The woman I came out to as a cross dresser.

I was on a temporary assignment and she had been assigned to get me settled, apartment, rental car that sort of thing. Boy did she. We soon discovered our mutual appreciation for anal sex, d**gs and alcohol. She moved in a week after I got there. But she had no idea that I kept a suitcase in the closet that contained my feminine wardrobe.
We were lying in bed, having a smoke and a gin and tonic and watching a foot ball game. The smoke got us aroused and I was enjoying foreplay when I thought I might encourage her to wear lingerie when we had sex.
"Do me a favor would you?"
"Of course, what is it?"
"Put on a pair of pantyhose. I love the feel of them, Its so sexy"
She got out of bed and went to the chest of drawers and put on her pantyhose.
She came back to bed and I was enjoying wrapping my legs around her nylon covered legs.
"Would you like to try on a pair?"
I thought my heart was going to leap out of my chest, a chance wear pantyhose with a partner wearing them! I tried to act nonchalant
with my response.
"Oh, I guess so."
She got up and provided me with a pair which I eagerly accepted and put on. I became instantly aroused and resumed foreplay, me kissing and sucking her breasts, rubbing her crotch, she rubbing my erect cock and exploring my prostrate.
"Mmm, you're right it does feel sexy when we rub together"
"I told you. I like the feel of a slip too, oh hell I like the look and feel of a woman in lingerie. Full slips, half slips with camisoles, those full body shapers all of it. I think it goes back to all those Sears catalogues."
"Is there any thing else you'd like to try on?"
My mind was racing, no one knew about Rachel my alter ego when I dressed. What if she blew my cover? Gossip at the home office would make me look a fool. On the other hand it would be a dream come true.
I lived my life on the edge. I drank every night, got high every night, I lived in a singles only apartment complex. Flight attendants got a 15% discount. Word got around the office and I found my self in my bosses office. He asking me about rumors of me being some kind of party a****l. "Hell Sir, if I had half as fun as people around here think I do, I couldn't make it to work most days. I think its because I'm single." "Yeah, that's what I thought, maybe you shouldn't joke about it." "Consider it done." Then the conversation turned to more pleasant things. Truth be told I was having twice the fun as the rumor mill was cranking out.
I made my decision. It was table stakes and I was going all in.
"Turn out the lights, I'll be right back."
I closed the sliding wood door between the bedroom and the short hallway that lead to the bath and the closet. I opened the suit case
and decided how I was going to come out. I chose white panties, matching bra and garter belt, white stockings a white half slip and matching camisole. I naturally choose the white high heels. I got dressed putting my breast prosthesis in my bra (38 D) and put it on, cutting a hole in the pantyhose so I could get to my cock.Then the garter belt and hose along with the panties and so on. I checked myself in the mirror, I admired my slim body, I looked damn good, with a wig and some make-up I could pass. Except for the mustache. I turned to the slider and peeked out to make the lights were still out.
"Okay now get under the covers and hid your head."
"Okay, I'm there"
I crossed the room to the bed, took off my shoes and joined her under the covers. We had just embraced when it happened. "Oh my god! I want to see! She rolled over and turned on the light on the night stand. Then rolled back and pulled down the covers "Oh my god! You look so cute all in white light a virgin! I love it."
"Well there is the mustache."
"Is there something you'd like me to put on?"
"Your Black bra (36C), black panties, black.." "Okay I get the picture you in white me in black. Kind of a bride and groom thing except a role reversal."
So I was out. We rushed to my temporary digs every night after work, got high, had some drinks and dressed up. We both wore dresses, did our housework, I did the cooking, we were just two Beaver Cleaver moms. Except I had a mustache and dick.
Eventually I had to return to my job in home office. It was some of the wildest sex I ever had.