Secretarial Sins Ch. 01

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When the boss wants to play, and you don't say 'No'.
1.2k words
4.13
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Part 1 of the 2 part series

Updated 06/08/2023
Created 04/14/2017
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I thought I imagined it, the first time. A slight slip that might have been someone else's touch, but was probably just my skirt shifting. I had, after all, just slipped to the floor to pick up the pages I had just dropped. Annoyingly, despite their short fall, the pages had fallen apart and spread out, so I was now on my hands and knees gathering them back up.

There it was again. A fleeting whisper of a touch. I couldn't have imagined it twice, could I? I glanced back. Nothing. My boss was stood nearby, to be sure, but he was talking to someone on the phone so it couldn't have been him. My attention returned to the loose pages.

I definitely didn't imagine it the third time. Someone, it must have been my boss, had touched me. Was still touching me, just rubbing me ever so gently. I should have turned around. Stood up. Slapped him. Something, but the tingling feeling spreading from his fingertips, prevented me even before I could move.

Instead, I moved only a little, to easier pick up the pages, I told myself. Nothing to do with how my rebellious legs wanted to part to his touch, to make it easier for him to touch me in that sensitive place his fingertips were already trying to explore.

I started to move slower, to prolong the time I would be down in front of him, on my knees and giving him easy access to prolong his gentle probing. I think my reaction gave him confidence, because he suddenly pressed harder. Still soft, but removing any doubt that any of this could be imagined. My boss really was rubbing his fingers along the seams of my underwear, through my skirt, and all I could do was kneel there and enjoy it.

His hand suddenly left me, and a moment later I let out a light gasp as I felt his fingertips brush my legs as his hand deftly slipped under the skirt and touched me just where I was starting to feel moist.

A sharp intake of air behind me told me he recognised how I was enjoying his ministrations, and he pressed harder, finally applying some real pressure to those parts that were now begging for it and I moaned. Short, and soft, but it was all the encouragement he needed. He kept up his rubbing, now pushing my knickers into my slit as his fingers sought out my pussy, and my clit.

A jolt of electricity shot through me when he found my clit, as he suddenly pressed down hard and furiously rubbed it for a second before returning to his gentle, but insistent probing. His fingers teased my pussy, pressing my panties deeper, but not yet enough to penetrate. I let out a groan that was part pure pleasure, and part frustration. This felt good, but his teasing made me want more.

I could now feel his free hand tugging the bottom of my skirt up, awkwardly, since he was only using one hand, the other still playing with my pussy and clit through my now damp panties. I heard that sudden breath again when my skirt was finally pulled up to reveal my ass, I guess he liked what he saw.

His busy hand slipped down to tease my clit some more, I could feel his fingers pressing through my knickers to engulf my clit in the fabric as he tweaked it, drawing a sharp gasp from me, but then he started to massage me between his fingers and I could suddenly think about nothing else.

So much so that I nearly missed his free hand start rubbing my ass, and slip under my panty line. That hand slipped down, and for the first time in all of this, I felt real, skin on skin contact as his fingertips just touched my pussy, just for a moment, before retreating back along my panty line and my ass cheek.

I found out why a moment later. He hooked his fingers into my panties and dragged them to the side, so first my ass, then my pussy, were on display for the world to see. His fingers left my clit and slipped back to dip one, then two fingers into my wet and willing pussy. I let out a groan and arched my back as I finally felt penetration, resisting the urge to press back onto them further.

I wasn't disappointed with my reward for patience. With a practised hand he started to finger me. He set up a steady rhythm of one, two, or occasionally three fingers thrusting firmly into me. Every so often, he would pull out completely, and rub my clit or ass with his now wet fingers.

Then, while he was still fingering me, his other hand touched my clit and started to rub it. A moment later, I realised that the finger on my clit was far fatter than any finger should be, so I glanced down, between my legs.

I saw his cock, the tip gently kissing my clit, rubbing against it before pulling back for a moment and repeating. I hadn't even noticed him getting it out. I wanted it. I couldn't help myself, I started pushing back onto his fingers, trying to push them deeper into me. I really wanted to feel that cock inside me, but his fingers were already there, so I reflexively tried to ride them to higher pleasure.

He indulged me for a moment, reaching deep inside me and fingering me a little harder, but then he stopped and pulled out. The bastard. But that was when I felt the warm solid rock that was his cock touch me again. Starting from my clit, it slid up to my pussy where I waited eagerly for it to enter me, but it didn't. I let out a low groan. This one was mostly frustration.

I didn't have to wait long though. It seemed his eagerness was as much as my own as he thrust into me, instantly filling my wet and willing pussy. His hands came to rest on my hips, and for a moment I could feel his fingers were damp with my juices, but then my attention was dominated by his next thrust into me.

That's about all I was aware of for the next little while. I'm not even sure how long. The steady piston driving deep into me, his repetitive thrusts hard, but tender. At some point during it all, I pulled my blouse open, and my breasts out of my bra so I could play with my nipples to provide a counterpoint to the pounding in my pussy.

After a while, another feeling started to intrude on the pleasure. It began quietly, a slight nagging in the corner of my being, but it quickly started building. As it did, it became more demanding, driving me to thrust back onto my bosses cock harder as he thrust into me. We quickly gained our rhythm, getting faster, and harder.

A sudden spurt of hot and sticky cum filled my pussy as he came, driving deep into me as he pumped what felt like gallons of cum into me, triggering my own orgasm which had now been building for quite a while.

I tried to keep it quiet, wasn't entirely successful, as my legs began to quiver and my pussy started to convulse around his still hard cock, squeezing his cum around his shaft as mine mixed with it. But by that point I had stopped caring or noticing anything. I was away on my own little cloud of bliss.

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