My First Time Novels & Stories

[TRISTAN’S POV] He pushes back against my groin, grinding into me like he's trying to burrow through the fabric of my pants. "Raw. Hard. Rough. I want to feel it till I die. Because this is my first and last time doing this." Jesus fucking Christ. His first time. I can feel that information hit my bloodstream like heroin. This perfect, blonde boy who's never felt a cock inside him, asking me, a man he met ninety seconds ago, to take what's never been taken before.

“You’re my first. I just took the ad last week.” Great, I thought. I’m a virgin again. And a guinea pig. And stupid.

He grabbed my thighs and pulled me closer to him, his presence overwhelming. He brought his dick to my entrance and teased me with it, my heart raced, and a wave of fear swept over me, I didn’t know if I could handle this. I tried to steady myself, holding up my hands. “Please, I know you are used to it fast and raw but this is my first time .” I admitted, my voice trembling.

Huuft, this is the first time in my life that I feel like I've been caught red-handed. Embarrassed. *****

“Don’t be. I won’t hurt you. I’ll be gentle—it’s your first time.” My breath caught. How did he know… it’s my first time?

She gasped in my arms when I thrusted in, just by an inch. I raised my face with a groan when felt her walls tightening around me, gripping me immediately. “You are so tight, baby,” I quickly kissed her lips and started taking deep breaths, trying to remind myself that this was her first time, Grunting to myself, I moved one inch further and waited. A cry fell off her mouth and a drop of sweat slid down my temple. My hand reached up to wipe the tears off her face, trying my best to be gentle with her.

“Leopold…” his name left my lips as he made his way back up to my lips, claiming them once again. He positioned himself between my legs, and I felt the pressure of him entering me for the first time. I had never had sex before and wasn’t sure what to expect. I didn’t really have any friends to talk to about this thing; it’s not like I had a mother to give me the talk, and my father was too proud to deal with something like that.

"That was quite a memorable first experience." Suddenly, her head lifted up from the ground and she turned to face me. "First time?" she asked, sounding confused. "What do you mean?" I looked her straight in the eyes and explained, "That was my first time... you know, having sex, doing it, the thing we just did together." She was speechless. "Are you serious?" she asked, incredulous. "Yes, I'm not joking," I replied with a laugh. "That was my very first time."

I mumbled but he managed to hear what I said. "Then what is it about?" He asked gently, while his hand was on my arm tugging me to face him. "It was my first time and I felt like I wasn't good enough," I blurted out without carefully going through my words. I was suddenly met with silence, Glen's hand froze on my hand immediately then I quickly turned to face him, he wore a confused yet worried look on his face. "Are you okay?" I calmly asked. His gaze wandered to my eyes then he suddenly gripped me gently, "did you just say this is your first time?"

He tightened his grip on my thighs as he ate me out, and the whole time, he was staring at me, fueling his desire. His tongue teased my entrance before I felt his finger press against it. “Hmmm… Yesss.” I bit my lower lip hard. “Ahhhh…” His finger slid in. “You are so tight,” he whispered, and I opened my eyes and looked at him. “It’s my first time,” I said. At that very moment, he stood still, his eyes widening.