Crossdresser Boss Novels & Stories

He said as he took off his jacket and wrapped it around my waist. I followed my boss out of the building. And let me tell you when I say that having people stare at me because I was so close to him, let alone wearing his clothing around my waist, was making me feel extremely uncomfortable. As we reached the street, a driver pulled up and Atlas opened the door for me to get in. We both sat in the back seat, next to each other, and I stared out the window. I was hoping to zone out. It was all I could do to distract myself from this hunk of a man sitting next to me. I heard him tell the driver of a business I’ve never been to, and we drove on to our first stop of many.

The stranger said to Micheal with loud and harsh tone, commanding. Micheal recoiled trying to rearrange himself, avoiding direct eye contact " Yes boss." My eyes widened in bewilderment as Michael's response rang in my ear again and again. Boss?, I asked myself trying to digest what I heard, probably I misheard. Michael's response still ringing in my ear. Boss? It still isn't clear to me. The only person Michael refers to as Boss is the rude, arrogant and inhumane Kaiden Kross. The same one that everyone in Michael's department and every other department in the branch complains about.

“You disappear all night, ignore my calls, and roll up in a fucking limo wearing designer everything like you’ve been body-snatched, and all I get is hey?” “I need to talk to you,” I said, barely above a whisper. “Inside.” We walked up the stairs in silence. But the second the door clicked shut behind us, the dam broke. “Who the fuck is he?” Mark’s voice was raw, his chest heaving. “What kind of guy yanks you out of our life like that and turns you into this overnight?” I swallowed hard, bile burning the back of my throat. “Nathan Cross.” He laughed. It was loud and sharp, almost manic. “Jesus. Nathan fucking Cross. Your boss. Of course it’s him. Of course it’s the guy who owns half of Manha

I kept my spine straight. Adrian's voice remained calm. "She didn't create the scandal." "I don't care who created it." Robert slammed his palm against the table. The sound echoed through the room. Several directors flinched. "I care about what happens to this company." His gaze moved to me, deliberate and cold. "And they're seeing an employee at the center of it." I swallowed hard. Adrian stepped forward. "Don't speak about her like that." Robert's expression changed. There was something almost like amusement in it now. "Like what?"

Frowning, she grabbed one last, most important item: men's underwear. ​She weighed the sizes for a moment, her face reddening slightly as she recalled her boss's bodily proportions, then chose the largest box. ​Just as she turned toward the cashier, her steps halted. Her blood ran cold. ​Standing only a few meters away from her, in the exact same men's clothing aisle, was Michael, her boyfriend, or more accurately, the bastard she had caught wrestling on the bed with another woman yesterday afternoon. ​The man was not alone. His left arm was affectionately wrapped around the waist of his female coworker, Jessica, the blonde who always acted sweet.

Gave the overlooked ones a real shot. Promotions. Raises. I broke rules to make it happen. Two years later, the company's value tripled. Industry leader. And yesterday? These same people were lined up outside my office, sucking up. Now? Not a single one spoke. Seeing them hesitate, he shoved Clara aside. "What are you scared of? I'm Lombardo Corp's CEO now—the real Lombardo heir," Philip said. He jabbed a finger at me. "And him? A fake. Exposing him's doing everyone a favor. Got a problem with that?"

In the bright lights of the lobby, my wet linen dress was entirely transparent. The dark outline of my bra and the curves of my skin were starkly, undeniably visible to every passing soldier in the room. Mortified, I slammed my arms over my chest, stepping back with a choked gasp. Severin looked away. He unbuttoned his heavy military overcoat and removed it from his broad shoulders. Without a word, he draped it over me, carefully pulling the edges closed over my chest to block me completely from the prying eyes of the personnel.

“The man was kind enough to buy me some clothes. I have no idea where mine are to be honest. I found these and wore them.” “Maya, this is Ambrose! You and I have been working here since ages even with a discount included we still can’t afford to buy even a single piece from any of the Ambrose clothing stores. The man must be loaded to buy you this.” “Tell me about it,” she sighed then suddenly remembered something. “Now tell me about the new boss. How angry is he?”

’ “BOSS! I GOT THE CRAZY OLD MAN!” The bald man was really annoyed and his vicious gaze landed on his subordinate. “Why did you bring him? Do you want me to do your job?” He huffed. “No, boss. I apologize.” The thug subordinate pushed the crazy old man in front of the bald man. This was his time to show off that he was fierce and deserved to be promoted. He stepped on the old man’s chest and loudly asked. “Do you know this lady?” The bald man took off the other pair of his shoes and hit the subordinate’s leg a few times. “What b-llsh-t are you doing? Get your legs off the old man!”

*** The boss of the gangs walked in and saw Isabel, he bite his lower lips and began to unbuckle his belt. "This would be sweet, " the man said and went to close the door. "I want to enjoy this alone before my friends come to eat you up," the man said and fully pulled off his trouser. "Did you know I'm the CEO of Idesign and Isascom?" Isabel asked. "And what if you are? Are you threatening me or why are you making me know your identity?" The man asked, he was now on his boxer pant, the bulge on his trouser looked so hard as if it will tear off the boxer.