My Friend’s Older Sister



What’s your gender? Man
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
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 13
How many hookup stories have you here posted before? 1

My Friend’s Older Sister

How long ago did this hookup happen? A few years

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 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 the older sister of one of my friends. The two of us were in a band and his sister often came to our shows. She was very girl next door. Plain, dressed in baggy clothes most of the time. brown hair, didn’t wear much makeup, a little chubby but thick. She was into anime and I liked her but she was a little awkward.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After a show all of us went to my friend’s house to get really drunk. The other members of the band were a lot crazier than me and the parties often got pretty wild. The night is fuzzy in spots, I remember playing drinking games: kings, never have I ever, truth or dare. At one point my shirt came off and I could feel her staring at me. Later in the night someone dared both the girls in the room to flash everyone and they did, her tits were way bigger than I expected and I started to get a little turned on. We chatted throughout the night as everyone became more wasted and eventually passed out.

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 laid down on a pullout couch in the middle of the living room, my other friend was asleep across the room. I make the first move and pull her close to me and grab her ass. She gives me a really surprised look, smiles, and starts rubbing my cock through my jeans. Then she changes her mind and whispers in my ear to follow her. She leads me into their bathroom. She didn’t waste any time. When we got in there she drops to her knees and starts blowing me. I was surprised at how good she was, she managed to deepthroat the whole thing without gagging. After she got my cock wet she pulled off her jeans and panties and spread her legs. She had a bit of a bush which was new for me. I go to put my cock in her and she stops me, grabs me around the neck and says “Pull out or I will kill you.” I say ok, I had recently broken up with my girlfriend and had never had bareback sex before. I slipped inside her and couldn’t believe how hot and wet and tight her pussy was. I tried to be as quiet as I could with all the others in the apartment but it was hard. I pulled her shirt up to get another look at her huge tits and I start sucking on them. She pushes me away and says “No, I want to see.” I look up and she is staring at my bare cock going into her pussy. I stare too, not believing that I was fucking this girl I had known for years and years. After a bit, I’m ready to cum so I let her know. She tells me to pull out and shoot it in her mouth. This is my first time pulling out, and I’m also very drunk so it doesn’t go so well. I shoot my first spurt of cum inside her before I can get out all the way. She leans down and deepthroats me until I’m finished. When we’re done she leans back and I collapse on top of her, breathing hard. She laughs and says she can’t believe this happened. I agree. She looks me in the eyes and starts playing with my cock which is still mostly hard. She starts rubbing it against her pussy and slips it inside. I can feel myself starting to go soft but I roll with it and start fucking her again. I guess she came to her senses because she pushes me off and says we have to go to bed.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? I freaked out because she wasn’t on birth control and I came a little bit inside her, but she didn’t get pregnant. She tried to ask me out on a date but I politely declined. She was the sister of one of my friend and the hookup shouldn’t have happened in the first place.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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? 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? Not at all

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The situation was very hot and spontaneous, the thought of cumming in her pussy unprotected is also a huge turn on

What was the WORST thing about this hookup? Thinking of how my friend would react if he found out

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 love it

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