Crossdresser First Time With A Man Novels & Stories

“I mean, have you ever done anything remotely like this before?” “What?” he asked, making himself sound clueless before he added, “Made out with someone I just met twenty minutes ago, or put the moves on a complete stranger while wearing a dress and fake breasts? Yeah, no. Both are firsts for me too. But I gotta say, sharing them with you has been… Nice.” He stepped toward me, turning serious. “It's been downright amazing, actually.” The low timbre of his voice made my hormones shudder with wicked delight.

And then, the realization hit me that there was only one man who helped me until we did that. I frowned and blushed. It was my first time and the worst we had had a few times. When I noticed that I was wearing something else, I was even more embarrassed. I wore men's clothes, okay? Who is not ashamed? Maybe he didn't wear it on me, did he? It's not impossible!

This man needed to put a shirt on because his sweet words were only going to lead to something else. Creed’s nose flared, feeling the heavy heave of his chest rising. “Odessa,” his voice reverberated. Oh dear. The thick, calloused hands wrapped around my waist, having me straddle his nakedness. I was equally so. The heat of his member resting on my thigh, he pulled the sheets away from my chest. Why I had become so shy just because he could speak, I wasn’t sure. Maybe it was because he could express his opinion now. The night we first made love, I felt the same. Arms crossing my chest, his eyes stayed on me, pulling my arms down.

I tried to follow but the other man put out his arm. “Not you, Red…” He said, unzipping his fly, “You start here.” I looked around, the sun was down but the neighborhood was well lit. Cars were passing the house and a couple was walking their dog. “I’ve never done anything like this in public.” I said, trying not to show how nervous I was. “First time for everything, Red.” The first guy said, unzipping with a smile. I thought about June’s advice, I had to make this fast. I dropped to my knees, licked my lips and locked eyes on the two biggest cocks I’d ever seen.

It was really a big deal for him not just because it was the first time he dipped his stuff into a woman, but it was actually a girl he had really admired for a very long time. My first was a little different. It was about two months before Kelvin had his. I was at a friend’s party and ‘smuggled’ drinks were moving around. A girl whom I had never seen before started acting funny with me and since I was half drunk, I willingly played along. It got to the point, where she had pulled my hands under her skirt, trying to get my fingers in her vagina. My hands had been very shaky, so she hadn't enjoyed that much.

"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.

My coworker found out my girlfriend was a wealthy heiress, and he saw his chance to worm his way into her bed. Two months later, he strutted up to me with his nose in the air. "Your girlfriend's pregnant with my child. Do yourself a favor and back off before this gets ugly." Whose child? I froze. The problem was, the wealthy heiress "girlfriend" he kept talking about was actually a man. So whose baby was it?

I burst out laughing, took hi long enough to confess. It was my first time too — at least, my first time with someone who made me feel this way. I had never had any intimacy with a man, women… yes, men… no, so it would be my first time being with a man. “We would take it slow and steady” I said as I undid his belt and buried my face to suck him. ***

He said his girl friend hadn't worn her set yet and it was nice to see it on someone and asked me to take off my t shirt which I did. I was trembling nervously. I have cross-dressed for years and no one has ever seen me dressed. He asked if he could touch the satin and I anxiously said yes and my cock began to swell. he placed one hand on my back and slid it up and down and in circles and said "I love the feel and look of satin, it drives me wild." He hand slid down to my butt cheeks and I shivered. Then he reached over with his other hand and slid it across my stomach and up my chest and used to fingers to tease my nipples. I almost melted. By now, my cock was pushing the tap panties straig

I was so excited and shocked by the moment that I froze, not knowing what else to do other than stare with my mouth agape. The older man took my hand and wrapped it around his thick cock. I licked my lips when I felt how hard and warm his shaft was. I had never done more than kiss a man before, Mr. Miller's fat cock was the first one I held and--God, was it amazing. When I squeezed a little and took over stroking it I heard my best friend's dad groan and I gasped, feeling the power I had held in the palm of my hand. "That's it, darling... stroke Daddy's cock... just like that..." He whispered as he leaned over me. The small gold crucifix he always wore dangled from his throat.