Crossdresser First Time With A Man Novels & Stories

He followed seconds later, groaning as he pulled out and came across my thigh. I slid down the wall, panting, legs jelly. The second man knelt, offered himself gently. I shook my head—no more tonight—but the invitation hung there. People murmured approval. Someone clapped softly. I pulled my jeans up with trembling hands, mask still hiding my flushed face. My body hummed, sore and satisfied and terrified all at once. This was my first time. And God help me, it felt so fucking good.

I struggled to push him away, but my strength was too small for this man, not to mention I was still drunk. "This... is this your first time? Are you a virgin?" The man seemed even more surprised than I was. He stopped when he saw a streak of red blood oozing out, his "thing" didn't move either. "Sorry, I don’t know that. I was a bit rough and hurt you. I'll pay more attention." The man kissed my forehead, then licked my cheeks, swallowing my tears. I gasped, trying to calm down. He is also waiting for me. His "thing" is hard, hot, and very loud. It makes my lower abdomen stretch.

I didn’t want the matter to escalate to the police or become public. As I finished the dishes and came out of the dining area, the entrance door was forcefully flung open, slamming against the wall. When I saw who was standing at the door, I was rendered speechless. The person was tall, wearing a wig and a red gown that barely covered his thighs. His awkwardly worn heels and the makeup couldn’t hide the fact that he was a man, despite his pretty appearance. When did we know a cross-dresser? I blurted out, "Who are you?"

After tossing the bottle on the bed, I walked through the mist and hoped it would mask any lingering scent Silica might have left behind. Opening the door, I came face to face with Zy. He sucked in a sharp breath as his eyes glided over me. Shifting from one foot to the other, I became subconscious about my appearance. I usually dressed for myself, but this was my first time dressing for a man. My father didn’t count, as he often said I would look good in a trash bag if I wanted to wear one. “Is it bad?” My hands tugged at the sides of my dress.

From knowing it would never be the same after this. “You’re going to beg to cum,” the man said. “And I’ll still say no.” He turned the dildo slowly inside him. The mechanic’s knees buckled. He cried out, legs shaking, pre-cum dripping onto the bench. “Not yet,” the man said. He pulled the dildo out. Pressed it against the back of the mechanic’s neck. Cold. Marking him. Then he undid his belt. The sound made the mechanic’s cock twitch. “First time with a man?” the stranger asked.

Clarissa bravely said to the man. “Oh, so you noticed me, sweetheart. By the way, allow me to introduce myself. I am Bamby Flores.” The man offered the information himself. “So what can I do for you, sir?” Clarissa repeated her question. She noticed how flamboyant the clothing this man was wearing. In fact, he’s not wearing the typical clothes a man would wear – he was wearing women’s conventional apparel and accessories. Unsurprisingly, he was into these six-inch red stilettos. This man could be considered gay, Clarissa was thinking.

To my horror his released member had bounced back to full erection. This man wasn’t human! No way. He climbed over me and I instinctively fell on my back, his lips started those mouth made wonders again as he trailed kisses and bites all over my body, moving from my lips to my chest and abdomen. He moved up to whisper something to me, “I’m letting you experience this because it’s your first time. So I’ll go easy on you. But don’t expect this moving forward.” I gulped as he released my ears and went back down, all the way down. Should I be thankful to him that he didn’t strap my hands and feet?

maybe because this was the closest we were that I could satisfactorily examine the woman's face. Grace opened her jacket in a bit of a hurry but I immediately stopped her. "Let me do it," I said. This is my first time having sex. even though I did it with my own friends. I don't want to miss even a second of this beautiful moment. Grace was so resigned when I stripped her clothes one by one. It seemed that the woman was deliberately always wearing baggy clothes to hide her beautiful body. I even ran out of words looking at Grace's body.

“Fuck. Perfect. Come here, sweetheart.” The limo started moving through the city lights as Damien pulled Alex onto his lap. For the first time in his life, Alex felt another man’s hard cock pressing against his ass through their clothes. “You are shaking,” Damien murmured, running his hands up Alex’s smooth thighs. “First time dressed like this for money?” Alex nodded, biting his lip. “Yes, sir.” Damien chuckled warmly. “Good. I like breaking in new girls. Or should I say new boys?”

“I’m not one to stop myself in the middle of something fun, but… you’re a virgin. Are you sure you want to do this?” He wasn’t wrong. I had never gone this far with anyone before. But for some reason, I didn’t care. He didn’t wait for my answer—he seemed to already know my thoughts even before I voiced them out. In one swift motion, he pulled off his shirt and trousers, climbing onto the bed above me. His gaze softened slightly. “I’ll go easy. It’ll hurt at first, but trust me—you’ll enjoy it afterward.” And just like that, I gave myself to a man I had met in a club for the first time.