Crossdressing Story Novels & Stories

As a hopeless romantic and a trusting fool, I never saw it coming. The man who once swore he loved me to the bone ended up in bed with the very girl I had been supporting—a poor, sickly girl who played the part well. He didn’t stop there. He convinced me to donate my kidney to save her, knowing full well it meant losing our unborn child. Together, they wove a twisted plan to rob my family of everything, drowning us in insurmountable debt. In the end, my mother and I had nowhere to turn but the rooftop. The last thing I saw before jumping was a flood of crimson, and the agony that consumed me was unforgettable. Yet, when I opened my eyes again, I was back—ten minutes before I made the fateful decision to help that girl. This time, things will be different.

Right after I am done with a meeting, I scroll through social media and come across a warning post with my company's location tagged. The title reads, "Avoid this place! Anyone who comes here is a sucker. The company is so stingy that it can't even provide decent snacks." The photos show the Starbucks drinks and five-star desserts I just asked my assistant to distribute to everyone. I frown and tag everyone in the group chat, asking for suggestions about the teatime snacks. A Gen Z intern, Alice Grimes, immediately sends a voice message, "No offense, Ms. Knox, but these mass-produced desserts are full of trans fats. Even dogs wouldn't eat them. A good company would hire Kitchelin chefs to cook on-site. Now that's called having true respect for employees." I laugh in disbelief. My company spends 50 dollars per person on daily tea time, which is considered top-tier in the industry. So, I reply, "Since it's hard to please everyone, we'll cancel teatime from now on and convert it into a cash allowance for everyone." Less than five minutes later, there is a new update in the social media post. "Guys, you won't believe this. I made a reasonable suggestion, and the petty boss just cut our teatime perk! This is how a typical capitalist behaves. They can't handle any honest feedback."

An emergency has just occurred at the hotel. William Davis, the mayor's son, suffers from cardiac arrest in the hotel. Unfortunately, there's nothing the doctor in his team can do about it. I happen to be vacationing nearby, so I quickly rush toward the scene. As soon as I rush into the lobby, the security guards quickly stop me. "A life is being saved at the moment. Unauthorized personnel aren't allowed to enter." I'm about to dig out my work badge when Lydia Sharpe, the intern tagging along, suddenly covers her mouth and shouts daintily, "Don't let her in! There's a scalpel and a syringe of anesthetics in her bag!" Everyone is shocked by Lydia's revelation. The security guards instantly have me surrounded while wearing vigilant looks. Sweat starts rolling down my face out of anxiety. "I'm the head of the cardiothoracic surgery department of Central City Hospital! I've heard about the patient's condition! He must undergo a thoracotomy right away!" The next thing I know, Lydia has snatched my bag out of my hands. Things such as the sterilized gloves, defibrillator, as well as life-saving medication are scattered all over the floor. Lydia steps on the one and only life-saving pill instantly. "I just heard you claiming that it's best if the mayor's son dies right away! Why are you still pretending to be a savior? "Hurry up and arrest her! I suspect she has something to do with the ongoing case! She's definitely a murderer!" The person in charge's expression shifts drastically. Soon, he pins me on the wall. "Detain her and inform the security department right away! This woman is suspected of being involved in a murder!" As I stare at Lydia, I can't help but tremble violently. Right now, I'm the only one in the entire city who can perform the surgery on William. Unfortunately, he can only last for another half an hour in his current condition.

"Ms. Smith, a complaint has been filed with HR. You have been accused of misusing your personal vehicle for unauthorized commercial activity." The administrative manager dropped a printed copy of the so-called joint complaint onto the desk, a faint, knowing smile on her lips. The company had decided to issue me a fine, placed a formal warning on my record, and revoked my performance bonus for this quarter. I stared at the handwriting on the complaint, then let out a short, incredulous laugh. I recognized it instantly. It was Selena Rogers. The same coworker who had been hitching rides with me to and from work every day for the past three years. It was all because of last night's storm. She had insisted I take a long detour to drive her to the mall so she could pick up her boyfriend, and I had said no. Then, in the break room, Selena's voice carried loud and clear. "Jennifer, I didn't have a choice. "We have to keep work and personal matters separate. The transportation stipend from the company isn't for you to make extra money." Around us, coworkers glanced over, whispering and pointing, as if they had completely forgotten how eager they once were to ask for a ride home. I took a slow breath. "Fine. I accept the company's decision." Then I pulled out my phone and made a call. "Mr. Wallace, I won't be renewing the lease on those two vans. "Yes. The ones that have been picking up and dropping off the admin and sales teams every day, free of charge." For three years, I had been the easygoing one, paying out of my own pocket every month to lease those vehicles so my coworkers could treat it as a perk. If that was now considered unauthorized business activity, then from this day on, everyone could figure out their own way to get to work.

On the day of my wedding with my girlfriend, I was unexpectedly informed by the hotel that our ceremony had to be postponed by a couple of hours. With no time to notify relatives and friends of the change, I had to rush to the hotel entrance to intercept guests. Upon arriving, I was stopped at the door by security, who told me that a wedding was currently taking place inside. The host's voice could be heard as I saw my girlfriend, wearing a veil, smiling and extending her hand to a man who was half-kneeling. In the audience, all the bride's relatives who were supposed to attend our wedding were seated, clapping and cheering. The man on stage was her dream guy and also my current superior. Seeing me causing a commotion, my girlfriend warned me, "I'm just helping out. Alex is your superior. I'm also doing this to help you. Don't cause any trouble." Just helping out? I had booked the wedding venue, chosen the time, designed the wedding dress, and personally sent out the invitations. How could a wedding be rearranged so suddenly? I looked coldly at the ring box the man was holding. "It seems my taste is quite similar to my yours. If that's the case, this diamond ring is yours, including the wife." My girlfriend finally panicked.

The day before his Alpha Induction, Luke destroyed everything. He’d spent years obsessed with a weak Omega—a girl promised to Reno, the lethal Alpha of the Northern Territory. Luke couldn't stomach losing her, so he crashed their ceremony and took her by force. That same night, he Marked her in front of everyone. The Pack held their breath, waiting for my family to become the biggest joke in the territory. I braced for the humiliation, expecting to be the girl everyone pitied. I was wrong. The next morning, I found Reno leaning against my balcony railing. He was massive—broad-chested with arms built for violence. He smelled like raw power and imminent danger. He didn't look like a man who had just lost a mate; he looked like a man looking for a trade. "Luke stole my female," he rumbled, his dark eyes locking onto mine. "I want you as her replacement. Be my Luna. It’s a fair trade, don’t you think?" I didn't hesitate. I looked him dead in the eye and nodded. "It is," I replied. "I’m in."

The fearsome Romano family has made an announcement. Whoever among me and my sister, Vivienne Everhart, can give birth to the first grandson of the Romano bloodline shall inherit the Romanos' wealth that's worth tens of billions of dollars. Also, said grandson will be the next Don of the Romano family. In my previous life, Vivienne had married Dominic Romano, a healthy and strong young man of the Romano family. My parents were the one who had arranged for this marriage to happen. I, on the other hand, got married to Julian Romano, a gloomy man who was confined to his wheelchair due to his crippled legs. In less than a year after our marriage, Julian had regained his ability to walk once again. At the same time, I got pregnant with the first grandson of the Romano family. As such, Vivienne got abused by Dominic to the point that she completely lost her marbles. That was how she became the laughingstock of the rich socialites of the upper crust. On the day I was about to go into labor, Vivienne stabbed my belly with a blade. Then, she grabbed me before jumping off a tall building with me in her arms. When I open my eyes again, I see Vivienne snatching away the bouquet made of blue roses that's given to me by Julian. "I want to marry Julian!" "Vivienne, how could you snatch Isabella's bouquet away?" As soon as Vivienne receives the fancy blue rose bouquet, she freezes in place when she hears our father scolding her. After Dad grabs the bouquet from Vivienne's hands, he passes it to me before saying, "Isabella, you have a healthy body. Julian might be handicapped, but at least he's pretty talented when it comes to running his business." Then, he pats Vivienne on the head lovingly. "Vivienne, you're in poor health. Marrying Dominic is your best option." As I stare at the blue rose bouquet in my hands as well as the wedding gown I'm currently wearing, I dig my nails into my palm forcefully. Finally, I realize that I've gotten reborn.

Right before the last full-length practice exam ahead of the SAT, my boyfriend, Blake Romero, who had always ranked in the top ten, somehow ended up with a score of zero. His eyes were red as he clung to me, his voice shaking while he said he had developed severe test anxiety. "Samantha, there's no way I'll get in this year. Can you stay back and retake the year with me? I can't do this without you." Looking at how pale he was, I almost gave in. On my way to the school clinic to grab him some meds to calm his nerves, I accidentally overheard him talking to a girl from a poor family. "Blake, what if Samantha finds out you're lying to her?" His voice turned soft, almost indulgent. "Relax. She loves me so much that she would give up anything for me. Even if she finds out, so what? Besides, her family's loaded. Losing a year won't matter to her. Arrington University only has two spots this year. As long as Samantha doesn't take the exam, those spots are ours." Standing outside the door, I felt as if I had just had a bucket of ice poured over me. So this was his plan! He was willing to ruin my future just to clear the way for the girl he really cared about. What he didn't realize was that Arrington University had only ever been my backup, something I chose just to stay by his side. Without him dragging me down, I could aim for something better.

Wanting to give my boyfriend, Justin Letterman, a surprise on Valentine's Day, I throw myself at him when he enters the room. I push him against the door and kiss him passionately. It isn't easy to transfer the spiked wine from my mouth into his, but his reaction is cold and indifferent. He says nothing as he pushes me aside to turn on the light. "Don't you want my first time anymore, darling?" I ask bashfully as I grab his hand. His breathing turns heavy in an instant. Smiling, I slip my hand under his shirt, but I'm distracted when I hear the front door creak open. "Babe," Justin coos in a deep and hoarse voice. "Why are you in such a hurry?" my best friend, Natalie Quinn, asks coyly. The wanton noises of kissing and moaning echo into the room. Before I can snap back to my senses, I'm yanked into a closet. Am I the one getting caught, or am I the one doing the catching?

On the day I receive my Distinguished Service Medal, I also receive word that my grandma has passed away. My superior grants me special leave to return to my hometown to mourn her death, so I rush to my ancestral home at once. But when I reach the ancestral graveyard behind the hill, I witness something that makes my blood boil. The graves of my deceased family members have been razed to the ground. Even my parents' graves have been brutally dug up. Their urns are now placed under flower pots filled with blooming red roses. Grandma's coffin has been pried open as well.Her body now lies strewn on the ground and has started to rot. I also see Lucy Stewart, my autistic younger sister. Melissa Abbott, my wife's assistant, orders Lucy around like a maid, forcing her to move heavy construction materials around. Enraged, I grab Melissa by the throat and throw her to the ground. "How dare you destroy my family's ancestral cemetery and make my sister do hard labor! Do you want to end up buried here too?" Melissa coughs up blood before crawling back onto her feet, her expression vicious and scornful. "I'm simply carrying out Ms. Fuller's instructions. She says that your ancestral cemetery is located in a good spot. It's also the perfect size to be turned into a private horse ranch and a garden for her future husband. "Ms. Fuller calls the shots here in Joverton City. Who the hell do you think you are, huh?" Resisting the urge to put an end to her life, I call up Eva Fuller, my wife. "I heard you call the shots here in Joverton City. Well, I shall put that to the test today!"