Crossdressing Story Novels & Stories

While waiting for my husband to pick me up at the parking lot, I came across a trending topic in my city. "How do I deal with an overly-clingy wife?" Amidst a flurry of boastful, lovey-dovey comments, one female username caught my attention. "Just pretend to be incompetent! My childhood friend was forced to marry someone he didn’t love. I gave him the idea to pretend to be directionally-challenged, which he has done for five years now. "When his wife got pregnant, he secretly mixed lubricant into the shower gel, causing her to slip. Then, on the way to the hospital, he pretended to get lost. He deliberately circled the suburbs several times, which led to her miscarriage and now she can't have children anymore." "Coincidentally, today is supposed to be the selection day for her promotion to professor. He offered to drive her to work, but he actually plans to pretend to get lost to make her late so that I can get promoted instead. "When she fails the selection, he’ll use that as a chance to convince her to quit her job, turn her into a useless housewife, and then kick her out!" Reading this suspiciously familiar experience sent a chill down my spine. Before I could ponder further, I heard my husband’s apologetic voice. "Sorry, honey, I got lost. I hope this won't affect your selection."

The new project was short on staff. Over everyone's objections, I pulled three former colleagues out of an overlooked department where they'd been warming the bench for years. The four of us became the project's core team. The bonus was generous, the workload light. They all said I was their lucky charm. Three months later, with delivery just around the corner, I passed the break room and overheard them talking. "The biggest credit for this project belongs to the three of us. Why should Chloe get an equal share of the bonus just because she recommended us? She barely did any real work." "Exactly. Let's talk to the director. We'll say all the core work was done by us, that she's not up to the task. We'll apply to have her removed from the contributors list." "Just thinking about not having to split those tens of thousands with her—it feels amazing." I pushed the door open. They stared at me, stunned. I smiled. They wanted to kick me out? Too bad. I was the director who parachuted in to evaluate them.

My mother claims my husband has cheated on me and pushes me to get a divorce. I want to collect evidence before proceeding with anything—if it's true, I have to uphold my rights. Yet she causes a scene at an art exhibition I've worked on for three years, humiliating me in public and making me sound like a gold digger. "How are you any different from a prostitute when you're holding this dumb exhibition with a man's money? I didn't raise you to be a gold digger! How can you be so revolting?" She slashes the million-dollar paintings in the exhibition, claiming that she's doing this for my good. She wants me to see the error of my ways and return to the right path. Meanwhile, I clutch my bloody hand, which she slashed with her blade. I say, "You say you want me to return to the right path, but is that what it really is? You want me to divorce my legally wedded husband, who's a CEO, without a penny to my name. "Then, you want me to marry a 45-year-old cheap man who has a child and no money? He even wants me to support him!"

When I visit my girlfriend's house during the Christmas holidays, her cousin, Antonio Esposito, humiliates me in front of everyone because of a scar on the back of my hand. "This scar looks like a remnant of the crossfire with the mafia! Bianca, why did you think that bringing an ex-convict home was a good idea?" The entire Romano family stares at me in a mixture of horror and shock. My girlfriend, Bianco Romano, even shakes my hand off while staring at me in disgust. Not only does Antonio flip the table, but he also calls over a few hooligans in an attempt to take me to the local police station. "We must teach scumbags like him a lesson!" he declares. After that, Antonio and the hooligans strip off my jacket and strap me to the tree in the courtyard. They then attempt to force me to admit that I'm working for the mafia. I can only gnash my teeth together stubbornly, refusing to yield no matter what. What they don't know is that the scar is a medal from my time in a peacekeeping war as a soldier!

On my 50th wedding anniversary, I took my worn, crumbling marriage certificate to City Hall to renew it. The clerk glanced at it—and froze. “This certificate is fake. Our records show you’ve never been married.” I stared. “Impossible. I’ve been married to Damien Slater for fifty years.” The clerk pulled up his file. “Well…Yes, Mr. Slater is married—but his wife’s name is Vanessa Grant.” Vanessa. His widowed sister-in-law. A military doctor who’d spent decades living among the troops. My hands shook as I returned home and confronted Damien. He didn’t even try to deny it. “I’ve treated you well all these years. Isn’t that enough? Vanessa is my true love. I only ever wanted her—our children, our life.” My son counseled me and said, “To spare your feelings, my parents kept it a secret their whole lives. You’re getting old now. What more do you want?” Only then did I learn the truth. The child I had raised with my own hands was never mine by blood. Decades ago, Vanessa and I gave birth on the same day. To ensure her child would grow up with intellect, privilege, and a future that I could provide, Damien switched our children. My own son? Damien drowned him in the pond the moment he drew breath. And I—fool that I was—raised Vanessa’s boy as my own. I even got him all the way to Claremont University. The truth broke me, and I collapsed. When I opened my eyes again—I was back. Back to the day I went into labor.

On the day I'm about to quit the game, I see countless live comments flashing across my vision. "Yay! The male supporting lead is about to quit the game!" "Now, the male lead won't have to worry about getting exposed for using the male supporting lead's game account to get into online relationships with others!" "Our darling male lead is too smart, after all! Whenever he goes on dates, he often uses the voice chat function in the game. That's why the male supporting lead is still kept in the dark!" "Holy shit, Henry really is lucky!" "To think that he used Vincent's max-level account to flirt with the four richest female players on the server!" "Later at 2:00 pm, he'll be meeting his first date partner, Yvonne Johnson the cold and aloof campus belle, at Cosmic Coffee!" "Tomorrow, he'll be meeting up with the top assassin in-game! The day after that, he'll go on a date with the second-highest paying player of the game! Wow, his time management skills really are amazing!" The "Henry" whom the live comments are referring to is Henry Luster, my roommate. So, he's been flirting with four of the top-tier rich female players while impersonating me, huh? More live comments streak past my eyes at that moment. "Why isn't the male supporting lead leaving? Yvonne is already waiting for the male lead right now!" "This is their first romantic date as the leads of this story! I can't wait to watch it unfold!" As I turn to look at Henry, who's styling his hair before the mirror, I suddenly realize that I'm the supporting male lead whom the live comments are referring to. My lips curl into a small smile. Since Henry has been using my identity to become a virtual casanova, then it's not wrong of me to attend each date in person on his behalf, right?

I've won a lottery hosted by the local bank that gives me an opportunity to experience a day as a rich person. Because of that, I'm given a temporary black card that has a credit limit of a billion dollars. Excited, I rush home to tell my wife, Lara Crawford, about it and plan on taking her to a fancy meal. Unexpectedly, Lara drugs me just so she can steal the black card. Then, she starts a livestream that's titled "Goodbye, Loser. Hello, Billionaire Life." with her male best friend, Adrian Schmitt. Lara can be seen buying a shopping mall with the black card on the livestream. Then, she mocks me for being an impoverished man who only deserves to eat the cheapest food available. What she doesn't know is that the purchase history of the black card is being live-streamed on the bank's channel at the same time. The title of that livestream is "A Test of Human Nature—When a Gold Digger Finds a Billion Dollars." Now, there are ten minutes left before the experience is over.

After my friend Josh Yates fell deep into gambling, he showed up one day wearing a wide, excited grin, insisting on taking me to Macoria. "I just won big," he said. "My treat. We're staying at the most luxurious hotel." However, the moment we landed, he led me straight into a private room buried deep inside a casino. "The truth is, I lost 7.5 million," he admitted. "If I can't pay it back, they'll sell me off to the Mykar Borderlands… "However, the woman who runs this place is looking for a man with a crescent-shaped birthmark. If they find him, all debts are wiped clean. "You've got one on your stomach. I saw it when you were showering. I'm sorry, man… I really don't want to die." Four men pinned me down on a sofa. That was when I noticed a child's drawing hanging on the wall. I had made it for my mother before I was taken from her. She cherished it, said she would keep it for the rest of her life. An icy smile tugged at my lips. Josh, Josh… this time, you really did place the right bet, I thought. Too bad the winner would not be you.

I lapse into unconsciousness for a few days after a high fever. When I wake up, I see my boyfriend and his best friend standing by my bed. I want to enliven the atmosphere, so I joke, "Who are you?" Eric Cobb, my boyfriend, is taken aback. I almost laugh at the look on his face. Then, he points at his friend, Jonah Mullen. "Don't you remember? Your boyfriend's been panicking over you. As his best friend, I have to be here with him." This time, I'm the one who's taken aback. Unexpectedly, Jonah steps forward and says, "That's right. I'm your boyfriend, Jonah Mullen."

I knew perfectly well that open flames were forbidden at a gas-leak scene, yet as a firefighter, I still backed my girlfriend's childhood friend when he insisted on lighting a cigarette "to calm his nerves." In my previous life, a sudden gas leak erupted during a gathering. Her childhood friend insisted on smoking to steady himself. I slapped the lighter out of his hand and yelled at him for trying to get us all killed. Humiliated, he ignored everyone's attempts to stop him and stormed outside—only to be crushed by an advertising board blown loose by the explosion's shockwave. Later, when I saved a child who had fallen from a building and was left hanging in midair myself, my girlfriend—my second-in-command—maliciously cut my safety rope. She stared at my corpse and said, "If you hadn't humiliated George in front of everyone, he wouldn't have died." When I opened my eyes again, I was back in that room thick with the stench of leaking gas.