Lingerie

Which would your wife be more upset about, you cheating with another woman or you crossdressing ?
That’s a very good question, I’d have to say she’d be way more upset to find out I was screwing around behind her back. And that’s kinda odd too because she knows that I am approving and encouraging of her having a boyfriend/bull/buddy if she wants one.

I’ve been lucky so far and managed to keep my stuff hidden and not get caught being fully dressed out. Sooner or later your luck runs out on you though, my time is probably coming. At that point, I’ll have to disclose the entire truth to her, well most of it, there’s a few parts there that I guess I don’t actually have to say if/when that time comes.
 
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That’s a very good question, I’d have to say she’d be way more upset to find out I was screwing around behind her back. And that’s kinda odd too because she knows that I am approving and encouraging of her having a boyfriend/bull/buddy if she wants one.

I’ve been lucky so far and managed to keep my stuff hidden and not get caught being fully dressed out. Sooner or later your luck runs out on you though, my time is probably coming. At that point, I’ll have to disclose the entire truth to her, well most of it, there’s a few parts there that I guess I don’t actually have to say if/when that time comes.
How is she to the Idea of her having a man on the side and cuckolding you? Maybe that would help her warm up to your crossdressing a little bit. Cuckolds often get feminized.
 
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How is she to the Idea of her having a man on the side and cuckolding you? Maybe that would help her warm up to your crossdressing a little bit. Cuckolds often get feminized.
Well, while separated she had a boyfriend and when she came home we’d agreed she’d keep seeing him. That fell through. She started seeing someone else behind my back, when she came back home from that again we talked and agreed they could keep fucking but that ended too. Now she says she’s not interested in it at all, so I tread lightly on that subject with her. I’ve asked about wearing a cage… no interest and it’s “weird”. Right now her switch is just off obviously and I’ll have to wait until it comes on again I guess.
 
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I loved wearing my wife’s stuff too, made me feel closer to her, especially during the long dry spells. But… foolishly I took a few pics of myself in some of her stuff and she found them. That was very bad, it’s never been forgotten or faded it seems. SO, with that said, get her permission before you take her stuff and wear it or get your own. That can be a slippery slope if she finds “your” stuff because then she’s gonna think it’s another woman’s stuff.

I started out wearing my mom’s stuff and many years later when I came out to her about “me”, she was actually very understanding and supportive of it. She said she didn’t mind at all and even brought me some of the things that I told her I loved wearing of hers, I still have them today.
Sweet
 
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