*Skip to the \*\*\* if you just want the good stuff. Names are changed for anonymity and some dialogue is altered for dramatic effect.*
* *
I started my first day at Helios Supply at 8:00 am on a Monday. By 9:00 am, I was introduced to the other member of my team, Jenny. By 10:00 am, I was back on Indeed contemplating how long I could last.
In truth, the job was great. Great pay, relaxed culture, good benefits, and a kind and understanding boss. The one problem was Jenny. She was critical, demanding, impatient, and flat out rude sometimes. And I had to work with her Every. Single. Day. Because our team was originally just her and our boss Gloria until I was hired on and Gloria was promoted.
Throughout the first week, I bided my tongue and accepted Jenny’s criticisms. By the end of the second week, I had slowly begun to advocate for my own opinions while still taking her feedback. By the end of the third week, I was ready to explode.
It was the first day of the fourth week that I stormed into Gloria’s office.
“Morning, Cal! How are- is everything okay?” She had noticed my expression midway through her greeting.
I closed the door gently, sitting at the chair opposite her own with her desk between us. Leaning in, I quietly began my complaints. “Gloria, I want to start off by saying I love this job and I think you are a fantastic boss.” I looked around the big glass window to my left and gestured my head towards Jenny’s desk. “But Jenny is… she’s driving me crazy.”
Gloria furrowed her brow. “Oh dear… I worried this might happen.”
I continued. “Her comments are incessant, and while she is the expert, she doesn’t know how to actually communicate what she wants on these projects. I know I’m new, and I appreciate her feedback, but the way she gives it is like nails on a chalkboard to me.”
Gloria tapped her desk and nodded her head. “Can I be frank with you, Cal?”
I nodded, fearing what she might say.
“If you don’t know, Jenny has been here longer than I have. Before our team was a team, it was just Jenny, who started here when she was 18 when this company was barely more than a startup. And yet, when they created my position and looked to expand the team, they didn’t even interview her. They just offered me the job, so I took it, and now I have to manage the person that trained me and taught me everything I know.”
Gloria leaned in.
“You’re a smart kid. I think you can probably figure out why.”
Helios was a small, family-owned company that had exploded into a national conglomerate in recent years, but the original family still owned it. In short, it was a boys club. All of the owners and VPs were members of the family or married to members of the family, and most of them were older, traditionalist men.
Gloria was soft-spoken, feminine, slender, and dainty. Jenny was blunt, abrasive, and bordered on tomboy-ish. It was messed up, but I wasn’t surprised why the ownership group favored the former. A wave of guilt washed over me as I thought about Jenny’s position, but I shook it off to strengthen my resolve.
“Okay, I get your point, but… it doesn’t change the fact that working with Jenny is insufferable.”
Gloria sighed. “I understand your frustration. But…” Gloria looked away and shrugged. “I’m her manager in title alone. In case you haven’t noticed, she’s quite stubborn, and she’s fully aware of her value to this company. There’s nothing I can do.”
My heart sank, the realization that there was no end to the suffering crushing my spirits.
Gloria reached out a reassuring hand and placed it on my arm. “She just needs to get used to you, to trust you. She just needs…time.”
I slumped my shoulders, looking down at the desk. “Right. Time.”
Sensing my discomfort, Gloria offered a new suggestion. “Maybe she just needs to get to know you more. What if the three of us went out for a drink after work? My treat?”
Every day, I was staring at the clock waiting for the minute I could leave and get away from Jenny. And now, the proposed solution to my problem was more Jenny. When I looked into Gloria’s eyes to refuse her offer, I could tell she was being genuine. She wanted me on the team and was honestly trying to find a way to help.
I let out a long sigh. “I suppose it’s worth a try.”
Gloria grinned and clapped her hands together.
“Oh, and one other thing. Let’s pretend it was your idea.”
\-
As I parked my car on the side street next to the bar we agreed to meet at, I looked down at the time.
*8:01. Great, now she’s going to chew me out for being late.*
Walking around the building, I sent a text to Gloria.
“Just parked. Where are you sitting?”
A few seconds later, a reply.
“Home. Sorry, Cal. If I told you I wasn’t coming, you couldn’t have agreed to it.”
I stopped in my tracks, staring at my phone in shock. Then, another message with fifty dollars of Apple Cash attached.
“Still my treat though! Have fun!”
For a moment, I considered sending her money back with my resignation, but a few paces back and forth calmed me down. But yet, the Herculean task of spending an evening with the bane of my existence still lied before me. After some hesitation, I steeled my nerves and walked in the bar.
It was dark inside besides the lights of pinball machines, arcade cabinets, and other retro games surrounding the walls of the building. In the middle was the bar, and sitting on a stool sipping a drink by herself was Jenny, though she looked…different. At work, she wore her hair straight and down across her shoulders. Her usual garb was slacks, a simple shirt, and a blazer. The woman sitting at the bar was definitely Jenny, but a totally different creature. A messy bun held up by a clip, a cropped washed-out band t-shirt, short jean shorts, and the biggest surprise of all: glasses. Big rectangular frames that shaped her face surprisingly well. As cliche as it sounds, I was suddenly realizing how cute Jenny was.
I waved awkwardly and walked up to her. Before I could say anything, she started talking.
“It’s alright, Gloria texted me. I’ll just finish my drink and go home.”
An hour ago, that would have been music to my ears. Now, not so much. “Wait, why?”
Jenny rolled her eyes and laughed, putting her drink down on the bar. “Look, I’ve known Gloria for years. I know she put you up to this so it would look like your idea. Her idea of ‘team building’ or something.” She said “team building” sarcastically and with air quotes. “Because I’m nice, we can say we had a great time with lots of laughs, blah blah blah, and we’re best friends now. Then you can go home and spend your night doing… whatever you do.” She tilted her head and put on a fake smile. “Deal?”
I looked into her eyes as she waited for my response, and I felt a twinge of sadness from them. Like her whole premise was based on the obvious assumption that I didn’t want to be there. Suddenly, I had the desire to prove her wrong.
I shrugged. “Hear me out. We stay and spend her money, and it’s a win-win. Either we have a great time or we hate each other so much by the end that she can’t stand working with both of us.”
That was the first time I heard Jenny laugh. It was loud and obnoxious, but in an endearing way. Then she looked at me suspiciously. “So to be clear, you want to stay?”
“Is that so hard to believe?” I replied.
She looked away, gazing off in the distance. “Kinda. I’m not the most social person in the world, so I don’t have people lining up to spend time with me.”
I chuckled. “Nooo, really?” I said sarcastically.”
Her expression turned dark and stern. “The fuck is that supposed to mean?”
I froze in fear as she stared daggers into me. My heart and stomach fell into my ass as I stammered out a response, trying to damage correct. “Oh god, I- I didn’t mean to- I shouldn’t have-“
As I fumbled out my words, her face eventually twisted and broke into an uncontrollable smile, and she broke out laughing even harder than before. I stood and watched, blushing as I realized what had happened.
“That’s fucked up.”
She wiped a tear from her eye, holding her stomach to control the laughter. “I’m sorry, I’m sorry, but you should have seen your face. Fucking incredible.”
As the fear ran out of my system, I couldn’t help but smile at the well-executed joke.
“Fuck you. Let’s play some games.”
\-
As the night progressed, I learned that Jenny's snide comments were a lot more fun when I had the opportunity to shoot back. Over a couple of drinks, we played games like ski ball, foosball, Time Crisis, and bubble hockey. Jenny was a grade-A shit-talker, and the more I pushed back, the harder she pushed. I never would have expected it, but it was a fantastic time.
And then, we came across a Street Fighter II cabinet, and things changed quickly. I pointed at it with my thumb. "You want to catch these hands?"
Jenny smiled wickedly. "I don't know... I'm pretty good at fighting games."
My hands went up in faux fear. "Oh nooo, I'm so scared..."
Her hands reached into her pocket and pulled out a few tokens. "Don't say I didn't warn you."
She picked Ryu and I picked Chun Li, and then the game began. Immediately I noticed a difference in her demeanor. She was more focused, less care-free. Her joystick movements and buttons were intentional, but I could also tell she wasn't totally comfortable. When she made mistakes, she seemed frustrated. All the same, she won the first game pretty easily, looking over to me with a smirk.
"Hey, I'm just getting warmed up."
The second game ended similarly to the first, but she still made occasional mistakes that seemed to get to her. But on the third game, I found a move to spam that seemed to exploit some of the movement mistakes she was making. It came down to the final hit, with dumb luck, I was able to take a game.
"Haha! Gotcha!"
This time, Jenny did not deflect my jab with another insult. She looked at me, fuming.
"Fuck this. We're going to my place, NOW. I can't play on these shitty arcade cabinets.”
My teasing expression turned to confused. Without giving me a chance to protest, she stormed off towards the bar to settle the tab.
\*\*\*\*\*
Jenny had a modest but homely house not too far from the bar in which she lived alone. As I parked in her driveway, my nerves from earlier started to return. Our behavior at the bar had bordered on flirting, and now I was back at her place.
*Get your head out of the gutter, dumbass. She just wants to beat your ass at Street Fighter.*
The inside was clean but a little cluttered. She led me to her living room where a large couch sat a few feet away from an impressive TV. The entertainment center below the TV had game systems and controllers all around. On the coffee table in between, I noticed a specific kind of controller.
“Damn, you have a fight stick?”
Jenny shrugged. “I used to go to tournaments a lot. Never won any, but I could win a few matches.”
Immediately, I knew I had no chance to beat her once she was playing at full strength, but I couldn’t let her know that. I sat down on the couch, grabbing a nearby PS5 controller. “Ready when you are.”
She smirked, walking away from the TV towards the kitchen behind us. “Water, beer?” She offered.
“I’ll take a beer,” I called back, my eyes naturally wandering around the room. When my gaze reached the other end of the couch, a small object caught my eye. After a moment of shock and embarrassment, I thought back to Jenny’s little prank at the bar and realized I may have gotten my ticket to payback. I subtly grabbed the object and stuffed it behind me on the couch.
A few seconds later, Jenny returned from the kitchen with two cold bottles of beer and placed one in front of me on the coffee table. “I’m sorry for what I’m about to do to you.” she said solemnly.
She wasn’t wrong. Now that she was on her optimal setup, I didn’t stand a chance. The first round I barely got a hit in, and the second I didn’t get one in at all. By the third ass-whooping, I figured it was time to set my plan in motion. As we were playing the fourth game, I started moving my body back and forth, I tried to seem natural as I shifted my weight against the object behind me, trying to activate it. Finally, a muffled whirring let me know I had succeeded.
“Do you hear that?” I said, trying to sound confused.
“Hear wha-“ And suddenly, she was conscious of the sound. It did not take long for her to realize what it was, as her expression went blank and her face went white. She paused the game and looked over at me.
“Oh wait, I think it’s behind me.”
I started to reach my hand behind the pillow where I had stored the object.
“Wait don’t!” Jenny started to say, but it was too late. My hand grabbed the object and pulled it into the light, revealing a small, purple vibrator actively whirring. She stared at it in my hand, mouth open in horror. After a few seconds, Jenny broke the silence. “Umm… sorry about… that-“
My face warped into a grin. “Told you I’d get you back.” For a moment, I worried I had gone too far as she continued to stare at me in stunned silence. Luckily, she removed my suspicions by breaking a smile and playfully pushing me into the couch, following up with a series of punches to my arms. “You. Fucking. Ass. Hole!” She said with every punch.
Then, she reached for the vibrator still in my hand, and I decided to torment her further. I closed my fist and reached it away from her, playing a game of keep-away. “On the couch, Jenny? I guess those are the perks of living alone.”
She reached for it, but I held it away further. Suddenly, I was aware of how close together we were on the couch. “Give it back, Cal.”
I continued my joke. “Or is this how you practice Street Fighter? Let this thing rip while you’re playing to improve your focus?”
Jenny reached for my hand again, but failed to reach it. She sat back in a huff, thought for a second, then tried a new strategy. Reclining her back on the couch, she spread her legs and shoved one of her hands down the front of her shorts. The other went to her chest, rubbing the outside of her shirt.
“Actually, it looks something like this. Mmmm” she said, fake lust in her voice, adding a pretend moan at the end. The performance was enough to distract me though, as my attention solely went to her. Once she noticed her trick had worked, she reached for my hand and stole back her toy.
“Too easy.” She said with a proud smirk. She continued, looking at the toy. “The sad part is, even if I was using this thing while playing, I could still probably beat you.”
I was still slightly aroused from her fondling herself a moment ago, so I said something unexpected. “Oh yeah? Prove it.”
“What?” Jenny said, losing some of her confidence.
Realizing what I had said, I almost back-pedaled out of the interaction. But curiosity urged me to press on. “Prove it. Turn it on and use it during the next match, and we’ll see how good you really are.”
As she studied me in silence for a moment, I was convinced she was going to throw me out of her house and hate me forever, and that my days at work would be even more miserable than before. To my surprise, she met my challenge instead.
“Fine. Easy peasy.”
I watched in stunned silence as she queued up the next match, unbuttoned her shorts, and slid the vibrator down the front of them, turning it on. She let out a sharp exhale as the toy began to move between her legs. Before I knew it, the match was starting, and somehow I was more distracted.
My competitive spirit and my lusty curiosity battled inside me, but I found the drive to let my competitive side win out. She started out playing just as strong, but from the corner of my eye, I saw her shift her legs and heard a small muffled moan escape from her closed mouth. I pressed the advantage and could tell her focus was slipping as her defensive game had fallen off significantly. Even so, she still took the first round, though in closer fashion than before.
“Told you.” She said, shakily.
I shrugged. “Hey I was pretty close. Surely that’s not the highest setting that thing has.”
Wordlessly, Jenny contemplated for a moment before reaching back into her shorts. The whirring of the toy grew louder, and she let out a soft “oh fuck.” The sights and sounds had increased my arousal, leading to a stirring beneath my jeans.
Jenny started the game again, and this time I knew I had a chance. Her muffled moans were frequent. She struggled to string her moves together and almost stopped playing defense altogether. My inexperience still made the round close, but I was able to win it.
“Yes!” I pumped my fist. “In your face-“ As I turned to her to rub it in, I was met with a beautiful and unexpected scene. Jenny had leaned back and spread her legs, her hand now down the front of her shorts, holding the vibrator in place for extra sensation. Her thick, pale thighs were moist with either sweat or the wetness from between her legs, and I watched her silently in awe.
After half a minute or so, Jenny seemed to snap back to her senses, opening her eyes and meeting mine. She quickly sat up, removing her hand and the toy from between her legs. The toy went silent as she tapped the button to turn it off. “Oh my fucking god, I am so sorry. I don’t know what came over me.”
I waved it off with my hand. “Don’t fret it. I’m the one that egged you on to do it in the first place.”
She chuckled. “More like edged me on.”
We both laughed. “Good point.” I said.
After a few more seconds of silence, I took a big swig of my beer, finishing it off. “Well, I guess I should get going. Since I’m sure you’d like to, uh, finish.”
“Right, yeah it is late.” I saw that sad tint in her eye again.
“Mind if I use your bathroom real quick before I go?” I stood up without thinking, and suddenly the imprint against my jeans was extremely visible and right in front of Jenny. I saw her eyes dart down to it for a moment before looking back at me.
“Not at all. Down the hall to the left.”
I spun around as quick as I could, walking in the specified direction. When I closed the bathroom door behind me, I looked down at the bulge against my pants.
*Not like I can pee like this anyway.*
I maintained the illusion by standing in there for 30 seconds or so before flushing the toilet and washing my hands. When I came back out into the hallway, I saw Jenny leaning against the back of the couch, waiting for me. Her jean shorts were still unbuttoned, showing a hint of a black pair of underwear beneath.
I scratched the back of my head, trying not to look. “Well, thanks for the beer and for the games. I’ll see you tomorrow.”
She opened her mouth to say something, but then chuckled and shook her head.
“What?” I asked curiously.
“Nothing, I- oh nothing.” She said with a sigh.
“Come on, spit it out.” I was trying not to sound too eager.
Jenny looked back at me. “Well, I was going to ask you to stay and make me cum. But you probably couldn’t do it anyway, so it’s probably best you just leave.”
Blood pulsed through my brain and back into my cock. Her words rang in my ears. I met her challenge.
“You want to bet?”
She laughed. “Someone’s confident.”
“If I don’t, I’ll never complain about doing your reports again.”
She nodded, thinking. “And if you do?”
I shrugged. “Then you return the favor.”
After another moment of thought, she gave her answer by letting her shorts fall to the floor, revealing a skimpy black thong underneath. She turned and walked around the couch, her ass swaying back and forth with each step. I followed behind her.
Once she took her seat on the couch, she spread her legs, inviting me in. I got on my knees in front of her, peeling the thong off with my fingers. The folds underneath glistened with wetness as I admired her, leaning in and kissing her between her legs. My kisses turned to slow movements of my tongue up and down her lips, and she responded with moans louder and more pronounced than the muffled ones from earlier. Next, I slid a single finger inside of her, exploring her insides. Her wetness made the movements effortless, so I added a second finger and sped up my movements, bringing my tongue to her clit. The combined stimuli made her arch her back, and her moans turned to involuntarily grunts and gasps.
After a couple minutes, I knew her climax was close. I stuck my fingers even deeper inside, curving them onto her G-spot. “Fuck, fuck, fuck, fuck, fuck!” She yelled, and suddenly my face was bombarded with a stream of liquid. Once her orgasm was complete, she slumped back into the couch. “Fuck that was good.”
I sat back, catching my own breath and wiping my face on my shirt. “I can tell.”
She giggled. I looked up at her, watching her chest rise and fall from her deep breaths. “Well, deals a deal.” I stood up over her.
She looked up at me, her eyes wide. With a finger on her chin, she pondered for a moment. “Oh, you think it’s your turn now?”
I nodded.
“Make me.” She said, in a soft voice.
“What?”
“Make. Me.” She repeated, playfully this time.
*I see. She wants to play the little brat.*
I looked at her, stern-faced. “My pants. Off. Now.” My tone was low and serious.
Her eyes widened even more, biting her lip. She shimmied off of the couch onto her knees, undoing my belt and pulling my pants down. My cock pitched a circus-like tent within my boxers. Jenny looked up at me and waited.
“My boxers too.”
She obeyed. With my dick now free, she looked at it hungrily.
“You want to suck it, don’t you?”
She nodded.
I gently grabbed her face and positioned it up to me. “Answer me properly when I ask you a question.”
“Yes, daddy.”
“Good girl.” She smiled and giggled at that. “Then suck it.”
With one hand on my shaft, she took me fully into her mouth. She started slow, wrapping her tongue around my tip, letting the moisture of her mouth cover my cock. The magnificent feeling hypnotized me, and I grunted and put my hand on the back of her head. “Fuck, you’re good at this.”
My encouragement motivated her further. Jenny took her hand off and focused on taking me as deep into her throat as possible, powering through some light gags. Her big eyes looked up to me while my cock was swallowed by her mouth and throat.
*Fuck, I can’t take it anymore.*
Pulling my dick out of her mouth, I helped her to her feet. With a quick pull, I removed her cropped t-shirt over her head, revealing a lacy black bra underneath. Her tits were so much bigger than I had ever noticed in her work clothes, and I was lost in them. She smiled at me as I reached around and unhooked her bra, letting her beautiful breasts fall free.
“Holy fuck.” I grunted.
She giggled. “You like them, daddy?”
I answered her with a sloppy, passionate kiss. My tongue explored her mouth, and hers mine. I moved my kisses downward across her chest and down to her left nipple. They were red and swollen and felt heavenly in my mouth.
Jenny moaned in pleasure, running her hands through my hair. Once both of her nipples were glistening with moisture, I brought my face back to hers. “Where are your condoms?”
She tilted her head innocently. “What for?”
“So I can fuck you senseless,” I said, caressing her face.
She smiled at me before bending over the front of the couch, using one of her hands to spread her shapely ass. “Then fuck me.”
Logic and reason had long left me. I walked forward, positioning myself behind her. Using my hand, I placed my cock against her pussy and slid it inside effortlessly. She was warm, tight, and magnificent.
“Ohhhh fuck.” She moaned. “Ruin me, daddy.”
After a few slow thrusts to warm us up, I started vigorously thrusting my hips into her. Her moans turned animalistic, her pussy gripping onto me. I used one hand to grab her bun and pull it back, eliciting a surprised high pitched moan from Jenny. My eyes fixed on her asshole, and my temptation gave in, teasing it with my thumb.
“Oh- my- god- Cal- fuuuck…” I forced my thumb inside, feeling the extremely tight, unexplored hole.
It didn’t take long for me to reach the edge. “Jenny, I’m gonna cum.”
“Mmm yes, cum in me daddy. Please? Please cum in me?”
I knew it was a terrible idea, but her pleas were too much to refuse. With a few more powerful thrusts, I let out a loud “fuuuck!” And pumped a massive load of my seed inside of her. She moaned softly, feeling my dick pulse against her pussy in a beautiful, forbidden bliss. Once I was finished, I slowly took my dick out of her and admired my handiwork. Our fluids had mixed into a solution of lust that began to slowly drip onto Jenny’s floor.
We both collapsed on the couch, breathing deeply, blood returning to our brains. As my senses returned to me, my anxiety spiked to even higher levels than when I had first walked into the bar.
*What the fuck happens now?*
Just as I was about to awkwardly stumble through the impossible conversation, she beat me to it. But instead, she rolled over and gave me a long, deep kiss.
“Stay? Please?”
Finally, the words that her eyes had been screaming all night. I answered her with another kiss.