No Mercy Boss
This is a work of fiction and all characters are over the age of 18.
'Seriously you're fucking useless, I don't know why I even hired you. Every single time someone fucks up, you're the culprit.
You know fucking what? This time you're not getting away with this'.
She gets out of her seat and walks over to me. I'm shaking with fear at being berated by her.
Little did I know this was going to be a painful lesson learned the hard way.
No mercy style…….
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I had been working on the project team at my company of employment for over three years now. At 35 I had taken an internal promotion from processing admin to working on a project team responsible for various business acquisitions. My boss was based in another city in the US and his boss was based in my office. So when we had deadlines looming she was very much a profanity laden presence in our office. It was always hectic and you got thrown very much in the deep end and told to sink or swim.
My boss (a male) very much liked to exert some power and pass off blame to those working for him whenever things went wrong. Fair enough most of the time it wasn't his fault but when this happened his boss Jennifer or Jen for short usually stepped in and handled it.
Jen was 15 years older than me at 50. She was short and chubby and very much preferred to shout and bark out orders with a deluge of swear words aimed to drive home her point. At 5ft tall she was a full foot shorter than me but like every male and female in the workplace we had a fear of pissing her off.
Well today was an unfortunate moment for me. I had compiled a spreadsheet of data incorrectly based on sheets presented to me by my boss. Instead of admitting it he told Jen it was my responsibility to check it was correct. I didn't do that as thorough as I should have done and for the third time during the project run I was the person responsible for taking the blame. And boy was I in trouble.
'Marc, come with me please', Jen beckoned me over to her. She walked in front of me as we went to an empty office conference room way over the other side of the building. There were refurbishments going on and no one was anywhere near this area working. The perfect opportunity to have a shout and no one would be witness. Or so I thought.
'Take a seat Marc', Jen said as she closed the door behind me. I didn't know it at the time but she had locked the door to prevent me escaping and had taken the key.
She walked past me and I noticed she was wearing a pair of her famous brown knee high flat boots. The rounded toe and thick leather were skin tight against her large calves. She was wearing leggings and a normal silk shirt. She sat down opposite me and took out a long pair of leather gloves from her bag. She put them on and they went all the way to her shoulders. Now I knew I was in deep shit as she never put gloves on when giving me a grilling before.
'How do you manage to fuck up three times in a week Marc? I mean it's not fucking hard is it? If you did your job properly I wouldn't need to sit here with you would I?'.
'I'm sorry, the data was given to me wrong', I feebly replied.
'Seriously you're fucking useless, I don't know why I even hired you. Every single time something fucks up, you're the culprit.
You know fucking what? This time you're not getting away with this'.
She gets out of her seat and walks over to me. I'm shaking with fear at being berated by her.
Little did I know this was going to be a painful lesson learned the hard way.
'Take off your pants and underwear…..NOW', she shouted emphasising her power over me. I slowly do as I'm told completely in disbelief.
'Sit back down Marc and spread your legs. Make sure your balls are visible'.
I realise I'm about to be hurt by her and I begin to beg her to reconsider.
'Jen, p-p-please don't do anything. I'm sorry I truly am', I beg her.
'Marc I'm about to make sure you truly are sorry'.
She walks over to me and slowly places the sole of her left boot over my balls. Her size five boot sole searching for the right mixture of coverage over both my balls before slowly applying pressure.
She then begins to press down on my balls once she has found her sweet spot.
'Oh fuck, Jesus, Jen, please stop, please', I wimper as the pain starts sending a crescendo of messages to my brain of panic and pain. I began feeling cramps in my stomach and bile in my throat as I had the overwhelming urge to be sick. Jen was aware of this as this wasn't her first time so she kept the pressure firm at the same strength until she felt I was over the initial wave of sick and cramping.
'Fucking hell Jen, stop, this is abuse', I cry out in pain.
'Shut the fuck up, why do guys always fucking moan and complain', she menacingly snaps back at me.
I hadn't realised why she used her left boot from the left hand side but now she positioned herself at a point where she was able to reach around the back of my head and clamp her right hand over my mouth. Now she had me gagged and she decided to ramp up the punishment.
'I'd like to introduce your balls to my boots Marc. I do hope you appreciate what I'm doing to you here. Because it serves a purpose. Now look at my boot while it crushes your worthless balls'. Without hesitation she pushes her weight down even harder on my balls and I begin frantically screaming in vain into her gloved hand. She begins laughing slowly knowing I was being tormented by her with very little effort on her part.
But I made one fatal mistake yet again. I pissed her off!
'Marc, why the fuck are you hard? Are you some sort of sicko who gets off on being punished by me?', she lifts her boot off my balls and her hand off my mouth, and stands in front of me awaiting an answer with her hands on her hips.
'N-n-no J-j-jen. I have a boot fetish', I finally say when I have the strength to reply.
'You're fucking joking. Well if you fucking cum whilst I'm doing all this, you'll wish you hadn't. That's a fucking promise', she angrily retorts.
Jen looks at her phone which is ringing and sighs. 'Okay this call is important. Lay down and shut the fuck up', she stuffs my underwear into my mouth and answers the call. I lay down on the floor and spread my legs. I'm shaking in fear and pain. My balls have begun to swell and although I'm still hard I am scared of what is to come next.
Jen sat down in the chair I had just left and positioned herself so my legs were both sides of the chair legs. Her boots were resting on my balls. She then started grinding my hard cock into my stomach. Her grinding intensified when she got angry with the person on the call with her and eased off when she won her argument. I couldn't take much more of this and I knew I was getting closer to the edge. Without warning she stopped grinding my cock and started swinging her foot back and forth aiming solely at my now throbbing cock. Each kick thundered into my cock with unnerving accuracy. I was now beginning to groan softly into my gag. Jen raised her eyebrow at me as she watched the expression on my face.
As she came to the end of her call I was about to blow my load. Or so I thought. As she put the phone down she grabbed me by the hair.
'Get the fuck up onto your knees and keep them spread as wide as you can. I'm done being nice', she meant it as well.
She shoved the chair out the way and took a step back. She did a few practice swings and looked me in the eyes. 'Keep your hands on your head, unless I tell you otherwise'. I did as I was told.
**SLAM, THUD, SLAM, THUD, SLAM, THUD, SLAM, THUD, SLAM, THUD**
Her ten kicks with her left boot were deadly on target and I was screaming into my gag in agony. After the last kick I lurched forwards slightly and she pushed me back instantly.
'I'm impressed. Not many can take my kicks', she laughed. 'Now this time you're going to take ten from my stronger boot. But at the end of the tenth kick you'll hold my boot in place until I say otherwise. Don't worry I'll count them for you aloud', she smiled sweetly at me.
**THUD one, SLAM two, THUD three, SLAM four, THUD five, SLAM six, THUD seven, SLAM eight, THUD nine, SLAM ten**
I then quickly hold her boot in place against my balls. I'm in absolute agony. These ten kicks were twice as strong, or at least felt like they were, than the left boot kicks. My cock was rock hard against the front of her ankle. My balls were now feeling the strong thick brown leather of her knee boots. I could just about feel her foot crushing against my balls.
Jen lifts my head up so I'm facing her. 'Now for the slaps Marc. Brace yourself, don't worry I'll be using these hands on your balls soon enough', she laughs again at her threat. Once again she starts with her left hand.
'Oh and keep that boot right where it is against your balls'.
**SLAP, SLAP, SLAP, SLAP, SLAP, SLAP, SLAP, SLAP, SLAP, SLAP**
Each slap stung the right side of my face viciously. And without much of a break she issues one final instruction before using her right hand.
'This time hump my boots Marc. Just slightly though. And I'm going to keep slapping until you cum this time. And you WILL cum Marc', she demands.
She begins slapping my face hard. After about twenty slaps my face felt numb. She was so quick slapping me it only took her half a minute to give me that many. But I was lost in a painful abyss of having my balls still crushed by her unmerciful boot and my cock rubbing against her ankle. The thickness of the leather and the perfect fit of her boot meant there were no creases to the boots. My balls slowly rocked back and forth against her boot. I'm slowly being edged toward climaxing and her slaps are still raining down against my face.
For a woman so small she was stronger than I thought. As I slowly got closer to the point of no return Jen issued her final instruction. 'Marc, hump harder…..like your job depends on it, because it fucking does'. I took her instruction and began humping fast and hard. Her slaps carried on increasing in speed to match my humping.
I couldn't hold on anymore. As Jen yanked my head down and continued her slaps I was allowed to look at her tiny but powerful brown knee high boots as I came to the magic moment.
I cum all over her boots, the stream just never felt like it would stop. I had completely covered her ankle and the top of her foot.
'Well, well, well Marc. I must say that felt fun for me. But that does unfortunately present a problem for you. You best lick up your filth whilst I come up with a suitable punishment for your blatant disregard of my boots'.
I was scared but immediately began licking her boot clean of my cum. After about five minutes of cleaning her boots she instructed me to lay on the floor again.
'Lay on the floor and lift your legs up', I do as I'm told and she grabs both legs and suddenly stands full weight on my cock and balls with both her boots. I'm still gagged and scream inside it whilst she fidgets to get comfortable.
She takes her sweet ass time and once she's in place she tells me what will happen next.
'I've decided you'll keep your job on one condition. And it's non negotiable. You will become my stress reliever. Your balls will now be my property. To use as I see fit inside the workplace, and outside the workplace. Do you understand and accept?', I nod at her slowly trying not to show her how desperate I was.
'Excellent I knew this would be a perfect arrangement. Now stop struggling and stay still. I'm going to spend the next half an hour ordering loads of new boots'. I began crying as the pain was now overwhelming me.
'Don't worry Marc, once I've ordered the boots I'll continue your punishment. After all I've not introduced your balls to my gloves yet have I?'. She started laughing again as I whimpered into my gag, not knowing how long my punishment would last.
And to make matters worse, I was rock hard again……