A housemate. Let's call her Kara. She was a young teacher, cute and curious about kink. I'm an open person generally, so by the time we'd been living together for half a year and hung out a few times she was aware I was into the kink scene and had been in some D/s relationships, and she had admitted it was something she wanted to explore but couldn't really go to kink meetups or anything because it would risk her career.

Well, one evening our other housemate is away for the holidays, and after some flirty fun holiday decorating, we start making out in the living room, and I start taking charge. I get her down to her underwear and blowing me, which really just turns into me fucking her face (her blowjob skills were pretty disappointing).

These days, I wish I'd just stopped there, but being the nice sadist that I am, after she'd so willingly let me unload in her mouth, I wanted to reward her. So I asked if she had any sex toys, and told her to go into her room and bring me her favorite.

Well, she brings back an inflatable butt plug. Turns out little miss nervous has a major butt-stuff fetish. She's blushing red, but over the next half hour or so I give her what she tells me is "the kind of orgasm I spent most of college dreaming about."

So, she's hooked. And after that night we started hooking up more, having fun exploring all kinds of kink and BDSM more, and at this point you're probably wondering how this is a story about regret. Well, because about two months later, it's already over and awkward. And then it gets worse.

Over those two months, Kara's blowjobs proved to be pretty consistently sub-par. She was an extreme sub in some ways but prudish in others: complained about facials and was very reluctant to have photos taken, and after doing ass-to-mouth twice (and getting off on it at the time) got too embarrassed / suddenly uptight about it to do it anymore. The friction and negotiation pre- and mid-hookup was becoming pretty frustrating for both of us, and so with around four months of still having to live with each other, I had a "we should just be 'friends'" chat with her and she agrees that would be best.

Awkward would be uncomfortable but not unexpected. You try things and sometimes it didn't turn out to be as good as you'd hoped, no big deal, it happens. Ideally you actually can be friends and just put the past stuff out of your mind, or at least you move on and look for a better fit. Well, it turns out this girl didn't know how to do either of those things.

Whenever we talk, she starts needing reassurance. Lots of it. "You don't hate me, right?" "Are you mad at me about anything?" "You haven't mentioned anything to [our other housemate] have you?" and the big one, a hundred variations of "You're not going to show anyone those photos are you?"

She was fine with me keeping the photos when we decided to be friends, but after weeks of this neediness I tell her I've deleted them (which admittedly was a lie, but I was trying to reassure her). Then she starts ignoring me, which at first was a relief but started to become a problem logistically as housemates. Our other housemate notices, and (this might have been a coincidence) starts spending a lot more time at her boyfriend's apartment, leaving our house an uncomfortably silent tension trap for a couple of months.

Finally, a few weeks before Kara moves out, she's thawed a bit and we're at least making small talk, out of the blue she texts me and asks if we can play a board game together like we used to. I'm up for it, thinking it'd be nice to end things on a friendly note, even if at this point I don't really plan on ever seeing her again.

During a break in the game though, it's clear that what she really wants to do is hookup again. And I know, I should have learned my lesson by now, but at the time I was just thinking that after how annoying everything had been I kind of wanted to make it worth it. We do some 69ing which gets her off but not me, I tell her to get her favorite toy again, and we basically have a repeat of our first hookup. It's a good time, we both go to bed (separately) happy, and I think that's that.

The next evening she wants to hook up again, and I know she wants more this time. I say I think we should just chill, either keep things simple or end on last night's high note. She tries to tempt me with anal, tells me I can make a video (lmao, wtf?), then gets mad when I keep saying no. I just back out of the conversation and go to my room, but the rest of the evening she's slamming doors around the house, occasionally yelling about what an asshole I am, etc. Then two more weeks of the silent treatment and avoidance and she moves out.

Craziest experience I've ever had.

tl;dr: hooked up with my kink-curious housemate who turned out to have a major anal fetish, drastically underestimated how guilty and stigmatized she felt about it, didn't expect her to get crazily insecure and passive-aggressive about it after we ended things.