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Been meaning to write this up for a while and – thanks to a slow day at work – I’m just finally getting around to it. This story took place about a year and half ago. I had recently moved across the country to a new state where I didn’t know anyone. After a couple of weeks of getting settled in my new job and finding an apartment, I fired up the dating applications. I still didn’t know anyone, so I wasn’t really sure what I was looking for. I guess I was open to all encounters.

Maddie was the first person I matched with. She was about 5’3″ with dark hair and pale skin. She had a nice smile and kind eyes – giving her a girl-next-door vibe. She had also recently moved to the area and didn’t know anyone either, so I suggested meeting up and checking out the local climbing gym.

We met up at the gym on weekday evening, but we didn’t end up climbing at all. Instead, we spent the entire evening sitting on the couches talking about our lives. She got married young, but her husband was more a homebody and she enjoyed traveling and trying new things – so they eventually grew aside and got divorced. Then when COVID hit, her job went fully remote and she used the opportunity to move from the upper Midwest to Mountain-West. She kind of bounced around different cities and states, before settling in my new city. She was also religious, which I only mentioned because that’s not really my thing and because it was a little surprising – especially in hindsight.

At the end of night, we hugged and went our separate methods. I think it is fair to say that I wasn’t in love, but I had had a nice time. Plus, I still hadn’t met many people, so I texted her to see if she wanted to meet up again and she replied that she did.

For our second date, we decided to grab dinner and then sorta bar hop through downtown afterwards. She wore a dark, flowy summer dress with wide shoulder straps. It was a modest, but revealed a hint of cleavage at the same time.

Perhaps it was the alcohol, but this date was much different. The conversation picked up where we left off, but there was a lot more flirting and touching. She laughed at my jokes, brushing her hand against my arm. And as a the night wore on, my hand would rest on her thigh. As a we hopped from one bar to the next, we hold hands or I guide her across the street with my hand on the small of her back. And towards the end, we ducked into an empty storefront’s entryway for a quick kiss.

Eventually, we decided to call it a night and I walked her back to her car. I was parked a few blocks away in a different lot, so she offered to give me a ride. As we pulled into the lot, I pointed out my car and she pulled into the space next to it.

I told her that I had a nice time and we both leaned in to kiss. It a was a slow, deep kiss that lingered for a moment. Followed by another and another. As the kisses became a bit more passionate, I asked if she wanted to get in the back seat and make out. She laughed and said sure.

We climbed into the back seat and any sense of propriety went out the window. She straddled me and we began to make out. My hand ran up her sides and all over her body. The fingers f my right hand laced through her hair and pulled her close, while my left grabbed her ass. After a few minutes, I reached around the back of her dress and pulled zipper down. The dress slid off her shoulders. Her tits were much larger than her modest dress let on (probably D cup) and I buried my face in her cleavage – kissing her tits. She reached behind her back, undoing her bra. I took one of her nipples in my mouth, rolling them between my lips before kissing her again. I started to hike up her dress and I could feel how wet she was, even through my jeans. I looked down and her panties were soaked through.

I asked her were she lived and if he wanted to go back her place, but she lived 30 minutes away. She asked about my place, but I was still waiting on my furniture to arrive at my new place. We both let out of a collective sigh. I told her how badly I wanted to fuck her in-between kisses. She let out a moan and said “Just do me here.” I leaned to ask her if she was sure and she replied “Yes, just fuck me here. I want to feel you inside of me.” I whispered “Fuck” in her ear and gave her ass a light slap.

She leaded back a little and began undoing my belt and pants, while I admired her tits. She pulled my cock out of my pants and raised my hips so that I slide them down. But she pulled her panties to the side and lowered herself onto me. She was so wet, it was amazing. And, I’ve never forget the face she made when my cock pushed inside her – her head tilted forward, eyes closed, mouth agape. Her car was a sedan so there wasn’t a ton of room, but she started slowly bouncing up and down on my cock.

The sun had set, but there was still enough ambient light from the parking lot lights that we had to be a little careful should anymore happen by – they definitely would have seen what was going on. More than once, we had to pause and duck down a little when a car would pass.

Eventually we found a good rhythm and positioning, so I was able to fuck her a bit deeper until we both came. We just sat there for a while, still kissing, my cock inside of her. I could feel my cum begin to tickle out of her and pool on the back seat.

We ended up meet up for a few other dates, but none no where as hot as this one and things eventually fizzled out.

NSFW: yes

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