Working at Spread Legal Ch. 01

Writers note: Despite this being chapter one in an ongoing story, this is a sequel to both Interview at Spread Legal and Induction Day at Spread Legal. These are two quick one shots that introduce the main characters and the company of Spread Legal, both of which can be found on my profile.

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After coming in late for my induction day, I decided to wake up earlier for my first official day of working at Spread Legal. My ass still throbbed from the punishment The Mistress gave to me in the form of a rough ass fucking with the assistance of a big strap on, though I'm not sure if it was still throbbing because my asshole felt like it had been stretched or it wanted more. Just thinking of that ass fucking led to my mind replaying the offer Jenny, a beautiful woman with a tantalising cock who worked at the same law firm, made. She wanted a turn with my ass and fill it with her cum. Temptations grew to stroke my own cock as I pictured Jenny having her way with me. It was only through sheer willpower that I resisted and focused instead on getting ready for work and arriving early.

Before the interview I never thought I would be exploring such sexual pleasure, let alone like it but now as I walked through the front doors and to the reception desk, I find myself wanting more.

"Good Morning Alice," I told the blonde receptionist as I walked to her desk. She looked like she only just got in herself as she was in the middle of taking off her coat, revealing her skimpy outfit for today. Any clients will be sure to get an eyeful seeing her first thing entering the office. She took a look at me and smiled flirtatiously.

"Morning Handsome," she said, pushing out her petite breasts to make sure I noticed them in her pink tight low cut top. "We didn't scare you off then?"

"Not yet," I replied walking down the corridor until I found The Mistress's office. Opening the door I saw something I didn't expect to see, The Mistress, naked save for her red high heels, on top of a handsome gentleman on her expensive mahogany desk and riding his cock hard. Her brunette hair was down and messy, a far cry from the neat controlled hair in a ponytail I'm used to seeing on her.

"Hello boy," The Mistress said looking over at me, not even stopping or missing a beat with her riding.

I panicked, thinking I wondered into something I shouldn't be watching, "Sorry, didn't mean to intrude Mistress. I can wait outside if you like?"

"Nonsense boy," The Mistress paused to moan as she lowered herself back on the gentleman's cock, "Take off your clothes and sit down on the chair." Doing what she asked, I removed my clothes and approached her desk, sitting down on the chair in front of it. "No erections and no touching yourself," she strictly added.

"Yes Mistress," I told her but it was already too late, my cock began to stiffen as I watched her naked toned body ride the cock. Her busty breasts moved and bounced with every up and down movement she made, only moving more wildly when her riding pace quickened. It only took a couple seconds more for my cock to be fully erect.

"Cum in me Marcus," The Mistress told the gentleman beneath her. "Cum in me now!" Marcus just nods and thrusts his hips upward causing The Mistress to throw her head and hair back, loudly moaning. Marcus did as he was told and finished inside her. Now he had served his purpose, The Mistress lifted herself off his cock and spotted my erection despite my best attempts to hide it.

"I'm sorry Mistress," I told her with my head down.

"Even erect, its a pathetic little thing," The Mistress said venomously. "Marcus show him what a real cock is like." Marcus nods again and gets off the desk standing in front of me. The Mistress was right, even as it was losing its stiffness, Marcus's cock was still bigger and thicker then mine. "That will be all Marcus."

Marcus looked straight at me and winked, "See you around." His voice had a deep smoothness quality to it and as he pushed past me and walked away, carrying his clothes, I didn't know who I was jealous of. Him for fucking The Mistress or The Mistress for fucking him.

"He fucks guys too," The Mistress said like she read my mind. "Maybe he will come back and visit you next." She had spread her legs on her desk, exposing her glisteningly wet pussy and Marcus's cum seeping out of it. "Before we get to business and punishing you for your erection, I need you to do something for me. Clean. My. Cunt!"

"Yes Mistress." I got on my knees in front of her and started to run my tongue up her pussy slit, tasting a creamy delicious mix of Marcus's cum and her wet pussy juice.

"That's right you pathetic bitch," The Mistress moaned, holding my head closer to her pussy. "Taste the cum of a better man. You are only fit to clean me up." I carried on licking her pussy as instructed, cleaning the cum out of her like a mop. I felt her legs wrap around my head, her thick thighs squeezing me like a python trapping its prey. Escape was impossible but I wasn't looking to escape, I wanted to keep going. Even as my tongue grew tired lapping up every drop of cum from her vagina and my knees were getting sore from kneeling on the hard floor for an extended period of time, I knew I was only done when The Mistress said I was done. "We are done here." She said loosening her grip and pushing me back hard so I landed on the floor. She got off the desk, her high heels making a clicking sound when she lands on the floor. "You didn't obey me when I said no erections though, so now I guess you have to be punished."

She lifts up her right foot and places the outer sole on my testicles, placing just enough pressure so I feel a bit of the pain of her crushing them under her foot but not too much to do any lasting damage. I still cried out in pain however and looked up to see her sadistic smile when she stomped on them again and again, twisting her foot on them like she was putting out a cigarette on the ground. The Mistress released her foot off of them, giving me a moments relief before digging in the sharp heel in my scrotum. Again she was careful, only applying enough pressure to make me a feel the pain and loudly cry out. The Mistress above all else was a professional.

"On your feet boy!" The Mistress demanded and I immediately obeyed even as my sensitive balls ached from her stomping. Taking my still erect cock in my hand, she pulled out a flogger of a drawer. She teased the flogger across the shaft of my penis, creating a tickling sensation as I feel the leather fronds trail across it. However when The Mistress saw I was being soothed by the gentle tickling, she lifted the flogger up and struck down on my cock, I howled in pain. She struck again, harder this time, stinging my cock with its lashes. With every strike I gave a yelp of pain but I didn't want her to stop either, I was enjoying the stinging pain the flogger delivered with every strike. Eventually The Mistress stopped, feeling I had been punished enough and left me to marvel at the faint red lash markings on my cock whilst she got changed into her office suit.

Now that my cock was flaccid again, The Mistress was able to slip on my cock cage and locked me up. "I got you a gift too for your first official day," The Mistress said showing me a modestly sized butt plug with a metallic blue finish. "Bend over and I'll pop it in."

"Thank you Mistress," I bent over in front of her as she instructed. As I felt the plug being pushed into my asshole I let out a soft whimper. Standing up straight, the plug was quite snug in my ass and felt like it wasn't going to fall out anytime soon.

"You are to wear this all day." The Mistress instructed. "The only people who can remove it is me or another member of staff. Oh and one more thing." The Mistress showed me her phone which was displaying a big red button. Pressing it, the butt plug began to vibrate in my ass. I moaned loudly as I felt it stimulate my rectum for a short while before The Mistress turned it off. "That was only on the third setting. There are fifteen." She told me with the sadistic yet playful smirk.

With that I was sent off to my office to do some work. There was something oddly liberating working in an office naked even as my cock was caged up and a plug up my ass. The morning was productive as I emailed invoices to clients, ordered stationary for the office among other basic assistant tasks. My only interruptions came when The Mistress decided to activate the butt plugs vibrate setting. In the middle of doing an email I felt a buzz more intense than the first time, letting out a moan she most definitely heard.

A red light flashes on the intercom, The Mistress needed to see me in her office. Jumping out of my chair I walked into her office. "Make me a cuppa boy," was her demand. "Splash of milk, no sugar. Got it?"

I nodded, "Yes Mistress." And with that I headed to the break room. Water boiling in the kettle, Tea bag in the mug. Pour boiling water into mug and add a splash of milk. Easy, I thought. Don't think I will be messing this one up.

A sultry voice came from behind me. "Hello Richard." Turning around, I see that its Jenny standing in the doorway.

"Hi Jenny." I wanted to keep it short and sweet so I can go back to The Mistress.

"Have you thought about my offer?" She asked, walking up to me. "Real cock and real cum filling up your ass?"

"No," I lied even as my cock twitched in its cage. Jenny however could see right through me.

"Well think it over some more," she said smirking, knowing that I was definitely considering it. "I put in a request to The Mistress this morning." With that, she sauntered away back to her office. Shaking the thought of her pounding my ass, I put the cup on the tray and brought it back to The Mistress. Standing in front of her with the tray, I noticed her smirk and prepared for her to push the button. Without fail the butt plug vibrated again, more intense than last time. I bit my lip to stifle the moan and gripped hard onto the tray so I did not spill her tea. The Mistress was impressed.

"Put the tea on my desk and get down on front of me, I need to put my feet up." I nodded and did exactly what was asked of me. Putting the tea in front of her on her coaster so I didn't get hot liquid on her mahogany desk and getting down in front of her on my hands and knees so she could put her feet, still in red high heels, on my back. I heard her take a sip of the tea and braced myself for her criticism. "Very Good," however was her verdict, surprising me. I felt joyful at doing something right but decided not to show it so I didn't look unprofessional. For a reward, The Mistress activated the butt plug on a higher setting for an extended burst. I gasped loudly as the intensity of the vibrations made my leg quiver and my body tingle with pleasure. "How did you like setting seven?" The Mistress asked.

"I...I...li...like it Mistress," I was unable to think straight, not even processing I am only almost halfway through the settings and already being reduced to a quivering mess.

"Maybe you'll like eight better," The Mistress said, activating a more intensive vibration and leaving it on for much longer.

"F...F...Fu...Fuck!" I cried out as my ass is stimulated heavily. My moans were short and frequent as I squirmed and convulsed on the floor, tossing and turning until I ended up on my back. The Mistress decided to shut off the vibrations just as I felt myself close to orgasm and placed one of her sharp high heels lightly on my nipple, twisting it and the other pressing down on my soft belly.

"It looked like you were close to cumming, I can't be having you do that in here," The Mistress explained. "Lucky for you its break time. Be back here at two pm sharp or else." She said this while stroking the flogger, making her message clear and helping me to my feet with her strong arms.

Still recovering from the intensive vibrations that brought me close to orgasm, I stumbled into the break room which was now full of employees gossiping and eating their dinner. When I walked in the silence was palpable as I felt every eye on me. When I walked past, I heard snickering and comments about my butt plugs, bets were being made on how high of a setting I could take.

"Sit next to me Richard!" I heard Alice cry out, her hand patting the empty seat next to her. After grabbing some snacks, I made my way over and gently placed my ass on the seat. "How's your morning been?"

"Eventful," I laughed.

"Well don't skip on details," she excitedly said.

"Well first I saw Mistress ride a guy called Marcus."

"Oh I know that part, I was asked not to tell you. Mistress wanted it to be a surprise."

"Well it was!" I chuckled.

"Marcus is a good friend of the firm. On my twentieth birthday, he fulfilled a fantasy of mine, bending me over my desk and pounded all my holes hard in front of my colleagues. He ended up finishing on my face and I had to walk home with his thick creamy cum dripping off my face. I have a video of it on my phone. The only disappointment was he didn't bring his friends. There's always my twenty first though." Alice looked over at me with her inviting eyes and winked.

"The Mistress might have different ideas."

"Perhaps. But a girl can dream."

I carried on telling her about the rest of the day. Complete with ball trampling, penis flogging and anal vibrations. As I did, Alice bit her lip and pressed her knees together. Her fingers twirled around her blonde hair and her cheeks glowed red. She was, as I found out, becoming increasingly turned on by my story.

"I wish I was there so I could see it happen," Alice sighed. "Or that it was happening to me. I miss being her assistant sometimes." I was shocked when she told me that though upon reflection I didn't know why. I didn't think I was the first, after all everyone in the office was treating the fact I was walking around naked caged and plugged too matter-of-factly because they had seen it all before. Alice continued, "Some of us started that way like Stephanie." She pointed at the curvy redhead who timidly spat on my face on my Induction Day yesterday. Stephanie meekly waved back at both of us.

"Not all though." The voice belonged to the Asian lady who nearly enough pulled out my hair and spat down my mouth at the same spitting welcome ritual, her manner seemed more polite today compared to the viciousness of yesterday. "I'm Yukio, by the way." She held out her hand and I shook it.

"Nice to meet you Yukio."

Yukio sat at the table with Alice and I "Sorry about yesterday by the way, I can get really into dominating guys. That and my impressive Law degree was why I was able to skip the assistant phase."

Stephanie joined us as well. "So what was the highest setting you experienced today?" She asked with a low voice that bordered on a whisper.

"Eight." I told them, slightly embarrassed that it wasn't a higher number.

"Shit, then I guess I owe people money," Yukio laughed. "I had you down at tapping out at five."

When the clock on the wall read 13:50, I excused myself from the table and went back to The Mistress's office. I didn't want to chance being late even if I liked the thought of the flogger striking down on other places on my body.

"You're early," The Mistress said when I walked through the doors.

"I didn't want to be late Mistress."

"Such an obedient boy you can be sometimes," she said with a teasing scoff. "Very well, get back to work." I nodded and walked back into my little office and carried on with my work expecting another jolt from the plug to tingle my hole. However it never came, probably because The Mistress didn't want to make me orgasm. As I worked, sparked by the revelation that I was not the first assistant, I wondered what would happen after my contract ended. I didn't think I could be the only male lawyer on the firm and I felt like I couldn't go and work in a regular office after this with their stuffy suits and no chance of working with a plug stuffed inside my asshole or being pegged in the Boss's office. I dismissed all manner of thought relating to this, after all it seemed so far away at the time.

Five o'clock came around soon enough and the red light on the intercom flashes. "I have to tell you that you have received a request," The Mistress said as I stood in front of her desk. I knew who from before she could even say her name. "It seems Jenny has need of you." For the first time I can recall seeing, The Mistress took off her glasses. "I will state that any request can be rejected by yourself but if you do agree, I shall be there in attendance to make sure they abide by the rules and sometimes for my own pleasure. Is that clear?"

"Yes Mistress."

"With that being said, do you accept Jenny's request?" The Mistress turns the screen around and I see her request. As expected she wanted to fuck my ass, less expected was me sucking her cock/her fucking my mouth.

"Yes please Mistress." I felt my cock twitch in its cage, excited at the prospect.

"Good, I shall put you in for this Thursday Afternoon at 4pm."

"Thank you Mistress."

The Mistress pushed herself off her chair and struts toward me. She removed my butt plug first but not before teasing it by moving it around inside, all just to hear me moan again and unlocks the cage, releasing my cock. "You did good today," she whispered in my ear, her hand stroking my now free cock. I could feel it beginning to stiffen up. "Its okay, let it get hard," she reassured me as she continued to stroke it from head to base, my cock is now fully erect and throbbing. "You deserve a treat after today," her stroking pace quickened and with the other hand she unbuttoned her shirt, giving me an eyeful of her massive cleavage, "You like my tits, don't you?" She said taking a handful and giving it a good squeeze. I nodded as I could feel myself getting ready to cum from the way she sensuously stroked and massaged my cock. I was ready to blow my load and that's when she stopped and released her hand off my cock. "You really thought I would let you cum in my office?" The Mistress chuckled. "Now get out of my office and I'll see you tomorrow."

"See you tomorrow Mistress," I replied, turning to walk out the office and collected my suit along the way. As I did my balls ached and felt heavy from the amount of cum it had ready to launch. I wanted to stroke myself to completion right there but didn't because I knew Mistress would not be pleased.

"One more thing," The Mistress called out as I stood in the doorway about to leave. "Good work today."

"Thank you Mistress." I gave her a smile and closed her door. I had to get dressed in the corridor where everyone walked past could laugh at my small cock as they left home for the night. This included Jenny.

"See you on Thursday," she said, winking at me as she walked on by.

I left the building fully dressed but my balls still ached from being denied the chance to cum. Though even as I got home I tried to resist the urge to satisfy them myself despite the level of frustration I was feeling. I wanted to see how far I could take this before it inevitably erupts. However temptation soon manifested itself in a barrage of naughty images sent by Alice to my phone, revealing every sensuous part of her slender petite body including a photo of her spreading her pussy with the caption "Wish you were here?" The one that got me really horny though was the video she sent of her twentieth birthday and her 'present' at work. Watching her getting pounded hard by Marcus in her different holes with his big cock as she squealed and moaned for more made me give in and reach for my cock to finish the job but before I could lie one finger on it and stroke myself to completion, my phone vibrates again, this time it was a call and I see a name I haven't seen in a long time displayed on my screen.