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"Uh, thanks."
Realizing he had wrong-footed himself in the conversation, Steven called an audible.
"I'm going to run to the bathroom quick, if that's alright."
"Of course, I don't control your bladder, Steven," Jennifer responded, barely masking her annoyance.
Steven laughed, doing his best to mask the awkwardness, and excused himself. Jennifer sipped her drink and breathed a sigh of relief that she had a few moments without Steven where she could re-organize her thoughts.
She had less time than she thought. Almost as soon as Steven had fully disappeared down the bathroom hallway behind her, Rob, Rosie, and Asha's big group in the corner booth got up and moved to the exit. While the rest of the group piled through the door and out into the night--Rosie and Asha drunkenly waving at Jennifer the entire time--Rob sat down in Steven's seat.
"Don't say anything, Jennifer," Rob began, without a hint of playfulness or levity in his voice. "Here's the deal. If you're enjoying your date, I don't want to disrupt anything. You stay here, have another drink with Sam or Scott or whatever, and enjoy your night. But, if you wanted a little more excitement than that dude can give you, I have a proposition. We're going down to Ol' Buddy's, the karaoke dive bar about a ten minute walk away. We will wait outside of here, around the corner, for five minutes exactly. If you want to come, say your goodbyes to Sean or Simon and come meet us, and we'll walk together. If you're not out there in five minutes, I'll take that as a no, and we'll head over without you, no hard feelings. Deal?"
Jennifer was shocked. She didn't know what to say.
"Let me think about it."
"Ok, you have five minutes. See ya, Jennifer."
Rob got up and walked out the door without looking back.
Jennifer's heart raced. Her breasts heaved. And her thoughts were a jumble. It was obvious to her that she wanted Rob. She had wanted him from the moment she saw him on his mom's terrace. She had wanted him even more after he kissed her. She hadn't stopped thinking about him in three weeks. But now she actually had to act on her fantasies. Could she really just ditch her nice, if awkward date, for her best friend's 22 year old son? She knew she wanted to, but didn't know if she could.
Her anxiety was growing by the minute. She glanced at the door of the bar, hoping she'd see Rob, or Rosie, or Asha, or any of their friends, but no one was there. All that was visible was the dark oak frame of the door and a small, frosted glass window. Turning around in her chair, she checked the bathroom hallway. Steven had just exited. She turned back around before he saw her looking and took a deep breath.
"So," Steven said, with renewed confidence as he sat back down, "would you like one more drink?"
Jennifer was indecisive for all of 1 second before she gave in to her gut instinct.
"I'm sorry, Steven. Something actually came up and I have to leave. I had a really nice time though. I hope you don't mind picking up the tab, but I have to go right away."
Jennifer stood and gathered her purse and put herself together. Steven stood up too.
"Is everything ok?"
"Oh yeah, everything's fine. Just something came up at home and I've gotta get back. You know how it is with kids."
"Oh, ok," Steven said, the disappointment obvious in his voice. "That's totally fine. This was a lot of fun, I'd love to see you again sometime. Maybe we could go for a run or a hike."
"Maybe, I'll think about it," Jennifer said, obviously in a rush.
"Ok well it was great to meet you." Steven went in for a hug.
Jennifer gave him a weak hug. She wrapped one arm around him in a hurry and kept the rest of her body away from his.
"Thanks for the drinks!" she called over her shoulder and pushed through the bar door into the warm summer night.
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The humid summer air rushed into her lungs. It felt enlivening in a way the cool AC of the bar never had. This was a summer night and Jennifer was taking a risk. As her heart beat accelerated she took one deep breath to steady herself, secured her purse over her shoulder, and walked around the corner of the bar.
She was greeted with an uproarious cheer from Rob and his friends.
"Jennifer!" Rosie and Asha screamed, running over to embrace her. Jennifer staggered as the drunk girls collided with her body, but couldn't help smiling.
Encumbered by Rosie and Asha's embrace, and a flood of relief, happiness, and excitement that she had made the right decision, she quickly scanned the rest of the crowd. There were three other boys, all around Rob's age but none as big as him nor as good looking as him. They were howling and clapping like banshees, no doubt impressed that their friend had coaxed out a milf. In addition to Rosie and Asha, there was one other girl who Jennifer didn't know--a leggy blonde with softly curled hair, blue eyes, and average breasts. She too was howling her delight alongside her male colleagues. Then finally Jennifer's eyes met Rob's. He wasn't saying anything, just softly smiling. Jennifer smiled back.
After a solid minute of whooping and hollering, the group settled down and the majority turned to walk to the next bar. Rob did too, but glanced over his shoulder at Jennifer, who had now (involuntarily) locked arms with Rosie on one side and Asha on the other.
"Have you ever been to Ol' Buddy's?" Rosie asked.
Before Jennifer had a chance to answer, Asha chimed in.
"It's so much fun. PBR's are only like $3 and a shot and a beer is only like $5. Everyone gets wasted which makes the karaoke amazing."
"What's your go-to Karaoke song, Jen? Mine's 'We are Never Ever Getting Back Together' by Taylor Swift."
"Oh my god, I would die for TSwift," Asha added. "We are so taking shots and singing karaoke together Jen."
Jennifer couldn't help herself from laughing at the girls' exuberance. It was gratifying to feel so included and frankly, to be so revered by two girls in their twenties. A far cry from the experience she had with her son everyday.
"I'm old school," Jennifer finally interjected, "I like Bon Jovi's 'Livin on a Prayer' or maybe 'Born to Run' by Bruce Springsteen."
"The boss!" Rosie shouted, "I love him. So classic. Never goes out of style."
At this Asha began singing "Cause we never go out of style, we never go out of style!" at the top of her lungs and the two girls nearly collapsed into laughter while trying to sing the rest of the song. Luckily, they had at least caught up to the rest of the group, and as Rosie and Asha drunkenly stumbled belting Taylor Swift all the while, Rob cut in.
"Looks like you're in need of an escort now," Rob said to Jennifer, casting a mocking glance at Rosie and Asha who were now ahead of the entire group, urging everyone on to the karaoke bar.
Rob put out his hand and Jennifer gladly accepted it, sidling up against him as close as she could, enjoying the feeling of his firm, muscular, immoveable frame next to hers.
They walked in silence for a while. Not awkward silence, but companionate silence. The drunken antics of Rosie and Asha dominated the attention of the rest of the group of friends, giving Jennifer and Rob relative privacy to walk quietly in the back of the group. The sounds of a busy summer night in the downtown bar district filled the air. Lights poured out from every bar, restaurant, and venue that was open, making 10:30 at night feel rather early, not late. Every so often the pair glanced at each other and smiled, both still in slight disbelief that they were out together, holding hands, a night of adventure ahead of them.
Ol'Buddy's couldn't have been more different than 1918. It was packed to the gills and there was no AC to be had. The humid air reeked of spilt beer and sweat as bodies packed in close to get cheap booze and get in line for karaoke.
Jennifer was thrilled. She couldn't remember the last time she had been in a bar like this. College, maybe. What was more, because the bar was packed like sardines, she was forced to be as close to Rob as possible. His strong hand led her through the crowd and he easily got a space at the bar itself. Jennifer squeezed in, wrapping her arms around his torso and pushing her breasts into his side.
"What do you want!?" Rob yelled over the din, their faces barely an inch apart.
Jennifer nuzzled his cheek with her nose, ostensibly to talk more directly into his ear.
"I'll have whatever you're having!"
He looked at her with a quizzical "are you sure?" glance, to which she responded by grabbing the back of his head and kissing him hard.
Rob was stunned for a moment but then quickly wrapped both his arms around her waist and pulled her even closer into his body. Jennifer wrapped her other hand around the back of his head and let her body slowly writhe with the rhythms of the kiss. Having pulled her in as close as possible, Rob began kissing her harder, opening his mouth wider and giving her more and more tongue. Jennifer responded in kind.
Even through the noise of the bar, she heard Rosie and Asha shriek and begin chanting "Jen-i-ffer, Jen-i-ffer!" they were quickly joined in by the rest of the friend group that had clustered behind Rob and Jennifer at the bar.
They finally broke the kiss off but neither could contain their smile. She'd only had two drinks that night, but Jennifer's head was already swimming. Maybe it was the heat, and the crowd, and the music, or maybe it was just her delirious joy at being out with a man she truly wanted. Maybe it was all just lust. If she had been twenty years younger, she probably wouldn't have wasted anymore time at the bar and found the nearest place she could fuck this twenty two year old stud.
Rosie and Asha interrupted her thoughts with a hug, having fought their way through the crowd and up to the bar. Jennifer gladly accepted their hug and saw Rob's friends similarly grabbing his shoulder and patting his back in congratulation.
Rob quickly began passing out shots of whiskey and cans of PBR to Jennifer, Rosie, Asha, and the rest of their friends assembled behind them.
"Still happy with your decision?" Rob asked, yelling over the crowd and nodding at the whiskey.
"Couldn't be happier," Jennifer said, ripping the shot and pulling Rob in for yet another kiss, this time to even more uproarious cheers from the crowd.
Jennifer did not have much time to bask in her newfound romantic glory. As soon the two broke off their second kiss, Jennifer was pulled into the crowd.
"Come on, we're next at karaoke, all three of us are singing Bon Jovi!" Rosie yelled at Jennifer. "Let's go!"
The two girls led her by her hands through the crowd and up onto the karaoke stage. The stage was crammed against the back wall of the bar, but every single person was still visible, and almost all eyes turned to the odd trio of attractive women at the microphones.
"Now singing Jon Bon Jovi's 'Livin on a Prayer' it's Jennifer, the hottest cougar in town, and her backup singers, Asha and Rosie!" the dj boomed out.
The bar screamed it's approval at Jennifer "the hottest cougar" in town, while Jennifer shot Rosie and Asha a mock-angry look. They were too busy laughing to notice and then the song began.
Jennifer found Rob at the far end of the bar and locked eyes with him, thinking that would be the easiest way to get through this embarrassment, and began singing.
At first it was awkward. Rosie and Asha were no help, they were doubled over with drunk laughter behind her. Jennifer's singing was low and quiet. But the bar was paying attention and the din lessened in response. She was nervous. No one else's karaoke song had garnered this much attention from the drunk young adults thronging on the cramped bar's dance floor. She kept her eyes locked on Rob whose face was frozen in a playful, coy smile.
But that all changed once she hit the chorus. Not only did Rosie and Asha finally join her, but so did the whole bar.
"Woah, we're half way there, woah, livin on a prayer!"
From that moment on Jennifer let it rip, and the whole bar backed her up whenever they knew the lyrics. Jennifer's performance ended with thunderous cheers and plenty of catcalls too. She responded to them simply: by kissing Rob once again and whispering in his ear "Let's get out of here." He was only too happy to oblige. Jennifer took his hand and led him out of the crowd into the summer night. This time there was no mystery about what would happen next.
**********************************************************************************************************
As soon as they were out of the bar, Jennifer and Rob's hands were all over one another. They were every bit as drunk with love and lust as they were with alcohol. With their arms wrapped around each other's waists, they staggered into the night.
"How far is your new place?"
"It's close," Rob assured her, "just a few blocks back towards downtown. That big building, the Center City Lofts."
As they walked Rob let his hands roam onto Jennifer's round ass that barely fit in her tight jeans. He squeezed it hard and made her squeal with delight in the process. By the time they piled into the building's elevator they could hardly contain themselves.
When the elevator doors shut, Rob barely had time to press the button for the 8th floor before Jennifer pinned him against the wall and began making out with him. One of her hands pushed up his shirt and felt his abs while the other fondled his belt buckle. Rob responded by using his free hand to grab one of Jennifer's breasts.
"I've been waiting 10 years to do that Jen," he whispered, as her kisses moved from his mouth to his neck.
Luckily no one was there when the elevator door opened. The two stumbled to Rob's apartment with tussled hair, a belt buckle half undone, and their shirts messy from so much fondling.
"Oh my god, Rob, this place is amazing" Jennifer exclaimed as soon as they got inside the doorway.
Rob's apartment was newly built and decorated in a modern style. Immediately on the right was a kitchen with new, stainless steel appliances, light grey granite countertops, and a bar that connected it to the living room that was straight ahead of them. It was the living room that was the real show stopper. It had high ceilings and massive windows that ran the length of the wall. Through the windows was a completely unencumbered view of the downtown skyline. A big, soft-grey sectional couch was in the middle of the room facing an enormous, wall-mounted flat screen tv. Two hallways protruded from each side of the living room, presumably towards the bedrooms.
They didn't get that far. When the door clicked shut behind them, Jennifer immediately dropped to her knees and began the work of undoing Rob's belt buckle that she had begun in the elevator.
"I've been thinking about what your dick feels like since the moment I saw you on your mom's balcony, Rob."
Rob responded by throwing off his black shirt and exposing his boulder like pectorals, muscular torso, and six pack.
"You're not going to blow me before I get to finally see those tits Jen. I've had a crush on you way longer than you've had a crush on me, remember? I've been waiting ten years, you've only been waiting a few weeks."
Just as Jennifer undid his belt buckle and whipped it out of the loops in Rob's jeans, she felt his powerful arms grab her under her armpits and pull her up. Rob immediately began tugging on her leather jacket, and she helped him by smoothly sliding out of it. All that was left was her loose black halter top.
As Rob's hands pawed at the halter top's soft fabric, Jennifer grabbed his forearms and pushed herself up against his bare chest as close as she could, lightly kissing his neck, and then his ears, and then finally moving back to his lips. In between kisses she whispered to him.
"Have you really had a crush on me since you were 12, Rob? Did Little Robby masturbate to his friend's mom? If you want to make your fantasies come true, Robby, you have to tell me about them."
"Do you remember that one Labour Day weekend when both of our families went to the lake? I think Andy and I were only 13 or 14?"
"Yes I do," Jennifer said, slowly kissing her way down Rob's body.
"That very first afternoon, when we were on the boat was the first time I remember seeing you in a bikini. I faked feeling sick so I could go to the bathroom and masturbate to you."
"Oh yeah, what else?" Jennifer said, as she was kissing Rob's abs.
"At my high school graduation party, I was trying to work up the courage to make a move on you. Like a porno movie or something. Obviously I didn't. But I did try to stand next to you in all the pictures and cop a feel of your tits and ass."
Jennifer laughed as she began to peel back Rob's black boxer briefs.
"I remember that. You were actually pretty subtle. You were so sweet and harmless back then I didn't really mind."
Her thought was broken by finally taking Rob's boxer briefs off completely and seeing his cock for the first time. It was fully erect and perfectly shaved. It had to be at least 8 inches, maybe 9. Not only that, but it was thick. Smaller girls probably had trouble wrapping their hands around it. And it was all capped off with a huge, purple circumcised head.
"Oh my god," Jennifer said in awe, "If I had known your cock looked like this I might have let you fuck me back at your graduation party."
"Now it's my turn," Rob said picking her up once again. Their eyes met and Rob flashed his characteristically soft and coy smile at Jen as he pulled her halter top over her head exposing her black lace bra that was barely containing her plump and fleshy tits.
"Take your jeans off. I want to see all of you in lingerie before we start."
"Only if you put on some music," Jennifer replied.
Rob began casting what was no doubt the sex playlist he used with all the girls he brought back to his bachelor pad from his phone to the speakers in the living room. Meanwhile Jennifer pulled her jeans down slowly, writhing to the rhythm of the music and treating Rob to a view of every angle of her body as she exposed it to him.
Rob stood watching with delight as the milf he had masturbated to for years stripped down to her lingerie in front of him. Finally, Jen stood there in nothing but her black lace bra and black g-string.
"Now you can blow me, Jen."
"Yes sir." Jennifer said with relish.
Jennifer wasted no more time. She got down on her knees once again. Cupping one hand around Rob's balls, Jennifer moved up his shaft with one kiss at a time until she got to his large purple head. Rob ran his hand through Jennifer hair and held the back of her head while she looked up at him with big "fuck me" eyes, before she swallowed his dick whole.
It had been years since Jennifer had given a blowjob, but she had been one of the best in college and it showed. Rob groaned in surprised delight as she deep-throated him. Coming up for air, she spat back out all of the saliva in her mouth onto his dick and started rubbing it with her free hand. Rob's hand forced her head back down and she went as far as she could, feeling the tip of his cock all the way at the back of her throat and covering it with more warm saliva.
At her own desire as much as at Rob's not-so-subtle direction with his hand on her head, she began bobbing up and down. She went slowly at first, making sure her lips were wrapped firmly around the skin of member and that she covered every inch of his dick the warm juices of her mouth. She sped up. She wrapped both her hands around Rob's dick and rubbed it vigorously as her mouth moved up and down and up and down.
Catching her breath for a minute she looked up at Rob.
