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Chapter 20
by
caitlynmasked
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Chapter 19 - Short term to long term
When I got home, I was in no mood to talk about what had just happened. Dealing with Mr. Stirling and then following with Mr. Orpheus had just simply drained me. While I didn’t engage in the conversation, I didn’t stop Grace from complaining about it. I couldn’t exactly blame her for focusing on her own problems, but after I’d gotten out of my feminine finery, my faja Columbianas, and had slipped into some jeans and a t-shirt, I finally had to put my foot down. “Grace, look, I get it. It sucks that you’re being blackmailed. It sucks that you could lose out on some bonuses. It sucks that you could spend some nights in jail. But come on… I have to work as a fucking female secretary for a God Damned YEAR! And if I don’t play along, I don’t lose my job, some money, and spend a weekend in jail, I get sent to a hardcore federal penitentiary for hard time. I want to be a friend and help you deal with it, but I’m the wrong person to bitch to, okay?”
The rest of Saturday is silent. Grace and I don’t even discuss dinner and instead make it, eat it, and clean it up without a single word spoken.
Sunday morning, with my breast forms finally off, Grace and I sit down and can both rationally discuss what’s happened. We both start with apologies. I knew the possibilities of problems and knew I was taking a bigger risk. I can’t blame Grace for that and apologized for snapping at her. She knew that her path forward was simple, to just continue working and not talk about what had happened, where mine was upending my life until Mr. Stirling said otherwise. She can’t blame me for not being able to listen to her problems last night and apologized for snapping at me.
Now that she could talk rationally and I could actually listen, she told me the core of what was bothering her. While Mr. Stirling had laid out everything required of Mr. Orpheus and me in our group meeting, he evidently left out something from Grace’s requirement that made her outburst a little more understandable. While I was talking to Mal, Grace was on the phone with Mr. Stirling as he told her that her task was nebulous but important. She was to keep me female and happy. If I came in looking inappropriately masculine, she’d get docked. If I was overheard complaining about my job or my feminine life, she’d get docked. If someone figured out that I wasn’t female by my actions, she’d get docked. It was another layer of control as I had to present as female, convincingly, to keep Grace in good graces now as much as myself.
We started by talking about random things that were going to change in my life. While I’d be financially fine, I’d need to manage my photography business. At the very least, I’d need to rent out the studio full time. I’d need to get more comfortable clothes. I’d need new identification papers. I could use less overtly sexualized styles of… everything. My hair, makeup, outfits, nails, all less in your face sexy. Eventually we made up a list of things to change and started with the most basic. Something that would make my new day-to-day feminine life more comfortable. My breasts and my crotch.
As a testament to how well their body shaper worked, in addition to my hair, makeup, and clothes, no one in the little transgender specialty shop recognized me though they were all excited once we introduced ourselves. Grace and I kept it vague and just said that our short term plan was going to last months instead of weeks and we needed to talk more about some comfort issues.
The gaffes made sense. My panties just weren’t doing enough to keep my erections down and even though I never got hard enough to make a bulge in my clothes, it was still uncomfortable. The gaffes would keep me pressed up so tightly that I wouldn’t get nearly as hard and therefore not nearly as physically uncomfortable. They did warn me that my physical arousal would still come on, and at times I might find that arousal itself uncomfortable but that it was more of a mental issue and not a physical one.
The breast solution they had was more problematic. Glueing the breast forms on daily was making the skin on my chest red and irritated, but when we went without the glue, they moved around unnaturally because of the nipple stimulators. The easiest thing was to purchase new breast forms. But at several thousand dollars I couldn’t afford new breast forms. Maybe after saving up for a month or two, but not now and this skin problem had to be dealt with now. Grace had suggested more athletic bras that would hold the breast forms tighter to my chest, but they pointed out that the faja Columbiana’s built in cups wouldn’t accommodate being held that way and would look strange even under clothes. In addition, we were unlikely to find a bra that was both tight enough to hold the forms on steadily and not completely crush them out of shape.
The final solution sounded like it would work fine but was frustrating in its long-term effect. Instead of a daily adhesive, I could use a longer-term surgical style sealer. It made a true bond with the skin and couldn’t be removed. After between five and eight days, it would break down and come off on its own with much less irritation. Having the forms glued on my chest that long however meant a couple things. First, I’d have to get my chest hair removed. Even if it were waxed just before the forms were sealed on, the bit of hair growth would cause problems. The second problem was that even outside of work, I’d have breasts. The only breast free breaks I’d have would be once a week or so when the forms came off and I gave my skin a break for several hours. But even then, I’d have to apply lotions and creams every few hours to make sure my skin was healthy and ready to have the forms sealed back on in the morning, ready for work. MAYBE once every few months that would line up with a weekend and I could keep the forms off for a day or so, but more or less, I’d be living with these huge breasts the whole time I was working as Paris.
Without any other ideas, Grace and I accepted this solution and purchased the surgical sealant. Before we left, I’d called both the HR department and Mr. Orpheus’ cell phone telling them both that I’d need to take Monday off. Grace had also called Loops Cuts and Curls and scheduled an appointment for my first laser hair removal session. She also requested the girls’ help as I’d want to discuss new styles for my hair, makeup, and nails, hoping that they could discuss them with me while I was getting the treatment.
Monday was busy. It felt like I spent the morning turning off my Jamie life. It took me a bit to get my voice back, but once I did, I called Tyrell and talked to him about the studio. He agreed to sublet it from me entirely for twelve months. I’d pick it back up in March of next year but until then, the studio was his. I gave him the combination to the safe and told him he could use any and all of my equipment so long as it was in good condition when I came back. I even connected the landlady into the call so she could be introduced to Tyrell and accept that he’d be paying the rent for a year. She was happy enough that I wasn’t just bailing on her.
The next call was to Dad. I knew that if I had to maintain my feminine body twenty-four hours a day, I’d have to maintain my feminine voice twenty-four hours a day. That meant that soon, I’d not only find it difficult to get my masculine voice back, I’d find it impossible to do on the spot or at will. In other words, I wouldn’t be able to talk to him. So, I set the story up of my photo internship. I told him that I’d be working with a famous photographer but couldn’t divulge who it was. That working for this photographer meant a lot of travel in areas that would have very bad communication infrastructure. I promised I’d write when I could and that if I could find a way to call, I’d do that… but asked him not to worry if he doesn’t hear my voice for months at a time. Dad being dad was dubious of the entire thing until I told him the internship actually paid more than I was making in Chicago and might lead to more business for me afterward. Then he was one hundred percent on board.
I took the easy path and repeated that lie to my closest friends. Most took it well enough as we were all fairly itinerant. Ben, Sam, and Jack took it hard especially when I said that I couldn’t come out and have a ‘fair thee well’ sendoff party.
The last part of putting my ‘Jamie Life’ to sleep for a year was packing everything up. My phone, computer, and all of my masculine clothes got packed up into four boxes and put into the bottom of my closet. They were there if I needed them, but I needed room to establish my ‘Paris Life’.
The trip to Loops Cuts and Curls didn’t take as long as I thought. While Lucy worked her laser magic Julie, Luna, Selene, and Eveyln all crowded around me and discussed my new style. They were all a little disappointed, saying that I looked good in the other styles but understood why I’d want to change for a longer term commitment. By the time Grace and I left, I had even more cosmetics and hair supplies but could now go to work looking like a normal office woman and not like a bimbo secretary.
Getting my new driver’s license was surprisingly easy as I just needed a new photograph and gender designation. As my name and no other part of my life was changing it was simply filling out a form declaring myself female and smiling for the camera. No one questioned that I was transitioning to womanhood with the way I looked.
I now carried nothing that identified me as a man, and nothing was fake or illegal. Over the next few weeks, I’d stop by the thrift shops as well as Target, T.J. Maxx, and other discount stores as I’d need a full new wardrobe. Work clothes could remain the same for now, but I’d need everyday clothes as ‘Paris’ me needed to be able to go out and not look like a slut.
Work almost felt like starting over. It was clear that Mr. Orpheus didn’t know how to act around me or practically anybody else. I think it was a good thing that he was so busy with the McGregor deal as he could simply bury his nose in that and avoid everybody else. For my part, I tried to walk the line between the old slutty bimbo Paris and a part that I felt I could play over the next year. I knew I couldn’t just suddenly switch everything off, but there were things I certainly wasn’t going to accept any longer.
Frank and Thomas were the first to notice the difference as I didn’t joke around with them at all. I wasn’t rude and I didn’t tell them to fuck off, which I desperately wanted to do, but I still politely got out of talking with them. When Thomas came up beside me at the coffee machine and ran his hand down my back, I think his eyes popped out of his head as soon as my hand grabbed his wrist and twisted it. I told him in my calm voice that touching me was inappropriate per the new director of HR and that we’d just be normal work colleagues from here on out. I had a similar interaction with Frank. Ever since then, they’ve given me the cold shoulder, and I’ve distinctly heard the whispered word ‘bitch’ when they’re talking about me.
On the opposite side of that, Jennifer and Claire immediately approved of my new attitude. I was even invited to sit with them during a couple breaks and share some coffee and gossip. They must have shared what they saw with Margret as when I saw her on Thursday she smiled and mentioned that she liked the new me and that we might have a talk soon about my future with K Edison Global.
The one personnel change that I felt bad about was Darnell. I felt like I used him and gave him the most reason to flirt hard with me and now refused that kind of relationship with him. But he again proved how much of a nice guy he is by being warm, open, and supportive. Basically, he returned to our pre-flirt relationship, and he was just a good person to be around.
Friday was an eye-opening experience. When I spotted the beautiful woman walking toward my desk, my first thought was that she was a client. An important client as she was dressed in designer clothes, expensive shoes, and was carrying a bag worth at least four thousand dollars. I swear, all she was missing was a little dog sticking out of her purse to complete the ‘rich bitch’ look. When she came up to my desk I smiled and asked how I could help her. As soon as I heard her voice, I knew who she was though.
“Paris, right? Yes, you’re my husband’s new office girl. He says you’re going to stick around so I assume he’s already been in your panties? Or has he just gotten you to perform oral on him? Either way, we’re going to get to know one another as I’m his wife, Veronica Orpheus. Is he in?”
I’m so stunned by her direct, forward nature that I simply stare up at her for a moment. Only when she scoffs and says under her breath “No wonder Mal likes you, dumb as a post!” do I move to call Mal and make sure he’s okay with me sending his wife in.
It turns out that Mal’s wife is just like him. Only worse. Living as a woman for near a month has really made me hate the term bitch, but I can’t help but believe the word was made for a woman like Veronica Orpheus. She leaves the door open when she walks into his office, so I hear their entire conversation and while Mal keeps his calm, she seems to just run over him on everything. Evidently her new car, the one I helped get done quickly, is unacceptable and she wants him to take her to the Range Rover dealership next. When Mal mentions they’ll lose money returning her car since it’s been customized, she decides that he can sell his two-year-old BMW instead and keep her Mercedes. They talk openly about me with her assuming I’m Mal’s new sex plaything at work and he doesn’t correct her. They even talk about the weekend trip to Nantucket that they just took a week or so ago and that she’s still upset about the airline losing her bag. And if I read between the lines of what they say, I’m fairly sure she’s withholding sex from him because of that. Because the airline lost her bag.
When she finally leaves, she stops by my desk again and drops a set of keys on my desk. “I had this set made for you. These will get you into our home, into Mal’s city apartment, and into our vacation home in Miami. Remember, in addition to anywhere here in the office, he can fuck you in his apartment any time he wants. He can fuck you in our vacation home so long as I’m not there. And he is never to fuck you in my house. Understood?”
Evidently the last was a rhetorical question as Mrs. Orpheus simply walked off after having told half the office in her loud voice when and where her husband, my boss, and I could have sex.
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You're Not The Boss Of Me
Going undercover as a secretary backfires for poor Paris
Paris agrees to help his apartment mate Grace help
Updated on May 10, 2026
by caitlynmasked
Created on Aug 26, 2025
by caitlynmasked
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