Hey everyone so here's the sequel to Hopeless! Instead of making it another story I'm just making each chapter a separate one-shot highlighting important moments. It'll go in chronological order and each chapter will be a story flashing a point in their life. Some of them will be smutty and some of them will just be fluffy. I'm going to also take requests so if there's anything you guys are interested in seeing let me know I'd love to include it! This chapter starts a few weeks from where Hopeless left off and Damon and Elena are going to the Salvatore's beach house with Katherine and Stefan. Please leave reviews and enjoy!

Chapter 1

EPOV

"Katherine if you don't come down in the next ten seconds we're leaving without you," Damon shouted from the bottom of the stairs.

"Stop being so impatient Damon," she shouted from her bedroom," I'll be down in a minute."

"Damon you know 9 am our time means 9:45 in Katherine time," I said laughing.

"Well I was hoping we could get there early enough to hit the beach," he said wrapping his arms around me from behind and pressing kisses along the back of my neck.

"We'll get there in time," I said as a shiver ran down my spine.

"I can't wait to have an entire week with you," he said turning me around to face him. Ever since my dad found out about us we haven't had any alone time together and it took an insane amount of begging to convince him to let us go to the beach house. He's also under the impression that Damon's grandparents will be there which is completely untrue.

"This week is going to be amazing," I said pressing a quick kiss to his lips.

"Okay she's finally ready," Stefan said walking down the stairs with all of Katherine's suitcases.

"We're only going for a week Kat you look like you're moving in," Damon said smirking.

"I just want to be prepared," she said as we all walked out the front door. Stefan's driving because his Tahoe will fit all of our stuff, especially since Katherine packed her entire bedroom.

"Okay you need to call me when you get there," my mom said following us out to the car," and behave yourselves. No calling me from a jail cell."

"I think we'll manage," I said laughing and hugging her goodbye. We all piled in the car and started driving away a little after 10.

"Katherine why is that dog stuffed animal flat," Damon asked smirking as we drove.

"It's a pillow pet Damon," she said giving him the evil eye from the front seat," Stefan gave it to me."

"Stefan you got her a pillow pet," he asked snickering and I couldn't help but crack a smile myself.

"She practically begged me for it," Stefan said defending himself.

"Sue me, I saw the commercial and thought they were cute," Katherine said shrugging.

"This is why I'm with Elena she doesn't ask for creepy flat stuffed animals," Damon said kissing the top of my head. I rested my head against his shoulder and scooted in closer to him relishing in this time for us to be together.

"Okay can we change the music please," Damon said an hour later," I will seriously die if I hear another Nicki Minaj song."

"I'm in charge of the iPod therefore I pick the music," Katherine said defiantly.

"Come on Kat we're dying back here," I said groaning. Unfortunately she was not budging so I opted for taking a nap and I fell asleep for the rest of the ride.

"Lena wake up we're here," Damon said shaking me out of my slumber. I slowly opened my eyes and looked up at him with a smile on my face. We got out of the car and Damon grabbed our bags.

"This place is insane," I said looking up at the magnificent house.

"Yeah it's pretty cool," Damon said shrugging. I followed him through the front door and up the winding staircase towards a bedroom. It had a big window with an amazing view of the ocean, but before I knew it Damon had pushed me down on the bed.

"Just imagine a whole week of this," he said kissing me and moving his hands under my shirt to roam my back. I kissed him back granting him entrance to my mouth so his tongue could run along mine.

"Hey we're hitting the beach," Katherine said running into the room before covering her eyes," sorry I didn't mean to interrupt."

"Uh it's fine we'll meet you there," Damon said getting off the bed and pulling me up with him. We changed into our swimsuits and walked down to the beach.

"This place is really beautiful," I said looking out at the ocean.

"You're really beautiful," Damon said picking me up and I let out a surprised shriek and he started running towards the ocean. He ran us into the water when a huge wave came crashing over us and I fell from his arms.

"Oh my god it's freezing," I shouted running back to shore.

"Then let me warm you up," he said wiggling his eyebrows and wrapping his arms around me pressing his lips against mine. I wrapped my arms around him and his hands moved down to cup my ass. He swept me off my feet again without breaking the kiss and I instinctively wrapped my legs around him.

"Can you two keep your hands to yourselves for like 5 minutes," Katherine said interrupting us and Damon hesitantly put me down," come on Stefan's going to take us out on the boat."

Damon intertwined his fingers with mine and we followed Katherine to the Salvatore's dock where a large boat was located.

"Oh my god is this your families boat," I asked in awe," this thing is ridiculous."

"Yeah seriously Damon are you related to Bill Gates or something," Katherine asked laughing as we got on the boat.

"You guys haven't even seen my grandparents house in the Hampton's or the penthouse in New York," he said smirking," it's like an episode of Gossip Girl."

"Damon you watch Gossip Girl," Stefan asked laughing.

"Elena and I used to make him watch it with us," Katherine said smirking," but he liked it way more than he's willing to admit."

"Oh please I just watched it because you did," he said rolling his eyes.

"Salvatore you shed a few tears when it ended don't lie," Katherine said teasing him.

"Whatever I'm still Damon the hot bad ass," he said motioning to his body.

"I'm surprised we can all fit on the boat with your ego," Katherine said rolling her eyes.

"Come on cocky let's go sit down," I said pulling him towards the back of the boat.

"You know we've never done it on a boat before," he whispered in my ear pulling me onto his lap.

"Yeah I'm sure Katherine and Stefan wouldn't be scarred for life," I said smirking.

"Well you're the one torturing me with this bikini," he said pressing open-mouthed kisses down my neck.

"Damon I am not sleeping with you on a boat with my sister like 30 feet away," I said trying not to be distracted by his mouth.

"You feel this," he said bringing my hand to his erection that I could feel through his swim trunks.

"Well you'll just have to wait until we get back to shore," I said wiggling out of his embrace and walking away.

"Elena Gilbert you're evil," he said groaning and I winked at him as I walked towards Katherine and Stefan. We drove around for a while and Stefan stopped the boat in the middle so we could all eat dinner before we pulled up and got back onto solid ground.

"So you guys wanna watch a movie or something," Katherine asked as we walked back into the house.

"No we have other plans," Damon said wiggling his eyebrows and wrapping his arm around my shoulder.

"Oh okay," Katherine said awkwardly and we stayed silent until we made it back to the house.

"Finally we're alone," Damon said closing the door to our room and pushing me onto the bed before I could say anything.

"Well actually…," I said getting off the bed," I need to get cleaned up so it'll have to wait."

I untied my bathing suit top then dropped my bottoms and tossed him a wink before walking into the bathroom and turning on the shower.

"Now you're just being cruel," he said walking into the bathroom and I noticed he'd dropped his suit too.

"Then come join me," I said defiantly while motioned for him to come over. He smiled and opened the shower door pulling me flush against him right away.

"You've been teasing me all day," he said running his hands down the side of my naked body," and it has been far too long since I've had you."

"Then take me," I said running my fingers through his hair and kissing him passionately.

"God I love you so much," he said lifting me up and I wrapped my legs around him.

"I love you ohhh," I said interrupted when I thrust inside me. He backed us up pinning me between the wall and his body and pressing his lips against mine. I moaned into the kiss as he pounded into me relentlessly. We haven't been together since the night of graduation and I could already feel myself getting close.

"You're so fucking perfect," he whispered in my ear before bring his mouth down my neck and kissing between my breasts. He pulled all the way out before plunging back inside and hitting that miracle spot over and over again and my moans got even louder.

"Oh god Damon," I cried and silenced me with another kiss, his tongue exploring my mouth and I brought my hands up to cup his face. He started moving quicker and I had to bite his shoulder to stop myself from screaming at the top of my lungs.

"Elena come for me," he said hoarsely and I turned into a melting pool in his arms as my entire body started trembling while my orgasm hit me like a ton of bricks.

"Ahh god," I moaned as I pulsed around him my breathing heavy. He came a few seconds later emptying deep inside of me. After we came down from our highs he slowly put me down and I had to hold onto him so I wouldn't collapse.

"That was amazing," I said dazed as I looked up at him with a grin on my face.

"Yeah it was," he said running his hand up and down my back with a strange expression on his face.

"What's that look," I asked skeptically.

"I'm happy," he said rolling his eyes and grinning before bringing my lips to his again. He turned off the water and helped me dry off before carrying me into the bedroom and starting round two. An entire week of this, life couldn't get any better.