Working at Spread Legal Ch. 03

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The day has come for Richard to obey Jenny's request.
3k words
4.49
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Part 3 of the 3 part series

Updated 06/09/2023
Created 02/07/2020
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My alarm wasn't due to go off for another two hours but I found myself laying in bed already wide awake on that Thursday morning. Whether it was from the anxiousness, the horniness or a combination of the two I could not say. I could feel my cock trying to stiffen up, at least as much as it could still being trapped inside The Mistress's metal cage, as I thought about what I had in store for me later on today. Jenny had booked some time to use me as she saw fit provided The Mistress and I agreed with how they will use that time and from the moment I was introduced to her she has made it no secret about what she wanted to do. I couldn't stop thinking about her cock, a real cock unlike Mistress's strap on, erect between her legs and ready to use.

If it wasn't Jenny I was thinking about it was Alice and her petite fuckable body. My phone was vibrating non-stop as she sent picture after picture, video after video of her naked body in various poses and sexual encounters with different guys and girls. If my pathetic cock hadn't been caged for the whole night I would have been masturbating furiously to them. I still looked at and watched every one she sent me even as my cock strained against its prison desperate to be free, hard and stroked.

It had not even been a week since I started working at the Spread Legal law firm and I already felt like I had learnt so much and gained so much experience and not just experience I could put on my résumé or take to any future job role but about myself and my kinks and fetishes. The Mistress had assembled something rather unique with this law firm, one that I would be sad to leave once she eventually tires of me and ends my contract. I pushed that thought out of my head however as that was months away at the very least.

It was soon time to get ready to go to work so after finishing my second cup of coffee to make up for lack of sleep I opened up my wardrobe and pulled out my suit. Putting my boxers and trousers on over my cage was a strange sensation and definitely added a substantial bulge between my legs that was bound to get some stares on the packed rush hour train that morning. Though the rush of being kinkier than they'll ever know certainly made up for any potentially embarrassing moments that may occur on the commute as a result of my cock cage.

However no one on the train was too busy browsing social media or reading the free newspaper to notice the bulge that the cage created and I arrived at my stop without anyone commenting or questioning it. There was a part of me that was a little disappointed, that no one gave me a weird look or uttered something about it. I shrugged it off and headed to the office, after all there was going to be plenty of chances to humiliate myself at work and have The Mistress punish me for it.

"So tell me did you have a nice wank to my pictures last night?" Alice asked me as soon as I set foot in the door.

"I...I couldn't."

Alice looked astonished, "Why not? Was it this Chelsea girl again?"

"The Mistress wanted me to keep the cage on last night."

Alice giggled, "Then I guess they didn't help at all then."

"Not at all but they were very hot. I could feel my cock was desperate to escape."

"Tick Tock little toy," a familiar sultry voice from said as they entered the office, approaching me from behind. I could hear her heels clicking as they hit the ground behind me. Turning around I came face to face with Jenny standing less than an inch away from me. I could feel her cool breath against my neck as she softly said in my ear, "At 4pm you will be mine to play with."

"But it's not 4pm yet," The Mistress said sternly, making her entrance from the hallway, her cold glare focused firmly on Jenny. "Until then I still got tasks for him to accomplish."

"Yes Mistress." Jenny never took her eyes off me, even when she was addressing The Mistress. "See you later little toy." She blew me a kiss before strutting off and disappearing into her office.

"My office. Now boy," The Mistress told me as her strict tone faded into one more cold and sharp. She pivoted on her high heels and strode back down the corridor to her office.

Entering the office and getting undressed in front of The Mistress had become so much of my usual morning routine by now. The Mistress, not one to beat around the bush, got straight to business. "We have a possible client coming here tomorrow from a small tech company called KittySolutions. It seems someone is looking to acquire them and they want us to represent their best interests."

"What would you like me to do?" I asked with a respectful tone. The Mistress smiled appreciatively at the fact that like her, I was also straight to business, even as I stood there naked, caged and thinking about Jenny's cock fucking me later on today.

"I want a full report on the company and its founder, Kitty Parks, on my desk before 4pm," The Mistress instructed me.

"Yes Mistress," I replied and returned to my office. I counted down the time till 4pm as I got to work completing the report. I even worked through my lunch break so I knew I would be finished in time.

It was quarter to four and I just put the final flourishes on the report and placed it on The Mistress's desk where she thumbed through out and concluding that it was, "Acceptable." I guessed she had read a lot of these to know what a good report looked like. "I suppose we should go to Jenny's office and see if she's ready. Turn around boy."

"Yes Mistress," I responded like an obedient subordinate and did as I was told. I felt a leather restraint being tied around my wrist and tightened.

"Eyes front!" The Mistress commanded when I tried to turn my head and see what was going on. I obeyed and felt a cold chain across my back as The Mistress slapped on another restraint on my other wrist. With my hands were tied behind my back I felt powerless to her every whim. The next thing she put on was a collar around my neck, the same one from my Induction Day and attached a leash to it. "Come," she said, pulling the leash.

I was paraded down the corridor, chained up and collared, for everyone to come and watch as I was being led to Jenny's office. I could feel all their eyes on me and see them whispering to each other. I would have no idea what they are saying but I have a guess its about what Jenny has planned for me and taking bets for how much I could take before giving up. Once The Mistress knocked on Jenny's door, I knew it had begun.

Jenny answered the door in nothing but black leather thigh high heeled boots. Her cock was already semi erect but not as erect as the nipples on her big tits. She beckoned us in with a gesture of her finger. The Mistress yanks the collar once more and leads me into Jenny's office, shutting the door behind us.

Jenny's office looked a bit more modern compared to the classic of Mistress's office, complete with glass tables and ergonomic leather chairs. However her centrepiece was not something you would find in most offices. It reminded me of the pommel horses gymnasts used but this was bound by black leather and had stirrups on either side for someone to rest their feet on.

"You know the rules Jenny." The Mistress told Jenny. "I'll be watching."

"Yes Mistress," Jenny said, bowing her head to her before turning her attention to me. "Well, well, looks like its playtime little toy." The Mistress took the leash off my collar and took her seat in the corner, her eyes on the both of us. Jenny continued, "Now, on your knees."

I obeyed Jenny like I would The Mistress, after all I am subordinate to everyone else who works here, and awaited further instructions. Jenny chuckled and started to smack my face with her cock.

"I bet you want this in your mouth," she teased, rubbing her tip around my lips. "taking it like a slut would. Go on. Give it a taste."

I opened my mouth and wrapped my lips around the tip of her cock. This was my first time sucking an actual cock so I was unprepared for the taste but I was instantly hooked and begun to take more in my mouth until I felt it getting harder and expanding inside.

"I think he likes it." Looking up I could see her grin down at me. "I knew you were a cock loving slut." My lips slid up and down her cock. Since this was my first time I was unable to take much of her cock in my mouth. "Oh come on, you can take more than that. Here let me help." Jenny grabbed hold of my hair with both hands and pushed more of her cock in until I was gagging on it. "See not so difficult, is it?" With her cock in my mouth, I shook my head. "Want more?" I nodded. With that Jenny proceeded to fuck my mouth hard.

With my hands still tied behind my back, I quickly lost my balance and fell backwards. This didn't stop Jenny, in fact it gave her a better angle to rapidly thrust her cock in her mouth. "Pathetic Slut!" she screamed at me as I felt the tip of her cock reach the back of my throat. All I could do was moan vigorously as saliva ran down my chin.

Jenny withdrew her cock, now covered in my drool, from my mouth and I gasped for air whilst she slapped my face with it some more. This break only lasted a little while before it was back to mouth fucking. "Before you leave here today you'll be covered and full of my cum." This was about much warning I got before Jenny's cum shot out her cock like geyser and covered most of my face. I could even feel it in my hair. "You aren't done yet," Jenny informed me pointing at the ropes of cum still dripping out of her cock. I got to work sucking her dry giving me my first taste of cum. It was saltier than I imagined but by no means unpleasant as I swallowed every drop in front of her. "Good Slut," she said patting my head, "but that was only the starter." Her eyes gestured towards the pommel horse in the middle of the office and suddenly I knew what it was for and my cock twitched in excitement.

Jenny picked me up by the arm and got me back to my feet, cum still dripping off my face, and led me to the pommel horse. Firmly squeezing my ass, she held me steady as I got on and put my leg over as it would have been difficult with my hands still restrained behind my back. Finally I was on, my feet placed in the stirrups. My wrist restraints were undone but only to lock them back up again around the handle on the front which had the effect of pulling me down too so my chest and face caressed the leather. With my tight asshole exposed, I was finally in position.

Jenny took her time building up to my anal penetration, her hands fondling my ass as a prelude to a spank. The first smack that I felt stinging my asscheeks made me loudly gasp, she spanked just as hard The Mistress and this was nothing compared to the consecutive spanks that rained down upon my ass cheeks. The harder the spank, the louder the gasp. "You are probably thinking 'why the spanks?'" Jenny said, relishing in my moans and whimpers as she grabbed my sore cheeks. Even though I was unable to see her I could feel the wicked smile she had on her face. "Well its to tenderise you before the main course."

That's when I felt the tip of her erect cock rub against my tight hole. "Beg for it. Tell me how much you want me to fuck you like a slut," Jenny demanded.

"Please fuck my ass," I begged her.

"Not good enough!" she shouted. "Beg harder!"

"Please fuck me, turn me into a cum bucket slut," I pleaded to her.

"Warmer," she said with a rich exotic tone.

"Pound me harder than I ever been pounded before and flood my ass in your cum!"

Those, it seems, were the magic words Jenny needed to hear as immediately after she heard that, she slammed the entire length of her cock inside my tight hole. I loudly screamed out as I felt my hole be stretched to accommodate her big cock inside me. Her hands gripped onto my hips as she pulled it back out, only getting halfway before slamming it back in. Her cock slid in and out of my ass with no lube and increased speed until it felt like her cock was a jackhammer, rapidly and deeply fucking my ass until I lose the power to form coherent words let alone sentences. My loud moans and whimpers must have been heard throughout the office. "You like me fucking you like this, you pathetic little slut?" Jenny yelled grabbing and pulling me by the hair.

"Y...y...yes!" I was finally able to moan. I was thankful that I was on the pommel horse with my feet in the stirrups because at the rate I was being fucked, it was doubtful I would be able to still stand up. Even caged up, the intensity of Jenny's fucking had made me cum as I felt something dribble from between my legs, spilling onto the leather.

"You filthy cum bucket!" Jenny must have saw it too and reacted by giving me a big spank and pounding my ass harder and rougher than before, I didn't think that was even possible. All I could do was just take it and grunt as my body tingled with pleasure. I know my ass would not be the same after she finished with it. "I hope you're ready," she hissed in my ear. "Because I'm going to fill you up like the pathetic cum bucket you are."

True to her word, I felt her cum flooding inside my asshole, drenching it with creamy goodness. I screamed out in pleasure, "Oh Jenny!" as I felt it leak out and drip down my thigh, I must have been filled up to the brink and then some.

"Now get out of my office!" Jenny said undoing my restraints and pushing me off the horse. I had been so used like I was nothing but somewhere she could stick her cock but I felt, weirdly enough, amazing even as my asshole felt sore and cum wouldn't stop leaking from it. The Mistress rose from her seat and attached the leash to my collar. Unable to stand on my two feet, I had to crawl on all fours, on my hands and knees, as The Mistress led me back to the office. Once again everyone came to see me being led back to the office. I could hear their giggles as they took note of me being on all fours and the cum that was still dribbling out my hole.

Finally reaching The Mistress's office, I had finally recovered enough to barely stand on my two feet. The cum that plastered my face was beginning to dry. The Mistress pushed a button on her desk to reveal a shower hidden in the wall. "Clean yourself up and take the rest of the day off." The Mistress also unlocked my cage, freeing my cock. "I suppose you have earned a break."

"Thank you Mistress." I replied and hobbled over to the shower. My knees were still weak and my asshole was still throbbing but I had recovered enough strength to move. I stood under the shower, letting the hot water wash me clean as I reflected on the hard fucking I just received. Just the thought of it was enough to stiffen my recently released cock.

Once I was finished and dried off, I got myself changed. "I got something to show you," The Mistress smirked. She led me to her computer and showed me a list of requests that had just came through from the other workers. "I guess they were impressed by your performance today." A cursory glance revealed several stuff I hadn't even tried yet but had gotten me curious and some stuff that I wouldn't even try. "We can go through them individually tomorrow. Now get out of here."

I walked down the corridor and to Alice's front desk. "Did you have a good time?" she asked feverishly hoping for some juicy and dirty details.

"Maybe I'll tell you later," I replied teasingly with a wink.

"Hmph! Not fair," She playfully pouted, crossing her arms. Underneath her act however I caught the faintest hint of a smirk. I exited the office, waving goodbye to Alice, and hopped on a train going homeward bound still feeling some of Jenny's cum inside me.

Lying on my own bed, I thought once more about Jenny fucking me and how much it turned me on. Before working at Spread Legal I never thought about any of this but now I could feel my horizons expanding and wondered what else might have the same effect. I knew the answers though would be in those new requests.

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7 Comments
LedmunLedmun6 months ago

Interesting Hope it continues

Just2KinkyJust2Kinkyalmost 2 years ago

Nice but last one was so much better.

tulsaguy113tulsaguy113over 3 years ago
More!

Please give us more of this story line...I love it!

AnonymousAnonymousover 3 years ago
Absolutely Fantastic

This is such a great series. I know you’ve been working on “Stephanie and the joys of dogging” (another phenomenal series), but I do hope you will consider returning to this one. The characters are hot as hell, the nervous yet excited view of the protagonist is perfect, and overall the quality of the writing is superb. I would simply love to read more of this masterpiece.

AnonymousAnonymousabout 4 years ago
Awesome!

Such a great series, I can't wait for more chapters. I am actually jealous of him

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