About a decade ago, I was out to eat with a few friends at an asian restaurant while on a road trip when the waitress walked up to our table. I was instantly taken aback. She wasn’t just pretty. She was hot. She was curvy, thick, great chest. Later I saw she had a terrific ass.
She did her usual introduction and took our drink orders. I was in one of those don’t-give-a-fuck moods because I was in a different city and knew I would never talk to her again. Or so I thought.
I started flirting and shooting my game. It was kind of working at first. Then she kept dropping by our table more and more, so we kept talking more and more. It turns out we randomly had some mutual friends in common from a city she used to live in years ago and then she said she was going to be running in a race the next day that one of my friends from that city was going to be running in also.
“Come by the race and cheer me one,” I remember her saying.
I said I’d think about it. As soon as she walked away, my friends, who knew what kind of slut I was, encouraged it. When she came back to our table, I said I’d definitely be at the race. She suggested just meeting me at the finish line.
Then our food came so I didn’t really talk to her the rest of the night.
Before we left, I got up from the table and found her in a different part of the restaurant. I asked for her number and we talked a few more minutes.
We texted a little bit that night but nothing dirty or raunchy. She said we could hang out after her race if I wanted to. That’s when I started thinking something was up – and it wasn’t just my cock.
The next morning, I woke up early with a hangover and drove with my friend to the race.
I just hung out during the race until the waitress texted me that she had finished. The plan all along was for me to just go hang out with her after and see my friends whenever. We found each other near the finishing line and she was was wearing these short shorts, a tank top and a sports bra. She was super sweaty, which I loved, and her tits looked fantastically big.
We hugged and talked while she stretched. I tried looking up her shorts but I didn’t see anything.
She asked if I wanted to grab lunch and hang out by her pool. I quickly said yes so we left.
After picking up sandwiches, we went back to her apartment. She wanted to get out of her running clothes, so she went to the bathroom and came out in a robe. I felt my cock twinge. We decided to eat our lunch by the pool so she went back in and changed into a bikini.
By the pool, we just sat in the chairs and ate, talked and flirted. I was nervous to make a move because I was on her turf and if she rejected me, I had no where to go until my friends got me. Then hopped in the pool, which was so incredibly relaxing and cooling. We stood facing each other for a little and then realized no one else was by the pool so we got a little closer.
I figured this was the time, so I went in for a kiss. She was down. We began making out in the pool and she quickly wrapped her legs around my waist in the water. I got super hard at this and she could tell, so she started to gently grind her crotch on mine.
We hung out for a little while more and then went back to her apartment, making out every few feet. Once we got inside, it was game time. I stripped her bikini off, which is one of my favorite things to do, and she slid down my bathing suit and quickly wrapped her hand around my throbbing cock.
She was kind of shaved, which I love, so I felt that for a little while before rubbing my fingers inside her slit. When I took off her bikini top, her huge tits just popped out. They were gorgeous. Perfectly sized areolas. Big nipples. Firm. It was heavenly.
We fell on her bed while making out and my cock almost slipped in she was so wet. She told me to get a condom from her night stand because she was too sore to move because of her run. I did but when I got back on the bed, I told her to spread her legs. I started kissing up her thighs, tasting the salt from the pool mixed with her sweat. When I got to her upper thigh, I could feel the heat from her pussy on my forehead. I didn’t waste any time after that. I sunk my tongue into her hole, her wetness covering my mouth and nose. I nibbled on her clit for a few seconds, which made her moan. Then she told me to come up. That meant one thing only. I sat up on my knees, unwrapped the condom, slid it on and entered her. We were flat-out fucking. I held her legs up under he knees and fucked the shit out of her.
We went for a long time. She couldn’t get on top because her legs hurt too much but I was able to flip her over and fuck her doggy style. Watching my covered cock slide in and out of her was too much to handle. I reached down to feel her hanging boobs and orgasmed inside her, filling my condom with days worth of cum.
We laid there for a while and snuggled. She took off my condom and stroked my cum covered cock while we made out. We both fell asleep naked. When we woke up, it was evening and I had to get back to my friends for dinner. We promised to stay in touch.
And we did. We sexted for months. About a year later, we were coincidentally in the city on the opposite side of the country. I told her I was meeting up with an old buddy for beers and she should join. She drove about an hour to meet up. We had a few drinks and talked, and then we headed back to my friend’s place, where I was sleeping on a pull out couch. We didn’t waste any time getting naked. And this time I made her get on top. She rode me for about an hour and then I came into the condom.
She said she had a migraine – which to this day I think is bullshit – and then she went home.
She met her future husband the next week but I jerked off to her for months.
Source: reddit.com/r/gonewildstories/comments/mavf9e/i_m_fucked_a_waitress_the_day_after_she_served_me