Miss Cat Is In Charge

Chapter One: Intro and Set Up

[This is a set up for the story, not much going on just yet. Finding my "voice" with the intro right now]

It was already a long day before I arrived at the restaurant. Typical chain location with burgers and steak. I ordered a tall beer, a boring domestic, and told the waitress to please wait as I was waiting for the other party. My anxiety was off the charts, hoping the beer would calm some nerves. I wasn't sure what to really make of this entire ordeal.

I took a long sip of my drink. As I placed it down on the coaster, I caught the waitress approaching the table. "Here's your table. Can I get you something to drink?" She was addressing my ex-wife, Caitlyn, and handing her a menu as she took off her coat and sat down across from me. The table was for two, in the middle of the room. When I got a call from her earlier in the day while at work, I agreed to meet with her only if it was in public. She wasn't exactly what I would call a problem or someone to draw attention to us, but as far as exes go, I always like to play it safe. We are not exactly friends anymore, nothing horrible happened to cause it, we just drifted and went our separate ways about 3 years ago. The call came out of the blue when she asked if she could talk to me about something. She was very adamant that it was important, so I hesitantly agreed to a chat over drinks or dinner. She chose the place, I got there early and texted her that I got us a table.

She ordered a whiskey on ice and me another beer, how nice of her I thought sarcastically. I then rethought about the beer instead of shots.

"Alright, so what's the big issue going on that needs us meeting up like this?" I looked at her in her eyes, dead on, knowing she was probably in need of money or something. During our time together she was a train wreck most of the time. Hoping job to job, or without one at all for months at a time. She was usually calm and nice but always in need of me pulling more than my own weight around in the relationship. We moved in together after the first year mostly because we both wanted to split rent, but that ended up not happening and we grew apart quickly with her freeloading for the place to stay, food, general everything.

"Well, as you may have seen on social media, I'm single again." She had a fake sad face while sipping her drink. I don't follow her online, and she knows that. She continued. "So, I am now broke again and in a jam."

I took an extra long sip this time before speaking. "Listen Caitlyn, I'm not with you anymore, I'm not helping you out, forget it."

Her face turned from a fake sadness to a smirk. She swished the ice around in her drink and looked straight at me. "Well Mark, that is why you are going to have no choice in this matter. Well, you DO have a choice I guess, but I'm sure I know which one you'll pick. Why else would I bother asking you?" She smiled some more and signaled to the waitress for another round.

I sat upright at attention. "Go on..." I was curious to say the least. This will be a waste of time I said to myself."

She took her phone out and placed it on the table. "Mark, when we were together, you remember all the sexual fun we had. All the things I let you do in return for you going along with some of my fun ideas?"

I looked at her for a bit, kind of realizing she was getting at blackmail of some sort. "Yeah, we had fun, we BOTH did, what's your point?"

"Marc... maybe I'm not being direct enough." She turned the cell to face me. "Most of the time I had others take the pictures, sometimes my camera was hidden though. It didn't take much effort to sort through what I needed. Well... maybe some time, but well worth it. Do you think your friends and family would like to see these?"

I moved the phone closer to me as she remarked. "Don't worry hun, I have plenty of copies. Go on, scroll through." She sat back and laughed a bit while drinking.

I went through the photos and videos. I expected some nudes, maybe fucking, even when she took a strap on to me, but she had more than I thought. The times we had threesomes and although I didn't do much with the other men, the photos told a different story. My mind raced ahead of all the different things I had done with her and her 3rd party she would bring from time to time. The guys I was naked with, me allowing her girlfriends to sometimes piss on me, peg me, call me names. My entire body was out there for all to see.

I'm a VERY quiet, shy, personal person. I don't enjoy others seeing me even in my underwear, let alone fully naked, and certainly not with others.

"What do you WANT exactly Caitlyn?" I asked her with a tone I use for my dog when I'm upset and firm about my voice.

"You hun, just you. All to me, for whatever I want. You move in, and do as request, when requested. I need my bills paid somehow and I think you'll do JUST fine." She was talking to me as if she had this planned out. Of course she did. She must have spent time on this instead of just finding a job.

"Caityln, you can't just think I'll move in with you and do what you want. I have a job, a life, a girlfriend..." She cut me off quick.

"Had Marc, you HAD a girlfriend." She took her phone back. "You see, I already took the pictures I had of you dressed up that night Jen came over. You remember, don't you? She said you could fuck her if you dressed up in her clothing for a bit. She didn't even fuck you after that, but oh boy did she take a lot of pictures." She was referring to one of her coworkers and friends she invited over for drinks one night. Things got out of hand and before I knew it, I was fully dressed in her clothing, even had makeup applied. She didn't fullfill her end of the agreement, which was bad enough, but she still had the photos? Caityln continued. "You see Marc, your girlfriend used to work with Jen at the coffee shop a few years back, she still keeps in touch. When Jen told her about the time you dressed up for her, she decided to embellish a bit. Your now ex-girlfriend thinks you do this all the time and is NOT at all into what she thinks is your lifestyle."

I could bore you with the details, but the next 45 minutes or so were a back and forth of cat and mouse. Some talk got a bit loud, but with the public around us, we kept reminding ourselves to keep it down as best we could. We had more drinks and just kept at it. I kept up with saying how it won't work and I'm not falling for this bullshit, and she kept coming back with more and more ways that her and her friend created an entire world of lies so deep with pictures and videos to kind of backup just enough of the bullshit that others would believe most if not all of it. She put a lot of thought into her plan. After a while of this, I gave up. She had me.

"Alright, fuck it Caitlyn, obviously this is going to stick enough to fuck me over. I get it, alright, enough. What the fuck is your plan here?" I was pissed but defeated. She pictures, my girlfriend clearly wanted nothing to do with me as she even texted me with a long rant about me lying and cheating on her, and other bullshit that wasn't true. It wasn't worth fighting over anymore.

Caitlyn flagged the waitress down. "Thank you, but we're ready to head out." She put a $100 bill on the table. "This will cover it, thank you again." She stood up and looked at me. "Let's go hun. We have a lot to do tonight."

I stood up, confused as to how I even allowed myself to have those pictures taken over the past few years. We walked side by side towards the exit. She stood at the doorway for a second and looked at me. Obviously she wanted me to get the door. "After you." I said as I held it for her. We walked outside, it was freezing outside, a cool air with some flurries that began to fall. Typical winter time in New England I thought.

Caityln looked at me and grabbed my hand. "Come with me, we'll take my car. Yours can get towed, you won't need it."

"Towed? What? I can just drive it to the house or something."

"No! We won't need it. Let's go." She basically pulled me along the cars until we got near the back with poor lighting and not many other cars around. I could clearly see someone sitting in her passenger seat. Jen, I thought to myself.

"Now this all starts now. I'll explain it all to you on the car ride home, but first, you will do as I say at all times. You wouldn't want these pics shown to anyone right?" I nodded and said "Yeah, sure, whatever."

Caitlyn let go of my hand near the back of the car. "Alright hun, lose the clothes. You won't need them anymore. And do it fast, it's freezing out. You can leave them near in the parking lot, and get in the backseat, Jens riding shotgun." She didn't even look at me as she spoke, just said what she needed to as she got into the drivers seat and shut her door.

I thought about just walking away from this. It sounded so easy in my head. But people seeing me in drag, naked with other men, pissed on by women, taking a strap on in my mouth, it was just too much. Again, I'll spare the details, but it didn't take long for me to just start my new life.

I took off my coat, a cheap one I had laying around that was extra. I wasn't dressing up tonight as I knew it only meant seeing Caitlyn. I took my wallet and keys out of my pockets, and my cellphone. I placed them on the trunk and pulled my black tee shirt over my head. At age 37 I had a decent body. Not a six pack, but not out of shape either. At 5'11" I weighed a nice 160lbs.

Feeling the frigid air on my upper body I tried to move faster. I removed my size 11 sneakers and unzipped my jeans, stepping out one leg at a time. Next were my boxers. I enjoyed the freedom of space it gave me, not tight at all. My socks finished the deal. I left them in a pile near the tree line as best I could while tossing them. I grabbed the back door handle finding it fucking locked. Of course. God, I hated this already. So petty and predictable.

"Unlock the door, Caityln!" I was pissed already and VERY cold.

Jen unrolled her window and poked her phone out just enough to take a few pictures. She rolled it up faster than I could move towards it, as if I was going to be able to do much. She was giggling inside the warm car.

Caityln cracked her window a bit. "Come over to this side, along the front, I want to see you do a nice walk for us in the headlights."

Nobody was around, and it was dark out. The lights above us were not very bright as nobody seemed to take care of the back of the parking lot.

I moved towards the front as she hit the high beams. I quickly uncovered my cock and shielded my eyes. "Stop!"

I got to her side of the car. She had the window cracked just enough to use her voice. "Now, you will address me as Miss Cat, got it!?" I said "Yes, yes of course Miss Cat, now please let me in, this is more than we agreed on. It's too cold."

"No, it's not Marc. You see, you WILL do as I say, every time, or else. This is all part of it. You don't move unless I say so. You want to get in this car, right? You will do as you are fucking told." She laughed with Jen. Jen was busy on her phone but paying enough attention to what was going on.

I continued covering myself. "Fine, fine. May I PLEEEASSEE get in your car Miss Cat?" At this point I was nearly begging.

"Remove your hands, raise them high, all the way up and on your tippy toes. Until I say so. Do NOT move or talk." She looked at Jen and Jen pointed her phone at the window and towards my now stretched body, viewing my front in full. My pubes were trimmed but still about an inch or so long. The cold air was doing what it normally does and shrunk me down. I'm already not a shower but a grower and this was NOT helping. A nub was barely visible through the pubes. Normally soft I'm about 2 inches, while hard just around 6. Being cut, just the tip was obvious right now, not much else.

Caityln unlocked the rear passenger door and told me to get in, then rolled up her window. I ran to the other side and jumped in as fast as I could. I was freezing. The hot air was on high thankfully. I recovered myself and sat still.

"Now listen Marc, we are not going to keep going back and forth every time I need you to do something. Jen here is equally in charge as well, but I do get final say. I hope you understand that. Remove your hands. You are not allowed to cover up any part of your body anymore. Jen here took some nice micro penis pictures and already sent them to your ex. If you want more to see them then feel free to break the rules, it's up to you now.

"Nice to see you again Jen." I said sarcastically. "Always a pleasure Marc." She laughed as we drove away.

The ride was a good hour as Caityln decided to take back roads upon back roads, dragging the ride out as long as she needed while explaining a few things to me. She covered the basics... basically I was now her property.

The last part came as a shock but covered her little money scheme. Any money I had in the bank was now hers, anything I owned was now hers. Future money was all hers. The future money part was interesting as she said I can not have a real job.

She pulled into her parking spot at her apartment complex. It was a nice place. The parking lot was near the back side with a decent number of cars. Being late already, nobody was outside. The walk from the car to the door would only be a few hundred feet at best. She kept the doors locked and shut off the car, turned towards me and spoke.

"Here we go Marc. This is it. No more acting up, no more back and forth thinking about anything. I say something, you do it. You don't have to wait for me to say to do something like breath or walk around, but you do not get to do much without me. Bathroom and sleep times will be determined by myself and Jen. Right now, you need to understand your new role. I need money, lots of it. I like nice things. From now on, you are going to work for ME and Jen to give me the money I deserve. Jen has set up a few people for tonight. It's not much money at such short notice, but it'll get you started, and you'll have a much better idea of your new life. Lets get inside now.

She and Jen exited the car, then Jen opened my door for me. "Lets go bitch." Jen was not very nice with her tone. As we approached the outside door to the complex Miss Cat waited for me to get the door, naked with the entrance lights on.

Jen and Miss Cat giggled as I waited for them to enter, then me as the door shut behind me. "We'll take the elevator up." Miss Cat knew the risk of the elevator stopping on any floor was pretty good. "You can try to hide behind us, but I doubt it'll matter if someone gets in, they'll see just fine."

I pushed behind them and prayed nobody would hit the button to join us. We stopped on the 5th floor and the doors opened. Luckily nobody saw us. We stepped out, me in the back, and I followed them about 3 doors down on the right. Miss Cat keyed in the door, we stepped in and let the door slam behind me and lock on its own.

"Welcome home hun." Miss Cat enjoyed saying it a bit too much. Jen went and fixed herself and Miss Cat a drink. Then they motioned to me to follow them to the living room. Miss cat put a bowl from the kitchen on the floor near the tv across from the couch that Jen now sat on. "Water, for now. Drink up, you'll need it." Miss Cat took a seat next to Jen on the sofa and they spoke softly for a bit. I got down on my hands and knees to lap up what I could without question, annoyed at this already.

/ End of Chapter One