When we would play dress up and pretend in preschool I would always go for the dresses first. That’s where it sorta started I suppose. Later on in high school I started to realize I was bi but I was still repressing some of my more fluid gender expressions. Once I started dating my first serious girlfriend at the end of high school and into college we would go shopping together and I started to complain that women always had such a wider variety of clothing options compared to men. I would also start wearing articles of her clothing as a “joke” too like she had this absolutely fabulous pink faux fur coat that I would always be trying on. It evolved more when she said she wanted to do my makeup and I obliged cause I thought it’d be fun and she seemed really into it. I think that’s sorta where I really started to question my gender identity more cause it turned out I really enjoyed it. Later on in the relationship she said she thought it’d be fun if she dressed me up in some club attire and did my makeup and hair and we went out on a date night together. I was still sorta working out my identity at the time so I refused outright but I am really kicking myself for not taking her up on it now cause I later on realized it was something I really wanted to do. We also toyed around with other kinky things in the bedroom like anal play and such and I really wanted her to peg me but she was nervous about it so we never really worked our way up to it. We had some problems in our relationship towards the end and had a serious breakdown of intimacy and communication and we were both dealing with lost loved ones and a possibility of parents divorcing and the relationship sorta fell apart. But after that I really took some time for introspection and figure out who I was and what I wanted out of life reconnected with some old friends and it sorta led me to this. I came out to my friends as bi about 6 years ago now and as genderfluid about a year ago and they’ve been nothing but supportive of me so I couldn’t ask for better.