Fucking [m]y OkCupid date [f] in an Applebee’s parking lot

Let me start out with an important fact about me: I am very lucky when it comes to casual sex, and very unlucky when it comes to love. The unlucky in love is likely because I am overly focused on it, or overly particular. Or…well my friends have theories. But the sex thing – I have no idea. I am not some Adonis or anything. Not that I’m bad looking, but I’m not special either. Being 6 ft tall and Height-weight proportionate are probably my best features. My face is average, I have dark hair and brown eyes. At the time of this story I was 26. I am not rich, nor am I particularly charismatic or anything. I think i’ts just luck.

And while it’s fun, honestly I wished it were the other way around. This story starts about 4 months after I had broken up with my girlfriend of a little over a year. After a great honeymoon period, things just kind of fell apart. It was pretty amicable as break ups go, but it was still heartbreaking and I wasn’t in a great place after.

And after a few months of moping my friends made me make an okcupid account. I went on and messaged girls, got shot down. Until Jessica. I honestly didn’t put a ton of work into any of the messages, and Jessica didn’t seem to either. Her profile was bland, so that made it even harder. But it was more about getting back out there so I asked if she wanted to grab a drink the following Tuesday. To my surprise she said yes. I asked if she had a preference and she sent an address.

I didn’t look at it, but we agreed to meet at the spot at 8.

Another thing to know is that, really since graduating high school, I’d lived in major cities where a car was just not needed. College and my post college life was basically car-free, and that colors what happens next.

So imagine my shock when I dropped he address into my phone I saw it was no where near where I thought it was. It was a simple mistake, but one that meant instead of taking transit home and then another 15 minutes to this place, I needed to uber a solid hour out.

Great. I almost cancelled. She was cute, very mid-western looks if that means anything to you, Dirty blonde hair, 5 ft 6, slender with what seemed like a nice-ish chest. But very plain, and from her profile I got no personality. So my interest was low. Ultimately I figured that made it a better thing to go. I won’t run into friends out there, if it’s bad no big deal. Just some wasted Uber money.

So I went out, and traffic was worse than expected. I was 15 minutes late. I messaged her ahead of time to let her know. To my slightly surprise she didn’t seem that mad. She was cute, just like her photos, wearing a knee length skirt that was modest without being overly so and a nice blouse.

We got talking. I learned a great deal about her exceptionally boring job -which she also found boring but talked about for nearly a full 30 minutes. Aside from the discussion of a fairly obscure TV show it was a pretty boring discussion that managed to go the obligatory 2 hours.

At 10 pm in a suburban Applebees on a Tuesday night things are pretty dead. They were starting to close, so I paid the bill – I had two beers, she had two ciders – and we went outside.

Now I need to describe the layout here – this Applebees was in the parking lot of a large strip mall, not directly attached to the main row. Instead it was kind of an island out on the edge, by the barrier to the road that lead to the main road.

So we walk out and her car is in the closest non handicapped spot. Otherwise there are a smatter of cars much further out, presumably late shoppers or employees of the stores. We say our “I had a nice times” and go for the hug. And I’ve felt zero chemistry, but she was cute and ya know why not?

So I went for the kiss. I expected her to dodge. Or just do a quick kiss and break it. But to my pleasant surprise she didn’t. After a minute, I slipped my tongue in and she was very receptive. We moved closer, my hands were on her hips., I figured…maybe we had more chemistry than I thought?

So I slipped my hand down to her ass. It was nice sized and great to grab, so I grabbed it,, She broke the kiss and said “oh wow…aggressive.” but in a tone that encouraged and suggested she had been pleasantly surprised.

I wasn’t sure how to respond, so I just kissed her again and we kept at it for a minute before she broke the kiss again.

She pulled away a bit and said “Not that I mind but maybe we should take this to somewhere more private” and gestured to her car.

Now the last time I used cars regularly in a dating setting was in high school, and cars were a great place for amorous activity between people who can’t get privacy at home. As an adult I had an apartment with a room and a door and roommates who would (probably) behave if I brought a girl home. Presumably she did too, but maybe not? Maybe the car was the best option. In any case it sounded fun.

So I said “sure” and lead her over to the car as she clicked the unlock button on her key chain, and I pulled open the back door. She climbed in after what seemed like a moment of hesitation and I followed. She drove a mid-size suv, and her back seat was a nice comfy bench with a good amount of room. So there was no issue when we began making out even more furiously than before. My hands went up her shirt and undid her bra.

Her hand meanwhile went into my pants, stroking me hard and then undoing my belt and pants. She pushed them down and climbed on top of me. Her bra was hanging off, and her blouse was undone, as she moved down on my exposed cock her skirt hiked up, becoming more belt than skirt, my cock pressed against her panty clad pussy, rubbing up and down as we kissed. She muttered “I can’t believe we’re going to do this.”

By way of response I reached under her skirt and pulled her panties aside, letting her pussy lips slide up and down my cock. Then I use my thumb to rub her clit gently in circles, the combo had her moaning into my mouth as I kissed her, and then break her kiss and bury her face in my shoulder as she moaned loudly and ground her pussy into my cock.

When she pulled her face out and slowed her grind I said “you ready?”.

She nodded and lifted herself up. I guided my cock in, playing at the entrance before she began to lower herself onto me. Now my cock is just about 6 inches long, a nice average length. But it’s also a little over 5.5 in around which is quite above average girth wise. The result is most girls need to take their time in sliding down me.

She was not one. She clearly could handle thicker cocks and slid down me nice and steady. She wasn’t loose, just not as tight as many. It felt amazing, esp after a 4 month dry spell. And it meant she could go right into riding me. She was bouncing hard and moaning into my mouth as we kissed, my hands twisting and groping her tits as she did.

I reach down again to rub her clit as she rides me. It was a bit awkward trying to keep up with her motion, but as i was able to maintain contact she broke the kiss again and buried her face in my shoulder. I could feel her moaning and her body was spasming as she came. And it wasn’t long before I joined her, shooting my load into her as she came down from her orgasm.

We both just sat there for a minute, breathing. She broke the silence with “I can’t believe I just fucked a guy in the back of my car in an Applebees parking lot.”

I smiled “Heh, I didn’t expect it either but it was a good idea, I didn’t have you pegged for that wild but I like it.”

She looked at me confused “…It was your idea?”

I paused “You said we should go somewhere more private and gestured to your car.”

She looked at me, realizing I wasn’t joking, my pants still at my ankles, my semi-soft cock still partially in her. “I meant we should go back to my place using my car…”

My eyes went wide “Oh shit…”

Then we both laughed. “The offers still open…but you’ll have to wear a condom next time. ”

I laughed and we get dressed. After checking to make sure no one is looking we move to the front seats and she starts too drive us back. “I’m so surprised no one saw us.” She says as we round a corner. There we pass several kitchen staff smoking out back. They see us and give a thumbs up.

The look of mortification on her face was honestly hilarious.

**Conclusion** We had sex again in her apartment after watching the show we talked about on her tv. We hooked up a half dozen times after, none were nearly as exciting. Eventually the “We have basically nothing in common” factor meant there was no relationship and we lived too far away to really be easy fuck buddies so things just kind fell off.

Source: reddit.com/r/gonewildstories/comments/k2gdcx/fucking_my_okcupid_date_f_in_an_applebees_parking