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The perks of being a tomboy

Posted: Sat Mar 19, 2022 4:41 am
by stripic
I was always a tomboy and was frequently mistaken for a boy when I was younger. So it wasn't super uncommon for me to witness pantsings, flashings, moonings, or other embarrassing things boys don't usually do in front of girls. One that really stood out was at my high school crush's graduation party. We were good friends who kind of had a flirty thing going, but I think we were both afraid to take the next step. I had never been to his house before, and I didn't know he had a pool, so when I got there everyone was swimming and I was fully dressed playing on my phone. Because I went to the all girl's school, and just knew my crush from a camp we were both at - I didn't know a lot of the people at the party - and at least some of them clearly thought I was a guy.

Anyways at one point my crush got out of the water and started walking over to me and say hi. When he was a few feet away, one of his friends giggling like an idiot, pulled his swim trunks down to his ankles. I still remember the look of horror on my crush's face as he realized I was seeing him completely nude. Of course I also remember the sight of his penis, which was not exactly at peak performance having just been in the cold water. I knew I was blushing bright red because I could feel my face get hot, and I knew I should look away but I couldn't! Instead my crush turned around and bent over to pick up his shorts, giving me a full view of his ass. For the rest of the night things were awkward between us, but a few nights later he showed me his dick at full size. I was mesmerized, but too naive to do anything with it.

I had a lot of these kinds of experiences - and I’ll probably add more soon.

Re: The perks of being a tomboy

Posted: Thu Mar 24, 2022 6:58 pm
by Redfaced90!
I look forward to hearing about your other experiences!

Re: The perks of being a tomboy

Posted: Fri Apr 01, 2022 9:37 pm
by ely
I had a lot of these kinds of experiences - and I’ll probably add more soon.
As I read I hoped they would humiliate you but in a light and not too disturbing way. I was disappointed that the boy was the victim instead, but I'm happy for you that you saw his butt XD

I hope that it is not a phrase of circumstance but that one day you will put some story, digging into your memories surely you will find something ...

ps: I love the term tomboy and the stories about them.