I dated a girl for most of 2011 who was, if not quite "anything goes," surprisingly "more than you'd expect goes" when it came to showing skin in front of her parents. She was 21, black, looked not particularly unlike a young Lupita Nyongo except with a big almost 70s-style afro and rather bigger tits. Quite possibly the hottest girl I've ever dated or had sex with, and 100% without a doubt the hottest girl I've had sex with more than once. (Not that I'd ever tell my now-wife that!)
Anyway, her parents were divorced but on pretty good terms with each other and very good terms with her and both lived in town and visited a lot. Her mother in particular she was very, very close to, her mom lived literally a five minute walk from her apartment and would drop in all the time. To be honest, annoyingly much, I sometimes felt like I was dating her and her family and that may be part of why we eventually broke up - but that's neither here nor there.
She would, to my complete lack of any complaints whatsoever, pretty often hang around her apartment when we were together in her underwear, naked, or in just panties, especially in the summer. (Just to set the scene, it was a VERY small apartment very much intended for nothing more than a college student to live in for a year or two - literally the entire apartment except the bathroom was one not-especially-big room, bedroom/living room/kitchen all in one, you could see every inch of the place except the bathroom from the front door.)
Cutting to the chase: She had the initially pretty shocking habit of, when one of her parents knocked on the door when she was hanging out undressed, answering it showing a bizarre amount of naked skin for a 21-year-old woman in front of her parents. First time it happened we had been dating a few months, it was summer, and it was pretty mild - she answered the door and talked to her mom for a minute while wearing a t-shirt and panties (with me right there on the couch, her mom waved and said hi to me and everything). This was not acknowledged in any way by her or her mom.
Not much later she did the same thing again with her mom this time in nothing but a bra and panties, again a quick conversation and me right there and neither of them mentioning it in any way. Then one time when her dad stopped by, this time with a half-closed kimono-style robe very lazily wrapped around herself, not technically showing again but very obviously naked underneath to anyone, once again with me right there and it going unmentioned. Then again with her and her mom in bra and panties as she put on clothes before they left somewhere together, her and her dad wearing gym shorts and a bra, multiple times with both in a tank top and panties, etc. This happened like maybe twice a week at this point (her mom, as I mentioned, literally stopped by at some point almost every single day). I won't go into all the incidents because they soon numbered in the dozens, especially with her mom.
Though I never actually mentioned it to her in any way (why interfere with a good thing?), I quickly hashed out the "rules" as it were: She would only open the door this way if it was going to be a quick conversation or something, if she knew they were coming or she thought they were going to actually hang out for a while or they were going somewhere she would be properly dressed when opening. For her mom, a top (t-shirt, tank top, etc) and panties, a bottom (sweatpants, shorts, etc) and a bra, a bra and panties, or a barely-closed robe were all fair game, same for her dad except bra and panties.
There were three exceptions to these rules that occurred during the time we were together:
1. One time her mom left her dog with us to dog-sit while going out of town for the day. When she returned that night very late and knocked, around midnight, my girlfriend took the dog to the door (I watched this from bed) wearing nothing but panties and opened the door while doing a sort of V-shape with one of her arms over her nipples. As the dog was passed over they had a quick exchange (Basically "How was your trip?" "Here's the dog" "Goodnight, see you tomorrow", etc). The door was open for thirty seconds at most and my girlfriend as far as I could see kept her nipples covered, but she FULLY opened the door, not peeking out from behind it, and I was visibly right there in bed too, pretending to be asleep but watching.
2. Exactly one time she answered the door for her dad wearing a bra and panties. I'm not sure why, but this one time she did (all other times if her dad knocked when she was in bra and panties she would put on a top). The three of us were going to dinner and she let him in and made chit-chat with him while walking over to the dresser and getting clothes and putting them on - with me right there, as usual.
3. Probably the strangest incident of all (and one I have to admit I still jack off to sometimes) - she had just gotten a brand new kitten and she and I were playing with it, her in bra and panties, when suddenly her mom knocked, wanting to see the kitten. I threw on a shirt and gym shorts but by the time I had looked over she had gone and let her mom in. By itself this wasn't too weird, except that her and her mom walked over and started playing with the kitten without my girlfriend putting anything else on! All other times she had only opened the door for a minute before either her mom left or she got dressed. But this time, by god, her and her mom sat there and played with that kitten, held it, petted it, played with toys with it, with my girlfriend in nothing but her bra and panties for over 20 minutes. Let me tell you: Fully-clothed you, your girlfriend's fully clothed mom, and your bra-and-panties girlfriend hanging out alone in an apartment for 20 minutes is incredibly fucking weird and awkward but also weirdly hot. I thought about it that night fucking her and blew one of the biggest loads of my damn life.
Anyway, we eventually broke up and I haven't talked to her in over a year at this point, she's actually moved and lives in another city entirely now. But I'll always remember my ex-girlfriend who was the most casual I've ever seen a grown woman be about her parents seeing her in her underwear all the time.
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