My Straight Best Friend



What’s your gender? Woman
How old are you? 18
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Not graduated from high-school
What’s your occupation? Hourly
What’s your current relationship status? Single
Religious affiliation: Wiccan / Pagan
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Mostly into women
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

My Straight Best Friend

How long ago did this hookup happen? Multiple times over the last few months

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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? She was short only 5’0, beautiful long blonde hair, a thin but still thick 130 pounds, blue eyes. She’s my best friend for 6+ years. Three years ago we hooked up around my birthday, oral sex and fingering. I met them in elementary school. Before the hookup I had absolutely no feelings at all, the thought of my best friend disgusted me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Planning on my part was not involved, I had come down from my home 2 hours away to visit her, the plan was that I was going to spend the night, like normal.This was right after I had come out as bisexual. That night she wanted to try kissing, I went through with it. Later, we were both going to sleep when she put her leg over me, and i absentmindedly started stroking it. I then felt her twirling her finger around my nipple and we went on to have sex. Years pass before I make another trip, but we left on good terms. By now I’ve moved back into the same town she lives. I had a girlfriend so when she would grind on me I’d tell her to stop. In this last month we’ve slowly been climbing our way back up to our FWB status. It started with cuddling at sleepovers, she would flinch her leg muscles asking for me to give her my leg to grind on. I would ignore her telling myself “I’ll only pleasure her if she tries to pleasure me, she owes me one anyway.” Since I had orally pleasured her the last time and she had done nothing for me. A few weeks passed and I had not given in. It wasn’t until we were on my bed watching Netflix and I was playing with her hair (which is normal for us). I had my leg on hers but not between hers, she was laying on her stomach. I stopped playing with her hair. She then looks back at me while swinging her legs back and forth gesturing me to rub her with my leg. I comply mostly because her leg was close enough in between mine where I could get off as well, but also because she directly asked me to help her out, which wasn’t the touching I wanted, but it insinuated that she acknowledges the kind of relationship we have.

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? Continuing on, we had spent half an hour in my room with my rocking her back and forth, her heavy breathing, my bucking to be closer, and the sound of me smacking her butt. She had to be home by curfew so it was cut short. A few days later she asks me if I want to spend the night, I say yes knowing there’s a possibility she might get bored of begging me to pleasure her and give in and make me want to pleasure her. We get up to her room and I want to get her a little excited so I give her a nice backrub (which is also normal for us) only this time also massaging her legs and teasing her by moving up the thigh and making her but juggle around and the fat on her thigh press upon her vagina. She was clearly loving it, because when I would stop to check my phone she would grind her butt up into me. I finished without pleasuring her. We go on to watch tv and snack like normal. I fall asleep before her, coming to the conclusion that nothings going to happen. I was up to her scooting one of her legs under me. She is on her side. I am half awake but quickly drifting back into sleep, and hardly register the fact that she’s gripping my leg between hers. She then starts flinching her thigh muscles which woke me up completely. She does this to insinuate she’s horny, every time I sleepover. I wanted to have her beg, I was turned on that she wanted to have me pleasure her, but also disappointed she still hasn’t tried to pleasure me, I wanted her to beg. She did, but not vocally. I ended up making her orgasm for the third time just rubbing her with my leg. She cuddled me, but let me fall back asleep. She’s a pillow princess.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

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? The next morning everything was normal, we didn’t mention it, I sat in the bathroom while she showered and it was like nothing had ever happened. I don’t regret it, after all, I am very into girls, and I may have a crush on my best friend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more, Power / Dominance, Just happened, I don’t know why, just went along with it

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

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

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

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? Feeling wanted, and pleasuring her.

What was the WORST thing about this hookup? Not getting any.

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? Fairly positive

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I think casual sex is okay.

What do you think about the Casual Sex Project? Love it

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