Black Box Ch. 02

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Young guy explores his dominant side with his milf boss.
14k words
4.65
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Part 2 of the 3 part series

Updated 11/23/2023
Created 01/09/2021
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You know that feeling you have sometimes, when you know something is wrong, but you just can't figure out what it is? In my case this feeling was growing as I was now working full time on developing my program. Days quickly turned into weeks and I realized that making the program invisible would require a complete redesign, and even then I couldn't be sure if it would work. I voiced my concern to Sarah but she assured me that Mr. Salvio was in no hurry. All that mattered was that I made it impossible to detect and track. Under normal circumstances this would have been a dream come true, to be able to develop my own program with little or no real deadline, but deep down I knew that sooner or later they would demand to see results. As the weeks went past, I was slowly drifting out of focus until one day I realized I had become stuck in a loop. Normally I would have been able to take a step back and look at the problems from a different angle after distracting myself with some everyday work, but now I had nothing else.

I was alone at the office most of the time too. Sarah had started to come in late in the mornings and after a week or two she started to come in after lunch. Nowadays she hardly showed up at all so I knew I wouldn't get any help there. Back before all this started, I could always zoom out for a while and watch her bubbly ass bounce back and forth as she paraded through the office, something I was really starting to miss. Especially now since she had really embraced her new look after Mr. Salvio took over. The few times I saw her, she was always wearing tight skirts and blouses, and designer heels that really showed off her impressive figure even more. She kept in touch with e-mails though, regularly asking if I was still happy with the job, and still being too afraid to back out of this deal I kept assuring her everything was fine.

But I knew everything wasn't fine. There was nothing normal about this situation and no matter how much I tried I just couldn't concentrate on the programming. Deep down I think my problem was that my mind was stuck trying to recall the feeling of Sarah's soft lips wrapped around my cock as I came in her mouth. Her head hand been in my lap and from the excitement I never really knew how much her mouth had actually been on my cock when I came. She could have stroked me to make me cum and only ever braced me with her lips, and my mind was going crazy from not knowing. At the same time, I knew that Mr. Salvio must have some serious leverage over her to make her do something like that, blowjob or not, and I knew I should feel bad about exploiting her. But the incident really left a mark on me and I eventually made it a part of my morning routine to jack off in the shower to be able to focus at all once I got to the office. No matter how weird I felt about it all, part of me kept the hope up that I would be able to feel her lips wrapped around my cock again one day.

I toyed with the idea of quitting, just to see how she would react, but I didn't want to risk piss Mr. Salvio off. After all, I had agreed to stay and work on the program, and I doubted I could back out now. It was still bothering me though. Would it work? Unconsciously, I think my mind was starting to focus more on getting another blowjob than it was on developing my program, and that is where I started to make mistakes. To compensate, I started to do more and more hours at the office but I soon realized that it would be much more difficult than anticipated to make my program invisible. I could make it difficult to detect, but Mr. Salvio made it clear that he needed it to be virtually undetectable and untraceable. As if the pressure wasn't enough already, Sarah wanted me to email her every week with any significant updates so that she could brief Mr. Salvio. This was really starting to annoy me. If she bothered to come into the office more often, she would know what I was working on and I wouldn't have to spend valuable time writing her emails. This afternoon was no different. I was stuck in a loop, unfocused, and not able to find a way forward, and the frustration was growing in me. I heard a "ding" and checked my e-mail and my head almost boiled over as I saw another message from Sarah, asking if I was still happy with the work and if I had done any progress this week.

"No!" I screamed out loud in the empty office and quickly typed in a response to her.

"No! I don't think this is possible!" I wrote and pressed Send. I stared at the screen until my eyes hurt but she didn't write back. I knew in the back of my head it wasn't normal for a boss, or whatever Sarah was these days, to ask you every week if you were happy working there. Maybe she was playing mind games to make me quit?

I was frustrated and my head hurt, so I shrugged it off and stared blankly out into the empty office space. Even I had limits apparently and I knew I needed a break. Maybe I just needed a rest. I shut down my system and went home, and immediately fell asleep. I had pushed myself hard lately and decided I deserved a good long sleep. Next morning, I skipped my normal routines and instead took a quick shower and went out for a proper breakfast. With my financial situation I rarely treated myself to anything, but today I felt I needed something different. Still, I didn't want to over spend so before splashing any money around I went to take out some cash and checked my bank statement. Just a quick glance at the statement almost made me trip over myself as I pocketed my bills. I had several thousand more than what I had expected and found that someone had made a few very hefty deposits to my account. It looked like my regular pay check but the numbers were all wrong. It quicky became clear to me this must be my new salary, and even if I should be overjoyed, I felt almost sick. With this amount of money thrown at me, I knew there would also be expectations, and there would be no backing out.

I hurried back to the office, grabbing a sandwich on the way, forgetting all about the nice breakfast I had made plans for. Once there I started up my computer and just stared at the screen. Maybe I expected the extra pressure of knowing how much they paid me now would force my brain to come up with a next step. But there was nothing. I felt a chill down my spine as I for the first time in my life was starting to doubt my own ability to solve a problem. Had I finally reached a point where I just couldn't find a way forward?

I snapped out of those thoughts as I heard the elevator arrive and Sarah emerged through the doors. She was in a knee-high black skirt, white blouse, and matching black blazer, and high heeled shoes that now made a smattering sound against the floor as she walked through the lobby.

"What are you doing here?" I mumbled, just as she came into my room.

"I thought I needed to check in on you, you were acting strange yesterday," she said with a resolute expression.

"Strange?" I asked, letting my head rest in my palms.

"In your e-mail yesterday," she said and folded her arms, "that didn't sound like you, giving up like that."

"I'm not giving up," I sighed, with my head still resting in my palms, "I just need you to understand that this might not be possible, at least not in the way Mr. Salvio expects."

"Mr. Savio doesn't respond well to failure I'm afraid," she said and started to pace in front of my desk.

"You're stuck, I get it," she continued, "but we can't tell him that."

"But I'll need more time," I said as she continued to pace, now with a more concerned look on her face.

"Maybe you should try a different approach," she tried, not sounding too convinced herself.

"A different approach?" I gasped, and raised my head in disbelief, "what do you think I've been trying to do for the last weeks?"

"I don't know anything about this shit," she snapped and waved at my computer, with an irritated look. She tapped her chin with a finger as she kept pacing.

"Of course, you don't know," I almost screamed at her, "maybe actually being here would help!"

This made her stop, mid step, and she seemed ready to scream back at me, but took a deep breath instead and frowned.

"I thought you were doing fine," she said, "I literally asked like every week if you were good," still irritated but obviously trying to calm herself.

"Well, I'm not," I sighed and leaned my head into my palms again, "and if you bothered to be here instead of distracting me with your damn e-mails, you'd known that already."

She was about to reply but fell silent as I continued, "and what about the paycheck? You couldn't tell me you're paying me a fortune now?"

"You have an issue getting paid," she said with a quirked brow, "the company is taking care of that, don't you worry. They're giving you Mr. Williams old salary."

"Yeah, but with that amount of money, I just think..." I trailed off and rested my head in my palms again and sighed, "I just didn't need any extra pressure right now, and besides when Mr. Williams gave me this job, the deal was that part of my pay check would go to some people that my uncle owes money."

"That's been taken care of too by Mr. Salvio," she said with snort, "I really thought you were doing fine." She no longer sounded angry, but it was obvious she wasn't very comfortable with the situation.

"I thought your job was to know how I was doing," I grumbled.

"Yeah, and I made all the arrangements so you could come in here undisturbed and do your thing, and I check in on you all the time," she said quickly now as if she was getting more nervous, "I thought that was what you wanted to be able to focus."

"But I'm just so damn tired," I replied with deep sigh, "and I'm, honestly, not sure I can do this."

"You listen now, very carefully," she said and put her palms on the desk and leaned in and gave me a commanding look.

"You need to get a grip of yourself and get this done before," but her words were cut short as my gaze fell from her piercing eyes to her cleavage. It was there, right in front of me, and I just couldn't help myself.

"Seriously?" she said and I looked up right at her again. There was an uncomfortable silence for a while as I sat there with a sheepish look on my face.

"You need to focus on the job here," she said.

"But I can't focus, and it's making me miserable," I sighed, and slowly sloughed back into my chair. I knew she was not the type that would care, but it felt good anyhow to let that out.

She was about to reply but hesitated and seemed to contemplate on something for a while. She looked confused, almost dazed, as she stood there leaning forward on the desk with her cleavage still right in front of my face. It took all my willpower not to look.

"So how do we get you focused?" she said, seemingly more as a question to herself. I slowly looked up and once more stared right into her cleavage. This time she seemed distracted and it looked like she didn't even notice. Even as my glance lingered, she just stood there.

"I know I can't help you with the program," she burst out suddenly, almost as if something had snapped inside her, "so tell me, what can I do to help?"

I quickly looked up at her and she had a strange but determined look on her face. I knew she was on the line here too. It was her job to make sure I finished the program, and it looked like we were both about to fail. I couldn't believe it but she just stood there as my eyes again wandered down her neck to her full cleavage.

"Am I distracting you?" she asked, and leaned even further in until her chest was basically right in front of my face.

"What are you doing?" I asked, feeling as if a jolt of electricity flew through my pants giving me an instant hard-on. My heart and mind both started to race as it seemed possible that I could feel those lovely lips again.

"Whatever makes you happy, and gets you back to work," she said, and again looked just as surprised as I did.

I was astonished. Deep down I knew it was Mr. Salvio pulling her strings somehow, and I knew it would be wrong even just thinking about using her. But she seemed so determined as she stood there flaunting her cleavage right in front of me, giving me a peculiar look. She seemed to know exactly what she was doing and didn't hesitate the slightest. She really was a stunningly beautiful woman. She wore makeup that perfectly highlighted her cute face and topped it off with her deep red lips that almost made me shiver just looking at them. I felt my cock pulsate in my pants as I slowly got my hopes up as to where this could lead.

"So, what can I do?" she asked.

"Well first," I said, "it'll help if you're actually here," as I still felt too embarrassed to ask for what I really wanted.

"I can do that," she said and stood back up now and pursed her lips into a little frown as she must have noticed my eyes admiring her shape.

"I'll help out anyway I can," she said, "I can even be nice if that's what you want," she added and gave me a quick smile.

"Let's not push it," I said and earned another smile from her, "I don't need you to pretend to be nice, as long as you..." I lost my thought and trailed off, as I couldn't find the courage to tell her what I wanted.

I was still waiting for her to lash out at me and storm out of the office, but the longer she stayed the more I gained confidence that she would actually go through with this. She still didn't move and just stared at me with a raised brow now.

"As long as I what?" she finally asked, and I felt another rush all through my body. Was she for real?

I felt my face burn red as I blushed, not knowing how I could tell her what I wanted. I couldn't just ask her for a blowjob, could I? Still, she was basically asking what she could do to make me focus on work, and considering she had already made me cum on her face once, and in her mouth once, and how she was flaunting her cleavage right in front of me, she must have known full well what I wanted. I was almost surprised by myself as I felt a surge of confidence build even though I knew this shouldn't be possible. I think it dawned upon me that she would do pretty much anything to get me back to work and my lust slowly started to outgrow my embarrassment.

"... keep me happy?" I finally said with a low voice, almost whispering.

"Yes well," she said with a raised brow, "the question is, what will make you happy?" she continued, giving me a curious look. The room was so full of tension and she must have known exactly what I wanted, but it was as if she needed me to literally spell it out for her.

"Happy," I mumbled and felt my cheeks burn red, "why don't you let me get a better look at you, and we'll find out," I started and moved my hand in a gesture over the desk.

She let out a short smirk, shaking her head and went on to gracefully remove her black blazer, folded it, and put it down on a chair. I was astonished at how she just followed my request. This was the same woman that used to go mental if someone brought her the wrong cup of coffee, but here she let me wave her around like it was the most natural thing in the world. She slowly bent forward and placed both palms on my desk, just like she had before, but with her blazer off I had a much better view down her blouse. She had a calm but determined look on her face as my eyes drifted down to her cleavage and she made no attempts to move even as I reached out and trailed the back of my hand over her chin, down her neck to her chest. I continued to let my hand wander over her chest and felt her full breasts through her blouse and bra. The feeling of the control I seemed to have over her washed away the last of my uncertainty and I instead tried to determine just what to do with her. It was so intoxicating, the way she just stood there and let me run my hand all over her. I trailed my hand up the center of her blouse and popped open first the top button, then two more, until I had room to reached further in to cup her bra clad breasts. She kept her palms still but her head started to move a bit as I groped her chest.

I continued to open a few more buttons until her blouse came fully open and traced my palm down her waist and then back up her belly to her bra where I gave her tits a soft little squeeze. With one hand on her chest, I stood up now and slowly rounded the desk until I stood beside her, and from there I let my other hand wander down her back towards her perfectly shaped ass. I let it rest just by the arch of her back, and she turned her head to look back at me.

"So, this is how I make you happy?" she asked.

"For starters," I said with an exhale and let my hand slide down over her ass and gave her a soft squeeze. She looked at me with a frown but then wiggled herself a bit closer to me and arched her back as my hand circled her butt. I felt her flinch as I grew bolder and took a firm grip and bounced her buttocks in my hand. Looking down at her from this angle, with her blouse open, and my hand firmly attached to her bubbly shaped ass almost made something snap inside me. I again felt a rush in confidence from the control I seemed to have over her.

"Damn your ass is perfect," I said as I trailed my hand down her legs and then ran my palm up the inside of her thigh, in under her black skirt, until I got myself a handful of her soft naked ass. I didn't feel any panties so I figured she must have been wearing a thong. She still just stood there, but I could feel her flinch and she turned her head back to look at me as my hand moved over her ass and I could see her red lips part and let out a soft sigh as I trailed a finger in between her cheeks. Just as I suspected I could feel the soft fabric of her thong and I just couldn't help myself from sneaking a peek at it. Reluctantly I took my hands off her soft ass and reached down to grab the hem of her skirt and pulled it up over her full ass. I had watched that ass countless times, parading through the office, and now I had it right in front of me, covered only by a think black thong.

"Mhm Mrs. Williams," I said, "do you always wear a thong?"

"Only when I'm in a skirt or tight pants," she answered calmly.

"I always imagined you were," I said and let my palm circle both her cheeks and then let a finger slide along her thong again, down to where I must have trailed over her pussy.

"Do you know how long I've wanted to get a proper look at your ass Mrs. Williams?" I asked, and felt my arousal grow even more, as she seemed perfectly fine with me running my palm all over her ass. I gave her a light slap as she didn't respond, and from the way she flinched at first, I almost got scared I had gone too far, but she just looked back at me, with a confused and almost embarrassed look on her face.

"I'm aware that it draws attention," she said with a low voice that ended with an exhale as I gave her another slap over her ass. Digging my fingers into her flesh I could see her lips part again to let out a muffled sigh. She arched her back even more and leaned her chest down towards the desk as I gave her a few more slaps over her ass, loving how it wiggled from the impact. I didn't even know I had this in me, but I just loved how she arched her back and curled her lips into a slight frown every time my palm bounced against her ass.

"You always did love showing your ass off around the office, didn't you?" I asked, astonished by my own bold words.

"It keeps attention away from elsewhere," was all she replied with a slight sigh, as I let my palm dig into her flesh one more time, giving her a firm squeeze.

As much as I loved having my hand all over her ass, I knew I needed more, as I could feel my dick ache in my pants. With almost all my inhibitions gone and how she seemed so willing to make me happy, I knew it was time to finally feel those lips again. And this time, there would be no doubts if her lips where on my cock or not. She followed me with her gaze as I let me hand trail up her side and I moved back around the desk until I stood in front of her. She leaned up on her palms again and tilted her head to look at me and with my new found confidence I let a hand casually run down her open blouse again to squeeze one of her bra covered tits. The other hand, I let trail up her neck to gently stroke her soft chin. I planted my palm on her cheek and let my thumb move in a circle over her soft red lips and I almost started to shiver as I could feel the tip of her tongue brace against my thumb as she reached out to wet her lips. She must have picked up on my arousal as she gently parted her lips and sucked the tip of my thumb into her mouth, letting it circle her soft tongue.