[This is a part three follow up to my original story. I wrote this in a way that hopefully you can enjoy it on it’s own, but if you’d like to start from the beginning you can find the other stories in my profile.]
I find myself laying in bed again, using my eyes to trace the cracks in the ceiling above. It seems like this is a reoccurring moment for me these past few days. At least I slept a little better tonight than before. I find some solace in knowing that this time it’s not because I fear the consequences of fooling around with my boss two day’s ago after a few bottle of wine. Instead, it’s anticipation into another “late night” at my boss’s request.
Luckily when my head hit the pillow last night, the scenes of these past two days was enough to quietly rock me to sleep. Like sugar plum fairies dancing in my head, I reminisced on finally fulfilling years of fantasies for my much older, yet still attractive, boss. The college kid in me felt like I had won the lottery twice.
However, in the middle of the night I had awoken during a dream where my boss and I finally went all the way. The vision of my cock sliding into her from behind jolted me awake and ever since then I couldn’t find the chance to fall back asleep. My mind was constantly racing to the prospect that tonight would be another hot experience to spend my life looking back on.
My only saving grace was that I had only awoken a few hours ago and due to the lateness in my schedule, it was already afternoon. I had one class today and then I would be heading back into the office, so I found myself with the perplexing feeling of excitement to head back to work. I remind myself that it won’t be long now until we’re together again. One more class, then I’ll shower, and then back to the office.
I made it to class a little early. Expecting to be distracted by the upcoming event, I find that my lack of sleep, the blasting heat in the classroom, and the droll of Prof. Ben Stein had me nodding off. This was good news for the first 20 minutes of my snooze session, but I soon was having dreams. Nothing too full. Just visions of my boss on her knees with my cock in her mouth. The sound of her moaning as I run my tongue in-between her slit. And then I hear her moan. I can see her bent over in front of me. Looking back. Begging me to enter her.
I startle myself awake. My head already looking down I peer unflinchingly at my crotch. The dream was so exciting that I had to try my hardest to will my cock from not poking up in the middle of class through my loose shorts. My fear is that someone will notice my growing member and I’ll be mocked out of class. I had a reputation to keep.
Rational me would have realized that 50% of the class was also sleeping. The chances anyone noticed was slim, and yet, I felt my blood pumping more. This woman was making me go crazy. This only added fuel to the fire of how much I wanted tonight to come. I slowly position myself to help cover any bulge and resume some post nap daydreaming.
I think back to seeing her bent over. Hearing her moan as she looks back at me. I can start to picture the moment in my mind again when a buzz in my pants distracts me. “Fuck” I almost say aloud. That wasn’t the ideal time for a sensation to be going off down there, but I remember I left my phone on vibrate.
My barely dim screen reads, “Sara +1 Message”. It’s my boss. I don’t know why my first thought was that tonight was being cancelled. Maybe I was always in disbelief of the whole situation and fully expected it to end in a fiery crash. Maybe I suspected Sara was going to wise up to cheating on her family with a college student nearly half her age. We were two unlikely bedfellows.
While Sara might not have been the swimsuit model everyone expects of their fantasy girl, I bet she turned heads at every bar she went to. So to think that this arrangement was a real life event was too hard for my mind to reconcile. Sure, maybe I was feeling a little down on myself and I half expected this to explode in my face.
My mental dilemma is jolted by my hand vibrating. “Sara +2 Messages”. I realize I’m being childish. At worse she’s merely telling me something is up and if we can meet tomorrow night instead. It’s fine. I don’t know how many nights I can last, but I’m willing to try. I pull open the phone.
I had my answer. I no longer had to think of how many more nights I could last. Instead I needed to know how many more seconds I needed to last. In the well light shine of my phone I see the two messages that Sara had sent.
Message #1: “I can’t stop thinking about you and me later.”
It’d be an understatement to say that this message only ‘set my body on fire’. I felt pins and needles explode throughout my body. Spreading like a fever beneath my skin. A sharp pang strikes my crotch as the anxiousness builds.
At this time though, the second message loads and an image appears.
Message #2: *An image of a hand appears. Sara’s hand. In profile in front of her phone. Her ring finger and middle finger touching tips with her thumb being the focal point of the image. Through the crystal clear quality of my phones screen I can see the light sheen over the tips of her three touching fingers. They appear wet.*
I tense so hard my calf start to cramp a bit. The image catching me completely by surprise. With all my energy I focus on two main tasks: Firstly, I try not to draw attention to myself in the corner of the room. Secondly, I urge myself to not cum in my pants. I fight back the ache of seeing my boss’s finger wet from thinking about me. My balls ache. There’s no doubt in my mind that they want to fuck her. Tears form in my eyes as I try to calm myself.
Luckily I had a hoodie on and this was up over my head. I tried to look down and use as much cover to hide the pained look on my face. I spent several moments holding myself back. Trying every manner of breathing to finally get to the point where a gentle breeze wouldn’t set me off. Once I can handle moving I exit out of the back door of the room.
This woman had a habit of affecting my classroom attendance, but that was an issue I’d resolve later. Right now I rushed back to my dorm and crank on the cold water to my shower. “Fuck” as the ice cold water hit’s my body. I can see how this helps. I finally get my mind under control and move the water back to hot. Letting myself relax a bit as I wash up.
I’m a little early since my “premature” exit from class, but I know I won’t do any good sitting in my dorm so I head over to work and decide to use the extra time to maybe get a quick chat with Sara in. I make my way down to the office in record time. A little extra pep in my step gets me to my desk faster than expected and I guess I was moving a little quick. I had a bit of an out of breath look when I finally sat down.
My body making it to the chair coincided with Sara exiting her office and she had a surprise on her face when she saw me. Then a brief moment of confusion and soon a revelation crosses her face. I haven’t a clue what made her laugh, but she shook her head laughing and continued down the hall. It hit me as soon as she was out of sight, my out of breath appearance and early arrival at work wouldn’t seem so confusing if it weren’t preceded by her risqué correspondence. My boss thinks I sprinted to work after she sent me a dirty text.
I try to focus on doing some work, but I feel a little humiliated at the thought that I didn’t play it cool. That’s when I feel a tap on my shoulder.
“Let’s go.” Sara walks past me and towards her office.
I follow her into and she shuts the door behind me. I immediately feel her push me against the wall and her tongue buries into my mouth before I get a chance to explain my early arrival.
“Fuck. I missed you.” She breaks away from the kiss and starts to rub my cock over my pants “Couldn’t wait after seeing my picture, huh?”
I don’t know what made my mind flip so fast, but instead of giving my prepared explanation, I just give a smirk and say, “I ran out of the classroom.”
Again, I don’t know what possessed those words from exiting my mouth, but the look on Sara’s face surprises me. She lit up at the idea of me bolting out of my class at the sight of her wetness.
“Fuck.. you wanted me that bad?” She asks as she bites her lip. Rubbing my pants faster.
“I nearly came.” I offer up.
“Fuck.” Sara backs away from me. Her hands now are on her body as she stands against her desk. A playful smile on her lips. I don’t think she believed me, but just the fact that I mentioned I left class for her seems to have turned her on.
“I was so wet for you.” She offers to me.
“I saw. I would have come sooner, but I couldn’t walk with the bulge you gave me.”
Sara nearly loses it. Her pants are open and her hand is buried in her silk panties. Her blouse, one of my favorites, is slightly open as she teases at her chest. I can’t help but feel invigorated by the power I have over her. Something about the image of a college boy fantasizing about her that sent her wild with passion.
As I said, Sara was attractive. She could have had a pick of any guy. She wanted me. What’s more is she wanted me to want her. And I fucking wanted her.
“I was so afraid I wasn’t going to make it out of the door before exploding.”
It finally hit Sara, I wasn’t kidding. “Holy shit.” She teases herself faster. “You were that turned on?”
“Of course. All I wanted since I saw that picture was to taste those fingers.”
Sara melts at hearing my desire to lick her wetness up. She stops her teasing and reaches out beckoning me towards her wet fingertips. I move towards her hand and take them in my mouth. She holds them in my mouth and guides me down to my knees. Her sweet taste fills my mouth as she moves me closer to her lower lips. Her other hand pulling her pants down to give me access to taste her.
“Please. I need you to calm me down. I have a meeting.” She begs. Fighting to get the words out. She’s hurting. In desperate need of a climax. I know the feeling so I bury myself into her slit and I can taste how long she’s been hurting. She’s dripping wet.
I push deep inside her with my tongue and I can tell she was already so close to climaxing. I knew I needed the tease around her a little bit longer and then I could rub my tongue hard against her clit. I knew she was ready once I passed over it.
“Oh god, right there.” She gasps. “Keep going.”
I set my licking to a constant flick over her clit. Her hand pulls aside her lips while her other forces me head harder onto her.
“Yes. Harder.” She begs as I can tell she’s getting closer. The shaking in her legs warns me of her immanent climax. Her hand moves from my head to her mouth and a muffled “Fuck yes!” is caught as she hits an orgasm.
She grips my hair hard as she braces herself onto the desk. Trying to stifle any commotion. I break free once her grasp loosen and I stand back up. Letting her get her composer.
Once she collects herself she gives me another smile.
“Like I said, I raced here for you.”
Sara laugh, “Did you really almost cum in class?”
“It was a close call. That picture was fire.”
She looks at her watch “I got 5 minutes.”
Before I react her hand is unzipping my pants and she’s on her knees licking my sensitive member.
“Oh fuck.” I let out. Cliché, but I can’t control my mouth at the moment.
“Your hot boss on her knees is a little too much?” She mocks me in between kissing and sucking my cock.
The feeling of her lips wrapped around my cock sends me back to my fantasies of her on her knees again. I can’t stop wanting her lips to pull at my cock.
“Let me know when you’re going to cum.” She winks at me and keeps sucking.
I can feel it getting closer. Her tongue working deep down my shaft. Looking down and seeing her face with my cock buried in it is too much.
“I can feel it starting.” I tell her.
She pulls my cock from her mouth and stands. Planting a kiss on my cheek.
“What the fuck!?” I shout under my breath.
“Shh.” She mimes. “I want you to save this all for me later. You’re going to fill me up? Ok. You just have to wait a little longer. Besides, didn’t you say I needed to punish you a little bit?” She winks.
I mentally kicked myself. In my infinite wisdom, yesterday while hyping up our night, I had mentioned to my boss that I needed to be punished. It was setup to telling her about fucking her, but I guess she picked up on that. I made a mental note of her attention to detail and stuffed my cock back in my pants.
I sigh. Two more hours of hell.
Sara grabs her stuff. “Look, feel free to camp out here until I’m back. We’ll finish what we started.”
With look of acceptance on my face I nod.
Sara sees the pain on my face and as she walks past she reaches down and grabs my balls. Her cheek brushes against mine and a familiar whisper fills my ear.
“You’re going to fill me up.”
I shut my eyes and don’t open them until Sara leaves. The idea of filling my boss’s pussy with cum is pushed from my mind. If I think about it the two hours will never pass.
I sit idle at her desk for several minutes. The idea of work is out the door. Considering my boss edged me before leaving the room, I’m taking a personal day in her office.
When Sara finally returns. I nearly jump out of the seat. I’m starting to lose it.
Sara sets her files down and sits me back in the chair. “Stay.” She commands.
She dims the office lights a bit and pulls a chair in front of me. She rests her suit jacket on the back and sits in front of me.
She starts to massage my thighs. “Sorry about before. I just kept thinking of you exploding inside me and I didn’t want to ruin the moment. I hope you understand.”
The feeling of her massaging the inside of my thigh numbs me. I only nod back to her.
“I know you were hurting, probably worse than me. I just got so turned on thinking of being filled by you. Punishing you.”
I hesitated a second, “You enjoyed that?”
She finally looks me in the eyes. “Yeah. The, umm.. you know. This younger stud being punished by this older woman. You wanting me. Begging me. It’s driving me crazy.”
I smile. She’s so enticed by my desire for her. It’s shocking how often I forget and how surprised I become.
“Well I know reviews are coming up. I know I don’t actually get one, but maybe this year I have a bad review.”
“Really?” Her eyes light up.
“I know I need this job, badly. Not just the money, but what would I do without getting to fuck you.”
She smiles. Her hands finally make it to my crotch. Massaging it. “Exactly.”
“Sara, I’d do anything to keep this job.” I smirk, “Please don’t fire me.”
I can see she’s blushing. Hearing this is getting her warmed up, but she’s trying not to show it.
“Sara, I know I deserve to be on my knees. Begging for my job. Burying myself into my work..” I let that hang.
I can see she loves this idea. “Fuck, we’re not even close to denting all of our kinks.”
I lean forward and plant a kiss on her lips. “I feel like we haven’t even started.”
A smile crosses her lips. I know she’s loving this. “When you fantasize about me. Do we fuck?”
“Sometimes.”
“How?”
“Well in class today, I started to doze off. I had an image of you…” I pause. A little embarrassed bringing up my near accident in class.
“You thought of us fucking?”
“A little. It was like a dream. Sort of.”
“What was I doing?”
“You were bent over this desk.” I motion to her desk
Sara looks over. As if a director in a movie, she feels she won’t understand this fantasy unless she acts it out. She braces herself over the desk. “Like this?”
I catch myself, “Well, yeah.”
She looks back at me. “What else?”
“Well you look back at me like that, only I’m obviously behind you.”
She looks at me with a wink. “Places people!”
I jump to my feet without too much prompting.
“Well, we’re fucking. So..” I reach around her and undo her pants, pulling them down to expose her perfect ass. This was the first time I was seeing it in such a view. I stop and stare.
“What?”
“I love your ass. I’ve always wanted it, but, now that I see it, I love it.”
Sara blushes. “You’re sweet, but I’m soaking wet and I can’t fucking wait.” She gives me a hurry up look.
I smirk. I savor the moment, but Sara has no time. She reaches back and grabs my cock. Pulling me into her. The feeling of how wet and warm she is rushes over my cock.
The moment I’ve always wanted. Having my cock glide into her dripping wet pussy with such ease and such warmth. Hearing her moan as I slide down to my base. She lets out a moan and covers her mouth. Not knowing if anyone was still lurking.
I’m lose myself in the moment and try to regain focus. I ease myself faster and harder into her until I hit the right spot. Sara moans, “Oh fuck. Just like that. Fuck me. Please.”
My boss begging me to fuck her. This is the dream. I grab onto her hip and pull her into my thrusts.
“Yes!”
I push deeper.
“Fuck me, Mark. Fuck me!”
I can feel the edging from all day building inside me. I try to focus. As much as I wanted to release everything I had inside her, I wasn’t ready to finish. She felt so good and I tried my hardest to hold myself together.
My toes curled and my grip tightened on her body as my thrusts got a bit hard. Sara was now thrusting back into me.
I could feel a tremble in her and she turned to me. The look on her face said it all. She was seconds from climax.
“I’m cumming..” These words tripped my own alarms. I couldn’t hold it anymore. Like a perfectly choreographed scene Sara hits her second climax of the night while I begin to release everything I had.
“Oh my god, Mark. Oh my god. I can feel it. Holy shit.”
I’m again too lost to recognize her shock. After being teased all day I was finally freeing that burden from below. It felt amazing holding her tight against me until the last drop left.
“Damn.” Was the last of her exclamations before I pulled out of her and let her collapse in her chair.
“That was hot.” I get out, trying to catch my breath again.
“Shit, you fucking filled me.”
I looked down at her. She was out of breath, but too concerned with the white fill about to leak from inside her.
“Holy shit that was a lot. Can you find me a a towel.” She says. It comes out like a command, but only a frantic command.
I look around the office. I’m not sure which of us expect to find a towel in the room. It was an office. I could run to men’s room, but instead an idea hits me. I pull her out of the chair. She looks with bewilderment. I ignore her and reach down, yanking her panties and pants back on.
“I prefer you better this way anyways.”
[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/y77g07/in_the_office_with_my_older_boss_pt_3_m21f39
I need the next part. Holy fuck.
!updateme
!updateme
!updateme
Subscribeme
!updateme