Crossdressing Story Novels & Stories

The new intern, Cynthia Joller, had posted about me online, claiming the company had made them use their leave for team building. No one wanted to fly all the way to an island to spend time with colleagues. However, what the internet did not know was that our company's team-building tradition involved booking a top-notch five-star resort every year: all-inclusive, family-friendly, with an extra three days of paid leave, and a $30,000 budget per person. The whole internet dubbed me a cold-blooded capitalist, so I decided to give in to their demands and issued a notice. [In response to employee feedback and to honor personal time, this year's team-building retreat has been canceled. Instead, a $500 allowance for personal travel will be provided.] The notice stirred up a commotion in the company. Long-time employees gathered at my office door, pleading for the return of the sunny Madiles retreat.

Our expedition team ventured into a desert wilderness to investigate rare mineral resources when we were suddenly struck by extreme heat that reached 158 °F. I nearly passed out from dehydration and quickly reached into my backpack for the electrolyte water I had prepared in advance. Just as I was about to drink it, I realized the bottle was half-filled with urine. When I turned around, I saw Ben Murphy, my wife’s childhood friend, gulping down my electrolyte water. As I was about to confront him, Amy Garner, my wife, grabbed my sleeve and said, “Don’t be mad. I gave Ben your electrolyte water. He’s almost dehydrated. You can make do with this for now.” My vision started to blur. Clutching the half-empty bottle of urine, I asked through gritted teeth, “I’m dehydrated. Instead of letting me rehydrate properly, you want me to drink this? Are you trying to kill me?” Amy was upset. “Don’t be ridiculous! Ben doesn’t work out daily like you do. He can’t handle this heat. Wasn’t it right to give him the electrolyte water? Besides, urine can hydrate you, too! Don’t be picky at a time like this.” Seeing how unreasonable she was being, I sent a distress signal with my location just before losing consciousness. [Severely dehydrated, near death. Expedition mission suspended. Request immediate rescue. Also reporting a robber in the team. Notify the police immediately.]

I'm reincarnated a week before the college entrance exam. Despite being the soon-to-be top scorer, I stab my eye with a syringe. In my past life, Marianne Quentin, my boyfriend Lance Russell's childhood friend, reported me for cheating off her during the final mock exam. The teacher compared our papers and found that my essay was identical to hers. He harshly criticized me and warned me not to repeat my mistake. However, Marianne reported me for copying her answers again during the math exam. Once again, my answers were found to be identical to hers. The teacher scolded me for being incorrigible and sent me home to reflect on my actions. I couldn't understand what had happened. Clearly, I'd never cheated, but my answers were nearly identical to Marianne's, whether in writing and language or in math. As the SAT exam loomed over me, I could only suppress my doubts as I stepped into the exam hall. I finished the writing paper and thought I was safe. However, Marianne stepped out and accused me of cheating again. I tried to defend myself, yet the answers on my paper were identical to hers. In the end, I was disqualified, kicked out of the exam hall, and banned from taking any exams in the next two years—just because I "cheated". I succumbed to despair and leaped from the rooftop. When I open my eyes again, I'm back to one week before the SAT.

On New Year's Eve, my girlfriend of three years, Gina Jarrey, invited me to her place for dinner with her family. Before I could even take a bite, she drugged me and left me half-conscious. She mumbled, "If we don't pay them back, they're going to cut off my brother's hand. I had no other choice but to hand you over. Don't blame me for this. You're just unlucky for having a face identical to the man Ms. Carmelia Sanders is obsessed with. Once my brother's gambling debts are cleared, you might even end up living the high life. It's a win-win!" My mind drifted in and out as her entire family handed me over and sent me to a mansion that looked eerily familiar. First of all, unless I was mistaken, this place belonged to my aunt. Second, she had an extreme brother complex and had never liked any man other than Dad. And finally, years ago, a distant relative of mine got sent off to work in the mines in Frongo just for rolling his eyes at Dad. So really, who was the unlucky one getting delivered to my aunt's doorstep? Oh my, what a tough mystery to solve.

My sister and I are twins, but my mom never liked me. Once I secured admission to a prestigious university, my mom insisted that I work to finance my sister's college education. However, my sister decided to abandon her college studies during her second year, driven by the desire to marry a man a decade older than her. Things took a dark turn when her boyfriend was involved in a hit-and-run accident. My sister drained my medical treatment funds to keep him out of jail, even if it meant jeopardizing my own well-being. I didn't survive. I woke up again and had a second chance at life on the day when the admission results came out. My sister was crying and pleading, "Sister, can you let me go to college this time?" In this life, I won't give in to her demands.

I'm dressed in flip-flops and shorts when making an inspection of the five-star hotel my husband just acquired. When the front office manager spots me, she immediately calls for security with a disgusted look on her face. "The hotel's WiFi isn't meant for people like you to use. Hurry up and pay me 200 thousand dollars in Internet costs, then get lost!" I calmly tell her that I'm the owner of the hotel, but that only makes her sneer. "The owner of the hotel? Hey, old hag, you're putting on an act in front of the real deal! This hotel was a birthday gift from my husband to me. Aren't you fantasizing a bit too much?" Oh? Since when did Ian Lambert get another wife behind my back?

As the owner of a small private business, I had never been stingy with my employees. Having made a million in profit, I distributed $850,000 to them. I believed this would win people’s hearts. I never expected it would lead to being reported by my own employees. "We have received an anonymous tip-off from your company’s employees alleging arbitrary wage deductions and unfair profit distribution. The report further states that company discipline is disorganized and that employees are being compelled to work overtime, constituting a serious violation of labor laws. Immediate corrective action is hereby required, along with a fine of $500,000." Fine. Since they were so dissatisfied with my policies, then we would do things by the book—by the rules every other company followed. I would keep every last cent of this one million in profit.

When my best friend and I went for prenatal checkups, we both found out we were carrying babies with the super-male gene. The doctor advised us to terminate the pregnancies. I immediately went through with it, but my best friend was hesitant. I kindly advised her, "This child will ruin your life someday." She reluctantly agreed. Later, her husband cheated on her and tried to justify it. "If you can't give me a son, why shouldn't someone else?" Her husband's mistress chimed in, "What's the point of a woman who can't bear sons?" As a result, she blamed everything on me. When I wasn't paying attention, she poisoned my water and watched me die. When I opened my eyes again, I was back on the day of our prenatal checkup.

As the end of the year approaches, my wife, Sylvia Small, who is five months into her pregnancy, accidentally falls into a lake. Our neighbor who is a police officer, Raven Weber, jumps in and rescues her. Unfortunately, she slips into a coma after her heroic feat. As I rush over, I see that a crowd has gathered at the scene. Sylvia is drenched from head to toe, wrapped up tightly in a blanket. Water droplets keep dripping from the tips of her hair. "Are you alright, Sylvia?" I ask, drawing near. The moment Sylvia sees me, she moves toward me and burrows herself into my arms. She clings to me like she is clinging for dear life. "You're finally here, Zach!" she exclaims emotionally. I frown and push her away. "Just say what you have to say. This suit is expensive. Don't dirty it," I said indifferently. My words make Sylvia's eyes go wide with disbelief and shock. But that only lasts for a second before an anxious look replaces it. She holds my arms firmly and says in a choked voice, "Officer Weber is in a coma because of me. Please transfer a sum of money to me so that I can thank her for saving my life." I glance at Sylvia impatiently and reply, "What's that got to do with me? Why should I transfer you my money so that you can give it to her?"

On my birthday, Jake handed me two bucks and took me to a gas station to buy a lottery ticket. Then he dashed off, claiming he had an urgent work meeting. As I sat alone in the restaurant celebrating my birthday, I spotted my boyfriend, who claimed he had no time for me, having dinner with another woman. Without a second thought, I sent him a breakup text right then and there. Two days later, that lying jerk had the nerve to demand I return the lottery ticket. That's when I discovered it was worth $5 million. I cashed in the ticket and told him to get lost.