The Lawyer - A Findom Tale Ch. 03

The rest of the day is uneventful other than the constant reminder that I'm wearing a chastity cage each time I shift or move in my seat. I did however draw up a contract for Mistress Lexi to be paid each week as a consultant and since I didn't want anyone else to see it I had to do all the administrative things that go along with that myself.

As the day draws to a close Jenny pops in, I assume to tell me that she's leaving. I get a sense she knows what's going on as she asks me how I'm feeling.

I need another $20, I'm going out with my girlfriends for drinks after work," She demanded.

Not sure why I didn't put up more resistance, instead I simply pulled out my wallet to give her another $20 today. It started to feel normal to pay my secretary whatever she asked for, similar to how I've been conditioned to do for Mistress Lexi. She of course had this "better than me" attitude despite me being the boss and making probably 8 to 10 times what she made. As she leaves she turns her head to say,

"Good boy."

There's that word again, it's a trigger for me usually causing me to get hard. But the difference now is I can't get hard due to this cage on my dick. But the attitude and the "good boy" comment has my head spinning. I've never been attracted to Jenny, not because she isn't good looking because she definitely is. More because of our age difference and the positions we held in the company she felt more like a young niece to me.

But now all I could think about is how good she looked in that skirt and how demanding she is becoming and how that is now a turn on for me. I had 2 women in my life controlling me from different angles, my client and my secretary. They both had this sex appeal about them that kept drawing me in deeper and I had no control over how to stop it (if I even wanted to).

The next day I texted Miss Lexi that I drew up the paperwork but I needed her to sign them to make it official. I was to pay her $2500 per week just because she told me to, she would do no work for the office but would now be on our payroll as a "consultant".

"I'm busy today, just give the paperwork to Miss Charlotte and I'll pick it up from her tonight," Miss Lexi responded.

I didn't like the idea of involving Jenny in my twisted fetish despite her already realizing she could demand money from me at will. But this was a whole new level, this wasn't $20 for gas, this was $100K a year salary towards a client. Which by the way is ironic because she should be paying me as the client, I doubt that will ever happen now.

"Mistress Lexi, I'd rather not involve Miss Charlotte, can't I just drop them off at your place?"

There was no response for around 10 minutes but felt like hours. Did I get myself in trouble again and would I receive another punishment? As much as I started to enjoy the punishments I knew they were only going to get more severe each time I earned one. And this cage on my dick was a good example of that as I got great pleasure sending her my hard earned money. You could say I was hooked, like a drug addict after getting high a few times. My high was from giving away my money to a hot woman who demanded it from me.

It was clear that I was neck deep into this situation but truthfully I was having the best time in my life. After all these years I found my calling, it was to pay Mistress Lexi money, money she deserved in my opinion. Not to mention the thrill I was getting from giving it to her. I only wish I could cum, despite my dick not being hard my mind was aroused (if that makes sense). I never did ask her how long I have to keep this chastity cage on, as much as I wanted to ask her I also dreaded the answer. Would she make me keep this on all week? I don't think I ever went that long without cumming. Seriously, I'd either had a girlfriend, a wife, or I would masturbate, all of which meant I was cumming several times a week, sometimes even every day.

Finally I heard my phone buzz, it was Mistress Lexi's response.

"Do you have a learning disability? Or are you just stupid? When I tell you to do something I expect your response to be Yes Mistress."

I stare at my phone not knowing what to say back. I guess I could seal the paperwork into a manilla folder so Jenny wouldn't know what's inside.

"Yes Mistress," I finally texted back.

I buzz Miss Charlotte but there's no answer. She must be away from her desk, maybe in the restroom or something. I wait another 15 min and buzz again, still no response. I decided to get up to go out to her desk, I could leave the manilla envelope on her desk with a post-it note. As I reach her desk I see Claudia walk by and ask her,

"Have you seen Jenny lately?"

"I think she went home, I saw her with her stuff heading out shortly after lunch. She didn't let you know?"

"Oh, that's right, I remember now," I say in an effort to hide the fact that I didn't have a clue.

Instead of leaving the envelope on her desk for anyone to see, I decided not to leave it on her desk but instead went back into my office to text her.

"Hi Miss Charlotte, when will you be back?"

"I'll be in tomorrow sometime," She texted back

"Did you take the afternoon off? I don't recall knowing you were out."

"I needed to go shopping."

That didn't answer my question I thought, but what was I going to do? She often works late when I need her to so allowing her to sneak out early was normally fine. But this felt like a power play, she was testing me. I knew if I didn't hold my ground she would walk all over me from this point on. Yet, I couldn't bring myself to challenge her and simply texted back.

"Okay, see you tomorrow."

And then I remembered why I was looking for her, I needed to give her the paperwork for Miss Lexi. I didn't want to get in trouble if the contract wasn't in her hands so I texted Jenny back.

"I have something that needs to get to Miss Lexi, she said you might be seeing her tonight. Can I meet you somewhere to hand it off?"

"Commonwealth Mall, be here in 15 min outside Nordstroms."

It's hard to pick up tone in text messages but I did know Jenny was winning the power play and that was clearly an order and felt non-negotiable.

"OMW," I texted.

I grabbed my keys and hustled for the elevator. Of course with my luck Claudia saw me and asked,

"Leaving early today Terry?"

"I'll be back in 30 minutes, I need to run an errand," I explained.

The mall was a little less than 15 minutes away so I needed to hurry up. I pulled in with a minute to spare and navigated to the Nordstrom's main entrance. I didn't see her so I parked in front with my hazards on. Then I saw Jenny coming out the door but she didn't approach my car, instead she stood right inside the door and gave me a look of impatience. It was obvious that she wanted me to walk to her instead of the other way around. At this point I couldn't worry about the power play, I just needed to give her the paperwork.

I jumped out of my car and headed towards the entrance.

"Can you please give this to Miss Lexi, it's important papers regarding her case that's time sensitive?" I lied.

"Fine, but I'm logging this as overtime because you are asking me outside of work hours to hand deliver this to a client."

Taken aback by the boldness all I could say was,

"Oh definitely, I really appreciate you doing this for me."

Jenny turned to leave without saying anything else. It happened so fast that I didn't have time to think that technically she is supposed to be working and not out shopping. And that handing off paperwork to someone she was going to see anyway didn't constitute much effort and certainly not overtime. It wasn't worth a debate, for the amount I pay her it wouldn't mean a lot of money and if she hadn't done it I would have had to get a courier which would most likely cost more.

That night I had a hard time falling asleep, the chastity cage was uncomfortable and what made it worse was the fact that my dick kept trying to get hard while I replayed the events from the day. Normally when I have difficulty sleeping I jack off and that usually helps falling asleep.

Then I had a crazy thought, I grabbed my phone, opened Venmo and sent Jenny the $500 I owed her. This would be my substitute for masturbating, I should still get a sexual arousal from it, not the same as cumming but the next best thing according to the circumstances. Of course she didn't know anything about it, at least I didn't think she did, and I could spin this as a thank you for taking the paperwork to Miss Lexi.

In the comments section I wrote, "Thanks for handling the paperwork, a little something to show my gratitude."

I had this good feeling come over me, similar to the feeling you get when you do something special for someone that is down on their luck. Like when I gave $50 to a homeless woman who used to stand on the corner outside our office trying to sell newspapers to make ends meet. I always bought a paper from her and always tipped... the paper was $2 but I always gave her $5 and said keep the change.

But of course there was one significant difference, neither of these women, Lexi or Jenny, were down on their luck. Also, I didn't voluntarily give them money, it was the result of being told to do it. I didn't break a contract, or lose a civil lawsuit, I was simply handing over money because they "asked" for it. Truthfully, it was all voluntarily, I could have ignored it without any consequences, but I was addicted to this level of sexual gratification, it was unparalleled to any feeling I've ever had before. It was a "high" that I wanted to experience over and over again.

I couldn't deny it any longer, I was a simp and more specifically, a finsub slave. Mistress Lexi already had me hook line and sinker and I was resigned to the fact that I was her slave, her financial slave actually. The only question left to figure out was if I was going to be a finsub to Jenny as well. There was a slightly different feeling when thinking about submitting to Jenny, the sexual gratification was heightened because I was giving money to my administrative assistant which was taking it to a new level of degenerate.

Submitting to Mistress Lexi you may say is a more natural Mistress / Slave relationship. She was a Dominatrix and did it for a living, most men who have any "relationship" with her are most likely knowing what they are getting into. I assume she views it as a business relationship, and speaking from my experience, the sub thinks of it as a sexual relationship despite there not being any sex involved. For the sub like me, it was this intimate connection with someone who understands my deepest desires, and can push my limits taking me to places I didn't even know existed.

There was a lot to figure out but I wasn't going to solve it tonight, I needed to sleep and by sending that money to Jenny I felt a calm euphoric feeling come over me which helped me fall asleep.

The next day I got there early, partly because I got up energized but also I wanted to avoid seeing Jenny when I came in. I still hadn't figured out how I was going to approach this situation. I really felt like I was at a crossroad, how I responded to Jenny today would ultimately decide which path I was to follow. One path has me continuing as her boss by keeping it professional, while the other path would send me to a place where I submitted to her, basically turning into her financial slave. Since this was all new to me I wasn't even sure I could have 2 mistresses, were slaves monogamous? It was obvious Mistress Lexi had multiple slaves, in fact, that is how she ended up in my office in the first place. Maybe belonging to a Mistress was a way to force me down the "I'm still the boss" path. I wondered if I should ask Mistress Lexi about this? It would be an awkward conversation to say the least and I'd probably earn another punishment as a result.

Being a lawyer I was used to the chess match of battling prosecutors in the courtroom, maybe the best move was to do nothing. I'll wait to see how she acts around me and then figure out my next move. Then I heard who I figured was Jenny right outside my office arriving to work. Granted it was 90 minutes late but for now I wasn't going to worry about that. It was game time and I needed to see where this was going.

I get up to walk out with the intention of casually saying good morning while heading to the restroom.

"Good morning Miss Charlotte, thanks again for taking those papers to Miss Lexi."

"I got your payment via Venmo," she said and then added quietly...." good boy. "

Because I was walking past her desk I wasn't positive if I heard that last part right, did she just say "good boy" to me? It was kind of under her breath and I was further away by that point I couldn't be sure. I hope I misheard her as that was definitely an indicator she wanted me to go down the path that made me her sub.

I felt my dick try to get hard in my cage as I processed what I thought she had said. Did she say payment via Venmo? I presented it as a gift but she viewed it as a payment as if I owed her money. This was going south quickly.

I really did have to piss so I went into the men's restroom, unfortunately with this cage on I had to sit like a girl to pee, I found that out the hard way when my piss splashed everywhere previously. I was feeling more and more like a girl instead of a man, I peed like a girl, I was submissive like a girl, everything evolved around my Mistress like some girl in love would do for her man.

But I was no man, what guy would willingly give away his money to someone just because they demanded it, and what guy would allow a woman to put his dick into a cage to let her control his orgasms? It was becoming clear that I was no longer a man by society's standards nor Mistress Lexi and apparently Miss Charlotte too.

I'm sitting in a stall pissing and thinking, should I say anything to Jenny on my way back to my office? At least she acknowledged that she received the $500 I sent. I imagined what was going through her head when she got it. Was she expecting it? Did she think I was doing it as a punishment? Did she think less of me now? She used to look up to me, she would often seek out my advice on things or ask permission to leave early for example. I had lost her respect because I was a submissive wimp and she knew she could walk all over me without consequences.

Despite losing her respect it really wasn't that bad because I was getting an emotional high from sending these ladies money. What would it feel like being a financial slave to my own secretary? These thoughts only made my dick hurt as I was getting excited but my cage wasn't allowing me to get an erection. All this wouldn't be that bad if I could just get some sexual release from these "punishments".

I washed up and headed back to my office, my plan was to play it cool like I didn't hear her "good boy" comment, which I still wasn't 100% she even said it. It could just be my mind playing tricks on me, afterall, without cumming it had my mind spinning.

As I passed by Jenny's desk I could see she was on her phone, I stopped to ask her when and who my next appointment was but she just continued texting and staring at her phone, basically ignoring me. She had to know I was standing there, I cleared my throat to let her know I was waiting to talk to her. Still she was engrossed in her phone and I started to feel stupid just standing there like a lost puppy, I mean, I was the boss. I thought back to when I first graduated law school when I worked for a big law firm, if my boss was standing at my desk I would drop almost anything to see what he needed.

Finally I started to head back into my office, I gave a hand gesture signaling I would swing back by when she wasn't busy. Again, that would normally be something an employee would do if the roles were reversed, they would come by later to see me. Was that a power play? Was she testing me to see how much she could push me? Either way I wasn't ready to face this decision of which path I should take as it related to Jenny.

The rest of the day was pretty normal, Jenny wasn't as attentive as she typically was, I did get the sense that she had been talking with Mistress Lexi about me. Was Mistress Lexi mentoring her? Hmmm...that would explain a lot if it was true.

It was around 5:00pm when Jenny walked into my office, there was no courtesy knock as she normally does, or asking me over the intercom if I was available. I was standing up looking through my filing cabinet, she simply walked in, sat down in my chair at my desk.

She stared at me as if she was impatiently waiting for me to drop what I was doing to focus on her. I turned my attention towards her as I see her eyes move from me towards the chair in front of my desk. She was telling me to sit just with her eyes. Like a dog I went and sat down and gave her my undivided attention.

"I deserve a raise, I'm thinking of an additional $1000 per week would suffice."

That would be doubling her current salary, 100% raise? That's unheard of but I wasn't in a position of power to negotiate. Even the fact that she was on my side of the desk added to her leverage she had over me. Plus, this was more of a demand instead of a negotiation, she didn't leave any doubt about who was in control.

I feel myself stir inside, the feeling you get right before you get hard, but obviously with the chastity cage on my dick that wasn't going to happen. But it didn't change the internal feeling, why was I getting excited about this conversation? I connected the dots pretty quick, the fact that she was ordering me to give her a raise is causing me to feel this way. I not only received pleasure from paying my mistress money but I clearly was liking the idea of giving in to my own secretary. Just like with Miss Lexi, it felt like this is my purpose in life, to give her my money just because she told me to.

But what could I do? It was becoming more evident that I was going to be serving her next. I reluctantly agreed to her demands, actually, it wasn't reluctant at all, it was fulfilling my deep down desire to submit and serve her.

"You drive a hard negotiation but you earned a raise so yes, let's increase your salary by $1000 per week."

"This isn't a negotiation, those are my terms. Plus, I want an admin to handle the work I do, which will free me up to run the office."

An admin for my admin? That made no sense but then again, nothing about this situation made sense. My secretary, to be more reflective of the times they were no longer called that, its administrative assistant, or sometimes executive assistant when they worked for the CEO, like in her case. So my administrative assistant just demanded a 100% raise and wants her own administrative assistant to do her work.

As ridiculous as that sounded it was indisputable that I'm being forced to decide now which path I was to follow. This certainly felt like the point of no return, if I give in and agree to her demands she would know that she had the control and being her boss was merely only in title.

She stared right through me, unreadable, I stared back but finally broke free and looked down towards the floor, a sign of submission. When I looked back up she had a slight grin like she knew she won and that I would submit. And she was right, I had no more will left in me to fight it.

"Okay Miss Charlotte, we'll get you an administrative assistant," I said as I looked back down to the floor in defeat.