Side Bet Bluff Ch. 01

Jaycee calmly stood up and slowly proceeded to strip. After each article of clothing she would again, slowly, fold it and place it on her chair.

"Don't forget the shoes," I reminded. I know some guys like to have their women keep their high heels on when they're otherwise naked. At least, I assume that's the case considering how much porn is out there with the women in nothing but their heels. I wasn't one of them, though.

Jaycee had skinny legs that widened slightly to wonderfully rounded hips. She had cotton pink panties on with some kind of blue and purple starburst design on them. As she pushed them down her legs and stepped out of them one leg at a time I got brief tantalizing glimpses of her neatly trimmed pussy. But when she stood up completely she just put her hands on her hips and smiled at me, showing me everything. No she wasn't a photo-shopped looking centerfold. She had moles and other imperfections. I didn't care, though. A pretty, naked girl in the flesh is a thousand times more attractive than some unrealistic and unobtainable image of the female form.

I made a circling motion with a finger. Jaycee smiled again and slowly turned in a complete 360. She looked skinnier than when I had seen her in a swimsuit over the summer. Actually, she looked a lot skinnier, but not in an unhealthy way. How that happened without losing any of her boobs I have no idea. She had also complained about having a cottage cheese ass at the time, but there was absolutely no evidence of that now.

Jaycee picked up her pile of clothes (giving me a wonderful moment to admire her ass) and then presented them to me.

"I believe these are yours, sir," she said.

I liked the 'sir'.

I set the clothes down on the table to my left, in between me and Aaron. Jaycee went to sit back in her chair, but I blocked her and then pushed slightly back from the table and opened up my arms in invitation. Jaycee looked me in the eye and seemed to say 'why not', then settled into my lap confident that I was too much a gentleman to try anything more, and confident enough in her victory to even taunt me a little more with her body.

"And now for the grand unveiling," Jaycee said.

"Too late," said Aaron, to giggles from Susan.

Jaycee looked questioningly towards me. "I called your bet," I reminded. Jaycee turned back to the table and reached for her cards. "Can I guess?" I asked. Jaycee glanced back at me and nodded. "Ace and King of diamonds," I announced, praying that was it instead of the King-Ten combo.

She smiled once again, said "even better" and flipped over two Queens. She hadn't been on a straight draw, nor a flush draw. But she had flopped the highest three of a kind, and then added later to make a full house, her second of the night against me.

"How ..." started Hannah.

I gave Jaycee a small smile. Jaycee couldn't stop smiling, so confident was she in her win. Hell, if I was in her shoes I would have been too. She probably had me figured for either a straight or a flush, and she beat both of those. "He only figured out he had a losing hand after he'd committed almost all of his money, and then he decided he was willing to lose the small amount he had left in order to get me naked," she declared.

I had to compliment her play. "Your fake tell was exceptional," I said, giving her leg a little squeeze.

Jaycee grabbed a strand of her hair and stuck it into her mouth. "Wasn't it?" she agreed.

Aaron whistled in appreciation and shook his head. I don't think Tim had enough blood in his brain to follow the conversation. It had all collected in his dick. Hannah was looking at Jaycee with some mix of admiration and annoyance.

Susan couldn't help herself. "So who won?"

As I reached for my cards Jaycee asked, "Can I guess what you have?"

"Sure," I agreed.

"Two diamonds, one of them the eight," she proclaimed. "The other's probably the seven because suited connectors was probably a good enough hand for you to pay to see the flop. Then you flopped the flush draw with a pair kicker. Then you made the flush and almost, almost, almost had that straight flush. But you were still worried that your diamonds weren't high enough to beat my diamonds. So eight and seven of diamonds."

I flipped over my top card, the eight of diamonds.

"Wow," said Susan.

"You are very, very good," I told Jaycee. "Much better than I suspected, and I even suspected you were snowballing us. But I still didn't have a clue how good you were."

"No kidding," muttered Aaron. Jaycee smiled beautifully at me, loving the accolades I was placing upon her.

"However," I started. "Sometimes it's better to be lucky." And I flipped over my other eight.

Jaycee just sat there in stunned silence on my lap, staring and staring and staring at that fourth eight.

Aaron quipped, "Well I'll be a monkey's uncle."

"So Jaycee lost?" asked Susan.

"Yes," I replied. I grabbed Jaycee's hair at the back of her head and turned her towards me until she was looking into my eyes. "Jaycee lost."

Jaycee shuddered, and I could really feel it considering she was sitting in my lap. And, very curiously, her nipples hardened. The way she was sitting in my lap, her back was turned to most of the table.

"Remember," I told her, "like we said earlier -- no running away now. You have to stay and serve us refreshments until the game is over."

I swear Jaycee's eyes dilated a bit as she looked at me. And were her nipples hardening even more? Very curious. Jaycee looked down, with me loosening my grip on her hair to let her, and she nodded in acquiescence while shifting a bit on my lap.

"Of course," she said, still not smiling. "Let me just go collect myself first." And with that she stood up and walked out of the room and down the hallway towards the bathroom. Hannah and Susan quickly got up and went after her. I thought I overheard Jaycee saying "sorry" to the other two but maybe not.

I turned back to the other two guys, shaking my head and smiling at them.

"Dude! You are the man!" said Tim.

"Dude, you are the luckiest man ever," said Aaron.

"Don't I know it," I agreed, and started collecting and organizing my now enormous pile of chips.

"It's getting late," said Aaron. "And after that hand, the girls aren't going to want to play much longer."

"No way man!" disagreed Tim. "We've got to drag this out! I want that hot little bitch to sit on my lap and serve me grapes, one at a time!" he laughed.

I smiled at Tim, but said "if you think you can just grab Jaycee and pull her into your lap, you'll end the night right then and there, and you know it. The girls are going to be very upset about this whole situation, and they'll just look for an excuse to come to Jaycee's rescue. But if we're polite, and courteous, and keep our bets small, then we can enjoy the sights for a little while longer."

Tim seemed to think about that for awhile, and finally said. "Jaycee's right. You are really smart." Then he smiled really big and said, "ok, I'm game."

Just then the girls came back, with Jaycee wearing nothing but a big smile. "So, can I get you boys another round of refreshments?" The smile looked a little fake, but I appreciated her putting on the brave face for us.

"Hell, yes!" yelled Tim. "Oh," he immediately glanced at me. "I mean, yes Jaycee, that is very nice of you." He then winked at me. Cripes, I swear I needed to figure out what village he came from and send him back there, they were obviously missing their idiot.

The big surprise for me was after Jaycee had gotten everyone new drinks, and had refreshed the bowls of nuts and chips, she settled back into my lap. I couldn't believe it, but of course tried to play it cool as if I didn't expect her to sit anywhere else.

We proceeded to play a bit more, keeping the bets small. I stayed in every pot, just to give the winner a slightly bigger payday. I figured it would keep the game going a bit longer, and I could certainly afford it now. I did make an effort to prevent Jaycee from seeing my cards. She looked at me curiously the first time I did it but shrugged. Maybe she thought I was afraid of her sending signals to her friends. But she soon clued in to my running up the pots only to lose (usually folding immediately after the river) and smiled at me. I took the chance to leer at her, and she shook her head and smiled again.

Tim finished his drink in record time and called for another refill. Jaycee rolled her eyes at me and I gave her a wink and a squeeze before she got up. This time I didn't ogle her as she trekked back and forth from the kitchen. Oddly, both Susan and Hannah did. After Jaycee settled back in and play resumed, I started seeing some interesting glances from the other girls. Susan would look my way often, but no, she wasn't looking at me. She was looking at Jaycee. Was she turned on by Jaycee? She was also casting frequent, fertive glances at Aaron. And she was obviously very frustrated with her cards, folding one hand after another with disgust.

Hannah was also giving odd glances in our direction. Looking at Jaycee, but also at me ... with ... longing? No, couldn't be. At times she also looked seriously pissed, but at Jaycee instead of me. She would occasionally steal looks at Tim, but would then curl her nose in disgust at his blatant drooling over Jaycee. Tim was just acting like an idiot. We would often have to remind him when his turn was up, so intent was he staring at the naked girl in my lap.

Finally it appeared that Susan got the hand she wanted, and she raised with a strong push of chips into the center of the table. This girl definitely didn't have a poker face. I called as usual, tossing my chips into the center. Everyone had become so used to this by now that Susan didn't even glance my way. Aaron looked at his cards, then at Susan, back at his cards, back at a smiling Susan. He must have liked something he saw, because he called. Tim and Hannah folded. The flop came ten-nine-four rainbow. Susan bet strongly again, and Aaron and I called again. The turn came with an eight of clubs, doubling up the clubs in the community cards. Susan bet half her remaining chips, and once again Aaron and I called. Normally I would fold, but with Susan betting so much it looked like this was going to be the last hand of the night, so I decided to give the winner a little extra present of a big payday. The river was an Ace of clubs.

"How many chips you got left, Aaron?" Susan asked, with a weird tone in her voice. She sort of sounded like a muppet.

"A hundred and thirty," Aaron slowly answered, with a tone that matched Susan's. Whatever it was they were doing, I had a hunch this call and answer was part of their foreplay routine.

"I only have thirty." Susan said, and then pushed it into the pot. "You think we can swing some kind of deal where you put your remaining hundred in there too?"

"I'm not going to let you get naked in front of everyone," warned Aaron.

"Oh, no. I'd never do that!" said Susan, still in that weird voice. "But I was thinking that for an extra hundred, I'd let the winner of this hand finally get what I've been holding onto for so long."

"What?" croaked a stunned Aaron.

"That's right," said Susan. "Is that widdle 'ole small bit of money something you could part with for a chance at my cherry?"

Again, with the weird voice. I'm telling you - it was a little creepy. Wait. Did she say cherry?!? She was a virgin? I knew she was younger than me and Aaron but she was at least twenty-one! The only women that old and that good looking who are still virgins are religious wackos saving it for marriage, and they don't offer it up at a poker game for a hundred bucks! What the hell was going on?!?

Apparently this conversation was enough to drag Tim's attention away from the naked Jaycee. "Wouldn't that make you a ..." Tim began, "Ow!" but never finished thanks to a quick kick to the shins from Hannah. She wears pointy shoes.

Jaycee got up out of my lap and went over to Susan. They whispered together for a bit, then Susan started to show Jaycee her hole cards, but Jaycee pushed Susan's arm back down. Jaycee bent down and whispered something else and Susan winked at her. I wasn't thinking about much other than the fact that Jaycee had cute little dimples at the top of her butt. Hannah decided she didn't want to be left out of the girl pow-wow, so she joined the other two and there was even more whispering. Hannah sat back down and Jaycee stood slightly behind Susan and to the side. I found it interesting that both girls were backing Susan's play here.

Aaron couldn't even talk, or didn't trust himself enough to open his mouth. He started grabbing at his chips when I spoke up. "And what happens if you win, Susan?"

Aaron froze. Obviously this was an unexpected, but very important, piece of information.

"I'll get all the money," Susan said, confused that there could be another option.

"That's it?" I asked.

Susan looked at Aaron. "That's it," she said.

Aaron quickly threw his chips into the pot.

Susan smiled and moved her hand to her cards.

"I'll call that bet, too," I interjected.

There was a collective gasp from Hannah and Jaycee.

"You can't!" said Susan.

"Of course I can," I said as I started counting out enough chips. "I'm still in this hand."

"But that offer was just for Aaron," whined Susan.

"No, you said and I quote 'I'll let the winner of this hand get my cherry.' You specifically said the winner of this hand, instead of naming Aaron. I'm pretty sure I know what your hand is based on the betting. I'm pretty confident of what Aaron has. And I'm certain I have the best hand. I'm still in this hand, and I'm calling your bet, as well as the extra hundred dollar offer."

"No! You can't do that!" squeaked Susan.

"Dude ..." Tim began in a low, warning tone. I was surprised. I expected Aaron to speak up, but Tim? I thought he'd be all over this. I guess he really was a good friend to Aaron. I turned sharply to Tim, pointing most of my face away from the girls, and winked with my left eye so that the girls couldn't see. Meanwhile, I pretended to glare menacingly at Tim. Aaron looked very unsure of everything. Actually, he had looked pretty unsure of everything since me and Jaycee's big hand. It looked like his confidence was blown. I hadn't counted on that. But once you start a play you have to follow through and see where it leads.

Tim backed down, and I started counting my chips over again since I had lost count.

"Hannah, do something!" screeched Susan.

"Err ... um ..." said Hannah. I glanced up at her with an 'are you kidding?' look of contempt on my face. "I'll buy off that bet," she said.

"With what?" I replied. Hannah knew nothing else she said could stop me. If anything, it would only make me more determined. Susan came to that same conclusion.

"Jaycee?" cried Susan. She was really getting hysterical. I loved it. I paused in my chip counting and glanced up at Jaycee. I tried to do my best Mr. Spock impersonation where I raise just one eyebrow, but I really couldn't do that.

"Could I perchance offer you something to buy out your bet?" Jaycee, rather formally, asked.

"Oh, I'm always willing to listen to serious offers," I responded.

Jaycee nodded her head over to a corner of the room away from the table. I nodded my assent and we removed ourselves from the others.

"Ok, why are you screwing this up for her?" asked Jaycee in a low voice.

"You heard my reasons," I answered. "Besides, I'm really starting to look forward to breaking Susan in. She's been such an annoying shit to Aaron that she's been driving me crazy."

Just for the record - I didn't mean that at all. I had no intention of actually going through with the bet. I just wanted to shake Susan up. I had thought it would be Aaron 'saving her from that horrible man.' I had been trying to help Aaron get the upper hand back in Susan's virginity giveaway, especially since he was going to lose to Susan's three aces. I had not even considered Aaron's failure to challenge me. And with Aaron failing to step up, I doubted his and Susan's relationship would last another week. Susan would lose all respect for Aaron, and he'd undoubtedly blame me. I had really screwed this up not realizing Aaron's confidence was shot. But Jaycee could be a hell of a consolation prize. Not for Aaron, for me.

"You know I can't let that happen," said Jaycee.

"You can't let that happen? Just what do you plan on doing to stop me?"

"By imploring you not to?" she asked hesitantly.

"HA!" I answered rather loudly, causing the others to look our way. Jaycee glanced over at her nearly hysterical friend.

"Then by offering you whatever it takes," she said.

I just looked at her, trying to shake her a little bit. Throughout this story I've often mentioned that Jaycee's nipples noticeably got hard, and elongated. Did I mention elongated? They definitely got elongated. I found them fascinating. Each time though, they weren't getting longer and harder on top of their previous hard and long state. I just haven't been mentioning when they would go back to normal. I'm bringing this up now, because while I was stonily looking at Jaycee, her nipples definitely were once again getting harder, and longer. I swear, this girl must get excited by evil. I was doing my best impersonation of the devil himself and Jaycee looked like a cat going in to heat. Why is it that women are attracted to assholes? Maybe I should have been acting like an arrogant prick a long time ago, instead of letting Hannah push me around for years. Well, shit, even if I didn't want to act like a prick I shouldn't have let Hannah push me around.

"Whatever it takes?" I finally asked.

"Just name your terms so we can go back to the table."

Hell, the number one rule in negotiations is you never state how high you're willing to go, yet Jaycee was giving me carte blanche. I decided to push a little at that and name the most outrageous thing I could think of as my starting position. 'Whatever it takes'?!? Sure. Just then I remembered when Jaycee called me 'sir' a little while ago. That sparked an interesting idea. I'll just open with the top fantasy of every red blooded male on the planet.

"You become my sex slave for a week," I declared.

"A weekend," she countered. That was a quick comeback. She'd obviously been expecting something along these lines. And better yet she was agreeable to it. Was she really serious? Though come to think of it, maybe she wasn't offering that much. Before this conversation I thought it was pretty obvious that she was going home with me tonight regardless. I decided to stand firm to see how much movement she made off her initial counteroffer.

"Oh, now we're negotiating? I thought you said whatever it takes. I'm telling you what it will take. Otherwise, I'll take Susan's cherry. I understand a cherry is a prize. I've never had one before. I'm particularly looking forward to it."

"I ..." she began. "I've got one cherry left," she whispered.

"What?" I asked. What was she saying?

"My ass," Jaycee whispered, while looking down at the floor. "You can take my ass. I ... I ...I know you'd like it, so I'm giving it to you."

She 'knows' I'd like it? Well, well, well. I should have known. Everyone knows women talk about sex in more intimate details with each other than men would ever think of doing. And Hannah and Jaycee had been roommates since second year of grad school. But Hannah always swore to me that she wasn't like that. Obviously, however, she told Jaycee a lot. I loved anal play, though Hannah never consented to anal sex. But she would let me slip a digit in occasionally while we were going at it. Jaycee had just informed me that she knew this about me.

What was even more surprising was how big an offer Jaycee was making. Jaycee, in one of her all too candid conversations, had once told Hannah and me how she was petrified of anything sexual having to do with her ass. Any of the few guys who she'd fuck weren't allowed to get his hand anywhere close to her asshole without her freaking out. They were given the "no touching of my butt" talk early and often before they'd be let near her bed, and apparently she still had to kick one of three out the door before consummation.