~~~ Your My Colors ~~~ Laughing Jack x (OC) Reader (Under editing currently!!)

~Chapter 16~ (Lemon)

Jack stroked his member a few times gently, and was finally hard enough. As he positioned himself in front of my entrance, he looked up at me. "Are you ready?" He asked, giving me a warm gaze. "I-I'm n-nervous......." I stammered, shaking slightly and blushing profusely. He smiled at me warmly. "Relax." He replied softly and he gently kissed me again passionately. We separated and he gave a small smile. "Give me your hands." I looked at him confused but before I could ask why, he spoke again. "Just trust me." I sighed, and opened my hands beside me. He gently placed his hands into mine, and intertwined them. "I won't let go." He purred softly, and I blushed as we shared another kiss once more. He gave me a soft smile once he broke away from me. "Ready?" I nodded and lightly squeezed his hands. He gently placed his head into my neck, as I felt his hands squeezing mine in return. "This may hurt just a little, lollipop." he murmured. I could feel him rubbing against my entrance. I was shaking. "J-Jackie......" I stuttered. "I-I-AH!" I gasped with a painful yelp as I felt him slowly start pushing his member inside of me. "AHH!" I cried in pain and squeezed his hands tightly. Tears stared to form in my eyes, causing my vision to blur. I could feel my womanhood stretching as he pushed in more. It was painful. He groaned and squeezed my hands tightly. He was still pushing in, and I could feel him stretching my walls. It hurt so much. "I-It's......okay......." He panted, gently nuzzling my neck. "R-Relax......." I whimpered, tears slowly sliding down my eyes. "I-I-AH! I c-c-can't!" He tried to ease it, but still continued to slowly push into me.

Laughing Jack's POV~~

Once Amy nodded that she was ready, I gently squeezed her hands before rubbing myself against her vaginal entrance. I was throbbing due to how excited I am. "J-Jackie......I-I-" Amy didn't get to finish, as I gently but slowly pushed my tip past her flaps and into her entrance. "AH!" I heard her cry in pain and I felt her squeeze my hands more tightly. "AHH!" I gave a small gentle push and I was able to push my tip inside. It hurt me to hear her cry in pain. I groaned softly as I continued to push in. I was feeling pain as well. I could feel her walls stretching as I kept going slowly. I squeezed her hands tightly as I breathed heavily. I could tell it hurt her a lot. "I-It's........ngh........okay........A-Amy........" I panted lightly as I nuzzled her neck lovingly. "I-I'm.........a-ah.........almost in.........just.........r-relax........." I could hear her breathing heavily. "I-I-AH! I c-c-can't!" I could feel her walls tearing a little and I heard Amy whimpering. I knew she was crying. I couldn't bear to hear her like this. I had to push all the way in. I gave one final gentle push, and I was finally inside of her.

Amy's POV~

I tightly squeezed his hands more, as I tried to bear the painful feeling. I could feel my walls tearing. I-It was too much! "J-Jackie, I-I-" I couldn't finish, for he gave one final gentle push and he was fully submerged inside. "AHHHH!" I cried out once more, as I felt agony going through me. I could feel stings and burns inside of my vagina. I-It's so painful! I was breathing heavily and my heart was racing. I........I was losing it. I was losing my virginity to Jack. I could feel blood running down my thighs. I knew my hymen broke. He broke through it which was causing me to bleed. I whimpered softly as I tried to bear the feeling. I didn't think it would hurt this much! I felt even more tears slowly roll down my cheeks. I closed my eyes and squeezed his hands as tightly as I could, as he laid down on top of me.

Laughing Jack's POV~~

I laid on top of her gently and tightly squeezed her hands. I didn't think she would feel this tight! I was feeling the same amount of pain she was. I was groaning softly but I still never let go of her hands. I could feel something run down her thigh. She was bleeding. That meant I broke through her hymen. I knew. She was losing her virginity to me, and I was losing mine to her. I could also feel her shaking and hear her whimpering softly. I could tell she was crying. She was hurting badly. It pained me to hear her like this. I needed to make sure she was okay before I moved. I looked at her. "A-Amy......" I watched as tears fell from her beautiful eyes. I gently wiped her tears away. "I-It's.......o-okay........d-don't cry......." It hurt me so much to see her cry.