AlexBailey
Kinky Tomgirl
- Joined
- Sep 12, 2019
- Posts
- 11,424
(Thanks, Dawn!) 
One of my regrets from high school is turning down this one sweet girl who asked me if I was "spoken for." Lol, it sounded old fashioned 35 years ago too.
She was a cute and very boyish tomboy. I was platonic friends with her girly twin sister and got to know her peripherally through groups of friends. She was a grade behind me and had some social difficulties, often teased and ostracized by guys and girls, but I liked her as a friend and would hang out and invite her to go places with the gang.
I didn't notice - or maybe I just tried not to see it when she started developing a crush on me, until some other guy friends pointed it out. It was the first time I was teased for being more femme than a girl I was hanging out with. I was completely in the closet about my love for cross dressing at the time, but I had admired her willingness to present however she wanted to, even though people gave her shit about it - as I saw it, she was 100% authentic where I felt like a confused poser.
School dances were not usually taken very seriously, but some friends had set this one up with a retro dance contest theme. Our group all showed up en-mass rather than on dates so we were all free to hang out with whoever. My tomboy friend showed up all fancied up in a dress, with her hair and makeup done - it was an amazing difference, people were saying, "Who is that? No way!"
I wasn't planning to enter but she asked me to partner for the dance contests. We had a blast and really hit it off, making it to the final round coming in second, winning a dinner for two or something like that. It was later that night that she asked.
Her eyes were bright and her smile was warm and hopeful but I hadn't even considered being with her. I didn't feel it for her. I fumbled for words and said something like, "I'm not really looking for a girlfriend right now..."
Her smile vanished. She turned away and left the dance. I don't think she ever said more than a dozen words to me after that. Her style changed, she cut her hair short and went full butch for the rest of the school year. She had some troubles at home and moved away to live with relatives in another state. Her twin told me later that she had changed to a boy's name and had begun transitioning at a new school.
I know that it wasn't my responsibility in any way, but I have thought of her/him often over the years. So many choices. Adolescence is such a rough time, I really wish I could have been a closer friend and been available for them to confide in me at the time... the trouble was that I was a bit of a mess myself, but we might have connected better if we could have shared our feelings of dysphoria with each other.
I recently drove by my old high school and saw a pride banner sponsored by the campus LGBTQIA+ club. It's nice to think that these days kids like us have some support.

One of my regrets from high school is turning down this one sweet girl who asked me if I was "spoken for." Lol, it sounded old fashioned 35 years ago too.
She was a cute and very boyish tomboy. I was platonic friends with her girly twin sister and got to know her peripherally through groups of friends. She was a grade behind me and had some social difficulties, often teased and ostracized by guys and girls, but I liked her as a friend and would hang out and invite her to go places with the gang.
I didn't notice - or maybe I just tried not to see it when she started developing a crush on me, until some other guy friends pointed it out. It was the first time I was teased for being more femme than a girl I was hanging out with. I was completely in the closet about my love for cross dressing at the time, but I had admired her willingness to present however she wanted to, even though people gave her shit about it - as I saw it, she was 100% authentic where I felt like a confused poser.
School dances were not usually taken very seriously, but some friends had set this one up with a retro dance contest theme. Our group all showed up en-mass rather than on dates so we were all free to hang out with whoever. My tomboy friend showed up all fancied up in a dress, with her hair and makeup done - it was an amazing difference, people were saying, "Who is that? No way!"
I wasn't planning to enter but she asked me to partner for the dance contests. We had a blast and really hit it off, making it to the final round coming in second, winning a dinner for two or something like that. It was later that night that she asked.
Her eyes were bright and her smile was warm and hopeful but I hadn't even considered being with her. I didn't feel it for her. I fumbled for words and said something like, "I'm not really looking for a girlfriend right now..."
Her smile vanished. She turned away and left the dance. I don't think she ever said more than a dozen words to me after that. Her style changed, she cut her hair short and went full butch for the rest of the school year. She had some troubles at home and moved away to live with relatives in another state. Her twin told me later that she had changed to a boy's name and had begun transitioning at a new school.
I know that it wasn't my responsibility in any way, but I have thought of her/him often over the years. So many choices. Adolescence is such a rough time, I really wish I could have been a closer friend and been available for them to confide in me at the time... the trouble was that I was a bit of a mess myself, but we might have connected better if we could have shared our feelings of dysphoria with each other.
I recently drove by my old high school and saw a pride banner sponsored by the campus LGBTQIA+ club. It's nice to think that these days kids like us have some support.

