Caught Crossdressing Stories Novels & Stories

“Told me to shop. Didn’t say I couldn’t enjoy it.” His lips twitch—almost a snarl. He’s unraveling, but still keeping the mask on. Barely. “And the donation,” he adds, quieter. Darker. “Was that part of the spree?” I smile. Slow. Vicious. “Oh, you saw it?” His eyes go flat. Cold. But I see the fury underneath. I feel it vibrating off him like a storm beneath glass. “In honor of Nathaniel Cross,” I quote sweetly. “For his contributions to the systemic exploitation of vulnerable women.”

Sam walked up to me,but I couldn't concentrate because I felt so vulnerable. Dad's eyes were fixed on us,on what Sam was trying to do and I felt the ground open. “We can't do this is front of them, it's __” Sam dropped my dress and immediately,I was standing stark naked in front of them. I swallowed hard as I looked away. “Look at them.” Sam ordered and instantly,I turned to look at them. My nipples were hard as pebbles and I felt my pussy becoming slicker. “This is heavenly.” Sam whispered, taking one nipple into his mouth.

“It’s time.” He knew now that Andrea had been married to Maxwell’s brother, an abusive alpha and that was how she had gotten her scars. Her husband had died one day when she had had enough of the battering, but in their world, violence against kin had one outcome. Scarred hands and disfigurement. Maxwell had known about his brother’s behavior and promised to protect Andrea. She stayed because she felt indebted to him for what he had done.

Now, all at once, it hit me that everything I had given over the years had been nothing more than a one-sided effort. I was just about to book a flight when I realized I had forgotten my ID and passport, so I had no choice but to return home. The moment I opened the door, I was greeted by a mess all over the floor. Leftover snacks were scattered everywhere, along with half-finished dishes left behind. Right by the bedroom door lay something impossible to miss—a box of levonorgestrel pills and a piece of wine-red lingerie. Willow had never liked being physically intimate with me. Even Naomi's existence had come from a drunken incident.

I assumed the farce had finally ended, but as I stood in the luxury boutique listening to the manager's report on last quarter's new arrivals, those same familiar leather soles echoed behind me once more. I turned, and there stood Thomas at the entrance, arm crossed with a scowl. "It's you again! Bumpkins and freaks have no business in high-end stores." He sauntered inside, sizing me up like discarded trash. "We don't sell cheap grocery bags here, old man." His gaze swept the displays before locking on the limited-edition crocodile-skin shoes in the clerk's hands. He said simply, "I'll take those." The clerk hesitated, glancing at me. "Sir..."

“Don’t hide. We like you greedy.” Breakfast passes in a strange, charged domesticity. They talk about normal things—work, some basketball game tonight, whether we need more milk—while their hands wander. Jake’s fingers trace idle circles high on my inner thigh, never quite touching where I’m aching. Alex brushes past me to grab the creamer and lets his hardening cock press briefly against my hip through his sweatpants. I bite my lip so hard I taste copper.

As soon as he heard, he got jealous again. No matter how much I sweet-talked him or tried to coax him, he wouldn't smile. He even kept me up all night. I didn't get out of bed until late the next morning. When I woke up, I found that Noah hadn't gone to the office yet. He was smiling as he called me over for lunch. I couldn't help but think that jealous men were absolutely terrifying. Life became calm once more, and Victor stopped bothering me. Within two months, I received news from a friend about Whitmore Corp's bankruptcy. I learned that they were suspected of money laundering, and everyone had been arrested.

Kinks: CNC (Consensual Non-Consent), kidnapping, rough sex, being overpowered, degradation + praise, being used, forced orgasms, being claimed/possessed. She hesitated for a long time before hitting “match.” That same night, she matched with someone. Damien. His profile was simple: Damien Cross, 34 Kinks: CNC, kidnapping/roleplay, heavy dominance, ownership, rough sex, breeding talk, marking, aftercare. They started chatting. At first, it was cautious. Then it became intense. Damien: You said you like being taken against your will. How real do you want it to feel? Elena: As real as possible. I want to be scared. I want to feel like I don’t have a choice… but I also want a safe word.

Its purpose was obvious. I couldn’t speak. I could barely breathe. I just stood there, staring at the collar in disbelief. Its presence, combined with my lack of clothes and my virginity left no doubt in my mind as to the nature of the events about to unfold. I was the latest in a long line of beautiful young women to vanish under mysterious circumstances. No one knew what had happened to my predecessors, but I feared it involved a lot of pain. All I could do was play along. Either I would satisfy the boss so thoroughly he chose to let me go or I would die in the most pain-free manner possible. It was a grim through, but it was the only one that filled me with a meager sense of hope.