I had one ex that was very supportive when she found out. She kinda pushed me to do more and more, little by little. Even though she had never seen me dressed, so she was seeing things for the first time as they were progressing. But she was kind of excited at the prospect of having a girlfriend and boyfriend in one (We’re both bisexual). So it started out with her having me just wear panties instead of boxers when we were going to the store, or out to eat. Then it moved up to bra and panties under my mens clothes. And she made sure I had the right size. And that I knew how to measure for the future. After a few times of doing that, she had me still wearing a bra and panties, but added a basic black v neck women’s top. Although I had a hoodie on over it, so no one but us really knew. Even that made me extremely nervous. Then she would have me take the hoodie off while we were driving, which was terrifying. For pretty much that entire fall/winter I was 1/2 dressed all the time while we were out. Just mens jeans over my panties, and a hoodie over my bra and women’s top. Eventually she would start to have me wear a full outfit while we were just driving around, but we didn’t ever get out of the car. Tight boot cut jeans, skirts, or short shorts with a cute top. Sometimes dresses. Then we would start to add jewelry to the outfits. Eventually we added make up, and she would do my hair. (I’ve had long hair since around 12 year old). Then she encouraged me to bring my purse with me everywhere I go dressed or not, which I still do. But just leave it in the car when I go in places, which a lot of women do. After some time of just being at home together or driving around with me fully done up. She decided it was time to take the next step. She had me get all dressed up, and pack a bag for a few days. But to only pack like a woman, don’t bring anything manly. We got in the car and drove to a city in the next state over. When we got to the hotel, she went in alone to get the room. But then, walking through the lobby and to the room was my first time really getting out and walking in public as Kristen. Throughout the weekend we started with short in and out kinda trips. But each time we went out, it was for longer and longer. The first trip was basically to just stand in the parking long enough to smoke a cigarette. Then then next trip we walked around the block, still just long enough to smoke a cigarette before we were back at the hotel. But then it was two blocks. And each trip we were out longer and longer. The first night we ordered delivery food. She had me go to the door with her, but she did all the talking. That was the first time I ever got somewhat close to anyone other than her while dressed. Later that night we had to go to the store to get cigarettes. She had me go in the store with her, but again she did all the talking. It just built up more and more. Until on the last night we were out all night. I didn’t ever talk to anyone but her. When we went to eat or get drinks, she would order for me. We did trips like that a couple more times before we split up. But we still talk. And she steals my make up. To be honest though. I haven’t really gone out like that since we split. The only time I really leave my house dressed is when I’m going to hook up with a guy. I’ll drive to the guys house dressed, go in and hang out, have sex, then go directly back home. I’ve had a couple girl friends that knew, but I never dressed for/with them. And I really haven’t gone and walked around anywhere.
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