Night 0 (vs. the Stakes)

“Bow before me, your Queen of Bear Creek!”

I rolled my eyes at Becky’s pronouncement, made while perched atop her boyfriend (and my best friend) Chuck’s shoulders. The blonde held her arms wide as if accepting the applause of a crowd, one that didn’t exist.

“Sorry,” I muttered to Eve, my partner in our losing effort at playing chicken in Becky’s backyard pool. Unlike the other two, and much to my chagrin, we weren’t a couple. The four of us had grown up together in the small neighborhood of Bear Creek, attending the same schools and sitting in a group on the bus twice a day for a decade. I’d crushed on both girls over most of our high school years. Circumstance and fear of messing up a good friendship had prevented me from ever asking Eve out, even after Chuck and Becky broke through that unspoken barrier.

“Don’t worry,” Eve said, clearly not too bothered. She ran her hands through her brunette bob to pull the water out after being unceremoniously dunked. “Becky cheats.”

“You’re just a sore loser,” Becky taunted while Chuck simply smiled and avoided getting between the two girls.

Max, a new-comer to the neighborhood but one who’d easily meshed with the four of us thanks to his goofy, easy-going nature, chimed in from his seat on the side of the pool. “There’s no cheating in chicken. I’m afraid this round goes to Becky.”

“Your queen.” Becky winked.

Becky and Eve, despite their differences, had been best friends since grade school. They’d also shared something of a rivalry, often an open and heated one, over just about everything. Each had a competitive streak a mile wide. Fortunately, they made up quickly when things got out of hand. Chuck and I had long since learned to stay out of the fray.

“I’d hardly call a game of chicken enough to warrant that title,” Eve said. “Not even close.”

“Oh, I smell a challenge coming on,” Max said, sliding fully into the water. There was a glint in his eye and I couldn’t help but smile. As a spectator, this could be fun.

“Bring it, then,” Becky said, tapping Chuck on the head to get him to let her back down.

“As if you could beat me in anything.” Eve crossed her arms beneath her modest breasts, which only served to draw my attention that way. Where Becky tended to dress fashionably in tight everything, leaving little to the imagination in terms of her curvy figure, Eve preferred to dress casual and modestly, making her summer bikini appearances something of an annual revelation.

“Okay, so it’s to be a challenge,” Max said. “I nominate myself the referee. Anyone opposed?”

No one objected.

“Let’s find a suitable challenge,” he continued. “Eve — what’s the most daring thing you’ve ever done?”

Eve tilted her head in thought. I’d heard a few of her stories, including some things she and Becky had done during summer camps together. The single-most daring, however, I had no idea.

“Probably the time I went up to a stranger’s house in nothing but my underwear and rang the doorbell,” she said. There was a hint of blush to her face as she said it, visible even under dim lights of the pool at night.

Becky blew a raspberry. “That’s it? That’s nothing!”

“Yeah, well, I had to do it alone and at night,” Eve continued. “And to win the dare, I had to borrow their phone and call my friend to prove it.”

Wow! I was impressed. I was also surprised she’d had the guts to do it.

Becky seemed slightly mollified. “Better. But did you actually do it?”

Eve smiled. “Of course I did. And the guy who answered the door was cute. Too old, but I’m pretty sure it made his year.

“But I suppose you think you can do better than that?”

Everyone’s attention turned to Becky, who was already grinning with confidence.

“I went skinny dipping in a stranger’s pool,” she said. “Also on a dare. Had to spend ten minutes in it, too.”

And to think I’d been impressed with Eve’s adventure. Skinny dipping? It boggled my eighteen-year-old mind. Becky had a lovely figure and full chest. Given the skimpy bikinis she liked to wear, it didn’t take much imagination to picture her nude. My mind had certainly gone there more than a few times and I jealously cursed Chuck for having gotten to see the real thing.

Eve seemed less impressed. “And did anyone see you, or was this under cover of darkness?”

Becky shrugged. “My cousin, Wendy. Can’t say if anyone else did. And, yeah, it was dark out.”

Max raised his hands. “Okay, I think I see the challenge here. Both of you seem less than impressed with what the other did at their most daring. So, it’s time to back that up.”

He turned to face Becky. “Becky, your challenge is to visit seven different houses over seven days, all in Bear Creek. At each, you must pose in your underwear with the owner or a resident.”

Becky blanched a little but didn’t say anything.

Max grinned. “Oh, if you want the title of Queen of Bear Creek, you’re going to have to earn it. To make this a worthy challenge, there are a couple complications. First, the person you’re posing with also has to be in their underwear.”

“What!?” Becky couldn’t hold back at that. Eve just smiled.

“And…” Max let the tension build. “You need photographic proof.”

Becky groaned. “Perv. And, geez, that’s not going to be awkward trying to get all that.”

“A lofty title needs a serious challenge,” Max said. “And, don’t think I’m going easy on you, Eve.”

Eve, bobbing in the water beside me, tensed up. After hearing Becky’s challenge, she had good reason to be nervous.

“You get to go skinny dipping. Same deal — seven different pools over seven nights, all in our neighborhood.”

Eve tried to look unmoved. “Of course.”

“With pictures for proof,” Max said. “But you’re allowed to blur out the private bits.”

That was a hell of a challenge, for the both of them. On the surface, it seemed like Eve had the worst of it, but then she apparently didn’t have to interact or have witnesses. It might just mean a lot of sneaking around late at night.

“Yikes, those are both rough,” Chuck said, echoing my thoughts.

Max’s evil smile widened to Luciferian levels. “Oh, I’m not done. Becky, you have to bring Chuck along and he has to pose in his underwear as well.”

Chuck’s eyes bulged. “Me? Why? I’m not in the running for Queen.”

Max’s eyes turned on me and I felt a sinking feeling in the pit of my stomach. “And you, Rand, you’ll have to skinny dip with Eve in order for her to get credit.”

Eve cast a glance my way that was utterly unreadable. Me? On one tiny level, I was thrilled at the idea of getting to see Eve naked, of having this skinny dipping adventure together. On the other and infinitely bigger level, I was terrified of being caught…or being seen by Eve, or embarrassing myself, or…

“What Chuck said,” I said, lamely.

Max latched on to my discomfort like a leech. “What, you don’t want to see Eve naked?”

“I didn’t say that!” I felt my face burning. “I mean, not that there’s anything wrong with that, but, I mean, it’s the girls’ challenge. I wouldn’t want to risk holding her back or anything.”

Eve’s expression softened slightly, but I still couldn’t tell how she felt about it. At least my fumbling response hadn’t pissed her off. She was, inwardly, probably just as freaked out as I was. She just wouldn’t want to give Becky the pleasure of seeing it. Because Becky, after hearing about Chuck’s involvement in her challenge, seemed rather pleased.

“Sorry, folks, but those are the terms,” Max said, brooking no dissent. “You guys will be along for support and protection, since these dares aren’t entirely without some risk.”

Well, he did have a point there, not that I felt like some great protector. Hell, I’d be naked, too. How capable would I be in keeping Eve from getting caught or running some nosey neighbor off? If anything, having two of us would make it more likely we’d get caught.

“Are there even seven pools in our neighborhood?” I asked.

Our neighborhood of Bear Creek was so small as to be almost unknown outside those who lived here. It constituted all of one road that looped in an oval with houses around the periphery and in the middle. Three-quarters of the neighborhood was surrounded by woods, while the rest butted up against a private golf course. The homes were nice, but hardly mansions, and the yards weren’t so big that neighbors couldn’t be nosey. At best, there were maybe twenty-five or thirty homes in total.

Max hesitated. “Hmmm…good question. Let me check.”

I wasn’t sure how he intended to do that until he hopped out of the pool and turned on his phone. Ah — Google maps in satellite mode. Nothing like a little surveillance snooping. The rest of us got out and crowded around him as he zoomed in and started counting.

“You’re in luck,” he said. “I count seven.”

“Not exactly any flexibility built in there,” I said. “They get to pick from all the houses.”

Max shrugged. “Yeah, but they have to get the owners to join them. You don’t have to be seen.”

“They’ll probably just sneak in at like four in the morning,” Becky said, also finding issue with the disparity in the tasks. “That’s hardly risky.”

Max considered that. “Okay, how about this? All photo proof from each team has to be time-stamped between 6am and midnight. Photos also have to be geo-tagged to verify the location. Eve and Rand’s can be fuzzed out to make it PG, but not so much as to question whether nakedness was achieved. I’ll also allow Becky and Chuck to fuzz out their host’s face if requested, but only twice. Fair?”

I wasn’t happy about losing the wee hours option, but the neighborhood was quiet enough that we’d probably be just as discreet in the eleven to midnight hour. I wouldn’t have to come up with stories for my parents, either, as to my late-night excursions.

“Sure, I guess,” Eve said. Becky nodded in agreement. Chuck and I exchanged a glance, equally resigned to our roles.

“Okay,” Max said, setting his phone aside. “Game on, then. The challenge starts at 6am tomorrow morning and ends at midnight in seven days. Send you pictures to me by 12:15 each night, and you can’t do multiples on one day. Has to be one each day with no repeats. Cheating will result in forfeit! Highest score wins title of Queen of Bear Creek, and sidekick.”

Sidekick indeed. Eve looked up at me and there was a glint of determination in her eyes. Awkward as this might be, I could tell she intended to win. I didn’t want to let her down.

Chuck threw Becky back into her pool, then jumped in after. Max excused himself to go inside, leaving me alone with Eve. I did my best to keep my eyes off the body that would soon be far more exposed to me than it currently was in her bikini.

“You good with this?” she asked.

I shrugged. “I’d be lying if I said I wasn’t nervous.”

She nodded. “Yeah, me too. But gotta keep the game face on around Becky. Sorry you got dragged into it. I didn’t expect that.”

I tried to act nonchalant. “It’s cool. I don’t do enough crazy shit as it is.”

She smiled. “Well, this should make up for it.”

I sensed something in her demeanor. Discomfort? “Are you okay with it? I mean, if you’re not, I can back out. Be the wuss.”

Eve’s expression hardened. “Becky would declare victory by default. So, yeah, I’m totally in. Period.”

Well, clearly that wasn’t what had been on her mind. “Fair enough. How do we want to do this?”

Eve pursed her lips. “Not sure, but I definitely want to do it under cover of darkness. So, late. I’m pretty busy with work tomorrow. Do you think you could start scouting our prospects?”


“I’ll text you tomorrow afternoon and we can figure the rest out from there.”

I had a busy day ahead of me, not the least of which would be worrying about how I could keep from chickening out, or what Eve might think of my naked body, or how I might embarrassingly react to the sight of hers.

“Sounds good.”

Night 1 (Vs. the First Time)

My predisposition to over-plan things helped get me through the day. I studied Google maps, gleaning everything I could from the seven addresses in our neighborhood which had pools. With that information in hand, I walked the neighborhood loop several times, making additional notes about fences, bushes that might offer cover, signs of dog ownership, who might be home or on vacation. Anything and everything came into play. I sure as hell didn’t want to get caught, especially when most of the neighbors knew each other.

Eve and I shared a few texts and I got the impression that she trusted me to handle the selection of our first night’s target. When ten-thirty rolled around, I quietly let myself out the backdoor and into our detached garage. Eve was already waiting, shuffling nervously in an over-sized t-shirt and flip flops. I could see the tie of her bikini top sticking out of the neck hole.

“Never thought I’d stress out about what to wear skinny-dipping,” she said.

“Swimsuit,” I said, looking down at my own trunks. “Figured since we’ll be sneaking around the neighborhood in the dark, carrying towels, we can just say we were at a friend’s house to swim. We do it often enough.”

She nodded and held up her own towel. “Exactly. So, where first?”

I dug my notebook out from under a pile of musty tarps. In the back, I’d sketched out the targets and added my compiled notes. I pointed at a house just four doors down from my house.

“Figured we’d start with the easiest, just to get the hang of things,” I said.

“And what makes this one easy?”

“It’s for sale and the owners already moved out.”

She smiled and nodded appreciatively. “So we just have to worry about the neighbors.”

“Exactly. It looks like there’s a decent bit of cover, but we won’t know for sure until we get over there. Plus, I don’t think either neighbor has a dog.”

“Lead on.”

We started walking down the block, doing out best to project an aura of nonchalance. Nothing to see here. No kids about to sneak into someone’s yard for a spot of skinny dipping.

I, meanwhile, was nervous as hell. What had been abstract — getting naked with a girl I’d crushed on for a decade — was suddenly becoming very real. How would it go? Would it change things between us? If so, for better or worse?

“I can’t believe we’re doing this,” she said. Good, at least I wasn’t the only one nervous.

“No kidding. Did you hear if the others were successful today?”

Eve snorted. “Yeah, they were. Cheating bastards got Chuck’s brother to pose with them.”


“I know, right? But, I guess they’d probably say the same about us going to a vacant house.”

“One gimmie for each of us on the first day, I guess.”

We reached the house, dark except for the porch light which dimly lit the real estate sign out front. Both of us looked up and down the street and at neighbors’ houses and found no sign of anyone watching. Trying to act calm, we snuck across the front yard and around the side of the house. It was surrounded by a wood privacy fence which, thankfully, had no lock. The thing squeaked more than I cared for, but probably not enough to catch anyone’s attention unless they were outside and close by.

The backyard was empty save for the pool — a bean-shaped in-ground affair not unlike the one at Becky’s house. A concrete patio wrapped around it, but any furnishings had departed with the residents. The pool’s underwater lights, presumably on a timer, were on, giving everything a soft blue glow.

“Check the neighbor’s backyards?” Eve whispered.

I nodded and we each took a side. This house backed up to woods, so we only had to worry about two homes. The one I checked was dark except for a single upstairs light. Should someone look outside, it was possible they could see us just about anywhere in the pool. Fortunately, the blinds were drawn closed and as long as we were quiet we’d probably be safe.

“Clear,” I said when we met back up. “Upper floor probably has a view, but the blinds are closed.”

“Same over here. Think we should be good if we’re quick and quiet. Any other escape routes?”

I hadn’t given much thought to escape, should we be spotted. There appeared to only be the one gate and I didn’t think either of us could safely climb the wood fence in a hurry.

“Not really, no.”

“And you brought your camera, right?”

I unrolled my towel, revealing my cellphone and the mini tripod I’d bought for vacation last summer. It took just a couple seconds to get it seated. With my phone being waterproof, voice activated, and good at shooting in low light, we’d agreed I would handle the pictures. Of course, I promised Eve I’d carefully edit the pics and then delete the originals.

“How do we do this?” she asked.

I shrugged. “I don’t know. Get undressed, get wet, take a picture?”

She rolled her eyes and gave me a playful swat on the arm. “I meant the picture. Where?”

I looked at the pool and got an idea. “How about I set the camera over here, about five feet from the side. After we get in, we can climb up and sit on the side in front of it. I’ll voice activate it and we get a shot of us sitting from behind. Won’t show much, but Max will be able to tell we’re naked.”

Eve agreed and sounded relieved. “Okay. I guess this is it, then.”


We looked at each other, my own nerves reflected clearly in her eyes. We smiled and laughed, though it was tense.

“My god, this is so embarrassing,” Eve said.

“So, it’s not just me, then?”

She shook her head no. “Do you mind if we, I don’t know, maybe not look at each other getting undressed? I know it’s going to be impossible not to see each other, but…god, I just need to ease into this, I guess.”

I liked her way of thinking. “Sure. How about I face the house and you face the pool? As soon as you’re ready, you get in the pool, then I’ll get in after you’re under water.”

She smiled. “We’re such prudes.”

“Yeah. But at least we’re prudes together.”

“Okay, I like it. Ready?”


I turned toward the house and took a deep breath. This was it. Moment of truth. I pulled off my t-shirt. That was the easy part. Behind me, I could hear Eve doing likewise. Was she really facing away or sneaking a peek? I doubted the latter, but I wouldn’t dare risk being caught sneaking a peek to find out.

I reached for my waistband. On the upside, I was so ridiculously nervous that I was as far from aroused as possible. One less thing to worry about.

Behind me, I heard Eve working off her bikini. I couldn’t chicken out now and leave her hanging alone. Like ripping off a Band-aid, I took a deep breath and dropped my suit to the ground. The cool night air brushed my cock in an unfamiliar but not unpleasant way. I looked side to side, half expecting a neighbor to be peering over the fence with a camera, but the coast remained clear.

I almost turned, but remembered I was supposed to wait when I heard the first soft splash of water.

“It’s brisk,” Eve said. Moments later, there was a bigger splash. “Okay, I’m in.”

I turned and was relieved to find Eve floating toward the middle of the pool, her back to me. I stepped around her discarded bikini and quickly descended the steps into the water, eager to hide myself just as the water was hiding her naked body.

We were both naked. Naked together and alone. How crazy was that? And the world hadn’t ended.

“I’m in,” I said, giving her the all clear.

She turned, water up to her neck, and smiled. I’ll admit, I tried to check out her tits, but between the darkness and the waves I couldn’t make anything out. If she noticed me trying, she didn’t say anything.