Jake pushed all of his chips into the middle of the poker table.

Anything I want?” he asked, letting the words hang in the air.

Everybody knew what was implied, and they were all looking at Jackie. She looked down at her cards one more time. She had a full house, aces over tens. The only hand that was out there that could beat her was a straight flush—Jake could only win the hand if he was holding the seven and eight of hearts. The way he had bet, she was fairly certain he had a flush, which she had covered.

She looked at Phil, sitting to her left. His raised eyebrows said that he wouldn’t make that bet, but of course he wasn’t in this hand. He didn’t know how good her hand was. It wasn’t like they were still dating, but she still whispered, “You wouldn’t mind, would you?”

He shrugged. “Hey, it’s your ass if you lose.”

And there it was.

The six friends had played cards almost every weekend since they were sophomores in college. At first, they had been three couples. Over the years, they had broken up, dated other people, and even dated other friends from their tight knit group. The poker nights remained, as did the friendship. Jake and Jackie had never dated, but she knew from Andrea and Sally that he had an enormous dick. Heck, even Phil had mentioned it when she had dated him.

Jake had a really big, thick dick. He had never gotten to enjoy anal sex as a result, even though it was the one thing that turned him on the most. He loved watching anal porn, particularly when a gorgeous porn star would take a big porn star dick in her ass. Jake had dated lots of girls back when they had been in college. Some of those girls had sought him out because they had heard he was so well-endowed.

Some of them even loved anal sex, but when they were faced with that massive trouser python, they invariably had the same response.

“There is no way in hell you are putting that monster in my ass.”

Jake even joked that the one thing he really needed was penis-reduction surgery. Andrea had been dating Jake on a rather casual basis over the past year or so. She had let Jackie know that the rumors about Jake’s dick size were no joke. She had breathlessly recounted over drinks how intimidated she was the first time she actually saw it hard and throbbing in front of her.

“Oh, I had heard it was big,” she said. “Sally confirmed that years ago, of course. I just figured it was maybe a little bigger than the guys I had been with before. But when he actually got hard and it was right there in front of my face…Jesus. I thought there was no way it was ever going to fit in my pussy.

“As surprised as I was by his size, though, I was even more surprised just how gentle he was. You know what a big jerk he can be. When he was with me in bed, though, it was like an entirely different guy was there with me. Jake was so tender. He touched me so softly. It was just intoxicating. By the time that big dick was filling me up, I knew he was not going to hurt me.”

Andrea had drained the rest of her drink with a shudder, “But there’s still no way that huge dick will ever fit in my ass.”

Jackie had actually enjoyed having a cock in her ass, going all the way back to high school. She was careful not to be the one to instigate anal with any of her boyfriends—she did not want to have that sort of reputation or the kind of attention it would bring. Once a guy was bold enough to take her asshole for the first time, though, she was happy to let him have it whenever he wanted.

Phil had never been so bold when they had dated a couple of years back. He had admired Jackie’s shapely little bottom and had even spanked it, but he had never been forward enough to bury his cock in it. Jackie’s eyes flitted across the table to where Tommy sat. He had been that bold, back when they dated in college. There was a twinkle in his eyes as he regarded her.

Tommy was getting turned on, and she could tell. Even though they had broken up eight years ago, he could still picture the lovely Jackie groaning in orgasm as his cock pounded her horny little asshole.

All of that flashed through her mind in mere moments as she sat at the table and tried to shake that off. Jake always beat her at cards, and she wanted so badly to rub his nose in it just this once. After all of these years playing together, they had gotten good at it. They could read each other to a certain degree, but they could also hide a lot of the more obvious tells from each other. Jake had to know she had a good hand. This might just be a ploy to scare her off of it.

The problem was she was so short-stacked in the game that she couldn’t take advantage of her killer hand. For once, she was convinced that she had Jake in a bind, but she needed more chips to really hurt him. She had breathed it as a rueful—and completely idle—comment to Phil, sitting next to her.

“Oh, I just wish I had your chip stack,” she had murmured, “I would give you anything you want to be able to force Jake all-in.”

But Jake had heard it. He had theatrically pushed his chips to the middle of the table, and said it loudly enough for everyone to hear.

Now it was up to her to make a decision. She was really trying to ignore what they all knew the stakes were, to make the correct poker read. She could still fold. She had about twelve dollars left in chips, and could still play for the rest of the night, but it would put her in a bind. They only played for a fifty-dollar stake on these poker nights.

Certainly, her ass was worth more than the seventy dollars that was currently in the pot.

Jackie narrowed her eyes as she regarded Jake. He still had that cocky smile he always wore at the poker table, the one that had tormented her for years when he took her chips. They both knew that was part of the act. It would goad her into overplaying when she had a good hand. In recent months, she had managed to ignore that cocky smile, and had held onto more of her chips than normal.

She had even been the overall winner twice in the past two months, but she hadn’t taken Jake’s chips from him directly. Jake’s eyes gave him away, then. Jackie’s narrowed eyes opened just a fraction when she caught the look of primal hunger that slipped through. He knew she had a full house. He was holding that seven and eight of hearts. He wanted her ass.

Jackie tried not to shake when that ran through her. She had done it! She had gotten the correct read, and now she could get away from this hand. Only…

Her hands played idly with her chips as she looked at the ceiling, as if she were calculating her odds one more time. Her peripheral vision took in everyone at the table. She was watching Andrea, to see what her reaction was. Jackie had not looked at her directly, and did not want to take for granted that Andrea would allow her boyfriend—casual though they might be—to fuck her friend in the ass.

The friendships at this table were far more valuable than satisfying any sexual itch she might have. That had always been the case with the six of them. Even though she and Tommy had been wild in college, Tommy’s wife was fine with him holding these poker games in their home, despite Jackie being part of it. They both understood that there would be no shenanigans between Tommy and his now ex-girlfriend.

Andrea’s face was flushed, her pupils slightly dilated, and her breathing was a little ragged. She was actually turned on by the thought of Jake’s massive tool opening Jackie’s ass. When she saw that, Jackie’s itchy bottom gave an involuntary twitch. She had been alone for too long. She was also alone among the three women at the table in that she was the only one who had not had the pleasure of meeting Jake’s legendary dick in person.

Her eyes met Jake’s then, and his eyes opened when he saw the look in her eyes. She was going to call him. They both knew that she was going to do it, and they both knew that he was going to win. Jackie grinned and narrowed her eyes again before she started the familiar trash talk that covered what they both knew this was about.

“Oh, I’m taking your bet, and all your chips,” she started. “You have had this coming for a long time, Jake. Sorry, Andrea, but I am taking your boyfriend down!”

She stood up and theatrically slapped her ace-ten on the poker table. There were whistles and an “Ooh!” from Phil when they saw her full house revealed. Jake’s eyes were wide as he looked at Jackie, knowing what she was doing. Only Sally caught on, and her breath caught briefly as she looked back and forth between them.

Jake recovered, and the obnoxious grin was back in place.

“Wow, that is a really good hand, Jackie,” he said. He was a dick about it, waiting until she reached to gather the pot before he dropped his cards face-up on the table. “Just not quite good enough.”

Jackie made a really good show of looking crestfallen, slumping back into her chair and reaching to drain the last of her mixed drink.

“I guess I’m out,” she finally said softly, before getting out of her chair to refill her drink.

Sally caught her eye as she rose to join Jackie at the bar. They didn’t have to say anything. Jackie’s show might have fooled Andrea, Tommy and Phil, but Jake and Sally knew.

“I can’t believe you did that,” Sally said.

The petite brunette shook her head and her eyes were wide. It made Jackie second-guess her decision.

Why did I do that? she wondered. I had it figured out. I should have just folded the hand. Why did I just agree to let that arrogant prick have me like that?

She had known Sally and Andrea for almost a decade, and they had shared some really intimate stories over the years. Between the three of them, they had dated a lot of guys. Jake had always seemed like the kind of guy that Jackie would never consider dating; he was just so arrogant and cocky, and it infuriated her. She had wondered how her friends could date such an annoying guy.

Sally was one of the sweetest, nicest people you could ever meet. It always seemed incongruous to Jackie that she would date a guy like Jake. As they regarded each other and mixed their drinks, Jackie once again recalled how Sally had explained it to her all those years ago.

“Oh, he’s not like that at all when we’re alone,” Sally had protested. “Really, that whole bravado thing he puts on is just a front. Those Business majors are all a bunch of sharks, and he has to act like that to protect himself. I’m telling you, Jake is one of the sweetest guys you will ever meet.”

Jackie had to hope that was true. She had bet her ass and lost, and she had no doubt that Jake would collect his favorite fantasy. Now she had to wonder if her horny bottom would be up to the challenge. She sat at the bar and sipped her drink, watching as her friends continued the poker game. She had to wonder, then, if her act had really fooled anyone at that table.

They had all been friends and shared these poker nights for such a long time. Jackie had felt like she had played it correctly, but now she had to wonder as each of her them looked at her over the remaining hour of that game.

Andrea was so turned on that she had trouble focusing on the game. She came over three times to get another drink, which was more than she normally had in an entire poker night. Each time she approached Jackie, she was breathing heavily and looking her over in a way that made Jackie moist. It had not occurred to her that Andrea might insist on being present when she paid up on that bet, and now it was something else for her to contemplate.

Tommy was noticeably hard when he grabbed another beer. This was not the first time their eyes met in a horny exchange over poker nights in his home. They had agreed that nothing could ever happen between them, and Tommy’s wife, Linda, kept him satisfied in the bedroom. Jackie had to admit that they made an excellent couple, far better than she and Tommy would have been.

“I can’t believe you did that either,” Phil breathed out softly when he finally came over to get another drink. The look on his face said that he thought she was playing to win. “That was a really bad beat,” he sighed.

Unlike Tommy, he did not seem to be turned on at the prospect of what was sure to happen to his ex-girlfriend’s sweet ass.

Jake was the last to approach her at the bar. He had practically stopped drinking after that sensational hand. He had been so preoccupied that he had surrendered a substantial chunk of his chip stack to Sally and Phil, and he was struggling to win some of it back. Jake whispered briefly into Andrea’s ear before he stood and made his way to the bar.

Jackie had to admit that his poker face now was the best she had ever seen. She had no idea what he would say to her. It just made her more anxious, and her pussy wetter. Jake was a tall guy, and she found herself looking up at his face as he mixed a rum and coke.

“You were serious, weren’t you?” he finally whispered.

“Yes,” she croaked after a moment’s pause.

“Andrea said it was okay,” he whispered again. “I’ll call you later tonight.”

Jackie looked down at the drink in her hand. The ripples on the pale surface of that White Russian let her know how much her hand was shaking. She turned back to the bar, setting down the drink and taking a deep breath.

* * *

Nobody had said anything else about the bet as they ended the card game and gave each other their usual hugs and good-byes. Jackie drove to her condo and let out a huge breath that she had been holding all night. She shook her head and mixed a really strong drink. Now that she didn’t have to worry about driving anywhere, she could get a good buzz and try to work through what she had been thinking.

She stripped and put on a lightweight robe, sipping her drink as she sat on her couch and waited for Jake to call her. She knew she would be playing with herself before she went to sleep, imagining what was going to happen. It had been three months since she had been laid, and that was certainly part of it. She would never have made that bet if she was getting any lately.

I don’t even like Jake, she thought once again. She shook her head. Is it just that I have fantasized about his big dick?

She didn’t think that was the case. If that had been it, she certainly could have had him years ago. Jake had made no secret that he found her attractive. She considered him a friend, but more as one of the friends in her group than a friend to her personally. They had only had a handful of personal conversations over the years, and those were teasing at best.

They had never gotten into a fight or anything like that. Jake had tormented her at the poker table, but it never carried over. He had given her some sound financial advice over the years, but that was usually financial advice he was giving to the group rather than anything personal for her. Following his advice had paid for this place, she reflected as she looked around at her comfortable condo.

When her phone finally rang, she jumped in her seat. She spilled a bit of her mixed drink on her robe, and she muttered to herself as she set the drink on the coffee table and picked up her phone.

“Hello?” she said.

“Hey.” The man’s voice on her phone was unrecognizable. Surely this couldn’t be Jake?

Jackie held her phone in front of her and looked at it. Nope, it was Jake. He just sounded nothing like the arrogant bastard from the poker table. She put the phone back to her face.

“Are you alright?” she asked.

“Um,” he replied, “I think so. You really shook me up with that play, Jackie.”

His voice actually sounded shaky to her. In losing that bet, she had gotten her long-standing wish: she had really gotten to that cocky bastard for once. Jackie grinned to herself when she realized it. Then she bit her lip. There was still the matter of paying off that bet.

“Is Andrea mad?” she asked.

“Sort of,” Jake replied. He sounded like he was being very careful as he chose his words. “I think she wants to be there, but I told her that was not going to happen. She asked if we should break up, since you would be giving me what I’ve always wanted. I really hope that was just the alcohol talking.”

Jackie could practically see Andrea making a speech like that, after she’d had a few too many drinks. She nodded into the phone. “That sounds like Andrea. I…I don’t think I could go through with it with anyone watching.”

There was an uncomfortably long silence.

“But you think you can go through with it if we’re alone?” Jake finally breathed into the phone.

The hunger in his voice had her dripping with anticipation. “Yes,” she breathed in response.

“When should we…?” Jake had never sounded so tentative, so unsure of himself. It just turned her on more.

“Tomorrow night, here at my place,” she said firmly. “If we wait any longer than that, I will chicken out for sure.”

“Okay,” Jake replied through dry lips. He cleared his throat, and Jackie heard him lick his lips before he continued. “Should I bring anything?”

“Nope,” she replied. “Just bring your self. I will take care of the rest.”

“Okay,” he said again. He wrestled with himself, thinking of and discarding a dozen things before he settled for, “Good night, then. I can’t wait.”

“Good night,” Jackie replied, hanging up.

In his apartment, Jake sat and stared at his phone for three minutes. He still could not believe this was really happening. His dick was as hard as he could ever remember it being, bulging obscenely in his slacks. It was entirely possible that she would still back down when she saw it, he reflected. It would not be the first time. He got his labored breathing under control, trying to temper his expectations. He had to prepare himself, to accept it when Jackie changed her mind.

Jackie had cleaned the stain from her robe and dropped it into the washer. Now, she was lying in her bed and was pushing her biggest, thickest dildo into her horny and lubricated ass. It was only the third time she had taken this monster back there, and it had her pussy on fire to think that she could be getting the real thing tomorrow night. It was a little painful, the way that thick phallus stretched her open. On the other hand, once the bulbous head was in her channel, it felt absolutely wonderful.

Jackie’s pussy exploded in orgasm, and she shook and took the time to catch her breath. She just hoped that Jake would be as gentle as her friends had assured her he could be.

* * *

Jake’s knock was firm on her front door the next evening. It was still light outside. Even though she had told him not to bring anything, he still held a lovely bouquet of flowers and a nice bottle of wine. He was dressed in a sharp pair of slacks with a dress shirt and a tie. He looked like he was arriving for a first date, Jackie realized as she looked at him through the peephole in her door.

She, on the other hand, was dressed in garters and stockings, with a matching lace demi-bra that emphasized her breasts. A lace gown was draped over the ensemble, but it wasn’t something she would want her neighbors to see her wearing. She worried for a moment that she had made herself look too eager. Certainly, her outfit was completely at odds with the ‘first date’ attire that Jake was wearing.