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I (m 22) have been taking some odd jobs since i graduated college while i look for a real job. This summer one of those jobs was being a pool cleaner. I live near a very affluent neighborhood and there are lots of people will to pay decent money to have their pools cleaned.
This particular day, I was cleaning the pool of this house and the wife (f 35 ish) was at home, and had over a couple of her friends there to chill. She was quite attractive and I decided to be a little flirty.
We got to chatting as i finished cleaning and I told them that they should go for a swim. They did not seem interested, but one of them suggested i dive in first.
I told them that I have a pretty good dive, and they they should take notes. So i go changed to my trunks and they took our their phones to record my dive. I jumped, and i seemed to have a lot more speed that usual, so tried to correct it mid air.
Dove in and things felt good, but thats when i realized that my trunks and slipped off all they way to my ankles!
I quickly tried to pull them back up and the women there were laughing. Safe to say i wanted to world to just end there.
I quickly got up and got changed. Not sure how had of a fuck up this is but thought i would share. I keep telling myself that they are older and thus will not gossip too much about such things.
TL;DR - tried to show off to some older women and ended up having my shorts come off as i dove into a pool
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