes a MUCH more dominant woman to want to sissify a guy, and as if SHE'S initiating the desire to cuckold you then you've got a whole other set of issues to deal with already.

I can imagine someone really getting into chastity for their guy and then POSSIBLY moving from that to cross dressing him if it grows into a strong Female Led Relationship but my guess would be that's incredibly rare for someone YOU are trying to get interested in these things.