Taking My Manager Jen

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Nis 17, 2021 // By:analsex // No Comment

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“Over here is where you’ll be sitting for the week Sam.” said Jen, looking back while she gestured to an empty desk next to hers.

My head snapped up to eye level. I’d been hypnotized by my manager’s swaying hips from the moment she had greeted me at the door. Jen eyed me briefly before explaining where the bathrooms and breakrooms are on each floor. She and I had been working together remotely for over a year. I was based out of one of our satellite offices, so the first time she came to visit, I was pleasantly surprised.

Jen was a petite woman in her mid-thirties. She stood maybe 5’2″ with dark brown hair that brushed her shoulders, light skin and gray eyes behind square glasses. She was in great shape but not without bountiful womanly curves, her chest sloping generously and her hips flaring into a great ass. She was also married, but that didn’t stop me from wanting her, in fact it only made me want her more.

The problem was as a young associate just a few years out of college, even if she had been single, I wouldn’t exactly have been on her radar given our significant age gap, so I was never anything other than professional with her. I saved my fantasies for slow days when I would daydream about fucking her in a janitor’s closet or on one of the bathroom sinks. But those were just fantasies.

It had been several months since we had last worked together in person and now I was visiting her for one week. I was looking forward to being face to face, even if it was only shortly.

I was visiting for a series of vendor meetings. All of us had spent weeks preparing analyses and various presentations. After getting settled Jen and I spent the next several hours working together to ensure everything was on point prior to our scheduled appointments. As we worked, I couldn’t help but notice the rest of her outfit, the black pants she wore hugged her curves tightly, leading to my earlier distraction. She also wore a white form-fitting blouse that hugged her waist and healthy bosom. Her attire was formal and appropriate given our schedule, except for a few details: the buttoning of the blouse, which was one or two buttons lower than I would have expected for the office, was difficult to ignore. As we leaned together on the desk poring over documents, try as I might I couldn’t keep my eyes from drifting down to her chest to soak in her ample cleavage. At one point she leaned forward further to outline a graph that we were discussing, exposing a tight black lace bra beneath her blouse. She paused for a moment at this point, making my heart skip, worried she may have wizened to my game, but looking up and meeting her eyes, she quickly continued, as if she was just gathering her thoughts.

Many hours later, after hours of meetings, I dragged my feet back to my desk. Sitting blurry eyed at my computer, closing down the programs, all I could think about was driving back to my hotel room, falling into bed and passing out. But then Jen turned to me:

“Hey so I’ll pick you up at 6:30 at the hotel ok?” she asked.

I stared back at her blankly, confused.

“Our vendor dinner tonight? Fancy steak place?” she pushed, seeing my reaction. I had completely forgotten. Our day wasn’t over; I had to spend my evening hours entertaining business guests over dinner. Oh joy.

“Oh right, um…yea, ok see you then” I responded. If anything it was a chance to spend more time with Jen. So at least there was that. I left work tired, but happy that I at least was getting a free meal later.



I jarred awake in a panic. “Oh shit…!” I had come back to the hotel and fallen asleep. I quickly looked at my watch: 6:45pm


I walked to the door and opened it without thinking. Jen stood there, looking slightly anxious and amused. I stared back at her, she was still wearing the same blouse as earlier but it was barely half buttoned and her slacks had been replaced by a tight black skirt that reached to her mid-thighs, it was barely appropriate and I couldn’t help but stare.

“Uh…we have to go!” she said, trying to suppress a giggle as I ogled slack-jawed. I looked down at myself. Realizing I was shirtless I immediately felt myself turn red. Not that I wasn’t in good shape. I’m 5’11 and athletic with a healthy obsession for fitness that developed in college, so I have a nicely cut frame. But, this was my manager after all.

“Right! Uh…give me a minute!” I ran back into the room and threw on a fresh shirt. As I was buttoning it, Jen peaked her head around the open door.

“So uh, you keep yourself in pretty good shape huh?” she asked gingerly.

“Uh yea, it’s kind of my way of unwinding after work” I responded, still embarrassed.

“Well that’s good!” She responded, “How else do you like to unwind?” I found the question a little odd, but I didn’t pause to think about it, I was too busy tying my shoes to think too much about it.

“Well there are other ways I guess, but that’s the escort kartal most common.” is all I could muster.

We were out the door shortly.


Dinner was your typical affair – for most of it, two groups straining the make polite conversation. Not that I didn’t like our vendors, they were from Minnesota, nice folk. But the best part was the food: no one skimped on the meal being on the company’s tab. After a few cocktails we all ordered $70 steaks and plenty of wine to wash them down. Needless to say we were all best friends in short order.

Jen sat directly across from me, her cheeks flushed and slight sheen coming off her skin. As the conversation continued I found myself looking back at her frequently, my self-control weakened by the drink. I was surprised to find her eyes planted on me several times as I glanced towards her. Even when I looked away, I could almost feel her eyes still on me. Finally I couldn’t take it and decided strike up a conversation directly with her, I knew she and her husband had been looking for a new house so I decided to start there.

“So, how’s the home search going?” I asked lamely. She smiled slightly, leaned in and started telling me about the places she and her husband had frequented. She rattled off square footage, amenities and location but she sounded bored by the topic. My curiosity peaked, I probed, “So…what you don’t enjoy looking at the houses or do you just find talking about it boring?”

“Oh!” she pepped up and placed her hand on mine “I’m sorry, I didn’t mean to sound bored, I guess I just don’t find house hunting that interesting. Plus it’s taking forever.” she squeezed my hand slightly. A strange gesture, but I reminded myself some people are touchy when they drink.

“Why the hold up?” I asked, noticing her hand had lingered a few seconds too long.

Jen exhaled a big sigh, looking momentarily exasperated “My husband is traveling constantly for work, he’s in sales. It makes it difficult to look consistently when we both want to see the places. He’s actually traveling right now.”

Her response fueled my interest, I decided to put out a little feeler, I leaned in a bit “So if house-hunting doesn’t do it for you what does excite you?” I half-whispered the question and put a good amount of emphasis on the word “excite” but was subtle enough the no one at the table nor Jen would catch on…unless she wanted to.

She paused for a moment and made steady eye contact with me. I held her gaze for several seconds and could have sworn her cheeks flushed several more shades as we looked at each other.

“Oh I don’t know…” she responded slowly, “I guess, spontaneous things…” I was pretty sure I could sense a desire to say more: a hook had scratched skin. I pressed a little further to confirm my suspicion.

“Spontaneous things? Like what?” I asked nonchalantly sipping from my water “I’d love to hear about spontaneous things excite you.” I solidly crossed the line into overt flirtation, but I figured I still had some wiggle room to play it off if I was completely off base.

Suddenly I felt bare skin against my ankle. Jen’s leg. I almost choked on an ice cube as I inhaled sharply in surprise. I looked up at her as she spoke,

“Oh you know, just little things here and there.” she responded matter-of-factly. But her eyes made it clear it was no mistake.

…”Does that sound about right Jen?” one of our vendors cut into the moment, my eyes snapped to the rest of the group, convinced someone must have taken notice. Jen didn’t miss a beat, responding to the question as if she had been listening the whole time. Meanwhile she slid her leg further up my own, occasionally locking eyes with me expertly. I was having a hard time processing, the manager I had a crush on for months was feeling me up under the table yet was completely poised, a bulge quickly began forming in my slacks.

Apparently satisfied with the response, the group turned away from Jen. Her foot was now slowly caressing my lower leg. By this time I was able to regain my composure and wanted to see how far this could go.

“So, little things?” I asked, grabbing her bare foot as it rode up my leg again, “what about big things?” I placed her foot on the seat of my chair between my legs and gave her a daring glare. She nonchalantly cut another piece of steak and speared it with her fork while stretching her foot forward. Her toes met my straining rod as she placed the meat in her mouth. Her eyes widened as she looked at me and exhaled audibly.

“Fuck.” she whimpered. Causing one of the vendors to look over, he paused, watching her chew her steak for a moment “Pretty good huh?” he encouraged smiling, Jen nodded back with a blissful expression, all the while kneading the length of my tool with her foot, exploring.

“I love them. Big things.” she finally responded breathily. I grinned back at her, enjoying her acknowledgment. But I was surprised when she quickly recoiled her foot, maltepe escort wiped her mouth and took a long gulp of her water, draining the glass.

“But I’ve gotten so into the routine, I don’t really do the big things anymore.” she said quietly, a tone of bitterness apparent.

“That’s a shame, I replied. Why’s that?” I asked back seriously.

“It’s just reality. Being a good person, a good employee, and a good wife. I want to be those things and it’s difficult to be those things and do big spontaneous things. You just fall into a cycle.” she was staring at her lap now. My excitement shrank, along with my cock.

“I guess that is true” I conceded.” feeling discouraged. Too bad, a few glasses of wine and she turns into a huge tease. It was fun for a moment at least.

“Unless someone forces me to do something simultaneous, you know?” she said plainly, looking up at me. I glanced nervously at the others, they were absorbed in their own conversations, all drunk, all being way too loud, but it played in our favor.

“Excuse me?” I responded back not quite believing what she had just said.

“Unless I’m forced into it.” she repeated. “Sometimes people get forced into doing big things, they can’t be held responsible, but they can still enjoy them right?” she cracked a mischievous smile. My mouth hung open for several moments as I tried absorbing what she had just said, but somehow managed to regain most of my composure again.

“So you uh, would be excited by being forced into doing something?” I inquired slowly.

“I can’t think of anything more exciting.” she responded back dead-serious, “I would absolutely love it.” With that she turned back to the main group and struck up a conversation with a female coworker. I sat dumbstruck for several minutes absorbing what had been said. There was no way that had actually just happened, was there? If I was certain about one thing, it was that the cinder block in my pants needed addressing.


The car ride back was a silent affair. I drove Jen’s car, as she didn’t seem to be any condition to.

“Where’s your place” I asked. “I’ll get you home and take a cab back to the hotel” I continued, trying to convince myself more than her. Jen didn’t respond, instead she plugged an address into the GPS and sat back low in her seat, her eyes on me.

The GPS took us to the suburbs. The houses were spaced far apart with gravel driveways, huge lots and nice homes. As the voice over the car speakers let me know our destination was on the left my heart began pounding. What now? I turned into the driveway, the crunch of rubber on gravel the only sound and soon after that nothing. I put the car in park and looked over at Jen. Her eyes were still on me. As I stared, she played with her hair and raised an eyebrow. My heart was a jackhammer.

“I guess I’ll see you tomorrow then” she whispered flatly, pulling the door handle. I tried to think of a quick response but my throat was as dry as cement glue. She swung her skirted legs out the door and glanced back,

“Not so big after all I guess.” she hissed.

It was like match to gasoline. I grabbed her arm and pulled her back into the car.

“Ugh, Sam!” she squealed.

I grabbed a handful of hair and pressed my face to her mouth. She smelled amazing. I pressed my tongue into hers and she tasted just as good. She pressed her lips back against mine for just a second. But then her hand was on my face, pushing me away

“Geeerooffff!” she screamed, pulling away. I relented. Terrified that I must have somehow misread her. She scrambled out of the car and ran around to the front before I could release my seatbelt. I stared at her through the windshield and watched as she stopped, stood up in her all of her 5″2′ glory, legs planted apart, blouse off one shoulder, hair frayed, her chest rising and falling as she breathed heavily. She looked back at me, leaned her head to the side and raised her eyebrow again. I decided right then, I was going to fuck her regardless of what happened next. I released my belt and jumped out of the car. She turned and started running in her heels, hair flowing behind her. It took me just a few steps to catch her and grab her from behind.

“Aghhhh! Sam! Get Off!” I picked her up off the ground, pulling her toward the front door. But she was wily. Squirming, she managed to twist around in my arms and wrap her legs and arms around me she glared at me for several seconds, a sheen of sweat developing on her brow, a certain look in her eye. Animalistic arousal. Then she buried her teeth in my shoulder.

“What the? ARGHH” I yelled out more surprised than hurt. I took several stumbling steps back towards the car and grabbed a handful of hair again, pulling her loose. Pulling her head up, I returned the favor by bending my head and digging my teeth into her neck. She moaned loudly as I did but proceeded to scream as she smacked, punched and kicked me as best she could as I continued to hold her.

“God pendik escort bayan damn it Sam. Let me go!” she yelled. It was a good thing there was so much space between lots, because she was making a ruckus. I spied the hood of the car a few more steps behind me and had an idea. I staggered the few extra steps and pushed Jen off of me onto the car. She landed with a thud and I stood above her, taking in the sight.

It was surreal; the dim lights from the front of the house shed an amber glow across my manager’s body. She lay on her back on the hood of the car, propped up on her elbows, gasping from exertion. Darkness spread out beyond us. Several strands of hair stuck to her damp forehead, her eyes glinted in the light as she looked up at me. The buttons on her blouse had popped off during our struggle, exposing the lace bra I had noticed earlier in the day, her breasts almost overflowing out of them. Her skirt had ridden far up her bare legs when she had wrapped them around me, now exposing a tight matching black thong which was clearly soaked between her slightly spread legs, her shoes lay in the driveway several feet behind us. I looked down at her, breathing heavily as well, and for the first time noticed the tent in my pants created by my aching cock. I locked eyes with her.

I unzipped my pants and fished out my 8-inch member, my prized feature.

“How’s this for big?” I sneered, as Jen’s eyes bulged.

“Holy. Shit.” she gazed at my throbbing dick for several moments. Suddenly a look of genuine anxiety came over her face and I think I understood why as she stared at my girth. She started scooting away from me up the hood of the car.

“Oh no you don’t” I growled, grabbing her ankles firmly and pulling her down towards me. Continuing to resist, she pressed her knees together while trying to push me off. I grabbed her thighs and started forcing them apart. Looking down at her straining face, I could tell she realized if I won here the struggle would be over. She would be mine. Both of us were grunting from the effort, I was using all my strength to pull her strong legs apart. She resisted for what seemed like several minutes before she started to tire and I finally managed to slowly pull her legs apart. Jen’s eyes widened as I overcame her and she let out a final scream of effort as I pressed my body down onto her on the hood of her car. I pressed my now dripping cock against her soaked panties and she let out a gasp.

“Oh god, oh god, I can’t!” she moaned. Making a few final weak attempts to push me off. She knew what was coming next. I grabbed a handful of her hair once more and pulled it firmly down, raising her chin and holding her firmly in place. With my other hand I pulled her bra down roughly, finally freeing her gorgeous boobs, her nipples pointing to the sky. I wasted no time leaning over further and sucking one into my mouth, gently nibbling her nipple. With my one free hand I reach down between her legs and pulled her thong firmly to the side, exposing her perfectly smooth pussy and engorged clit. I grabbed my dick and placed it at her entrance. Jen pulled against the hand holding her hair and looked down at my bare unprotected cock, precum dripping from the tip.

“Fuck! Jesus! This can’t happen. Ohhhhhhh” she yelled out into the night.

I ploughed my oversized member into my manager. As wet as she was, there was momentary resistance as her pussy lips stretched around my girth. I withdrew slightly and then buried my aching manhood into her up to the hilt as Jen screamed out.

“Fuck Sam! Fuck! You Can’t! We Can’t!” But we could and I did, I proceed to fuck her aggressively. Pumping with long deep thrusts into her again and again. She was warm and tight, her sex hugged my smooth skin and as I slid in and out of her. The whole car shook as I pounded her into the hood. While she continued to yell profanities she wrapped her legs around me and pressed her breasts against my exploring tongue and teeth. I gave them plenty of attention before unlatching from her chest and kissing her hard. She stopped bothering to resist and moaned into my mouth and we enjoyed each other’s tongues and tastes. I marveled at how her body accepted mine, her skin blazed and her curves meshed with my body, I quickly lost myself in the rhythm and started quickly increasing my pace as I began to feel the pressure building in my cock. Jen’s moans quickly turned to screams that were absorbed by the still night air.

“Oh. Ugh! Ahhhhhhhh!” a powerful orgasm rose through her body. Her muscles tensed around me and she pulled me deeply into her with her legs still around my torso and kissed me, exhaling raggedly as my cock buried into depths rarely explored. My cock was instantly drenched in her juices and I felt myself going over the edge. As my breath caught Jen sensed the inclement explosion and encouraged it by matching my thrusts and pushing her pussy against me.

“YES! Cum inside me Sam. Fill me up! That’s an order as your manager!”

It was too much. My orgasm was volcanic. My member pulsed powerfully, shooting what felt like gallons of my white-hot sperm deep into her fertile womb. I dug into her with several final thrusts before collapsing on top of her, both of us panting.

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