Winning The Bet

MMMmmm, if I had a better seat in the house I'd be able to lick the boots of the lead singer. And oh what pleasure that would be. He was tall and buff, just enough to make the mouth water. His eyes, a steely grey that shined down as he looked at me. His bright blue shirt was open just enough to show that his chest sported a healthy amount of hair, matching the thick dark blonde on his head. It screamed for my hands to run through it.

He moved away and worked the other side of the stage. I missed his energy almost immediately.

The rest of the girls at the table with me were from my office. I was here just for the feel of doing something different. To end the day to day repetition that seemed to take over my life.

Then the singer came back and locked his gaze back on mine.

Julie elbowed me and whispered, "He came back for you," and giggled.

"That's nuts," I said back. But when I looked up again and saw he was still looking at me I could dismiss it as easily.

Kelly piped up and held out her glass. "To our bid win. That'll show those boys in Level 3 we don't take prisoners!"

We all laughed and raised our glasses in the toast. We had worked long hours and dug deeper to get our bid in early on our latest ad war with the men on level 3 in our advertisement company, and the night out was our reward to ourselves.

"So now back to the hot singer who digs Holly," Kelly said.

"Oh quit it," I giggled feeling the beginnings of the wine hitting me.

"You know he only comes to this end of the table to look at you," Helen said.

"Do you think so" I asked. Then I looked up to see he was there again. I felt his eyes move over me and wished it was his hands roaming over me. Maybe it was the wine and the win, but I felt warm where ever his eyes lingered.

"You want to share?" Julie asked.

"No," I said quickly.

"Ah come on. I bet he could take us all on," Julie pushed.

"I think if the time comes he'd have his hands full just with me," I said snidely. The effects of the wine were clearly leading my mouth.

The girls erupted with hoots and laughter.

Julie nudged me and said, "Stick around and see. At worst it costs you a cab ride home."

Just drunk enough, her idea sounded completely reasonable.

"I bet she chicken's out before the last song is over," Kelly put in.

"I'll bet 100 bucks she leaves in the next hour," Helen added gleefully.

"Hey!!" I said insulted.

"I bet 200 she goes home with him," Julie said in defense of her friend.

"Deal," Kelly said and stuck her hand out.

Julie took it and Helen's as well.

That settled they sat back to wait and see who would win this new contest. Determined to not lose Julie helped Holly's confidence along, and added more liquid courage. At the end of the first hour Helen handed over 100 bucks to Julie. Buy the end of the last song Kelly tossed 100 bucks over to Julie as well.

Through it all I watched the beautiful man on the stage. I was actually praying that he would come down to me. A fantasy slithered into my mind, one where the bar was emptied out, he comes down to look at me close up. He reaches over and touches my neck, gently pulling me closer to him so that I could feel his breath brushing my lips.

He picks me up and sits me on the table, spreading my legs and stepping between them. He leaned in and kissed my neck. I moaned at the sensation of his warm lips on my skin.

I felt a sharp jab to my ribs and came back to reality. I looked at Julie and saw her eyes were laughing.

"What?"

"You went out to space for a while there."

"Sorry," I said and felt the blush move to my cheeks.

"Don't be," Julie said and touched my shoulder, "Every girl has a right to a fantasy."

"Thanks Julie," I said and looked up. The band was tearing down their equipment. I felt a wave of fear tickle my stomach.

"You know you don't have to do this sweetie. It's just a stupid bet."

"It's okay," I assured her, "I want to at least say that I tried something different, something daring for once in my life."

"You don't have anything to prove. You're a good ad specialist. You have a great sense of humor."

Her belief in me only made me want to go through with it more.

"I'll be fine Julie," I told her.

The girls got up and wished me luck. Julie looked at me one more time. I waved her off.

On a spurt of inspiration I reached under the table and grabbed the edge of my skirt then pulled hard at the seam in the side slit, opening it far up my thigh. After cleaning up the loose ends and strands of thread I stood. The lead singer watched me as I moved from the table to a bar stood.

I felt his eyes drop to my legs as I turned and slowly crossed them one over the other. Knowing he was watching my every move I decided to give him a small show. Slowly I turned so he could see more of my body. I trailed my fingers over my knee then up my leg. I watched his eye heat as my hands moved to my shirt and unbutton the top four buttons. I reached back and fished an ice cube out of my drink and sucked on it.

I could see him groan as I sucked on the ice. Lust jumped into his eyes like fire. I smiled at him then moved the ice slowly down my chin, then over my neck. The coolness of the ice was heaven on my skin. I moaned at the feel of the ice and moved it more for my own pleasure then to entice him, though it was working. My eyes closed as I was swamped with lust.

The next thing I felt was a hand clamping around my wrist. When I opened my eyes I saw the singer standing in front of me. I hadn't heard him jump down from the stage and come over to me. The heat in his eye said all that I needed to know. He was breathing hard from his rush to get to me. My pulse raced under his grip.

"You like teasing men like that?" the singer asked.

"How do you know I wasn't just hot?" I asked back.

His eyes roamed down my body and back up again, "You are that. Want to see if I can get you to boil?"

His forward statement made me blink. Even in my wildest thought I never would have expected him to say something like that right out of the shoot. To prove I wasn't shaken by it I leaned in closer.

"Depends on if you have the skills," I said on a whisper.

I saw his Adams apple move as he swallowed hard.

"You're not afraid to speak your mind are you?"

"Not even a little," I assured him.

"Want another drink?" he asked.

"I could go for another one," I answered, but when he raised his hand for the bartender I pulled it back down, "At your place."

The surprise in his said that he couldn't believe his luck. To keep him off balance I leaned in and place my lips on his for a slow, enticing kiss. His arms came around me and pulled me into him as he deepened the kiss. I moaned at how good he felt.

He pulled back to look at me, "The name's Jack."

"Holly," I said back and pulled him back for another soul wrenching kiss.

The guys on stage hooted and clapped for Jack.

"Let's go somewhere private," Jack said.

"Ok."

I picked up my purse and turned to see his arm out for me. All I could think was, how sweet, even if we both knew I was going home with him for more than just a drink.

We stepped out of the bar and I saw Julie standing by her car with the girls staring out the windows, mouths agape. Julie smiled and got in the car and they drove off.

Jack stopped by his car and opened the door for me. After sliding in, he shut the door and rounded the hood. Once he was inside and buckled, he started the car and we left the bar behind. My heart had yet to slow down from the excitement of what I was doing.

Jack glanced at me and smiled. That alone had my bones melting and a slow hum ringing in my ears.

"How far is your place?" I asked sweetly.

"Just a few minutes," he said.

"Oh, too bad," I said with a slight pout.

"Why is that?"

I slid over closer to him and touched his thigh. "I could have seen how well you concentrate while driving."

Jack sucked in a breath, "I think that kind of theory is bad for my driving."

I trailed my fingers up his leg and inched closer to his growing bulge. "As you wish, you are the driver."

His chuckle sounded strained. "Believe me. I would crash us in seconds."

"Ok," I agreed.

Finally he pulled up to his building and stopped the car. I opened my door and stepped out. The building looked classic, all in brick and mortar. A steal roof topped it with more than one satellite dish.

"I'm up there on four," Jack said.

"Ok," I said and followed him in. When we reached the door to the building I stopped him and kissed him fast and hard.

His hands gripped my hips and I felt his bulge growing more as it pressed into my belly.

When I pulled away he asked, "What was that for?"

"A thanks for the drink, just in case I forget later."

His laughter vibrated off the door behind us. "My pleasure," he said then opened the door.

Once inside the elevator he pulled me close again and buried his face in my hair. "Damn you smell great."

"Thanks," I said and trailed my hands up and down his back. The muscles jumped where ever I touched.

"Can this elevator moved any slower?" he grumbled in my ear as he pressed me closer to him. Instinctively I ground my pelvis into his and was rewarded with his low growl of arousal. "Do that again and I'll stop this car between floors."

I giggled in his neck and licked along his ear. The elevator finally stopped and Jack rushed us to his door, with me continually stroking and licking every piece of flesh I could reach. He opened the door and quickly closed it to press me against it. He moved n and locked his eyes on mine.

He leaned in and pressed his lips to my neck, slowly nibbling up and down, making me shiver with wanting him. His hands moved over my body as if he couldn't touch enough of me.

Wanting to tease him more I pushed on his shoulders to move him back.

He looked at me confused. I just smiled and moved around him and walked into the apartment further, slowly opening my blouse and then let it slip down my arms to fall to the floor carelessly. He followed like a love sick puppy. I walked into his kitchen and turned as I pulled down the zipper on my skirt and let that fall to the floor as well. The fire in his eyes made my heart race with excitement.

"So where's my drink?" I asked oh so calmly.

"Your..." he started then lost track as I reached back and unclipped my bra and let that fall to the kitchen floor. His eye zeroed in on my breasts in full view for him to enjoy.

"My drink," I provided.

"Uh, sure," he said. He moved to his refrigerator, never taking his eyes off me, he opened it and blindly reached in and pulled out a bottle of wine.

Convenient, I thought.

He then probably thought that it would be best if actually watched what he was doing or risk dropping a glass. He poured two glasses half full of the wine.

While he was turned I took the opportunity to room my panties and climb up on his table. I leaned back on my hands so that my breasts were pushed out a little higher. When he turned back to me he nearly bobbled the glasses. I smiled sweetly and waited.

He walked over and handed me one of the glasses. Then he did something I never expected. Slowly he tipped his glass and dribbled wine down my breasts and leaned over to lick it off.

I quickly set down my glass and grabbed his head. I moaned as he licked all the wine from my skin then gently nipped my nipple between his teeth. He moved back and dribbled more wine, but this time on my thighs. He set down his glass next to mine then he kneeled in front of me, and placing his hands on my thighs, he spread my legs wide. While holding my gaze captive with his, he leaned in and began to lick up my legs, collecting the wine as he went.

I couldn't stop from wiggling. He was making my insides turn to mush as he continued to nibbled and suck and lick my legs. I could feel myself getting wetter and wetter with the erotic sensations flying into one another. I knew this was payback for the strip tease walking in here. He barely touched me the way I wanted and I was soon leaning back until I was lying on the table.

He moved over me and kissed me fiercely. I moaned and fisted my hands in his hair. The contrast of his clothes rubbing over my bare skin made me hotter. Panting I began to pull on his shirt, freeing it from his waist band. My hands snaked under it to touch his flesh. Oh his skin was so smooth and felt incredible.

I pulled again until I got it over his head and off, throwing it to the floor to join my bra and panties. I wanted him right here on his table, so that whenever he looked at he would remember what we did there. I reached down and opened his fly and pulled down the zipper. He stood to help and shoved them down and off his legs. I was overjoyed to see he hadn't bothered with underwear.

He stood there in all his glory, his impressive erection standing proudly out for me.

I couldn't resist, I reached out and grasped him in my hand and slowly stroke him. He was smooth and hard as a rock. The head was nearing purple from his excitement. Unable to stand it he grasped my wrist and placed my hand on his chest.

"Bed," he said hoarsely.

"No," I said and had his eyes shooting to mine. "Here," I said and reached up to pulled him down to me for a hot searing kiss. Now I had some wine at the bar and that left me feeling giddy. But that was nothing compared to what his kisses did to me.

"Wait," he said as he pulled back.

"Why?" I asked.

He just picked up the glasses of wine and moved them to the counter and then came back to me. I smiled up at him as he ran his hands through my hair. I always loved the feel of someone's hands in my hair. The way he fingers curled to grip it and pull my head back. It was a sense of being controlled but with the freedom to back away if I wanted.

He leaned in as I saw the heat flare even more in his eyes. I saw then that I was fulfilling a fantasy for him.

"I want you so bad right now," he said.

"I know," I said and ran my hands over his chest and down his belly. I again grasped his hot cock in my hand and slowly stroked him for his balls to the tip. A little precum seeped out and I swirled my fingers around in it. Then while he watched I brought my fingers to my mouth and sucked his taste off them.

Jack groaned, and then he lost it. Grabbing me around the waist he pulled until my ass was just at the edge of the table. He kneeled again but didn't pretend to tease me and went straight for my wanting cunt. I moaned as he devoured me, taking no mercy as my moans got louder and louder. His tongue was heaven and I couldn't keep from wiggling and moving as he licked me from my clit to my love hole. He was skilled at this and he knew it.

Then it was everything all at once. He touched a finger to my vagina and inserted it deep and fast. I screamed from the pleasure as he reached for my g spot and wiggled it around inside me. He added another finger and my screams increased with the added sensation of him spreading my wider. Then he latched his lips on my clit and that was all it took. My orgasm hit me hard and fast, flinging me over the cliff and crashing me back down.

He stood as soon as my quacking a slowed, my cunt still twitching in the aftermath, and he slid his cock into me. This sparked another orgasm that had me twisting and turning and forcing him into me deeper. He slowly moved his cock out and then slammed back into me, effectively keeping my orgasm going. Whenever I even appeared to be coming down he would do it again. By the fifth chain orgasm he began to thrust into me harder and harder, then faster as he was near exploding.

Then I looked up into his eyes as I felt his balls tighten against my cunt lips and he slammed into me once more. He erupted with a loud howl, and feeling his cum filling my cunt triggered my sixth orgasm for the night. He collapsed on top of me and I held on to him. My body was twitching like it was hit with a live wire. And his wasn't too far from feeling like was as well. I could still feel his cock twitching inside me. I squeezed down hard with my cunt and felt him shudder from the pleasure.

He leaned up enough to look at me. His face said it all. The pleasure and rapture of having been here with me like this was written all over him. He gently pulled out of me and then picked me up to cradle me to his chest. I wrapped my arms loosely around his neck as he carried me to his bed. He pulled down the sheets and laid me down and climbed in with me, pulling the sheets up over us.

"MMMmmm that was wonderful baby," I said and rolled over to see his face.

"More then," Jack agreed. "Did you win the bet?"

I started laughing at the thought. "Without a doubt, when we left I saw Julie standing outside next to the car we all came in."

"Do you think any of the girls suspected that we've been dating for three weeks?" Jack asked.

"Not a chance."

"How many drinks did you have anyway? I only counted two."

I moved closer and snuggled against Jack, feeling warm and relaxed as his arm curled around my waist. I yawned, "Maybe three. I wanted to be sure I knew what the bet was about."

"My girls too smart," Jack chuckled and kissed my forehead.

I smiled up at him and leaned in for a lingering kiss.

"Jack," I said a little sleepily.

"Hmm," he said just as sleepy.

"Is it ok to say I love you?"

I felt Jack's arm tighten around me and I saw his eyes snap open. When he looked down at me I was unsure of what he was thinking.

Jack smiled and rolled over me, pinning me to the bed. He brought his hand up and lightly trailed his fingers down my cheek.

"I've wondered when you would tell me," he said. Then he leaned in and kissed me with a fierceness he hadn't before. He barely lifted his lips from mine and said, "It's ok to say it, as long as I get to say it back."

I laughed and pulled him down to me. We loved each other again, and again through the night.

The next morning when I walked into the office I had six eyes trained on my every move.

Julie was the first to ask, "So?"

Then Kelly piped in, "She's not walking straight enough for me."

"Ok Kelly," Helen said, "We can all see that. So I take it you and the singing stud had more fun after we left."

I just looked at them and smiled a secret smile and walked to my desk without saying a word.

"Oh come on Holly," Kelly protested and followed me. "Give. It's not like we went home with a stud last night."

I laughed and booted up my computer. I was determined to make them sweat.

Julie just watched and I could see she knew I had gone through with going home with Jack and more. It was the more that I saw she was looking for.

When Kelly and Helen saw I wasn't going to give them details here they gave up and headed to their own desks. Julie continued to look at me.

"So?" Julie asked again.

"Make sure to collect on your debts," was all I said and went to work.

Julie burst out laughing and went to her desk as well.

I smiled knowing that my secret would be a hard nut for them to crack. Maybe I'll take it to the next level then next time we all go out. A new game was forming in my head. One that I knew Jack would play along with.