With My Best Friend’s Sister…



What’s your gender? Man
How old are you? 24
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Businessman
What’s your current relationship status? Dating casually
Religious affiliation: Shinto
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? none

With My Best Friend’s Sister…

How long ago did this hookup happen? 1 year ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For 1 to 3 years

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? Light brown hair, tanned body, slim but a fit body (tight abs for a girl), 36D breasts, long smooth legs (All in all a GREAT bikini body). She was wearing a white cutoff tank top, red button-down tied up at the waist, and denim hot pants and boots.

She is my best friend’s younger sister and we’ve talked a couple of times prior to the hookup.

I always thought she was one of the sexiest woman around and I was a little nervous at first when I met her at a party. She noticed me drinking and having fun and we started talking.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were hanging out in the backyard by the pool talking about each others lives and what we have been up to (haven’t met her since my high school graduation; only texted each other since then) and there she mentioned to me how she had feelings for me back in high school.

Since she got sick of all the people at the party and I lived close by to the house, I invited her over to my apartment. I wasn’t planning on taking it further than just hanging out, but the way she dressed and the way she cuddled up against me hinted the fact that she wanted a hookup.
After getting to my apartment we were watching videos on YouTube with the lights a little dimmed until she cuddled in close and started kissing my neck.

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? She told me about how she wanted to have sex with me and how badly she wanted it.
She instantly unzipped my pants and without knowing that I have a thing for girls with a nice fit stomach, she started giving me a lap dance and rubbing her breasts against my face. As my cock started getting raging hard, she went on to give me one of the best blowjobs ever and it was so hot and sexy watching this petite, sexy Asian girl go down on my cock.

After a while, she begged me to take her to the bed room so I lifted her up and took her to my bedroom where she took her pants off to show me her shaved pussy. I started to finger her while reaching for the bedside table to grab the condoms. She was wet and after a few thrusts she was begging me to put it in.
I couldn’t help but glance at her perfect body as I penetrated her and she start to curl and moan… she showed off her abs when she was on top and every time I was penetrating her with missionary she asked for harder and harder to the point where the bed was creaking and the bed was banging on the wall. We ended up trying missionary, cowgirl, doggy, standup doggy, and anal (she was begging for it) and the more sweaty we got, the more I got aroused. Ended up cumming in the condom and she drank the semen out of the condom and cleaned my cum covered cock thoroughly.

We ended up having sex one more time that night and twice in the morning before she had to leave for school.

She was hands down one of the best sex I had ever had.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Although I felt a little sense of guilt towards my best friend, I could only see her as a super sexually active sexy woman.
We became fuck-buddys and would meet and spend every weekends together.

Honestly we still text each other and occasionally “hookup.”

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Just happened, I don’t know why, just went along with it

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Got to hookup with my dream girl

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

What do you think about the Casual Sex Project? I think this is great place to share experiences

You have a hookup story to share? Submit it here!