Email from Cindy's Box #05

There I was, just minding my own, having a nice little evening on the internets after a significantly less than nice little evening out with a guy, when suddenly...

donkeykongxxx99: hey

If I just ignore him, he'll go away.

donkeykongxxx99: hey
donkeykongxxx99: hey cindy
donkeykongxxx99: hey

Ug.

little_asian_cherry: What now, Frank?
donkeykongxxx99: u owe me $300

I so did.

little_asian_cherry: No I don't.
little_asian_cherry: You cheated.
donkeykongxxx99: did not
donkeykongxxx99: and you know it

He didn't. I knew it. But money is tight when you're working your way through college.

little_asian_cherry: I don't have $300 to just give you.
donkeykongxxx99: hey
donkeykongxxx99: you can always work it off

Classy. As always.

little_asian_cherry: What is it this time?
donkeykongxxx99: you don't even have to touch me
donkeykongxxx99: :)
donkeykongxxx99: do this:

That's when he sent me the link. It was to some truth or dare website. A forum of crazy dares people have done. Or that people want someone to do. Or something.

He's been screwing with me like this for a while. Last time he sent me a link to a video of a girl walking down the street, talking to some guy. They ducked behind a fence or something and she pulled out his cock right there like it was nothing, started sucking on it. Next thing you know, she's walking down the street, scooping his cum off her face with a spoon and sucking it down.

Ya, that was so gonna happen. I sighed, scanning the page.

little_asian_cherry: This isn't even enough.
donkeykongxxx99: huh
little_asian_cherry: It only adds to $80+whoever's watching.
donkeykongxxx99: ...
donkeykongxxx99: u wanna fuck me?
donkeykongxxx99: for $6?

No, or else I'd've accepted his first offer to cover the whole $300. Of course, if they were caught on camera, the public "partner" dares didn't have to actually be observed by anyone... but no fucking way were him and me going to do these things on camera. Or off.

little_asian_cherry: No.
donkeykongxxx99: u can do the solo girl ones
little_asian_cherry: Still only $48.
donkeykongxxx99: ...
donkeykongxxx99: $6 per point

Seriously?

little_asian_cherry: I'd hafta do all of it, and I'd still be short.
little_asian_cherry: $10.
donkeykongxxx99: u srs?
little_asian_cherry: $10.
donkeykongxxx99: 8
little_asian_cherry: $10.
little_asian_cherry: And you owe me if I go over.
donkeykongxxx99: u rly srs?
little_asian_cherry: Yes.
donkeykongxxx99: fuck
donkeykongxxx99: ok, ya, 10
donkeykongxxx99: sweet!

Maybe I shoulda gone higher. I could only get, like, 12 points without having to, you know, open my legs to someone. I really shouldn't have counted the "use a dildo" and "have an orgasm" points in my math, either. Of course, if I did do them, I'd end up with a tidy profit...

We figured out the place to do it. A Holiday Inn in New Jersey. Far enough that we'd probably not be spotted by anyone who mattered. Close enough to drive back in the middle of the night. He told me he'd bring his camera and I should bring a dildo, so I told him to go fuck himself. When he'd come to pick me up, he just smiled when he spotted the dildo, lube and large bottle of tequila in the bag I set down next to his fancy camera.

Only the second floor had balconies, which was definitely going to be a necessity. The room was by the front door, so I figured I'd get enough foot traffic that I wouldn't just have to put on a very long show for one random guy.

I was ready. That is to say, I wasn't ready at all, I was freaking the fuck out, but everything in the room was ready. The website said to put a cellphone on the balcony, and Frank was going to call when someone was in a position to spot me. I'd left the list of things to do, a pen and a bottle of courage out there, too. Not that I couldn't trust Frank to keep track, just that, well... he had little incentive for honesty. And I anticipated being somewhat more pliable than normal by the end of the evening.

I heard the phone ringing through the open doors and hopped out of the shower. I tossed on the hotel bathrobe (which barely made it down my thighs) and ran out, my breasts bouncing heavily, the robe dangling partly open and baring a wide strip of skin all the way down.

4 points right there, and I didn't even mean to do it! My heart was racing, but it had already been racing while I'd waited in the shower. I realized I was holding my breath, and exhaled.

I answered. "Hello?" I said, in a meek sqeek. I coughed, "Hello?" I repeated, loud enough for whoever was below to hear, my voice still shaky against my fluttering heart. I tried to look down sneakily, I didn't want them to think I knew they were there.

"There's a guy smoking a cigarette. I think he's already looking at you."

"Awesome! That's four points!" I hastily dried my hands on the front of the robe and checked off "Expose Pussy." I bit my lip. Standing out on this balcony, these tasks seemed much more... daunting than they had sitting at my computer. It was exciting to get one knocked down, but intensely frigtening how much further I had to go.

"That wasn't no ten seconds." He said gruffly.

My high collapsed. "Fuck." I whispered back, scratching out the check. "Did we really agree to ten seconds?" I squeeked.

"Yes."

"Even for the touching ones?"

"Yup."

"Right..." I put down the pen. The bucket of ice that held the silver Cuervo "Tradicional" was half water now, but the bottle was still icy to the touch in the warm night air. I awkwardly tugged at the cork, struggling to get it out, and poured a shot's worth into the hotel-room coffee cup. I knocked it back, coughing, smacking the sharp flavor from my lips as I set the cup down.

I stiffly turned to the rail, looking out into the distance as I held up the phone. I'd wrapped the robe around me after my initial exposure, and it still hadn't fallen back away enough to expose anything just yet. That was good, because I was already nervous about the relatively small stuff at the beginning of the list. I certainly didn't feel like standing there for too terribly long with my pussy bared. I didn't quite feel like standing there with it bared for ten whole seconds, even.

"Okay..." I licked my lips, still sharp with the tequila, and lifted my hand to my chest, "Ten seconds." I cupped a breast. The touch was atypically intense, and just the thought of the things I'd agreed to was already making me wet. I hadn't even gotten started yet!

"Well?" He said.

"Well what?" I stood there, hand on boob, counting under my breath.

"Are you going to start?"

"I'm touching my breast..." I muttered softly.

"No, you've just got your hand to your chest." He said.

"That's where my breasts are..."

"Ya, but you're touching the robe."

I paused.

"You mean..." I dropped my hand to the rail, "You mean I have to put my hand inside my robe?"

"Duh. It doesn't say touch your robe." I could hear his eyes rolling.

I sighed. I licked my lips, looking down to try and see the smoker without turning my head. There he was. Looking right at me.

Stilted, I moved my hand mechanically to the opening of my robe, pushing it under the white terry cloth. My fingers, still ice cold from the bottle, brushed along my nipple, and I let out a squeek. This was going to be a rough night...

I grasped my breast. One one thousand. Two one thousand.

I could tell how wet I was. I was literally on the very first thing. One point. And I was already more turned on than I'd been in a long time...

"Time." He said.

As much as I wanted to, I couldn't jerk my hand away. As awkward as it was to have it shoved in there with a man just below staring right up at me, my nipple was next. I slid my fingers up to it, feeling it stiffen under their touch. I suddenly ached to touch more almost as much as I ached to turn around and run inside. I glanced down again at the smoker and felt my face turn pink. This was too much. I couldn't go through with it.

"Are you touching your nipple?"

"Yes..." I whispered. Four one thousand.

"I can't tell..." He paused. "It hasta be obvious. Move your fingers, so it's obvious."

"What?" It would seem that my timer hadn't even started.

"Move your fingers."

I bit my lip. I slid my fingertips around my soft, tender flesh. It felt so good. I twisted my knees as my thighs tightened involuntarily.

"Time." That one went by much faster than the last.

"What, uh," I slid my hand out of my robe, glancing down at my smoker. Still smoking. I looked away, quickly, blushing, hoping he hadn't seen my head turn toward him. "What's next on the list?"

"Ass... but, touching your ass is easy." He said.

"Not if I hafta reach under my robe..." I said back, softly.

"Ya." Pause. "Do it."

I nodded, putting my arm behind me. Really, I couldn't just "reach under my robe." I had to lift it up and place my hand on my bared ass. It felt kinda dumb, and probably looked weird, but this wasn't really "exposed," since the smoker still couldn't see it. I felt the robe on my thighs as it pulled up in back, easily low enough to still cover me there. At least for now.

Five one thousand. I stared off in the distance, pretending to be talking on the phone, but thinking about the wetness between my legs. I'd already made it to $20. This would make $40.

"Nice." He said. "You're up to 9 points. Damn, girl, you've made $90 in under a minute!"

My eyes went wide. 9 points? Boob, nipple, butt, 4 points. Where were the other 5? Maybe 1 per watcher? There's still 4 more.

I looked down. Lifting the back of the robe hadn't lifted the front high enough to expose anything, but it had pulled the front apart. And that exposed plenty!

I shakily pushed the back of the robe down, pulling the bottom together with one hand as I spun my back to the rail. My heart was suddenly racing again, and I could feel each beat as a pulse between my legs!

$90. 21 points to go.

I poured the open bottle into the coffee cup. More like a double this time. I wet my lips, although the other pair were wet enough already, and lifted it up. I hesitated, took a deep breath, and downed the tequila. I sputtered at the harsh burn, dropping the cup. It broke against the hard balcony.

I exhaled the strong, tangy flavor. Maybe it was because it was just a stranger, just someone anonymous from New Jersey. Maybe it was the fire between my legs. Maybe it was the tequila already pumping through my tiny body. But it wasn't because I wasn't thinking. I certainly was thinking. And the thought that came into my head when I looked down at the shards of the coffee cup made the wet little slit between my legs suddenly ache. I couldn't do that. But, then, I couldn't not do it. Not now that I'd seen it in my head. I'd have to get to $300 somehow.

"Can things stack?" I asked, my voice crumbling just at the thought of what I was planning.

"Like touch and expose counts for expose, too?"

"Ya, sure." I said, leaning back against to the rail, hoping the smoker was still watching.

A pause. "Okay." He said. "But it doesn't count for touch while covered."

"Okay..." I licked my lips again. "He's still there?"

"Of course. Staring right up at you, nursing that cigarette butt."

"Good..." I leaned forward, down toward the mess. I could feel the short robe ride quickly up my backside, exposing my toned cheeks to the man below.

I slid my feet apart, and soon my butt wasn't the only thing exposed. As I twisted my hips and pushed my hot wetness out in view for my watcher, my butt pressed gently against the cold rail. Shivers ran up my spine, less from the chill of the metal than from the real, physical, sensory proof of just what all I was baring.

I knew I'd already gotten credit for baring my pussy, but this should now count for both my ass and a more unusual thing from the list. A "fuckable pose."

"Nice!" I heard him say over the phone.

Boob, nipple, butt, all touched while covered. Butt bared, a fuckable pose. A watcher. "That makes 16?" I asked.

"If you wanna make this a fuckable pose, you've gotta hold it for 30 seconds, babe." He said. I bit my lip, the man below was easily able to stare right up along my smooth legs, right up to the hot, wet little slit between them, shaved clean from just moments ago in the shower.

"Here's 12 more..." I said, setting down the phone. I reached my hands back, placing one hand on a cheek, pulling it open, sliding the other between my legs and onto my pussy, pulling that open too.

I was standing on a hotel balcony, bent over, spreading not only my butt cheeks, but my achingly hot pussy lips. All for some random guy. Some random, lucky, smoking guy.

Twenty nine one thousand. Thirty one thousand.

I dropped my hands, grabbing the phone, scooping up the shards of the cup, my ass still bared as I did. I stood, setting the broken cup on the table and pushing the robe down in back. It had fallen wide open while I was bent over, and hung loosely apart in front now, a strip of bare skin running down between my breasts to my hungry little slit once again. I lifted the phone as I pulled the robe shut.

"What am I up to?" I asked, softly.

"25." He said. I bit my lip. My heart was pounding, my pussy burning. I was only $50 short now.

I turned to my table and checked stuff off. "I count three more than that." I said, frowning.

"Did you count touching spread pussy while exposed?" He asked. Fuck, was there something special about that one? These things were awful damn specific. No wonder I was fucking it up. I shouldn't've let him ferret out so many stipulations on the drive down.

"Yes?" Fuck. That's right. We'd agreed on this. That one meant putting a finger in, since spreading my lips meant touching my pussy anyway. "Fuck." I looked at what else was left to get me 5 points.

Even if I whipped my tits out now and played with them right in front of this guy, I'd still be $10 short. And everything else would end up very poorly, because, at this point, if I actually did any of the other things left on this list for the required length of time, I'd seriously forget how to count and would end up getting those 6 points for "Orgasm" too. And the tits weren't entirely a guarantee of avoiding getting drawn into that one, either.

I needed a drink. I frowned at the shattered cup, and considered drinking straight from the bottle. I figured that I probably shouldn't.

I slid open the balcony door, surprised to find myself stumbling slighty. Already tipsy, and here I was, getting more. I wondered into the room and found the cheap paper coffee cups by the coffee maker in the bathroom. Grabbing one, I turned back to the balcony, frowning briefly at the purple rubber penis laying on the bed.

This would've been easier if the first floor rooms had big sliding glass doors. Why don't they build hotels so it's easier to spy on the guests? So inconsiderate.

I stepped out on the balcony, pouring about another double, and tossing it back. It went down easier this time, I only wheezed a little.

I picked up the phone. "Hokay. What's next?"

"Dildo and orgasm." He said.

"Shuddup. Seriously, what's next?"

"It doesn't matter, Cindy, your watcher left."

"What?" I leapt to the rail, looking down. No smoker.

"I guess he thought the show was over."

I frowned. I was still $50 short, and I wouldn't get any more without someone watching. I sat on the chair, the metal frame cold against my legs.

"You want to call it a night?" He said, "You only owe me $50 now." A pause on the line as I considered it. "This has been fucking awesome, by the way. Fuck, you're fucking hot."

I looked out at the parking lot, trying to remember which car was his. "Are you fucking stroking it right now?"

Silence.

"You are, you sick fuck!" I laughed into the phone.

"Shut the fuck up, I'm not the one baring it all on a hotel balcony for $300."

"$300 is, like, a fucking classy whore, asshole." I laughed, "Plus, I haven't bared it all." I grabbed the list. "I haven't bared my ti-"

"Cindy! Hey! C'mon! Do it now!" He cut me off. He totally was fucking stroking it, and wanted me to give him a show to finish off!

I rolled my eyes. "I'm not flashing you just for funsies."

"Some guy just ran out. It looks like he's getting something from his car. Do it quick, before he's gone!"

I popped up, hazily scanning the parking lot. I didn't see anyone. I bit my lip. This could be a trick. Fuck him, I want my money. If it's a trick, I'll call it a $50 trick and he can fuck himself. He already is, anyways.

I pulled open the top of the robe, fighting with the belt as the shoulders slipped down my arms. Angrily, I yanked the damn thing off and tossed it on the table.

So, there I was, half drunk and completely naked, standing on a hotel balcony in the dark of night, searching for an imaginary man in the parking lot. I leaned out over the rail, licking my lips as I realized one hand was already running along my bare breast, teasing at my nipple.

Stop that, I thought, it doesn't count unless someone's watching. And I didn't want to give Frank a free show. I still wanted my money more than I ached to push that hand down between my legs, but it wasn't clear my priorities would hold.

I turned around to grab the phone. "Fuck you, there's no one -" As I turned back, he passed under a lamp post. There he was. Some guy searching through a bag as he walked, hardly even watching where he was going, let alone watching the horny, naked girl he was about to walk right under.

I had to get his attention. I turned back to the table. The bottle of tequila might kill him, that would be bad. No points. The shards of broken cup were likely not a great idea. I'd miss with the paper cup...

The robe!

Hurriedly, I ripped the robe from the table, throwing it over the balcony, right into the path of the man below.

I leaned over the rail, my bared breasts swaying slightly as they hung out in the open air. The robe tumbled painfully slowly in an awkwardly crooked line.

"C'mon, c'mon..." I tapped a foot as it landed deftly on his head.

He jumped, pulling it off and holding it up. He looked around, then up. I smiled down at him as his eyes widened.

I gave just long enough of a hesitation not to be suspicious, because totally naked girls leaning over a balcony and staring at you are normally not suspicious at all. Then I glanced down in mock surprise at my bare breasts, their large, dark nipples highlighted by the nearby lamp post. I shot my hands to cover them, as I certainly wouldn't have noticed them exposed until just this moment.

"Gosh, mister," I said in the velvety softest, sugary sweetest voice I could muster through my haze of tequila and lust. My whole left hand was placed well around my right nipple, but when my sneaky right-handed fingertips crossed over, they had landed squarely in the middle of the nipplethey were meant to hide. I licked my lips as they happily drew small circles on the tender flesh, the mans eye's locked onto their not-so-subtle motion.

"Could you possibly be, just, like, the nicest guy ever and bring that back up to me?" I smiled down at him, "I'd be, just, terribly grateful. It's the hotel bathrobe, you see, and, I just can't just, like, lose it. So, like, can you just come up here real quick and give it to me?" I batted my eyelashes, but it felt so awkward as I leaned, naked, over a rail that I couldn't help but sputter a laugh. "Please?" I grinned.

He managed to tear his eyes from my naked body to look down at the robe. "Yes, certainly. I'll be right up, then?" British. He was even more of a stranger than just some random New Jersey guy. Perfect! "I'll, I'll be right there." He nodded, hurrying to the front door.

"Hey, mister!" I shouted after him, straining to sound innocent and sweet while naked and yelling loudly out at a hotel parking lot.