《Sleeping With My Best Friend (Complete)》Chapter 5 - The Indecent Proposal
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The next morning Berkley woke up to light streaming in through her little dorm window. She took air in, slowly blinking her eyes open as they adjusted to the light, looking around as her brain became aware of Dean's body cuddled up closely against hers from behind with his arm wrapped tightly around her waist. He had spent the night over at her house thousands of times before and she had even woken up to being cuddled by him, but today felt different.
Her eyes shot open when she realized what was different. His penis was rock hard and he was grinding it against her butt cheek. As she stirred to move away from him, his arm gripped her tighter and his hand slid under her shirt and cupped around one of her breasts and started massaging it as she heard him groan against her neck. She froze. Was this really happening right now?
"Dean?" she whispered. No answer. "Dean!" she shouted.
She heard a groan from behind her as he stopped moving and then he suddenly jerked away from her, falling off of the bed onto the floor and then he scrambled to his feet, looking shocked as he realized what he had just done. His eyes were wide and he looked at her in the bed for a second as his still half-asleep brain was processing what just happened.
"Fuck! I'm so sorry Berkley. I didn't mean to do that. I was having a dream and it felt so real," he said, his face flushing red with embarrassment.
Her eyes left his face and looked down at the large bulge standing straight up in his boxer shorts and he looked down realizing what she was looking at. He covered himself with his hands and then grabbed one of the pillows off her bed and held it in front of himself.
He grabbed his pants and shirt off of the floor, putting them on really fast before saying he'd be right back as he headed out the door. A while later he came back in the room acting nervous.
"Look Berkley. Can we just pretend this morning never happened?" he asked, rubbing a hand through his brown hair. "It was an accident and I don't want things to be awkward between us."
"Of course ........ we can't," she answered with a mischievous smile. "You know I'm gonna have to give you shit about this for the next several years. And just when you think I've finally forgotten it I'm gonna bring it back up again."
"How did I know you were gonna say that?" he laughed, tossing a pillow at her face that she blocked.
"Because you know me better than anyone else. That's how," she answered, getting up and grabbing some clothes out of her closet and her shower caddy. She turned and looked at him and laughed before closing the dorm room door.
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As she took a shower she thought about the fact that if it had been any other guy that had felt her up while she was asleep she would've kicked their ass, but she knew Dean well enough to know he wasn't trying to cop a feel on purpose. It was obvious he was just dreaming and the shame and embarrassment written all over his face afterwards showed her he regretted it. She trusted him completely and was closer to him than anyone else and she knew without a doubt he would never do that to her.
It got her thinking that maybe Ember was right that he would be a good person to practice with for her first time because she was so comfortable with him and he was safe. She decided she would talk to him about it and see what he thought. She straightened her hair and decided to leave it down today for once. She normally only did that for special occasions but today she just felt like leaving it down. She put on a pair of her favorite capri sweatpants and a baggy off the shoulder sweatshirt with a black sports bra underneath.
When she went back in her dorm room Dean was already dressed in a pair of dark jeans, a black t-shirt that was tight enough to see his muscles and some Nike high top tennis shoes. He was looking good as always with his tousled short brown hair and his dark aviator sunglasses on. He was one of those guys that always looked good without even having to try.
"Hey ummmm. I wanted to talk to you about something. I decided I want to tell you what Ember was talking about. I don't want to keep it a secret any more."
"Really? Good. The curiosity has been killing me."
She sat down on the bed and patted the spot beside her and he sat down too.
"So what's up?" he asked.
She took a deep breath in and let it out, gathering up the nerve to tell him.
"Ok. So Ember had this crazy idea and I immediately told her no but I'm starting to think maybe she was right. She thinks that I need to lose my virginity and just get it over with, like ripping off a band-aid."
He scrunched his eyebrows, apparently not liking the sound of that. She looked down at her hands that were toying with the fringe on her blanket nervously.
"She thinks I need to do it with a guy that I trust and have known for a long time because it would be better than doing it with a random stranger that might turn out to be a bad guy. That's what happened to her for her first time. She said if she could go back in time she would have done it with her best friend instead of someone she barely knew."
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He looked at her and said, "What are you saying? You want to have sex with me?" he asked, laughing awkwardly and rubbing the back of his neck, looking down. "Ummmm. I don't even know what to say to that."
"Think about it Dean. I have no idea what I'm doing so if I just go sleep with some random guy I'll totally make a fool of myself. I'm comfortable enough with you that I don't care about that and you've got lots of experience so you can teach me. I wanted my first time to be with somebody special and who's more special to me than you?"
He laughed and shook his head.
"No way Berkley. It's not happening."
"Why not? Give me one good reason," she said, crossing her arms.
"Because," he laughed. "You're you and I'm me and that would be so fucking weird. You're my best friend."
"So?"
"So, I don't look at you sexually but if we had sex I would start to and that would change things between us. It would make things weird and awkward and I don't want that to happen."
"Things don't have to get weird and awkward between us if we don't let them. We could just make a pact that it's a one time thing and that neither of us will catch feelings for the other because we don't like each other like that. You would just be my best friend helping me out and doing me a favor."
"Nope. No way," he said shaking his head. "You don't know what you're asking for Berk. It would be impossible for it not to change things between us."
"Please Dean. I'm ready for that step in my life. I want to know what sex feels like and I can't imagine trusting any other guy enough to have my first time with them," she begged.
Dean stood up off the bed and said, "No. It's not happening and I'm not changing my mind," he said firmly. "So let's just pretend this conversation never happened. I'm hungry. Let's go eat."
She took a deep breath in and let it out, before finally standing up and saying, "Fine. Whatever," in a mopey voice.
"Don't pout," he laughed. "You'll thank me later for saying no. I promise."
"Well since you did say no you can't be mad at me when I find a random hot stranger to bang who may or may not be a good guy."
He laughed and shook his head, wrapping an arm around her shoulder as he lead her out the door.
"You're cute when you're pouty," he said, with a smile, kissing the side of her head.
She glared up at him and then she couldn't help but smile and laugh.
"You're probably right," she told him as they walked down the long hallway towards the elevator. "When Ember first suggested it I told her she was crazy but after what happened this morning, I thought maybe practicing with you was a good idea. Momentary lapse of judgement I guess," she laughed. "It looks like I'll just be hooking up with a random stranger instead."
"A random stranger? You don't want it to be just anybody Berk. I mean it's your first time."
"Hey, you had your chance to make sure I did it with a good guy and you blew it. The next hot guy I see is gonna be mine," she teased, laughing. She loved giving him a hard time and seeing his reaction. She felt his arm tense around her shoulder and she could tell he wasn't happy about that idea.
They slid into the booth at the diner across from each other and started looking over the menu and she looked at this man sitting across from her that she had seen every day for the last almost 19 years and really looked at him.
Dean was tall and muscular and had dark brown hair that always laid perfectly no matter how hard you tried to mess it up, strong thick eyebrows, clear tanned skin and piercing dark blue eyes. His square jawline was peppered very lightly with stubble but it was clean and well groomed, giving him a rugged manly look. He was gorgeous and always had been since they were really little and he had this confident swagger that only he could pull off without seeming like a douchebag.
His confidence came from excelling at every sport he ever tried and knowing he could get any woman he wanted and he pretty much had. She couldn't remember him ever wanting a girl he didn't eventually get. He was genius level smart and everything he tried to do he instantly was amazing at it, which was frustrating because he always beat her at everything, everything except video games. He also had a big heart and that's why he had always been her best friend. He gave up going to Yale, his dream school, because she didn't get accepted and he didn't want to go to college without her after everything she had been through.
He didn't really give it up. He just paid the fee to defer acceptance for a year so he could spend his Freshman year at Boston University with Berkley. She had tried to talk him out of it but he insisted. He said he didn't feel comfortable being that far away until he knew she was better and didn't need him.
She heard a deep voice say, "Berkley? Is that really you?" pulling her out of her thoughts about Dean.
She looked up to see where it was coming from and she saw a tall figure heading towards their table and her heart skipped a beat.
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