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.”