A Late Night Swim

“Come on guys, let’s go for a swim. It will sober you up a bit before bed.”
“Dude I’m way too fucked up. I’m going to sleep, not for a fucking swim in that nasty hotel pool.” Said James, one of Kevin’s two friends that had come on this mini vacation. The three buddies had gotten time off from their summer jobs and had decided to go on a trip before they all had to go back to college in September. After a very small amount of planning and 13 hours in a hot car together, they had come to a relatively cheap hotel that was close to Florida’s coast. Their time in Florida so far had consisted mostly of drinking and the three now found themselves very very drunk.
“Yeah I’m fucked too. Go swimming if you want though man. Knock yourself out bro.” That was Dean, the third friend, he was the tallest in the group but was by far the drunkest, he put his hand on Kevin’s shoulder for support as he talked with him.
“Fuck both of you.” Kevin grabbed a bottle of Captain Morgan from the hotel room’s desk before saying “I’m going swimming.” And walking out the door.
Kevin had his eye on the hotel’s pool since they got there. He had been trying to get his friends to go for a swim for a while but the complaints about it being too crowded and filled with young kids were valid excuses. It was late at night now though and the pool would be deserted, if it wasn’t closed.
Kevin got out in the elevator and pushed the button for the lobby. He waited impatiently as the elevator doors slowly closed and he began to dip down. He wasn’t surprised when the elevator doors opened to an empty lobby. He walked confidently out of the elevator and made his way to the glass doors that led to the outdoor swimming pool. As I’ve previously said though, he was very drunk, so his confident walking resembled what some might call a drunken stumble.
He collided with those glass doors a bit harder than he had anticipated but they did not give way. They were in fact locked, which probably meant the pool was supposed to be closed. He wasn’t worried about that though. A few days ago, while he was sober, he had noticed that there was a pile of dirt along the wall that encased the pool. If he were to climb on that pile of dirt than getting over the perimeter wall would be just a quick hop away. He loved when sober him thought ahead for drunk him.
He turned around to go out the front door of the hotel so he could find that dirt pile that was going to double as his stepping stool when the elevator doors opened again and a stunningly hot girl walked out. Due to the fact that Kevin was drunk, he was only able to take in certain things about her appearance, mostly her very substantial breasts whose nipples were poking through the grey concert Tshirt she was wearing. But he also noticed her incredibly toned and tanned legs which her denim short shorts were showing off.
She looked in the direction of Kevin and said, “Fuck, is the pool closed?” Kevin was still staring at her legs which seemed to go on for days.
“Ahh, yeah its locked.” He answered trying to seem like he hadn’t just been checking her out and trying to come off less drunk than he was, the bottle of rum in his hand really gave him away though.
“Shit, I was really looking forward to taking a late night dip.” The way that this girl said the word dip made Kevin’s shorts tingle a little.
“I actually think there’s a spot where you can jump over that wall. I was going to go try to do that if you want to come with.” It was a total shot in the dark, but why shouldn’t he at least try to be a gentleman and help this girl get her late night dip.
“Really?” she said, “That sounds great.”
“Yeah, alright. Follow me then.” Kevin walked through the lobby and out the front door with this smoke show on his side.
He turned right and headed for the pool’s wall when she asked, “Can I get a sip of that rum?” Kevin handed the bottle over. She took the cover off and downed a large swig before shuddering a bit as the alcohol went down her throat. “Ahh thanks.” She handed the bottle back to Kevin who took a sip of his own. “I’m here with my parents and little brother, I’ve wanted a drink so bad but it would be really awkward to drink around them.”
“That sucks.” Kevin said, not really knowing what to say but talking anyways, “Are they like not into drinking?” He passes the bottle back to her.
“Exactly.” She says after taking another sip, this one is longer than the first, her mouth wraps around the neck of the bottle as the rum pours into her mouth, a little trickle spills down her chin and stains her tshirt as she takes her mouth off the bottle. “They never drink so it would be weird if I was just drinking around them.”
“I know what you mean. I’m here with a couple friends so I’ve done nothing but drink the whole time pretty much.” Kevin says, they are getting close to the dirt pile that he plans to use to get over the wall.
“Really? That sounds awesome!” the girl says excited.
“It really is. Tomorrows our last day though, you should come out with us.” Kevin offers.
“That sounds so much better than going to the beach or whatever I’d be doing with my family.”
Kevin stopped in front of the dirt pile. “What do you think?” he asks, “climb the dirt, then jump over the wall?”
The girl is sizing up the dirt pile and looking at the distance between it and the wall “I don’t know if I can make that. Will you give me a boost if I need it?”
“Of course.” Kevin replies taking a sip from the half full bottle.
The girl takes a sip of her own and then climbs up the dirt. The dirt is loose and she slides down after her first few steps up. She goes on her hands and knees the next time to get more traction. While this position made it a lot easier to climb the dirt it also made her ass pop right in Kevin’s face. He couldn’t help but stare, he hadn’t noticed just how nice her ass really was before now. It seemed to eclipse the rest of her from his view so that all he could see of this beautiful girl was her denim covered ass. While I say that it was denim covered that might be a bit of an exaggeration. The denim short shorts that she was wearing had been covering very little in the first place, now that she was bent over like this the bottom of both cheeks were showing out of the legs of the shorts while the rest of her large firm cheeks were fighting against the fabric for their own freedom. It was an incredible sight to behold as the shorts battled with their captive. Kevin was so transfixed with what was in front of him that it took him a second to realize that she was asking for help.
“Give me a little shove.” She asked in a quiet tone as she began to slip back down the dirt. Kevin didn’t see much else to shove except the glorious ass that he had just been admiring, so with very little hesitation he put a hand on each cheek and gave a shove to help her along. He was startled by how firm her ass was considering how big it was. The skin only gave way the slightest amount to his touch as he put his hands on her. Kevin could have spent hours playing around with her ass, touching it, squeezing it, bouncing things off it to see really just how firm it was, but his time with it for now only lasted a second and then the beautiful girl and her wonderful ass were on top of the dirt pile.
“Thanks. I’m going to try and get over the wall now.” The girl said as she steadied herself on the dirt pile. She made quite the athletic dive at the wall but didn’t clear it, instead she was stuck holding onto the top of the wall. She tried to use her long legs to finish climbing up the wall but she only succeeded in keeping herself where she was. “Help again?” she asked.
Kevin was happy to get another chance to touch this beautiful girl. This time he went underneath her lovely legs, they hung down to about his rib cage, he considered trying to give her ten fingers up on one of her feet but that wasn’t nearly as fun. “Hurry up.” She called from her place at the top of the wall, “I have to pee.” Kevin briefly considered leaving her hanging where she was and letting her pee on top of him, then he reminded himself that he was trying to be a gentleman and a gentleman would not do something like that. So instead he put one hand under her that firm ass of hers and another hand on her denim covered crotch and pushed upwards. She gave a little squirm when his hand first touched her crotch but before anything more could come from the touch she was up and over the wall. She didn’t make it over before Kevin realized that her jean shorts were a little damp in that warm area of her crotch. Then it was Kevin’s turn to climb the dirt pile and wall. He didn’t find it nearly as difficult as his companion had, but the bottle of rum in his hand and the half chub in his own shorts had not made things any easier.
When Kevin got over the wall he saw the girl undressing for her dip in the pool. He made it over just in time to see her t-shirt come off. As the shirt went up over her head and covered her eyes her breasts were revealed to him in all their wonderful glory. They weren’t obnoxiously huge boobs like some guys were into, but she was by no means flat chested. The nipples that stood out on each breast looked perfectly delicious and he wanted nothing more than to rub his tongue around each one. Her chest showed no tan line at all, which he took to mean that she spent a lot of time outdoors without cloths. When her shirt was off she turned around and slowly shimmied her shorts down. She shook her ass back and forth as she tugged them down to reveal her incredibly tanned ass cheeks which had all but swallowed up the white panties that she was wearing underneath the shorts. When she had the shorts down to her knees she spread her legs, bent over, and looked at Kevin from between her open legs. She had caught him staring with awe at the sight before him but didn’t seem to mind. She laughed at his expression, tugged her underwear up more to increase the wedgy, then dropped her shorts to the ground and dove in the pool. Kevin could not get his own shirt and shorts off fast enough before diving in the pool in his boxers.
The two of them swam around each other for a while, occasionally they rubbed against each other. Kevin got to feel the snap back of one of her nipples when it was bent away from center by a casual finger in the water and she let a hand slide against the tent in his boxers.
After playing this game for a while in the silent swimming pool they made their way to the shallow end where they sat close to each other and occasionally took sips from the bottle of rum as they talked.
“What’s the craziest thing you’ve ever done?” She asked Kevin as he casually brought a hand up to her boob and squeezed it gently to see just how nice they really were. It was just soft enough, it wasn’t as soft as a pillow like some girls he had been with. Her boobs were more likely to keep him up at night than be his pillow. He could imagine that holding on to them while he fucked her from all sorts of angles would make for a great time.
“Well when I graduated from High School I did a back flip off a bridge.” Kevin answered her question.
She looked disappointed, “No, I meant like… crazy sexually.” She amended.
“Ooh, that’s harder.” Kevin thought for a second before saying, “Well like a semester or two ago I had an English class in this really big lecture hall and it was pretty filled with students. So, one day I sat next to this girl in the back of the hall. I don’t think there was anyone directly next to either of us but there were definitely people right in front of us and then there were other people in the back row too. But she starts making these noises, she was like moaning and stuff. I honestly didn’t know what was happening so I leaned over and asked her if she was alright. She looked at me and asked, ‘will you help me?’. I told her I would and then like immediately she grabbed my hand with hers, which was all wet and shit, and she brings my hand right up the skirt she was wearing, she already had her underwear pushed aside and she was just fingering herself right there in class without anyone noticing. So, then I like took over and started just fingering her right there. I was doing really fucking good too, like I was hitting her clit and it got really wet really fast. She came two or three times and by the end of it all you could hear was this.” Kevin paused to slap the pool water very fast to replicate the sound. The girl doubled over laughing as he finished his story. “So, there’s no way that anyone around us didn’t know what was going down by the time the class was finished. I got like a couple dirty looks from the people in front of us but then there were a couple girls who like sat right next to me the next few days.”
“That’s awesome. You sound like you’re really good.” She said rubbing her foot against his.
“I like to think I know how to show a girl a good time.” He replied feeling as cool as that sounded.
“I’d like to have a good time.” The beautiful girl said turning towards him so that her nipples rubbed against his arm.
“I suppose I can try and help you out.” Kevin said slowly reaching a hand down her white underwear which had become transparent the second she had got in the water. Kevin could clearly see a narrow landing strip right above the lips of her pussy. “What’s the craziest thing you’ve ever done?” He asked as his hand got its bearings in this unexplored territory.
“Umm, okay well I work in this kitchen on campus at my college,” she began giving a little wiggle and spreading her legs a bit more so he could have better access to her, “and when I first started I was in charge of washing dishes. That’s like the new person’s job. So, I got stuck in this small room with a big sink, an old like industrial dishwasher, and just an absolute fuck ton of dirty dishes. And I just spent hours in that room cleaning dishes by myself because people would just send the dishes in on a conveyer belt, so no one ever even came in the room. So, one day I was just in there cleaning the dishes—oh wow that feels good.” She broke from her story as Kevin went particularly fast on her warm little clit, chasing it around with two of his fingers as it moved slightly from side to side. She panted once then tried to resume the story as Kevin eased up a bit. “but, so, the dishwasher would always shake a ton when it was going. Then one day I like hadn’t been laid in forever and I really just wanted to get off, so I turned on the dish washer and then just stood at the corner with my pussy right up against it as it vibrated and shook all around. It felt so good. It makes a ton of noise too which was lucky because I was basically screaming it felt so—gooood.” Kevin had once again increased his intensity on her clit and she had squirmed to the side when he did so. “Holy shit that’s good. But I actually squirted all over the place. Well like I had my pants on still so it was just all over my pants. I was soaked, it looked like I pissed myself. When I got off, haha, get it? But like when my shift was over and I came out of the room my manager asked me what happened and I just told him that I had splashed myself with the sink and then I walked around in squirt pants for the rest of the day.”
As she finished her story Kevin increased his finger’s movement on her clit to a very rapid pace. She bit her lip and threw back her head as she bucked her hips against his hand. “You’re really good” she whispered in between gasps as he continuously rubbed her clit. Her sighs, groans, and moans grew louder and louder as he worked her towards a climax. Kevin was glad it was so late at night otherwise passersby on the street would have been seriously concerned by what was happening in the pool. Kevin increased his speed even more, his hand was now slapping back and forth between her lovely thighs as he rubbed her slippery clit. She squeezed his leg and let out a loud moan as she came hard. As she eased back he slowed his hand down and moved it from her clit to just outside her vagina, with one finger he slowly traced circles around the entrance. Even in the pool water he could feel how wet he had made her.
“Stay there.” She told him as she moved so that she was now sitting on his lap, still under water. He could feel his dick rubbing against her practically bear ass. The only thing that was separating skin from skin was his wet boxers and the underwear that was still mostly swallowed by her ass. With his free hand he slowly eased his dick so that it was poking out the hole in his boxers. Kevin let his dick gently rub up and down the crack of her ass as she sat on his lap while his other hand did gentle circles around her vagina.
She turned her head so she could whisper in his ear, “Guess what.”
“What?” Kevin asked back in the most seductive whisper he could.
“I still have to pee.” She giggled. Just then Kevin felt a current of warm water pass over his hand which was still down in her underwear. The warm piss that streamed from her felt nice on his hand as it mixed with the water of the pool. As she was still peeing she turned around in the water so that she was facing towards Kevin. Kevin had not moved his hand from her crotch and he continued to let the pee flow around his hand as he worked his fingers inside her. Kevin seized the opportunity of being face to face with her boobs and used his free hand to cup one while he brushed his tongue along the nipple of the other. It didn’t take long in this new position for Kevin to realize that his dick was now getting the benefit of the warmer water. When he realized this he moved his hand out of the way and let her warm piss water flow over his throbbing hard dick. It felt so good and so dirty and it drove him wild.
When she finally stopped peeing she lowered her head to his shoulder and whispered again, “So are you going to fuck me or what?”. Kevin didn’t hesitate. He slid her white, piss washed panties to the side and then put his cock inside her very wet pussy. She used her long legs on the bottom of the pool to bounce up and down. After only a few seconds of this Kevin began to let himself slide down a bit as she thrust up and then as she came down he drove himself up so that he was making powerful thrusts underwater. Each time that she came down on the full length of his dick she let out a little gasp and he groaned with pleasure as his dick was encased in her wet pussy. Her boobs made waves as they slapped against the water’s surface each time she came down.
Kevin could only keep up large thrusts like these for so long, so he said with a fair amount of urgency in his voice, “I’m gonna cum.”
“Yeah?” She asked driving down her hips once more on his dick, which really was ready to burst with cum.
“Yeah.” He panted doing everything he could to hold out until she got off him.
“Watch this.” She whispered before lifting herself completely off his dick and then diving down under the water. It was only a second before he felt her mouth close around his dick and then only another second before he began cumming. He moved a little in the water as the waves of his orgasm hit him but her mouth stayed fully clasped on him the whole time. When he was done her head broke the surface of the water and he could see no trace of his cum in her mouth. He assumed she swallowed it but couldn’t be sure. They moved farther up in the shallow end and laid there with the water covering about half their bodies.
Kevin woke up the next morning with the sun in his eyes. He was still in the shallow end of the hotel swimming pool wearing only his boxers. The girl was gone, so was his bottle of rum. It was a small price to pay for such a wild night of swimming. Kevin threw on his cloths which were still where he had thrown them last night as he hastily undressed and made his way back over the wall and to his hotel room with one hell of a story to tell his friends.

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