Staying Late With My Boss

It was nearing the end of the day and I was looking forward to being away from my cubicle for the weekend. I work on the 11th floor of a skyscraper in downtown Phoenix Arizona for an architecture firm. I graduated college a little over a year ago and was thrilled to land this job, but I was still ready to leave for the day. Not that I had any big plans for the weekend, most likely I'd order pizza and play video games all evening.

I was getting my stuff together in my messenger bag, and was about to shut down my computer when my boss came into the cubicle pool just outside her office. Allison is a decent and fair boss, and everyone liked her. She's probably mid-forties or so, white, brunette and sorta pear-shaped. She had a large butt and wide hips, but her boobs were probably only Bs or possibly Cs. Allison rarely wore makeup and generally dressed professionally in a plane way. Pant suits, ankle length skirts and dresses, maybe capri pants on occasion. Today she was wearing a calf-length gray dress that didn't show any cleavage at all. Reasonably attractive in an average way.

She moved her glasses to the top of her head and said "I've got some bad news, team. Our director just called and we have a project that needs to be finished tonight for a client that could be huge for the company. Which could mean bonuses for us if it goes well. I will be staying late tonight to get it finished. Can I get a volunteer to stay and help? You'll get time and a half."

No one volunteered. Most of the people I worked with had families or significant others to get home to. I didn't even have a goldfish waiting for me. I'd been single for over 8 months.

Allison got a pained look on her face and said "please? I know it sucks, but if I don't get a volunteer I'll have to draw a name from a hat."

Everyone looked around at one another and still no one said anything.

I sighed gently and raised my hand and said "I'll stay Allison."

Looking very relieved she said "yes! Thank you Chase! Hopefully it won't take us long to get the project done."

Everyone smiled at me and one of my work friends gave me a high five as the rest of the team left for the night. I figured in addition to the overtime money on my next check, I'd have at least scored some points with my coworkers.

After everyone else had left, Allison explained the project and what we needed to do. Normally we'd have weeks to finish an assignment like this, but we'd just have to do it all tonight. It didn't sound too bad though. I started on my end and Allison went back to her office to work on hers.

After about an hour she came back over to my desk and said "are you getting hungry? Lets order dinner. The company can at least feed you for staying late."

I was getting hungry and said "thank you, I am. Chinese?"

Allison smiled and asked what I wanted. She placed the order and 30 minutes later I rode the elevator down to the lobby to pick it up from the delivery guy. When I got back to our floor with the food, Allison invited me to eat with her in her office. Her office was small, but it was nice. It had a window that had a pretty great view and a very expensive looking desk and chair. I sat on the opposite side of her desk in one of the guest chairs and unpacked the food.

As we ate she said "thank you again for staying and I'm sorry to ruin your Friday night."

I said "oh no problem. I didn't have any plans tonight anyway."

She said "me neither. I usually watch movies with my cat on the weekends. I thought you might have had plans with a girlfriend or something."

I said "I wish, I feel like I've been single since the Carter administration."

She laughed and said "You're barely in your 20s, you weren't alive for the Carter administration."

I said "maybe so, but this is the first dinner I've had with a woman in a long long time."

She said "oof sorry it's take-out with your boss at work instead of with some young girl at a swanky restaurant."

I said "eh, I've had worse dates. Uh, not that this is a date, but you know what I mean."

She laughed and said "I totally do! I hope you never have to date in your 40s, it's awful. Everyone is divorced or has kids. I even like kids, but children can add a whole additional layer of complication to a new relationship. I'll think I found a good guy and think 'hmm, why is this guy still single?' and then a few weeks later it'll be like 'oh, THAT'S why he's still single.' When I was in college, dating was easy, even for an introvert like me."

I could see her still getting plenty of attention from guys, even if they didn't turn into boyfriends. Allison was pretty attractive even without makeup or sexy clothes. She could be outright hot if she wanted to be I thought. Which wasn't an appropriate way to dress at work obviously. I was starting to wish this was a date instead of a work dinner.

I chuckled and said "yeah that sounds rough. Dating in your 20s is hard too though. You pretty much HAVE to use some sort of dating app. Most people of my age can barely hold a conversation unless its through screens."

She said "you're holding a pretty good conversation right now."

We finished up our dinner and I said "thanks, I prefer talking face to face over endless text messages. Well, I'm going to get back at it. Shouldn't be too much longer before everything is completed."

I went back to my cubicle and went back to work. A few times I had to check with Allison on numbers and figures in her office, and she would come to my desk as needed too. I noticed that she was barefoot and had her toenails painted bright yellow.

She noticed me looking at her feet and said "don't tell HR. We're not supposed to wear open-toed shoes or be barefoot, but my shoes were killing me after wearing them all day."

I said "I don't think HR needs to hear about this bit of trivia."

After a few more hours, I was finally finishing up. I looked at my watch and it was nearly 10pm. Still fairly early for the weekend. I checked in with Allison and she was about finished too. I waited in her office until the project was completed and submitted to the higher-ups.

She said "thank you again for staying late with me. Shall we head out?"

I said "it was no trouble. And yes lets get out of here."

She slipped her shoes back on and we got in the elevator together. I was trying to work up the nerve to ask Allison to have a drink with me when we got to the bottom floor but the elevator lurched and stopped descending somewhere around the 8th floor. The elevator cab went completely dark.

She said "crap! Blackout?"

The emergency light kicked on and we were now in a dim light instead of pitch blackness. Blackouts weren't uncommon in the summer time when the temperature was usually around 110 degrees.

I said "maybe? The power will probably turn back on in a minute."

But after about five minutes it still hadn't. I tried the emergency call button but nothing happened when I pressed the button. We tried to pry the doors open but they wouldn't budge.

Allison said "I guess that only works in the movies."

I shrugged. I checked my cell phone and I had a signal at least. I put it on speaker and dialed 911. It rang several times before someone picked up.

The dispatcher answered and said "911 what is your emergency?"

I replied "I'm stuck in an elevator with one other person in the AGS Tower downtown."

The dispatcher asked "is anyone hurt?"

I said "no, we're unhurt but we're stuck. Can you send the fire department or something?"

The dispatcher said "yes, but it could be some time before anyone gets to you. Power is out for most of the city. My station is getting calls from all over the city and unless you're seriously injured all emergency services are all on more urgent calls."

I said "okay, I understand."

The dispatcher told me to call back if there's any kind of injury or if the elevator started working again so that she could cancel our call.

I sighed and said to Allison "well, looks like we're not going home quite yet."

She nodded and said with a groan "god, I'm sorry you got stuck in here with me. If you hadn't volunteered you'd be home right now."

We sat down on the ground and I said "it's alright. It's not like we could predict a blackout."

She said "still, it sucks. I'm sure you'd rather be anywhere than stuck in here with me."

I said "actually before we got stuck I was working up my courage to ask you out for a drink."

Her eyebrows rose in surprise and she said "oh! Well, I would've said yes."

I took a water bottle out of my messenger bag and passed it to her and she sipped and I did too when she handed it back.

I smiled and said "I was picturing cocktails but I guess this will have to do."

She smiled too and said "I'd love a mojito right now. It's getting hot in here."

She was right, without the air conditioning running, it was already getting warmer inside the elevator. Her hair was starting to stick to her forehead due to her sweating. I could feel sweat dripping down my back. I reached into my bag and took out two file folders and handed one to her. I used the other to fan my face with it. She nodded and did the same.

I asked "do you mind if I take my tie and over shirt off?"

She shook her head and said "no, get as comfortable as you can."

I undid my tie and unbuttoned my shirt and took it off. I was still wearing a white undershirt but getting out of long sleeves felt great.

Allison sighed and said "I wish I could do that. If I had known we'd get stuck in this oven of an elevator I wouldn't have worn this dress."

I said "you can at least raise the lower part up and get some air on your legs."

She thought about it for a second and then shimmied her dress up to a little above her knees, to about the midway point on her large thighs. She was still modestly dressed but it was more skin than she'd ever shown in the office. I looked at her legs appreciatively until she cleared her throat.

I quickly looked up and said "sorry, I didn't mean to stare."

She grinned and said "it's okay. I usually leave my legs covered because my thighs are so fat. Once I turned 40 it seems like everything I eat goes straight to my hips and butt. I used to wear leggings and tights in my younger days."

I said "your ass would look great in leggings."

She laughed and said "thanks, but most people would disagree."

We got quiet for a bit after that. We each looked at news on our phones for nearly an hour. The whole while it got warmer in the elevator. We sparingly took sips from my water bottle.

Allison said "this damn blackout. I feel like I'm going to pass out. My hair is probably a mess."

I said "your hair is fine, but your cheeks are really red."

She asked "if I raise my dress up more, will you be a gentleman?"

I said "you can take it off altogether if you want to. We may be in here for a long time. Get as comfortable as you can I say. I can face the corner if you want me to."

She said "that's okay, this is just a weird situation."

I watched as she raised het dress up over her head. She was now sitting in front of me only wearing her bra and underwear. Both were functional and black but I felt my dick twitch and begin to stiffen at the sight. I used my folder to help fan her body while she did the same. She wadded her dress up and used it as a pillow against the wall behind her head.

She closed her eyes and said "hmm, that feels better. This never leaves the elevator by the way. Agreed?"

I said "agreed."

She opened her eyes, smiled and said "you're staring again."

I had been looking at her breasts and bare thighs, I moved my eyes up and said "shit sorry."

She shrugged and said "don't be sorry, it's kinda nice. I don't feel sexy very often. Most guys don't like fat ass girls."

I said "oh your ass isn't fat, it's perfectly thick and I definitely think you're sexy."

She nodded at me and said "I can tell."

I looked down and my dick was noticeably rigid in my pants. I covered it with my discarded dress shirt and stammered an apology.

Allison giggled and said "it's alright! It's a perfectly reasonable response to having a mostly naked woman sitting in front of you. I'm going to lay down and press my stomach against the tile. It might cool me down some. Is that okay?"

I nodded and watched as she stretched out face down. I got to see her huge panty clad ass for the first time. I wanted to squeeze it but I was still well aware that this was my boss. I didn't want to do something stupid and get fired if I was reading signals wrong.

I was about to say something when she said casually "you can take your pants off and be in your underwear too if you want. This cool tile feels great on my stomach."

I didn't need to be told twice. I pulled my undershirt off and took my khakis off. I laid down next to here on my back, using my clothes as a pillow. I sighed in relief. The tile started to cool me down. We laid next to each other in silence for so long I thought she had fallen asleep, but she shocked me by moving her hand to my cock. She slowly rubbed it through my briefs, making me grow even harder. I tentatively reached over and started rubbing her round ass through her panties. I heard her let out a sigh. I squeezed and rubbed her ass in circular motions. Slowly alternating between her left and right cheeks.

After a few minutes, Allison reached inside my underwear and slowly stroked my dick. Her fingers felt really good and I sighed as they wrapped around my shaft. Following her lead, I slipped my hand under the hem of her panties and squeezed her butt without anything between it and my hand. Without saying anything, she withdrew her hand from my briefs and then rolled onto her back. I sat up and moved in front of her. I pulled her black panties down and she lifted her ass up to allow them down her legs. Allison had a dark triangular patch of pubic hair and I could immediately smell the musky scent of her pussy.

I removed my underwear and reached for her snatch. She spread her big pale thighs to allow me access. I ran two fingers on my right hand up and down her slit and I heard her let out a quiet groan. She was wet and ready for my fingers as I pushed them inside. I started to slowly move them in and out of her while I used my left hand to rub the inside of her thigh. I fucked my right hand in and out more quickly and moved my left down to her pubic hair. I ran the fingers on my left hand through it, enjoying the hairy softness until I used my left thumb to find her clit. She convulsed a couple of times when I touched it and gasped.

Sweat was dripping down her face and body as I slid my fingers in and out, in and out making a slick wet sound on each stroke. Allison's breathing had become shallow and I knew my stimulation was about to get her off. I curled the fingers on my right hand upward and she started cumming with a loud moan. Her body shook and her cunt held my fingers tightly in place. She pushed my left hand away from her clit as she rode out her orgasm.

With closed her eyes she said "fuck, that was good. Put it in me now please."

She pulled my right hand up to her mouth and started licking her juice off while she used her other hand to guide the head of my dick into her dripping pink slit. I sank my cock into her all the way to the base in one slow motion. It was hot, wet, and snug. I let out a moan as I started to fuck her. After my fingers had been cleaned off, I used one hand to support myself in the missionary position and used the other to pull her bra down to expose her breasts. They weren't overly large, but they looked nice in the dim emergency light as they bounced with the rhythm of my humping. She had small nipples, and areolae the size of nickels. Sweat dripped off my body and fell onto her tits and stomach.

I looked down between our bodies and watched as my dick plunged into her pussy over and over. Her big thighs were rubbing my sides while our bodies collided with a slapping sound. I was pulling out almost completely before thrusting back inside with a deep strokes. I leaned down and kissed her and I felt her tongue dart passed my lips and into my mouth. As we kissed, her cunt squeezed my cock even more tightly and I felt her get wetter. I kept up my pace as she came again. She broke the kiss and moaned and gasped her breath into my face until her orgasm subsided.

She said "god yes, are you close?"

I nodded and said "yeah, but can I fuck you from behind?"

She grinned up at me and nodded. I pulled out of her and she sat up. She took my cock into her mouth and sucked her cum off of it before turning around in front of me. Her giant round ass was pale and I wasted no time slipping all the way back into her boiling cunt. I noticed she had dimples on her lower back where her ass cheeks met her back. Her butt was wider than my body on each side as I thrust into her. I held onto her hips and humped into her as hard and fast as I could. Allison huffed out a breath each time I slapped against her ass and thighs. I watched her butt as it bounced and jiggled in waves each time I humped into her from behind. I barely lasted 30 more seconds once I started fucking her doggy style.

With a deep groan of pleasure, I pulled out and aimed the head of my dick at her back dimples as I came. My first shot splattered the dimples and the small of her back. My second shot roped out onto her left butt cheek. My third and fourth spurted halfway up her sweaty back. My last shot dribbled out into her crack and covered her butthole. My cumshot was all over her giant butt and back.

When I was done, she flopped bonelessly back onto the elevator tile and I collapsed back against the wall. Sweat poured off of our bodies and we were both huffing and puffing like we had been jogging. Eventually I caught my breath and used my undershirt to wipe all of my cum from her back and ass the best I could in the dim light.

She said "thanks. That was wonderful. It's been ages since I've had sex with anything other than a toy."

I said "I'm glad it was good for you too. And I'm in the same boat, it's been months since I last had sex."

She said "I hope you don't think me a slut. I don't make it a habit to have sex with subordinates. Hell, I usually don't even date men from work. I just got horny laying mostly naked in front of you, and since you said you were going to ask me out, I figured you'd be interested."

I replied "oh I'm interested. And the sluttier the better in my opinion."

We laid naked in the elevator for another 20 minutes just talking before the lights finally came back on. We scrambled back into our clothes as the elevator started to descend again. I had put my dress shirt back on, but not the undershirt since I had used it to clean up. When we got to the lobby, I checked my watch. It was almost 1am. I called the police dispatch and let them know we didn't need a rescue anymore. The night air was warm, but compared to the stifling elevator, it felt like a refrigerator.

I said to Allison "I need a shower."

She agreed and said "same. I'm sweaty. And cummy."

I laughed and I said "sorry if I didn't clean you up very well, it was pretty hard to see in the dim lighting. Would you want some company in your shower?"

Allison smiled and said "absolutely, my place is only a few miles away."

We walked to our cars and I turned on the A/C full blast as I followed Allison to her house. By the time we got to her place I was nearly cooled off. We parked and I followed her inside the front door. A white cat was inside on the couch when we entered.

She said "this is my cat, Lila. Lila were you worried about me? I was stuck in an elevator with a handsome bachelor."

The cat looked supremely uninterested. Allison rolled her eyes and went to her kitchen and poured food into the cat's dish. Then she took my hand, kissed me, and led me to the bathroom. She started the shower and then took her dress off. She hadn't bothered to put her bra and panties back on when we had gotten dressed.