Crossdresser First Time With A Man Novels & Stories

He pulls down his boxers, revealing his large member to my curious eyes; in the darkness his anatomy looked monstrous. — I couldn’t believe a man could be that long. Seeing it so thick and erect made me swallow hard. — You’re scared, don’t be afraid — he says smiling — you act as if it were your first time or as if it were the first time in your life you’ve seen a cock — the man tells me. — Obviously it’s my first time — I think to myself — I had never been like this with a man, well, except that one time Alexander tried to rape me, but that doesn’t count for me.

A vivid image flashes through my mind. “It’s the Cros-High Club... not Cross,” I whisper. “No...” He smirks, his eyes darkening. “It’s Cross. Trust me.” Something inside me breaks loose, and suddenly I want to say something reckless. I lean closer and whisper into his ear. “You know, I’ve never fucked a stranger before.” He inhales sharply as our eyes meet. “Do you want to fuck a stranger?” he murmurs as the tension between us grows stronger. I stare at him.

The beautiful woman excitedly clamped her legs together, squeezing my neck between them. It was my first time doing something like this on the street with a stranger. I was so electrified that my whole body trembled, and I accidentally thrust at the wrong angle. She let out a muffled groan. "Mister, you're so hard and hot down there." I adjusted myself, ready to go again. But then, the woman grabbed my member and guided it toward herself. Holy crap! She was super forward, alright.

Damn, this man never let anything get past his nose. His hand came up to stroke my cheek delicately, as though his words and actions were two separate things. Mustering courage to speak, I said, “I… I want you too. Hell, I can’t stop thinking about you. But I haven’t been with a man before.” His hand on my cheek froze. “It’s your first time?” I nodded, swallowing hard while I watched for his reaction. Was he going to back away, or was he going to take me regardless? What was his response going to be?

My chest rose and fell too quickly, nipples hard beneath the lace, thighs pressing together in desperate friction. “Spread them,” the first man said, his voice a husk of control. My body obeyed before my mind could catch up. The dress pooled further, and the lace of my panties was exposed to both sets of eyes. “Fuck,” the silver-masked man whispered, dragging a hand through his hair as though restraining himself. The first man knelt in front of me, his hands firm on my thighs. He pressed them wider, his masked face lowering until his breath fanned hot against the thin fabric between my legs. I gasped, clutching at the silk sheets with shaking fingers.

I think about it for a second then I decide that I’m going to do it. My core clenches at the thought of having sex for the first time and I become more aware that I want to do this. “Okay”I tell him and I walk back to the room locking the door.I take off my dress and then walk towards the random stranger who is beckoning me with his finger. This is so fucked up but I’m determined to enjoy this so I don’t pay too much attention to the details because that’ll only make me overthink this. Besides all I ever wanted was to lose my virginity to Shane Ryder but now that he is balls deep inside of Clare Haistings I don’t think that matters anymore.

His dick was also growing bigger. Fear grew in my chest. Worry mixed with it. I pushed down the reluctance in my heart and leaned forward. My lips parted, slowly taking in the light brown shaft. "Oh~" Leander moaned. I lifted my head slightly, and my fingers wrapped around it. "Is it okay?" It was my first time doing this for a man. No matter how hard Vesper begged in my last life, I had never agreed to this as I felt it was too dirty. Alas, I was right. Vesper was indeed too dirty...

I almost tripped on my feet as I was shoved forward, trying to ignore the ache in my pants from what I had taken. Fuck. The man stretched a hand. “Ace. First time?” I nodded, feeling my words fail me. “Yeah.” The worker on set checked everything again, adjusting the sheets on the bed before gesturing for Ace to lie down. He sat back on the bed, pulling down his pants before shifting back, his zipper echoing in the space harshly before he pulled out his cock. And holy shit. My legs weakened. This was my first time doing anything like this. And that size? That would hurt like hell.

Her figure was defined and very alluring. She greeted me with a bright, warm smile and said, “Hello.” I was so nervous that my throat felt dry. It was the first time I had met the female streamer that I liked so much. I was speechless, so I just looked down and pretended to straighten my clothes to hide my awkwardness. When she seemed to notice how flustered I was, she gently ran her hand through my hair and said jokingly, “Don’t be nervous. I don’t bite!”

He began to actively look for opportunities to meet me by chance. At that time, I thought it was God's favor that I managed to see him each time. It turned out that he had planned it all along. Tonight was the first night we slept together. In the past, we had always done it over a video chat. This time, I was able to touch him and smell the scent of shower gel on his body. It was a little nerve-wracking for me to sleep with a man for the first time. Calvin smiled and calmed me down by saying, "Don't be nervous. I'll be gentle."