5 comments/ 60560 views/ 16 favorites Anna's Lesson in Betting By: persorosa *I'd like to thank LaRascasse and SD for their support and editing skills. XO to both of you.* * "I can't not believe you're going to make me do this," I say, pouting. "You lost. Time to pay up." James smiles as the fear grows inside of me. "You're going to have fun stop freaking yourself out." "James I know I agreed to this but," I spin around looking directly at him. My tall, skinny James. With his short brown hair and mischievous gold eyes. "Anna, you suggested this." "In a moment of weakness." "Weakness?" He grins, moving towards me. "You know I would agree to just about anything when you're-" "When I'm what?" He raises an eye brow at me. "When your tongue is inside me." I say turning away from him in an attempt to hide my embarrassment. "Baby this was not my idea. I agreed to it only because I know how much you want it. And ONLY if you lost the bet and you did. Better finish getting ready the guys will be here soon." "Oh no you don't. You suggested it and then used your tongue and my own body against me." James laughs and pulls me to him, hugging me tightly. "Do you want to call it off, you can still back out?" I know he can see the answer in my eyes, just as I feel it in my body. "You can do this Anna. You don't want to disappoint me do you?" "No. But..." "No buts relax and finish getting ready. I promise it's going to be fun," He kisses my forehead, which makes my heart melt. "Hurry up." He laughs, slapping my ass. "Ahh," I rub my sore cheek. "You'd better hope this doesn't blow up in your face." I mumble under my breath. "It won't." He calls after me. "Shit," I say fifteen minutes later, taking in my reflection in our full length bedroom mirror. My large nipples are barely hidden beneath a sheer white peasant shirt that hangs loosely around my upper body. Over the sheer shirt I'm wearing a tight black underbust corset which laces up the back with black ribbons, the boning causing my tits to look youthful and perky again. As well as a black mini skirt and black crotch-less panties. My thighs are covered with black silk thigh highs and garter belts. To top it all off, four inch black kitten heels. I take a deep breath and walk out of our bedroom silently praying that I have the guts to go through with this. "Wow." I enter the living room to a round of wolf whistles. There is no mistaking the deep clenching of my body. I'm wet and the night has barely begun. "Thank you Rob." I smile nervously and glance over the room. All of the guys are present. James and I agreed before hand that they would start off slow, but now that the five of them are standing in our living room, staring at me in my slutty get-up, I'm starting to worry. Rob and his twin brother Tyler, as well as Jack, are fraternity brothers of James. Todd and Chad are his co workers from the ad agency. The six of them have been getting together once a month for the past year for poker night and tonight, rather than go out with the girls as I normally would, I'm their, well I'm here instead. "What can I get you boys to drink?" I ask softly as the guys settle into the first hand. Each of them places their drink order and I disappear into the kitchen. "You okay?" James asks, from behind me. "Do I look okay?" I ask moving away from the counter and spinning to show off the full view of my outfit. "You look good enough to lick, uh I mean eat," He grins at me. "The guys agree." I look down at myself and sigh, "I look ridiculous." "Baby you look perfect, as always. You're supposed to be having fun," James says walking over to me. "Take a few shots and be brave. You want this, try to remember that." His voice is filled with love and affection, which helps calm me. "Better?" He asks. I nod and give him a weak smile. "By the end of the night you're going to be so happy you did this. I promise," He smiles and kisses my forehead. "Now get out there and serve my friends." He winks returning to the table and the game. Taking a deep breath I grab the bottle of whiskey and pour myself a shot. I shoot it and quickly follow it up with a second. "One more for the road." I say pouring a third shot and shooting it. Before picking up the tray I give my nipples a few quick pinches but they really don't need it. The anticipation of what could happen tonight has them throbbing and hard. I pick up the tray and carefully head out of the kitchen. Our living room, which usually feels comfortable, seems to have shrunk with the addition of the poker table and all the chairs. I take a quick deep breath and with my eyes cast down I silently walk up to the table. Six pairs of eyes follow my every move despite my best effort not to interrupt their game. One by one I pass each guy their drink until my tray is empty. I turn back towards the kitchen, catching a quick glimpse of myself in the mirror. My nipples are hard and obvious in the soft folds of the sheer material, my cheeks are flushed and my skirt seems to have flipped up in the back. I quickly push it down with the back of my hand and hurry into the kitchen. I fall onto one of the bar stools near our island and drop my head in my hands. "What the fuck am I doing?" I whisper to myself. Reaching across the island, my fingers barely make it to the bottle, I stand up and grab it by the neck and I down more than I should but the slow familiar burn calms my nerves. The boys are fast drinkers which has me thinking I'll need to replenish their drinks soon. While preparing the second round I pull out an extra set of glasses and toss some ice in them. The second trip around the table is a little easier. I focus on taking their empties and delivering new drinks and not on their eyes, though I can still feel them on me. I ignore them and focus picking up one glass at a time. Once my tray is filled with empties and the boys have their new drinks, I head back into the kitchen. I wash each glass and set them up for the fourth round. "Anna?" James calls from the living room. "Bring us that bottle of Jameson." I finish up the third tray of drinks but leave it in the kitchen, silently hoping they aren't slamming them back that quickly. I grab the Jameson; six shot glasses, walk back into the living room and stop right behind James. "Come here," His voice is barely a whisper. I step next to him and wait. "Pour the shots." James motions to the small space open next to his chips. I place the shot glasses on the green velvet and open the bottle. To steady my hands I bend forward and very slowly begin to pour the first shot. Perfect. I smile to myself and move onto the next one. I move to pour the next shot when James starts at my knees and takes his time teasing his fingers up the inside my thighs. He gets to the top and starts again on the other leg. My body shivers and I have to pause in pouring the shot. I wait until he removes his hand then continue. This time he grabs my hot, throbbing pussy. I gasp and pull the bottle up just in time. "Careful Anna, don't spill on the table," He says with a laugh and begins rubbing his fingers between my already swollen lips. "Are you almost done?" He teases, one of the guys laughs and I look up to see Rob directly across the table from me. His eyes glued to my cleavage, despite myself my body shudders and I'm all too aware of the hot liquid spilling onto James' fingers. My eyes drop back to the shot glasses and I try to concentrate on pouring the final four shots but James, who knows my body almost as well as I do, knows exactly how to move his fingers to distract me. With in seconds he has my hips rolling back to meet his fingers and he's teasing my clit with the perfect amount of pressure to pull low moans from my throat. "Anna the guys would like their shots now." "Yes James." I whisper and try to focus on the task at hand. My hands are shaking almost has hard as my thighs but some how I manage to pour the last four with out spilling a single drop. "Pass the rest of them out." He says once I've placed his shot in front of him. He removes his fingers from between my soaked thighs and holds them up for me. I know exactly what he wants me to do but I'm frozen. "Anna we have a game to play." His voice isn't cruel but firm. I lean down and open my mouth, sucking his fingers into my mouth. I lick and suck them clean as quickly as possible and then begin passing out the rest of the shots. Once each guy has their shot, they shoot them back and return the glasses to the table. "Refill em and leave the bottle on the table," James says, "Then bring some snacks out." I nod, even though none of them are looking at my head and follow his instructions. With out a single word I slowly work my way back around the table pouring each guy another shot. Back in the kitchen I work on putting the snacks into bowls, as well as the various dips I spent the day preparing as James' words played in my mind. "I win, you're not only to dress as I choose for our next poker night but you will serve my friends in any way they chose, throughout the evening. You'll be theirs to look at, theirs to touch, you'll do as you are told and you'll love every minute of it." "I can not do that." "Yes my sweet slutty girl you can and you will. We both know you want this." "But," "No buts, you told me you wanted this and I'm providing the perfect setting to take it, just on my terms." "So, how will it work?" I asked in a quiet voice. He smiled, "I'm glad you asked. The winner of each hand can use you however they want until the next hand is over." "However they want?" I shivered. "Yes Anna, however they want." A shiver down my spine brings me back to the present and I finish with the snacks. In the living room, I begin setting the snacks between the guys. I'm starting to wonder if any of the guys are going to take James up on his offer to touch me when ever and however they want when Rob, with his eyes glued to his cards, reaches out and pinches a nipple. It catches me off guard; the pressure is hard enough to make me moan as his fingers squeeze down on my sensitive flesh. Following his brothers lead, Tyler reaches out for my other nipple. The two spend the next few minutes twisting and pinching my nipples until I'm certain they are hard enough to cut through our living room window. Grins cover their faces as they look to James, he returns their grins with interest, leaning back in his chair. They continue for a couple more minutes till I meet James' eye, he can see my desire, can see that I want more. "My glass is empty Anna." He says pointedly. Rob takes his hand away, followed quickly by Tyler. I groan in frustration and return to the kitchen to grab the next round of drinks. With in the first two hours, the guys have downed four rounds of drinks and two shots. They decide to take a break before they start a new game. Three of the guys step outside for a smoke, while the other two use our bathroom. Walking into the living room to clean up a little, I expect James to be in there but he isn't. I quickly collect empty glasses and trash and bring them into the kitchen. I'm at the sink washing some dishes when James joins me. "The guys want to eat before we start the next game." He says nipping at the sensitive skin on the back of my neck, sending chills up and down my spine. "The pizzas are in the oven, they only need a few more minutes. I'll bring them out as soon as they are done." James smiles and leans down, kissing my lips. I return his smile and finish up with the dishes. I carefully remove the pizza from the oven, before sliding them onto a few serving platters we borrowed from a neighbor. I'm practically attacked before I get near the table. Rob grabs a couple slices, Todd a few more, emptying one platter in a matter of seconds. All six guys find seats around the room, either on our couch or the floor while they eat. I stand off to the side as James and I had already discussed, so each of them could enjoy the view. I try to keep my eyes on James as the guys eat. Too afraid to see what the rest of them are looking at but I can feel their eyes on my body, causing me to squirm and blush and they devour their pizza. I am normally a confident woman, but standing around in this outfit with six guys unabashedly staring at me brought any and all body issues to the surface. I can't seem to stand still, shifting from one foot to the other as the tiny voices begin racing through my mind. Do they like what they see? Can I go through with this? Do they see what being almost thirty has done to my once perky body? Do they know what's underneath these clothes? Do they want me? James finishes first and leaves me alone with the guys for a few minutes. Without him to focus on, I allow my eyes wander over the room. My inner walls clench when I catch the gaze of each guy checking out some part of my body. Me breasts, ass and legs all capturing at least some of each of their attentions. All accept for Chad. I've only met him one other time, he seems oblivious to my near naked state, affecting an air of calm indifference, like its nothing out of the ordinary. It piques my curiosity, while providing a reprieve from the other hungry gazes. "James." I squeal when he wraps his arms around my waist. He hand snakes up pulling the neckline of my shirt down enough to show my tits almost to my nipples. His lips make there way through my thick dark blonde locks to my neck. He sucks and licks me in all the right places sending my senses into overdrive. I grind my hips back into him, goading him to continue. He knows me well enough to read my message loud and clear. James doesn't hesitate; one hand slides down the short length of my skirt, lifting it up as he cups my pussy, sliding a single finger between my begging lips, the other hand pulls the front of my shirt down until my tits pop out. He groans, pinching my already hard nipples. My body responds by instinct, my back arching against him and pressing my pussy against his finger, urging him inside. "Anyone else want a little dessert before we get started?" He asks before biting down on my shoulder. "She tastes like heaven." I'm not at all surprised when Rob drops his plate on our coffee table and walks over. He hit on me the night James introduced us, neither Rob nor James know that I heard Rob swear that night that some day he'd fuck me. But thick jocks have never been my thing, James's skinny, tight body is what makes my knees go weak. Though tonight it looks like Rob may finally get his wish. Rob stops in front of me, kissing me gently. His lips are thicker than James, his kiss is sweet. His hands slide down my sides, roaming freely over each curve until he reaches my hips. He grabs a handful of my ass and pulls be closer to him, grinding my hips into his. His tongue slips between my lips, teasing my tongue. I'm so caught up in his kiss that I don't notice his hands moving from my ass until he slips two fingers between my wet pussy lips and deep inside of me. I pull back from his kiss, but his free hand keeps me from pulling away completely. I buck against his hand and when his lips meet mind again I bite down. He smiles and pulls back. "You're soaking wet." Rob whispers, slowly removing his fingers before slamming both back inside of me. I grab onto his large, linebacker shoulders to steady myself. Again he slowly slides his fingers out and just before his hands leave my wet, puffy lips he runs the tips of each finger over my clit. "Ohhh God." I moan sinking my dark red nails into his massive shoulders. "Round two." He says to the guys, but his light brown eyes never leave my face. The sound of them moving across the room fills my ears but Rob holds my attention. "Come sit with me." Rob whispers before joining them. I nod and smile sheepishly at him, a little surprised by how badly I want him to continue using my body. I eagerly follow Rob to the table and wait for him to sit down. "Nope." James says just before I sit on Rob's lap. "You gotta share." He says to Rob. "You all agreed to the rules remember. Winner of each hand gets Anna until the hand is over. Todd won the last game he gets her first." Rob scowls, but it barely reaches his face as it disappears as quickly as it came. I slowly make my way around the table. Past Tyler and Chad to Todd, who's grinning like a kid in a candy store. I stand to one side of him and wait. While Chad deals the cards, Todd pulls the neckline of my shirt up, returning it to its original place and covering my ample bosom. "What did you do that for?" Tyler says tossing a pretzel across the table. "I was enjoying those." "You can still see them, it's sheer. When it's your turn you can do what you want with her." Tyler looks at me and grins, "I will." My insides quiver from his promise. Todd pulls me closer to him and wraps his arm around my waist while moving my long, skinny arm down to the bulge in his pants. I give him a little squeeze before bending over, careful to keep my ass in the air and unzipping his pants. I pull his quickly hardening cock through the access panel in his boxers and resume standing all the while keeping my hand moving up and down his cock. Todd lifts the upper corner of his cards, takes a quick look then turns and very slowly, almost too slowly, licks a wet circle around a nipple, through my sheer shirt. Then he moves to the next one. He does this a few times, switching between each nipple, before finally sucking more than half of my breast into his mouth. The pressure of his lips, his mouth sucking so intensely sends red hot lust shooting directly between my legs. I let out a quiet moan. My eyes close and I arch into him, giving him a tighter squeeze. When his teeth graze over my hard, pulsing nipples, it feels as if something inside of me cracks. "Times up, its Tyler's turn." James says suddenly, yanking me from the fire rushing up from my toes. "Fuck I was just getting started." "Maybe you shouldn't have taken your time." Rob suggests. "Or you could try winning another hand." James adds. "It's hard to win when you're distracted." Todd snaps tossing his cards to Chad. I bend over, keeping my legs straight so my ass remains high in the air and plant a kiss on Todd's lips, making sure to tease his lips with the tip of my tongue. "Thank you, your mouth is wonderful." I whisper before bending a little further and planting a kiss on the top of his now incredibly hard cock. I walk around the table to Tyler who immediately yanks my sheer shirt down so that my tits pop out again. "Much better." Tyler and Rob say in unison grinning at each other. "Sit." Tyler tells me when I reach him. "Face me." He says. Tyler, like his twin brother Rob, has wide shoulders and a thick upper body. I straddle him spreading my thighs and keeping my arms at my sides. I watch Tyler as he waits for his cards; his eyes follow Chad as he shuffles and deals. "I see it now." I whisper softly. "See what?" He asks, his eyes moving to mine. "The difference between you and Rob. I've always wondered if there was a way to tell the two of you apart, other than the hair," I stop and curl my fingers in his thick curly hair. "It's your eyes." I smile and lean forward. "Your eyes have tiny flecks of gold in them." "That's not the only difference." He grins pressing my body into his, crushing my tits against his chest. His head drops slightly, his lips somehow finding that spot on my neck, the one just below my ear that makes me lose control. The spot that causes me to shiver with need. His tongue traces small circles around the spot, slowly getting smaller and smaller until he sinks his teeth in. "Uaahah." My body automatically reacts, spasms shaking me. 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."