tagGroup SexAnna's Lesson in Betting

Anna's Lesson in Betting


*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."


"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.

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