The first time I saw Kate Upton on my Costa Rican vacation was when I first checked in. I was signing a form at the front desk of the hotel – and I would have handed the pen back to the clerk if she didn’t show up.
“Oh, sorry!” she spoke, once she realized she was technically cutting in front of me. “It’s okay, I can wait.” However, once I saw her in her white t-shirt and shorts – both of which were fairly low cut – I knew it’d be a while before I actually did something.
At least until I dropped the pen on the ground. But that resulted in Kate bending down in front of me – in that low cut t-shirt – so no harm done. Then again, that might change if I didn’t move anytime soon.
I recovered enough to finish signing my form, then stepped aside before I knew any better. By the time Kate thanked me and started talking to the clerk, I knew my window of opportunity to do more than drool at her had shut.
At least until the second time I saw Kate Upton.
After the first time, I really needed to check in, relax and get lots of ice — for various reasons. When I ran out of the first batch, I went to the nearest ice machine. It turned out Kate found her way there five seconds later.
“Oh, you’re kidding!” she beat me to saying. At least she sounded more amazed than annoyed. That was enough to make me say a few words.
“All right, you go ahead of me this time,” I offered, taking away my half full ice bucket. “We’ll call it even.” Right – the ideal first words to say to the hottest and most busty model in North America.
Well, the smile she gave me told me it was.
Kate filled up her bucket, taking it away right before a few spare ice cubes came out. “I got it,” I sprang up, loving the irony of picking something up for her this time.
Bending down to pick up ice cubes didn’t give her a view of anything….special. I could only see her bare legs from this angle, which still wasn’t too bad. In any case, I dropped those spare pieces of ice into her bucket without a problem.
“Thanks. Now we really are even,” Kate quipped. I chuckled, although now I actually had to say parting words this time.
“Cool. Till the next line we’re in, then,” I spouted out, turning red on the inside if nowhere else. Kate still laughed and nodded, so I took that as my cue to leave while I was ahead. Needless to say, I paid a few more visits to the ice machine that day.
The next day was encounter No. 3, which was even less planned than the first two. I was walking down the beach early in the morning, enjoying the scenery and getting my mind off the….scenery I dreamed about last night.
Which would have been easy, if I didn’t stop in front of the side of a hill, look over and see that scenery posing on the beach.
I had walked far enough to stumble my way near a beachside photo shoot. Well, what else would Kate Upton be doing there? Still, I imagined seeing it in person was different from seeing the end result in a magazine. Even if there wasn’t as much privacy here – and even if I was too far away to see much of anything.
From what I could make out, the little bitty material over her chest and ass was red. It got easier to see when she got up and went over to the water. Once she was ankle deep inside, she went on her knees and even stayed in position when the tiny waves crashed into her back, right as the pictures snapped.
If I didn’t leave after seeing that, I would never have the strength. Then the yelling, arrest for trespassing and restraining orders would likely come. That would sure be some vacation.
This one calmed down a little when I got back to the lobby. I did need a nap after getting up early, walking around so much this morning – and being so busy in my dreams. However, I didn’t remember anything from the dreams I had in the lobby.
Which was just as well, considering who woke me.
“Why the hell?” I reacted, before remembering I was making a scene in a hotel lobby with Kate Upton. She was now in a flowery sundress instead of a red two piece, which only helped a little.
“Probably because you had a long night. Or an early morning,” Kate told me.
“Oh. Um, what makes you think that?” I feared I’d live to regret asking.
“I had a photo shoot on the beach today. For a minute, I thought I saw someone watching me. Someone who wasn’t from the crew,” Kate shared. “I thought I saw something on his shirt, though. Kind of looked like….that thing.”
Kate pointed to the Philadelphia Eagles logo on my shirt. It appeared they could even ruin my life in another country too. “Oh….odd,” was all I had. “There wasn’t anything more….pervy about him, right? I mean, if he left right away, he couldn’t have been that bad.”
“I caught him just before he left. For all I know, he could have been stalking me all morning,” Kate proposed.
“Or walked too far on a morning stroll by accident. That’s….plausible,” I cringed, knowing full well it wasn’t, despite being the truth.
“Well, the shoot did go well. And I keep running into this guy for some reason. So I’m in a good enough mood to take a leap of faith,” Kate said, giving me a few leaps as well.
“Oh. Okay, that sounds wise. And accurate. I mean, I’m sure the shoot did go well. At least five minutes of it,” I brought myself to admit.
“Thanks. Just keep it between us, until the pictures are ready for the Internet. Okay?” Kate asked.
“Done and done,” I began to relax.
It got more relaxing with the more time Kate stuck around, which I didn’t expect – more because of me than her. Nevertheless, she talked a bit about her shoot, how she was staying for an extra day, and other upcoming projects. But she didn’t just talk about herself, as she let me get in words about how I was just taking a normal vacation. Of course, it was hardly normal now.
Sadly, Kate soon got called away on business. Yet given our luck, I was less certain that we wouldn’t run into each other again. She said she hoped so, although since she was just getting into acting, who knows if she was saying that as an exercise.
Still, her eyes looked truthful – or maybe they were too blue and sexy, and better to get caught looking at than her giant tits. Either way, I felt convinced. Plus the kiss she gave me on the cheek before going away helped.
Improbably, I was able to make my way back to my room. After resting and doing other stuff in bed, I was tempted to just walk around and wait to see Kate again. At the least, I could ask for her room number, in case I had big enough balls to come to her.
But they were drained before long, and not in the fun way. I didn’t see her the rest of the day, or night for that matter. I still had one more day before she left, but maybe I’d used my spare supply of luck in getting away with spying.
Resigning myself to a sleepless night either way, I put on a t-shirt and trunks and went out for a midnight walk. I confined myself to walking around the hotel grounds, passing by the outdoor in ground pools. There weren’t hundreds of people splashing around to loud music, so everything was peaceful.
Enough for me to hear some lower splashing sounds, anyway.
There weren’t many lights on near the pools, but I could swear I saw a silhouette swimming around. Sneaking for a closer look, I began to develop a crazy theory in my head. Then again, maybe it wasn’t so crazy after these last two days.
Nope. It was just crazy enough.
“Oh, God!” Kate Upton gasped when she saw me near the edge of the pool. Yet when she made me out, she sighed in relief. “Oh, God, good….”
“Good? What are you….” I cursed myself for lack of tact again. Recovering, I asked, “They allow you to swim out here this late?”
“I didn’t technically ask,” Kate answered. “Besides, I spent enough time in ocean water today. I wouldn’t have been able to enjoy this water in the afternoon.”
“I see where you could see that,” I conceded, knowing she couldn’t have gotten this peaceful swim hours ago. Even if she wasn’t Kate Upton. And even if she wasn’t in a blue, wet two piece covering her pink, wet….or barely covering….you know.
“I am a swimsuit model, you know. Should be able to swim every once in a while,” Kate reasoned, pushing herself off the wall to swim backwards – with her chest surely sticking out of the water. Now I was grateful it wasn’t too light out.
“That’s very reasonable,” I told her. “I should let you get on with it.”
“Why? We’ll probably just wind up here tomorrow anyway,” Kate figured. “So let’s get on with it. Come on in.”
Well, by some miracle, I was dressed for it. I gave myself credit for not putting on formal wear for a midnight walk, then removed my shirt and made my way into the water. The starlight and the sparse artificial light helped me see Kate better – even when I went underwater.
Yet at that point, I really wished I brought goggles, so I could see Kate underwater without getting chlorine in my eyes. Fortunately, Kate had a towel near the edge of the pool, so I borrowed it to wipe my eyes clear. After that, I was content to just swim around and float around with Kate for a while.
Of course, when Kate floated, her chest was large and wet enough to keep her up. I hoped it was too dark for her to see me….checking up on her. But she made no comment – and besides, she couldn’t well scream at me and wake people up for me being a pervert. She might save that for when we get back inside.
Yet until then, she seemed pleased with my company. We even went on our knees in the shallow end – in a clean way – just looking up at the sky while being mostly submerged in the water.
“You don’t get to do this during shoots,” Kate commented. “Or anywhere, really. Not if you’re me.”
“Now I can see how that would suck,” I responded. “Sorry.”
“It’s all right. After a busy day, you take whatever peace you can get,” Kate noted. “This is a good get. Floating in the water, all nice and quiet, where no one can see you….except the guy you’re with….I’ll take that any day.”
“Sounds promising,” I said, in lue of stammering or letting my brain overheat. There was certainly nothing I could do to keep my cock from twitching in my trunks. So this was better than nothing.
Not better than other things I probably….shouldn’t be thinking of. But still.
“It helps that I’m extra sensitive in the water,” Kate went on. “And when I get out. It feels so good to….relax after a swim, or a shower, or anything where you get real wet. I bet you understand that.”
Actually, I did. Post shower jacking off was the best kind of jacking off, after all. Before that threw me off, Kate added, “And I know it feels just as relaxing in the water too.”
Fuck me, she….okay, I needed room to breathe.
By the time I got on my feet and stood up against the nearest wall, I could see how I was being an idiot. Still, if Kate fucking Upton was alluding to fucking…..well, I needed to be in the right state of mind for that.
And any hope of that vanished when I saw her walking to me, with the naked top of her breasts above the water. However, she stopped when she got a few feet in front of me – maybe she came to her senses, or I just looked too nervous.
“Come on, don’t get shy on me,” Kate actually teased.
“Not the problem here, trust me,” I admitted as clear as I could. The involuntary glance down at the water – a big help in hiding my big erection – cleared it up more.
If I misinterpreted everything, Kate could have really slapped me. Instead, she actually slapped the water and splashed me with it. Not that cold water would help me now.
After she giggled, my anxieties went away a little. “So that’s the game?” I let out, sending a little water into her face myself. Kate was undeterred, going forward and sending water my way again, then I did the same. Before I could beat her to doing it again, she got my wrist just in time.
When she got my wrist, she could push herself against me. She could press her body against mine. And I could do nothing else but kiss her – then neither could she.
With the switch on, our lips and tongue went fast and furious, yet Kate slowed down first. Before long, I was sandwiched between Kate and the wall, although Kate was the one giving me seductive kisses and trailed her hand down my chest. And down to other places.
I knew Kate wasn’t kidding when she said this sort of thing felt better in water. But having her hand brush against my cock in water was off the charts. Unfortunately, if I came in the water, I probably couldn’t hide it.
However, Kate just gave me a few more kisses and brushes before backing away from me. Before I knew what was happening, she was swimming over to the steps. In a panic, I swam after her, only to realize halfway through that she wasn’t getting out.
Kate was lying on her left hip at the steps, which couldn’t have been that comfortable – but she still oozed seduction anyway. Running as fast as I could through water, I sat on the steps next to her. At that point, she wasted no time in getting herself on top of me.
This wasn’t the most comfy position for me – at least below me. On top, Kate’s wet body lying on mine – and her wet breasts lying on my chest – felt pretty okay. So did her lips attacking mine again, and then going to my neck next.
Yet it all paled to when her hand actually got into my boxers. It didn’t take much effort for Kate to pull my cock out, all as her tongue went down to my chest. It finally made me take my eyes off her own chest, as her hand work, tongue work and sultry blue eyes captured me for the moment.
I had to sit up and try to relax, so I went up a step – leaving my cock exposed when I sat back down. This was perfect for Kate, who settled down beneath me, took her wet hand out of the water and started pumping me.
God, to think I thought my own hand felt great down there after a shower. This….fuck.
Which is what Kate’s mouth started to do to my cock in short order.
My groans were caught in my throat, which was just as well. Otherwise I might have woken up the entire hotel.
Nope – I really almost did that when Kate removed her bikini.
I only saw Kate’s bare tits for a moment, before they went back in the water once she sucked my dick again. It was the only time a Kate Upton blowjob could possibly be disappointing. But when her tongue worked on my head, I figured I could live with it.
Not cumming from it might have been too much. Yet I held as Kate pumped me, put more water on me and sucked my sensitive shaft down. “Okay, I think you’re ready….” I vaguely heard Kate say, then she left my cock bare.
At least until she lifted her tits up.
I could only admire them for a second again, before Kate smothered them on my cock. I felt like I was gonna choke from holding my moans back, yet I willed myself to live a few moments longer. My reward was to see that her soaked, mammoth breasts fucking my cock did look as unreal as it felt.
She didn’t have to smirk and burn a hole into me with those seductive eyes of hers too. She didn’t have to bend down and lick my head either. But Kate did those things too. In return, I pumped my hips forward, hoping to do some of the tit fucking myself while I could.
“Uh huh, yeah, come on,” Kate breathed so quietly and so hotly on my head. After the tip of her tongue teased my tip, I couldn’t defy her any longer.
It took a few more pumps first, but Kate finally took her tits off and put her mouth on me. I had just enough to reach forward and grab her tits – which pretty much turned the on switch on for my shaft.
Kate sucked down every drop that came out of me. It was the sanitary thing to do, since more people would be swimming in here tomorrow. Still, we probably crossed the sanitary line already – but with me cumming in Kate’s mouth while squeezing her tits in water, I had other things to think of.
Nevertheless, my brain was virtually off by the time my cock stopped working. Kate had more sense to come off by then. “Perfect,” Kate praised – then swam away before I could respond.
Okay, that part wasn’t perfect. That wasn’t all she was gonna give me, was she? I mean, this was already the time of my life – but I wanted to be one of the top…..10 or 20 of hers. And I had a lot I could do to do it!
Once my blood went back to my bigger brain, I slipped my trunks completely off and swam after her to prove it.
Kate was just swimming around topless, but went and stood against the wall when she saw me coming. I looked down at her mostly exposed chest, looked back up at her face, then waited for any sign of approval.
All she did was slide over closer to the shallow end – where she could stand while her entire wet chest was exposed. Now I didn’t have to swallow any water while I swallowed her mounds. Good thinking on her part.
I did the best thinking of my life when I went over to Kate and bent my head down. My hands pushed her tits up and gave me extra help too.
My fingers worked themselves to the bones rubbing, squeezing and massaging Kate’s soaked puppies. My tongue worked less fast in teasing and batting her nipples around, but my teeth helped make up for it. Soon, the rest of my mouth joined in.
As much as I could have squeezed her chest all night, I needed one hand free for the next step. I let my left hand take the hit and go underwater, while my right did all the tit groping. However, when my left hand reached Kate’s crotch and bikini bottoms – the only piece of clothing still on either of us – it got back in the groping spirit.
Of course, given how Kate was standing underwater, she was wet well before I rubbed her nub. Still, I was at least going to cheat well. It sounded like she approved when I pulled down her last bit of clothing, took her with my forefinger and thumb, and sucked down and pushed up her right tit at the same time.
“Oh yeah….oh, make me wetter,” Kate asked, and I complied by putting my forefinger in her. After a few more suckles on her nipple, I reluctantly stopped and went up to her neck. But I kissed and nibbled it while holding her tit and finger-fucking her pussy all at once, so neither of us complained.
“Fuck, fuck baby….ooh, work that pussy and that tittie….” Kate kept hoping. However, I needed extra help working her pussy.
After a few final love bites on her neck, I backed away slightly from Kate. This gave me room to reach down and put both hands underwater, and on her pussy. Now both sets of fingers were working on her. which made her arch her back and moan – perfect enough for me to bend my head down and work her chest again.
This time I paid attention to her neglected left breast, suckling and kissing it and pulling her nipple with my teeth. Once I suckled it all better, I went back and forth putting my left and right forefingers in her, then my left and right thumbs. “Oh, fuck me….God, I’m gonna fuck you….” Kate promised.
Her idea of keeping her promise was to grab her own tits, then rub them up and down my face. She groped them and rubbed them against me, as all I had to do was lick between them and shake my head.
Kate tried to tit fuck my head like she did with my cock, while her hips thrust up against my fingers. When I went lower to lick and suckle the undersides of her breasts, she had enough. “Fuck, that’s it! I need your tongue to finish me off….” she insisted.
Unfortunately, that required swimming away from me and heading for the steps. I was pretty disappointed, until I saw Kate walking on the ground, naked and dripping. Still, it would have been better to see it with more light on her.
Nevertheless, she was going over to her chair and towel – mainly to the towel. She came back and stood on the edge of the pool, laid the towel down on the ground, then sat on the towel. Otherwise, she was sitting up in front of me, right on the edge with her legs all open and willing.
Although I could eat her out now, I went back to using my fingers on her. After a few seconds, however, I put them back in the water before putting them back between Kate’s legs – then I leaned forward to lick the already wet center.
I had to hold onto the top of her legs to keep my balance, as my head and mouth buried themselves into Kate. When I came off to catch my breath, I put my hands back underwater, then lifted them up and reached around Kate to hold her ass. Once they held onto her drenched backside, I dove back into her drenched center.
Kate moaned and put both her hands on the back of my head, all as her hips thrust forward. “Oh fucking God….you can hold your breath down there too,” Kate commented, gyrating her hips now. I squeezed her ass harder as my tongue burrowed deeper, which made her go, “Fuck, shit! Okay….just one more thing before I go….”
Kate removed her hands from my head and backed away, making me let go of her ass. However, she then laid down on her stomach and presented it to me, her ass lying on the edge of the pool and her legs hanging in the water.
Now that I could eat her out from behind, I put my hands back on her ass and soaked it anew, right as my tongue went back on her pussy. Kate bucked her hips back while I squeezed her and tongue fucked her, though she went faster when my teeth got involved.
“You ready?” I asked. “You gonna cum here so it doesn’t get in the pool?”
“Just make me cum first,” Kate wanted. It helped that I wanted it too.
And when my left forefinger got into her, my tongue licked beside it and my right hand jiggled and lightly spanked her dripping ass, we got what we both wanted.
My mouth opened wide to catch her juices, so none of them dripped into the pool. Kate muffled her moans, reminding me we were still in a public, albeit closed, area. However, I was going to drink her all down before we got caught.
No one came to interrupt us as Kate finished cumming, though. I lapped her up and got her dry – of cum, anyway – in relative peace and solitude. After I was done, I ran my hands up and down Kate’s legs before she finally turned over.
I swam backwards to give Kate room, in case she was coming back in. She stayed seated on her towel, rubbing herself briefly and getting her bearings straight again. Whether they were straight enough to finally get her away from me, I could only wait and see.
After a half-eternity passed, Kate got up on her two feet. She walked away, which didn’t bode well – but she was walking to the edge of the deep end. There, she stepped back and promptly dove right back in the water.
I made my way back there by the time Kate’s head came back up. “Just what I needed to warm back up,” Kate said, seemingly more to herself than me. Once she saw me again, she swam around me for a little bit – brushing her hand over my erection after the second pass.
“Very nice,” Kate approved, backing me up against another wall. This time, only our heads were above water. However, Kate still teasingly traced her fingers on my shaft – and although I couldn’t see her tits, I could still feel them underwater. It wasn’t much of a step down.
“We could just go to a more comfortable….dry place for this,” I offered, since this logistically might not be the best place to….be thorough.
“I’ve still got a day left here,” Kate answered perfectly.
“Okay….you sure you’re set?” I made sure, in case I did too good a job on her. That was it.
Before she gave a final answer, though, I lightly brushed my fingers between her legs as well, then took another two handed squeeze on her chest. “Close enough,” Kate promised.
She reached up and put her hands on the ground, holding on while she lifted her legs up and wrapped them around me. All I could do was try to keep standing as Kate lined herself up on me. But I still used my hands to keep my cock steady, as Kate began taking me in.
My hands then went to her waist, giving me something to hold onto as well. Hopefully that wasn’t all I could do in this position. Kate could conceivably do much of the work, yet I had to be good for something else. Still, being halfway buried into her felt good at this moment.
After a few thrusts helped me get completely in, it really sunk in – as much as Kate was. I watched in amazement as Kate’s busty supermodel body rode me underwater, while her sultry, sexy face and wet blonde hair shone under the night sky.
I said many times in my head tonight that I couldn’t fucking believe this. Now I almost said it out loud. Kissing her stopped me from going that far, though. Luckily for me, Kate kept it going and squashed the danger for good.
Our tongues glided together as my hands slid just as effortlessly up and down her body. When they got down to her ass, I tried my hand at giving it a little slap under the water. In response, Kate put her left hand underwater and slid it down my chest, then reached lower and nearly got my balls.
Once she brushed a finger on them, I was able to set the pace for a while. Kate put her other hand down and grabbed my shoulders, but after another few moments, I couldn’t really stand up as well. Sadly, we had to break off and find a more comfortable position to keep going.
One such position came to me when we got to the halfway point of the pool. I could stand behind Kate, which inspired me to wrap my arms around her waist so she could stand still. I lined myself up and managed to find my way right back in – fucking her from behind as we stood in the middle of the water.
With Kate’s head arched back and her tits popping up from the water again, I laid my head on her shoulder and watched myself grab them again. I could have watched that the whole time, but there was too much else to enjoy. Such as running my lips and tongue over Kate’s long, wet neck.
“Oh, how sweet of you….” Kate teased, before adding some sweetness of her own. If that’s what she called putting her hand down to get a much better grasp on my balls. It’s what I called taking my right hand off her chest and settling it on her filled pussy, at least.
With my grip on her right tit and pussy, my cock fucking her faster and my hips colliding onto her ass, it was a wonder Kate could still stand up. This position probably wasn’t a long term solution either. With time likely of the essence, I figured we should both be comfortable.
After a few final squeezes, flicks and pumps, I made myself pull out of Kate while I had the willpower. Stepping out from behind her, I took her hand and led up back to the steps. Stopping and sitting at the third step from the top, I waited only a few seconds for Kate to get the idea and sit back on my lap.
Much of our bodies were out of the water now – which admittedly made me a little cold after all this time. Nevertheless, I could see just how dripping Kate was – all over – as she settled back onto me.
Her tits resumed bouncing and all but splashed more water drops on me, her ass was rising in and out of the water, and her pussy looked nice, clear and full down there. My left fingers helped it out this time, all while my right hand went on her hip and my face dropped back on her chest.
After putting my left hand on Kate’s other hip, she felt safe enough to take her breasts and slide them up and down my face again. I tried to hold her upright while her hands were occupied – my face certainly wasn’t going anywhere.
It did finally turn to try and devour her soaked left tit, then did the same to her right. But that was about it.
“Oh, there you go, baby,” Kate declared after letting go of her breasts. “I’m gonna cum all over you and in the water….you want that?”
“You should probably just get it on me….” I commented.
“You help me out, I will….” Kate insisted, as if I wasn’t trying already. But if I had time for a few more tricks….
The best one I had left was putting my left fingers against Kate’s pussy. This was followed by my right hand grabbing her ass, so my fingers could tickle the other side of her pussy. Combined with my mouth suckling down what I could on her right breast, I hoped it was getting her there.
Kate’s moans and bucking gave me a good idea.
“Fuck….fucking soak me!” Kate kept encouraging, putting her arms around my shoulders to hold on. Since she was secure, I could stroke the front and back ends of her groin harder, while fucking her middle faster.
Somehow, I had enough energy to give quick suckles back and forth on her tits too. Yet as I felt Kate tightening and getting close, I settled for burying my face in her neck and nibbling her collarbone as a final trigger.
“Ooh, yes! Cum for me when I cum for you….” Kate got out before she could only groan. My own groans went right on her neck, which I hoped helped. Either way, she was still a goner.
Not long after she started going, so did I. Water and protection and potential cum leaking be damned.
I finally leaned back as our orgasms washed through, my head barely avoided hitting the ground. Kate laid on top of me, high and kind of dry, as she released on me and I shot into her. We had no way of knowing if our juices were in the public water by now – but getting them out seemed more important right now.
When they finally got drained out and in, we could start breathing. My hands rested on Kate’s back, as her chest rested onto mine. This was one of the few moments where that couldn’t affect me in the slightest.
After I felt like I could be affected by anything again, I absent mindedly rubbed Kate’s back. I even put more water on it to help snap her back into action. Ultimately, she rolled off and sat down next to me, giving both of us room to recover and move around.
Kate got herself back into the water, content to just hang and float around. With nothing better to do now, I got back in as well, wandering around in the likely dirty water.
Looking up at the sky distracted me from that fact, as well as other uncomfortable facts – and uncertain short term futures. But then I saw Kate looking up too. Yet another odd coincidence between us in this place.
This gave me the courage to bring up, “You said something about….a day left to see dry places?”
“Later. Once the day starts,” Kate had me there, since it was nowhere near light out. I saw no reason to mind, though.
“Later,” I repeated, taking a few final moments to swim and float around, with the swimsuit model of everyone’s dreams.
