Crossdresser Humiliated Novels & Stories

“Since you can’t pay, then take off your clothes instead. One outfit for another. Fair trade, don’t you think?” His voice wasn’t quiet. Conversations faltered around them. Heads turned. Laughter rippled through the crowd. Heat drained from Isabella’s face. She only owned a few uniforms to her name, and underneath, she wore nothing but thin undergarments. He was deliberately humiliating her. “What’s wrong? Isn’t your shabby uniform worth trading for hers? Or are you too proud?” “Mr. Pei, she’s no fun at all. Won’t even take her clothes off…”

Benedict looked at me, his tone as matter-of-fact as ever. “Get a ride home. I need to send Anna back to her place.” I lowered my eyes and remained silent. Benedict had a severe obsession with cleanliness and never allowed any lingering scents in his car. Once, because of his stubborn temperament, he had offended a client. I nearly drank myself to death just to apologize on his behalf. Yet afterward, he frowned at me with open disgust and said, “You reek. Figure out your own way back.” That day, he abandoned me alone in the snow-covered outskirts of the city.

And even if she can fork out cash from the Cross Group, it would be impossible at the moment because of her on going project. When the media spotted the now almost homeless Rex Cross that looked pleasant to the eyes, they started to take photos of him. However, most people eagerly took photos because they noticed that he might have worn high quality fakes to attend the wedding banquet. There was no way the Rex Cross now can afford a suit that expensive. They were curious and they found the scene embarrassing for him, so they took lots of photos. When Daniel saw that Hilda's new boyfriend came dressing in high quality replicas, he found it understandable.

So, Over the next couple of years, I started cross dressing & playing with big black toys, until I just couldn't take it no more. Then I found the M4T personals on Craigslist & quickly hooked up with another Big Black Cock, who fucked my now totally broke in ass pussy. Over the next few years I hooked up with another 10 Big Black Cock's, who I dressed up all sexy for & had them just fuck my ass pussy, with some of them even cumming all up in me too.

But if that is what he wants to see me in, then why not? I take the swim wear from his hand with a smile, disappear behind the curtain and hurry to get undress. One part of me is hoping that he would come back here so we could fuck, but I guess we have to have respect for these people and their store. When done, I go to show off body and the tiny clothes that are covering my private areas. Mr Cross runs his eyes over my body with a look of approval. And I do a little twirl. "Good, let's go."

I was done. That moment in the lawyer’s office was the last thread of his self-control snapping. The second we walked out, the insults started. He called me every but the child of God, as if degrading me would somehow change my mind. As if it would make me love him again. Then, a few days ago, I made the mistake of dressing nicely, really nicely. I wore a long, fitted black dress that hugged every curve, showing just a hint of cleavage. My flat stomach, my defined hips, my thighs, and my ass, it all looked good. And I knew it.

Ember commands once the dress is off, and I'm left standing there in my underwear. Taking a deep breath, I steel myself for what lies ahead. My insides churn with a mixture of humiliation and anger as I slowly approach the exit. The thought of walking out wearing nothing but my underwear fills me with a sense of profound discomfort. I grasp the doorknob, but my hand hesitates, unable to find the strength to pull it open. I'm a princess, fuck it. I shouldn't be seen in my underwear.

“Unless… you’ve been selling yourself, haven’t you? Got some rich old man to buy these clothes for you? Because we all know what you are, Lila. A gutter rat with no class and no life.” The words crash against me like waves. And when I glance around, I see people nodding. Murmuring in agreement. The judgment in their eyes burns. And Liam… he just stands there. Watching. Letting it happen. Never in my life have I been humiliated like this. Why? Tears roll down my cheeks, hot and fast. “No… That’s not true,” I cry out. My voice cracks under the weight of it all. “You’re lying, Claudia!”

It took everything in me not to scream, but I managed to compose myself. ‘Ladies, remove your clothes’. My head snapped up hearing the elders' words. He can’t be serious. My quick movement caught the attention of the tall blonde on the right of the elder, the one standing in front of me. ‘Problem?’ He asked with a smirk, folding his arms. I just looked back down at the ground. ‘He said remove your clothes, slut!’. I could hear the venom mixed with entertainment and humour in his words, he liked to humiliate people. I wouldn’t give him the satisfaction. I did as I was told and took my clothes off, the young girl next to me followed my actions and once they were all removed, I tried to cover m

He groped my boob so tightly like he will tear up my flesh any time. He groped my whole body shamelessly and humiliated me. He spanked my butt few times and said many dirty words about my body where I was just standing like a robot. Tolerating his humiliation I am feeling like to kill myself. Then he said like a shameless man," Lay down on the couch and spread your legs. I want to fuck you now." " Sir, I beg you. Not here. It's really uncomfortable. We are in the office," I pleaded with my teary eyes.