Crossdressing hubbies?

I've dressed since a small child, always in secret. I'm definitely on the trans spectrum and now often (about once or twice a month) go out in public presenting (respectfully dressed, and reasonably passable) as female (with similar friends). Even been out shopping in daylight like this. Yes, my wife does know. And supports me, often buying me things to wear.

BUT I've not (yet?) dressed while in a cuckold scenario. I've kept it quite seperate, because I don't generally see my dressing as sexual.

However, I do think about it. A lot. But not so much as I normally dress en femme. Specifically, the sissy thing does turn me on (pink lingerie, lacey girl socks, frilly knickers, bra, babydoll, etc.), probably because of the humiliation angle. I also think often about dressing as a schoolgirl while a guy is fucking her. It just feels soooo submissive. I think it is only a matter of time before I do it.
 
I dress every time she goes out with any of her boyfriends, but i’ve always crossdressed, from when i was a young boy. I wear her clothes, and although she knows im bi, she does not know i love to crossdress. I would like to incorporate it to our lifestyle for the humiliation, but i dont know how she would take it
 
Nathaniel, I understand your retiscence to tell her. I think that there is often that conflict present, between wanting to express your emmasculated sub self to the full, versus wanting to still have her respect and love. I think it just boils down to communication & taking the time to explain it. Doesn't mean it's any easier to bring up mind. But I think these things are often bigger in our own minds than others'.

Telling both my wife and my daughter, as well as my siblings about my genderfluidity turned out to be minimal events in reality, with my daughter overjoyed that I was able to do my own thing & get out there in public.
 
I would crossdress if I thought I could pull it off. I am not feminine at all. The most I’ve done is wear my wife’s panties without her knowledge m

You honestly can't tell what is possible until you try. Maybe try booking into a dressing service - you'd be amazed at what is possible with makeup, silicone and the right clothes.
 
You honestly can't tell what is possible until you try. Maybe try booking into a dressing service - you'd be amazed at what is possible with makeup, silicone and the right clothes.
Lol. Thank you but I’m 6 foot 2 with long skinny unattractive legs and I have not shaved my mustache in 40 years. I do keep my pubes and ass shaved but that won’t help look sexy in drag.
 
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I do it when she is away. Few months back I shared my girly fantasy with her. Now when we get some us time together She treats me like a girl. Dominates me kisses me, spanks me... etc I often wear her panties at work. Sometimes when we run out of washed ones she offers soiled ones. In our verification pic I am wearing her pink panty ;-) our relationship has definitely blossomed after I shared all my fantasies with her !
 
I do it when she is away. Few months back I shared my girly fantasy with her. Now when we get some us time together She treats me like a girl. Dominates me kisses me, spanks me... etc I often wear her panties at work. Sometimes when we run out of washed ones she offers soiled ones. In our verification pic I am wearing her pink panty ;-) our relationship has definitely blossomed after I shared all my fantasies with her !
I have worn panties a couple of times and felt sexy.Had trouble keeping my cock in, especially when it got hard. Wish I could pull off the full drag dressing but if you ever saw me you’d know why. But I love seeing men who can pull it off. I think they are sexy.
 
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