Hello my lovelies :) Thank you for the reviews! I hope you like this next chapter :) I've spent most of today writing this instead of doing uni work haha. My other stories will probably be updated tomorrow for those of you who follow them as well. xx


Groaning into her pillow, Jessica kept her eyes shut tight and tried to wipe away her memories of the night before. She felt embarrassed. She felt like a fool and she hated herself for making it obvious how much she wanted Damon Salvatore. Yes, he was a jerk and yes, he had treated her sister badly but that was two years ago and although Caroline still disliked Damon, Jessica could see that he wasn't the same man he was when he came to Mystic Falls.

Telling him she was a virgin felt like the worst mistake she could have made. She wasn't a slut by any stretch of the imagine but she wasn't exactly innocent either. She had done her own share of fooling around; she just hadn't let it go any further than making out and a heavy petting session. If truth be told, she had been holding back because she had always wanted to know what it would be like to be with Damon.

Hearing her mom's voice call out for her to get out of bed, Jessica let out another groan. It was just before nine in the morning. Once Damon had taken her home and she had calmed down enough to sleep, the time had already passed four a.m. Dragging herself from her bed, Jessica padded down the hall way and through to the kitchen where she found her mom waiting for her.

Jessica had always felt sorry for her mom. Being the Sherriff of Mystic Falls was a tougher job than most took it for and her mom had not had an easy life. When their father left, Jessica and Caroline had cried for weeks but as they grew older things changed. Caroline, although she loved her mother, grew distant and blamed her for their father leaving. Jessica, on the other hand, favoured her mother and tried hard not to disappoint her.

"Morning, mom." Jessica yawned.
"Good morning, Jess." Liz replied, smiling at her youngest daughter. "I won't be home tonight so it will just be you and Caroline."
"That's fine, mom."
"Actually, I won't be here." Caroline stated as she entered the room; having heard the conversation between her mother and sister. "I'm staying over at Tyler's tonight."

Liz frowned. Her job often kept her away from her two daughters and she had spent many nights sleeping in her office over the years. Now that Caroline was a vampire and could easily take care of herself, Liz did not feel the need to worry about her oldest quite so much as she used to. However, where Jessica was concerned, Liz worried constantly. She knew Jessica, too, was independent and capable of caring for herself like her older sister, but Liz hated the thought of her being home alone all night. Anything could happen to her.

"Caroline, can't you-"
"Mom, it's fine. I'll be okay on my own. I'll just grab some dinner at The Grill with Jeremy."
"Hmmm… Fine, but make sure to lock all the doors and windows before you go the bed. Just to be safe."
"I will. I'd better get ready. I'm meeting Jeremy soon."

Bidding goodbye to her mom, Jessica made her way to the bathroom and showered quickly; feeling last night wash away with every second the water ran down her body. Although she understood why Damon had stopped, she cursed him for not living up to his reputation and choosing to be honourable with her.


"Hey, Jeremy." Jessica smiled, greeting her best friend.

Despite being a year older than her, Jessica had been friends with Jeremy Gilbert for as long as she could remember. It helped that their sisters were also best friends. Barely a day went by where Jessica did not see Jeremy. For years, their sisters teased them and as they reached their teenage years, many suspected that there was more to the friendship than the two teens were letting on. Both denied having any romantic feelings for the other. To Jessica, Jeremy was the brother she never had. He was her closest friend and she enjoyed spending time with him. The rumours and teasing stopped once Jeremy began dating Bonnie Bennett, a friend of Elena and Caroline, just over a year before.

"Hey, Jess." Jeremy grinned back.

It was a sunny, Saturday afternoon; having just passed noon, and the two friends were hanging out together in the house Jeremy shared with Elena and their Aunt Jenna.

"So, what do you want to do today?" Jess asked her friend.
"Movie?"
"Sounds good to me." Jessica smiled.

It was two hours later, as the movie Jessica and Jeremy were watching was nearing its end, that they heard Elena open the front door and come storming through the house followed by an angry looking Damon.

"I can't believe how selfish you are sometimes, Damon!"
"I'm selfish?! You might want to take a good look at yourself first before pointing the finger at me!"
"Stefan needs your help; I need your help and you're off doing god knows what all day and night!"
"Hey! I brought Stefan back. I am doing my best but you're not helping! He's a vampire, Elena! That means we drink human blood. Oh, and for the record, what I was doing last night is none of your bloody business!"
"Well I hope she was worth it!"
"What the hell makes you think I was sleeping with someone?"
"Because that's what you do, Damon. It's what you always do!"

Standing up, Jeremy walked away from the couch and addressed the screaming people.

"Hey, guys, what the hell is going on?"

Turning his head at the sound of Jeremy's voice, Damon looked in the direction of Elena's brother and saw Jessica now standing over by the couch. Meeting her eyes, Damon swore silently to himself. He knew saying no to Jessica last night had been the right thing to do, but he couldn't shake the feeling of regret that he did not take her for his. In his entire existence he had never taken a single girl's virginity and he found he couldn't stop thinking about how hot it would be to claim Jessica's.

Gulping, Damon forced himself to look away from Jessica and focus his attention on Jeremy.

"Nothing. Your sister doesn't seem to understand that Stefan is dangerous."
"If you would just let him out-"
"No, Elena! What if he kills someone, huh? Do you want that on your conscience?"
"He won't. Please, Damon." Elena pleaded.
"Do you know what? Do whatever you want, Elena. Let him out for all I care." Damon stated before stomping out of the Gilbert home.

Climbing into his car and driving back to his house, Damon seethed with fury. After everything he had done for her, Elena was still treating him as if he was the bad guy. Well, he thought, if he was going to live up to everybody's expectations of him as a dick, then he'd better do something worth being hated for.


Dancing around her bedroom with her music blasting at an extremely loud level, Jessica was glad that her sister had decided to spend the night at her boyfriend's house. It had been ages since Jessica had been able to let so loose in her own room without interruptions from her mom and sister to lower the volume of her music.

The fast beat of the music allowed her to forget about seeing Damon that afternoon. It had unnerved her to see him at the Gilbert house and acting as if nothing had taken place between them the night before. Thinking about it and the fact that he had rejected her, made Jessica feel even more annoyed and she shook the thoughts from her head and continued to dance crazily around the room.

It was when she had her eyes closed, spinning around, that her body came into contact with something hard and she let out a loud yelp. Feeling someone grab her wrists, Jessica snapped her eyes open and came face to face with Damon who was smirking at her.

"Damon!" Jessica shouted out; her heart racing.
"Nice dancing… nice panties." Damon said; letting his eyes fall on the pink, spotted panties Jessica was wearing along with a white vest top.

Jessica felt herself blush at Damon's words but then remembered she was still annoyed with him.

"Why the hell are you in my room? This is breaking and entering!"
"I did enter but I didn't break anything. So technically, it's just entering." Damon laughed out.
"I don't care. It's creepy. Now get the hell out of my room!" Jessica shouted; ripping her arms out of Damon's grip and staring at him angrily.
"And miss your fabulous dancing? I wouldn't dream of leaving."
"Caroline will be back soon."
"No, she won't. Don't lie to me." Damon said with a soft smile on his face; advancing upon Jessica who had taken a few steps away from him.
"Just, leave."
"No."
"Why the hell not?!"

Having backed her against her bedroom door, Damon stood in front of Jessica; effectively blocking her in. A teasing smile played on his lips and he watched as Jessica bit her own.

Looking up at Damon, Jessica couldn't stop herself from wanting to kiss him. The way his ocean-blue eyes were bearing into her made her feel like he was looking right into her soul, and it made her feel uncomfortable.

"Because you don't want me to leave." Damon stated clearly before crashing his lips into Jessica's, feeling her kiss him back instantly.

Feeling her legs leave the ground as Damon picked her up and told her to wrap them around his body, Jessica hoped he wouldn't reject her once again. She was nervous, yes, but she was also excited; very excited, she thought, judging from the dampness she could feel building up inside her panties.

Laying her down on the bed, Damon tried, and failed, not to smirk. It had taken him only a second to make his decision about taking the young girl virginity, and he could not think of a better, more enjoyable way to be bad. He knew he would have to be gentle with her but that was half the fun. Once he got her through her first time he would be able to show her how truly amazing sex was; especially when it was with him.

Quickly ridding himself of all of his clothes, Damon climbed on top of Jessica and pushed his body further into hers as he placed a variety of bites and kisses on the smooth skin of her neck.

Letting out a small moan at the sensations Damon was causing, Jessica tried to gain enough breathe so she could speak.

"D-Damon… Why… are you… doing THIS?!"

Jessica squealed. Right at the last moment, Damon had tore away her panties and placed two fingers inside of her; repeating his actions from the night before. Smiling at the way her body had reacted to his fingers, Damon moved his mouth up to her ear and nibbled gently on its lobe.

"You wanted me to fuck you and that's what I'm going to do."
"W-Why?" Jessica managed to breathe out. Her orgasm was getting closer by the second and Damon's fingers did not relent.
"Because I want to."

It took only a minute or two longer before Jessica came; her scream of Damon's name swallowed up as he kissed her forcefully. Damon did not allow Jessica to come down from her high before pushing himself into her by a few inches.

"This is going to hurt, Baby Forbes, but I promise, I'll make it feel better next time."

Jessica did not miss how Damon insinuated that there would be a next time. However, she did not get to ponder on it for long. The pain she felt as Damon pushed himself even further into her was almost unbearable. She had not expected it would hurt quite so much and she wasn't able to suppress a sharp intake of breath.

"I'm sorry." Damon whispered into her ear. "It will stop hurting soon." he said, continuing his slow, gentle thrusts into Jessica's body and revelling in the glorious tightness he felt.

As he promised, it did indeed eventually stop hurting and Jessica was overcome with pleasure. She suspected had she done it with anyone other than Damon that she would not be feeling any such pleasure. She was thankful she had waited and she was thankful for his many years of experience.

From the way she began to moan quietly, Damon could tell that the girl beneath him no longer felt any pain. The urge to increase his pace was tempting him greatly but he refrained from doing so. Jessica would be sore enough in the morning; he didn't need to make it worse.

"Damon." Jessica moaned out; bucking her hips to meet his slow thrusts.

Damon couldn't resist smiling. It pleased him to no end that he was making Jessica moan his name; that he was her first. Finally, someone had made him their first choice and it made him smile. Even if it was just sex, it still felt nice to be someone's first choice for a change.

Knowing his release was not far away, Damon let his hand fall between Jessica's legs and used fingers to tease her sensitive bud before kissing her again.

"Damon… I-I'm going t-to…" Jessica breathed out against Damon's lips; trying to warn him.

It was no use. Her orgasm hit her like a ton of bricks and her body shook violently. She could get out no sound as Damon was still kissing her passionately; something he continued do as he came inside of her seconds later.