Cross Dressing Story Novels & Stories

On the very day I returned home, my would-be mother-in-law slapped a check across my face. “Five million dollars. Walk away from my son. I’ve dealt with gold diggers before, who think a pregnancy can lock a man down. You’re not nearly as smart as you believe.” Before I could say a word, a girl in a white dress shrank behind her, clutching her sleeve with trembling fingers, her eyes brimming with tears. “Mrs. Sterling, please… don’t do this. What if Adrian finds out? And… if he truly cares about her, I’m willing to step aside.” I let out a soft laugh. So that was the story she had written for me. A calculating woman trying to steal her man. I bent down, picked up the check, and tucked it neatly into the deep neckline of Lily Bennett’s dress. “Here. A tip. Your performance wasn’t bad.” Then I pulled out my black card and flicked it onto the table. “Ma’am, I’ll offer you ten million. Keep your son on a leash, and tell him to stop bothering me. I find him revolting.” I paused, then added lightly, “Oh, and one more thing.” I gestured toward the delicate little flower she was guarding so carefully. “The girl you’re protecting? My father brought her home last year. His illegitimate daughter. “If anyone thinks they’re joining my family, they should probably ask the Bennetts for permission first.”

On our fifth dating anniversary, my boyfriend, Luke Bolton, gives me a cheap bracelet worth less than a hundred dollars. On the same night, he splurges ten million dollars on a yacht for his first love, Cindy Gale. I refuse to accept this, and he accuses me of making a scene. "I gave Cindy that gift to boost the company's stock price, not because I still have feelings for her," he says. "You're poor, and I still promised to marry you. Isn't that enough? This was actually your last test, Elisa Gray, but you failed it." I break up with him, and he immediately proposes to Cindy. Five years after that, we meet again at a luxury hotel during a business summit. His company is about to become an industry giant, and Cindy is holding onto his arm. When he sees me, I'm standing in a fountain, all drenched and disheveled. "Elisa," Luke sneers. "When you turned me down back then, did it ever cross your mind that you might end up worse than a homeless person? "Don't think acting pitiful here will make me feel sorry and take you back." I ignore him. My son's cherished blue diamond was a birthday gift from his father, and he accidentally dropped it into the fountain. He's so upset that he's about to cry, and I have to find it right away.

Our company was having a team building event in the Huka Islands, where every employee would get their own room. As I prepared to check in, my colleague from the same department, Yvonne Caruso, suddenly snatched my ID from my hand. "The rooms are full. The rest of you should find another hotel." I did not say anything much but took my ID back to hand it to the employee working behind the front desk. "One room, please. Thank you." However, Yvonne pushed me away viciously and berated me, "I told you to get lost. Are you deaf?!" I was not prepared for it, and I hit the corner of the front desk hard. I felt a sharp pain in my waist and immediately lost my temper. Yvonne was infuriated when I pushed her back, and she roared at me, "How dare you push me! My dad is the real boss behind this company. He's the Don of the Carusos. Cross me and you won't even see it coming when you die!" I was taken aback and broke out with laughter a second later. The Don of the Carusos, Ian Caruso, was my father. Why did I have no idea that he had another daughter apart from me?

I dropped my car off for maintenance at the service center. When it was finished, I told the staff to put it on the tab of my cousin, who ran the shop. The staff member nodded and started to process it, but then the female manager stepped in. "We don't do tabs here. You've got to pay up now," she said, slapping the bill down right in front of me. Premium Diagnostic Scan: $80,000 Exhaust System Sound Enhancement: $100,000 Engine Harmony Calibration: $100,000 Total: $280,000. I laughed at the absurdity. Since when did my cousin start running a rip-off operation? The manager crossed her arms and gave me a snooty once-over. "Always trying to mooch off Chad. I've seen plenty of broke relatives like you. If you can't swing it, don't act like you can." Unwilling to argue with her, I pulled out my phone and called my cousin. "You have ten minutes to fire the manager, or your shop is finished."

Calvin and I had been married for seven years. While packing up some clothes, I found a cheap lighter in the pocket of his jacket. Everything he wore, from the inside out, had been carefully chosen by me to highlight his refined taste and status. However, in that girl’s Twitter photos, he looked like a college boy, dressed in cheap clothes and wearing a digital watch that cost only a few dollars while kissing her. Using a throwaway account, I casually liked the post and commented, "A perfect match." Then, I turned to Calvin and said, "How did I never realize you had such a thing for bargains?"

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.

Carl Anderson doesn't show up for our engagement party. I finally find him in a bar's private room after night has fallen. "I only think of her as a sister. Who would've expected her to want to latch onto me like that? There's no way I'll marry her in this lifetime!" He downs his drink. Later, when he and Angela Moran get married, he tells his friends to stop me at the entrance. He's afraid I'll crash his wedding and ruin it. "Keep an eye on Iris, guys. Don't let her crash the wedding!" he says. As soon as the words are out of his mouth, I show up with Henry Moran. "Don't even dream of stepping in there, Iris!" Carl looks at me warily. "You're so rude! You have to call her Aunt Iris now!" Angela greets me warmly and leads me inside.

I'm an heiress who's been bound to a gossip system. Everyone reads my mind on my first day back home after being reunited with my family. "Mom sure has done a good job of maintaining her beauty. It's no wonder she became an OnlyFans streamer after divorcing Dad." My mother is about to berate me for something, but she pales and stops when she hears my thoughts. I glance at the fake heiress, who's weeping pitifully. "My, she's pregnant. Is it John's or Zach's?" My two brothers exchange odd looks. Then, my father arrives. I cluck my tongue. "Oh, it's Dad's."

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!"

The day before New Year's, my younger brother announced he was bringing his girlfriend home for dinner. Excited, I drove my new car to pick them up, taking my daughter along with me. However, as soon as his girlfriend got in the car, her face darkened. "Henry, you didn't tell me your sister was staying at your place—and with a kid!" she snapped. I frowned and was about to explain when my brother quickly interjected, "She's not staying. After dropping us off, she'll be heading to a hotel." Only then did his girlfriend's expression ease. I swallowed my discomfort and asked my brother what he was planning. He leaned in with a conspiratorial grin and said, "Sis, don't cause any trouble for me, okay? My girlfriend is the daughter of the Cromwell Group's CEO!" My eyes widened in shock. Was not the Cromwell Group the same company my ex-husband had just handed over to me as part of our divorce settlement?