9/9/09

"On a Wednesday???"

At first, Jenny wasn't much impressed with my idea to go out that night after work to celebrate.

"Well, yeah, there's not much point in celebrating 9/9/09 unless we actually do something, well, on 9/9/09! Come on, it'll be fun. It's been too long since we've gone out - let me call Anna too, it'll be the three of us, just like old times!"

I knew Anna would be more into the idea - not only was she usually the one trying to get us to go out for drinks, but I knew she'd be into my idea - using today's calendar oddity as an excuse to party. Even if she would tease me later about falling for all that numerology stuff. Hey, what are friends for?

"Oh, heck yeah, absolutely! I'll meet you there at 7," Anna replied when I got her on the phone and pitched my idea. "That'll give us time to go home first, and get dressed up - to the nines!"

I chuckled at her joke, thanked her for playing along, and called Jenny back. The second time around, she didn't take much convincing. It was all set. We'd meet at our favorite watering hole, enjoy a few drinks, and see what action we could find.

The three of us - Jenny, Anna, and I - had become fast friends when we met in college, shared an apartment together after moving out of the dorms for our senior year, and were doing our best to stay in touch a few years later, now that our lives had taken us in three different directions. Three different employers, three different apartments in different parts of the city. Over the years, we'd supported each other through challenges with family, school, and careers, not to mention various relationships. Right now, we all happened to be single, which is why I'd frankly been looking for an excuse for us to go out again as a trio. It was about time we all got a little action - and if we didn't happen to find that on a Wednesday evening, at least we'd have a good time.

It wasn't unusual for us to get a lot of attention when we went out together. Jenny has the body of a supermodel - tall and lean, with unbelievably perfect legs, and long blonde hair - natural, of course - and big blue eyes. Anna is equally gorgeous, if a completely different type. She's petite - a good six inches shorter than Jenny - but curvy, with olive skin, deep brown eyes, and thick wavy black hair. For some reason - maybe because we're all so different - we were never jealous of each other. I mention that as I share the fact that Anna and Jenny had always agreed that I was the 'hottie' of the group.

I'm 5'6", with a lean, firm body - and, I've been told by more than just a few guys, luscious tits. I have natural red hair which I wear long, half-way down my back, freckles across my nose, and big green eyes. Oh, and my name's Maxine, by the way - but everyone calls me Max.

We were enjoying an Indian summer, so even though it was September, with the stores already stocked for Halloween, we were dressed as if it was a warm evening in July. Jenny showed up in a blue, flowered sundress that matched her eyes, fitted around her torso with a full, flowing skirt. Anna was showing off her gorgeous dark skin in a tailored summery silk suit - a red sleeveless vest and matching shorts. I decided to go with an ivory-colored silk blouse, leaving the top two buttons undone, perfect-fitting jeans, and heels higher than I would normally wear.

We greeted each other as we arrived, found our usual table, and ordered a round of drinks as we chatted, catching up since we'd last seen each other a few weeks back. For the first hour or so, we behaved ourselves, our conversation centering around work, old inside jokes, and the fact that the bar was completely devoid of any action on a Wednesday night. Before long, though, we ordered another round, and our tongues loosened. We really were good girls, but part of our fun when going out was always to pretend to be a bit naughtier than we really were, and see what we could, um, bring up among the men in the bar.

"Alright, girls," I said loud enough for those around us to hear, "I think we should decide what we're going to do tonight to celebrate 9/9/09. You realize, right, that it's the last time for almost a century that we'll see repeating dates like this?"

"Yeah, so?" Jenny polished off her second beer and ordered another.

"Well, so, I was wondering - who's up for a nine-incher?"

Anna smiled, and chimed in, "or maybe a nine-way?"

A few heads began turning our way, and we chuckled to ourselves as the guys who were there with their girlfriends either had to move further away from us, or surreptitiously find an excuse to move closer.

"Or, if you're into the whole BDSM thing, there's always a cat o'nine tails," Jenny added.

A guy at the bar practically gave himself whiplash as he turned to look at her. She simply raised her glass and gave him a wink. We broke down into hysterical laughter.

When we recovered, I continued with our fun, using my Blackberry to visit UrbanDictionary.com. "Let's see what else I can find that we might try... ooh, have you ever heard the term 'niner shiner'? Apparently that's a whore or slut, kind of like you, Anna!"

"Hey, come on," she replied in mock horror at my racy comment.

"And hey, look at this," I said, as both of my friends leaned in to see my cell, "a detailed description of exactly how to have a nine-way!"

Jenny read aloud, much to the amusement of several guys at the bar, "quite possibly the most sex anybody can have with a woman at once and keep it satisfying for everyone. This little-known sexual "position" consists of eight guys and one woman for a total of nine people. The penises are allocated as follows: one in her mouth, one in her vagina, one in her rectum, one for each of her hands (making two), one for each of her feet (making two as well), and finally, one between her breasts. Needless to say, this requires some careful manoevering among the men in order to prevent knees and elbows from accidentally ending up in people's faces..."

Her voice trailed off, drowned out by our laughter. None of us noticed as the man approached our table, as we continued to collapse in laughter at the image of all these people trying to avoid elbowing each other in the face as they attempted to create a wild orgy. She managed to finish the silly definition - "as long as all of the above mentioned holes/surfaces are filled, it is an nine-way" - just as I looked up and noticed the man standing directly behind Anna, smiling in clear enjoyment at our enjoyment, and clearly not intimidated one bit by our feigned naughtiness.

"Well, hello there," I said, smiling back at him, "I'm Max, and these are my friends Anna and Jenny. Is there something we can do for you?"

"Well, I couldn't help but overhear your conversation, and I'm thinking there's actually something I can do for you."

"Oh, really? And what would that be?" I waited for him to shift his gaze to Jenny or Anna for long enough that I could check him out. He was undeniably handsome, with an athletic build. He had clearly come to the bar that evening directly from work, as he was wearing a beautifully tailored suit. Talk about dressed to the nines. His five-o-clock shadow was catching up with him now that it was after 8pm, always a good look on a sexy guy. The seasoned lines around his deep blue eyes, and his salt-and-pepper hair, made me guess he was in his early 40s, although in he clearly had more than enough confidence to approach our table of 20-something hotties.

Jenny interrupted before he could answer, "I don't see you here with five other guys, so presumably you're not going to proposition us with a nine-way?"

"No, nothing so crass. Besides, that many guys would just get in the way when I'm pleasuring a young lady so lovely as yourself. My name's Jesse, by the way."

Jenny was taken aback by his forwardness, so Anna took up the slack in the conversation. "Alright, so what then? What can you, all by yourself, do for us lovely young ladies?"

"Well, it was a pleasure to hear that you're out celebrating 9/9/09, just like I am. I'm surprised more people aren't taking advantage of the excuse to get out. But perhaps it's because they can't imagine the possibilities quite as well as you or I. If you're up for it, I can offer you the nine-incher you're so curious to experience."

"Just her, or all of us?" I figured he was bluffing, so I might as well be the one to call it.

"Well, that depends. I'm willing to go the whole nine yards, keep the three of you on cloud nine for the rest of the night. But I get this feeling you're just bluffing. I'm not going to invest my evening in this adventure until I'm sure you're for real."

Wow, now he was the one calling my bluff. I decided to go for it. I wasn't sure whether Jenny and Anna would go along with me, but hey, if they didn't, I'd have this guy all to myself for the evening! I hoped they would, though - after all, going off with a stranger felt a bit safer if the three of us stuck together.

"Oh, I'm for real, I assure you. And my friends are too, right girls?"

"Um," Anna began uncertainly, "sure, what the hell. You in, Jenny?"

"If you both are, I'm not missing out!"

"Just one thing, Jesse," I looked deep into his eyes, "my pussy has nine lives, just like the saying goes. Do you think you can handle that?"

"Ah, a challenge from the lovely redhead. I thrive on challenge, it'll be my pleasure. Let's go."

"Oh, jeez," I whispered to Anna, "what has my big mouth gotten me into this time..."

We walked with him out to the parking lot, agreed to follow him to his apartment, and watched him get into his dark green Jaguar convertible with a vanity plate that read 'CHECKM8'. Hmm, a sign? We looked at each other in a bit of shock, a bit of uncertainty, but quickly agreed that we might as well see where this would lead, and followed him, a line of four cars taking the few blocks to his apartment slowly, carefully, as we were all a bit on the tipsy side.

His apartment was stunning, a top-floor unit in an old but recently restored building with high ceilings, hardwood floors, and lots of gorgeous detail. He told us to make ourselves comfortable on the sofa as he turned on a few lights and lit a few candles. He'd be right with us, he said.

"What the hell was that back there, Max, the pussy with the nine lives? You realize you'll never live that down, whether it turns out to be true or not?!?"

I smiled broadly. "Come on, Jenny, don't you realize it's a win-win either way? If he can actually bring me that much pleasure, and if I can actually manage to cum nine times before collapsing in exhaustion, cool. If not, it still sounds like a pretty hot evening, don't you think? Come on, we got this far, let's just see where things lead."

"Um," Anna broke into the conversation, after being silent from the moment we left the parking lot, "aren't you guys worried that this might be a little awkward? I mean, I love you guys, but what if..."

"Sex ruins the friendship?" I laughed at her, then, realizing she was seriously concerned, changed my tone. "Don't worry, Anna. This doesn't make us lesbians, you know - we're just three friends about to enjoy an evening with the same man."

Before she could respond, Jesse returned and sat down on the coffee table, facing us. "So, you girls ready? Come on, admit it, you do this all the time, right? The three of you pick up a guy and have your way with him?"

"No, honestly, Jesse," I replied in all seriousness, "this is a first for us. But if you've seriously got nine inches there," I reached out and stroked his crotch as I talked, "and you're up for bringing me to multiple orgasms, we're good enough friends to try anything together!"

"Alright, then! But hey," pushing my hand away, "if I'm going to come even close to meeting your challenge, we're going to start with you, not me. Jenny, Anna, follow my lead."

He put his hands on my knees, uncrossing my legs and spreading them apart. His hands moved down to my feet, pulling off my heels and tossing them aside. My friends were still just sitting on either side of me, unsure of what to do next, but as he continued to undress me, they joined in, the excitement of the moment outweighing the awkwardness. They worked together to unbutton my blouse and pull it off, and then began massaging my tits through the fabric of my bra. After massaging my clit through the fabric of my jeans, Jesse now worked to pull me out of them, as Anna reached around to unclasp my bra. Soon, I was wearing nothing but my panties, with three fully-clothed people surrounding me, fondling me.

Embarrassed as I am to admit it, I have to share, for the reader doing the math, that I came almost immediately when his hand finally pushed aside the fabric of my panties and he touched my pussy lips directly. It must have been the combination of sensations that pushed me over the edge so quickly - the accumulated excitement of the evening, the fact that Anna and Jenny were each sucking one of my tits, and the expert touch of his big, strong hands. He kept stroking me as I came, my juices flowing freely. After a few moments, he switched hands, giving Anna and Jenny each an opportunity to lick my juices from his fingers, breaking any last bit of ice that might still have remained between us.

His fingers now began to reach inside of me, and I groaned with pleasure, sliding lower on the sofa to give him better access as my friends continued to focus on my breasts. He began thrusting one finger in and out of my dripping pussy with a regular rhythm, before finally adding a second finger, and then a third. I pressed against him with each of his strokes to increase the depth, and exploded in another orgasm when he began flicking two fingers of his other hand rapidly across my clit. I screamed out until Anna silenced me with a kiss, a moment that might have felt strange if I weren't so overcome with pleasure. Instead, I eagerly played with her tongue as she thrust it into my mouth and I rode out the waves of pleasure.

Once again, Jesse just continued his attention to my pussy, pushing me steadily towards another climax rather than allowing me to rest. Not that I was complaining. It was now his tongue, rather than his fingers, that explored my clit and pussy. As I writhed beneath him, Jenny reached over me to kiss Anna, and I fondled their tits, which were meeting in front of my face. Their moans now joined mine, and after just a few more moments, I came once again, this time covering Jesse's face with my juices.

He stood up, red-faced and hair messed, and said, "How's that for a start, Max? Why don't you rest a bit while I pay some attention to your beautiful friends here."

"Whatever you say, Jesse," I replied breathlessly, still recovering from my latest climax. I stood up, finally removed my panties, and stepped back to watch as he went to work on them. I did need a break, but I also knew how exciting it would be to watch the three of them together. Anna and Jenny stood up and helped each other out of their clothes, soon standing naked before each other and Jesse, who sat between them on the sofa.

My two gorgeous friends embraced, pressing their naked bodies together and rubbing against each other, as Jesse placed one hand on each woman's pussy and began fondling them. It wasn't long before they were both squealing with pleasure, their occasional moans stopped only when their lips joined in a passionate kiss. Their threesome went on like this for a few minutes more, before I couldn't hold back any longer, and tried to join in.

"Ah, Max, so you're ready for more action?" Jesse smiled up at me from the sofa, continuing to finger my friends. "Well then, why don't you all join me in the bedroom."

He led us down the hall, and as soon as we arrived, he asked Anna and I to climb up on the bed. "Nothing I like more than watching two women pleasure each other in a 69 - you ever tried that?"

Anna and I looked at each other, old friends with eyes filled with lust. Neither of us had, with anyone, much less each other, but we weren't about to refuse. As we worked ourselves into the position with Anna on top, Jesse quickly undressed down to his boxers, and motioned for Jenny to kneel in front of him. A few moments later, we heard her gasp, and both looked in her direction.

"Yikes, I think you really are nine inches!"

"What did I tell you? Now, take me into your mouth."

He moaned in pleasure, and Anna and I went back to work, gently exploring one another with our tongues. As Jenny struggled to take even half of Jesse's cock into her mouth, he gave Anna further instructions. "Remember, Anna, I'm going to need everyone's help to give Max what she wants tonight. I'm counting on you to make her cum - but let me give you a little help."

He was standing close enough to the bed to reach out and touch Anna, and he gave her a couple of firm slaps on the ass followed by a gentle kneading of her flesh, then a few more slaps. With each stroke of his hand, Anna gasped breathlessly and worked her tongue and fingers even more furiously on my pussy. His approach worked, with Anna's excitement spurring her to work faster and harder, which in turn led me to moan into her pussy as well. Before much longer, we were both writhing in pleasure - my fourth orgasm of the night, and Anna's first - we clung to each other, continuing to lick gently even as we rode out the final waves of pleasure, before finally collapsing to the bed, spent.

"Nice work, Anna! Oh, and you too, Jenny - look how hard you've made me!"

Anna gasped now as she looked up and saw his hard cock, free from Jenny's mouth for the first time. "My turn," she exclaimed gleefully, and climbed off the bed and down to her knees in front of him.

"Wow, gotta love that enthusiasm! OK, Jenny, I'm counting on you to deliver another one for Max! How about another 69 for my... Oh, god, Anna, that's incredible!"

Jenny and I both watched as Anna displayed incredible skill in taking Jesse's cock almost entirely into her mouth, just beginning to gag at about 7 or 8 inches. Jenny and I sat up on the bed and watched for a few moments, awed by our friend's hidden talent, before the hotness of the situation finally got to us and we couldn't resist positioning ourselves to eat each other out. I was determined to bring Jenny pleasure by applying what I'd learned so far that evening about going down on another woman - much to my delight, I had her moaning in pleasure after just a few moments.

As I nuzzled her clit and thrust two fingers in and out of her pussy, Jenny erupted above me, covering my face with her juices and crying out with language I'd never heard from my friend. "Shit, yes, Max, that's so hot! Keep fucking me with your fingers, yes, yes, yessssssss...."

When she could no longer speak, and as she began to recover from her climax, she wrapped her lips around my pussy and sucked, then grabbed my ass cheeks in her hands to lift me up and began thrusting her tongue in and out of me, over and over again with unbelievable endurance, until I couldn't hold back any longer and finally came.

I was so spent at this point in the evening that I almost didn't notice at first, but Anna was simultaneously bringing Jesse to a climax. When Jenny finally climbed off me, and I sat up, I was treated to a great show as Anna was taking Jesse entirely into her mouth in long, slow strokes. As he approached his climax, he began thrusting faster and more shallow, before finally pulling out entirely and covering Anna's beautiful dark skin with a huge load of cum. He collapsed to the bed and watched as Jenny and I gathered around Anna and licked every last bit of cum off of her, each of us getting to enjoy a bit of Jesse's taste as Jenny and I shared a bit of his cum with Anna in kisses.

After a few minutes of watching us, Jesse was once again stroking himself and motioned for me to join him on the bed. Jenny and Anna watched as Jesse brought me into a 69 position once again. I lay flat on the bed, my legs spread wide for him, and he climbed on top of me, immediately burying his face in my pussy and presenting me with his hardening cock, which I took into my hands and began fondling while I licked his balls.