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I [M] got jerked off by my date [F] under a towel at a hotel pool we snuck into at night
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dadmcdad24 is a male
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I love thinking about this story.

Right before one of my birthdays, I went on a first date with a woman I met on a dating app. She was a young professional like myself and we connected on a lot of different levels. She was beautiful with short blonde hair and a bigger ass that I just adored from the pics I saw. 

She had tickets to an NBA game in our city so she invited me to that as part of our first date. We had talked for a few weeks so we had a pretty good foundation of conversation and flirting. I also got dirty with her a few times and she threw it right back at me so I knew we were sexually compatible, as well. 

I'll never forget what she wore: A black and white striped maxi dress with a jean jacket. 

We met outside the arena and went in. We grabbed a couple of beers and went to our seats, which were way up high in the upper level. I noticed quickly that the lights were pretty dim near us. As we drank our beers and watched some basketball, we started to get more and more comfortable being with each other in person.  Eventually we started holding hands in her lap - over her dress, obviously. While we were holding hands, I used a couple fingers to start rubbing her over her dress but near the waistband of her panties. She spread her legs a little bit and i was able to push her dress a little further down in her crotch and keep rubbing. 

Then she casually put her jean jacket over her lap like she was cold and I knew it was on. I had to be subtle but I hiked up the front of her dress slowly and coyly until I could feel her bare thighs. Then I slowly made my way up her thighs and could feel the heat from between her legs. She spread them a little bit more and as subtly as I could, with a game going on in front of me, I found the lace fabric of her panties. I began rubbing slowly but with a little pressure so I didn't bring any attention to us. Then she put her legs on the seat back in front of her and spread her legs a bit more and leaned back in her seat enough to not be noticeable and so if you looked over, you'd think she was relaxing with a beer watching some hoops. I knew that was my shot. I moved her panties to the side and felt a rush of heat on my fingers. She was soaking wet. I rubbed her pussy for a few minutes and then slid a finger inside her. Her body jumped a little. She looked at me with that look...you know the one: I want to fucking kill you and fuck you at the same time. She let me finger her for a few minutes moments before tugging at my hand to pull it out. 

When the game ended, we tried to figure out where we were going next. We couldn't keep our hands off each other. We were making out and touching and hugging and everything in between. She was rubbing my cock over my shorts anytime we stopped at a crosswalk and made out. 

We decided to make our way to a hotel down the street. We needed somewhere to go, somewhere private or semi private to just ravage each other. We walked all over the hotel trying to find somewhere where we didn't think people would be. We both knew what we wanted: For me to hike her dress up and slide my throbbing cock in her wetness, raw and hard. 

We saw a door to the pool and decided that was the spot. There were a few people in the end of the pool closest to the door so we walked to the far end of the pool deck, which was empty and dark. We took two chairs and moved them to face each other and then we covered our laps with a bunch of towels to make it look like we were cold and were just warming up. 

We kissed a few times but she didn't waste any time. We looked around and no one was paying us any attention so she unzipped my shorts and pulled out my cock and started stroking me under towels, on this pool deck, in between a few high rises, under the stars. I don't think I've ever been as hard. For someone who loves playing in public, this was heaven.

We played it off perfectly but holding a normal conversation while my cock was in her hand and she was slowly stroking me. I had one leg on the ground and the other stretched out on one side of her. We looked casual. 

The slow stroke was heavenly and miserable simultaneously because all I wanted to do was cum. 

Here's where it got interesting: While we were sitting there, her stroking me, a family showed up and started playing in the pool near us. We stopped for a moment with her hand still on my cock, but when we realized they never looked our way, she started again, slowly jerking me off with the perfect amount of pressure and touch.  And it worked. I stopped talking and she knew I was close and sped up a little bit. I hit that point of no return and shot rope after rope of cum into her hand as she kept stroking me while I was cumming. When I was done, I leaned back in my chair out of breath. She used the towels to wipe her hands off and then we got up and left, just like that. 

Every time I see that hotel, I smile and text her. 

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Posted
6 months ago