The Curve and the Crash

Chapter 2: Disappointment with a Beard

I'm a 30-year-old woman, and this story is about the second guy I hooked up with--just one day after my very first ever casual hookup. Yep, I went from one partner to three in two days. 2024 really became my year.

We matched on Tinder in January. He was 29, a redhead with a beard--and I'm a sucker for a good beard. He was average height and build, nothing unusual... except for his cock. It was noticeably smaller than the others I'd seen, and it had a bit of a curve to it. Not a dealbreaker, but definitely different.

We had been talking on and off for a little while before meeting up. We had plans to meet earlier, but something always came up on his end. When we finally did make it happen, we met halfway... in the parking lot of a Canadian Tire. Classy, right?

He drove a dark, very tinted SUV, so that became our mobile hookup spot. We started off making out outside the vehicle, up against it. Things heated up quickly, and we got into the back. The SUV had captain chairs, so I ended up kneeling beside one as we kept kissing. His hands slid down into my leggings, and he started rubbing my clit--slowly at first, then faster, fingers gliding back and forth. And honestly? He was really good with his hands. Better than anyone I'd felt up to that point. He could actually find the spot and build rhythm. I was soaking wet.

He looked up at me and said he wanted to eat me out. I wasn't going to say no. I climbed into the very backseat, lay down, and he went to work--licking, sucking, and trying to devour me. He also started jerking himself off while going down on me. He was multitasking... but a little too successfully. He came. Fast. He'd talked a big game beforehand about how much he loved going down on women. But if I'm being honest... I didn't feel much. It was all tongue and enthusiasm but not a lot of precision. I tried to enjoy it, but it didn't do much for me. That was the first time i had ever had someone go down on me.

Still, I wasn't ready for the night to end. I straddled him and tried to slide down onto him... but his cock was so short, it didn't even really make it in. I tried adjusting, shifting--but before we could figure it out, bam--a pair of headlights flashed through the windshield and stayed there. Mood? Killed.

We got dressed, kissed awkwardly, and parted ways.

On the drive home, he messaged me asking if his cock was "good enough for me" and if I enjoyed myself. I was polite, since we'd already talked about meeting again. I didn't want to be mean. And maybe it was just a fluke? Maybe he knew how to use what he had.

But... I never found out. He ended up ghosting me...... Stood me up after we made new plans. So I guess he became my first true one-night stand.

And still... haven't cummed

Chapter 3: 20 Years of Wanting Me for 20 Seconds of Action

I (30F) had known this guy (31M) basically my entire life--so this was my first hookup with someone I already knew.

A little backstory: we went to school together, and I was even friends with his sister. I used to hang out at their place all the time. I always knew he had a thing for me--and maybe I had a little crush on him back then too--but I never thought much of it.

When I joined Tinder, he popped up pretty often. But I always swiped left. Too close for comfort. Too real. It was kind of scary.

Then one day in January--just five days after my second hookup--there he was again. I messaged my very supportive best friend and asked, "Should I swipe right?" Her response "Yes. Do it!" So, I did. We instantly matched. My opening line?

"Hey, random--but would you be interested in some hookups?"

He replied, "Are you sure?"

I said, "Nope! But I'm in my fuck it era."

He's fit and muscular, taller than me, and thick--not just down there (although, we'll get to that)--but in a solid, strong kind of way. Short and thick. Honestly, at that time, the thickest I'd ever felt.

A few days later, we planned to meet... but my body had other ideas. So instead of sex, we ended up making out in his truck. Things got hot fast--I was stroking his cock while he bit my lip and spanked me. The second he did that, I knew I needed more.

I gave him a handjob in the back seat, and he exploded. I mean exploded. There was so much cum, he literally started shaking from how hard he came. That was new for me--and definitely turned me on.

February rolled around, and it was finally hookup time. We parked on a no-winter-maintenance road, climbed into the backseat, and things escalated fast. I was already soaked and just wanted him inside me.

That first thrust--I moaned as I felt his thick cock stretch my tight pussy.

He started thrusting hard and fast--so hard I thought I might fly right out of the damn truck door. I was holding on for dear life. And honestly? I was into it. I love fast and hard.

But... Turns out he was basically a 5-pump chump. He finished way too quickly. And apparently, he could never go more than once--at least, that's what he told me.

A month later, we hooked up again. I was actually supposed to meet another guy (Hookup #4), but he convinced me to come to his house first.

That round? Lasted maybe five minutes. Tops. All about him. No effort for me.

And still--I went back one more time. Third time's the charm? Not exactly. I gave him another handjob, and again, he came before we even got to the sex. Looking back, I think what made this one feel so exciting was the secrecy. No one knows I slept with this guy. Not even my best friend. No one suspects a thing.

And yet..

I still haven't cum.