Family Friends

*Note: I deeply apologize for the wait between chapters 1 & 2. I had some unavoidable projects at work that took me away from writing. I hope the wait was worth it. I am tentatively planning a third chapter that involves Rob, Jen, and Jen’s son Andy. But I would love to hear what you all would want to see and read about. Please comment and let me know! Thank you for reading!*

Jennifer Burnett looked at herself in the mirror and smiled. It had been 3 weeks since Rob had kissed her and since she had kissed him back. She hadn’t seen him since then, which was disappointing. But all the same, the kiss had awakened something new in her. She had gone on numerous dates. She and Kate Prescott had gone out drinking downtown and had gone to concerts together. She’d had a hangover for the first time in years. She was having fun again.

Something about having fun was contagious. Across all of her dating apps, her dm’s were consistently full. She had her pick of men these days. And although she felt bad thinking it, she was happy to be dating for herself for once. The dates she had gone on right after the divorce had been out of obligation: she felt like she had to. Now, she went on dates as much to show off her body, to toy with men, and have fun, as to actually find a partner.

She was pleased with her outfit tonight. Her dark washed jeans were tight and showed off her sizable, round ass. She wore a black halter top with a plunging neckline and a dark leather jacket over the top. The halter top and jacket were the perfect combo. It was obvious to anyone who looked at her that she had incredible breasts– 32 dd’s in fact– but thanks to the jacket, her cleavage was only exposed at certain angles. Any guy who wanted to stare at her tits couldn’t do it from the side but had to do it straight on, just the way she liked. And finally there were her shoes, the key to the whole outfit. They were two-inch bright red heels which put her height at 5’9, plenty tall enough to seem even more intimidating and powerful to men than she already did.

Her phone buzzed with a notification that her Uber ride was here. As she got into the back seat of the black BMW-5 series (she had even begun to splurge on her ride-hailing apps) she was greeted with a friendly hello from the driver, a Mexican man named Juan-Pablo who was in his mid-50s.

“Hi Jennifer, where are we off to?”

“Heading downtown to 1918, the cocktail bar on 6th and Fulton street.”

“Perfect. What takes you down there tonight?”

“I have a date,” Jennifer said with a coy smile.

“Oh, very lucky guy in that case.”

“Well, we’ll see how lucky he gets tonight,” Jennifer responded mischievously.

The Uber driver laughed and the drive proceeded the rest of the way in a professional silence.

As the car exited the interstate connecting the suburbs to urban downtown, Jennifer could tell it was going to be a fun night. It was barely 8 o’clock on a hot summer night in late-June and downtown was teeming with revelers passing from bar to bar, ducking in and out of restaurants and concert halls, and relaxing in groups in the city’s central park. She could feel the excitement and joy emanating from the city itself.

The car pulled up to the curb and Jennifer could tell that the bar was already packed. She could hear the noise from inside and saw a line of mostly young twenty-somethings waiting to get in.

“He picked a hip spot, at least,” Jennifer thought of her date, as she scanned the attractive bodies of the young people waiting in line.

Her phone buzzed once again. This time it was her date, Steven. He was already here and had a table near the front. Good, because Jennifer was not going to wait in line for any man.

“Have fun on your date, Jennifer,” the Uber driver said as she exited. “If it doesn’t go well, just send me a text, I’d be more than happy to come help you get out of there and show you a good time tonight.”

Jennifer laughed at his forwardness.

“Thanks for the ride Juan-Pablo. I will definitely keep your offer in mind.”

He smiled and waved at her as he pulled away. Jennifer straightened her jacket, tossed her hair, and walked into the crowded bar.

****************************************************************************************************

Despite the crowd, Jennifer saw her date almost immediately. The main bar was against the wall facing the street on Jennifer’s right. Lining both sides of the large rectangular room were snug booths. Two large, partially hidden, round booths dominated the back corners. On the floor between the booths and the bar were a smattering of different sized tables. Her date had managed to get a small table for two on the side of the room near the bar.

“Hi, Jennifer?” he asked tentatively, getting up from his seat.

“Hi, yes, you must be Steven, so good to meet you!” Jennifer said with a now practiced excitement. She went in easily for a hug, which Steven had clearly not expected. Jennifer smiled inwardly at Steven’s mild awkwardness. She already had a leg up on him.

As they sat down she finally got a chance to size him up in person and not just from his pics on the dating app. He was slightly taller than her in heels, maybe just over 5’10. His dating profile said he was a runner and it showed, he was thin and athletic looking but not particularly muscular. His light brown hair was thinning, but it was still there which was more than most men his age could say. He wore a plaid button down shirt that was tucked into light-wash, straight jeans. Steven was no catch, but he was no slouch either. Jennifer was curious to see if he would gain more confidence as the night progressed or if her looks would cow him into submission.

As they sat down–Steven with his back to the restaurant, facing the bar, Jennifer the opposite–she caught him trying to steal glances down at her cleavage. She didn’t blame him. In fact, she enjoyed it. But she felt like she had the answer to her question.

They sat in silence for a few awkward seconds until Jennifer figured she’d put Steven out of his misery.

“Have you been here before? How’d you end up choosing this bar? It’s very cool. I love the vibe, and all their antique decorations, and the atmosphere.”

Steven laughed awkwardly and took a sip of his water.

“Well, this was the top result when I Google’d ‘best places to take a first date.’ I’m also recently divorced so it has been a while since I’ve done this and didn’t really know where to go.”

“Yeah I know the feeling,” Jennifer said sympathetically, “divorces are so tough and it’s hard to get back out there. I’m glad you found this place, though! It is very cool.”

Steven smiled at this but clearly did not have any response ready. It seemed like he knew enough not to talk any more about his divorce, but not enough to actually engage her in any conversation beyond that topic. Luckily, the waitress arrived just in time.

“Hi you two! Have you had a chance to look at the menu? We have a number of specialty craft drinks available, as well as a full bar to serve any cocktail you desire.”

Feeling indulgent, Jennifer ordered a French 75, while Steven stuck with an Old Fashioned. When the drinks arrived, the conversation became easier.

Steven was only 40, 8 years younger than Jennifer, and he had two young kids, one was in elementary school, the other had just started middle school. The two parents commiserated about what it was like to have kids at that age and then Jennifer regaled him with the challenges that kept coming as they got older. Jennifer appreciated Steven’s sympathetic ear when she told him about her 22 year old son Andy who still lived in the basement and had foregone college to work at an ice cream store.

“It doesn’t get easier, does it?” Steven said

“No, it really doesn’t,” Jennifer said laughing.

The two shared a genuine and easy smile for the first time that night, and, also for the first time that night, Steven took the initiative.

“Should I go get us two more drinks from the bar? I feel like we still need to talk about everything else in our life besides our kids, so we’ll need another. And I don’t really feel like waiting for the waitress.”

Jennifer smiled.

“That sounds lovely.”

As Steven got up and headed to the bar for refills, Jennifer sipped the remainder of her drink, and scanned the action in the rest of the room. At the tables clustered around her own were mostly other couples on dates. She and Steven were probably the oldest two people here, but there were some other contenders that were in their late-30s. The booths that lined the sides of the bar’s brick walls were crammed with a more diverse set of revelers. There were a few groups of younger guys and a few groups of younger girls. Jennifer laughed to herself as she caught glances and drinks being exchanged between these booths across the bar. Probably college students or young professionals out for a nice drink before they went to the dance clubs or dive bars, she thought. A handful of the booths had middle aged couples on something like a double date.

Finally, her gaze arrived at the two large circular booths ensconced in the back corner of each wall. Jennifer was at an angle that allowed her to see almost all of the booth in the corner to her right–the one farthest away from her table and the doorway. Crowded into the booth was a large number of people most likely in their early-30s. A few of the men were bald or balding, and a few of the women had the beginnings of wrinkles on their faces or love handles on their sides. Yet, the table still gave off a youthful energy. Perhaps, Jennifer thought, it was a slightly desperate youthfulness: a group of friends who were a tad too old to be going out all the time beginning one last hurrah at a boozy summer weekend.

The booth that was at the end of the wall on her left was harder to see. A slight brick wall extended partially into the room, blocking at least half the table from her view. She tilted her head to see if she could get a better angle and was surprised at who she thought she saw. It was hard to tell at this distance through the noise and crowd of the bar, but in the center of the table–right about when it began to be hidden from her view– Jennifer thought she saw the blonde hair, winning smile, and button nose of Rob’s friend Rosie, and next to her, the long face, shimmering black hair, and busty bosom of his friend Asha.

Before Jennifer could confirm, a waiter approached the corner booth and blocked her view. Any attempt at figuring out for sure was foreclosed when Steven reappeared a minute later with two more drinks.

Not missing a beat from where the two had left off a few minutes before, Steven asked Jennifer about what she did for work and for fun. But Jennifer was distracted. Her heart had started racing when she had caught a glance of the corner table. All she could really think about was whether or not she had actually seen Rosie and Asha and, most importantly, about whether or not Rob was with them.

Jennifer told her now practiced answer to Steven about what she did for work. A few days a week she helped do some bookkeeping and office management for the Family Foundation. Other than that, she was trying to search for new hobbies. She went hiking more often now and was trying to paint. She kept her answers as short and vague as possible and immediately asked Steven the same questions in response.

As he began talking about his job as a civil engineer, Jennifer felt all the interest and focus draining out of her. He droned on and on about the sewers and parking lots he helped design for the city. She couldn’t be less interested. The less she focused on what Steven was saying, however, the more she felt herself scanning the room behind him, desperate for any sign that Rob was there, and that her hopes were not in vain.

“Jennifer,” Steven said. “Jennifer.”

Jennifer’s reverie was interrupted and she realized she had no idea what Steven had asked her, let alone any of the things he had just been explaining to her about parking lot engineering requirements.

“Oh? I’m sorry, what did you ask? I think that second French 75 is getting to me,” she said, trying to laugh off her inattention as lightly as possible.

“Oh yeah, this Old Fashioned is pretty strong too. I don’t remember the last time I drank anything other than light beer,” Steven said with a smile. “I asked if you had found any good hiking trails around here? I enjoy running outdoors, so any recommendations would be welcome.”

Jennifer’s panic slowly mounted. She did not want to admit that she knew essentially no hiking trails and that she’d only said that because it seemed like an easy thing to say in order to pass the conversation on to him. But she was saved at the last moment by exactly the person she wanted to see.

“Jennifer!” the voice boomed out, cutting through the din of the crowd.

She looked up and saw the broad, 6’2 frame of Rob Prescott walking down the aisle between the booths on the wall and tables in the middle of the serving floor. Despite the fact that she was on a date, she did not even try to hide her delight.

“Rob!” she exclaimed, bounding up from her chair and rushing as fast as she could in her heels to give him a hug.

It was undeniable how good he looked. He was in dark blue skinny jeans and a plain black shirt that fit snugly around his muscular body. As she pushed into his torso for the hug, she marveled at how firm and large his pectoral muscles were and how thick his biceps felt as he wrapped his arms around her lower back. She tried not to be obvious, but she let her hands lightly trace the outline of his traps too and almost gasped at just how big they were.

“What a small world,” Jennifer said, pulling away slightly from the hug. She was no longer up close against his chest, but they both had their arms wrapped around one another. “What are you doing here tonight?”

“Well it is too nice of a night to spend inside at home! So a bunch of us decided we should go out and celebrate the good weather. We’re starting here, but don’t know where we’ll end up. Looks like you’re having a good time tonight Jennifer,” Rob said, gesturing with his eyes towards Steven.

“Oh, right,” Jennifer said, embarrassed and flushing. She repositioned herself from within the hug. Putting one hand on the small of Rob’s back she pivoted, turning her torso and face away from Rob back towards the table where Steven was still sitting.

“Steven, this is Rob Prescott. His mom is my oldest friend, we went to college together.”

“Well, we didn’t go to college together,” Rob said gesturing at Jennifer, “but I’m sure she could’ve fooled all the sorority girls into thinking otherwise if she tried.”

Jennifer and Rob laughed while Steven smiled awkwardly.

“Yes, Rob’s mom and I went to college together,” Jennifer clarified, her face getting even redder. “I have known Rob literally since the day he was born.”

“She’s been a really great friend to my mom over the years and somehow still puts up with me!” Rob said with a smile and a squeeze, pulling Jennifer’s body into his side. She turned into his squeeze, rubbing her tits up against torso again and smiling up at his crystal blue eyes..

“Well you’re very easy to put up with, Rob,” she said, leaving her body pressed up against Rob’s side but turning her head to look at Steven. “He graduated with highest honors from Dartmouth and just took a job as a financial analyst at Western Trust Bank.”

“Oh congratulations! My office is actually in the building right across the street. It’s nice to meet you, maybe we’ll see each other around downtown,” Steven said, standing up and shaking Rob’s hand while Jennifer finally disentangled herself from Rob’s arms.

“Nice to meet you too, man. Hope you enjoy your date with this beautiful lady.” He smiled at Jennifer and pressed his hand one last time against the small of her back before he walked around their table towards a hallway behind the bar, ostensibly on his way to the bathroom.

“What a nice young man,” Steven said as Jennifer sat down. She was completely flustered and took a long sip of her drink to calm down.

“Yeah, I’ve known him forever. He’s an old family friend.”

“Very handsome young man, too. I think every girl in this bar was staring at you with burning jealousy when he came over.”

Jennifer took another sip of her drink.

“What were we talking about before?”

“Uh, hiking, I think.”

“Oh right, yes. I’m not sure I have any hiking suggestions that would surprise you. Where are your favorite running trails? I’m sure I could use the tips more than you could.”

Jennifer was relieved that she had managed to adeptly turn the conversation back to Steven and she slipped into another reverie as he began droning on about his running schedule and his favorite trails. All Jennifer could think about was Rob. It took Jennifer every ounce of restraint she had not to constantly look over her shoulder for Rob’s reappearance from the bathroom. Part of her felt like she needed to get every glimpse of him that she could because she was not sure when she was going to see him again.

Her patience and restraint was rewarded when he finally walked past their table on the way back to his booth. He nodded at Steven, who smiled back, and then turned to smile at Jennifer before he re-entered the booth and was hidden by the protruding brick wall. Jennifer wanted to sigh in disappointment but kept her eyes on Steven and tried to re-engage in the conversation. Her focus was short lived.

“Jennifer!” two high pitched voices squealed. She looked up to see the bright and smiling faces of Rosie and Asha. Steven looked more confused than ever. His date was being endlessly mobbed by young people. This time instead of a strapping, twenty-something hunk, it was two incredibly attractive twenty-something girls. One was a petite blonde in a bright red, mini-pencil skirt with a white crop top that exposed her incredibly toned abs, the other was an Indian girl in black jeans and a skimpy, tight blue tank top that left none of her 34cc boobs to the imagination.

Jennifer got up and gave the girls an enthusiastic hug.

“Rob told us you were here and we couldn’t believe it!” Rosie gushed.

“We had to come say hi!” added Asha.

“That’s so sweet of you two. It’s great to see you both and I’m glad you’re out having fun. By the way, this is my date for the evening, Steven.”

Steven got up from his seat and cautiously shook Rosie and Asha’s hands. It was obvious that they did not really care about him.

“I love this jacket,” Asha said, grabbing the edge of Jennifer’s leather coat and tugging it ever so slightly

“Jen, we need a picture with you. We told all of our friends about how hot you are for a 40 year old so we need to prove to them we were actually out with you tonight,” Rosie interjected.

Jennifer laughed and agreed while Asha handed her phone to Steven to take the picture.

“Oh my god, we look so good!” Rosie exclaimed after staring at the picture on Asha’s phone.

“Jennifer, do you have an Instagram? Def need to tag you in this.” Asha added while tapping away.

“No, I don’t have an Instagram,” Jennifer said laughing, “maybe you girls can help me set one up later.”

“Deal!” Rosie exclaimed. “This can be your first picture!”

“We’ll see you later, Jennifer. We are going to have a girls night soon, just the three of us!” Asha proclaimed as the two girls retreated to the corner booth.

Jennifer sat back down and both she and Steven sipped their drinks and caught their breath.

“You’re really a celebrity with these twenty year olds aren’t you?”

“Ha, I guess. I met Rosie and Asha the other day over at Rob’s mom’s house. They liked my fashion sense, I suppose. They’re sweet girls.”

“Well, you do have a good fashion sense,” Steven added awkwardly.

“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.

*********************************************************************************************************

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.