The Deadline

Fucking Deadlines! I had been working on this project since William assigned it to me two months ago and had made only marginal headway and the due date was three weeks away. I work from home; less distractions than the normal office setting, and it allows me the opportunity to work odd hours when inspiration strikes.

This morning, William called.

“How is the tracking software project coming along?” he asked without any small talk.

“It is coming along but I won’t be able to make the due date, I’ll need at least another 2 months to get it working,” I replied with as little emotion as possible.

“Do you understand the concept of deadlines? I need to see what you did so far, mind if I drop by after work tonight to get a real view of the project?” he queried.

I had met William twice before. He was a consultant on two of my previous projects and provided good insight however as project manager he was quite overbearing. He was not able to make realistic timeines when discussing projects with clients.

I wasn’t enthused about him coming to my house, but at least it was on my ground and not his.

“Fine but if you are coming to bring me at least a good coffee. I’ll expect you at 4:30 or 5.” I hung up before he could respond.

I spent the rest of the day prepping to brief him then closed my laptop. I stepped into the shower and washed tried to wash off the stress of the day. Since I work from home, I normally only shake my legs every two weeks, so I specially shacked them. I towelled off and did my make up, again, not something I normally do day to day.

I slipped on a nice black thong with red roses on it and some peak-a-boo lace; my most comfortable pair of underwear. Putting on the matching bra I admired my good-sized breasts Knowing that the cleavage put the men I worked with at on edge.

I put on a pair of tan nylons with the black seeming running up the back. They were my favorite and I had a feeling William was a legman. I figured I could distract him if needed. I clipped them into the matching garter belt.

I pulled on a red tartaned knee length skirt and a black sleepless button up top, making sure to keep an extra button undone to put William on edge. Finishing the outfit was my favorite 7 inch red silettos.

I walked downstairs and was setting up my laptop and some printouts on the table when the doorbell rang. He was early.

I straightened my skirt and shirt, inspecting myself in the mirrored coat closet at the entrance before I opened the door.

“William, good to see you,” I said courteously.

He was still in his work clothes, albeit without a tie. He was wearing tan slacks and a pink button-down dress shirt with a grey sports jacket. He kept his hair short but was what you could describe as “Dad-handsome”; a bit soft but still fit.

“Julie, good to see you again,” he said extending the coffee, “shall we get to work?”

I led him to the dining room and invited him to sit.

“Coffee? Tea? Something stronger?” I asked politely playing the role of a wholesome host since he brought me a coffee but nothing for himself.

“I could go for a scotch if you have any,” he asked. I nodded.

I let him peruse the papers on the table while I poured the golden liquid over a couple cubes of ice and poured some Irish cream into my coffee.

I handed him the drink and sat down at the head of the table while he sat next to me around the corner. I couldn’t help noticing how his gaze constantly fell to my cleavage and I was glad I was distracting him.

I started briefing him on the project and the troubles I was having. He sipped his scotch and nodded in what I assumed was acquisitions of my troubles; then I realized he nodded whenever I leaned in… he just trying to get a better view of my cleavage!

“So, as I said, I need at least another two months,” I concluded.

“Unacceptable! By now you should be in the Beta phase ofthe project. Maybe letting you work from home was a bad idea. Maybe too many distractions…” he replied quite tersely.

“Distractions like you looking down my top?” I interjected, “Don’t think I didn’t notice!”

“No, I didn’t even notice your cleavage,” the redness spreading on his face said otherwise.

“Maybe I need to report you to HR.” I replied, “I’m sure They would love to nail you to wall!”

“Please no, I, ughh, have already been on report once. I can’t afford another one,” he pleased.

Talking with the other women in the office had given me enough information to get him fired for inappropriate behavior. He was… hands on, you could say, with some of the interns and trainees.

“Maybe I should punish you instead?” I said standing up.

Leaning on the table I looked him in the eye, “If you do what I say, I won’t report you; you pause or refund…” I left the sentence open allowing it to sink in.

I walked over to the window and closed theblinds.

“Stand up, take your clothes off!” I ordered.

His mouth opened and he stuttered to get something out before standing up. He undid his belt and his pants, letting them fall to the floor. He was wearing tight boxer briefs which were containing an impressive bulging package. He undid his shirt and dragged it over the chair in front of him.

He stood there quietly looking at me.

“All of your clothes!” I again repeated, “That is one delay!”

He reached down and pulled his socks off then lowered and stepped out of his boxes. He cupped his cock and balls, hiding them from me.

“Follow me,” I stated dryly.

I led him into the living room and told him to sit down directing him to come upstairs when I tell him too.

I climbed the stairs glancing back. Out of the corner of my eye I noticed him staring at my ass as I went up. I realized that I had him where I wanted. It had been a couple of months since I broke up with my girlfriend and it had been at least a year since I had been with a man. I needed some physicality.

I went into the guest room which doubled as my “playroom”. I removed the skirt, top, thong and bra. I opened my closet and found my favorite leather corset. It enhanced my cleavage and was strappy at the bottom. I secured it on and looked in the mirror; I could already feel the wetness developing between my legs.

I reached into the closet and brought out a leather bikini brief with the center zipper and pulled it on. I also pulled out of the closet my toy box. Rummaging through, I found my leather flogger. It was still soft and supplies as I slapped my hand with it.

“Come here Boy!” I yelled.

I could hear his steps slowly coming up the stairs. He arrived at the door and saw me standing there in my leather outfit, stockinged legs and silettos. His mouth started moving like a fish in the water.

“Come in and stand there!” I said pointing the corner of the room. He obeyed and walked slowly to the corner and turned to face me. His hand still hiding his package.

“Here are the rules,” I said walking slowly towards him, my silettos clicking on the wood floor, “I get to do what I want, you get to do what I tell you.” I ran the end of the flogger along his jaw line.

“You hesitate, you get the flogger. You hesitate more afterward; you get the riding crop. If you are lucky, you get the paddle. Now get your hands away from your tiny cock!” I said confidently knowing it would hit his psyche.

He dropped his hands and gave me my first real look at his manhood. His penis was already starting to twitch from the blood rushing in. It wasn’t the biggest I’ve had but was impressive none the less. He took care of himself too, shaving his balls and trimming the rest of his pubic hair.

I grabbed his head and forced him down onto his knees.

I turned and walked the wing backed chair in the opposite corner and sat down crossing my legs slowly.

“Come hereand clean my shoes,” I ordered. He began to stand up, “Crawl boy!”

He crawled over to my and started to rub my shoes with his hands.

“With your tongue!” I clarified to which he started to lick them. I could tell he would be good at licking my pussy by the strength and movements of his tongue.

He slowly curled his tongue around the red heal, licking it slowly but keeping his eyes down, Almost averting his gaze. Working up to the body of the shoe he took long strokes down to the toe.

“Look at me when you clean!” I commanded.

He gazed up, his blue eyes looking helpless in this situation. I could see every time he snuck a peak lower to my corset and even to my leather briefs. The power was making my shaft wetter by the minute.

Feeling he had enough with my left foot I push him back with the toe and crossed my other leg over, having him repeat the cleaning on my right.

“Do you like working for me; for my pleasure?” I asked coyly.

“Yes, Julie,” he responded.

Feeling the power made me decide to take this to another level.

“That’s Ma’am or mistress, when we are in here! Do you understand!” I said with a raised voice.

“Yes Ma’am,” he responded.

“Get on the bed on all fours,” I ordered.

He quickly got up and moved to the bed. I went into my box of toys and got my favorite restraint; a spreader bar that I could strap his wrists and legs to.

I quickly moved to position the cuffs; he pulled away. Down came the flogger onto his ass.

“Mmm,” he moaned, apparently enjoying the contact.

“Don’t move; else you get the riding crop!” I reminded him.

I positioned the cuffs and the leg straps then attached them the spreader bar forcing his ass higher in the air.

I maneuvered my body onto the pillow in front of him, placing my moist crotch in front of his face. I reached down and pulled the zipper between my legs exposing my moist slit.

“I don’t know if you deserve to taste this pussy!” I excerpt noticing how his eyes were drawn to my shaken glistening hole.

I dipped my fingers in and drew them to my mouth tasting my sweet juices. His cock was fully erect, and I could tell he was wanting relief.

I decided to extend this torture and slapped his face while saying, “Not yet, you haven’t proven yourself worthy of cumming.”

I got off the bed and went back to my bin of toys, finding a moderately sized metal butt plug. Knowing that I had the lube in the nights stand, I strolled over fondling my favorite toy. He had a look of fear on his eyes.

I held it in front of his face, “You know what this is don’t you?”

“Yes mistress,” he nodded, “you aren’t going to use this on me, are you?”

I paused and brought the flogger down on his ass again. How dare he imply what I should or should not do.

I opened the drawer and pulled out the lube, coated the butt plug then proceeded to squirt the cold liquid down his ass crack.

He was shaking, but I was unsure if it was out of fear, anticipation or the temperature of the lube.

I slowly began to massage his asshole, gently probing a finger or two to judge his tightness and to spread the lube in a bit more.

“Ugggghhh,” he moaned as my finger entered his hole up to the knuckles. His muscles clnched but then relaxed as I found the softness of his prostrate and began to massage it lightly. His breathing quickened as I felt his body began to tense up. I didn’t want him to climax, so withdraw my fingers.

I traced his spine with the plug before positioning the tip at the edge of his asshole and began to apply pressure.

He moaned as the sphincter expanded and swallowed the plug.

“That’s a good boy,” I said moving my hand down to his balls, giving them a quick mass.

“Do you like the plug being in your ass? You like me having the control don’t you!” I said with a laugh.

“Yesss Mistress,” He answered, a quick learner.

I decided I should reward him with some pleasure and returned to the pillow. I spread my pussy lips with my right hand and grabbed the back of his head with my right.

“You will make me cum with your tongue. Won’t you?” I asked with a smile.

“I’ll try mistress.” He answered, as I forced his head into my wet pussy.

He began to suck my clip, flicking it with his tongue while sucking. I began to tremble, feeling my month-long pent-up orgasm building. He moved his mouth lower, darting his tongue between my folds, I could feel my juices mixing with his saliva running down my ass.

He moaned; the victory hitting my clip in the right spot and sending a torrential squirt onto his face, the bed and my legs.

“Lick it up; look what you made me do,” I commanded him.

He licked my legs and public area clean before I stood up and went back to the toy box.

I realized that I needed to feel more power as I found a straw-on double sided dildo that I hadn’t used in a while.

I slipped it into my wet hole and secured it with the briefs supporting straps. I squirted some lube onto it and walked behind William who was still distracted licking up my squirt.

I slapped his ass as I got onto the bed. I reached between ass cheats and grasped the butt plug and pulled it out slowly.

“MMMM,” ​​he moaned in apparent pleasure.

“Keep cleaning,” I commanded, discarding the butt plug onto the floor.

I grasped the base of the strap on and guided it to his asshole.

“Relax now… this will be fun,” I noted with a laugh and pushed the dildo into the gaped asshole.

“Ugggghhhhh,” he muttered as the length entered him. The resistance pushed the dildo into my slit too and I struggled not to moan to loud.

I continued to pump it in and out, feeling another orgasm building. I reached around him and grasped his cock. I could feel it twitching wanting to release the built-up tension.

“You want to come don’t you boy?” I asked.

“Yeesssssssss,” came the response.

I felt my orgasm building more and pulled the dildo out of both of us quickly.

I wanted to feel and taste his ejaculation so positioned myself under his cock.

Taking it into my mouth, I massed his balls with my left hand and stroked my throbbing pussy with my right. I could feel his balls draw up and his cock stiffen as he let loose with the largest orgasm I had ever felt or swallowed. At the same time my body stiffened and yet another stream was propelled out of my slit onto the floor.

I crawled out from under him and laid spent for a few minutes.

“Please Mistress, let me out of the restraints?” he pleased.

I undid the straws and stood up.

“Clean up the room, there is a towel in the bathroom down the hall. And take a shower too. Meet me downstairs when you are done,” I commented.

I left the room and had a shower and put on a thong and matching bra. Covering up with a house coat, I descended the stairs all while making sure my bra was visible between the folds.

William was already downstairs putting on his shoes, his jaw dropped when he saw me.

“I’ll see you in next week for another update. The due date is extended a month,” he said with a smile.

“Sounds good to me. I expect you will be pleased by my advancement,” I smiled back and leading him to the door.

I gave him a kiss on the cheek and slapped his ass on his way out the door.

I think our next meeting might be just as interesting.