Ever since you were a boy, you enjoyed dressing up as a girl. You don't know how it started, just that whenever your parents left you alone, you would play dressup in your mother's clothes, and makeup, but were careful to make sure they never found out.
Yet you have no real desire to actually transiton; for the most part you live your life as a normal man and let your femme persona come out every now and then. When you were in jr. high and learned about PMS and other things women go through, it actually made you very glad to be a guy. Nor are you gay; about the same time, you discovered how much you like to kiss girls and do-other-things with them.
As you got older and moved out on your own, you began to discretely build up a collection of women's clothes, acessories, cosmetics, and wigs, and gleaned information about how to make yourself passable as a woman. You even found out a support group of others like you. These fellow CD gals, as they call themselves, helped you a lot and gave valuable advice, and you even gained the courage to go out in public 'en femme' with them, although you still remained somewhat closeted.
Needless to say, your dating life has been, well, complicated. Most of the women you've dated you've kept this a secret from. One you did talk about it to screamed that you were a pervert and dumped you immediately. The second one tried to convince you that you are gay and in denial.
And then you met Monica.
You had been dating for the past six months, and finally, with the encouragement of your 'sisters' in the support group and their wives or girlfriends, you gained the courage to tell Monica about your crossdressing. Instead of acting negatively, she seemed intrigued. After showing her pictures of you as your femme persona, and your secret female wardrobe, she says she wants to spend an evening with you as a girl this weekend.
As the weekends nears, you look forward to the event, thinking of how it'll go. Thoughts race through your head of you and Monica going out to dinner or a play, her helping you get dolled up, of cuddling together or kissing with you both wearing lipstick. All of it makes you VERY horny.
Finally, you get such images out of your head. You are about to go through a big milestone in your relationship with Monica and you need to prepare so it will go perfectly.