I was living in the dorms at my college. We had 4 room houses with guys in one house and girls in the next. I became really good friends with one of the girls next door and we started dating. We would talk for hours and hours about anything and everything. I admitted to her that growing up I would steal my older sister's panties and wear them. It was like my biggest, darkest secret lol. She naturally thought that was funny, but immediately wanted me to wear hers too. It became a turn on for both of us for me to wear her panties and lingerie, and she even ended up buying me some stuff of my own. We would spend many nights in our lingerie in her room drinking wine and enjoying each other. She even wanted me to let her put makeup on me, and do the full crossdress thing. It was always humiliating but exciting to be feminized like that by my gf, especially with her roomates in the house. One night after too much wine she told me she wanted to see me with a man. I will admit I was curious, but I was too afraid to tell her that. She kept talking about all the things she wanted to see me do with "him" and how she knew I would love it. I told her it sounded like she had the guy picked out already. She said that she did, and it was a brother of one of her roomates. She explained he was cute, shy, and gay but had never had a bf and she wanted to dress me up and send me on a date with him before we came back to her place at the end of the night. She had obviously been planning a lot of this for a while. The next couple weeks she talked about it a lot, and wanted me to get dressed up every day for her. Eventually she wore me down and I did go on a date with him, and I did end up having sex with both of them on multiple occasions. To this day he is the only man I have had sex with, and I haven't been brave enough to admit this side of my sexual past to anyone. I am now happily married, but I wish I would have told her about all this.