Uncle's Ex-GF
This story is the 100% unembellished truth - perhaps made evident by the fact that it does not end with me getting laid (though in hindsight it possibly could have), but it's about the sexiest not-sex thing that ever happened to me.
When I was 20 I moved to a new city and rented a room from a friend of my (youngish) uncle's in his old neighbourhood. His ex, who he'd lived with for several years and who I knew of but never met still lived in the neighbourhood - we became friends and hung out a bit and smoked pot - she was in her early-mid-30s and attractive but not overly sexy - she had a good body but dressed quite modestly and never really showed it off - lucky to see her in a knee-length skirt. One particularly hot and humid day I went over to her place and was rolling a joint and she walked in front of her window in front of me and I realized that the flowy dress she was wearing was VERY see through in the light. It took me a second to realize what I was seeing but it was like, whoa, I can just totally see her panties right now, sweet! Coming from a girl who'd shown nothing before, it was pretty hot. It wasn't until she sat on the window seat and we were smoking the joint that I realized she wasn't wearing a bra and I was getting a full, barely obstructed view of her cute little tits and large, erect nipples - she almost might as well not have been wearing the dress. It was going to be a good day. After an hour or so of trying not to get caught ogling, another neighbourhood regular - an older guy - stopped by on his work break and after a few minutes said, "Um, do you realize that dress is like completely see through right now?" SHUT THE HELL UP, I thought, but she said, "It's so hot out I don't even care." It was pretty fucking sexy thinking she was unaware of what she was showing, but somehow even sexier knowing she knew but didn't care. And I think she knew I was loving it too because at one point she said, "You should go get us some ice coffees - I'd go too, but then I guess I'd have to change..." NO PROBLEM, I said. Throughout the rest of the afternoon she even provided a couple nice upskirts (white panties - my favourite) and then a full nipple exposing downblouse - almost unnecessarily generous at that point but I wasn't complaining. Again, maybe she was coming on to me and I should have went for it but it made for a glorious jerk-off later on and every once in awhile in the years since.
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