In the Office With My Older Boss: Pt. 2 [M21/F39] [College Student] [Older Woman] [Slow Burn] [Passionate]

[This is a follow up to my previous story. I tried to write this so you can enjoy it without the context, but if you’re interested you can find my other story here: https://www.reddit.com/r/eroticliterature/comments/xmzmtt/late_in_the_office_with_my_older_boss_m21f39/

I hope you enjoy.]

My eyes kept tracing the outline of cracks along the ceiling. My alarm would be ringing in a few minutes, but I’m already wide awake.

I barely slept last night.

My head pounded from the two bottles of wine my boss and I polished off in her office. I had made the drunken walk back to my dorm while my boss called a cab to head home. I would have offered her to crash at my place, but I had a feeling sleeping in a dorm room after the age of 30 is not appealing to some people.

I roll over. There was no way I was getting back to sleep. The images of yesterday still played in my mind. Thoughts of going down on my boss in her office late at night. Images of her reciprocating with her own oral skills. Like a movie replaying over and over.

Unfortunately, I felt too guilty to enjoy it. Not that anything I did was wrong. I mean she started it. Kind of.

Or should I say that I wouldn’t have made a move if she didn’t give me such an obvious invitation. I laid in bed trying to remember every detail on how it started. Not because I was horny, but because I was starting to feel the pangs of guilt again.

I didn’t care if I lost my job. That was never the issue. I just couldn’t face the idea of making my boss uncomfortable around me. I really respected her, and to think that I may have ruined that had been bothering me. I didn’t want things to be weird between us.

Or maybe I was just overthinking things too much. Isn’t this what adulthood is about? Being drunk and doing stupid stuff that you’ll regret the next day.

Normally I’d be off today, but Sara, my boss, had asked me yesterday to come in for a few hours. Our late night, was really a part of a launch for one of our big projects. This meant that the expectations were for a busy day of issues to deal with today. I could understand the need for me there, although I now started to regret agreeing to come in.

I checked the time again. I had a morning class that I was supposed to attend; however, seeing as how I skipped my night class yesterday, I’m going to keep this train of poor decisions going. It’s actually fine. I really don’t need to show up to this class anyways and I could use some breakfast to soak up this wine swimming in my head.

I had made a few stops around campus. I hit up my usual hang over cure from the cart across the street and made sure to stop by my friend’s room on the way back to grab some extra medicine.

“Man, you look like shit.” My friend, Sean, loved to point out the obvious to me.

“Yeah. I worked late last night. Yo, I’ve got a pounding headache. You have anything strong I can take?”

“I think so. Check the cabinet.” He offers as I’m already raiding his medicine cabinet. “So you and Sara had a late night. Did it get steamy?”

Damnit. Sean had seen Sara one day when he was waiting outside work for me. Sara and I had left the building together and parted ways before I ran into Sean. However, Sean already got a peek, and now he never shuts about how I should be hooking up with my boss. Like it was the main point of going to work. Luckily he didn’t know that I actually took up his advise.

“Do you have any concept of what an H.R. violation is?”

“I’m just saying. If it were me, I’d had done the deed already.”

I normally wasn’t in the mood for his Sara fantasies, but today I especially didn’t want to discuss the topic. “Yeah. Good advice. I’ll let her know that.”

“You’re seeing her?”

“Yeah.”

“Lucky you. Tell her I say hi.”

I walked back to my room, finished my breakfast burrito, downed my headache remedy, and hopped in the shower until the warm water dulled my pain. I kept thinking of what I was going to do when I got to the office. Was it going to be weird?

Damn. Porn always made these moments sound hot. They never show you what happens after. Like, does the pizza guy still expect to get paid? It’s not like he owns the pizza.

I get ready, grab my bag, and start my walk down to the office. I keep playing different scenarios in my mind as I navigate foot traffic.

Should I apologize? Face the awkwardness head on and just say things got crazy? When I left last night she seemed in a great mood, but after splitting two bottle of wine I don’t think she processed the consequences. I imagine her waking up with the same feelings of regret.

What if I just pretend like nothing happened? We were a little drunk. We did some things. Why should it be a big deal? Except for the part where I told her I fantasized about her a lot. I can feel my face turning a bright red as I remember my late night confessions. I don’t know what possesses me to talk sometimes.

The office comes into view and I’m feeling nervous. I pause, afraid to walk any closer. I should just call in sick. I can’t do this!

Except, if I’m sick, I’d have to text Sara to let her know. That’s even more awkward.

No. It’s important for me to show up today. I have to go. I can separate business and pleasure. Sometimes.

I make it to my desk and sink into my chair. Sara looks to be in a meeting. Postponing the inevitable. I have no work waiting for me so I stream some TV and only half-pay attention. Most of the time I’m looking at every person walking down the hall wondering if it’s her. At least my headache has gone.

It took 45 minutes before Sara finally appears coming down the hall. She hadn’t notice me yet and when she approaches her office she walks straight in, flicks the switch, and shuts the door.

I sigh. Things are going to be awkward.

“Mark, can you come here?” I look up to see Sara poking her head out.

This is it. My heart sinks.

“Can you shut the door?” She says as I enter. I close the door and take a seat. The same seat that got me in trouble yesterday. I feel dirty sitting here. It’s starting to dawn on me how much of a stupid move I made. I feel the urge to apologize, but I stop myself.

“About last night…” she begins.

“Yeah.. umm..” I start to interrupt, but Sara cuts me off.

“Let me start by saying it was a lot of fun. It really was, but things are going to be complicated.”

“I understand.” I say, but Sara appears to be intent on saying what she has to say.

“Look. I have a meeting in 25 minutes, so I don’t have a lot of time. You’re working tomorrow like normal, right?”

“Yes.”

“Maybe you can hang around after?”

“Of course.” I start to dread the idea of having to wait 24 hours to receive a speech on how what we did was wrong. I can imagine tossing and turning in bed tonight as the anxiousness builds. Like a prisoner waiting on death row. At least she could look me in the eye today.

I start to say something, but realize it wouldn’t be helpful.

She stares at me for a moment, then gets up from her desk and moves towards the door. I stand, expecting her to excuse me. Instead she closes the blinds on the door and grabs my hand guiding me to the wall beside the door. As she keeps her eye on the door her hand reaches down to my crotch.

“What the fuck?” I say looking over at her.

Sara’s head snaps in my direction. The look in her eyes says it all: “Shut the fuck up! Are you trying to get us caught?”

Sara’s office was on the inside of the building. The only window was a small little window in the door. It came with tiny little blinds to shut for “privacy”. Unfortunately, this company didn’t really have a privacy policy. The blinds could be used to get a small reprieve from prying eyes, but closed blinds were in no way a “do not disturb” sign. Even I, a lowly part-time employee, would only simply knock before entering Sara’s office if the blinds were closed. We were in no way safe.

I bit my lip and closed my eyes. Knowing it was my best chance to keep my mouth shut. Maybe I also hoped that if I kept my eyes closed, anyone who happened to enter wouldn’t see me.

I struggle to keep quiet as I can feel Sara’s hand start to massage grope me over my pants. Something about her massaging melting away all the anxiety I’ve been feeling. I lay my head back against the wall. This is the best way to find out you’re not being fired.

I open my eyes and look over at her. She’s still focused on the door, looking through the cracks in the blinds to see if anyone’s coming. The feeling of my eyes on her causes her to turn. She gives me a smile. A sensual playful smile. The kind she gave me last night. Holy fuck this feels good. She grabs my hand and places it on her chest, winks, then blows me a kiss, and finally goes back to looking at the door. I close my eyes again, enjoying the feeling of our hands groping each other.

I feel her begin to unzip me. She reaches in to grab my cock. I’m worried she’s going to assume I’m always this rock hard, but yesterday was the hottest fantasy of my life and today was a completely unexpected turn of events. I can’t help that all the blood in my body made its way down to my now pulsing cock.

I open my eyes for a peek at Sara again. I catch her looking down at my member. Damn. I never had someone admire my cock in front of me before. She sees me peeking and smiles again. This time she brings her hand to her mouth and spits. She then begins to lube my cock as she watches my desperate reactions to her touches.

Sara finally grabs my hand and moves it to her ass. She leans into my ears and I shut my eyes as the feeling of her breath against my neck sends a shiver down my spine.

I bite my lip as I hear her voice finally whisper, “pinch my ass when you’re about to cum.” I stand frozen. I can only nod in reply. Her head moves away and I assume she continues her vigil looking out the door.

I wish I could say I lasted all 25 minutes, but can anyone blame me for barely making it to ten? I had expected to be clearing out my desk by now, or sitting in a meeting getting scolded for my inappropriate behavior. Instead, the woman I’ve fantasized about for the past few years was stroking me despite the chances of us getting caught.

I feel my blood boiling as I think about how hot the situation was. I can’t take much more and I pinch her ass. I don’t bother opening my eyes, but I hear the sound of her moving and before I can reconcile the sounds with what I think she’s doing I feel her lips engulf my cock.

It’s too fucking much. I explode, griping her head as I try with all my power to make sure I don’t moan and ruin it all. You can hear the shaking as I breath through my nose. Desperately holding a moan as I feel the cum pour out of me. Holy fuck this was exciting.

As the last drip exits me, I want nothing more than to collapse on the floor in ecstasy, but the sound of Sara moving reminds me that we were lucky to make it this far without an interruption. I can’t press my luck much more. I push my cock back into my pants and make my way back to my seat as Sara rounds her desk and sits back down in her chair. I feel cheeky having pulled this off.

I look over at her as I sit again in the chair I felt so dirty sitting in before. I feel dirty sitting in it now, but this is a fun kind of dirty. I look over at her. She’s smiling at me. Damn, she looks so beautiful. I can’t believe I was so nervous. A wave of relief passes over me.

And then she opened her mouth.

Fuck. I was so wrapped up in not getting caught that I didn’t realize, sitting before me was Sara, leaning over her desk, her mouth dropped open with a pool of my cum floating over her tongue.

And then… *Gulp*.

She smiles again at me showing an empty mouth. “Mmm.” she moans to me.

Holy fuck.

I sit there. My body shakes as my mind processes what it just saw.

“Fuck, that was hot.” I say to her. Trying to keep my voice down, but I’m so distracted by everything going on it’s hard to control myself.

“That was a lot of fun.”

“I thought you said things were complicated.” I ask. Not knowing why I was complaining. My mind was all over the place and my head wasn’t filtering what we were saying.

Sara looks back at me with a look of confusion until it clicks, “Oh! Yeah. It’s going to get harder to sneak around and not get caught. Late nights aren’t always possible for us. People are going to suspect things if we stay late every night. We’re going to have to be smart.” She smiles. “I won’t see you again before you leave, but I was thinking, maybe tomorrow night if you want to stick around a little?”

“Oh, fuck. Yeah.”

“We could have a lot more fun than last night.” Sara leans forward a little. “I’m sure you have a lot of fantasies that you’d love to re-enact with me, right?”

“A whole catalog. I wouldn’t know where to start.”

Sara smiles, obviously a little flattered at this young man openly admitting to fantasizing about her. I see her hand start to move over her body.

“A whole catalog of things you’d do to me? Do you really think that much about me?” Her hand trails south. I can’t see through the desk, but I hear a zipper.

“Of course. Like I said, I’ve always thought about you. Your hot little outfits. My naughty boss.”

Her face gives away the moment her hand slid into her panties. I try to lean back to get a peek, but the desk is still in the way. I try to enjoy the look on her face.

“I’m your naughty boss?” By the sound of her voice I can tell she was turned on by the idea of being the naughty boss her young employee fantasized about.

“The naughtiest.”

Sara shut her eyes.

As I looked at her, it dawned on me. Sara must have always been self-conscious. Perhaps the march of time and child care did a lot to her confidence and now she was the subject of someone’s desires. Above all else, she felt naughty. It was driving her wild inside.

I had always fantasized about this woman and she gave me two of the most memorable sexual experiences. I highly doubt I’ll ever top how hot it felt being in this little office. I owed her.

“I’m sorry, Sara.” I say, catching her off guard. Her eyes open a bit, looking at me.

“Huh?” A hint of confusion tries to break it’s way through the pleasure her face originally betrayed.

“For not being able to stay late with you tonight.”

She gives an innocent smile, “Hah, it’s fine. I can wait.”

“No, it’s not fine. I’ve been such a terrible employee for you.”

“Oh, Mark. Don’t say that…”She replies. Her hand slows and a look of concern crosses her face.

“I think it’s unfair. Which is why I’ll be ready tomorrow once everyone leaves.”

Her eyes now squint at me, “Ready for what?”

I lean forward to match her stare. “For my punishment.”

Sara melts before me. Once I’ve uttered the word “punishment” her mind was sent her over the edge and she bites her lip. “Fuck. What did you say?”

“Tomorrow. When we’re alone. I’m ready to accept my punishment.” I lean closer to her. “Even if I have to get down on my knees and beg for your forgiveness.” Sara’s eyes shut tight. I lean closer. “Ma’am, will you ever forgive me. Please?” I coo into her ear, my cheek brushing against hers.

I can feel her breath against my face. I hear her whisper, “Oh my god.” as I continue.

“I’m ready to serve you anyway I can.”

Sara shudders.

“Ma’am. I want nothing more than to be your obedient…” Her breath quickens.. “dutiful”.. a whimper.. “fuck boy.” Her hand quickens her pace as I slide closer to her ear.

In the quietest whisper, my breath passing over her ear, “But just remember one thing… when all is said and done.. tomorrow night.. you will be here.. bent over this desk.. and I.. Will.. Fuck You.” At the end of “Fuck You” I kiss her ear gently.

The feeling of my kiss against her ear and the thought of employee fucking her against her desk was too much. I can hear the chair creek as her ass shakes and shudders. She bangs her fist against the table in an attempt to control herself. I fall back into my chair hoping no one heard.

Sara mouths the word “fuck” over and over knowing she can’t make a sound, especially after slamming the desk. She grabs ahold of the desk and rides her orgasm until she collapses back in her chair.

I look at the clock on her wall. “Looks like you need to get to your meeting.” I joke, knowing that she’ll need some time to collect herself. I stand to leave, but before I make it to the door handle I hear Sara interject.

“Wait.”

I turn to her. She collects her breath and breaths one final deep breath. She attempts to compose herself and then approaches me at the door. Her hands reach for my face and she pulls me in for a kiss. I look down at her. She’s beaming.

“You know that cute blue blouse and tight little suit I have?”

“Yeah.”

“That one’s your favorite. Right? Don’t deny it. I’ve caught you checking me out in it before.”

I know she’s right, but I decide to be cheeky. “Maybe.” I smirk, “Why?”

She smirks back. “See you tomorrow.” And pushes me out the door.

[Feel free to send me DMs/chat if you have any suggestions or feedback. Please leave a comment if you have some thoughts. I love knowing where I can improve, and I really appreciate the feedback.]

Source: reddit.com/r/eroticliterature/comments/xpor25/in_the_office_with_my_older_boss_pt_2_m21f39