My Friend’s Older Sister



What’s your gender? Man
How old are you? 27
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
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)? Around 20
How many hookup stories have you here posted before? Zero

My Friend’s Older Sister

How long ago did this hookup happen? 5 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 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? It was New Years Eve and, like the title says, she was my friend’s older sister. I was visiting my college town to celebrate the new year and I was hanging out with some old friends (but not the friend who’s sister this was). We all went out to a few different bars and I happened to run into my friend’s sister, who I always found attractive. She had dark, curly hair and big brown eyes, and huge breasts. I had wanted to touch them from the moment I saw her. She was, as the cliche goes, curvy in all the right places.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at a bar and ran into one another. Since we hadn’t seen each other in a long time, we spent some time talking and I bought her a drink. The conversation got more and more flirtatious and I started to wonder if we might be headed for a night together. We had a few more drinks and, aided by some liquid courage, I got really blunt and told her that I always wanted to fuck her and tonight was the night I was going to do that. She loved it and we immediately left for my hotel room.

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? As soon as we got in the door of my room we were all over each other. Clothes came off immediately as we were passionately kissing. There was no foreplay because we were too busy fucking each other, hard. I was so turned on by the thought of finally fucking my friend’s older sister with huge boobs that I could not have enough of her. I fucked her so hard and for so long, and she loved every minute of it. My favorite position that night was having her on her back on the bed with me standing next to the bed, her legs up in the air and me just going to town on her pussy. At one point, she leaned up and bit my chest; I moaned and then proceeded to fuck her even harder. She screamed with pleasure and I will never forget how sexy she sounded at that moment. The room I was staying in had two beds, and she asked me if I wanted to fuck her on both of them. So hot. And yes, I did. We fucked for about two hours. I only had one condom with me and so the first time I came in the condom, and then I fucked her without a condom before pulling out and cumming all over those huge tits. It was glorious. We passed out naked together.

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? We woke up the next morning and I drove her to her apartment. She knew I was just visiting for the new year celebration, so there was no expectation of anything further. She sent me a Facebook message a few days later that said “thanks for the mind-blowing start to the new year!” Safe to say we both thoroughly enjoyed ourselves.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Completely 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? I told a couple of buddies the next day. They were happy for me and jealous that I got to see those boobs.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? The fact that I finally fucked my friend’s older sister, who I had secretly lusted after for a while. And I made the most of the opportunity – the sex was flat out amazing and I still jerk off to her screams of pleasure to this day.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. I enjoy casual sex.

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? Great site!

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