A Work Affair: Jess and Eric

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Jess and Eric's affair begins as Eric explores all of Jess.
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"Jess, can you come into my office please?" Eric asked as he popped his head into my cubicle. "I can't figure out this spreadsheet." It was 4:45pm on a Friday as the office was almost deserted. I had just been closing down my computer in the hopes of getting out of the office a few minutes early.

I laughed and pushed my chair away from my desk. My boss Eric was a bit of a luddite. He was only 40, but had been a construction worker for most of his working life and while that made him a good project manager from the logistics side, it came with some downsides when it came to navigating his computer.

We worked at the corporate office of a midsize construction company. Eric was the primary project manager of the commercial side of the business and I managed the contracts for the projects. We had been working together for about two years and I had been more than a little smitten with him since day 1. Our was a flirtatious relationship but it had never crossed a line, much to my disappointment.

I followed him into his corner office, the door closing behind me, and found myself admiring the way his slacks shaped his ass. He was sexy. Moving to an office job hadn't made an impact on his bottom line, as happened with a number of other construction guys who moved into management. He worked out and still went on site to work with the crews and it showed. Standing 6 feet tall he was well muscled and trim and walked with a purpose.

I shook my head to try and clear my imaginings of his ass from my mind.

He sat at his L-shaped desk but pushed his chair back so I could get close to his computer. I stood in front of the computer and if he would have moved his chair forward, I would have been right between his legs. He leaned forward a little to point to the monitor.

"How do I reorder this? The supplier sent it to me all out of whack. I need to figure out when the materials are coming in so I can update our plans."

"Easy peasy," I smiled at him. "Why don't you control the mouse and I'll walk you through it?"

"Fine." He huffed a little, but with a smile. "You know I'd prefer not to learn this Jess, I'd rather you do it." He held eye contact with me for longer than I thought was really needed, his dark brown eyes staring at my hazel ones and the nerve endings in my body started to tingle. This man really did it for me.

"Yes, well, teach a man to fish and all," I laughed at him. It amused me how reluctant he was to learn anything new.

He moved his chair a little closer to be able to use the mouse and his knee pressed into the back of my knee. He didn't move or adjust his legs and the contact made the hairs on the back of my arm stand up.

"Ok, take your mouse and click on the corner cell there," I pointed at the screen. "Good, now go up to Data, and then choose Sort." He clicked, but missed the right area and the spreadsheet sorted by the wrong column.

"Damn it," he took his hand of the mouse, "you just do it." I could tell he was frustrated.

"Ok, here. I'll do it but then I will write it down for you." I reached past him to grab a notepad and I could feel my thigh length skirt ride up a little, exposing the top of my garter belt. I had taken to wearing the garter with a pleated skirt at least once a week as it both made me feel sexy but also because I had once caught Eric looking at my legs in the combo the first time I wore it to work and I wanted to encourage a repeat. That night I had gone home and imagined how his hands would feel on my ass and it was the quickest orgasm I'd had while masturbating.

"Oh," I heard him say softly. I ignored it but kept myself in this position to write down the steps as I narrated them to him, giving him more time to look.

Once finished, I stood up and gathered the courage to look at him. "And that's that," I said. His eyes were locked on mine and he had a look on his face that I hadn't seen before. He looked... hungry.

"Jess... " he trailed off, seemingly unsure of what to say.

"Yes?" I asked, softly, pressing my leg back against his. This seemed to embolden him.

"Is that... is that a garter?" he asked, tentatively at first.

I smiled, hoping very much that this was going where I hoped it was going. "Yes," I said. "I always wear one when I wear this skirt. It's more comfortable than tights."

"You know," he said slowly, "I've never actually seen one in person before. Only in movies."

"Oh?" I giggled a little, "what kind of movies feature garter belts?"

He blushed and that, in turn, emboldened me.

"Would you like to?"

"Like to...?"

"See one in person now?"

He paused, but with a smile. "Yes. Absolutely."

I was glad the office was deserted and the door was closed. I turned to face him fully, He was still seated in his office chair, legs apart, with me in between. I reached back, unzipped the skirt and let it fall to the floor. Eric let out a soft moan and shifted slightly in his seat. His pants were snug enough for me to see that he was starting to get hard.

"That is... beautiful," he said. "May I?" and he gestured with his hand.

"Yes. Absolutely." I replied and watched with excitement as he reached out to touch the lace of my garter. He placed a finger underneath a strap and ran it up my thigh. I could feel the dampness in my panties and my nipples began to ache, desperate to be touched.

"So," he asked in a steady voice, "do you have to take this whole thing off to..." his voice trailed off.

"No, the undies sit on top of the garter," I reached down and grabbed his hand, pulling it up to the top of my underwear. He put his fingers between the fabric and my skin and gently started to pull them down. I glanced at his crotch and saw how much larger the bulge in his pants had become. It must have been uncomfortable at this point.

"Eric," I said and he paused. "How far do you want this to go?"

"As far as you'll let me." He replied with a sly smile, "I've wanted this for as long as you've been here and I want as much of you as you're willing to give."

I nodded in a silent assent. "It's all yours," I whispered. "I've been wishing for this day for a long time."

His smile widened and he continued to pull my underwear down my thighs. My pussy was now on display, a well trimmed bush, and he looked up at me. "I'm glad you don't wax. I like a natural look on a woman."

I smiled back, "I showed you mine. I think it's time to show me yours." I looked at his crotch pointedly. "Besides, I think you might be a little uncomfortable like that."

He moved his hands away from my legs, leaned back a little, undid his slacks and pushed them down just enough to be able to move his cock out of his boxers. It was at least 8 inches and thick. It looked delicious and I fought the urge to get down on my knees and begin sucking immediately.

Eric brought his hands back to my thighs and continued to explore. One hand moved to play with my ass while the other gently parted my labia and moved down my slit. "Oh god, you're already so wet," he said breathily. He moved one finger and then two inside my pussy. "Fuck."

I let out a small moan. "I told you I've been thinking about this." He gently finger fucked me for a few moments and then moved his now soaking fingers to my clit and rubbed. Softly at first but with increasing pressure as I moaned louder.

I stopped moaning as he abruptly removed his fingers from my clit. "Sit." He commanded, pointing to the longer side of his L-shaped desk and he grabbed me by the hips and sat me on the edge. Firmly pushing my legs further apart as he pushed back his chair, he got on his knees. He placed one of my legs on his shoulder, which forced me to lay back on his desk and he moved his face to my clit. His tongue began to do what his fingers had been doing just moments ago and I moaned loudly.

"You taste delicious," he said, pausing momentarily from his work.

He was good at this. He licked, sucked, and nibbled my clit. Varying the speed and pressure, bringing me close to an orgasm and then backing away. It was maddening but also amazing. I was desperate to cum. He placed three fingers inside of my pussy and pumped them in and out, then brought them down to his cock and began stroking his own cock as he ate me out. His tongue replaced his fingers in my pussy and his nose was set squarely on my clit. This is what did it for me and I came hard, pushing my pussy into his face as my vaginal muscles contracted around his tongue.

He rode out the orgasm and gently pushed my ass back so I was fully on the desk and stood up, his pants falling down around his ankles. His cock, hard and glistening already with my pussy juices, was positioned right at my opening and he firmly entered me. He let out a satisfied moan and paused, enjoying the feeling, before he began pumping in and out of my pussy. I hooked my legs around his body to ensure each thrust got as deep as possible. His cock stretched me wide and I could feel the tip kiss my cervix on the deep pumps.

He put his hands on my waist for traction and continued to thrust in and out of my soaking pussy. He was staring at my breasts, which were constrained underneath my button up shirt.

"Take off the shirt," he commanded after a few minutes of fucking, and I unbuttoned my shirt as he continued pump in and out, his hips slapping up against my thighs and ass. I was glad I wore my front clasp bra today and I unclasped the bra. My D size breasts, free from their cage, bounced wildly, nipples hard. He moaned as he watchthe them bounce. "You're fucking perfect," he said and at this I squeezed my pussy muscles together in a kegel. "Goddammit," he moaned. I squeezed again and used my legs to pull him in.

He moved his hands from my hips to my tits and used them to hold himself steady, my nipples caught in between the knuckles of his fingers as he squeezed hard and continued to ram his cock into my wet pussy.

"Your cock feels so good," I moaned. "I can't wait to see how it feels inside my month."

That did it. "Oh, fuck," he cried and I could feel his cock get slightly harder as he came inside of me.

His thrusting slowed and he pulled out. "I did not want to cum that fast, but goddamn it, you are fucking sexy." He said, almost apologetically.

I smiled. "Sit." It was my turn to command and I gestured to his seat. He sat and I took my turn on my knees, eager to taste him. His cock had softened somewhat but was not fully flaccid. I could feel his cum leaking from my pussy as I bent forward to take his dick in my mouth. He moaned loudly as I placed my lips on his swollen cock head, sucking the last bits of cum from his dick. I licked up the shaft, brought the whole cock into my mouth and then deep throated him, increasing the suction as I brought my mouth back up. With this repeated attention he began to harden again and it became more challenging to fit his entire cock into my mouth. This didn't stop me, I like a good challenge, and I brought up one hand to stroke his shaft while I gave special attention to his head, licking around the edges and sucking.

I brought my other hand up to cup his balls, gently massaging as I continued to suck him. His moans increased and he brought his hand up to my head, grabbing a handful of hair and gently pulling my hair as he guided my head while I sucked.

After a few minutes, I decided he was hard enough to fuck. I needed to feel more of him inside of me. I gently pulled away and stood up, taking my shirt and bra all the way off. I stood in front of him in just my garter belt and straddled his legs, slowly lowering myself down. He held the base of his cock in one hand, guiding it in my pussy as I sat down.

As I bottomed out, he leaned forward and we kissed for the first time; it was electric and I felt it travel down to my toes. His kiss was firm and demanding, his tongue seeking out mine. His hands moved to my ass as I slowly started to ride him.

"Suck my nipples." I demanded, and he dipped his head down to my breasts. One hand moved to my breasts to bring a nipple to his mouth while the other stayed firmly on my ass. I continued to fuck him, controlling the pace to a slow but steady rhythm as he sucked, nibbled, and pinched first one nipple and then another. We moaned in unison as I picked up the pace, closer to another orgasm. He moved both hands back to my ass, pulling apart my ass cheeks and squeezing. I moaned loudly.

"You like that?" He asked, "you like it when I play with your ass?"

"You have no idea," I replied, not ready to let on that half of the time I masturbated while thinking of him was with a dildo up my ass.

He slapped my ass and I yelped "yes," I said, "play with my ass."

He smiled and smacked me again. Then he brought two fingers to his mouth and wet them with saliva; I slowed the pace as he leaned into me to give himself room to take these fingers around my body to my ass. With one hand pulling back my right ass cheek, he placed his coated fingers on my asshole. His mouth, now close to my ear, gently nibbled on my earlobe and he said "I said I wanted all of you," as he gently pushed his fingers past my sphincter and into my ass.

"Sweet Jesus," I moaned and continued to slowly fuck him. My pussy was even wetter and his lean forward put just enough pressure on my clit that between the position and his fingers in my ass, I was close to cuming.

"Just like that" I said, "finger fuck my ass."

"Oh, that's not all I'm going to do to your ass Jess," he replied. "You're going to cum on my cock and then I'm going to turn you around and I'm going to really fuck your ass. You're going to feel my whole, thick cock up your tight little ass."

His dirty talk put me over the edge and my orgasm exploded. My pussy walls contracted on his cock and I wrapped my arms around him, digging my nails into his back through his shirt.

"Fuck, YES. Oh god Eric, I'm cuming again."

"Yes, that's right, cum for me," he demanded as he continued to move his fingers in my ass.

As my orgasm subsided he removed his fingers and pulled back to kiss me. As he did so he started to stand up. His hands on my ass, he lifted me up with his cock still inside of me. He sat me back on his desk and gently thrust in and out as he reached up to take off his shirt. He was finally naked and I could see his well defined muscles in his chest and arms. He had a smattering of chest hair that ran down his abdomen to his crotch. A dark brown happy trail that I wanted to play with.

But now wasn't the time for play, Eric was ready to fuck. He lifted my legs up to his shoulders as he stood and began to fuck me in earnest. His thighs slapped against my ass and I could feel myself moving backward along the desk due to the force of his thrusts. He noticed this as well and slowed. He stopped, pulled out and pulled me up, kissing me firmly before turning me around and bending me over so my ass was open to him.

He stood there for a moment, caressing my ass. Then he smacked it hard, twice, and spread my ass cheeks. Positioning the head of his cock against my asshole, he slowly pushed in. His cock was well lubed from my pussy and both my juices and his cum from before had slipped down into my ass crack, so I was ready for him. As the head of his cock pushed through, I caught my breath. It wasn't painful, but the pressure was intense. He paused, "Are you ok?"

"Fuck yes I am," I replied. "I need you inside of me. Fuck me, Eric."

"Yes ma'am." And he slowly but steadily pushed the rest of his cock in until he was balls deep inside of my ass. He paused for a moment, giving us both time to adjust and enjoy the sensation before he began to pump in and out of me. He started slowly at first, but picked up the pace as my moans showed him I was enjoying this ass fucking.

We were silent except for my moans, his grunts, and the slapping sound of his hips smacking up against my ass. Occasionally he would take a hand off of my waist to spank me, hard, and I would cry out, but the dirty talk ended as we got to the business of fucking.

He leaned over a little to fuck me deeper and grabbed a handful of my hair. Gently but firmly pulling, he slowed and exaggerated his thrusts, his balls slapping up against me as every time he bottomed out inside my bottom.

"Yes, oh god Eric, yes," I cried as I came for the third time, my pussy walls contracting and I could tell he could feel it inside of my ass. This must have been too much, because I could feel his cock get just slightly more engorged as he started to cum inside of my ass. He let out a loud grunt as he pumped his hot jizz inside my rectum.

He let go of my hair and stood fully, slowly pulling his softening cock out of my asshole and slapping my ass one last time. I could tell I was going to have some bruises where he had kept spanking me and I was going to very much enjoy the reminders of this encounter.

I stood as well and turned. "Wear that combo more often he said," as he pulled me in toward him; this kiss was more tender, but still hungry. I wasn't sure how I knew, but I knew this would not be the last time I fucked my boss.

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AnonymousAnonymous3 months ago

Good premise.

But sex just happens. No tension. Nothing that must be overcome.

No teasing.

Three stars.

CthulhusButtercupCthulhusButtercup3 months ago

Very nice story with some amazing visuals!

CthulhusButtercupCthulhusButtercup3 months ago

Beware anonymous comments condemning illiteracy that concurrently contain typos.

orbnatsorbnats3 months ago

I really enjoyed this story and I see that it is your first submission. Well done! Please write another anal-centric story — soon!

AnonymousAnonymous3 months ago

Congrats on your first story. There were a couple of grammatical errors that does not bother me but I brought it up because some readers will be sure to point them out, some harshly, so be ready. Overall, it was good and I hope you will lengthy your stories but that is me being selfish. Best with your writing.

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