Contributor: VeryBadBoyCD VeryBadBoyCD
Ever been caught Crossdressing
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Contributor: assman1953 assman1953
Oh yeah! I had donned my thigh highs, cami and thong panties to wear while playing with my dildo collection and making some videos of my play to post (elsewhere of course) while my gf was away. While I was about to record myself, she came home early and caught me in full crossdress and with my EF's Girthy Giant out (but not in me, LOL). Once she got over her shock and stopped crying, I confessed that I am bi, had been with men as a bottom and love self-penetration while wearing women's lingerie. Once I convinced her that I was now just in to solo play and no longer interested being with dudes (which was a lie, of course), she said (to my own shock) that she accepted my having been bi in the past but I had to promise (and she actually believed) that I would not crossdress or play with my dildos anymore. (Had she seen my extensive dildo or thong and panty collections she might have thought twice about believing my promise.) Needless to say, I break that promise whenever she's away long enough for me to do so, LOL.

I do so love wearing women's lingerie occassionally when I play anally that it's worth the risk of her catching me in it again-I'd tell her that I was sorry, but it was the only time since the time she caught me, really!

I'd consider wearing other items of women's clothing if a guy I was with wanted me to but, as they aren't necessary for analpay, my gf would never catch me in them (she'd probably have a heart attack if she did-but I'm certain she'd forgive me again if she survived, LOL).