by Jenn

Gender: Female
Age: 26
Race/ethnicity: White
Current location: San Francisco
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Student
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly gay/lesbian
Any other term(s) that describe your sexual orientation/sexuality better/best? Prefer women but enjoy giving oral to cute men
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 0

Best Friend’s Sister

How long ago did this hookup happen? Seven months ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Dee (not real name) is average height, slim, has a cool pixie cute, upturned nose, slim legs to die for and nice boobs.  Pretty face. Blue eyes. Very very exciting. Never had done anything with her before.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Always had a crush on my straight best friend.  She knows I like girls but always made it clear she had no interest.  But we have been close. Her younger sister is very attractive and I began to notice her a couple of summers ago when I came home for summer break and visited my BF.  I am very sexual and Dee, the sister was a huge turn-on, enough to make me very uncomfortable.  One night last summer I realized I was coming on to her but my gaydar was telling me she was interested. We started talking and she told me she had made out with a girl before, so we talked about that and she confessed to a crush on me.  I told her I was very attracted to her but that she was young (not quite 18). Later on after I left she texted me and dared me to date her just once. I texted back for her to meet me at the mall the next night (Sat) at 7.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We walked downtown and then got into my car in a parking garage, talked more and started to make out. Very good kisser. She wasn’t wearing a bra and I caressed her under her blouse. It got ridiculous in the front seat so we moved to the back. She was wearing a skirt and I fingered her while I was kissing her and pretty much came right away which I didn’t expect.  She rubbed me through my jeans but I didn’t come. I went home frustrated. But she was happy and told me she wanted me in a bed with her sometime.

Did you have an orgasm? Did your partner(s)? No, I didn’t.  She did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No, none of that.

What were your REASONS for having this hookup? She is really hot and wanted it, and I am into girls.

Were alcohol or drugs involved? If so, how much? No.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I saw her several times during the summer.  Yes, we ended up in bed, and yes, I certainly came with her. She LOVED me going down on her and she was decent at giving me oral.  I had zero long term romantic interest…this was sex, for me, pure and simple.  Dee did have a crush though, and she bugged me a lot when I returned to school, so I broke it off last winter.  I still think about her body though.

To whom did you talk about the hookup? How did they react? Nobody.

Was this a consensual and/or wanted experience for you? For your partner? Consensual.

Do you regret this hookup? If so, why? No, it was fun.  If my Best Friend had learned of it it would have been bad, though.

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? Great kissing, feel of her body, her coming the first time and the sounds she made.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? I was the first girl she had had but it wasn’t a bicurious thing with her…not just experimentation. She’s authentically bi at very least.

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