Anna's Lesson in Betting

With his arms around my body, he lifts the corner of his cards and quickly glances down. The only reaction he makes to what he sees is slipping one hand between us and two fingers quickly finding their way between my folds, pushing inside of me.

I bend my head and whisper "That good or that bad?"

His fingers curl up and begin to rub my ever special spot. I'd thought James was the only man who could find it so quickly, but clearly I'd found another.

"Do you think I can make you come before this hand is up?" He replies.

I pull back and look him in the eyes and smile.

He moves his thumb between my wet lips until he reaches the exact spot that makes me buck and moan. We both lick our lips, his head drops down to capture a begging nipple in his mouth. He sucks most of it into his mouth and begins to chew while his thumb strokes my clit.

I arch into him, pushing my tits up to his face, giving them to him. Silently begging for him to take more of them. My hips grind against his hand, pushing his fingers deeper inside of me.

"More, oh, yes. Oh don't stop." I beg, my words coming out in sharp, short rasps between breaths. My body quivers against his.

"Are you going to come for me?" He asks moving his mouth to my other tit and sucking it deep into his mouth.

"Yeeessss." My head tilts back and I suddenly remember there are people watching us. The strength of that thought thrusts my first orgasm of the evening through my body. "Ah fuck Tyler, I'm coming."

He doesn't stop; his fingers continue their assault on my pussy as it spasms around his fingers.

"Times up." James' voice breaks through the haze in my mind.

"Who?" Tyler asks releasing my tit from his mouth.

"Your brother."

Tyler turns to his brother and they smile at each other. Rob moves his chair closer to Tyler's. Tyler, keeping his fingers buried inside of me, lifts me with his free arm and turns my body, lowering my head down onto Rob's lap.

"Oh come on." Todd swears. "It's Rob's turn."

"If Rob wants to share her that's his choice." James says calmly.

I reach inside Rob's boxers and pull out his semi-hard cock. It's shorter than I expected but he has a thick mushroom head. I stick my tongue out, licking up his length to the underside of his head. Rob groans and pushes against the back of my head, urging me to get closer to him. I smile and open my mouth wide, sucking him between my lips and using my tongue to massage him as he slides in.

Something between a purr and a moan rises in my throat as Rob's cock fills my mouth, inch by inch till he completely fills my mouth and throat with his hardening cock. His deep, husky groan cracks open another part of me.

"She's enjoying this." Tyler says, his fingers sloshing in and out of my sopping hole. He pinches my clit, drawing my attention back to him and I become completely aware that I have two sets of hands on my body. Fingers pulling at my nipples, others filling me, my mouth filled with cock. I realize then that the walls I put up years ago are easily shattering around me. A sudden high kicks in sending my body into overdrive. I ride Tyler's fingers, grinding my clit against his thumb while sucking Rob deeper using my tongue until I hear, "I'm gonna come."

Rob's body tenses up and he tries to push my head away so he can pull out but I latch on, swallowing every drop of come that erupts from his throbbing cock head. I suck until I'm sure I swallowed every drop he has to offer.

"Fuck Anna." Rob groans pushing me away from his already shrinking cock.

I twist, pushing off of Rob's lap to kiss him hard, allowing him to taste himself on my tongue. I'm on fire, my entire body burning with the desire to take on all six guys. That thought pushes all the right buttons and I shift to settle back onto Tyler's lap where I wrap my arms around his neck and kiss him, nipping at his bottom lip.

"I want to fuck you." Tyler growls in my ear.

"I want you to fuck me too." I groan, sucking his tongue into my mouth. I can't stop the need of wanting him inside of me. The desire to scream out his name as he slams his cock between the slick walls of my tight pussy. My body is shaking, pulsing with need. I bite down on his tongue and grind my hips against the bulge in his pants.

"Jack's turn." James says, breaking our moment.

Tyler swears with a frustrated groan as I spin around and lock onto Jack with a naughty smile on my face.

"What would you like to do with me?" I ask walking over to the tall red head with the thickest legs I've ever seen. Jack's a hockey player and couch that spends hours each day on the ice and his body is proof of his hard work.

With out saying a word, Jack stands up and quickly slides his thumbs under the waistband of my skirt and crotchless panties, sliding them down for me to step out of. He then lifts me off of the ground, laying me down on the poker table with my thighs spread and him between them.

"I guess we're done here." A voice says but I'm too caught up in my own lust to work out who said it.

"Leaving already?" James asks someone but I don't hear a response because Jack lowers his mouth to my soaking wet pussy and slowly licks from the bottom to the top, making my entire body roll up to meet him. I reach down and tangle my fingers in his dark red hair, pushing his face between my thighs.

"Oh you feel so good. OH So good. Oh oh fuck Jack." The rest of my words are lost as Tyler appears above me. My eyes travel down his body and I focus on what he's holding. His cock is thicker, meatier than his brothers but just as long. He gives me a wicked grin before pressing the tip of his bulging cock against my lips. I shuffle back till my head hangs back over the edge of the table. I suck him into my mouth without a second thought and before I have a chance to do anything further, Tyler's hips start thrusting, pushing himself deeper and deeper down my throat. I choke, surprised at how deep he reaches. But he doesn't pull out, he waits until I begin to relax and pushes a little deeper.

I'm so caught up in Tyler and his cock that I've forgotten about Jack. He brings me back to earth by slipping his tongue inside my sloppy hole. I buck against his mouth, causing Tyler to slip past the resistance at the back of my throat. I try to relax and stay calm, feeling tears starting to form in my eyes.

"Shh, relax sweetie." Tyler says running his fingers across my cheeks. "Open your hand." He whispers.

I do as he says and Todd slips his cock into my palm. My groan is muffled, the sound vibrating around Tyler's cock. His body shakes and he groans loudly sending waves of pleasure through out my body.

Jack using all the distractions to his advantage and slips two fingers in my pussy and his thumb, drenched from my flowing juices, pushes into my tight ass, but I am rewarded by his tongue lapping at my clit. With in seconds he has me moaning loudly around Tyler's cock.

"Hey, no teeth." Tyler chides me, holding my shoulders steady as my hips buck and shake from Jack's assault on my clit. "Are you going to come?"

My eyes go wide as I groan again, hoping he'll get the message.

"Then you better hurry up and make me come." He demands pumping his hips faster, fucking my throat. Tears are slipping down my cheeks, my eyes are burning but I can't stop. They are giving me exactly what I want.

It takes all my will power to concentrate on Tyler's cock in my throat, to not think about what Jack's incredible tongue and fingers are doing to my quivering pussy. I'm swallowing Tyler as best I can, my hand quickly working Todd over, who looks like he's about to bust.

"Anna." Tyler groans loudly as my tongue massages the underside of his cock. His hips thrust hard, shoving him deeper still. My body bucks from his movements, my hand squeezing, sending Todd over the top as well.

Tyler erupts deep down my throat just as Jack shatters the last bit of resistance I have left in me. My hips buck off of the table, wrapping my thighs around Jack's head, I take him with me. I swallow all of Tyler's come and suck him as his cock thrusts in and out of my throat.

"Shit Jimmy, she's amazing. Her mouth, her tits, that hot little pussy. No wonder you never come out anymore."

"You haven't even seen half of what she can do." James says as I sit up and push Jack away from my red, swollen lips.

"I'm in." Tyler says jumping off of the table.

"Chad won."

"How?" Tyler asks.

"The three of you quit, Rob had a shitty hand and Chad called my bluff." James offers and we all turn to Chat, who's sitting across the room on the couch. "You interested?"

Chad doesn't answer but I catch him looking at me. My pulse sky rockets as I meet his eyes.

"Lose the rest of the clothes, I want to see you." It the first words I've heard him say all evening.

I stand up and slowly remove the rest of my clothes, leaving on my stockings. My eyes are locked on Chad's emerald green eyes. I saunter across the room, stopping in front of him. My eyes travel from his eyes up to his hair which is black, cut short on the sides, the centre slightly longer and styled in a short Mohawk. My gaze travels down his long oval face to his pink, plump lips, perfect for kissing. He's sexy as hell, I think to myself.

Below his black button down shirt I spy the dark lines of tattoos; I bend over, leaning forward and unbuttoning his shirt. My hands shake as his shirt parts.

"You're nervous?" He asks giving me a confused look. "Why?"

I push the shirt from his chest and suck in a breath when his skin comes into view. His chest and arms are covered in intricate tattoos and seeing them makes my mouth water. I bite my lip and look up into his eyes.

"What?" He asks.

I lean into him and plant a soft kiss in the center of his chest, directly between his perfectly chiseled peck.

"You don't have to do this you know."

"I know." I whisper, kissing my way across him. "But I really, really want to."

"Why?"

"You're beautiful, complex, I want to know more." I sigh and straighten up. "Can I kiss you?"

He looks into my eyes and we stare for a few moments before his lips turn up at the corners just enough to give me permission.

The moment our lips meet the world around us dissolves. There's nothing in the room but he and I. My hands slide down to his jeans, unbuttoning his fly one button at a time. He lifts his ass and in a flash his jeans are down around his knees and I almost come when I see he doesn't have any underwear on. He wraps his strong arms around my thighs and he lifts me off the ground and onto his lap.

He silently slips a condom down his thick, hard shaft between us and before I even have a chance to focus on what's happening, he's sliding into me.

"Holy shit." I say through clenched teeth.

"Is this something you do often?" His voice is deeper now, his own lust taking control. Which causes me to shiver.

"Fuck James' friends? Never," I whisper pushing down until Chad's buried deep inside of my wet tunnel. "James likes when I show off and the idea of someone watching has always been a turn on for me," I explain before kissing him again. "Do you make a habit of fucking your co worker's girlfriends?"

"Never but I couldn't turn you down."

"No? Why not?" I flash a sly smile.

His head drops to the side of my face so that his lips are near my ear. "Turn around so you can watch them watch us." He whispers.

His words cause me to clench around his cock and my body to arch into him. Without saying a word I follow his command, standing up and spinning around to face the room.

My eyes move from familiar face to familiar face as Chad guides himself back inside of me. I moan loudly and lock eyes with James. The look on his face says everything. I smile at him, spreading my legs wider. I look down and see what they see. I think, it's the most beautiful sight I have ever seen, as I watch Chad's cock slide deep inside of me slowly, over and over again.

"Play with your clit." Chad whispers in my ear. I quickly reach between my thighs and press two fingers to my hard clit. One of his hands moves to my breast and he begins to pinch my nipple.

The sensations start overwhelm me and I back off of my clit, afraid of coming too soon. I'm not ready for this to end.

"Don't' stop."

"Not yet." I tell him.

Chad drops his hands to my thighs, pulling them further apart, stretching them as far as they can go before reaching between my puffy pink lips and flicking my clit. It only takes a few seconds before an orgasm explodes inside of me. My toes curl, my fingers dig into his thighs and he bites down on my shoulder.

"Fuck. Me. Chad." I scream, forcing my eyes to stay open. Forcing myself to watch them, watch us. Watch me.

All five guys have their cocks out and are jerking off with wild abandon.

"Do you want to bet how many times I can make you come before I come deep inside of you?" Chad asks, his voice husky and thick.

"I think I'll I'd better stay away from betting for a while, look at what it got me into here." I say, my eyes rolling up and my body shuddering against his.

"Aren't you having a good time?"

I laugh out loud and realize for the first time in months I'm having sex and not thinking about anything else. No problems, worries, concerns. I'm completely focused on what I'm feeling, only the pleasure and nothing else. Something I used to do with James, but over the past three years it has gotten lost in the every day rush of life.

"What bet did you lose to get here?"

"I bet that the Hawks wouldn't make the playoff's." I say, embarrassed by how ridiculous it sounds.

I glance over at James and see he's not only jerking off, but he's smiling at me knowingly.

"Four times." I yell.

"Six." Chad says.

"No way." I laugh. "I've already come four times tonight. Six is the most I've ever had in one night, besides my clit is way too sensitive for much more." He flicks my clit again I swallow a scream, "Fuck! What are the terms?"

"I win you go home with me tonight."

"And if I win?"

"Your call." He groans as I clench around his hard, pulsing cock.

"I win, you stay, ah fuck Chad." I'm gasping for breath trying to hold back an oncoming orgasm.

"I'll stay here and you can ride my face for as long as you want." He suggests.

"Sounds like a win win to me."

"Does it?" He growls, his hand slaps my pussy sending another orgasm crashing over me.

"Oh fuck, holy shit." I'm breathless and the world around me is starting to spin. "There's no way I'm going to make it to six."

"Sure you will. Only five more to go."

"Never going to happen."

Chad stands up, taking me with him. He sets me on the floor, "Get on your knees."

I quickly push myself up onto my knees, shoving my ass into the air towards him. He slams into my wet, red used pussy, his fingers returning to my clit.

"You shouldn't bet anymore." He suggests, pumping into me hard and fast.

"No?" I say with a groan.

"I never said what I was taking you home with me for," He smacks my ass hard, "I could tie you up and do all kinds of nasty things to you."

"Oh God," I buck and try to push my legs closed, to stop him but he barks at me, telling me to keep my legs spread. He slaps my ass again. The pain is intense, almost too much but another wave crashing over me.

"Only four more to go Anna."

My hips slam back to meet every thrust and I keep waiting for the tell-tale signs of his orgasm but they aren't showing.

I laugh again, my eyes closing. I'm so caught up in how funny the evening has gone that I don't know what's going on around me. But then I see James retreating from beside us, a small smile on his face.

"Oh fuck me." I yell, my head jerking up, my eyes going wide. I look down between my legs and see Chad holding my favorite vibrator between my lips. I love it because it's not overly strong but it's perfect for multiply orgasms.

In that moment I realize that every thing, from my silly late night discussions about what turns me on, to James bringing up the idea that we should bet, to him licking me with is wickedly talented tongue when we made the terms, to the suggestion of who would be involved, was all leading to this.

To right now, this moment, to Chad fucking me doggie style while the other guys watch.

I freeze, wondering at the depth of the plan, were they all in on it?

"Are you alright?" Chad asks. His hot breath dancing across my bare back making me shiver.

The sensation of this breath alone urges me on. Another orgasm takes over my body and I realize that he's going to win. My body slumps, the vibrations are too much as the forth orgasm slams into me sending my body into a state of pleasure-pain that's almost too much for me to take.

"Chad." I scream loudly, my arms giving, my body caving in, my head falling forward to rest on the cool, hard wood floor. I'm exhausted. My body hurts, it's slick with sweat and other fluids but I couldn't stop him even if I wanted too.

He doesn't say a word but suddenly it all stops. He's no longer inside of me and my vibrator is gone. He flips me over so that we're facing each other.

"I want to see your face when you lose," He grins at me and slips back in. "Do you want to hold this?" He holds up my vibrator."

"We both know you don't need it." My voice is quiet, exhausted.

"Are you giving up?" He teases me.

I shake my head, "I can't fight it, you were right." My voice is shaking and breathless as he slides back into me.

"What if I give you the advantage?"

"How?"

He rolls us both over, putting me on top.

I stare down at him and smile, he's all but given me the win. In this position I can get him off in a matter of minutes and he still has two more orgasms to go. I smile down at him wickedly and begin grinding my tight, wet pussy around his thick cock. Sucking at his cock with my slick walls, using every bit of knowledge I've learnt about fucking to my advantage.

He groans, using his hands to push me harder into his pelvis. And before I realize what he's doing a new sensation takes control of my body. It's too much to fight, and I want it. I'm craving it. My hips buck, my body bending to just the right angle so that his cock rubs against my g-spot.

"Oh fuck no." I cry out as a boiling wave crashes over me.

"One more." He groans, my hips are pumping harder, he's holding me above his body so that his hips can thrust up into my hard and fast.

I know it's too late. I know that my last one isn't far away. I feel it building in my body. Starting in my toes and quickly rushing up my body and it's going to be a huge.

"Oh fuck. Harder, harder. Yes, oh God yes. Oh faster oh right there, Oh oh Oh God, oh oh oh oh oh a a a Chad, fuuuuuuccccckkkkkkk."