Lady in the Night #1

*Knock knock*

???: Good evening, sir,

CEO: Come in!

???: Is it a good time for you, sir?

CEO: Ah, Andy. I see you're dressed in female attire now. Excellent!

Cindy: As you instructed, sir. You can call me Cindy while I'm in this attire.

CEO: What time is it, Cindy? Aren't you worried that a colleague might discover our little secret?

Cindy: It's already 10 PM, sir. Everyone has left the office, so there's no need to worry. That's why I changed.

CEO: I see. I must say, I quite like your female outfits. Blouses and tight skirts suit you better than your usual loose-fitting male clothing.

Cindy: Thank you, sir. That is because I have to wear loose-fitting male clothing to hide my feminine features. I've been dieting and exercising for months to achieve a more feminine figure, and I don't want my colleagues to notice my efforts.

CEO: Excellent! Keep it up! I want you to maintain this status, presenting as a "he" during the day and a "she" at night.

Cindy: Yes, sir. I'll follow your instructions.

CEO: Did you bring something for me?

Cindy: Yes, sir. Here's the latest list of male candidates that could be suitable for your next feminization program.

CEO: Your bra is showing. I see you're wearing a bra too.

Cindy: Oops, I'm sorry. The breast form you chose for me is too large. I can't always button up my blouse.

CEO: Are you wearing a full set?

Cindy: Yes, sir. Of course. As a woman, I wear a full set of lingerie. As you can see, I'm not just wearing a bra and panties, but pantyhose too.

CEO: Excellent! Show me more. I want to inspect it myself and make sure you're wearing a full feminine outfit from head to toe.

Cindy: You don't believe me, sir?

CEO: I just want to make sure my new employee follows my instructions.

Cindy: *giggles* What you mean is, make sure the man you just hired, dresses up as a frilly female sissy secretary in the evenings, right?

CEO: Precisely.

Cindy: Absolutely. Let me show you what I'm wearing tonight. Just be prepared, since it took quite a bit of determination even for me to remain composed and tucked in when checking myself out in the mirror wearing this lingerie. *giggles* (Cindy unbuttons his white blouse)

CEO: Very nice! The red lace bra looks amazing on you. A brave and sexy choice! It fits your body perfectly and holds everything in place.

Cindy: Thank you, sir!

CEO: Now let's see what else you have on. Show me.

Cindy: What a naughty man you are, sir. I feel so embarrassed to show that I'm wearing panties.

CEO: Are you still a "guy"?

Cindy: It seems like I'm not anymore since you got me dressed up like this~ *giggles*

CEO: That's right! Since you are not a guy, it's quite normal for you to wear panties. You can look like a "guy" during the daytime, but you still don't qualify! And that is your limit. Do you know why?

Cindy: Because I'm wearing pantyhose and panties beneath my pants. *giggles*

CEO: Precisely!! So tell me, what are you?

Cindy: I am your sissy secretary who pretends to be a guy during the day but presents as totally opposite in the night time.

CEO: Good~~ You understand your role very well young "lady"! Could it be that tonight is when you start your next "phase"? Are you ready?

Cindy: Do I look like I have a choice, sir? *giggles*

CEO: Undress now! Take off your panties and let me started to train you.

Cindy: And my bra too?

CEO: No, keep it on. Let it serve as a reminder that you are now a "woman" because you are wearing a feminine garment. You must embrace the femininity within you if you're to succeed in this session.

Cindy: Alright. Here you go. And I think wearing my panties would make you feel even sexier during the training. *Cindy winks suggestively*

CEO: Oh, naughty girl! Look at how far you've come from being a timid and boring fresh graduate to embracing your femininity with such brazenness. I'm proud of what you have become. Can you see the positive changes?

Cindy: Absolutely! My guy-persona was dull, but my female-persona is daring and fun! She giggles mischievously. *giggles*

CEO: Well done! It seems like you're ready for the next step!
2 hours later

Cindy: How was my performance, sir? Did I meet your expectations?

CEO: Brilliant! You surpassed all expectations! Your verbal proficiency was remarkable. Your bottom looked untouched, and you moaned so delightfully! You have shown yourself to be a true slut!

Cindy:As they say—a man knows what another man wants. *giggles*

CEO: There are some other things I would like for you to work on though.

Cindy: What would those be, sir?

CEO: Primarily, I wish for you to train your body to behave as a proper lady should when being taken advantage of. Since you are no longer a man, you should not be touching yourself or getting aroused anymore—especially when someone is fucking you!

Cindy: Understood. Anything else?

CEO: Starting now, I'd like you to wear a complete lingerie set at all times, including during office hours. This means wearing a bra underneath your male shirt is a requirement while you're working.

Cindy: That's a bit naughty, isn't it? *giggles*

CEO: Additionally, you should stop wearing men's shirts and trousers for work. Instead, replace them with blouses and more feminine trousers to complement your nice lingerie. I want everyone in the office to know what a sissy you are.

Cindy: Oh my goodness! That is going to be a big change... Everyone in the office is going to know what a sissy employee I am.

CEO: Also, no more masculine clothes whatsoever when you're not at work or after you get off work—only skirts, dresses, and things of that feminine are allowed!

Cindy: Looks like it's goodbye Andy and hello Cindy! *giggles*

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