I am not posting this to fetishize the trans community. Read the whole post. Also. Bigots and transphobic people are not welcome here. I don't understand how you can be pro incest but anti lgbtq .

This is a very abridged story. This took place over 15 or so years. Again, I won't be getting too specific. This is anonymous but her story is her story. Also I want to remain anonymous.

All sexual acts mentioned are consenting 18 adults.

I have known my trans friend since the middle of high school. One of those people who was always around but I didn't become friends with them until later. Of course as a 40 year old we definitely became friends as kids but I knew her long before we were friends. We had a class together and became close. At this time he was presenting as a man.

We would hang out a lot. I don't want to associate cross dressing and wearing makeup with being a trans women. I know you can be a straight man who enjoys to cross dress. You can be a straight man who likes wearing lipstick and eyeliner. But when we hung out she would ask me about makeup. Kind of in a jokey way like, "what's this for." Or, "you do this shit every day?" Eventually it became her putting makeup on me. She was bad at it at first but genuinely became good on it. I jokingly offered to put makeup on her. I sensed that it was something she'd be into but I did it that way because I wanted her to be comfortable and like we were just having fun.

I don't want to sound all knowing. I didn't know she was trans. I just felt like she'd enjoy getting makeup done and the thought ended there. This was a WHILE after we had been hanging out and doing this. We started in middle high school and I was 18 and graduated when this happened so it was gradual. I put makeup on her and got her and she looked really pretty. She was always good looking. She always had really nice jawline and cheekbones. But makeup just suited her safe really well. We did end up kissing after this but it wasn't because I thought she was hot once she was femme presenting. This was a long buildup. For a long time we'd spend time together alone in the safety of one of our rooms doing this sort of thing. I'd put makeup on her and do her hair. She had really long hair and I'd style it. It was fairly intimate to have her against me while I ran my fingers through her hair.

She was attractive but the kiss we shared was more like a bonding kiss. We'd experimented with makeup on her before but this was the first full face and not doing it as a joke. Just doing it. I finished everything and when she looked in the mirror she was shocked. She looked so confident. Like she finally saw herself for the first time. To frame it properly she was sitting on my bed facing a mirror and I was standing by her. I said she looked beautiful and leaned down and kissed her on the forehead and then on the lips. It kind of messed up the makeup but she didn't mind. We just kissed and she said thank you.

Over the years this became a long journey. She would sometimes go out wearing lipstick and eyeliner and kind do it under the guise of being punk/goth. Then she'd go through periods where she presented as a man. Her family was and is still not supportive of it. She never labeled herself as being a woman. I never asked because it didn't matter what she identified as. She was and is just my friend. At the time she was my friend who wore makeup.

A couple of years after the kiss. I got her a dress as a gift. She had a closet of femme clothing. You could get away with a lot of it was under the punk/goth umbrella. I got her measurements and had the dress cut to make her shoulders look nice in them and it tighten just right around her stomach area. She was so confident. We went out together that night with some friends and she wore it. We kissed after and I went down on her in her car. She carried me up to her apartment and we had sex on her bed.

It was really emotional. We had been somewhat intimate before during makeout sessions. But I really felt like I was making love to a woman. Just the energy and the connection of your spirits. Before it felt like I was kissing my friend who went by a male name. But during this I felt like I was touching another woman. I was calling her "babygirl" the whole time.

She was inside of me. I took her virginity. I didn't know until after when she told me that she was a virgin. I just remember her talking about how tight I was. I mean I love getting told how tight I feel during sex but this was different. This was like when someone has their first experience with vagina and is shocked at how warm and wet it is and how good it feels. It wasn't like, "God baby, you're so tight." It was "whoa you're so tight whoaaa." I wrapped my legs around her and was thrusting my hips while she was on top. She fucked me in the dress and it just felt so right. It was an emotional experience just smearing her makeup and kissing while she was inside of me.

I think this is as far as I want to go with her story but it was a lot. She'd to from femme presenting to masculine. She'd cut off her hair and grow it back. It got bad when she had to move back in with her parents temporarily. I was genuinely concerned she'd do something stupid. But after 15 or so years. She eventually identified as a woman and she couldn't be happier.

Edit- apologies if I used any wrong pronouns. I was reciting from memory and during some times she was "he" to me.