Brie’s Babysitting Service: Sadie by Jay2Kay

“Why not? You seem like a nice, smart guy,” she reasoned with him.

“I don’t know,” he said.

“Okay,” she replied, not pushing the issue. “You’re talking to me, though,” she pointed out.

“And this is probably the longest conversation I think I’ve ever had with someone of the opposite sex,” he told her, but something told her that wasn’t totally true.

“Really?” she asked. “Well, I’m flattered,” she added with a wink, his face turning a brighter shade of pink.

They sat and watched a supposedly non-scripted dating show that felt very scripted until Sadie got bored and wanted to continue the conversation.

“So, what kind of things are you into?” she asked.

“What do you mean?”

“Like, do you have any hobbies? Play any sports? Stuff like that,” she asked, turning away from the TV to face him on the couch instead.

“Oh, no, I don’t play any sports. All those guys are assholes,” he said. “I mostly just do my homework and play videogames with friends sometimes.”

“That’s cool, though,” she said. “I’ve never been very good at videogames, but I loved sitting and watching my boyfriends play. The crazy hand-eye coordination they had was cool to watch,” she said and he gawked at her, his mouth half open. “What?” she giggled.

“You’re lying,” he said and her mouth dropped open, appalled at what he said. “I’m sorry, I just have never met a girl who was into gaming like me and my friends,” he said defensively.

She smiled back at him again. “I was teasing you, but that’s fair. Gamer girls are becoming a thing, though,” she pointed out.

“True,” he agreed. “Just not in my school. Not that I know of anyway,” he said.

“So, why haven’t you ever asked a girl out?” she asked him.

“I don’t exist to any of them,” he stated simply.

“Have you put yourself out there?” she asked.

“No,” he grumbled.

“Maybe you should,” she suggested. “I mean, you’re a cute guy; you are definitely built for sports, even if you don’t like them; you’re smart so you know how to hold a conversation, I mean, look at us right now; and from what I can tell, you respect girls,” she said. “Probably so much that they intimidate you, don’t they?” she asked, realizing the root of the problem.

He stared her in the eye for a moment before finally nodding. “I’m terrified to talk to one. The only time I’ve had a conversation with a girl was when I was forced to for a school project or something,” he confessed to her. “Well, except for one,” he said. “But I haven’t talked to her in over a year,” he explained.

“Why not?”

“It’s a long story,” he said and she could tell he didn’t want to talk about it.

They sat there in silence for a few minutes while Sadie thought about what she could do to help him. This wasn’t a problem that could be fixed by simply hooking up with him to boost his confidence; she had to do something that would stick, but what?

“Where do the kids from your school like to hang out?” she asked.

Sean shrugged. “I have no idea, they’ve never invited me,” he told her.

She thought about it for a moment. “Do this; pay attention to their conversations and see if they talk about any parties, or a hangout where they all get together, probably to drink illegally-”

“Oh, that’s easy, the lake,” he said. “I thought you meant like a house party or something,” he said.

“Nope, anywhere they gather outside of school. Hold on, is there a football game coming up?” she asked.

“Well, they play every Friday, but this week they’re traveling for the game,” he said.

“Where to?” she asked.

“I think just to the other side of the lake, Lakeside High School,” he said.

“I know you hate sports, but I think you should take me to that game,” she said.

He stared at her again, unsure of how to respond. On the one hand, she was forcing him to go to a football game, something he’s probably refused to do since Freshman year; on the other hand, he would be out late with an extremely hot girl almost two years older than him.

“Can I think about it?” he asked.

“Of course, I’m not going to force you to do anything you don’t want to do. I just want to help you,” she said.

“Why?” he asked.

“What?”

“Why do you want to help me?”

“Why not?” she asked, knowing if she said it was what she was hired to do that it would ruin any chance she had of success. “We’ve just spent the past half an hour talking and getting to know each other, I just want to help you and I think I know how,” she explained.

“Did my mother put you up to this? Did she hire you to get me a girlfriend?” he questioned.

Fuck, he’s smart, she thought to herself.

“What can I do to prove that this is all my idea, regardless if it’s what your mom wanted or not? Because, she hired me to take care of your sisters so she could go back to work, that’s what’s in my contract; nothing in it mentions you at all,” she told him.

“But she did tell you about me and how she’s worried that I’ve never been on a date, not even a school dance, or that I’m gay or something,” he stated.

“She did, and honestly if you were gay, she wouldn’t care, but I can tell you’re definitely not,” she said.

“Is that right?” he asked.

“One hundred percent,” she replied, feeling slightly heated, but keeping herself under complete control because she knew she was getting him right where she wanted him. “I can almost guarantee that when you first saw me when you got home from school, you went into that bathroom to jerk off because you couldn’t hide the boner you had,” she said and his face went beet red; his mouth opened and closed as if attempting to speak but his words were completely caught in his throat. “I actually liked that,” she said changing her tone and his eyebrows came together in a look of confusion. “It turned me on to know that just the sight of me turned you on,” she said slowly crawling towards him on the couch, her tits seemed to grow in her position on all fours.

“It-it-it-it did?” he stuttered, nervous sweat beading up on his forehead as she grew closer; the fear in his eyes made Sadie think he would bolt at any second, but he was somehow frozen to that spot on the couch.

“It did,” she whispered in his ear now that she was only inches away from him. “Sean?” she said.

“Yeah?” he whispered back hoarsely.

“Have you ever kissed a girl?” she asked him and he shook his head nervously. “Can I be your first kiss?” she asked and he froze, scared but desperate to kiss her at the same time.

Sadie reached up and dragged her nails over his cheek as she slowly brought her face closer to his. He licked his lips involuntarily and she grinned at him, taking that as her answer. Gradually she moved her lips closer to his, his hot, ragged breath blasting her in the face as hers gently warmed his skin. He closed his eyes, so she did as well as she gently pressed her lips against his. His breathing suddenly calmed as she pressed firmly into him with her soft lips. She parted hers slightly and he responded to her movement, opening his mouth equally. She licked his lips and then instinct kicked in for him and his tongue met hers. She began to open and close her mouth in a slow rhythm as she pressed her tongue against his and he responded in like, learning from her what to do.

Without breaking their kiss, she whipped her leg over his lap and straddled him, his already hard cock pressed into her denim shorts. From what she could tell, he was packing a decent size tool in there. She slowly grinded into him as they made out there on the couch until she felt an unexpected warmth come over her ass and pussy. Breaking the kiss, she looked down to see his embarrassed eyes.

“It’s okay,” she whispered assuredly, but he pushed her off of him and ran to his room. Thirty seconds later she heard him enter the bathroom and the shower turn on. She checked the time on the clock and it was just barely four o’clock; Mary still had another hour until she was off and then it would take her about fifteen minutes to get home. She had time to fix this.

She grabbed the baby monitor and brought it with her to the bathroom, just in case. She didn’t want the girls to start crying and she not notice; that would get her fired regardless if she was fulfilling a different part of her duties that were requested by their mother. She opened the bathroom door to find him start naked, about to get in the shower; he’d already wiped up his cum with the wadded-up boxer briefs she spotted at his feet. He was still hard and was about to take matters into his own hands in the shower when she opened the door. His eyes were wide with shock and his mouth hung open, completely wordless.

“Let me help you with that,” she said knowing that this was every teenage boy’s wet dream to have a slightly older woman offer to take care of their boner (yes, boner, that’s what every teenage boy calls it, amongst other things). “And you have nothing to be embarrassed about,” she said, closing the door and dropping to her knees as she reached for his thick, seven-inch cock. “I gave you a little more than you were expecting for your first kiss. May I?” she asked before fully grasping his meat.

Sean answered by turning towards her and she smiled up at him as she gripped his shaft and slowly jerked him.

“I should have made your first kiss a little more innocent and a little less…porn fantasy,” she said and he couldn’t help but grin this time. “There it is, that sweet smile of yours,” she said and then leaned her face towards the thick missile in her hand.

She looked up at him with pleading eyes and he nodded slowly. “Thank you,” she whispered to him and then took the tip of his cock in her mouth. He’d just came a couple minutes ago, so she knew he wasn’t ready to blow just yet, though she didn’t expect it to take long for a second orgasm for him.

Sadie swirled her tongue around the tip of his cock for a moment before slowly taking the rest of him into her mouth. She kept her eyes on his, loving every expression from his face as she serviced his cock; the shock, the excitement, the fear. Every emotion morphing into the next; it absolutely drove her wild to know she was causing all of that. She began to bob her head up and down his cock and then she reached up, grabbed his wrist and brought his hand to her head; she knew he’d know what to do once it was there.