The Vainest Sex Ever

by Francesca

Gender: Female
Age: 25
Race/ethnicity: Caucasian
Location: San Francisco
Highest education received: College degree (eg., BA, BS)
Relationship status: Single
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 27

The Vainest Sex Ever

How long ago did this hookup happen? last year

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…)? Friends With Benefits

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? Christian (not his real name) is GORGEOUS, but insecure. Without a doubt, he is one of the best dressed men I’ve ever banged. I knew Christian through friends – he was actually the roommate of a close comrade of mine. Before we hooked up, I liked Christian a lot as a friend. My friend (Christian’s roommate) was notorious for ditching the group, and Christian used to keep me company whenever this happened.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Christian (allegedly) put the moves on me three times before anything happened. Eventually I came around, and invited him to a pro game. My plan was to nail him that night – win or lose. Our team won, so we made out and went back to his place.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during 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? How did it end? Christian and I hooked up for months. The only time we ever did oral was me on him to get him hard (not like that was difficult). I felt AWESOME during it. I orgasmed ALL THE TIME. 

Christian was sweet to me. During sex, we kept saying “you’re so fucking hot” to each other repeatedly. Sometimes, we’d switch it up and scream “you’re so fucking sexy.” Regardless, there was always a “you’re so fucking [adjective flattering one’s aesthetics]!” 

It ended because it was getting uncomfortable. Christian was extremely passive and asked me where it was “going,” but had no answer himself. I ended it because I was sick of the conversation.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We were extremely negligent in this area, and (although I had a great time), I regret it. The only time we used condoms was when I was on my period.

What were your REASONS for having this hookup? Honestly, I was dating a (slightly) older man who never had time for me. With no parameters of exclusivity were set, I sought Christian to keep me company when the other man couldn’t. 

Eventually, it was about more than that. I really do care for Christian.

Were alcohol or drugs involved? If so, how much? Sometimes we’d be drunk, but not always.

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 wouldn’t date him, but I had hoped we could be friends. It’s not looking like that will happen.

To whom did you talk about the hookup? How did they react? Everyone knew. No one cared.

Was this a consensual and/or wanted experience for you? For your partner? Yes and yes!

Do you regret this hookup? If so, why? NO!

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? Christian was AMAZING in bed, and very respectful. To this day, he is the only man I’ve fucked who has explicitly said, “I don’t think your period is gross, and you shouldn’t feel ashamed to have sex with me while you’re on it. If you do, I won’t force you to think differently, but understand that I still want you.” 

Which probably speaks volumes about the terrible men I date …

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

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