I can tell you a pro, but baby be gentle
'Cause
I ain't never did this before, no
and I ain't never did this before, no.
Vampires, witches, werewolves, hybrids, things had gotten so complicated and in such a short time. Their lives had always been connected peripherally, but now being among one of the few who knew about the supernatural they interacted regularly and got to know each other more than they ever did in 11 years of childhood in just this last year.
Klaus, the original hybrid who was a threat to everything they knew and loved, was finally dead and they all celebrated with a party that had end a half an hour ago and now it was just the who gang gathered up in the Salvatores living room post party basking in the glow of finally feeling safe, or as safe as on could feel with Damon still around, but still for now there were no threats just a bunch of teenagers drunk after a house party.
"Tyler, truth or dare?" Caroline said walking in with a open new bottle of champagne taking a swig from it.
"What are we? In high school?"
"Yes! Finally we're just high school students for the first time in what feels like forever. Just answer the question Tyler."
"Fine, truth."
"Lame."
"I'm playing the game, you don't get to criticize my choice."
"Fine, let me think of a good question." Caroline looked around at everyone the room and tried to think about what question would yield the best results. When she eyed Bonnie she knew exactly what to ask. "Who was your first?"
Tyler sighed. Damon rolled his eyes at the juvenile question, Stefan looked disinterested, Bonnie rolled her eyes knowing where this was going and Jeremy just looked bored.
Elena snoredt. "Are you sure he even remembers?"
"He should. You never forget your first. Isn't that right Damon?"
"You got me there blondie."
"See, so Tyler should remember his first, if the man-whore over there can."
"Why are you asking a question you already know the answer to Caroline?"
"Because I don't, I know who you've slept with but I don't know who was the first."
Tyler rolled his eyes and conceded. "Bonnie."
"What?" The three girls said simultaneously.
"I told you, you knew the answer."
"I knew you were Bonnie's first but I didn't know she was yours."
"It was eight grade who else would I have slept with?"
"I don't know, Vicki?"
"Hey," Matt chimed in.
"Don't act surprised."
"She was still my sister."
"I know I'm sorry."
"Wait a minute, you slept with Tyler," Jeremy said outraged.
"You slept with Vicki," Bonnie pointed out.
"Yeah, but I didn't lie about it."
"And I didn't lie about this."
"But you never told me."
"When would I have told you?"
"Alright, calm down both of you. If you must argue please take it outside where I don't have to listen to this high school shit," Damon rudely interrupted.
Tyler looked at Caroline. "You happy now," he said pointedly to her enjoying himself way too much. Caroline scoffed.
That was the end of their post celebration. Truth or dare had effectively killed the mood and everyone either went to bed or home. It was late and Bonnie was in the kitchen sitting at the counter enjoy the ice cream straight out of the tub.
Tyler walked in. "Hey."
"Hi," she said tentatively.
"Hungry too?" he said with a smile.
"What gave it away?"
He didn't answer her. He raided the cupboards and fridge to find them both sparsely populated. He settled on a bowl of cereal and plopped down next to her.
"So…crazy night."
"Yeah." Silence fell between them—the only noise heard was their eating sounds.
"So why did you act like you didn't know you were my first?"
Bonnie paused mid scoop, "I wasn't acting."
"You had to have known I was just as awkward as you."
"I wasn't awkward!"
Tyler laughed loudly and Bonnie soon joined. It was a bold face lie and they both knew it.
"Tyler, do even remember what you were like back then?"
"Vaguely."
"You were arrogant."
"Don't spare my feelings or anything?"
"It's true. You were arrogant and you liked to talk. There were enough rumors going around that I seriously considered someone else because I thought you had herpes or something. And then after you were just as arrogant, so what was I supposed to think?"
Silence fell on them again and they focused on their food. Bonnie decided she was full and put the ice cream back. She was about to leave to the guest room with Jeremy when his words stopped her.
"You know I have to make it up to you right?"
"What?"
"I have to make it up to you."
"Why do you have to make it up to me."
"Because I was horrible and I can't have you thinking I'm bad at sex."
They both laughed.
"I'm sure you've improved since then."
"But you won't know until I show you. It won't be tonight, or the night after that but eventually I will show you I can be better."
"Good night Tyler."
Three Years Ago
Looking back on it, Bonnie can say losing her virginity at 14 wasn't the best idea. She didn't particularly regret it, but she definitely wasn't proud of it. Don't get her wrong, sex can be a beautiful thing, a fun thing, a pleasurable thing, but it definitely wasn't any of those things when she was 14 and all she could think about was beating Caroline and Elena at something.
Caroline was the first to have a boyfriend, followed by Elena, and then her. Elena was the first to get boobs, followed by Caroline, and then her. Caroline was the first to get her period, followed by Elena, and then her which she quickly realized was a blessing, but still, she was tired of feeling like the late bloomer, so she decided that she was going to be the first to have sex.
It took less effort than she expected it to, getting a boy to sleep with her. She knew she wasn't ugly by any means, but she wasn't a smooth talker, and lucky for her Tyler Lockwood didn't need her to be anything other than direct. All it took was for her to come up to him at one of his infamous parties and say "want to have sex" for him to disown all his friends and take her up to his room.
It didn't take him long to attack her mouth and roughly grab her boob quickly rushing them over to his king sized bed. Tyler was excited to have sex with any girl let alone Bonnie. She was the prettiest girl in their year, but also the most reserved, so he had no idea when an opportunity like this would arise again.
He disengaged himself when they reached the end of the bed.
"Should we take off our clothes?" he asked nervously hoping she didn't back out.
"Um…yeah, sure. And put this on." She handed him a condom from her pocket. She came prepared.
When they were both completely naked they moved underneath the sheets of his bed with him on top. He looked down at her with an overly excited grin. He had a naked girl underneath him, that had never happened before.
"Can I…can I go in now?"
"Yeah," she said plainly.
"Alright, brace yourself."
I am. She thought to herself. From what she heard from others she knew that it was going to hurt, and it did. There was a lot of resistance from her nether region, but that didn't stop Tyler, he just kept pushing and pushing until he was a far as he could go. Bonnie tried deep breaths but it was too much pain that she had to stop him.
"You want me to get out?" he asked with his voice quaking.
Bonnie shook her head. The thought of him moving even just to get out seemed like it would be just too painful so she had him stay still with his dick inside her.
Though he felt bad that she wasn't enjoying it as much as he was that didn't stop the amazing feeling. He tried not to move but his hips went on autopilot moving in and out of her slowly. Bonnie's face scrunched in pain. He wanted to hold out, tried to hold out until it could get good for her, but the sensation was too good that his hips involuntarily jerked as he released his load in the condom.
"Shit, shit, shit," he hissed. When his sense came back to him embarrassment filled him as he slowly pulled out and rolled over onto his back. "Sorry."
"It's alright." And she meant it. Though she expected more she was kind of glad he finished, she didn't know how much longer she could take the pain. Plus she wasn't expecting it to be perfect, just something to get out of the way and now it was gone. She sat up and motioned to leave.
"You don't have to go. We could try again this time better."
She gave him a sympathetic smile. "It's alright Ty, besides you have a party get back to." And with that she got dressed and left him to his embarrassment.
When she told Caroline and Elena they were speechless. Sex, while was something they both had thought about, was uncharted territory for them that they both feared. Very few people in their grade had actually had sex and most of it was rumors. So when Bonnie told them both in a very flippant tone that she had sex they were completely dumbfounded.
First, it was Bonnie, they didn't know how to explain it but she just didn't do things like that. She was very reserved and careful how she planned things out. Second, she didn't have a boyfriend, not that they knew of, so they had no idea who she was supposed to have had sex with. And lastly, they were curious about what it was like, especially Elena. Her and Matt had been dating since sixth grade and she felt that they were ready for the next step, but she was too scared to go through with it.
They flooded her with questions which she gladly answered. First question being who.
"TYLER!" they said in unison. He was the oldest boy in their class and though it wasn't true in the slightest to them that made him the most mature. Bonnie didn't just pick Tyler randomly, he raised her popularity and was one of the biggest gossips in school so he had already told everyone in school by now. Caroline had heard it through the grapevine but didn't believe until Bonnie spoke the words herself.
They asked for details but because not much had actually happened she embellished a bit (a lot). Given all the lying she did with the details she wondered why she bothered to go through with it at all, but she guessed that it was for her own peace of mind. It was her goal to make herself feel better, not brag to everyone, and the moment she realized that the better she felt about lying. The real story was for her and only her, well, only her and Tyler. It was a moment they shared which they would remember for the rest of their lives.