David Pays His Bet

I should never gamble.

With luck like mine, I should know better but there I was, full of certainty that THIS time I was going to get her under my control at last. We'd been playing at submissive and dominator for a while. She knew that I enjoyed both roles but lately I'd been on a submissive streak.

The playtime was always good no matter what we did. What made it great was how neither of us had to hold back or worry that by letting our darker desires show we'd lose respect with the other. It seemed that the more we let each other see our passions and desires, the better the sexual experience was. This time I wasn't so sure. This time was not an on line or telephone playtime, this was for real.

We'd been teasing each other sexually for hours on line and then we moved to the phone. Her voice always got me tuned to a fever pitch. There was a special quality about her tone and timbre that made me want her all the more. This time was no different. This time we were working toward a bet that was typical for us except for the stakes.

The one who gave in and started stroking themselves first lost. It was as simple as that. Tease the hell out of each other using words, voice, sexual stories, even live webcams but make the other touch themselves before they make you start playing with yourself.

It was on the honor system, yah... but that's what was so great about us. We were completely open to each other. She knew every one of my fantasies. I knew hers. She and I had confessed our fears about ourselves about what we didn't find attractive in ourselves. She knew what would turn me on and what I was too scared to do but desperately wanted to do. I knew just those same things about her.

I agreed to the bet just so I could fulfill one of her fantasies. Yeah, I assumed I'd win. She wanted two men to abduct her, take her body for their own pleasure, but had never been bold enough to find two guys where she lived to help her live that out.

Mine was to go beyond submissive sexual partner and be a slave for a day. I wanted a woman to own me and treat me like her property, but I was never going to instigate that fantasy on my own. That is, until the bet was lost.

She got me by reading aloud from literotica where she knew I visited often. Her softly modulated phrases were like tendrils of fog at first. Insubstantial yet able to obscure everything else as they drew you into their mist. I was lost in the mental images from the story she dropped like a movie scene into my lust filled mind - where we were the actors.

She smoothly read how in this movie she was nude, kneeling between my knees and slowly licking the length of my cock. I could picture her silky hair shining and cascading as her face turned and bobbed. I watched as she looked up at me and slowly pressed her lips tighter, tighter, and tighter still. I could feel the pressure - and that's when I realized that I had let myself go to far. She'd won.

Her giggle when I confessed to losing was also typical. It was just like her to win and act as if there had never been a doubt who had the greater self control. She told me that she'd let me know more about how I had to pay off my bet later on, but being the lover she is, she talked me through the rest of that story and my orgasm.

So here I was. Nearly 7 pm. Going to the address she gave me in the e-mail. Wearing the sweatpants and sweat shirt she told me to wear. Nothing else. I carried a small duffle with "supplies" as she called them: a gold lamay g-string, a pack of permanent markers in assorted colors, the anal plug she'd watched me use on webcams, several lotions, oils, a straight 7" vibrator, and a length of cotton cord.

If that list of supplies didn't have me worried, there was one last item that did. She had insisted that I bring along a stack of my business cards from the office. I fretted the entire time over that one item. I trusted her, but why would something to identify me like that be on the list? Why a stack? Too late to wonder now, there was the house.

It was a typical suburban neighborhood in middle class America. Lighted front porch, two story, and I guessed maybe 4 bedroom from the size. Nicely kept lawn and it looked like a wooden stockade style fence around the backyard, like the kind people have if they have a backyard pool and want privacy.

I had to park the rental car down the street a ways because the driveway and front of the property were all parked up with mini-vans and volvo's. I was to knock twice then wait. Once I knocked, I was signaling that until dawn I was her property.

I drew a deep breath and knock sharply once... then twice. I could hear sounds of people talking inside. In fact, there must be a lot of people. All those cars must be for the people inside. What the hell was I getting into? Just then, the door opened and she greeted me with the smile that always made me melt.

"David! Right on time. Please come in and begin your new career as my personal slave."

The smile on her face turned to something more sinister as she said this but like I said, I trusted her so I stepped across the threshold. She looked fabulous. Better than I hoped in fact. She wore a loose tunic belted with a sash and pajama like slacks. The shimmer to the material made me mindful of silk.

"You like the look?" She spun in place. I did like the look, in fact I was begining to react to her presence. Her eyes drifted down and saw my cock pressing lightly on the sweatpants, making them tent out in front of me.

"Ohhh I love it that you dressed how I said. Come here and let me see for my self." I stepped closer and without even a pause she tugged my sweats down exposing my growing cock.

"Mmmmm that IS a good boy, David. Follow me." She turned toward an archway behind her and I reached down to pull the sweats back up. She caught the move from the corner of her eye and said "Oh no darling, I like your sweet cock too much to cover it up already. I want to watch it bouncing as you walk over here with me."

I flushed beet red. It was one thing to be naked on a web cam, but this was real. Worse, one of the other people in the room behind her might walk out at any second. "This is how I suppose I'm to be treated for the next several hours?" I queried.

"Sweetie, if you don get those cute buns over here and right now, this is going to be a LONG night for you. Now move your ass, SLAVEBOY" she said with deliberate force.

I only hesitated another second then tried my best to walk to her without tripping over the sweats around my knees and without causing too much bobbing at my now completely engorged cock. She had me stop just short of the entryway to the room from where the voices emanate.

She rolled the fingers of her left hand around my cock... "This, and all of you is now MINE. You do as I say, when I say without hesitation or I shall be forced to demonstrate my ownership in ways you won't like when we're alone, let alone in front of a crowd darling... " at "darling" her hand started stroking me fast and hard.

"Feel this pleasure slave? It's only because I choose to let you have it. I can also give the opposite if needed... and we know you are a wimp to pain SLAVE BOY." At this she twisted her wrist just enough to force me to turn sideways in her grip. With her right hand she placed a hard, loud SLAP! on my exposed ass-cheek. I knew better than to wince so I said simply

"Thank you Mistress, may I have another?"

Her answer was to smile slowly and with a devilishness that worried me. Then she instructed me to pull up the sweats and come into the room with her. I quickly pulled the sweats over my stiff and now throbbing cock, but it jutted out against the baggy cotton fleece sweats so much, that there was little point to wearing them. Swallowing the lump in my throat, I walked into what should have been called a Harem.

"Everyone... may I have your attention for a moment?" her voice rang out cutting through the general buzz of conversation. "This is my friend David. Please, don't let his being here throw off your plans for fun tonight, he's is the man I told you all about. He's here to help me with whatever you need to be comfortable."

When she said "whatever", she looked down at the huge tent my cock was making in the sweats. The room full of ladies tittered and a few ill-disguised gasps were heard. A stunned silence then the buzz of conversation resumed while most of the ladies there took me in like I were meat in a butcher case.

"David" she motioned me close to her. "This is my annual ladies night out party. There are only first names except for you. To make the ladies feel more at ease and comfortable, you will now go and offer your business card to everyone here. Oh, and David... I told the ladies they could look, touch and even taste. But if you dare cum without asking me first, you will be severely and publicly punished. Do you understand?"

I understood. She was placing me into the fantasy I only dreamed of. I knew from long experience with her that she meant every word. "Yes, Mistress, I understand."

"No, SLAVEBOY, I don't think you do." Her lips curled into that smile again. "You are here for THEIR pleasure, not yours. You are not permitted to have an orgasm unless I give it to you. You will see to it that ANY of my guests who wish to be pleasured by you in ANY way receive your total attention. NOW do you understand?"

Her eyes had a fire in them I had not seen on line. I wondered if I were up to the fantasy I asked for so many months ago. This was going to be much worse than hearing her moans over the phone and trying to not touch myself, this was real. I looked imploringly into her eyes and opened my mouth to ask her to let me out of the bet. At that moment she looked right past me exclaiming with a wide smile...

"Dora!!! You look divine in that teddy!!"

I turned slowly and indeed there was a stunningly beautiful redhead in a white lacey teddy that showed off her long legs to great advantage. Her breasts held up the teddy so that her nipples poked out from the cloth. The result was to raise the front of the teddy's hemline in the front just enough to make the darker patch of hair under her panties visible until she moved up close. At that point I didn't care about the glimpse thru her panties. She was ravishing no matter where I looked.

"I think that David forgot something" Dora smiled to my new Mistress.

"David, Dora is waiting... "

I stood stupified. I could not imagine what I was supposed to have remembered. Then, I remembered and gave Dora a business card.

"Ohhh slow response time here", Dora licked her lips. "I think we need to jog this boy's memory"

"Be my guest, honey.” My Mistress said I'm going to go see to the kitchen. I'm sure you can help him remember to follow instructions better." and with that, I was left standing in front of Dora, tented sweats and all while the only person I knew in the house walked into the kitchen.

"On all fours, please... quickly now." Dora pressed my shoulder downward. I looked up from my hands and knees and told Dora how very sorry I was for the slip, but she was bending over me from where she stood at my shoulders. Once more I felt my sweat pants being pushed down.

"Ohh she was right, his ass is perfect for spanking!" Dora exclaimed to the room. Several other ladies, also dressed for sleeping, gathered about. "Now David, we are all going to help you remember to give out your cards. Afer each of us gives you our reminder, you give us a card.... ok dear?" Dora's condesending tone grated on my nerves, but I knew better than show it now.

"Yes M'Lady Dora, thank you for your help."

And with that a stinging slap landed on my buttocks. A hand reached down in front of my face and I placed my business card in it. Another slap, this one much harder. A hand appeared. I pushed a card into it. A voice chided.. "No thank you for me? This one needs better manners." SLAP!! SLAP!! I winced this time. There were at least 15 women here and I knew my ass was going to pay for my foolish bet. SLAP!! "Thank you Maam, please have my card." SLAP! A hand, a card, a gracious thank you thru gritted teeth from me. Over and over...

I lost count after they went around the third time. I heard giggles and comments like "Ohhh thats got to sting." or "Don't you love a man who knows his place?" The worst were the flashes from cameras. My ass paid now, my name and reputation were gone at this point for the rest of my life. Any one of these women could share the pictures they took, along with my card and I would be ruined in the business world.

Tears flowed as I thanked the woman who gently said I could get up, she was the last. The ladies were standing in a circle as I stood. Dana was there, behind them slowly shaking her head side to side as if to say "You wanted THIS?"

Then Dora, whom it was obvious now was the leader of the group, suggested I might as well take the sweats off completely. "After all" she said mockingly, "its not as if you have any pride left." I hated to agree, but she was right. I was just a piece of meat for them to play with and discard. They watched me disrobe with cat-calls and whistles. Several asked Dana if she would share me later on.

A blonde woman with stringy hair told me she needed her feet massaged. I followed her to the living room couch and knelt rubbing her feet while the party resumed all around us. She was enjoying rubbing her foot on my cock, keeping it hard while I massaged the other.

Another redhead, who had evidently been drinking a bit heavier than the rest, told me she wanted her back rubbed, then pushed off her robe to reveal her nude body. She lay on the floor on her back and told me to rub the front first. I turned beet red all over again when my cock went to full attention and several women laughed aloud.

Massaging from the feet and ankles, I moved along her legs to her hips. She began pushing my hands toward her pussy saying in a slur that I missed a spot. Never was I so embarrassed. I slowly inserted a finger and began to glide inside her hoping to locate her G-spot quickly and get this over with.

"I bet he can't make her cum right there on the rug." I heard Dora's voice behind me. "She's too drunk and he obviously is a novice at this.. Look at him!"

"I'll take that bet"

I looked up to see Dana smiling down at me reassuringly.

"He is no rookie, Dora. I'll bet you that she'll be screaming for his cock in no time at all."

Dora looked cooly down at me and the redhead. "You're on honey, and if I win, I get to shave him... from the neck down."

I gulped... then Dana spoke up "Deal! in fact, if he can't make her cum you can shave him while he sits on this..." She held up the anal toy that I brought from home. I blushed beet red once more.

The ladies circled round again and I started working in earnest to not only keep the drunken redhead awake, but to arouse her too. With a dozen or so women standing around shouting or offering advice it was looking impossible. Then I felt the telltale softness of her g-spot.

I leaned over her and said in her ear "I'm done teasing you now. If you're ready to feel heaven, move with me now..." and with that she started to use her hips to ride my finger and let it glide across her g-spot. I provided the pressure to her clit with each upward thrust and let my fingers dance along her sensitive inside as she fell back to the floor. In moments, we both forgot the jeering and spectators... her hands came down to grab my wrist, then my arm, then she tried to pull me over her.

Instead of allowing that, I moved to her side. Now she took my cock in her hand and stroked me with each thrust her hips made against my hand. I knew if I let her keep that up, I would cum. If I did, then I would be in huge trouble. I move my hand faster... faster... faster. Her stroking was bringing me to the edge much more quickly than she was, the booze slowed her down tremendously.

I felt pre-cum lubricating her strokes on my shaft when at last her back arched high and moans of pleasure erupted from her lips.

"DAMN!!" Dora said with a gesture of resignation. "My sister NEVER gets off after drinking that much. He must be as good as you say."

"Oh, he's alright as men go" Dana said. "but look girls... he nearly got off too!" and she pointed at the wet dribble and glaze on my cock.

Then one of them told me to bring my cock closer for inspection. I was so close to cumming, that I feared that any touch would put me over. I moved from my knees on the floor slowly. Too slowly for I felt a smart SMACK on my poor red ass and the command.. MOVE IT! from one of the women.

I stepped in front of the youngest looking one, who, from her perch on the arm of the couch had asked for the inspection. She took my cock in her hand put her index finger and thumb in the shape of a ring at the base and squeezed upward, milking my pre-cum. then she leaned in and sucked the juices from my head.

My knees nearly buckled. I thought about ice, wax, the sting in my ass, anything to keep from cumming. She let go and proclaimed... "Yep, its pre-cum alright!" Then burst into giggles with several others who all enjoyed the overstatement of the obvious.

From that point on they seemed to take turns having me touch them, or lick them or stroke myself while they watched and made me beg to be allowed to stop before I would cum. I was totally humiliated. As the night grew into the morning, I simply gave in and let them enjoy making me a toy for their pleasure, or for their disuse.

At one point, they decided to put "hickies" on me and autograph my body where they had placed their bites. Of course, they used the permanent markers that Dana told me to bring. The only restriction she enforced at that point was that it was her cock and no one else could sign it.

As the morning drew nearer to dawn, I found my self tied over the coffee table while they used my ass with the toy, with dildoes, with the vibrator, with ice, and even cucumbers from the refridgerator. They kept asking me if I was going to cum for them. I replied each time that I was not. They asked if I need to cum... and if I lied and said no, they watched while I stroked myself to the point of pre-cum and begged for permission to stop stroking.

Finally, Dana told the ladies she needed my assistance in the kitchen. Once there and head down, she handed me the gold lamay g-string.

"You're going to be a bus-boy now. Then you're going to wash all the dishes and clean up for me, Kiddo." I slipped the tiny but gawdy triangle on and felt her fingers pulling the elastic in my butt crack.

"I could let go and really give you a sting" she said with a sly grin, "but I think your poor ass has been given enough attention for one night... don't you?" "Yes Mistress ... TY Mistress." I replied in a demoralized tone. She looked at me for a long moment, then rejoined her guests.

I cleaned and washed, cleared and shined. The ladies left me alone now for the most part except for the occasional feel under the tiny gold patch until Dora stopped me just inside the kithcen door while I carried a full tray of dirty glasses. "Do you know how much I enjoy seeing you worry about getting punished?" She said with a sly grin. Without waiting for an answer, she tugged the G-string hard and snapping the flimsy straps, tossed it on the floor.

Her hand closed on my cock and her voice came in a terse whisper. "Eyes straight ahead boy... don't make a sound." She stroked me and I felt something lubricating me. I did not dare look down. I was tired, but she knew exactly how to use her hands. In minutes I was straining not to flex my cock and let the cum that was denied me all night burst out.

"You want to cum, boy... don't you?"

"Yes Maam.." I gasped out from clenched teeth. She stroked faster.