Sleeping With My Best Friend - (Complete)

Chapter 15 - The First Time

Dean hovered over her, looking down into Berkley's eyes for a few seconds before he slowly leaned in closer and stopped when his face was an inch from hers. He glanced down at her lips and hesitated, looking back into her eyes before finally closing the gap between them and pressing his lips softly against hers.

She closed her eyes and felt her insides flutter as he kissed her. This felt different than the other kisses they had shared earlier. The others had been emotionally shallow and half-hearted, but it seemed like they were both more present and into it now. Maybe she was just imagining things and reading too much into it. She tried to block out those thoughts and focus on what was happening instead.

Dean turned his head to the side, covering her mouth completely with his and kissing her deeply as she slowly lifted her legs on either side of him, spreading them slightly while he lowered his naked body down onto hers. Feeling their bare skin coming together made her heart race with adrenaline and her breath got more shallow. She couldn't believe this was really happening.

As she kissed him, her hands came to rest against the smooth, tan skin of his firm, broad shoulders as he laid the full weight of his body down onto hers. 

She felt his hard erection pressing up against her stomach and that made her ache to feel him inside her. Judging by how painfully hard he was, it was obvious he wanted her too.

"Are you sure about this?" he whispered breathlessly against her ear and she swallowed hard before nodding.

"Yeah, I'm sure," she whispered back.

He lifted himself up on his arms and reached down between them, taking his hard length in his hand and guiding it up and down against her folds until he found her entrance. Then he lifted his head and looked down into her eyes, studying them to make sure she was okay as he pressed his hardness against her opening, slowly breaking through the seal.

She sucked in air and then held her breath, biting into her bottom lip as she looked up at him nervously, gripping firmly onto his shoulders. As he gradually pushed his way inside, stretching her out to accommodate his size, it became uncomfortable and she winced in pain.

"Are you okay?" he asked, stopping.

"Yeah," she said breathlessly, nodding. "Just umm. Just go slow."

He hesitated before slowly pushing in a little further and she closed her eyes and bit into her bottom lip when it started to hurt. He stopped again and looked down at her.

"I'm sorry," he whispered. "I'm ummm. I'm a lot bigger than the average guy. I probably should have warned you about that ahead of time."

She looked up into his dark blue eyes and gave him a weak smile. "It's okay," she whispered. "I knew my first time was gonna hurt, but it's okay. I'm pretty sure I can handle it."

She trusted him and knew he wouldn't hurt her. He was even more protective of her than her own Dad and brother. That's one of the reasons why she had wanted her first time to be with him.

"If you need me to stop again, just let me know," he whispered, before he leaned down and gently pressed his lips against hers as he slowly pressed in farther.

He hit a wall and pushed through it, giving her an uncomfortable prick of pain for a second, before he finally finished burying his hard shaft all the way inside her, filling her up completely.

He held it in that spot for a minute, so deep inside her that she could feel his length hitting the back of her insides, and it gradually started to feel really good. He shifted and pushed himself in even deeper, pressing harder against that spot before he slowly started to move in and out.