Crossdresser First Time With A Man Novels & Stories

For now, at least. I pulled on my clothes slowly, my jeans rubbing against my sore knees from kneeling on the hard floor. My mind kept flashing back to how the masked man’s hand yanked my hair, that thick shaft of his pounding my throat and the way he'd hold it there until stars burst in my eyes. I was a virgin in both holes and had never even kissed a guy before. And yesterday? My mouth getting deflowered so roughly by a stranger was wrong, so fucking wrong but at the same time, it was so hot.

Was he affiliated with Cross? I reached out toward his shirt. He grabbed my wrist. “What are you doing?” he asked. I ignored him. Our eyes locked, and a tingling sensation rushed through me. I kissed him. He didn’t hesitate. He kissed me back, his hands sliding over my waist, pulling me closer. Fuck, what am I doing? I dropped to my knees and unfastened his belt. His cock sprang free—hard and ready. It reminded me too much of Cross. I braced myself.

If he really wanted, he would have but after a few half hearted attempts, he surrendered to the pleasure building up in the both of us as we kissed and caressed. Soon our shirts were thrown mindlessly away and our trousers too. The boxers was next when suddenly,his movements stilled and his body became tense. I looked up at him and saw how scare and unsure he was and knew this must be his first time with a man. 'Don't worry', I said. 'I got this. You should not be scared of experimenting and embracing this, I got you covered'.

This was gong to be my first time and what if I messed it all up? I inhaled deeply and closed my eyes, then opened it and got on my knees. I didn’t wait for him to say what he wanted. I already got the hint. I struggled a bit with his belt before I was able to undo it, then I undid the buttons and unzipped the zipper. I took out his cock and gulped at the size. Holy…. It was huge. Very huge. I looked up at him once again, rethinking this whole thing but he stared me down. I touched it tentatively. This was my first time being around a man in such manner, and, gods. He was so huge.

My palms were all sweaty and my stomach tugged in a tight knot. Was I actually nervous about seeing him again? I freaked out, yes, but it was only natural. The first time my lust had taken over me was when I was off age to live on it and boy it wasn't pretty! This was the second time in my life it was happening again and unlike the first, the demons knew what they were getting into. Cross has no idea and I didn't plan for this. Plus, I let him hit the ground when it was clearly my fault he couldn't walk.

I was 22 years old after all. “I need him to see that I'm grown enough to handle the business.” I looked at Anthony's lips as I spoke, my hot breath washed against his face. His hand was still buried in my boxers. Even though I was a crossdresser, I preferred boxers to panties. “You are.” Anthony smiled. Leaning against me, he pressed his lips into mine, while his hand continued working on the bulge within my boxers. I could feel the fabric getting soaked with precum.

Marco explained, loosening his tie as he then disappeared into the en-suite. The moment he half closed the bathroom door, I quickly darted over to the closet and pulled out the first set of bedwear I could see and practically ripped off the dress that I had felt so claustrophobic in all day. I hurriedly got dressed into my shorts and top, then chucked the dress into a corner of the room. But as I turned around and looked down at the bed, another wave of angst made me shudder. Not only had I never had sex before, in fact I had never even properly kissed a man either. The last time I kissed a male was when I was thirteen and it was with a boy I once had a crush on, it was just an innocent and

"There's some sweat pants and shirts in that bottom drawer. They should work for you. They'll be big because they're mine, but it should be comfortable." This was something she had never really done before, wear a man's clothes. It was special, it was the hallmark of a relationship, and she knew that she was falling headlong into a very serious one with this man. She watched as he disrobed down to boxer briefs and then pulled the covers back. Shyness overcame her from somewhere deep inside. "You know I've seen it all right? Harley weekend?"

“Yes. I want you.” And that was it. He climbed on top of me and pressed his mouth against my neck. Down south, I felt the head of his dick at the entrance of my pussy. Being the tease he was, he pushed my folds apart as he ran his dick along my slit. I pulled my lower lip in between my teeth. “Tell me,” he spread my legs apart some more. “Has anyone made you this wet before?” I shook my head. He was the first man to ever come this close to having sex with me. I’d masturbated with my fingers, but never a dildo. I wanted him to be the first to have me.

I only wore a thong so I could pleasure myself at any point of time. I never expected another man to see it. What should I do? I kept trying to free my head, but it got tighter instead. I could not free myself. The man grew more excited as he kept rubbing my bottom. I felt worked up from the sensation. He even trailed a finger between my legs. It felt a little itchy. It had been a while since a man had touched me, so it felt as though it was my first time. “This is so tight. It’s so rare for a massage parlor to have someone so inexperienced.”