Crossdresser First Time With A Man Novels & Stories

"A shiver ran down my spine. This was it. My first time. My very first time. And with a stranger… in a wheelchair. A wave of unease washed over me, a mix of fear and something else I couldn't quite name. "Come closer," his voice cut through the silence. It was a command, laced with… something. It made me feel small, like a kid being told what to do. Almost without thinking, I obeyed. My legs felt heavy as I walked towards him, stopping just in front of his chair. He looked up at me, his eyes held a fierce intensity. "Take off your dress." Another order. My heart hammered against my ribs. Was this really happening? I hesitated for a split second, then reached behind me, fumbling with the zipp

“He had this online romance. Kept bragging about his gorgeous ‘girlfriend’ on the internet. And yeah, the guy really was gorgeous—because he was a cross-dresser. A cross-dresser with a girlfriend. He scammed Greenie here out of enough cash to bankroll that girlfriend’s life. So technically, our boy here ended up being the other man. A very generous one.” The whole room started snickering. Lucas laughed even harder. “But wait—it gets better. The guy actually fell for him. Said he was moved by his… spending power. They started dating for real. And the cross-dresser? Could fake a woman’s voice. So Greenie went on dates, totally clueless. Until one night, he got drunk, dragged to a hotel, and—we

he said, his face indifferent. "Fine, I'll strip" I said, finally making up my mind. But after this, I'll quit. Slowly undoing my buttons, my bra came into view and I felt my face slowly turning red in embarrassment. This is the first time I've ever undress in front of a man. Taking off my shirt,I moved to my trouser and took it off before standing straight only in my panties and bra, my face red like ripped tomato. I closed my eyes, praying for this torture to end but I heard him say,

I became gay at the gym (6) As I knelt down on the bed, the wedding dress bunched around my legs. I turned over, laid on my back, and spread my legs for this amazing black man. The white dress covered my body, and only my white stocking covered feet could be seen. I watched, panting as Wayne began to strip,first his shirt and then his jeans. His body was like a work of art, the definition of a dominant man. His muscles bulged, and when his boxers fell, my eyes locked onto his semi hard, massive cock.

This would be my first time undressing in front of a man and I was nervous. I had hoped that we would talk first before getting down to the lovemaking, I hoped to tell him it was my first time and perhaps plead with him to be gentle. But I couldn't utter a word. His aura was too powerful and his attitude had shown me that he had no intention of caring for me. I heard him cuss under his breath, I couldn't hear the words but I felt the weight. It was violent. "Should I directly rip that fuckin dress off?"

The wolf then bent down, and I immediately jumped to the ground, almost losing my footing in the process. The wolf took several steps away from us before I once again saw it shifting. To my utter horror, I couldn't stop my eyes from raking all over his body until they finally landed on his groin. And that shameless man dared to put his hands on his waist, proudly flaunting his asset in front of me. Oh, Lord. I almost wanted to vomit at the moment. In my nineteen years of life, I never once saw a naked man. Sure, I cross-dressed for a long time, but I had tried my best to avoid the place where men would show each other's bodies.

As the cops slowly walked around the couch, they stood and lowered their hands behind their backs, putting the handcuffs around their wrists. "You can’t arrest me! I am not a criminal!" The man protested. "Tell that to the judge, asshole!" Xander snapped. He took off his wig and tossed it to the floor. It was revealing his blonde hair that made the man open his mouth wide in awe. "So…you are a man." The man said stunned. "You are a cross-dresser." He continued, blinking in disbelief. "Take them out," Xander stated, looking at the men with a lot of disgust in his eyes.

Part of me was jumping with happiness and part of me was asking why he didn't have a girlfriend "Why," "My job is to please all women, lie down," he said straight, he sounded cold and distant. I didn't ask any more questions but climbed on the bed "Do you have to tie me up?" I asked when he took the ropes and leather mask. It looked like he took his identity seriously "Relax," he helped me wear the mask. This was the first man I didn't feel shy exposing my body to. I was used to stripping at the club for men, but this man, I could spread myself for him without worrying

I gave him a firm nod of my head and in the next moment, he threw off his shirt and about to unbuckle his pants when I held his hand thus preventing him to go all naked. He gave me a puzzled look. "Let me undress you and you can do the same for me." I said. His eyes darkened. In a swift movement, he pulled me closer and slide his hand on the back on, I felt his fingers tucking on my zipper. I closed my eyes in anticipation. It would be the first time I'd be stark naked in front of a man. I remember my first time being guided by Colton, who dominated an inexperienced girl back then.

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.’