Justin Bieber/Jason McCann Imagines | Book One

First Time Hittin' That*

I felt something that I knew all along I would feel when my first time came. That feeling over being exposed and open with embarrassment, but some part of me felt okay because I was in the presence of someone I trusted.

When my underwear was off, the pressure that Justin's teeth applied to his lip increased drastically, so much that I thought he might bleed out. His eyes ran up and down my body. "Baby," He whispered once more. I felt my cheeks flush.

Immediately, the slight bulge in his boxers became noticeable and I found my breath quickening. His lips attached themselves to my thigh, he sucked gently.

He pulled away before he went any further, but his hand replaced his lips. I watched him innocently as his fingers danced across my skin and made their way to clit. He looked slightly unsure but not too insure that he couldn't lick his thumb and press it down onto my clit. He began to motion circles to which I gasped. His mouth rested between a smile and smirk.

The burn that his thumb caused in my stomach was something that never left me. It was something I had never felt and I wanted more. My hands gripped the sheets beneath me.

"Does that feel good?" He questioned. "Tell me if it doesn't." Watching me, his eyes scanned my face as though he was looking for any sign of uncomfort. His finger stretched down the whole length of my clit.

"J-Justin," I moaned under my breath while my eyes fell shut. "Mm." I took my lips in my mouth as I pressed my head further into the softness of the pillow.

He moved his thumb from my clit, disappointing me, and began to trail a finger through my wetness. "So wet already." He muttered. His fingers didn't leave my entrance, however. He pushed two fingers inside of me ever so slowly as his eyes watched my face.

I felt them. I felt them pushing up against my tight walls. I felt them stretch me. "Oh shit." I hissed as the feeling of pleasure, but a slight feeling of pain, ran through my lower body.

He took a firm hold of my hand and kissed it softly. "Remember that I don't ever mean to hurt you on purpose." He kissed the top of my hand once more
Pulling his fingers out of me, it was only seconds before he was pushing them back into me again. He hushed me kindly when I groaned. "You're so wet, that's a good thing, right? Hopefully it won't hurt as much." He took his hand away completely before climbing up my body.

He kneeled before me and took a hold of the hem of his boxers. I tried to hold the gaze I had on his face as he pulled them down but my eyes failed me. I caught sight of his hard on and my breath hitched at the size. He didn't notice straight away but as my eyes widened, he grinned. I tried to keep my eyes away as he jerked himself a few times, moaning at the back of his throat.

His boxers were discarded with the rest of the clothes we had thrown off carelessly.

On top of me, he smiled down as he positioned himself. "Ready?" He whispered.

Throughout the night I had forgotten many times that it was also Justin's first time too, simply because of how confident he was. I wasn't sure if that was just because he knew what he was doing somehow, or because he knew he wasn't going to be hurt.

I nodded, taking a deep breath. "A little nervous but I know I want this." I let my hands fall on his shoulders.
He kissed my forehead as he pressed into me slowly once he had struggled slightly to postion himself at my entrance. I hissed even at the feeling of his tip being remotely inside of me, and I found myself wanting to cry out already.

Further and further in he went, and the pain only increased. I felt the wetness around my eyes. "God, I'm so sorry, [Y/N]." He squeezed his eyes shut tightly. "I hate that this feels so good for me while you're in pain. I'm not enjoying this until you are too." I took a hold of his hand in mine, squeezing it softly. "I love you. I know it hurts, but this is supposed to be proof of our love for each other and it will be. Just wait. It's gotta get better, right?" He rambled on, but his voice was only a minor noise as I tried to block out the feeling of discomfort going on in my body.