Induction Day at Spread Legal

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Richard gets introduced to his role and co-workers.
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I got up early on my first day that Monday morning so I could get ready and make it to the office just before 9am. Not wanting to make a bad first impression for The Mistress was a powerful motivator even though there was a part of me that wanted to misbehave, so that she can stretch out my ass with her strap on once again. Since the interview I couldn't stop thinking about what she did to me, just the mere act of remembering was enough to make my dick throb and get hard. Time got away from me as I found myself distracted by these thoughts and the desire to stroke my dick. I was already 10 minutes late for my train when I snapped out of it.

"Shit!" I uttered, finally noticing the time. I hurriedly got myself dressed in my best suit and rushed out of the door to the station. Checking the train app on my phone, there was another train in 15 minutes that could get me to the office just in time. I had just made it to the platform when the train pulled into the station. Jumping on the train, I was already out of breath but happy I was going to make it in time. That was until...

"This is the conductor speaking, I'm afraid we are being held at a red signal. We should hopefully be up and running soon. I apologise for any delays this may cause in your journey." Panicking, I checked the time on my phone and my heart sank. I was going to be a couple of minutes late. If only I didn't get so distracted earlier, I would have made the earlier train and got to the office on time. I didn't have The Mistress's number nor Alice the secretary's to call ahead to explain myself either. I spent the rest of the journey concocting excuses, white lies and half truths to excuse my tardiness. Alas when the train pulled into the station I had nothing but the truth.

I had made it to the office at around 9:05, I pressed the buzzer to be let in. Walking into the reception I saw a friendly face in Alice, who gave me a warm smile. "Hi Richard!" she enthused, curling her finger around her blonde hair. "I'm glad you accepted the job role."

"Hi Alice and thanks, I'm a little bit late though," I replied embarrassedly.

Alice stood up and chuckled, "I wouldn't worry about it, now come I have orders to show you to Mistress's office."

I walked behind Alice down the long corridor, as I did I felt my eyes drawn down to her tender rump wrapped in the shortest skirt I had ever seen and watched it alluringly sway from left to right. We passed many doors including the one where my interview took place. Eventually we stopped outside The Mistress's office, where Alice proceeded to knock on the door lightly three times.

"Come in!" The Mistress had demanded from the other side of her door in her commanding voice.

"See ya later handsome," Alice said with a saucy wink. She walked back down the corridor giving me another view of her ass swaying side to side, only turning back once to blow me a kiss.

"I said come in!" The Mistress sounded impatient that time around, so without further delay I opened the door and entered her office.

Her office was a spacious area painted and wallpapered in rich tones of red and at the back of it sat The Mistress on a luxurious leather chair behind a desk of mahogany. She peered over her glasses and looked at me with an icy cold stare and spoke with a voice to match. "You're late." Like with all icy environments, I was going to have to be careful with my approach.

"You see..." I began to explain why I was late, planning on telling her the truth about how my own horniness distracted me. The Mistress, however, raised her finger to me and placed it upon her luscious lips to silence me.

"I care not for your excuse. Just see that it never happens again," The Mistress gestured to the empty chair in front of her desk. "Now sit. There is much to do before you begin your job." I nodded in silence and walked over to the empty chair walking past a giant bookcase filled with texts familiar to me from University. I felt her big brown eyes look me up and down as I made my approach. When I sat down at the desk I noticed a document titled 'Contract' sitting on my side. "Read," was her command and I obeyed without question. The contract was filled with legal jargon that to put simply reads that I consent to be The Mistress's submissive and obey, within reason, to do anything she commands of me. Any discomfort or uneasiness to do any of the 'extra' services asked of me, I can use the agreed upon safe word to end it. Almost as if it was on instinct, I picked up the pen and signed at the bottom, looking up to see her lips curl into a seductive smile. "Good boy," she said, leaning back in her chair. "Now strip."

Without question I obeyed her command. Getting out of the chair, I started by removing my jacket, placing it neatly over the chair. Shirt next, then trousers, both neatly over the chair too. All that remained for me to remove was my boxers. I put my thumb down on either side of my hips and in a smooth fashion I slid those off and kicked them away. I let The Mistress see everything this time, no hiding anything. As The Mistress got out of her chair, I noticed her thigh high, high heel black leather boots wrapped around her thick toned legs with a leather corset to match underneath her white work shirt. She grabbed a bag filled with items from her desk drawers and obscured them from my view. Walking over and positioning herself behind me, I could feel her towering over me and breathing down on my neck. Her hand reached around and applied lube evenly to my dick and balls. "Don't you dare get erect," she whispered in my ear.

"Yes Mistress," I responded but saying was easier than doing as I thought of all the naughty stuff she might have planned as she massaged my cock, somehow I managed though. Putting the lube down, The Mistress showed me a metal ring in her left hand before moving it down to my cock area. She slides one testicle in first then the other before sliding in my flaccid cock to join them and fitting the ring snuggly around the base of my cock, just behind my testicles. The sensation was odd at first but I liked it and I would take any excuse for The Mistress to touch my cock and balls. The Mistress then showed me a metal cage that was shaped just right for a cock. It was only then I knew what she was planning but I didn't object. She slowly slid the cage on, deliberately taking her time with this so she could enjoy me squirming and resisting the urge to get erect. To finish she locked it up with a bulky padlock, putting me in chastity.

"That should discourage your naughty thoughts and dirty deeds," The Mistress said, turning me to face her and teasing me by dangling the key I needed to unlock the cage in front of me. "Don't worry, you will be released at the end of the day but until then your cock is mine." She bent down and grabbed a black leather collar from the bag that read 'Assistant' in silver gems. "I had this made especially for this role," she said, putting the collar on around my neck, making sure it wasn't on too tight. Finally a black marker was pulled out and she wrote 'PROPERTY OF SPREAD LEGAL' across my chest. "Perfect, now I want to introduce you to the rest of the team."

"Should I put my clothes back on Mistress?" I naively asked.

"Of course not! They need to see you for what you are!" The Mistress pulled out a metal chain-link leash. Attaching it to my collar, she tugged to indicate that I should be following her.

Bashfully, I walked behind The Mistress as she led me down the corridor to the same empty room where my interview took place, only it wasn't empty this time. The room was full of about 10 people including Alice enjoying their morning tea. When we entered I could feel all those eyes turn and look at me, naked, collared and caged. I could hear snickering, murmurs of how cute I looked with my little cock cage and how small my cock must be as we walked to the centre of the room. "Kneel," The Mistress whispered in my ear and once again I show her how obedient I can be by getting on my knees beside her. "Ladies of Spread Legal, I would like to introduce my new assistant Richard Masters," The Mistress said addressing the room. "Now let us welcome him in our favourite way," and with that she spat on my face and it wasn't long before the others in the room queued up in front of me to add their spit.

All of them approached me in their own way. A meek looking redhead with a curvy body politely waved and said "Welcome," to me before spitting delicately on me. She was followed by an Asian lady who grabbed my hair, pulling my head back and spat maliciously near my open mouth. One by one they approached and I felt their saliva hit and run down my face.

An elegant looking lady was next. "If you ever get tired of The Mistress's strap on, come and see me sometime. I can give you something the other ladies can't." To demonstrate what she meant she grabbed my wrist and guided my hand up her inner thigh and under her professional looking skirt where I found her bulge. Seeing my surprised look, she lifted up her skirt to verify I was fondling her throbbing cock. My eyes were transfixed by it and fantasised about putting it in my mouth.

Before I could give it a stroke and a play, The Mistress slapped my hand away and turned to the Trans woman, "Jenny if you want to borrow him, you have to put in a request to be approved by me."

"I might just do that," Jenny smiled provocatively at me, "It's been a while since I have flooded a fresh fuckhole with cum." She added her spit to the collection on my face and turned away. The last one left to greet me officially was Alice.

Alice stood closer than the others, putting her crotch so close to my face I could smell her damp pussy from where she had been fingering herself this morning. "Shame your cock is locked away," Alice told me. "I want to ride you and feel you inside me right now." Alice drooled all over my face before addressing The Mistress. "Can I make a request too Mistress?" She asked almost pleadingly.

"No," was The Mistress's cold response. Alice lowered her head in disappointment. The Mistress sighed, "Unless one of the partners makes the request on your behalf." Alice smiled with glee and clasped her hands together. "No promises though," The Mistress added.

Now everyone had greeted me by covering my face in saliva, The Mistress led me out of the office insisting I walk on my hands and knees. I hear my new co-workers giggle as we leave the room each of them concocting quietly a plan for what they would do to me if The Mistress grants their request.

Back in the office, The Mistress commanded me to stand again. She removed the leash from my collar and chucked me a towel to clean myself off. "I hope we didn't scare you too much in there."

"I would have said the safe word if it got too much Mistress," I replied, finishing up with the towel, wiping the last of the saliva off my face.

"Good boy, now lets show you to your office." The Mistress opened a secret door, hidden by the bookcase. Compared to the majesty of her office though, mine was more like a storage closet with a small metal desk and tatty chair. Upon the desk sat my laptop for work use only and an intercom with two lights. "Green means get dressed because we are seeing a client," The Mistress explained. "Red is for extra duties so come as you are now: naked, collared and caged. Do you understand?"

I nodded, "Yes Mistress."

"In fact, you should just remain naked unless instructed otherwise. The only time I need you clothed is when you are seeing clients with me whether its in here or out there. Clear?"

"Yes Mistress."

The Mistress walked back into her office and over to her desk, beckoning me to join her with her index finger. "Now we have to punish you for being late this morning. Thankfully I'm kind so I will let you pick your punishment." From her desk she produced a leather studded paddle and a strap on that was bigger than the one she used in the interview. "Choose!" she demanded, holding one in each hand.

I gulped and pointed at the strap on. "That one Mistress."

"Where's your manners? Do I need to teach you your please and thank yous"

"Sorry Mistress," I replied, "That one please Mistress."

"Good boy," she teased. "Like your tiny pathetic cock it wasn't hard, was it?" I shook my head as she put on the strap on. "Now bend over my desk boy."

"Yes Mistress," I did what I was told and bent over her mahogany desk, presenting my asshole to her. I heard her footsteps as her leather boots hit the ground, the anticipation building inside me as they got louder, everyone brought her closer to me until I could feel the tip of the strap on pushing up against my tender tight hole. Her foot kicked my legs wider apart, bringing me down lower on the desk.

Appling some lube to her hands, The Mistress inserted two fingers deep into my ass. The lube felt cold, making my whole body shudder as she smeared it all inside, preparing it for the much bigger strap on.

She bent over and whispered in my ear, "Are you ready?"

I nodded, "Yes Mistress."

"Then beg for it!"

"Please Mistress, please fuck me with your strap on." I pleaded.

"You want to be fucked like a bitch?" She asked aggressively.

"Yes, Yes I do Mistress." I felt a hard smack stinging my asscheeks when her palm made contact.

"What happened to please boy?"

"Sorry Mistress," I responded, "Yes Please."

"That's more like it boy!" The strap on began its penetration, stretching out my asshole just by its sheer size.

"Oh fuck!" I screamed as I felt it enter. My hands gripped the edge of The Mistress's desk, "Oh fuck! That feels so good!"

"Oh you liked that? You must be a pathetic bitch!" The Mistress was only using a little bit for now, making me feel its girth first before slamming its length into me. My lubed up asshole helped it glide in and out. "Maybe you want more?"

"Yes please Mistress!" She thrusts more of the strap on inside making me moan loud and uncontrollably. The entire office must have heard me, if only they were watching me too, I thought.

"See boy, manners cost nothing and has great rewards." She continued to fuck me at a slow and steady pace, sliding it in and out, only thrusting more inside when she thought I could handle it. After several minutes passed I started to feel the leather harness of the strap on smacking me on the ass every time The Mistress thrusts in. This to me meant one thing: I had the entire length inside my asshole and it felt amazing.

Seeing I could handle the entire length, The Mistress fucked me faster and rougher until I was unable to think straight from the overwhelming feeling of pleasure as the strap on rubbed hard against my prostate, stimulating it and bringing me closer to orgasm. "I think I'm going to cum," I was able to mutter but The Mistress must have heard me as she immediately stopped the fucking and withdrew the strap on from my ass, interrupting my chance to orgasm.

"Not in here you aren't boy!"

I felt my ass ache and throb from being stretched but I also wanted the strap on back inside me, filling my ass up and stretching it some more. Struggling to get back on my feet, let alone being able to walk, The Mistress was ready with a chair and guided me slowly down. The soft leather on the seat felt great against my fucked asshole as I caught my breath. "Thank you Mistress." I panted.

"Maybe you aren't so pathetic after all if you can take a fucking like that, I'm almost impressed. Almost." The Mistress removed the strap on and sat down opposite me. "I suppose you have earned a break after that."

For the next hour I was able to relax and recover from The Mistress's savage yet wonderful fucking. Once the break was over, The Mistress spent the entire afternoon going over the more technical aspects of my role. The paperwork I'm expected to file, clients I need to email, etcetera. There was a strange thrill that I was doing all this professional work wearing nothing but my collar and cage, if only my graduating class could see me now, especially my ex-girlfriend, though she would probably enjoy the sight of me being degraded and humiliated by the ladies of this firm.

Five O'clock came around quickly and as promised The Mistress removed the collar and cage. "Don't get used to having your cock free," The Mistress warned, "After a couple of weeks you will be wearing this full time. I will only remove it when I have need of it."

"Yes Mistress," I replied getting changed back into my suit. It had felt like ages since clothes were last on my body despite it only being this morning.

"Congratulations. You survived the first day, I hope you'll come back tomorrow and survive another day with us." For a little while I noticed a hint of warmth beneath her cold exterior.

"Thank you Mistress."

We walked down the corridor together and said our good nights before leaving our separate ways. For the entire night I thought about that intense ass fucking and the other possible ways I could be degraded. I could not wait to start my job proper tomorrow.

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hotwillyhotwillyabout 4 years ago
Fist Day

Nice follow on to the Interview.

Heading to the next part now

Keep up the writing

AnonymousAnonymousabout 4 years ago

it will be interesting to know if the shemale started in the same position as he is in, it does sound like mistress is the lead attorney and all the other are submissive to her. it does sound like when she said not to get used to his cock out of a cage , is she going to take him home and start being a slave 24/7 ??

AnonymousAnonymousabout 4 years ago
Looks like a series in the making

It's an intense beginning to a series, can hardly wait to read about the Trans Woman having her way with the assistant.

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