Crossdressing Story Novels & Stories

During the holiday, my six-year-old son received his cleft-lip surgery. He wore a mask and sat quietly in our family bookstore, engrossed in a picture book. A young man came in, pinching his nose dramatically as he swaggered up to the manager. "Why did you let someone with an infectious disease in here?" he demanded loudly. "Get them out!" The manager winced. "Sir, I'm sorry, but I don't have the authority to remove other customers." Undeterred, the man marched up to me. "Be wise and get out of here. My girlfriend is Imogen Slater, CEO of the Slater Group. You don't want to mess with me." I froze in stunned silence. Imogen despised all men except me, and this guy claimed she was his girlfriend.

My son was caught in a car accident. My husband said that without a cornea donor, he would be trapped in darkness forever. Heartbroken, I let him sweet-talk me into signing away my corneas. Blind, I overheard my son gloating, "Dad, the plan worked. Mom fell for it, and Rachel's got her sight back. She won't be miserable anymore." "Yeah, now we're a real family with her," replied my husband. The truth gutted me. They'd played me like a fool to save my husband's old flame. When I confronted them, Rachel Huffman shoved me down a staircase, and I died in agony. But when I opened my eyes again, I was back on the day of my son's car accident.

In my previous life, everything I do to care for myself somehow ends up benefiting my new housekeeper instead. I apply expensive skincare, yet dark spots and fine lines spread across my face, whereas the 45-year-old housekeeper's face becomes silkier. I jog every morning, yet my body only grows heavier and bulkier, while hers becomes slender and toned. When my husband notices the stretch marks on my abdomen, his face twists with disgust, and he never touches me again. "I genuinely can't bring myself to touch you. How can you look worse than Mirabelle when you take such good care of yourself?" My housekeeper looks at me with a sinister smile. A chill crawls up my spine, and the strange feeling makes me fire her on the spot. Yet, as soon as she leaves, I start aging at lightning speed, entering menopause 20 years early and developing diabetes and high blood pressure. I see every doctor I can, but after hanging on for a week, I die from a stroke. When I open my eyes again, I'm back on the day she first reports to work. This time, I push away the royal jelly she sets in front of me with a pleasant smile. "I've been avoiding certain foods lately. You can have it instead."

Five years after our breakup, I saw my ex-fiancé, Nico Luciano, showing off his newborn on social media. The next day, he cornered me at a private club and slid a black card across the table. “Lena, Sophia finally had a boy, the heir to the Luciano family. Now I can marry you.” He tried to soften his tone. “Having been widowed to my late brother for five years, she just wanted a child to care for her. I had no choice after the first two were girls. “Thank you for waiting these extra two years. The wedding is set for next Monday, and the invitations are ready.” What he didn’t know was that I was already married. I am now the lawful wife of Vincent Moretti, the don of the North Alumcian Mafia Commission, and a core decision-maker of the Moretti family’s financial empire. Watching Nico’s confident smile, I sent a message to my underboss. “Notify the elders of the five major mafia families. Next Monday, I’m removing the Luciano family from power.” Then I looked up and smiled at him. “Marry me? Save your own career first.”

On the day we receive our bonus, one of the staff members of the finance department gives me 500 dollars worth of vouchers for the fast food restaurant downstairs. He tells me that my wife, Jillian Dunn, who is also the company's president, specifically ordered him to do so. In utter disbelief, I seek out Jillian and question her. "Didn't we agree that whoever secures the project will get a 50,000-dollar bonus? Stop messing around! I still need to pay for Freya's cochlear implant!" "I'm not messing around with you," Jillian answers seriously. "These vouchers can last you for a whole month. I wouldn't even give them to you if you were anyone else. "Money is tight right now at the company. Besides, Freya has been deaf for more than a decade now. She can survive being deaf for another decade." The next day, Jillian gives one of the interns a sports car that's worth 50,000 dollars. I look at the photo she uploads of her and the intern grinning widely as they sit in the car and give it a like. Jillian must assume that everything is proceeding smoothly since she has signed the contract. However, she misses the additional condition that's printed on the last page of the contract. I dial her rival's number, asking, "Ms. Swan, are you interested in Project Charlie?"

In the fashion industry, I was known as the most mysterious designer. I worked hard to keep my identity from the public. As I stood at the top of business, I was invited to be the secret judge of the Innovating Design Competition’s final round. The organizer reserved a VIP seat for me in the middle of the front row and ensured that my presence would not be revealed. Just when I was about to sit down, a new male influencer pushed me aside and threw his hand bag onto my seat. “What are you looking at, bumpkin? How dare you show up at the VIP section dressed like a beggar? Where’s the security? Throw this person out!” I swallowed back my anger and replied coldly, “This seat was reserved for me.” The influencer laughed. “Yours? Do you know who I am? Ms. Reid spent eighty million dollars in sponsorship to get me to come here! Ms. Reid has the final say in this industry. Do you understand me?” I could only scoff at him. How bold of the Reid family! Did they really think they could make this kind of decision without consulting me?

On our Christmas break road trip, my cousin Felix Lloyd spotted some high-powered speakers at a highway rest stop. He had to have them—said he wanted to "blast it." "It's Christmas. We finally get to see everyone! We need some vibe!" My wife, Lana Ramsey, smiled and helped him pay. "Young people have energy. They know how to enjoy life." I yanked the power cord out. "Those aren't for regular cars. This is an EV. Overload it, and the whole system fries. Then what—just stuck in the middle of nowhere?" Lana's parents, Vincent and Donelia, booed me, calling me a buzzkill. Felix cranked the volume all the way up. Lana glared at me. "Say one more word and get out. I'll drive." Later, the speakers fried the battery system. We were stranded in total darkness on a rough mountain road. They finished the last of the food, then shoved me out to "go find help." I slipped, rolled down the slope, and died. When I opened my eyes, I was back—right when Felix jammed the speaker plug into the charging port. I grabbed a few more subwoofers and handed them over. "One isn't enough. Add more. That's how you really crank it."

After I shared my five-million-dollar commission with my department colleagues, they drag me to a hotel and celebrate with me for three days straight. But when I walk past the bathroom, I overhear a conversation between two of my colleagues that stops me cold. "Have the results of the vote come out yet?" What vote? Confused, I check my phone and find that I've been removed from the Project Department's group chat. "Who else could it be? Our hero, Zane Carter, received eleven votes. It was unanimous, and the motion was passed." "Serves him right. I've never liked him anyway." I freeze. I can't believe that my colleagues would betray me after what I've done for them. After taking a moment to calm down, I immediately decide to resign. The next thing I know, I receive a call from the company chairman, Wilson Smith. "Have you made up your mind? Quitting now would breach your contract. As a result, your five-million-dollar commission would be revoked. "You're also a key technical staff member. If you leave, your entire department would most likely be dismissed. Once that happens, your colleagues will end up unemployed. Are you sure about this?" I lower my gaze and let out a cold laugh. "Absolutely."

I knew perfectly well that people from the Emirates do not eat pork. Yet this time, I watched in silence as my husband's childhood sweetheart insisted on placing a pork dish on the table. In fact, I even supported her decision. In my past life, when our company hosted a welcome banquet for powerful investors from the Emirates, she had been desperate to flaunt her cooking. Against all reason, she forced a pork dish onto the menu. I stopped her then. I explained that pork was forbidden by religious belief, and that offending the investors could cost us everything. If they withdrew their funding, the company's finances would collapse overnight. She took my warning as jealousy. In a fit of rage, she ran out of the banquet hall and was struck by a car, leaving her in a permanent vegetative state. I thought my husband would break down. Instead, he remained calm, stayed through the dinner, and secured the investment in surprisingly calmness. The truth revealed itself later. After the company went public, he brought me abroad under the guise of business, only to drag me onto a medical ship in international waters. As my kidney was cut from my body, I cried and asked him why. His answer came with a slap. "If you hadn't been jealous back then... If you hadn't tried to sabotage her, she wouldn't have ended up like that." I died in agony on the operating table. After my death, he used the money from selling my organs to cure his beloved childhood sweetheart, and the two of them went on to live rich, comfortable lives together. And then I opened my eyes again, back to the very day she decided to serve pork to the clients.

I had returned from overseas to attend my foster son's wedding, already wearing my dress for the evening. My former high school classmates recognized me and pointed at me, laughing wildly. They tore my dress off me without hesitation. Ruby Saunders apologized to me, but it was all an act. She looked at me with malevolence. She had instigated her lackeys to strip me in public. When I tried to retaliate, she slapped me so hard that I fell to the ground. I closed my eyes and laughed coldly as I saw the cruel excitement on her face. She used to imitate me and accuse me of copying her, but I always endured it. However, today was my last straw. I would not allow her to marry into my family and turn me into her mother-in-law, no matter what!