True Cross Dressing Stories Novels & Stories

This was crazy, what was she doing? Eddie had described the club at one time. The men often shed their suit jackets and shirts to walk about in their pants and boots. The women, he said, shed their clothes and walked about in sexy underwear or naked. It was as scandalous as it sounded. For Tara, matching underwear was a pipe dream. She was lucky to have clean underwear sometimes. It costs so much to wash clothes, so she often washed her stuff in the bathtub and hung it to air dry in their room.

Vladimir continued his story while Ashlyn listened carefully to him. “She told me to regain my confidence by wearing girls' clothing. I was confused but when she explained and showed me how it did, I started on liking it. She taught me well even how to control men or women from touching me. I like how it affects everything and I decided on cross-dressing ever since then.” he smiled as he finished his story about the reason why he was into cross-dressing. “Who taught you to wear a very big mask from head to toe?” Ashlyn curiously asked about the lady who help him to man up even though he was cross-dressing.

"I have to tell you something. And if you laugh, I will probably jump into the campus pool and never come out." He stopped walking, his hands deep in his pockets. "I am not gonna laugh, Gabe. Talk to me." "I... I have always wanted to be a cross dresser," I blurted out. The words felt like lead falling out of my mouth. "I love the way the clothes look. The silk, the skirts, the would make me feel... light and sexy. Not like a typical man who’s supposed to be serious all the time." I waited for the blow. I waited for him to call me weird. But Leo just looked at me. His eyes were dark, tracking the way I was fidgeting with the hem of my shirt.

In an instance, a group of girls were eyeing him from afar, and he winked naughtily at them, making them squeal. "Well, apparently they made a crossdressing cafe." Adam spilled. "Wow for real, man?" Taylor spoke in shock, his face twisted into a grimace. "Yeah, but they're not crossdressing and all, just wearing wig and some feminine looking outfits. Not that frilly maid outfit like the ones in the comic, yuck." Adam scoffed. The three of them then guffawed. Not long after that, they reached the cafe. The line was very long that they have to separate it into two lines.

JANE'S POV “Hey Jane, can I come pick you up tonight? I ignored the message because I wasn't interested. Spicy was too extra and he made me laugh the entire time. He started telling me about how some guys tried to do him dirty because he was a crossdresser and how he fought all of them for self-defense. He demonstrated everything and I was laughing, forgetting that it wasn't a comedy show. He fixed the wig and when I added a glimpse of myself in the mirror, I was looking like a 24-year-old baddie. He started my make up and in no time we were done. I was taken to another room to pick out some selected outfits, and I fell in love with the first outfit I tried. I didn't take it off.

The air still smelled faintly of old books and the cedar sachets their mother used to tuck into drawers. Nathan closed the door. Cole turned the lock. Isabel stood between the two beds and let the cardigan fall. This time they undressed each other first. She watched as identical bodies were revealed—same broad shoulders, same lean muscle, same dark trail of hair leading down. When they were both naked the resemblance became almost unbearable. Only the scar and the ring remained as proof that the universe had not simply doubled one man.

Christmas is only a few days away. ‘Well, I dildoed up.’ ‘You what?’ ‘Bought some strap-on stuff.’ ‘You are crimson.’ ‘Are you surprised?’ I squeaked. ‘And you look as though you have a hard-on.’ ‘Are you surprised?’ he growled and crossed his legs. ‘So, what happened?’ ‘I met him in a no-lights LGBT club. I pretended to be late, and while he was waiting, picked him up, as a bloke, seduced him, and him thinking I was a bloke, I took it up the – you know.’

Gold Mask pulls out, and I gasp for breath, then he slaps his cock across my face. “You’ll remember this taste when you sleep.” Then he grips a fistful of my hair and bends me over the pedestal of the platform, ripping my dress open. Very easily, my dress tears and I’m totally bare, exposed to their eyes. ... And Wet. He spreads my ass, showing me off to the other masked men. “She’s dripping,” he announces. “Look at her, she's a mess already.” They all growl at this and clap their hands to together, noisily showing their approval of my reaction.

Her one saving grace was that the tempo was slow enough for her to catch up with the others. Caitlin again scanned the crowd, hoping for a glimpse of Caleb. But with all the costumes and masks, it was impossible to even tell who was really male or female. Occasionally, long hair sprawled out the back, and that made it easy, but some women wore their hair tucked in, covered up by a high collar, and dressed in men’s clothing. And some men, Caitlin noticed, strangely enough, dressed in gowns; she could only tell they were men by the muscles in their calves. She had never imagined that there would be any cross-dressing in this century. Was there anything off-limits?

I wanted to see if I could make these two powerful men break under the weight of my own seduction. I pulled the dress from the back of the closet, a garment I had bought months ago but never had the heart to wear while Manuel was fading. It was a liquid fire red, covered in thousands of tiny, shimmering sequins that caught the light with every breath I took. The neckline plunged dangerously low, but the real statement was the back, it was entirely open down to the very top of my tailbone, held together by nothing but the grace of the silk. The slit on the right side spiraled up to my mid thigh, flashing pale skin with every step I took.