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I like wearing Short Shorts
I'm a guy that grew up in the 60's and 70's. When it was warm weather I always wore shorts, and as anyone else who grew up during the same period, they were short, like most of your thighs were exposed, not down to or over the knees like it has been for the past 40 years or so. I still like wearing short shorts. I have some runner's shorts that I bought on Amazon, listed as "men's running shorts," that I wear all the time. I've been seen in them and have gotten some strange looks from people. I've seen the trend start to reverse in the past couple of years, so maybe people will quit thinking I'm weird for doing what was normal during my youth and early adulthood.
I wore my older sisters shorts forever. I was little and had great legs and loved showing them. I even shaved them. Mom never said anything. I sucked several ** because of it. After I got out of school I kept wearing womens shorts and shaving my legs. I even got brave enough to wear toenail polish sometimes with womens sandals. I got lots of ** in college.
I wear my gf's boy shorts outside and feel very naughty.
Does it ever hang fully out down the leg of your shorts?
I'm a guy and wear woman's shorts. Ladies undies too.
I was a teenager (boy) in the 1970s. My mom basically decided my clothes and for play she only bought short shorts and singlet tops and muscle shirts. I kind of miss it these days. Even when I finished high school and went to university, she'd put out short shorts for me to wear. Remember scoops. I had a pair of nylon scoops that were very tight on me that she'd make me wear to lectures at uni.
Mommy dressed you for uni?
Yes. I was quite an obedient and depent kid
My mom picked out my clothes too, all through High School (age 14 - 18 in the US) but not so much after I graduated. She usually had me in short shorts unless there was some reason shorts were not appropriate.