Former Party Girl Goes Wild
The sales team at alphaData had been working tirelessly to secure a major client, and when they finally landed the big deal, it was time to celebrate. As far as the small but nimble team was concerned, this night had been months in the making. Now, on a sleepy Thursday evening, with a five-year contract (and all the commission) under their collective belt, the team decided to go out for drinks at Mil-Q Toast, a trendy downtown bar with an industrial-chic vibe and exposed brick walls adorned with eclectic art.
For Tom, who just a few months ago was alternating between writing papers and doing keg stands at frat houses, the new change of venue was a whirlwind. Having graduated with a freshly pressed bachelor's degree in communications, he took the first job that would have him--a sales gig at this tech firm. Now here he was, making more money than he had ever made, surrounded by a different caliber of people. The place was buzzing with people, the atmosphere electric with laughter and conversation. Sarah, the account manager, and Julian, the UX designer, joined Lisa and Tom for the night.
Tom was fresh out of college, a young 23 years old, and eager to prove himself as a sales representative. With dark hair, a fit physique, and a charming smile, he quickly became popular among his colleagues.
Tom admired Lisa, who had been a sales rep at alphaData for several years. She was known for her sharp mind and unwavering professionalism as much as her killer figure. Joan Holloway from Mad Men was mentioned a lot by clients--something that she used to her advantage often. At 36, she exuded confidence and a magnetic allure that drew people to her effortlessly. Her long, wavy ginger hair framed her face, accentuating her bright green eyes, and her curvaceous figure was often highlighted by the elegant yet form-fitting clothes she wore to work.
Tom stole a peek; she must have at least a double D cup. And those hips...and that ass. Jesus, that ass. Tom's eyes ran up and down Lisa's body. She was older but carried herself so...not-lady-like. Tom got a sense that she would have felt right at home at Greek row back in college. It was strange to think this woman was married with a kid with the stuff that came out of her mouth sometimes.
He stood behind Lisa at the hostess' line and looked down. That gigantic ass. Immediately, Tom felt his member twitch. He remembered one time Lisa needed to unplug her computer. She was wearing low-cut jeans then, at the office, on all fours, and Tom remembered seeing a pink thong sticking out of her backside. Wild girl at heart? Tom wondered.
Suddenly, Sarah nudged Tom, grinning. Back to reality. Tom did his best to play it off. He was just lost in thought, but Sarah didn't buy it.
"Eyes on the road, Flint," Sarah said, using Tom's last name.
The group got a table and began to order drinks and food. As the night progressed, they shared stories and laughs over several rounds of drinks.
"I thought that old man would never be happy," Julian said, knocking back a beer.
"It took a while," Lisa interjected, "but once we figured out that even though that kid's door says CEO, his dad was really calling the shots. Once we figured out what he wanted...it was a cakewalk."
"You mean once we walked those cakes in front of him," Sarah said.
"There's something to be said about womanly charm," Lisa said slyly as she puffed out her chest and leaned across the table to Julian, exposing her ample cleavage.
"I'll say," Julian responded.
"Lisa's just a great salesman. Woman. Person." Tom interjected, correcting himself at the end.
"Give that feminist ally shit a rest, Flint," Sarah said. "You know, Tom, I've seen you checking out Lisa. Don't think I haven't noticed."
Tom shut up and blushed.
Lisa laughed, playing along. "Oh, he's harmless. Besides, who wouldn't check out these?" She gestured to her ample chest, her smile full and flirtatious.
Sarah grinned and corrected her, "Actually, Lisa, I think he's more interested in your dumpy. I've caught him staring a few times."
Tom blushed even redder but laughed along, his eyes lingering on Lisa a little longer than necessary.
"What the fuck is a dumpy?" Julian asked to laughter.
Eventually Sarah and Julian decided to call it a night early, leaving Lisa and Tom to continue the celebration alone. Sarah teased Tom as she prepared to leave. After Sarah and Julian left, the conversation between Lisa and Tom grew more intimate, fueled by the alcohol and the dwindling crowd around them.
"Looks like it's just us," Lisa said.
Tom shifted in his seat and looked straight ahead into Lisa's eyes, doing his best not to glance slightly lower at those gorgeous creamy jugs directly in his line of sight.
"Yeah," he said. "For now...I gotta get going soon."
Lisa frowned and played with her wedding ring. "No way, Tom. It's barely nine. Do you know how hard it was to get a sitter? I paid until midnight and I plan on getting my money's worth."
She then grabbed her glass and chugged it swiftly all down. "Okay now then, baby boy, go get me another vodka soda."
Something about Lisa calling him baby boy electrified Tom. He smiled and looked at his watch. This was going to be better than his previously planned masturbation then video game session.
"If you insist, ma'am."
Tom returned quickly with two vodka sodas in tow, plus two shots of tequila.
"Oh, what's all this?!" Lisa said smiling.
"Let's make this a night then," Tom said.
Lisa grabbed the shot off the table and raised it up
"To Prometheus Medical Technologies!" Lisa said, playfully exaggerating her sincerity. "Thank you so so much for the contract and for paying for these drinks."
"And my rent for the next three months," Tom added.
"Yes, and for sweet baby Tom's rent!"
"Cheers!"
They knocked them back and smiled at each other.
"So, how'd you end up here?" Tom asked.
"What do you mean?" Lisa said, genuinely confused.
"I don't know...seems like your talents are wasted at our outfit."
"Flattery will get you everywhere, my dear baby boy," Lisa said as she leaned over and playfully tussled Tom's hair. Tom used the opportunity to stare deep into Lisa's cleavage. Yes, D cups at least. And specked with freckles, just like her face.
"Okay, so here's the Lisa Henderson story: I went to college to become a nurse, believe it or not. I worked in maternity. Loved it. And that's where I met Dr. Henderson, AKA Carl, AKA the love of my life. I worked as a nurse for five years and was dating Carl sort of in secret. Then I got pregnant, and the gig was up. We got married, and my Carl wanted me to stay home with Tyler, but I got bored, so once he turned two, I started looking for jobs that would let me work from home at least some of the time...this place was hiring, and lo and behold, I'm sort of good at it. Haha who would have thought this dumb ass sorority bimbo would be good at sales?!"
"It's a mystery for the ages, but it can't be argued. You're good."
Lisa leaned in yet again, fully aware of what she was doing. "What do you think it is, baby boy? Why am I so good at this job?"
This time Tom didn't try to hide his obvious staring.
"Excellent people skills," he said, eyes firmly planted right between her tits.
Lisa chuckled softly. "You know, you're quite the charmer, Tom. And very observant." She took another sip of her drink, her eyes never leaving his.
"But tell me about you. Fresh out of college, and already making bank. How does that feel?"
Tom grinned, feeling more confident. "It's a rush, honestly. I mean, I never thought I'd be here, making deals, celebrating wins. It's a different world from college."
Lisa nodded, her eyes twinkling. "And what did you study in college, Mr. Flint?"
"Communications," Tom replied. "Seemed like the best way to keep my options open.
"And now look at you. Lucky lucky duck." Lisa said slyly and finished her drink. She slid her chair to be closer to Tom. "One more round, baby boy," Lisa said, her left hand caressing his back. "Think of it as your "looking" fee."
Tom, clearly feeling emboldened by the drinks, retorted, "How much to touch?"
Lisa laughed. "Keep dreaming, kid. Plus, don't forget," she held up her left hand, showing her shining ring.
Tom returned from the bar with the same thing as before: two vodka sodas and two shots.
"You're such a puppy dog," Lisa said, snatching the drinks. "Bet your girlfriend loves that about you."
"Actually, I'm single."
"No kidding?! Must be nice."
"It has its perks. Like hanging out with a married woman."
Lisa quickly downed her shot. "It's just drinks, baby boy. Don't get any ideas."
"Of course."
"Tell me, Tom," Lisa said, leaning in close enough that he could smell the sweet mix of her perfume and the alcohol on her breath. "What's a handsome, young guy like you doing single?"
Tom shrugged, trying to appear nonchalant. "I guess I haven't found the right person yet. Or maybe I'm just too focused on work."
Lisa raised an eyebrow, her lips curling into a sly smile. "Or maybe you just haven't met the right woman who can handle you."
Tom's pulse quickened, his gaze locked onto her lips. "Maybe," he said, "but truthfully there's not much to handle. I'm boring."
Lisa's hand moved to rest on his thigh, her fingers lightly tracing patterns. "You know, Tom, you're quite a catch. Any woman would be lucky to have you."
"And Mr. Henderson is lucky to have you."
Lisa chuckled.
"Doctor Henderson," Lisa corrected. "He'll be sure to remind you. It's doctor."
"Ah, I see. My mistake. You know, we've worked together for almost a year and I've never seen him once."
"He's a busy man. When we were both at the hospital together, it was easier to see each other. Now... now it's like, we barely get a chance to spend time together." Tom could see Lisa getting somewhat serious before she broke into an exaggerated voice. "A woman has needs, Tom!"
Tom laughed. "Yeah, I'll bet. Paging Doctor Henderson; am I right?"
"God, you have no idea."
"Oh? Educate me then."
Lisa took this as a challenge. "Alright, baby boy. You're about to get more than you bargained for." Lisa swilled her drink, now just a glass of empty ice cubes. "But first... the fee."
Tom sighed teasingly and got up to the bar to return with another vodka soda set in tow. "Thank you, love."
Something about Lisa calling him "love" almost made him jizz then and there.
"Okay, so where was I? Oh yes, drunk Lisa was going to tell you all the problems in her marriage."
"Uh huh."
"Well, it's really just one. The guy doesn't fuck me anymore. Can you believe it?"
"Absolutely criminal!"
Lisa sighed, her frustration bubbling to the surface. "It's just... my husband is always working late. I feel like I'm invisible to him sometimes. And being a mom... it's wonderful, but it's hard. I miss feeling desired, feeling alive."
Tom nodded, his gaze sympathetic. "That sounds really tough. I had no idea you were feeling this way."
"You wouldn't believe it, Tom," she said. "I used to be quite the wild party girl in college."
"I guess I can see it. What sort of shenanigans did you get up to?" Tom asked, leaning in and intrigued.
"Well let's see...one night me and my sorority sisters went streaking across the quad. We were wearing masks of Disney characters. I was Grumpy."
Tom imagined the sight for a moment.
"I guess that's sort of hot...but not that outrageous."
"Oh, the communications major wants the good stuff."
"Yeah. Give me the stuff in the vault"
"For the spank bank?"
"More or less."
"I was free-spirited, always up for anything... honestly, I was a bit of a slut," she admitted with a laugh. "I used to let guys do all sorts of things to me. It was thrilling."
Tom's curiosity was piqued. "Really? I can't imagine you like that," he said, a hint of teasing in his voice.
"Oh, you name it. But my absolute favorite thing in the world," Lisa said, slurring and leaning in close, "was getting fucked in the ass." She pulled back and closed her eyes. "God, how I loved it."
What. The. Hell. What the hell was going on? Tom felt his face flush, and his cock was now as rigid as iron.
"Oh. This is so sweet. Look at you. Want me to stop?" Lisa teased.
"N-no." Tom spat out. "Tell me more."
Lisa was clearly getting a kick out of this. "Well, the first time I got fucked in the ass--this is a hot story, prepare yourself--the first time was freshman year, and it was with a senior named Greg. It was me and my sorority sister Melanie. Melanie was a pro, pretty sure she got a huge head start if you know what I mean. She was there to soothe me and talk me through it. God, I still remember her kissing me as Greg shot his hot load all up into my big...round... freshman butt," Lisa said, playing up the sensuality of the scene for Tom's benefit.
Finally, Tom said, "I bet the good doctor Henderson loves that story."
Lisa burst out laughing. "You are so cute. And actually... get this, Tom. The guy is as boring in the sack as they come. Not once has he ever taken me up on my offer of anal. In fact, ever since we had Tyler, he won't even touch me at all. And he works nights now, so we just don't see each other. I wasn't joking when I said I had needs, Tom!"
"Wow. I had no idea that was going on."
Tom shifted uncomfortably, feeling a mix of empathy and arousal. "That sounds really rough, Lisa. I'm sorry you're going through that."
Lisa looked at him, her expression softening.
"Thanks, Tom. It's nice to have someone to talk to about it." She sighed and took a deep breath. "But enough about my sob story. Let's focus on having a good time tonight."
Tom nodded, grateful for the change in topic. "Agreed. So, what's next on our agenda?"
Tom looked at his watch. It was nearing 11:00. "Looks like time is almost up." For the first time in a while, Tom looked at the scene around him. The bar was dying down--it was a Thursday after all, and save for a few older barflies and the bartender, it was mostly just Lisa and Tom left.
"I'll close out."
"Yeah..." Lisa said, disappointed, "okay. I'll call an Uber. I just need to use the little girl's room."
Lisa got up and walked to the restroom. Her round plump ass swayed as she walked, until she stopped and looked at Tom with a wink before she continued on to the restroom hallway. Tom stood up and got in line. He waited for a few seconds before gathering his nerve and getting out of line, making his way to the restroom hallway. He made sure no one saw him before entering the door that Lisa had gone in.
Tom looked around the bar, noticing how it had quieted down. It was nearing 11:00 PM, and the place was almost empty. He glanced towards the restroom hallway where Lisa had gone, her round, plump ass swaying as she walked. She had stopped and looked back at him with a wink before disappearing into the hallway. Tom gathered his nerve, got up, and made his way to the restroom hallway, making sure no one saw him before entering the door Lisa had gone through.
There, waiting for him, was Lisa, leaning casually against the sink, her curvaceous figure highlighted by the dim restroom lighting. She stared at him seductively, her green eyes gleaming with mischief.
"Thank god you know how to take a hint," she said, wrapping her arms around his neck and pulling him close.
Tom felt his heart pounding in his chest as Lisa pressed her body against his. Her breath was warm on his neck as she whispered, "I've been wanting this all night."
Tom's hands moved to her waist, pulling her closer. "Me too," he admitted, his voice husky.
Lisa's hands roamed over his back before she reached down to unzip his pants. "Let's make this quick, baby boy," she said, her voice dripping with desire. "I don't want to get caught."
Tom nodded, his breath shallow. Lisa turned around, lifting her tight, form-fitting skirt to reveal her bare, full-figured ass. Tom couldn't believe his eyes. Her pale cheeks and thick round hips beckoned to him. Lisa turned her head sharply.
"Lock the door, dummy."
"Oh shit." Tom twisted the lock.
"Tom...I want you to fuck my ass."
Lisa leaned over the sink and, with both hands, reached around and spread open her cheeks, giving Tom a front-row seat to her cute pink rosebud.
"I've never done that before..."
Lisa couldn't help but laugh. "It's going to be great for you, but I'll guide you. Spit on my booty hole, baby boy."
Tom looked down and with his best aim, let some spit dribble out of his mouth and onto her buttcrack, where it slid down into her asshole. "It's been so long," Lisa managed to say. "You're gonna need more. Spit on your dick."
Tom did as he was told and spit in his palm, rubbing it onto his cock before guiding it to her tight exit hole. "It might give some push at first but then it is gonna feel like my ass is swallowing your dick."
Lisa moaned softly as he pushed into her, her hands bracing against the sink. "Oh, fuck yes," she gasped. "Just like that."
Tom stood still, unsure of what to do. "Are you okay?" he asked. "Does it hurt?"
Lisa smiled and shook her head. "This isn't my first rodeo. Hurry up and fuck my ass."
Tom's thrusts were slow and deliberate at first, savoring the sensation of her tightness around him. The restroom was dimly lit, the soft glow from the overhead light casting shadows that danced around the small space. The smell of her perfume mingled with the scent of their arousal, creating an intoxicating atmosphere.
Soon, the urgency took over, and Tom began to move faster, their bodies slapping together in the confined space. He slid in and out of her rectum with ease. Lisa's eyes were closed, her red hair swaying with each thrust. She repositioned herself so that she could hold herself up with one arm and play with her breasts with the other. She slid her hand under her shirt and began to squeeze her own tits, her moans barely audible as she bit her lip to keep quiet.
"Oh god, oh fuck. Oooh fuck. Oh god damn. Oh god, oh god, oh god it feels so good," she whispered, her voice filled with raw desire.
She swiftly removed her hand from her breast and began to play with her clit, her movements quick and desperate. "I'm your fucking whore. I'm your slut. I'm letting you fuck my ass. You can do whatever you want to me."
Tom was not used to having a partner speak like that, but it fueled his arousal even more. "I'm your filthy slut. I want you to come in my ass. Come in my ass, baby boy. Fill my ass with cum."
The sound of their breathing mingled with the soft music playing in the bar outside, creating a heady mix of sensations. Lisa's moans grew louder, her pleasure evident. "Harder, Tom. Fill my fucking ass up, baby boy," she urged, her voice breathy.
The sensation of Lisa's tight ass around his cock was too much and Tom felt his own release building, his control slipping. He reached around to play with her clit, intensifying her pleasure. "God, Lisa, you feel amazing," he groaned.
Lisa's body responded eagerly, her moans turning into cries of pleasure. "Yes, baby boy. Just like that. Make me come."
With a final thrust, Tom climaxed, his release filling her most intimate area with his cum. Lisa shuddered with pleasure, the sensation overwhelming her. It had been years since she had been fucked in the ass by something other than her dildo and she missed it dearly. They stayed like that for a moment, catching their breath, the reality of what they'd just done slowly sinking in.
Tom pulled out gently, helping Lisa straighten her skirt. "Are you okay?" he asked, concern in his eyes.
Lisa nodded, a satisfied smile on her lips. "Better than okay. Thank you. Now go make sure no one saw us while I shit out your cum."
Tom, still reeling from the intensity of their encounter, adjusted his clothes and took a deep breath. He unlocked the door and carefully stepped out into the hallway, making sure no one was around. The bar was quiet, with only a few patrons remaining, none of whom seemed to have noticed their absence.
Lisa emerged from the restroom a few minutes later, looking as composed as ever. She walked up to Tom, a playful smile on her lips. "All clear?" she asked.
Tom nodded, his heart still racing. "Yeah, I think we're good."
Lisa gave him a knowing look. "Thanks for a memorable night, Tom. I really needed that."
Tom smiled, a mix of pride and disbelief. "Anytime, Lisa. I mean it."
Lisa winked at him before heading towards the exit. "See you at work, baby boy. And remember, this stays between us."
Tom watched her leave, a sense of exhilaration washing over him. As he walked out of the bar, he felt a strange mix of emotions--satisfaction, excitement, and a hint of apprehension about what the future might hold.
Tom decided to take that Friday off to nurse his hangover and enjoy a long weekend. Monday at alphaData had a different feel. Tom walked into the office, feeling more confident than ever before. The buzz of the sales floor was the same, but Tom felt like he was walking on air. He glanced around, looking for Lisa, but she wasn't at her desk yet.
"Morning, Flint," Sarah called out from her cubicle, a sly smile on her face. "How was your weekend?"
Tom shrugged, trying to play it cool. "Pretty good. How about yours?"
Sarah raised an eyebrow. "Pretty good, huh? Well, I guess we'll see if that pretty good attitude translates to some pretty good sales numbers today."
Tom laughed. "I'll do my best."
Just then, Lisa walked in, looking as poised and professional as always. Her long, wavy ginger hair framed her face perfectly, and her green eyes sparkled with a hint of mischief as she glanced in Tom's direction. She wore a fitted dress that accentuated her curvaceous figure, and Tom couldn't help but feel a pang of desire as he watched her move through the office.
"Morning, Lisa," Tom said, doing his best to sound casual.
"Morning, Tom," Lisa replied, her voice smooth and confident. She gave him a quick, knowing smile before heading to her desk.
The day went by in a blur of meetings, calls, and emails. Tom found it hard to concentrate, his mind frequently drifting back to the events of the weekend. Every time he saw Lisa, he felt a jolt of excitement and a flood of memories from their night together.
"I had so much fun Lisa."
Lisa smiled, a hint of sadness in her eyes. "I had a great time too, Tom. But I want to be clear--what happened between us last weekend was a one-time thing. We both have to be professional about this."
Tom nodded, understanding but still hopeful. "I get it, Lisa. But maybe, just maybe, if we land another big sale... we can celebrate again?"
Lisa chuckled softly, leaning in close to whisper in his ear, "My ass still hurts from the last celebration, but maybe." She pulled back, her eyes twinkling with mischief and something more.
Tom grinned, feeling a spark of hope. "I'll be sure to keep working hard, then."
Lisa gave him a warm smile and squeezed his hand one last time. "Don't get ahead of yourself baby boy."
In the midst of the lively celebration, Tom found himself unable to concentrate on the conversation, his gaze frequently drawn to Lisa's ample figure.
As the night wore on and the crowd dwindled, Lisa suggested, "Why don't we take advantage of the empty bar and this round on the house, and continue our celebration?"
