“Congrats, sweetie! I’m so proud of you and you look amazing.” As usual, Lee’s words left her feeling incredible. Graduation ceremonies were typically a family event but Lee, his wife and kids were basically family to her and she could not have been happier to have them there.
They had been friends of the family since she was a little kid and she adored them all. If she had to pick a least favorite, it would probably have been Lee’s wife. She still loved her like family; it was just that she was kind of uptight and a little high class compared to Lee who was a man’s man. He was a sports junkie, worked on cars in his spare time and loved being outdoors, hunting, fishing, and so on. All of the things Anna loved too, making them pretty good buds.
Well, kind of buds. Anna had a sort of secret crush on Lee. He was undeniably good looking but it went so far beyond that. He was one of the few people that she felt she truly got along with. She could sit and talk with him for hours and it would feel like minutes. He was a shoulder to cry on when she needed it and was one of the few people who would tell her exactly what she needed to hear no matter what.
She hugged Lee back tight, loving the way his firm body felt against hers. The dress she had on showed off her long volleyball-player legs, and combined with her heels, made her ass look pretty great too. She picked the outfit out with Lee in mind. Her body reacted, as it always did, to Lee’s touch. His hand pressed against her lower back, holding her close, sent shock waves through her body. Her nipples hardened against his chest. She prayed he wouldn’t notice, as she had on no bra to cover it. When they pulled away, she was quick to cross her arms over her chest to hide his effect on her.
Being the person of honor that day considering she had just graduated from high school, she got to pick where they went to dinner. It was her favorite restaurant and conveniently Lee’s as well. Nobody had taken her seriously at first when she picked the old diner on the outside of town but Anna wasn’t one for fancy places. She would rather be here, a place she felt comfortable than some stuffy high class restaurant.
Dinner was great. She got to laugh and joke around with the people that meant the most to her in life. The only “problem” was that Lee’s hand kept brushing her knee or her thigh. She knew it had to be on purpose but each time was like a bolt of electricity going through her.
She felt herself grow wetter and wetter with each graze of his hand or his knee brushing against hers. She hoped nobody noticed the soft blush that was creeping up her neck.
Lee couldn’t help but stare at the gorgeous girl walking up to embrace him. The dress she wore showed more skin than he was used to seeing on her. When he pulled her to him, he got to feel that soft bare skin against his body. He felt his cock twitch. She felt like she belonged in his arms. She had watched her grow up for the last ten or so years.
She went from an awkward but funny girl to this jaw-dropping goddess. Her dress showed off her sexy, long, toned legs and her ass made him want to rip that damn dress off her. To everybody else, he was like a second father to her. They thought it was sweet the way he looked out for her. If only they knew the thoughts that ran through his mind every time he saw her.
Of course, he hadn’t always seen her this way. At first, she really was like a second daughter to him. Then one day, he took a second glance at her and realized she had grown up and was now this seventeen-year-old with a body he could stare at for hours.
The way she giggled made his body light up. Hearing her talk with him about hunting and fishing or watching her work by his side on the engine of her car, a line of grease across her cheek, about sent him over the edge every time. Being around her was one constant battle to hide an ever growing erection.
He couldn’t help but sit right by her at dinner. He let his finger “accidently” graze her knee or bare thigh. It was risky, touching her like that knowing it would not be hard to figure out it was completely on purpose, but he just couldn’t resist. That dress screamed “touch me” and a thousand other dirty things to him.
He put himself in real danger when dinner ended and it was time for everybody to head home. She came to him for another hug. His erection was not so noticeable just looking at him but when she pressed her body to his for that hug, he knew she had to feel it. Fuck it!
he thought to himself and pressed into her just a little, making sure she knew the effect her tight little body had on him.
Anna wrapped her arms around Lee to hug him goodbye. Shocked, she swore she could feel his hard cock lightly touching her. A moment later he pressed into her and she was sure of it. Her mind reeled. Was he hard because of me? He had to be, he sat rubbing my leg and thigh the whole time through dinner. He hadn’t even glanced at his wife. Who else would he be hard for? And why would he have pressed into me? Did he want me to know that he had gotten an erection for me?
They pulled away from each other before the hug got too long and made people think twice. Anna went around hugging the rest of the family along with Lee’s wife and then got tackled by Lee’s kids. She giggled as they knocked her to her knees, smothering her with hugs and kisses in the cheek.
Little did she know, the sight of her down on her knees glancing up at Lee about sent him over the edge. Quickly, and maybe a little too harshly, Lee rounded his kids up and pushed them all out the door. Anna worried she had done something wrong.One Month Later
Anna sat lounging at the local pool working on a tan when her phone buzzed beside her. She looked at the new text message. It was from Lee’s wife. Nelly: Hey Anna! Wondering if you were doing anything tonight? I’m going out with friends and Lee has to work late. Just wanted to see if you would be interested in watching the kids for us tonight?
Anna thought for a minute, knowing she had no plans. She missed the kids and could use the extra cash. They usually paid her pretty good. Anna: Sure, I don’t have anything going on tonight. What time do you want me there? Nelly: does 5 work? Lee works till 8 or 9 and I probably won’t be home at all tonight so I’ll just leave a check with him. Anna: sounds great, can’t wait to see the kids!
It was 2 P.M. now. That left Anna about two and a half hours to get home and find something to wear. Normally she didn’t care what she wore to babysit, but knowing the kids went to bed at 8:30 and Lee would be the only one coming home made her want to look at least a little bit sexy (nothing too noticeable or obvious).
It was 4:30 and about time for her to head over to babysit. Anna glanced in the mirror once more before leaving, making sure she looked okay. Her hair fell down her back in loose beach waves. Her skin had picked up a nice glowing tan over the past few weeks of summer.
She had chosen to wear minimal makeup, just a brush of mascara and a soft nude eye shadow that made her blue eyes pop. She wore tan shorts and a soft blue button up shirt. She had it buttoned almost to the top, knowing she could undo a few later that night, giving the outfit more sex appeal. Satisfied, she walked out the door.
Lee finally left work around 9:45, much later than he had anticipated. Feeling guilty for leaving Anna with the kids so late, he rushed home. He smiled when he walked in the door to silence. Lee was the first to admit that his kids were no walk on the beach. The only babysitter who could get them in bed by their bedtimes was Anna. Hell, she was one of the only babysitters they could get to come back time and time again. Most ran for the hills after one night with his four terrors. Anna however, adored them, making her ten times sexier in his mind.
“Anna?” he called softly, not wanting to wake anybody. There was no response. Walking into the living room, Lee found her sprawled out on the couch fast asleep. Her shirt had ridden up, showing of her tanned stomach and belly ring. And all but one button had come undone leaving him with an unhindered view of her breasts straining against her black lacey bra. His cock hardened. He just stood there staring at her perfectly sexy body and the way her lip poked out in a pout while she slept.
She looked like she was passed out pretty cold. Knowing it was taking another huge risk; he pulled his cock out of his pants and stood stroking himself as he devoured her body with his eyes. He prayed she would not wake up. Luck wasn’t (or maybe it was) on his side. Five minutes later he had lost himself in his pleasure, not taking notice to when Anna woke up.
Anna slowly opened her eyes, wondering what time it was and where Lee was. When she came to, she realized he was standing in the room staring at her in a daze with his bare cock in his hand, pumping it with his fist. Shocked she looked at her own body and what she must have looked like, her shirt halfway off, her shorts ridden up her ass. She grew instantly wet.
“Lee!?” Her voice snapped him back to reality.
“Oh my god. Oh shit! Anna! I..I’m so so sorry.” Lee fumbled with his pants trying to stuff his still rock hard dick back into his pants. It was no easy task.
Anna grew bold with this confirmation that she turned him on just as much as he did her. She stood, unbuttoning the last button of her shirt and slowly walked toward Lee. He stood in shock staring at her. She put a little extra sway in her hips as she walked slowly towards him, biting her bottom lip. When she reached him, she placed her hands on his waist and leaned up, ever so slowly, planting her lips on his. One simple peck and then she pulled away and just looked up at him, tugging her lower lip back into her mouth.
Holy fuck! Lee could not believe what was happening as he felt Anna's soft lips against his for the first time. She bit her bottom lip for the second time and he couldn’t wait more. Who the hell cared if it was wrong? He needed this girl like he needed his next breath. Lee reached out and tugged her to him, crushing his lips against hers, pushing his tongue into her mouth.
She responded with zero hesitation, opening her mouth wider allowing his tongue entrance. She kissed him back like her life depended on it. Her hands worked through his hair pulling ever so slightly. It felt like heaven. Lee gripped her ass and pulled her up. She wrapped her long legs around his waist and let him carry her, never breaking their kiss, to his bedroom. He laid her gently on his bed, kissing his way from the waist of her shorts up over her bare stomach to her neck, where he nibbled softly between kisses. Her moan about made him cum right there.
He made his way back to her mouth kissing her with all he had as his hips rocked into her, grinding his pelvis into hers. She arched her back under him, meeting each move of his hips. Her breasts, still restrained by her sexy black bra, rubbed against his tee-shirt clad chest. Reaching around, needing to feel skin on skin, she pulled his shirt over his head before reaching to undo her bra. He loved the way her hard nipples felt rubbing against his chest.
Lee’s breath caught when her soft hands snaked down and worked his jeans open, sliding them and his boxers down his legs, freeing his cock. She wrapped her hand around his shaft and worked it as she had seen him doing only ten minutes ago. Her hand moved up and down his shaft as her thumb circled around his head spreading his pre-cum around.
Not being able to stand that she still had clothes on while he was naked he ripped her shorts down her body, kicking them off the bed. There was not an article of clothing left between them. Her soft skin rubbing against him was better than he had ever imagined.
His hand roamed her body until it found her wet slit. Working his fingers inside her for the first time, he felt how tight she was. It took all he had to go slow with her and not shove his cock inside her right then. He pumped his fingers in and out of her while softly rubbing her clit with his thumb as his tongue found her right nipple, then her left.
Anna’s body writhed beneath him. She threw her head back moaning, attempting to be quiet to not wake the kids up. Her body tensed up beneath him. She was about ready to go into her first orgasm so he stopped abruptly, not giving her her release yet. She gave him a pouty look. That was it; he needed to be inside her now. Planting his lips back on hers in a soft slow kiss, he rammed his cock inside her incredibly tight pussy.
It was everything he thought it would be and more. She yelled out his name, digging her nails into his back as he pumped in and out of her. He held nothing back. He couldn’t. He had been waiting way too long to be inside this hot girl to show any restraint.
Her teeth dragged along his neck, kissing, biting, sucking, between her moans of pleasure. Her hips arched to meet each of his thrusts in time. Reluctantly, he pulled out of her but only long enough to flip her over so she was on her hands and knees with her ass sticking out at him.
She glanced over her shoulder and gave him a sexy little smile. He slammed into her once again. This time, she let out a small scream. Good thing his kids were heavy sleepers. Reaching around he let his fingers find her clit as he continued pumping into her hot wet pussy.
Her breathing came in pants rather than breaths. It turned him on even more. She was close. Three more hard pumps inside her and she was collapsing onto the bed, her body quivering with her orgasm. Lee continued pumping his cock with his hand until he was shooting his load across her back and ass.
He took a minute to catch his breath, lying beside her and rubbing his hand along her back and ass, working his cum into her skin. She turned her head and planted a kiss on his lips.
“Can I start babysitting more often?”
He chuckled at her sweet, innocent smile.
“Hell yes you can, baby.”
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