(TLDR at the end)
(Skip to ————————— for sexy time)
I matched with this girl on Tinder (we’ll call her Jamie) that had only one blurry picture, which was always a gamble. On top of that, her profile said she was 32 and I hadn’t been with someone in their 30s before. But I still saw it as an opportunity to meet a new person and maybe more would come of it. We started chatting and eventually decided we would meet for a bite and walk around the park together. She seemed pretty shy and didn’t share too much about herself over text, so I was interested to see what she’d be like in person.
I got to the spot first and waited in my car for her to arrive. She soon pulled up in a car similar to mine but 5-10 years older. We met each other’s eyes and smiled, then got out of our cars to walk in together. She was short and thick, though both of us were bundled in jackets so it was hard to fully make out her figure. I held the door for her and followed behind as we walked to the counter and ordered, then sat together at a table. We chatted about where she was from in the midwest and what brought her to where we were in the south. She was shy and sweet, and was slowly opening up to me about herself. After we ate we walked out to her car to drive to the other side of the park to walk around. Once we got there we got out and started to roam aimlessly, chatting about our backgrounds and the differences between them. As the evening went on, we started to joke with each other and all of the first date nerves evaporated.
We were having a good time, but we were both getting cold and tired of walking, so we made our way back to her car and drove back to our initial meeting point. It was getting late now and we were out of things to do, so we made plans for another date and said our goodnights. Before I got out of the car, I felt the urge to kiss her goodnight. And I did kiss her. I could tell she was glad that I did, because she was beaming when I said goodnight and stepped out of her car.
When I got home and texted her that night she told me she was surprised by the kiss, but that she was definitely happy about it. Over the next few days we texted and flirted a bit, and we planned to meet one day for dinner. It turned out that our schedules didn’t work to do dinner together, but one night she invited me over to her place. It was short notice, but I wasn’t doing anything that night so I drove to where she lived.
When I got there, Jamie smiled and invited me in wearing her pajama pants and a t-shirt. The couch and tv were right inside the door, so I took off my jacket and took a seat next to her. I put my arm around her shoulders and she leaned into my chest. I could feel her warmth against me, especially after coming in from the cold. The time felt right, and I leaned in for the second kiss, which she gladly reciprocated.
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The second kiss lead to the third and fourth and before I knew it I was on top of her on the couch, touching tongues and feeling her up under her t-shirt. She wasn’t wearing a bra, and feeling up her bare tits was making me grow harder. She noticed this, and eagerly slid off her pants to reveal her lacy black underwear. I followed her lead and removed my pants, giving her a glimpse of my bulge through my boxers.
She took off her shirt and underwear and I pulled down my boxers. I remembered at the last second to grab a condom, and once I had it on I leaned back over her naked body. We resumed kissing as I pressed the head of my cock against her pussy. I slid it in further and back out, a bit at a time, until she took it all. She moaned my name with pleasure as I thrusted deep into her, her legs wrapped around my back pulling me in. I wasn’t prepared for how quickly this had escalated, so I soon found myself getting close to cumming much faster than expected. I decided to go all in and pound her pussy through my orgasm. I grunted and exploded into the condom, and tried to keep up my pace. She rubbed her clit as I continued to fuck her, and before long she was cumming on my cock. I slowed my pace as we exhaled with pleasure and kissed before I pulled out.
I threw away the condom and cleaned up, and joined her back on the couch. Neither of us put our clothes back on, we just cuddled up again on the couch naked. My cock was soft after just cumming, but that didn’t stop her from stroking and playing with it as we sat together. She commented on how great the sex we had just had was, and implied that she wanted to go for a second round. I wanted to, but I was going to need some time to recover to be able to go again. She looked up at my eyes and asked if I wanted her to suck my cock. I wasn’t going to turn that down, so she took me into her mouth and lightly sucked until I started to grow again.
Within a couple minutes I was fully hard again and she was sucking and stroking my full length. She pulled away and laid on her back again, and gave me a look that said “fuck me.” I realized I had only brought one condom with me, so I made a mental note to pull out once the time came. I moved between her thighs and pushed my cock up against her pussy. She was wet with anticipation, and she felt incredible on my bare cock as I slid deep into her. Once I had worked my cock into her wet pussy, I started pumping like earlier. She wrapped her legs around my back and pulled me deep into her, her hot wet pussy engulfing my cock with every thrust.
She was moaning and loving the feeling of being stretched and penetrated deeply by me, but on the other hand I could feel another orgasm quickly approaching. I went to pull out but her legs held me inside of her. As much as I wanted to fill her with my load, I didn’t know if she was on bc and I wasn’t prepared for that situation. I told her I needed to pull out and she moved her legs, allowing me to cum all over her stomach.
Once I was finished, I got her a towel and we both cleaned up. I got dressed and kissed her goodnight, and drove back home. She texted me that night and said we should definitely do it again sometime, which was when we became friends-with-benefits. I later learned that she wasn’t on any bc but was going to start on it soon. I was both relieved that I hadn’t cum inside of her, and excited that I would soon be filling her with my loads.
TLDR: A wholesome first date with a girl lead to her inviting me over late at night and fucking me twice.
Source: reddit.com/r/gonewildstories/comments/vbbq3j/an_innocent_first_date_leads_to_her_f_becoming_my
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