Lucky Penny by Imp Again

I was beginning to understand why I was the one selected to attend this convention. Having only worked at my architectural design firm for five years, I was by far among the most junior members of the staff. So when they offered me a weekend in Boston, albeit in September, at a four-star hotel for the annual Elevator Contractors Convention, I didn’t know whether to be honored or suspicious. Now, staring at a nearly empty reception hall, the old boys long gone and probably three sheets to the wind already, I found myself the only thirty something in the room. Every one else was older and, judging by their demeanor, equally or even less enthusiastic about being here. Some were mindlessly scanning their cell phones, some struggling with small talk over by the wine bar, but all signs pointed to the fact that at 6pm on a Saturday night, I should probably get the hell out of here.

Walking out into the hallway, the view out the second floor window greeted me with a rainy evening sky. Great, I thought, guess I won’t even be going out in tonight. I didn’t feel like bar hopping by myself in the rain, but resolving not to just give up and head back to my room, I hit the down button thinking I’d at least give the hotel bar a shot. I could certainly use a drink or three after the mind-numbing afternoon I’d just endured.

When the bell chimed and the doors parted, I walked straight in not realizing I’d been gazing at my own shoes. When I raised my head, what I saw and what I heard stopped me cold in my tracks.

“Hello there, Devin Preston.”

In front of me was an absolutely beautiful young Amer-Asian woman of maybe five feet two, in a charcoal spaghetti strap cocktail dress. Her pixie cut jet black hair framed her round cheeks and charming smile, but what froze me, beside the fact that she somehow knew my name, were her stunning amber eyes that luminously offset her pale caramel skin.

The look on my face must have been priceless, because she immediately giggled and glanced at my chest before nodding. “How’s the meeting coming along?” she asked, indicating my name tag.

I laughed aloud at myself, piecing it all together. “Ah, right. Fine, just fine.” I let my eyes wander just a bit, assessing her outfit before returning the question. “And what brings you here looking so lovely, Miss…?”

“Oh, you know, nothing. I just like riding elevators in fancy hotels. Makes a girl feel special. And I’m Penny.” She didn’t offer her hand with her introduction, instead stood with them both behind her back, rocking slightly in her high-heeled sandals.

“I see. Guess it’s my lucky day, then huh,” I said, attempting a joke and immediately regretting it. Her deadpan response told me it was nothing she hadn’t heard a thousand times before, and I felt like a first class moron.

“Ha, lucky penny,” she said flatly, “we’ll see about that. Where’re you headed?”

“Figured I take a peak at the hotel bar for a spell. You?”

“Well, by the most extraordinary of coincidences, I myself am heading in the same direction. Perhaps you need an escort?”

My eyes widened at her choice of words. I was having a hard time gauging her age, much less why she was alone in this hotel dressed so nicely. And her conversation wasn’t your ordinary hotel chat. If she knew what she’d just implied she didn’t let on at all, so I rolled along with it as the doors opened to the lobby.

“Right. Well, sure. Let’s have a drink.” I wasn’t even sure she was old enough, but she didn’t hesitate at the suggestion. As we crossed the vast marble foyer towards the lounge, I was compelled to inquire a bit. “I would have thought you were meeting someone here.”

“Actually, I’m trying to leave someone behind. Many someones, in fact. A whole family of them.” We walked in and sat down at the bar, and she ordered a glass of wine and I a whiskey soda. We were both, of course, carded, and both of us passed. That answered one lingering question.

“My cousin’s wedding reception is up on the third floor,” she continued. “My mom’s brother’s son. I’m not really tight with that whole side of the family, if you know what I mean. They don’t really get that my dad’s Japanese. But my parents insisted that I come along. I showed my face for as long as I could stand to, then I feigned illness and begged off to sleep in my room. Which is exactly where I am right now.” She gave me a conspiratorial smile over her glass.

“And you don’t think anyone will see you down here?” I asked, looking around perhaps a bit nervously.

“You mean with you?”

“I just meant that if you didn’t actually…”

“I know what you just meant, Mr. Devin Preston. Nope, trust me, it’s an open bar. Not one of those rednecks in my mom’s family would come down here and spend money when the booze is free upstairs. Anyway, almost nobody else in that crowd even knows who I am. I’m as good as gold down here. And what about you?” She leaned forward to read my nametag. “No buddies from the…NECA?”

“National Elevator Contractors Association.” I pulled off the tag and stuffed it into my pocket. “Nope. My office sent me out here all by myself.”

“Elevator Contractors Association!? Didn’t know such things existed. How’s that working out for you?” she asked looking absently at the bar, with a tone that implied utter disinterest.

“Has its ups and downs.” Another deadpan look. “Right. Enough with the dumb jokes. I’m a low level designer at an architecture company, and I’ve spent one very long day trying to figure out why they sent me out here.”

I stirred my drink and took a sip. “So you came out with your parents, huh? I should probably ask how old you are.”

She paused for a second before answering, then leaned over just a bit, looking me in the eye. “How old do you want me to be?”

Her brilliant hazel eyes were so engrossing it had me distracted, and I failed to understand the question. “What do you mean?”

She sat back and took a slow drink from her glass. “I mean, you just met me in this hotel, we’re sharing a drink. I look good. You look good. But you can’t figure out if you should keep going or not, right?”

I blushed and stammered a bit. “Well, no, I mean. Yeah, I just…”

She held my gaze and continued. “I could tell you anything at all, and you’d have to trust me or decide to go along with it.” She paused, putting her glass down. ”Or leave, I guess, if you didn’t want to go there, but you shouldn’t do that, please.” She put her hand on my knee for a moment. I looked down at her hand, then across to her own bare knees, crossed and compelling.

She shifted her position and re-crossed her legs, allowing me to glimpse a flash of her thighs. “Tell you what,” she said, “we’ll play a game. Two lies and a truth. I’ll give you three stories, and you can pick the one you like.” Her demeanor had become much more playful as her drink settled in, and I was feeling much better now finishing my own. This was obviously going somewhere, but in an entirely unexpected way.

“Alright, I’m in. I don’t quite follow you, but I’m in.”

‘You’ll see. Watch. According to what you know so far, I’m here with my family for a wedding, so did I arrive with them, or did I meet them? Maybe I came with them because I’m still living with them, because I’m still in high school. Do you think I look that young?”

“You know, honestly, I don’t think so. You forget we got carded when we sat down.”

“And you forget that a fake ID is not so hard to acquire. So I’m sitting here with you, very young and, well, very attractive,” she sat up proudly and smoothed her dress, “and my parents think I’m safely back in my room sick in bed while they’re off getting hammered with the rest of them. Story number one.”

“And a risky one at that,” I said. “Not sure if I want you that young.”

“Hm, but you do want me,” she smiled, “so that’s good. Story number two. I met my parents here because I’m already in college, so I’m old enough to be a safe bet, but still pretty young in the scheme of things. Does that make me more attractive?”

“You’re already attractive, I thought we covered that.”

“Well, sort of,” she said giving me a little squint. “I did, but you haven’t said as much. With your mouth anyway.”

“Allow me to remedy that. You are,” I paused and gave her whole being a good long look, “very, very attractive.”

She smiled and raised her glass in appreciation. “Thank you. You’re pretty darn good looking yourself. So, story number three. I made all of this up completely: the family, the wedding, all of it. I’m actually a graduate student over at any one of the universities in town, and I’m here working on my doctoral thesis.”

“At a bar, in a hotel, on Saturday night? And just what sort of research is that you’re working on?”

Another pause. “Human Sexuality, of course.”

I laughed, perhaps a little too loudly, earning some glances from the other patrons.

“We, you and me, are researching how young is too young in the mind of a man who has been given permission. And now I’m still younger than you, but maybe not as young as you’d like. Plus, now I’ve given you full disclosure on what I’m doing so you can’t come back when my paper is published and sue me. After you do me.” She winked. “So what do you think?”

“That you just gave me the start of a healthy erection,” is what I wanted to say, but what I actually said was, “Sixteen, twenty-ish, mid twenties. And I get to choose which one? Do I ever get to find out the real answer?”

She finished off her glass and stood up, pressing her body against my legs. “Maybe. Buy me a bottle of champagne and take me to your room and let’s find out.”

I paid the tab and had the bartender send up a bottle to the room, then walked Penny out with my hand on her waist, thinking whatever age I picked, I was at least right about it being my lucky day.

On the ride up in a crowded elevator I had a minute to think about what I was doing. What if she really is in high school?? What the hell is the age of consent in this state anyway? Or would it be from her home state? Jesus, Devin, what the hell are you doing?!?

But when we got to my floor and we stepped out into the hallway, my hesitation evaporated. I pointed the direction to my room and let her walk ahead of me slightly, watching her with the fresh perspective of knowing she would be all mine in just moments. Her dress, while not tight, hung closely to her petite frame, shaping her beautiful behind and draping nicely over the soft rise of what were probably only A-cup breasts, for she was clearly not wearing a bra. Her waist was slender and her bare shoulders were strong though still slight. She was womanly and girlish all at once, swaying her hips teasingly as she walked, well aware that I must be checking her out.

“Right here,” I said as we got to my room. She spun on her heels and raised her arms to my neck as I walked up to her, her hands warm and so, so soft, her almond eyes again piercing into me.

“Make up your mind yet?” she asked coyly, keeping me at arms length.

“About letting you come in? Yes, absolutely.” I slipped the card in and pushed open the door while still in her grasp.

“Not so fast, Mister.” I could smell the light scent of the wine on her breath, and found myself staring at her glossy lips. “You have to make a guess.”

“I guess all three,” and wrapped my arm around her waist, pulling her into the room with me. As the door swung shut I released her as she walked across to the couch and sat down, kicking off her shoes and crossing her smooth, lovely legs. Not quite sure how fast to proceed and remembering room service was still on the way, I kept my distance, leaning against the desk. She smiled at my hesitation.

“That’s right. You stay over there until you give me a proper guess, cheater,” giving me a stern. “Remember, I’m looking for data here. Unless I’m not a grad student, in which case I’m just horny college lush waiting for some free champagne. Or, even racier still, an innocent high schooler trying to keep you at bay until you get me drunk and take advantage of me.”

Thankfully the knock at the door got me out of responding immediately. Unnerved a little by that last bit, I took the bucket and glasses from the young man without letting him in, but thanked him just the same with a healthy tip. I brought the collection over to the table in front of the couch and sat down across from her in one of the armchairs.

Uncorking the bottle and filling the glasses, I offered hers up with a toast. “To youth,” I said, and we drank. Continuing, I said, “We never covered the rules of this game. I mean, what happens if I guess wrong? And can I ask more questions to get some data of my own? Do I at least get a hint?”

She downed her glass and held it out, insisting on more before answering. I poured her refill and sat back again, facing her.

“No hints,” she said, getting a little giggly. “But I suppose you can ask me some questions, although I’ll probably just tell you more lies. Except when I don’t. As for what happens if you pick the wrong girl, I guess it means you don’t get any of this.” She uncrossed her legs and opened her knees wide apart. Pulling up her dress a little she exposed her smooth, dark lips beneath a whisper of soft black hair, just covering the area of her pubic bone. “Oopsy, no panties.” She took a drink and looked at me while I stared, spellbound as the blood began to surge in my veins.

“Uh, oh,” She said teasingly, “ Somebody’s gonna have a hard time making the right choice!” She pulled her dress up the rest of the way and bunched it up around her waist, opening her legs now as wide as they would go. With her free hand she ran her fingers up and down her thigh. “Wanna ask me a question?”

I was almost fully erect and certainly bulging visibly, but I couldn’t take my eyes off of her magnificent pussy. To the left of her delicate patch of hair was a small red tattoo of some kind, small enough that it would be hidden if she actually were wearing panties, and too tiny for me to make out from across the table.

“Is that a little red smiley face?” I asked, unable to come up with a better question?

“Sort of,” she said, “It’s a little devil. I call him my little happy imp!”

I leaned over the table a bit to get a better look, and sure enough it was a tiny smiling cartoon devil. This girl was getting more interesting with every second.

“Hey, stop staring, you old letch.” She leaned forward and grabbed the bottle from the bucket and, after filling her twice emptied glass, placed it between her legs, right up against her pussy, letting out a girlish squeal, then a series of soft moans as she turned it slowly against her lips. “There,” she all but breathed, “you don’t get to see any more until you make some decisions.” Her jawed dropped open and her chin rose as silent moans forced her eyes shut. She masturbated herself against the cold, dripping bottle for a minute or so while I watched, then, when it had warmed up sufficiently with the heat of her skin, she leaned forward and dropped it back in the ice.

“Mmm,” she cooed, barely touching the cool skin of her slick, wet pussy with her fingertips. “That felt good! But since I’ve showed you mine, I think it’s about time you showed me yours. Let’s see what that bulge is all about.”

I undid my pants a pulled them down enough to release my straining hard on, which all but leapt out from it confines. Squeezing it in my hand I pulled it straight up for her, bringing it to its full dimension, then let it go for her to see.

“Ooooo!” she giggled, “That’s a REALLY nice cock!” She sat up a little to get a better look. “Oh yeah, I think you need to bring that over here so I can get a closer look.” Drawing me towards her with her finger, I got up, holding up my pants, and crossed over, standing at the couch between her and the table. She immediately began stroking it, lightly at first but then squeezing it more.

“So, here’s what we can do,” she said, looking up at me with those incredible eyes. ”I’m going to start kissing this, and you’re going to keep track of the number of kisses. When I get to the number that equals the age you think I am, you just tell me to stop. Ok?” She gave it a good, slow squeeze culminating at the base of my head, making my knees buckle. “Does that sound too hard?” she said so sweetly it made me want to cum right in her face. I just nodded.

She placed the first tiny kiss right on the tip, and the next few down the underside, slowly and carefully. “Maybe you should count out loud so we don’t loose track. Do you know where we are now?”

“Five!” I said, more urgently than expected, and she looked up and smiled appreciatively at the compliment. “Six… Seven… Eight…” I continued as she softly kissed her way back up. Somewhere around ten her kisses became small sucks, as she drew the tip of my head into her mouth, then gradually the whole of it, then began moving her lips down over the shaft. And each time she drew me in she lingered longer, and longer, blurring the line between where one kiss ended and another began.

When I failed to keep count somewhere in the high teens she didn’t stop to correct me, but only took more of me in, and held me for longer, until she was fully sucking my cock without releasing it. Both hands were engaged in stroking me and fondling my balls while my she drew me deeper still into her young pretty mouth. Whatever her age, she sure as hell had given a few blowjobs before, and I was focusing as much on enjoying it as I was keeping her from making me cum.

She released me from her mouth and began rubbing my cock over her face. Looking up she said, “Is that your guess?”

“What guess?? It’s kind of hard to keep count when you stop kissing and start sucking.” I didn’t even remember what number I’d said last, but I’m pretty sure I didn’t make it to twenty.

She kept my cock pressed to her face, turned on by the feel of it and breathing heavy. “Do you think you were close?”

“To your age?”

“To cumming,” she said, and took me back into her mouth completely, pressing me into the back of her throat and holding me there. I could feel it welling up again as my balls grew taught, and I let out a gasp of exasperation. She was going to make me cum before I even got to taste, much less fuck her amazing little pussy. Even if she let me let me stick I in her now I wouldn’t last a minute.

I pulled her off my cock and dropped to my knees, putting my face close to hers as she wiped her wet smile with her forearm. “Too much for you, old man?”

“How about you let me suck on you for a while and think about it some more?” Not waiting for permission I lowered my head straight to her pussy, pulling her hips forward while pushing her back onto the couch. It was every bit as incredible as it looked. Her lips were tight and thin, making perfect little lines of flesh that barely protruded. Her little devil tattoo smiled approvingly at me, urging me on. I put my mouth completely over the soft mound of her slit, pressing my tongue into her and releasing her wetness.

She let out a soft, satisfying moan as I probed deeper into her slick hole, getting as far in as the length of my tongue would allow before withdrawing and licking upwards to her tiny, hidden clit. I could just barely feel it beneath the folds of her slim lips, but her reaction let me know I’d found it. I sucked hard against her, bringing it into my mouth and tickling it with the tip of my tongue as she raised her hips up to me and moaned louder.

Her taste was amazing. Clean and musky at the same time, salty and sweet. I was licking away at her with abandon and her warm juice covered my chin. It was a pussy I could eat forever, and I really wanted to make her cum for me. I continued to toy with her clit, bringing her higher and higher, occasionally licking the rest of her to get a mouthful of her sweet, young taste. Her moans and expressions let me know just where she was, and I did my best to bring her along steadily. Whenever I would look up her head was either turned to one side, eyes tightly shut, or thrown back staring straight up, her mouth open and panting, her hands rubbing her breasts through her dress.

Finally, I brought her to where I wanted her, and her soft thighs began to flex against the side of my face. Her whole body slowly stiffened as I drew her clit into my mouth one last time, flicking it hard and steady as her orgasm broke over her. It came on softly and gradually, but once it took hold of her she began to buck heavily with each new spasm. I just held her pussy tight to my mouth, trying to keep it going without giving her too much stimulus. My chin was drenched with the flow of her sweet wetness, and my tongue was savoring every drop of it. I was trying to see how long I could extend her enjoyment when she interrupted me.

“Inside,” she panted loudly. “Put it inside me now. Hurry. Stick it in me while I’m still cumming, please!” She was trying to sit up, pulling her dress up over her head in a cute and awkward manner, struggling to free herself from it yet unable to do it gracefully.

I released her a rose up onto my knees, my cock rock hard and dripping, while she finally managed to toss aside her only bit of clothing. Without hesitation I put it right to the base of her open, slick pussy and eased it in, her tight little lips clinging nicely to it. Within a few strokes I had worked it gradually up to its full depth, watching it disappear until I turned my gaze upwards.

In front of me, enveloping me, was an her amazingly beautiful self: young and curvy and so, so slight of frame. Her tiny breasts barely rose above her chest, tipped with equally tiny dark nipples. The richness of her Asian skin was wonderfully offset by her dark hair and penetrating amber eyes. And I, the luckiest man in the world at this moment, had her all to myself to fuck a much as I could.

And fuck her I did. Unable to contain my lust, I held her hips and fucked her hard, bringing her orgasm back almost without interruption. She was holding her legs up for me, her hands behind her knees presenting as much of her pussy to me as she could, allowing me to drive in entirely to my full depth. I could feel the bump of her cervix with each drive, which drove her to cum harder and harder, until all she could do was hold on tight and shiver as I nailed her into the couch. Her head came forward, her tightened abdomen pulling her upwards, her eyes clamped shut as if in pain. Her mouth was wide open and entirely silent as I fucked her through what must have been a mind-bending orgasm that didn’t let up. Finally, and with a great shout, she put her hand to my chest and told me to stop.

“Oh, fuck!! Please. Wait, wait, wait. Oh my god…” She was panting, holding me at arms length. I rocked my hips a little, still moving myself slightly inside her, unable to fully stop. Her slick tight pussy was too velvety to resist, despite her insistence. “C’mon, please. Stop for a second, seriously.” She was looking up at me with her delicious eyes, and I finally slowed my hips to a stop, then withdrew, placing my cock against her soft fuzz.

“Wow,” she said after a few moments rest. “I didn’t think you’d be that good. And don’t think I’ve forgotten about making your pick. Time’s up. Guess which girl I am and you get to do me from behind.”

She squirmed out from my grasp and crawled along the couch on her hands an knees, her ass facing me. She looked over her shoulders and smiled, cute and mischievous. “Which is it? Guess. Now.”

There was no way I was going to guess high school, because I didn’t believe a girl that young could have this much sexual energy. And I didn’t think she looked quite as old as her mid twenties, particularly after seeing her tight little slit. So I took a shot and hoped for the best.

“College. You’re in college. My bet is you’re a sophomore.”

“Aw, too bad,” she said, continuing to tease me with her ass. “You guessed wrong. No more pretty pussy for you.” She reached between her legs and began to finger herself, spreading her lips for me to see what I’d be missing. “But since I’m a nice girl, and you’re really good at making me cum, I’m gonna let you give it to me anyway. So climb up her and stick it back in, ok?”

Not that I’d really considered not fucking her as an option, but I was glad she at least gave her consent, and in that sense was relieved. And ready now to cum as well. So I climbed up behind her and slipped it right back in, holding her cute little butt firmly in my hands. Almost immediately we were right back to the hard and fast of it, her thighs slapping loudly against mine with each deep thrust, her moans increasing to a continuous drone.

The view was incredibly erotic. Her tiny feminine frame arched back to me, my hands squeezing her round ass, pulling it open to show her dark, tiny hole, which began to pucker at me as her arousal increased, all of it made me harder still and eager to cum. I could feel my cock stiffen in her every time it bottomed out in her, watching her anus flex throughout.

Then she did something that took me completely over the edge. With her face resting against the arm cushion, propped up on one elbow, she reached around with her left hand and slowly inserted her middle finger into her ass hole, easing it in and out to a rhythm independent of our fucking. Watching her anus cling to her finger as it both pressed in and withdrew was more than I could take, and I grew impossible hard and felt my cum begin to swell in my balls.

The combined effect of all of this brought her orgasm back as well, and she started cumming even before I did. She pressed her finger in all the way and held it there as I slammed hard up against her ass, the cum erupting now from deep down and showering the walls of her tight, wet pussy. We were both shouting, hers muffled by the couch, mine filling the room as I continued to explode. My orgasm was huge, and kept on going as I stared at the finger in her ass, feeling every one of her muscles contract again and again.

When things finally began to subside, I held myself in her as long as I could, feeling my cock gradually diminish while savoring the incredible surround of her pussy. Every now and then I flexed another impossible drop of cum into her, until finally there was nothing left, and I’d shrunk to the point of falling free of her. When I did, she extracted herself from beneath me and stood up, reaching for her dress and throwing it back on, letting it settle against her body. As she did this I could see a stream of cum starting to run down her leg, and she reached for it with her hand, wiping it into her palm. She stepped towards me and put her cum filled hand against my chest, leaning forward to kiss me.

“Thanks, you can have this back now. I’ve got to get back before my parents find out I’m not in the room. I’d hate to get grounded.”

I was only mildly surprised, but awed by her young ability. “So it’s high school, huh?” I shook my head a little at how such an amazing lay could come from a girl so young. Somehow the thought of the legality of it never entered my sex-addled mind.

“Yep, you were off by a couple of years. More than a couple actually.” She put her shoes back on and walked to the door. “But don’t worry,” she added before walking out, “you’re not the first one to guess wrong.”

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