A Freaky Night with My Friend



What’s your gender? Man
How old are you? 17
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Sydney
Highest education received: Not graduated from high-school
What’s your occupation? McDonalds cook
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? None

A Freaky Night with My Friend

How long ago did this hookup happen? Two weeks ago

What was your relationship status at the time? Same as current status

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? My partner (we’ll call her Anne) had dark black hair, pale skin and a nice ass. She had small tits, like 32AA, but they still were great. She was pretty short, about 5’1″. We’ve known each other for about three years. I’d always wanted to fuck her, but I didn’t know if she liked me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were both at this party late at night. We were both sitting on the sidelines of the dance floor just watching other people dance. We started talking about relationships and she said nonchalantly, “I feel like you’d be a good fuck.” I was quite taken aback and just said, “Oh yeah?” She smiled and told me to follow her to a private place.

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 entered the bedroom, she started to strip for me. She slowly took off her shirt and only wore a skirt, a black bra, panties, and boots. Then she removed her bra and panties and flung them at me. She strutted up to me and slowly took my clothes off. She dipped down and started to suck the tip of my cock, going further and further down my shaft.

She deep throated me for a good two minutes before she took my dick out of her mouth and placed it at her soaked entrance. I slowly pushed inside her as she began making little squeaking noises as I pushed through. We fucked in missionary, doggystyle, cowboy and 69 before we tried anal. For that, she began to yelp and moan when I put it in her. As I fucked her ass and fingered her pussy, her eyes rolled into her head as she orgasmed all over my hand. I came in her ass, which sent her over the edge as she fell over and began to rub her clit and tits.

I got on the ground and started eating her out until she came all over my tongue. She got me hard again and then sat on my cock and told me that we were going to sleep with my cock inside her. I happily obliged and by the time I woke up the next morning, I caught her sucking me off. We then 69 again and fucked in missionary again. As she left she told me to call her, cum dripping down her legs and thighs. It was the hottest experience of my life.

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? I felt great and I’ve been maintaining a friends-with-benefits relationship with her.

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, Attraction to partner(s)

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? 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.

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? That she wanted to keep fucking even after the hookup ended.

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? No.

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

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

Anything else you want to add about this hookup? No.

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 an important link between people to enhance a relationship on a sexual level yet still remaining friends.

What do you think about the Casual Sex Project? It’s great!

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