My Brother’s Best Friend



What’s your gender? Woman
How old are you? 20
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Some college (currently in college)
What’s your occupation? Horse trainer
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 0

My Brother’s Best Friend

How long ago did this hookup happen? Today

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 less than a year

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? Pat is about 6 ft tall, with orange-brown hair and beard, lots of body hair, and hazel eyes. He drinks a lot of beer and is getting a little bit of a beer gut. He has an adorable smile. He is my brothers best friend, and my brother is also his boss. We matched on tinder. I saw his profile and swiped right simply to see if he had liked me, and he did. However, he hadn’t realized it was me. We started talking and eventually started snapchatting. We’d spoken in person a few times before when he had been over to help my brother with things (I also live with my brother). We always had good conversation and I thought he was a great guy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I am staying at my parents’ house while they are on vacation. I tried to talk him into coming over to use our hot tub with the secret intention of trying to hook up with him. I’m always very horny after finishing my period and I was feeling like I was about to burst. I finally just told him I wanted him to come over and have sex with me. We sat in the hot tub and then got in the shower together. After the shower, we went back to my bedroom.

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? After laying there and talking for a bit, he finally kissed me. I told him I was horrible at first moves, so I was glad he did it. I got on top of him and straddled him while continuing to kiss him. I started grinding on him but his dick was at and angle and not sliding between my lips like I wanted it to. I felt down and wrapped my lips around his dick. He let out little moans. I started going up and down and gagging myself with his cock. He was dripping precum. I got up and got a condom. He started slowly from behind, then going faster. He lasted about two minutes. He warned me before hand that he didn’t know how long he’d be able to last. We laid back down and started talking again. I didn’t know how to tell him that I wanted him again. So I started talking about my body. My large butt, tattoos, and pierced nipples. I couldn’t tell if he was getting hard because the blanket was over him. I had to bend over him to get something on the other side of the bed. Then I had to do that same thing again. He was joking asking me if I was doing it on purpose, and I wasn’t. While we were laying there, I had told him I liked being spanked. I had to lean over him once more to put something down. He sparked me and I let out a moan. He was running over my butt and his hand slowly reached into my crotch. He stuck a finger in my pussy and started pounding away. I loved it. He flipped me over and went down on me. I normally don’t have much feeling in my clit, but his tongue was amazing. He held my legs apart and I started grinding on his face. I had dreamed about having my pussy juice on a man’s beard before. I almost came, but I was shy and the feeling was so strong. He asked me if I had another condom and I did. He took me from behind again. He started pounding my pussy and spanking me. It felt so good. I could feel the warmth as he came.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, but I was 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? As of right now, I would easily have sex with him. I have a low cervix which makes sex painful if the penis isn’t the right size. He is a bit on the smaller size so it didn’t hurt that much.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, I was feeling lonely, It was easy / convenient

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? Very

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

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? No one. And I plan on telling 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? 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 WORST thing about this hookup? Him being a little bit smaller than normal and me being shy.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. All I have ever really had is casual sex.

All things considered, how POSITIVE was this experience? A little 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 everyone should try casual sex. It’s not good to have pent up sexual frustration. There is no need to worry about disappointing them or possibly ruining a relationship if you don’t already have one

What do you think about the Casual Sex Project? I love it. I cannot get into erotica. I can only get turned on by hearing stories that are true because it actually has a chance of happening to me.

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