"Okay, okay," Alyssa said. "Smallest cock you've ever had. Loser buys the final round."
Juliet watched all three of her friends smile at the question. Had it been asked three drinks ago it was almost guaranteed no one would have answered, but girl's night out was nearing its end and everyone was tipsy enough to let the conversation delve into sex, as it almost always did when the four of them got together.
"I'll go first," Alyssa said. "His name was Robbie. It was my freshman year of college. He was, at most, four inches hard. He really had no idea how to use it, either, so he kept falling out. To this day it remains the worst sex I've ever had." She laughed. "He actually came while he wasn't even inside me. He was just rubbing his little dick over my pussy."
Angie raised her drink - which was nearly empty - and said, "I'm lucky. I've never been with a guy that's even below average."
"You've only been with three guys," Alyssa replied with a laugh. "How about you, Juliet? What's the smallest you've ever had?"
Juliet looked down at her drink and smiled as she thought of the cute guy she'd dated her first year out of college. He was a student teacher with her at the terrible school she'd been assigned to and they'd connected while complaining about the asshole students that filled their classes.
"His name was Jim. We were student teachers together. He was cute, though really pretty boring, in retrospect. Anyway, after a particularly stressful day at school we got drinks together at a local bar. We ended up getting pretty drunk and he invited me back to his place. I accepted, we got a cab, and eventually we stumbled into his tiny little apartment," Julie explained. "We pulled each other's clothes off and he did wondrous things with his fingers. I pushed him onto his couch and got on my knees to take his underwear off."
"And?" Alyssa asked as Juliet paused to sip her drink.
"And I saw a cock so small it seemed impossible to me," Juliet explained as she held up her pinky finger. "I swear, it was no longer than my little finger here. Thicker, yes, but definitely not longer."
"Oh, that poor guy," Lauren, who was sitting right next to Juliet, said.
"I know, right? Well, I was drunk enough that I had to stifle the urge to laugh. I know that's cruel, but it was an honest reaction," Juliet continued.
"Did you fuck him?" Angie asked.
Juliet shook her head and smiled. "I know it sounds awful, but what's the point of fucking a guy with a cock that small? I guess I could have gotten on top and did some grinding, but you can't do much with two inches. So, I gave him a blowjob. He came in thirty seconds - it had probably been a long time since a girl had taken him in her mouth - and he was kind enough to go down on me afterwards."
"Was he good?" Alyssa asked.
Juliet smiled and nodded. "Among the best I've ever had between my legs, actually."
"Better than Jay?" Lauren asked, referring to Juliet's husband.
She shook her head. "No one's better than Jay. Why do you think I married him?" They all laughed before Juliet said, "I assume that's the smallest and that the next round of drinks is on me?"
Her friends all nodded and Juliet pushed her chair back, got up, and headed for the bar to order up one more round of drinks.
"What can I get for you?" the bartender asked.
"Four shots, please," Juliet said. "Whiskey, middle shelf."
"Very good," the bartender replied.
"Go ahead and pour them four shots of top shelf Whiskey. On me."
Juliet turned to see a remarkably handsome man standing next to her. He wore a suit - and wore it exceptionally well - and his salt and pepper hair lent him an air of sophistication that she found surprisingly attractive.
"I'm Charles," he said.
"Juliet," she replied.
"It's nice to meet you, Juliet."
She considered turning down his offer to pay for her drinks, but everything about Charles communicated that he was a man in possession of a great deal of money, so instead she offered a smile.
"You're a beautiful woman," he said. "Though I'm sure you hear that all the time."
Her lips curled into a smile as Juliet's stomach fluttered. For a moment she struggled to believe that the man standing next to her - a man so good-looking and seemingly successful that any single woman in the bar would likely have gone home with him - was actually flirting with her, but the look on his face suggested that's absolutely what he was doing.
"I don't hear it all that often, actually," she replied. "Though I teach fifth grade and I've been married for eight years, so I don't exactly have a lot of opportunities in my life for good-looking men to tell me how beautiful I am."
Juliet felt an instant sense of embarrassment at her obvious flirtation.
"Your husband doesn't tell you you're beautiful?" Charles asked as he leaned a little closer.
Juliet caught a whiff of his cologne and a hint of desire followed, much to her dismay. "He does," she replied. "Of course he does. He's the only one who does, though. Outside of you, of course."
Charles smiled and again Juliet felt a flutter in her stomach. "Are you from Los Angeles?" he asked.
Juliet nodded. "I've lived here all my life, actually."
"Excellent. I'm new in town and I was hoping to find someone to help me get familiar with the best version of L.A. How would you feel about being that someone?" he asked.
Juliet couldn't tell for certain, but it seemed like Charles was asking her on a date of sorts. Despite his age - he was at least a decade older than her - she was surprisingly flattered by his interest. Still, not in a million years would she accept an invitation like the one he'd extended, even if he had no interest in sleeping with her. Doing so would have been an act of cruelty to her husband.
"Oh, I'm afraid my husband wouldn't like that," she replied.
The bartender delivered a tray with five shots of Whiskey on it and Charles pulled out his wallet and offered an American Express Black Card.
"I meant no offense," Charles said as he reached out and rested his hand on top of hers. His skin felt warm and soft and Juliet was astounded at the sudden rush of arousal that worked its way through her body. "I promise, I wasn't trying to coerce you into breaking your vows. Though I confess that my attraction to you did play a part in my desire to have you share your knowledge of Los Angeles with me."
Juliet made no effort to pull her hand out from beneath his. She held his gaze, too, and felt her pulse quicken as Charles stared into her eyes and smiled.
"I hope it's okay that I say that I'm attracted to you, Juliet," he said.
She nodded. "It is. It's...it's okay."
The bartender returned with Charles' credit card and a receipt and the older man lifted his hand from Julia's, added a considerable tip to the bill, and signed his name in a flourish. The bartender smiled, pulled the receipt away, and stuffed it into the register.
"Can I give you my number?" Charles asked. "I'm sincere about my desire to learn about Los Angeles from someone who's lived here all her life and I'd love for that person to be you."
Juliet should have refused, if for no other reason than she felt an unusual and potentially irresponsible sense of attraction to Charles. Even taking his number felt like a betrayal of her husband, and yet that didn't stop her.
"Yes, of course," Juliet said as she pulled out her iPhone and opened the contacts.
She handed the phone to Charles and his fingers danced over the screen as he added his information and set the iPhone on the bar. "It was a pleasure meeting you, Juliet, and though I understand I probably won't ever hear from you, I can promise you that I won't soon forget you."
He took her hand and gently kissed the back of it before offering an effortlessly charming smile and walking away. Juliet watched him go and she found herself hoping he'd look back. He didn't, though. Instead, Charles exited the bar, leaving Juliet just a little disappointed. She took a deep breath, grabbed the tray of shot glasses, and headed back to the table.
"What was that?" Alyssa asked as she approached.
All three of Juliet's friends were staring at her and she suddenly felt a deep sense of embarrassment. She'd been so caught up in her flirtation at the bar that she'd completely forgotten that her four closest friends in the world were watching.
"Who was that guy?" Lauren asked.
Juliet set the shots on the table, took a deep breath, and said, "His name is Charles. He said he just moved here. He asked me if I would lend him my local expertise of Los Angeles in helping him get settled."
"It looked like he was trying to fuck you," Alyssa said.
Despite knowing that she should outright deny the notion, Juliet again felt a flutter in her stomach as she thought of a man like Charles - a man with looks, charm, and wealth - desiring her. "You really think so?" she asked with far too much excitement.
All three girls at the table were silent as they stared at Juliet. It was as if they'd all had the same realization and no one was willing to give voice to it.
"Holy shit," Alyssa finally said, "you were into him."
Juliet shook her head as she sat down.
"Yes, you were into him."
She shook her head again.
"Do you blame her?" Angie asked as she grabbed a shot. "There's something so hot about a gorgeous older guy, isn't there? Plus, he was practically dripping money. What woman wouldn't get a little bit excited when someone like that makes it perfectly obvious he wants you?"
"Fair enough," Lauren said as she and the rest of the girls picked up a shot glass. "I don't think I would have handled myself any differently than you did, if I'm being honest."
"Me neither, now that I think about," Alyssa replied. She raised her glass and added, "In fact, why don't we all drink to the thrill of a hot older guy wanting to fuck one of us."
Juliet raised a glass with the rest of her friends and threw back the shot. It went down smoothly - the expensive stuff really was better - and then she closed her eyes and for just a moment allowed herself to enjoy the thrilling - and arousing, as it turned out - idea that a man like Charles wanted her.

Juliet felt guilty the moment she saw Jay's smiling face when she got home that night. He took her into his arms for a warm hug and she closed her eyes, rested her head in the crook of his neck, and thought of how hurt he would have been if he'd known that she hadn't immediately shut down Charles' flirtation at the bar.
"Welcome home," Jay said with a smile as he ran his hands down her back and gave Juliet's ass a tight squeeze.
She looked up, smiled, and kissed her husband. He squeezed her ass a little harder and Juliet moaned into his mouth. Her lips remained parted and she offered her tongue as arousal surged through her body.
"Take me to bed," she said.
Jay smiled, picked her up, and carried Juliet down the hallway as she wrapped her legs around him. She kissed his neck and moaned as the anticipation of getting fucked deepened her arousal.
"I want you, Jay," Juliet said as he stepped into the bedroom. "I need you."
He set her in the bed, pushed her skirt up around her waist, and pulled her panties off. His fingers moved over her inner thighs and he dropped down and attached his lips to her clit. His tongue flicked back and forth over her sex organ, sending slow, beautiful waves of pleasure through Juliet's body.
She closed her eyes, smiled, and ran her fingers through his hair as he dipped his tongue into her pussy before returning to her clit once more.
"Jay, please, fuck me," Juliet pleaded.
He looked up and smiled. He stepped back and hastily undressed as Juliet pulled off her top and unhooked her bra, leaving her in a skirt and heels.
Jay crawled into the bed and between her legs. They kissed as Juliet guided his cock inside her. She moaned and he kissed her neck while slowly filling her.
"Fuck, Jay, you feel so good inside me," she said softly. "Now fuck me."
Their lips met as he did just that. Every time he bottomed out inside her Juliet felt a small explosion of pleasure at the stimulation of her extra sensitive clit. That pleasure spread through her body. Her fingers and toes tingled with erotic delight. Her head swam with pleasure. Her pussy dripped as she got wetter and wetter.
Juliet wrapped her legs around her husband and closed her eyes as he fucked her exactly like she needed to be fucked. Then, without warning, Charles popped into her head. Suddenly she was imagining him on top of her. Suddenly she could smell his cologne. Suddenly she could feel her fingers moving through his salt and pepper hair.
"Oh, fuck!" she screamed as pleasure tore through her body.
Juliet opened her eyes to try and push the imagery out of her head - and it worked - but her body demanded she close her eyes once more. It demanded that she chase the most pleasurable orgasm possible, and for whatever reason that meant imagining another man on top of her and inside her.
She closed her eyes. Charles was on top of her again. His cock was inside her. The scent of his cologne filled her nose. His strong, soft hand was on her breast instead of Jay's. His fingers were gently pulling on her nipple instead of her husband's.
"I'm close, baby, I'm close," she said.
For a moment Juliet thought she might call out Charles' name. She thought the insane fantasy her brain was pursuing would overwhelm everything and she'd break her husband's heart.
Thankfully, she didn't. Instead, Juliet experienced a massively powerful orgasm right as Jay came inside her. She wrapped her arms and legs around him and held him tight, mostly because she felt too guilty to look at his face in that moment, for it was the first time she'd ever cum with her husband while thinking of another man.
Eventually, Juliet loosened her grasp and Jay pulled out of her and rolled onto his back. She cuddled up next to him and watched his chest rise and fall as she smiled from the way her pussy continued to pulse in the aftermath of such a satisfying orgasm.
"You should go out with your friends more often," Jay said with a laugh.
Juliet kissed him on the cheek. At least her imaginary infidelity had meant resulted in Jay cumming just as hard as she had.

Midnight had long since come and gone. Jay was sound asleep next to her as Juliet stared at the ceiling. She rolled onto her side and saw her phone on the nightstand. She thought of Charles resting his hand on top of hers. She thought of him kissing it. She thought of his smile, the confident way in which he talked, and the unexpected arousal she'd felt as he flirted with her.
That arousal returned. It crept up on her like it had slipped under the covers and into her pajama shorts. Juliet held her legs together as tightly as possible in the delusional hope that she could somehow stave off the elicit desire.
She failed horribly. She grabbed her phone off the nightstand. She pulled up her contacts list. She found Charles' name. She opened a message and her fingers hovered over the on-screen keyboard as she contemplated doing the unthinkable and sending him a message.
"Hey. This is Juliet. From the bar. I thought about what you asked, about helping you get to know your new home. I think I'd like to do that."
She read the message and then quickly deleted it. Then she typed it out again. Her finger hovered over the send button as her pulse raced. Juliet knew she shouldn't message Charles. She knew she was doing it for the wrong reason. She had no intention of cheating on Jay, and yet it was the allure of a man like Charles that made her want to spend more time with him.
Juliet sent the message. She hadn't entirely committed to it. She'd only said she thought she'd like it. She could back out. Or, perhaps Charles wouldn't even respond. Perhaps all he'd really been trying to do at the bar was fuck her.
She saw the three dots. He was already typing out a message. Juliet glanced at Jay to make sure he was still asleep and then turned her attention back to her phone and felt her heart pounding remarkably hard as she waited.
"That makes me very happy, Juliet," Charles replied. "The thought of spending even a little more time in your presence thrills me. But, I understand that you're a busy woman with a husband and a career, so if it makes it easier for you - if it helps you go from thinking you'd like to do it to actually wanting to do it - I'd be more than happy to pay you for your time. You could tell your husband that you picked up a side gig for some extra money."
It was a kind offer, and one that would, in fact, make it a great deal easier to explain to Jay why she was suddenly spending time with a man like Charles.
"I'd like that," she texted back.
"Excellent. Why don't you come over for dinner this week? I'll cook. Does Wednesday sound good? You can share some of L.A.'s secrets with me and we can plan a few outings. Oh, and make sure you bring a bikini. I have an exquisite pool and I'm not letting you leave until you've gone for a swim. I promise, you won't regret it."
He wasn't being particularly coy about his desire to do more than pay Juliet for her local expertise. She found it exciting, though, to the point that her pussy tingled at the thought of Charles seeing her in a bikini. Guilt almost immediately followed that thought, though it did very little to extinguish her desire.
"Send me your address," Juliet replied, knowing full well that she was doing something foolish. "And I'll see you Wednesday."
He sent his address and Juliet set her phone down, closed her eyes, and ran through her bikinis in her head. The previous summer she'd bought a red thong bikini that she'd never had the courage to wear. She thought of wearing it for Charles and her hand slipped under the covers and into her shorts. Her finger found her clit and she very nearly moaned the moment she touched it.
Juliet masturbated as she thought of wearing her red bikini for Charles. The thought of being so bold, so wild, so daring...it turned her on in an intense manner, so much so that she came within thirty seconds. Her body trembled so hard she thought Jay might wake up. Thankfully, he didn't, and Juliet closed her eyes and fell asleep in the aftermath of another fantastic orgasm.