"I will be your next woman"

You decide to provoke him: “Ah, do you like women? And then I will be your next woman"

He replies immediately: "Are you serious? Do you like dressing up? "

You would like to continue to provoke him, but he seems to be a serious guy and you don't want to make fun of him: "No, I never tried"

He: “Why don't you try? I've never been with a crossdresser, but the idea could be interesting. We can try, if we like it ok... if we don't like we will be friends as before”

You: "I don't know, I never thought about it ... I think I would be very embarrassed in women's clothes"

He: “And I will be embarrassed because it will be my first time with a person with a penis. LOL! Come on, I think you'd be fine with some nice women's underwear. Then if you don't like it, we'll have a laugh and there will be no problem"

You: "We can try ... but I don't promise anything!"

He: "Perfect, honey! Do you have any women's clothes? I have something left by my ex-girlfriend here, but they are quite ugly things ..."