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Chapter 21
by
caitlynmasked
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Chapter 20 - Trixie knows, meeting Suzy
First thing, Monday morning I got an email from Mr. Stirling. Evidently not setting up an appointment with a gender counselor hadn’t gone unnoticed and he wanted to talk with me. After getting my day rolling and then Mr. Orpheus’ day on track I waited until eight o’clock before heading down to HR.
Seeing Trixie for some odd reason relaxed me. She was always so bright and happy and willing to just make anybody’s day better. I waited in front of her desk until she finished with her call and approached when she said goodbye and flashed her beautiful smile at me. When she held up a finger and did a cute cartoon sneeze into her hand, I covered my mouth and giggled. She was like an anime character with her expression of dismay. Reaching into my bag I grabbed my mini pack of tissues and hand sanitizer for Trixie to use.
After cleaning up and returning my sanitizer, Trixie shined her brilliant smile on me, “Thank you Paris. You’re always right where you need to be, aren’t you. Speaking of which, are you here to see Mr. Stirling about your gender therapy appointment?”
I quickly glance around, making sure that no one is near enough to hear before leaning in over Trixie’s desk and whispering as loudly and angrily as I could, “HEY, I don’t need anybody knowing about that. PLEASE don’t say it out loud like that!”
Trixie, bless her heart, looked like I just scolded a puppy. She honestly appeared hurt and ashamed of what she’d done, “Oh, I’m sorry Paris. I didn’t mean to say that out loud. I.. I..”
My brows furrow as I lean in further, “Wait a minute, how do you know about it anyway. That’s supposed to be between Mr. Stirling and me and no one else.”
Trixie blushed further and looked away. In a smaller voice she answered “I’m sorry Paris, I came across your file when Mr. Stirling told me to keep it out and ready for him. When I saw on the top sheet that you were already using your medical benefits, I noted that Mr. Stirling had flagged it for the gender transition insurance rider. I just wanted to make sure all the paperwork was in place and possibly save you from getting a bill for hundreds of dollars. I promise, that’s all I intended to do!”
Looking conspiratorially around Trixie leaned toward me, encouraging me to bend forward so that she could whisper. “Did I see that right though? You’re a transgendered woman? I mean… you were born a boy? You still have your bits and pieces down there?”
From anybody else I’d take this as a very insulting and humiliating question. Especially the ‘bits and pieces’ part. But Trixie’s Bambiesque quality gave her such a sense of innocence that I took her question at full face value. She was just curious. And while it wasn’t true, it was the part I was playing and therefore had to confirm what she’d read in my personnel file. With a nod and a bit of a smile I whispered back “Yes, that’s all true. I was born a boy, am really a woman, am going through gender affirmation therapy, and still have my ‘bits and pieces’ although they’re tucked back and out of the way.”
Trixie’s eyes flowed down to my breasts then further down to just below the stylish wide leather belt. When she looked back up at me, she was blushing even more and stood up to lean close enough that I could feel her lips moving over my outer ear “God Paris that is just so sexy. I’d love to go out with you and talk more about it. Or maybe not even talk at all!”
Standing up straight I had to snap my jaw closed as my mouth was hanging open for just a moment too long. Did I just get propositioned by this extremely hot woman? By a woman that I’d never had imagined having a chance of being with as my normal self? Her smile as she took her seat and wiggled back into her comfortable place was answer enough. Yes, she’d done that!
Looking over at Mr. Stirling’s office she returned to a more professional tone and volume. “I believe Mr. Stirling is expecting you.”
Hearing someone approach behind me, I knew I couldn’t discuss this further. Instead, I just nodded and smiled before heading toward Mr. Stirling’s office. As I walked Trixie called behind me “And Paris, I’ll call you about that personal meeting when you get back to your desk!”
The meeting with Mr. Stirling was thankfully short. He simply emphasized that he expected me to set up an appointment this week with a gender counselor. He provided me with a list of four counselors that he’d already contacted and that would not only accept our insurance but could set up an initial visit this very week.
After sliding the list into my purse and telling him that I’d get it done, Mr. Stirling continued, “And Miss Beaufort, I don’t want to add more acrimony to our working relationship, but since you are procrastinating in this important endeavor, I want you to stop by my office and drop off paperwork after each meeting with your gender counselor. I’ll email you the form they can fill out. It will provide me with absolutely no private medical or mental health information but will provide evidence that you are attending and progressing with your therapy. That way I won’t have to wonder, as I have for the last week, if you are conforming to our arrangement and its required tasks. Is that understood?”
I have to **** myself to unclench my jaw and return at least a halfway decent smile to my face as I say, “Yes sir.”
When I leave Mr. Stirling’s office there are three other people waiting to see him leaving no privacy to speak with Trixie, so I head right back to my desk. When I get back, I see the form emailed by Mr. Stirling and save it so that I’ll be able to deliver it to whatever counselor I pick. After I check in with Mr. Orpheus and get him some files he needs, I’m able to sit down and call the first counselor on the list. It turns out that Dr. Susan Martin’s office can get me in that afternoon for my first appointment. Having no desire to put this off further, I take the appointment and let Mr. Orpheus know that I’ll have to leave early.
I’m reminded again that Mr. Orpheus is floundering, not knowing how to act. It’s clear he doesn’t want me to leave but all he does is fume as I tell him I’m leaving for a last-minute doctor’s appointment. To be honest, if I cared about this job and wanted to make a good impression, I’d get an appointment that worked with my boss’ schedule, especially since I maintain it and know that today is a busy day for him. But I don’t care about this job and know I only need to provide the minimal amount of effort to be good enough to not get fired for cause.
Mr. Orpheus is also undoubtedly a little more upset because he overheard me talking with Trixie earlier and it wasn’t as though I was hiding the fact that I was setting up a date with her.
Dr. Martin’s office set the appointment up for three o’clock and said I should be prepared to stay at least two hours. Once I get there and check in, I can see why. There is so much ridiculously in-depth paperwork to fill out that it alone takes over an hour. Everything from my name, address, and insurance to my physical health history and family history, and then on to less easy things to answer like my anxiety, and when I started to think about gender and changes and my firsts. My first time wearing women’s underwear. My first time putting on makeup. My first time fully dressing as a woman.
It wasn’t hard making up a gender history, a timeline of me ‘finding myself’ as a woman. What was difficult was committing it to memory as I know I’d be repeating it soon enough to Dr. Martin and would likely have to be able to reliably repeat it over and over and over. On top of that I had to try and balance a story that said I was both really transitioning, enough so that I’d be willing to work looking like I do now, but not so much that I’d want to speed up the process.
When I finally got in to see Dr. Martin I was taken aback by her age. She wasn’t much older than me. With a ‘Dr.’ in front of her name, she must have just gotten this position. I hoped that would help me, that maybe she didn’t have a lot of experience. She was very friendly and nice and welcoming. I felt like I could open up to her and I likely would have, if I wasn’t hiding the truth from her and lying through my teeth.
I found out that Dr. Martin wasn’t a medical doctor but there were several medical doctors on her team, and they’d be providing any prescriptions I needed. Her doctorate was in psychology with a specialty in gender identity. I also was forbidden from calling her Dr. Martin or even Miss Martin. She was to be Suzy and wanted to call me Paris.
We spent about forty-five minutes going over my history, basically changing my answers into a narrative story from my pre-teen years to my current situation. She asked a lot of questions, obviously wanting to flesh out my answers into my whole life’s story and some of them required answers that, in retrospect, seemed very important though I had almost no time to give them consideration before providing a response. My first answer that I mentally blanched at was when she asked my current sexual orientation. It just slipped out as it was an easy answer. I’m straight. When she confirmed what I meant, saying that I was attracted to men, I realized that of course that’s what it would mean to her since I was already telling her I considered myself a woman. A straight woman would be attracted to men.
Why didn’t I at least say bisexual?
Regardless, I now had to remember that to Suzy at least, I was attracted to men. When she asked about my sexual experiences, I tried to stay closer to the truth and simply change genders. I mentioned that I wasn’t currently in a long-term relationship and hadn’t been in one for a while, but that I liked to go out and pick up sexual partners and had frequent sex. When she asked how we utilized my penis, I was again taken aback. I immediately clamped down on my initial reaction of saying that I fucked my partners with my cock all the time. I figured a transitioning woman would want nothing to do with her male parts, so I said I didn’t use my penis.
I swear, I blushed seventeen shades of red when she nodded and confirmed, “So, you perform oral sex on your men and practice anal sex in the recipient role then, right?”
Thank God I’d been forcing a smile on my face for the past month as that’s the reaction that came up with my strong sense of humiliation. I could only nod and quietly agree that I gave my ‘boyfriends’ blow jobs and let them fuck me in the ass.
When Suzy asked if she could see more of my body so she could assess how my physical transformation was progressing I tried to push it off. She was insistent though and as I was supposed to be seeking her help in transitioning I couldn’t think of a valid reason why I wouldn’t want her to examine me. When she began, I thought I might get off easy as she started with my face. Having her so close to me was unnerving. Both because she was obviously examining my masculine vs feminine traits but also because she was very attractive in her own way. When she went back to her notebook, she wasn’t shy in telling me what she was writing down. “I see that beyond some hair and eyebrow management, you haven’t had anything done to your face. No nose work, no face lift, no lip work, no eye lift. In fact, it looks like you haven’t even had hair removal done as I could just barely see your stubble coming in under your foundation. Is that right Paris?”
I agreed that all the feminization work to my face was superficial. And as the exam went on, I had to make that agreement again and again. Even when I tried to make a stand, saying that I’d had my chest hair removed, Suzy recognized that it was done specifically for the breast forms and not for a desire to make MY chest look feminine. In fact, when we were done, Suzy was surprised that none of my body was actually changed, and all of my feminine shape came from the faja Columbianas. I didn’t know how to answer her when she genuinely asked if I liked the way I looked as I was trapped.
I couldn’t say that I didn’t like how I looked, that I didn’t like my big curves, large breasts, and exaggerated hips and ass. I’m sure she’d say that we should eliminate them, but that would immediately show everybody at work that I was wearing feminine body enhancers and was obviously a man. I didn’t want that for the next year. It was bad enough that Mr. Stirling, Trixie, and Mal all knew that I was a man. At the same time though, if I said I did like how I looked, she’d want to push me into actually changing my body to look like this.
With only a few seconds to consider, I chose the path that didn’t immediately let the full office know I was a man. “Yes, I like the way I look. I… um… I like, feel like the real me when I see me in the mirror.”
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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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