By Confused in LA

Gender: Male
Age: 31
Race/ethnicity: White
Location: Los Angeles
Highest education received: College degree (eg., BA, BS)
Sexual orientation: Hetero
Number of prior hookup stories posted here: 0

Hotel Cafe Nights

How long ago did this hookup happen: 1 year ago

How would you best classify this hookup: One-night only

Tell us about your PARTNER(S). How well did you know them? How/Where did you meet them? How did you feel about them before the hookup? How many times had you hooked up with them?: I met this girl online via OkCupid.  She and I both attended the same Ivy League University, so I knew she was smart and also attractive.  I asked her out on a date and wound up taking her home that evening.

How did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Where did it take place? Were alcohol or drugs involved? If so, how much? We met up at a very cool music venue/bar in Hollywood called Hotel Cafe.  We talked a bit, but conversation did not flow easily.  When I finished saying something, she would just get this pensive, deep in thought look but then not say anything.  I am not the most gregarious person, so I feel like the mix of our two personalities compounded the problem.  Also, although I offered her drinks and she got a glass of wine, she didn’t have more than a sip – mentioning a missing enzyme that makes her alcohol intolerant.  I felt things were off to a fairly poor start, except that she mentioned that her first serious boyfriend was a computer programmer and she has a sort of computer programmer fetish (my occupation).  She also mentioned how she has exhibitionist tendencies and while staying in hotels (something she did often for work) she liked to undress in front of windows not knowing who might be watching.

What were your REASONS for having this hookup? I thought she was attractive, smart, but also mysterious – I couldn’t get a good read on her.  The sexually charged conversation prompted me to invite her back to my place, and she agreed.

Was this a consensual and/or wanted experience? Yes, sort of.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How much did you enjoy it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? How did it end? I bring her to the bedroom and she asks if I have a T-shirt she can borrow, which I provide, and she goes to use the bathroom.  She comes back wearing just the T-shirt and panties, we settle down, and I make some moves expecting to get laid.  She is deflecting every advance, which is confusing, because why did she come home with me? I can’t figure out the mixed signals, so I eventually just give up and go to sleep, disappointed.

Morning comes, and I try again.  Again, she deflects, but then the weirdest thing happens.  She tells me that she is super horny, and wants to get off with a vibrator – which she has brought with her in her handbag!  She doesn’t want me to touch or talk to her though, because she requires concentration.  “Okay,” I said, and she gets to work.  A few minutes later, she gets herself off sporting a nice moaning O-face.

I asked her what she was thinking about while vibrating herself, and she tells me of this fantasy world she has made up that is an all girl’s school.  The girls live at this isolated school, wear their sexy little outfits, and part of their everyday lives is that they get groped and molested by the teachers.  She said they just accept it because they don’t know any other life.  For them, it is normal.

I swear to god, I am not making this up.

So now I am more confused because she deflected my touches, but then told me her fantasy where school girls are getting groped and molested.  I asked her if she considered herself one of the school girls in her fantasy, but she said “no,” that she wasn’t really there, it was more just the idea.  Meanwhile, I am wondering if she wants me to be more forceful, and continue my advances despite her deflections, but that is a risk I was not going to take.  I felt like Louis C.K. in his bit:

So a few minutes later, as I’m still trying to get some kind of read, she brings my hand down to her panties, and has me push the crotch of her panties up inside of her.  She tells me to push “really, really hard,” so I do, and she gets off again.  Once again, however, she stops me when I try to use my fingers without the panty barrier.

My balls are pretty blue at this point, so frustrated, I’m just like, “okay, I’m gonna take care of myself now too.” She says “okay,” and rolls over.  So I’m there in my bed, jacking off, with this strange girl resting next to me.  As I’m about to come, she sits up abruptly and rips off the T-shirt to show me her breasts.

What happened AFTER the hookup? How did you feel? What happened (if anything) with the person? How do you feel about this person now? What are your expectations/hopes for the future with this person? Do you regret this hookup? If so, why? Satisfied through my own efforts, I fall asleep again for another hour or so.  I do the honorable thing and take her to brunch before she leaves.  It was too weird, and we have too much of a normal communication problem for any kind of 2nd “date,” but it was certainly interesting…

To whom did you talk about the hookup? How did they react? I told the story to some of my friends who all found it entertaining.  Most of them are in committed relationships.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This hookup left me more confused than anything else.  Sexually, it was not very satisfying.  But it was an interesting enough experience, that I would not take it back.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? I chose this particular casual hookup story because it was a strange one for me.  I think most of my other casual hookups and relationships are more “normal,” whatever that means.

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