by Dana

Gender: Female
Age: 19
Race/ethnicity: Asian
Current location: Melbourne, Australia
Highest education received: Some college (currently in college)
Relationship status: Single
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? None

Green Heart Panties

How long ago did this hookup happen? 3 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-night stand

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? He was my then-bestfriend’s older brother. He was basically a tall, male lookalike version of her. I didn’t know him very well, but I knew OF him. I knew he had a reputation and I knew I should be wary of him. Actually, almost one year exactly before our hookup, we had fooled around already. But I was too young and too drunk, so I ended up passed out on his bed. But this time around, I was recently single and wanted to “go on the rebound”, so I thought ‘why not?’. I had always found him cute in that ‘this is your bestfriend’s big brother’ kind of way. He was older and I always wanted him to see me more than one of his kid sister’s dumb friends. Funnily enough, having sex with him probably made him think of me in that light.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were both at a function of sorts where my bestfriend (his sister) was involved. We were both bored out of our minds, so we began texting. It was friendly at first, we were just trading jokes and mocking people around us. Then he sent me a one-word text: ‘blowjob?’ He was right next to me, yet gave no outward indication that he had just sent me a raunchy text. My cheeks grew red and I typed back something stupid. I tried to laugh it off. I was playing with fire and it was beginning to burn. But I knew it was too late to back out. Our texts grew more serious and his thigh inched closer to mine. He told me quietly to meet him outside and he stood up and left. I looked around guiltily, as if everyone had been privy to our discussion. I felt a hundred eyes on me as I rose (there was probably no one paying attention–my nerves were just shot) and made my way to the bathroom to do some quick recon.

Shit, I murmured to myself, shit. I wasn’t in the slightest prepared. When I climbed in the backseat of their parents’ car earlier that evening, I didn’t even imagine that I would be locked in a toilet, stressing out over my very unsexy underwear. I was wearing control top pantyhose and a pair of my most comfortable underwear: faded green panties with sickly hearts plastered all over them (and, to add insult to injury, the garter was stretched thin and there was a small hole near the butt area). Oh and did I mention I was on the last day of my period? Because I was. I quickly stuffed the pantyhose in my small black bag and crossed my fingers when I went to check my pantyliner. I did a small victory dance when I saw that it was clean and that I was no longer bleeding. I threw out the liner then I washed my hands and looked at myself in the mirror. It had been ten minutes since he told me to meet him outside. This was as ready as I was ever going to get.

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? I was wearing heels so I clumsily approached him underneath a tree. The loose pebbles on the ground were making me even unsteadier and I’m sure I didn’t look the least bit alluring. He tapped his foot impatiently and motioned with his head to follow suit. He was leading me towards the parking lot. But then he kept going. Behind the parking lot was a small wooden building and it would have been pitch black if not for the lone street lamp near the parking lot. He finally reached out and grabbed my by the wrist. I had no false expectations of this being a romantic thing, but I still wasn’t expecting him roughly pushing my head downwards. I fumbled with his zipper and sucked his cock dutifully. I had only ever been with one other person prior and I was scared of doing anything wrong. After a while, he pulled me back up again and was about to compensate my efforts. But I shook my head no and told him to just have sex with me instead. I was terrified of letting him near my vagina because I knew I had just finished my period and I hadn’t shaved in a while. I was embarrassed and I just wanted the whole thing to be over and done with.

There was a small rickety wooden staircase at the back of the building and he sat me down and pushed me back until I was lying down on the top landing (it was a very short flight of steps–probably three or four steps at the most). I was thankful for the lack of proper lighting as he pushed my underwear to the side and slid himself into me slowly. He was good. My ex was a virgin, and we lost it to each other. It was a whole new experience being fucked by someone who had a plethora of experience. It wasn’t personal or intimate, but damn, it was good. I tried to avoid eye contact because I wasn’t used to being fucked by someone who didn’t care about me. But the sex was too good for me to care about my dwindling self-respect. He did this crazy-stupid-good move that made my eyes roll so far into the back of my head I could see my brain tutting and disapproving. He would pull himself out halfway (and still leave a considerable amount because, I’m not gonna lie, he was pretty well-endowed) and then do these quick and shallow little thrusts that would make my thighs quiver. And after teasing me until I practically mewled, he’d thrust all the way in and I swear I probably passed out a little.

But then he commanded me to turn around so he could fuck me in the ass. My eyes widened and I protested. He said that all girls secretly loved it and just didn’t tell anyone about it. But I seriously doubted that. And even though the sex was good, I wasn’t about to let him just fuck me in the ass willy-nilly. So he threatened to pull out if I didn’t let him do anal, and I told him I didn’t care. He made me finish him off with my mouth anyway. I spat out his semen on the wooden stairs and before I could look up, he was already walking away.

Did you have an orgasm? Did your partner(s)? Only two men have ever made me orgasm–and he was not one of them. In my mouth, with his own hand. I was a human jerk sock.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None whatsoever because I was stupid and naive and he didn’t care. Ironically enough, I had removed a condom from my purse before heading out that night. Since I was newly single, I thought I wouldn’t have any use for it. Little did I know…

What were your REASONS for having this hookup? I wanted to stop thinking about my ex (didn’t work).
I wanted to have sex with my bestfriend’s brother (a cliche fulfilled).
I wanted to get back at my ex and win at that ‘who’s more over who’ game (I won–in the short-term).

Were alcohol or drugs involved? If so, how much? None, on my end. I’m not sure about him. I think he was sober. It wasn’t really a booze-y event.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? He told me to meet him in the park near my house at midnight when I was being dropped off home. I shook my head no. He gripped my wrist before I exited the car, but I still reneged.

I knew nothing would come of this hookup, so I had no hopes or expectations. I told no one and it’s like a dirty little secret of mine. I don’t think his sister even knows.

I feel nothing for him. I have not spoken to him in 2 years.

To whom did you talk about the hookup? How did they react? A few weeks later, I ran into my ex at a party. We confessed our lingering feelings for one another. He asked me if I’ve been with anyone else. I said yes and he frowned. He asked who and I refused to tell him. I refused to tell anyone for a long time. I’m over it now. It’s just another anecdote to me: ‘this one time, I had sex with a guy in public and he demanded anal and I said no so he came on my mouth and left ha ha HA HA ha’.

Was this a consensual and/or wanted experience for you? For your partner? Consensual on both ends.

Do you regret this hookup? If so, why? I think I regret all of my hookups–except for the ones that occur within relationships (note: 2 out of 9). My post-coital glow is a mixture of guilt and self-loathing.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I liked knowing that I fucked my bestfriend’s brother. The sex was actually good until the whole anal scare.

I went through a few more one-night stands after this one. Thankfully, none of them threatened to surprise-fuck me in the butt. I never felt good after any of them, yet I still kept going. I regret fucking anyone after about three thrusts in. I just go with the motions and chant ‘please cum already’ in my head. I still don’t know what to make of this mentality or myself. All I know is I like sex–until I don’t.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

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