Damon Salvatore was a regular sixteen year old guy well at least that was what he wanted everyone to believe; in fact he was like every other guy in his class at school except he was working two jobs trying desperately to keep a roof over his head. Damon's mother was an alcoholic and she was growing less capable of looking after him and his little brother Stefan by the week. She managed to go to her cleaning job at the Gilbert resident but that was about it. That was exactly where Damon was now, The Gilbert residence. He wasn't here to clean like his mother he was here as a sitter. Michael Gilbert was a surgeon at the local hospital and his wife Elena worked as a fashion designer. They had two children, boys, aged 7 and 3. Although being married for seven years and having successful careers each you'd expect them to be older but in fact they'd been married right out of high school. Tonight they were at some social event and Damon's mother had forced him into taking the job of sitter, he didn't really mind because the Gilbert's had left him plenty of food and they kids were well behaved and besides the house they lived in was so fancy. They had like 500 more tv channels for him to watch, he just prayed no one at school found out. Both of the boys were asleep in their rooms and Damon headed out into the yard for a quick smoke. He'd barely stomped out the cigarette when he heard a car pull up outside. Racing inside he sat down on the couch seconds before the Gilbert's came in. He could hear them arguing in the hall.

"It's not my fault."

"One night!" Elena fumed "I just wanted one night away from being a Mom, I didn't get my hair done and buy a new dress for us to be out for one hour and then home again!"

"I have to answer my pager!" Michael roared. "It's my god damn job!"

"Fuck your job." Elena spat and Damon heard her running upstairs.

He sat awkwardly on the edge of his seat and waited for Michael to come in.

"I'm sorry you heard that." He said

Damon stood up "Don't worry about it."

"Work." Michael said waving his pager "I need to dash to the hospital. I know we were only gone for an hour but I'll pay you in full."

"You don't have to." Damon said awkwardly, but he really needed the money

"Here." Michael said handing over the cash "I've got to run."

Just then the littlest Gilbert came padding into the room, rubbing his eyes.

"Crap, we woke Harry." Michael said "I really need to run. Can you put him down before you go?"

"Sure." Damon said taking little Harry's hand "Come on buddy."

"Thanks." Michael "Ask the witch to drive you home, it looks like it's going to be stormy."

"What about the kids, they're asleep?"

"She can leave them for ten minutes. It'll be fine."

"Okay." Damon said sceptically as he walked Harry up stairs.

He tucked Harry back into his bed and pulled the spider man toy up for him to cuddle.

"Night bud, see ya another time." Damon ruffled his hair before returning down stairs. If Harry was anything like Stefan was at that age he would be up again in five minutes. He clicked on the fancy baby monitor on the coffee table and began tidying up the mess he'd made, throwing his soda cans in the bin and chip bags. It was raining heavily outside and it was a long walk back home. He went back to the couch and waited for Elena to come back down stairs so he could ask for that ride home.

He watched tv for a little while as he waited. His ears perked up suddenly but a peculiar sound, he grabbed the tv remote and muted the volume.

"Uhhh."

He sat up straighter and looked to where the sound had come from. It was the baby monitor. He got up and switched on the camera part to see if Harry was alright but instead he saw a bedside lamp and a perfume bottle. It suddenly dawned on him that the Gilbert's must have left the second part accidently in their room. He couldn't see anything and figured Elena was getting changed so he switched the camera setting off. He sat back down on the couch and then heard it again.

"Ugh."

Damon's ears perked up again but that wasn't the only thing.

"Ugggh."

Damn it. His cock sprung to life, as he heard yet another breathy moan. There was no mistaking those sounds.

He knew he should get up and leave but he just couldn't seem to do it. He was after all a hormone raged teenager.

"Mmmm"

God she was killing him. His pants were so tight.

Fuck it. All caution thrown to the wind Damon pulled his painfully hard dick out of his pants. He began jerking off as he listened to Elena's heavy breathing and panting.

It was so juvenile but she sounded so sexy he couldn't help himself.

"Oh." She purred through the monitor and he sped his hand.

"Ugh…ugh… ooh…"

Damon jack himself harder. He was painfully close, the danger was such a turn on.

He noticed the incline in her voice. "Uh-uh-UH-UGHH-"

He closed his eyes and imagined what she was doing

"UGH-UGH-OH GOD!"

Damon's cock erupted over his speeding hand.

He continued to shoot until he heard her come down from her orgasm.

Just then his sense caught up with him and he sprang to his feet and grabbed a handful of tissues and began cleaning himself up. He heard movement on the monitor and he fixed himself up properly, throwing the tissues into the waste paper basket.

Elena came into the room, she looked startled.

"Damon! I thought you were gone?" she said throwing her hand to her chest in alarm.

"I…no…" he said awkwardly. She was wearing a wine coloured silk robe. He couldn't take his eyes off her.

"I thought my husband was driving you home on his way to work?"

Damon shuffled on the spot. "No. He had to rush. I better get going actually…"

"It's pouring down." Elena said looking torn. "I could drop you home?"

"No." Damon said "Thanks, but the kids are asleep. You can't leave them…"

"They'll be fine for a few minutes. I know that's not very responsible but they're both asleep… I can ask the neighbour to pop in. Really, it's so stormy…"

"No, really…" Damon protested. God, she looked so sexy. He couldn't stop thinking about before. He needed to leave.

"At least let me get you a taxi?..." she said before she fell silent.

Damon flushed red praying she hadn't noticed.

"How old are you, Damon?" she swallowed, looking flushed

"Sixteen, Mrs. Gilbert." He answered, letting his hands drop down, trying to cover his erection. He knew she'd seen it.

"Damon…" she said looking affronted

"I'll go." He said quickly

"No- wait." She said "Look this might be the champagne from earlier talking but…"

Damon stopped. "But?" he added, encouraging her to go on

"My husband and I, we don't get along anymore…"

"Oh." Was all Damon managed to say. He didn't dare dream what she was getting at.

"You're really handsome, you know. Do you have a girlfriend?" she asked

"Yes." Damon replied, Caroline Forbes. She was hot but she wasn't ready for sex yet, all they did was make out.

"Oh." She said looking crestfallen. "Well… that's that."

Damon was flustered. Was she really asking him for something?

"Mrs. Gilbert, Elena… what exactly are you getting at?" he asked her with a thrill of forbidden excitement

"I need sex." She said bluntly "I need it."

Damon stood on the spot, unable to speak yet

"I feel like my whole life if out of control, I'm not even twenty six years old and I'm a wife and a mother of two children and my dream job is so much more work than I ever imagined and the pressure is-…" she looked close to tears.

Damon walked to her quickly. He grabbed her face in his hands and kissed her with everything he had. When he let her go she was trembling.

"Please?" she asked as she unbuckled his belt

He threw his head back when her hand slipped into his pants.

He was suddenly filled with a fierce passion. He knew how wring this was, and that she was married, his mother's boss, that she looked vulnerable but he wanted her so badly.

He was a virgin, but he knew what felt right. They fell backwards into the wall. Her silk robe fell open and for the first time in his life he saw a naked woman. He took one of her breasts into his mouth and she moaned in pleasure. She had her arms around his neck, and suddenly she threw her leg around his waist.

She called out in pleasure and Damon had lost his virginity as Elena joined them together. Damon pressed one of his hands onto the wall to steady them and he attentively began thrusting. This was completely new to him but by the sounds coming from Elena he was doing alright. He gripped her waist and groaned.

"Harder." Elena called out and Damon eager to please picked her up and walked across the room and lay them down on the fluffy rug, his jeans still around his ankles. He pulled out of her and kicked his pants off. She looked incredible lying there waiting for him. Her eyes were heavy with lust and he was so ready for her.

"You have such a big cock." She said with a laugh as he moved back over her.

Damon flushed with her compliment; he was so hard he was afraid it might be over sooner rather than later. Wasting no time he pushed back into her and set back to work, following her commands on thrusting and velocity.

She was calling out loudly and Damon was afraid she'd wake her children, but he also couldn't stop.

"Keep it there!" she cried and he happily obliged, he felt her walls tightening, his arms began to shake

"Not yet!" she shouted "Almost…"

"I'm gonna cum!" Damon groaned

"I'm almost… there… I…I'm cumming!"

Damon came hard inside her, harder than he'd ever cum before.

Elena was shaking uncontrollably; she pulled him down for a passionate kiss.

"That was amazing." She sighed. "You better get dressed."

Damon pulled out of her and quickly got dressed.

"You better leave." She said and she kissed him swiftly before she ascended the stairs.

Damon walked outside, dazed and confused. He walked down the road it the pouring rain. He'd done it, he wasn't a virgin anymore. His conscience patted him on the pack for a moment before the harsh reality of what had just happened fully hit him. He'd just fucked a married woman. He had spilled inside her, they hadn't used protection, and he'd left his money behind. Fuck.

A/N This is quite dark, what did you think of the beginning? Let me know if I should go on? Dr. B xx

Ps. I have no time to check for mistakes, sorry! Hope it's not too bad :S if it is I'll republish. But I really need to get to bed! haha