Oh Baby, Baby

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Mister Conaway gives the baby sitter her first time.
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Author's Note: As always, feedback and comments are great. I just wrote a story and submitted it yesterday, but I didn't like it so much. So, I wrote this one, hopefully to make myself feel better about my writing. Let me know what you think. Also, feel free to request a story, I'm always looking for inspiration.

*

She always wore clothes that to most men would be considered provocative. Falling victim to the fashion trend of leggins instead of pants left nearly nothing to the imagination. Her shapely legs, curvy hips, and that open space between her thighs all there for anyone who wished to view them. If she wasn't in those leggins that hugged her body tightly, the skirts she chose barely covered the smooth curve of her behind. Angela was not the babysitter Mister Kevin Conaway would have chosen to watch his kids, but he could not tell his wife that he found her to be too much of a distraction to keep around.

"The kids love her," she would tell him when he returned home from work, "She came highly recommended," he remembered her saying once.

Angela was just starting college and although she dressed like someone who was promiscuous, she was nothing of the sort. She enjoyed fashion and knew her body was good. She appreciated her youthful features and knew she wore the clothes well. However, the thought never crossed her mind that she might be stirring interest in the fathers of the many children she cared for. To Angela, it was a simply a job, a means to an end, and that end was money to buy more of the expensive clothes she loved so much.

Friday afternoon, Kevin Conaway left work with his wife on his mind. He had a pretty good day and feeling "in the mood" he figured they could turn the tv on for the kids and have a go at it upstairs. But the Los Angeles freeways had another idea in mind for him. Stuck on the freeway in standstill traffic, he found himself next to a car whose driver was a pretty young girl, one that reminded him of Angela. His wife slipped out of his mind and in her place he saw the shapely legs of their barely legal babysitter. Instead of clothed, he imagined her naked, walking around the house to clean up the kids' toys the way she always did before leaving for the night. he tried to be stealth as he reached into his slacks and rubbed his hand over the tip of his dick. He let out a sigh of relief, enjoying this feeling and imagining not his hand, but the much smaller hand of Angela. He felt his cock straining against his pants and heard a car horn honking behind him. He jumped to attention and saw that traffic was finally moving again. He grumbled angrily at the lack of release, but was happy to be on the way home to a woman who could finish the job for him.

Parking the car in the driveway, he grabbed his briefcase from the passenger's seat and held it in front of himself as he walked into the house, hoping to block what was left of his hardon and the wet spot left behind by precum from view. Where he would normally announce his arrival to the family, he wanted to surprise his wife, so instead he quietly entered and listened for where she might be. The sun was setting and he could hear not only the tv on in the family room, but also the water running in the kitchen. He set down the briefcase, removed his blazer, and silently as possible crept through the back door of the kitchen. Much to his surprise (and excitement) it was not his wife whom he found there, but Angela. His mouth began to water as he stood there and watched her bend over to pick up the dishtowel which she had dropped to the floor. The mini-skirt she wore rose up and exposed her white, cotton panties to his hungry eyes.

Kevin felt his dick stir even more in his pants as he listened to her hum, debating whether or not to touch her. He wanted to, boy did he want to. His fingers ached to reach out and feel the smoothness of her skin, and even more to feel the wetness he knew he could produce between her legs. Watching her wash the dishes, he imagined those small hands wrapped around his cock and had to brace himself on the wall. She was probably tighter than anyone he'd ever been with, he just knew it. He licked over his lips, practically drooling at the thought of burying himself deep inside her cunt. Christ, she was gorgeous. Her dirty blonde hair cascaded down her back in loose curls. He imagined tugging on it as she wrapped those full lips of hers around him, her perfectly pink tongue licking him.

He'd worked himself up into such a frenzy of need that he couldn't resist. Hoping that his wife would not be showing up any moment, he made his way across the kitchen with care not to hit any creaky spots on the floor. He wondered if she could feel him behind her, reaching around to touch the flatness of her stomach through her thin camisole.

"What the--" her voice seemed frightened as she turned her head to see him there, "Mister Conaway, you scared me," she said, assuming at that moment he would remove his hand. He must have thought I was Mrs Conaway, she thought to herself.

But he had made no such mistake. "Shhh," he put a finger to her lips and smiled, "Don't make a sound."

Angela sucked in a deep breath when she felt his hand move down from her waist toward her legs. She wanted to protest, but there was a deep, lustful look in his eyes. She blinked a few times and tried to steady her breathing as Mister Conaway's hand brushed against her thigh and slipped between her legs. Despite herself, Angela felt a wetness growing there, dripping out of her and onto the panties she'd chosen for the day in a tortuously slow manner. He seemed urgent, but not quick as he carefully pulled the elastic aside and his finger touched her moist flesh. She heard him let out a deep sigh as she sucked in, scared of what was to come, but also intrigued. She thought about telling him to stop, just as the rough tip of his calloused finger found her clit. She gasped and fell back against him, her light weight body easily caught by his strong arms, "Oh god," she mumbled as he pressed the finger harder against her clit, dragging it down to her dripping hole.

"Mmmm," he hummed in her ear, pulling the hair away from her neck so he could kiss her there as he moved further, taking her lack of argument to mean that she was enjoying herself as much as he was. "Fucking Christ," he mumbled after slipping his finger into her, "You're tighter than I ever could have imagined..." his voice trailed off as he slid a hand down her side and clasped her hand in his, feeling how tiny her own fingers were, "These the only fingers that have ever been in you?" he asked, bringing her hand up to his mouth to kiss her finger tips one at a time.

She shook her head, "No. My last boyfriend...he, um.." her eyes closed as she fought to find the words, "He fingered me a few times." She had to rest her free hand on the counter to hold herself up as he drew his finger out of her and took her juices up to her clit, using them to rub around it in tight little circles.

"Dirty girl," he said with a smirk against the soft skin of her neck, "and what about you? Did you suck his dick? There's no way he put his dick in this tight pussy...did he?"

She shook her head, "No. He asked me if he could, but I...I wasn't ready," she had brought her hand up to his shoulder and clenched the material of his shirt.

Conaway pulled his hand out of her panties and lifted up her skirt in the back so he could get a look at her ass, "This is the most stunning piece of ass I have ever seen," he squeezed each cheek in on of his hands and then smacked it gently.

Angela jumped at the sharp hit and turned around to face him, "Mister Conaway...the children...your wife..." She was clearly confused.

"Shhh, if you're quiet, they won't know. Those kids can't be torn away from the tv for anything."

She knew he was right, but was this right? How could this be okay? She'd hardly done anything with any of her boyfriends, but somehow this felt so good, so much better than the fumbling teenage boys who had touched her previously and could barely get through her kissing the tip of their dicks without cumming on the spot. She wondered what it was like with a real man, a man like Mister Conaway who so obviously wanted her.

"Let me see you," he whispered to her, pulling at her underwear to try and get it to come off. The panties reached her knees and she pushed them down the rest of the way with her foot, stepping out of them when they reached the floor. Out of habit, she reached down to pick them up, the wet spot in the center clearly visible. Kevin brought her hand, holding the panties, up to his face and sniffed it, smiling, "Such a sweet, musky scent," he said, all the while keeping his eyes locked on hers, "May I have them?" he asked so politely, as if he were asking for a second helping of dinner. She couldn't help but nod her head. He stuffed them into his pants pocket and reached out for her hips, holding them underneath her mini-skirt. Tugging her whole body closer to his, he reached around and squeezed her ass again before lifting her up on the counter. He pushed her thighs apart and felt his mouth watering with anticipation as he saw the perfect, untainted pink flesh of her pussy lips. His tongue slid out of his mouth, moistening his lips as he drew circles around her clit with one finger, never actually touching it.

"Please," she finally mumbled, her hands gripping the counter edge tightly.

He was surprised to hear it and looked up at her, "Please what?" he asked, wanting nothing more than to hear dirty words out of this innocent girl's mouth.

"Please, touch it."

"Say it, say what you want me to touch. I want to hear the words."

"My clit, please, touch my clit," she could feel the wetness dripping out of her pussy and onto the counter as he obliged her and finally touched her where she wanted. A happy sigh escaped her lips as she rested her head back on the cupboard behind her, "Yes, yes that's it."

He rubbed it in circles, then finally pulled her pussy lips apart and leaned down to lick from her hole up to her clit, stopping there to flick at it with his tongue. "Oh holy--" she closed her eyes, trying to steady her breathing, "What if someone--what if they come in here?"

But he wasn't listening. He was took busy pumping his finger in and out of her, lapping the flatness of his tongue against her clit. When he felt she was ready, he slowly entered a second finger into her, stretching her virginal hole just a bit more. "You like that, baby girl?" he asked, continuing with his gentle assault on her pussy until her body began to tense up, and then finally release in a way she'd never felt before. Looking up at her before bumping her clit with his nose, his tongue happily replacing his fingers at her entrance, licking up the juices that spilled out of her, "Mmm, it tastes like you do."

She nodded her head, unable to come up with any words to say in this moment. Instead, she scooted her butt closer toward the edge of the counter top, letting him know that she did, in fact, enjoy what he was doing to her.

"That's my girl. Now..." he narrowed his eyes as he watched her, pulling her off of the counter and setting her on the floor once again. "My turn," he unzipped his pants and lowered them along with his boxers, just enough for his dick to spring free of it's confines. Already hard as a rock, it stuck straight out, almost staring at her as she lowered herself to her knees. New at this, she was scared to mess up, but also felt like it was necessary for her to return the favor.

"I don't know how to do this," she admitted just before reaching her tiny hand out to wrap it around him, "Help me?"

"Oh, baby," he breathed out and nodded his head, "Keep doing that, rub up and down, yes that's it..." He swallowed hard as her soft fingers brushed the edge of the tip, "Lick it or kiss it," he urged her on, and with some hesitation, Angela leaned down and touched the tip of his hard cock with her tongue. "Lick around the head, yes, that's it," he repeated again, leaning back against the counter. As she instinctively took more and more, she could feel him growing harder in the warm cavern of her mouth. She liked the power she seemed to hold over him as he was barely able to stand when she combined the movement of her fist over his shaft and her tongue flicking at the tiny hole in the tip of his dick. "You sure you've never done this before?" He asked, almost out of breath as she started to move her hand faster and faster.

She pulled her mouth off of his dick, taking a gulp of air as she shook her head, "No."

"Well, baby, you're a natural," he smiled at her and then pointed at his dick, "Continue." But a second later he thought better of it, "Wait, no." He didn't want to come in her mouth. Well, he did, but he wanted to come elsewhere first. Her precious mouth would have to come later. Those full lips would find themselves wrapped around him again soon enough. "Stand up," he ordered her and took her by the hand, after pulling up his pants, and practically dragged her off to the downstairs bathroom. "Just in case," he said before shutting the door and locking it behind them.

Angela leaned her back against the wall, watching him, wondering what he would do next. The inevitable should've crossed her mind, but it didn't. Wasn't this already too much for a married man and his children's babysitter? Apparently not. Mister Conaway moved his hand down and pulled her shirt over her head, seeing her bra covered chest. He reached around her and squeezed the clasp of her bra, setting her breasts free as it fell away, "So beautiful," he leaned down and covered one of her breasts with his mouth, flicking at her nipple with his tongue. His hand held onto her other breast as he worked his magic, making her rest her head back against the wall. His knee found it's way between her legs, pushing them apart and rubbing the material against her softest spot. Despite herself, Angela was moaning, and she found that her hips instinctively ground against his knee. "You like that, eh?" he looked up from her breast and quickly grabbed onto her hips, lifting her up and placing her on the counter next to the sink. He pulled her forward so that her ass rested against the edge.

Pushing her legs open just as he had done before, Angela expected that Mister Conaway was going to lick her pussy again, and she was ready and willing this time. But, instead, she watched him pull his pants down to his ankles and kick them off, "Are you ready?" He asked, his eyes burning with lust as he held his dick in his hand.

"What?!" Her already white face turned even paler as she got a good look at the massive piece of meat in his hand. It would never fit inside of her. Never. "No, no," she shook her head, swallowing hard. She tried to close her knees together, but he let go of his cock to hold her legs apart.

"You'll be fiiiine," he said, trying his best to soothe her fears.

"Mister Conaway--"

"It'll be the best feeling you've ever had, I guarantee it."

"It's not going to fit, no no," she was fighting to close her legs, her eyes filling up with tears, "Please..."

But, instead of stopping, he leaned forward to kiss her neck, even nibbling at it slightly, his cock in hand once more, he rubbed it against her pussy, "Isn't that nice?"

Angela swallowed hard, shaking her head, but her juices were starting to flow again, she could feel it. She clenched the muscles inside of her tightly in an effort to close the entrance to her when she felt the tip of his dick press against her, "Oh god," she cried.

When he felt her tense up, Kevin dragged his dick slowly up from her hole to where her clit was peeking out of it's hood. He tapped the head of his cock against her clit, feeling her loosen up slightly. He smiled and without warning replaced his dick at her entrance and slid just the tip into her. Feeling how tight she was he fell forward against her, "Oh fuck, fuck," he mumbled, pressing his hand down against the counter to steady himself, "I knew you'd be tight, I knew it, ungh," and with that he thrust forward slowly, inching his way into her.

"No! Oh God, yes..." as he pushed in slowly and pulled out even slower, Angela found the intense sharp pain she'd initially felt starting to subside. Was this it? This wasn't that bad. In fact, it was starting to feel quite good. But then, before she knew what was happening, he pressed against her barrier, pulling all the way out of her and slamming back into her, breaking the last shred of her virginity. Angela felt herself being stretched apart as the tears rolled down her rosy cheeks. She grabbed a hold of his shoulders and dug her finger nails into his skin, trying to distract herself from the pain.

He held himself inside her for a moment, allowing her to adjust to the new feeling. Then, when her breathing seemed almost back to normal, he started to slowly thrust himself in and out of her. He reached between them and started to rub her clit as he did so, and Angela found herself moving closer to him, trying to create more friction.

"Yes!" She cried out, now in pleasure rather than pain as he rubbed her clit quickly with his thumb and slammed his cock into her, burying himself deep within her pussy.

"You're the best fuck...fuck," he ground their hips together, pulling her as close as possible. He could feel the muscles inside her start to clench down on his dick and he didn't know how long he could hold it together, "Cum with me, cum."

Angela didn't know how to make herself come with him, but she could feel that she was close, "I'm close," she said almost breathlessly. That was all he needed to hear. With that, Kevin was thrusting in and out of her quicker than he'd ever fucked anyone, at least that he could remember. Moments later she could feel him swelling inside her, "Oh my God," she threw her head back and juices spilled from her all over his cock as he shot his seed deep inside her. She could feel it hit the back wall of her pussy and mix with her own juices. It was the most erotic feeling she'd ever felt.

Breathless, the two held their bodies together. She rested her head on his shoulder, trying to breath and stay alive. She knew now, why they called sex little death, because she certainly felt like she had died, "Mister Conaway..."

"Shhh," he put his finger to her lips and then kiss her, sliding himself out of her, "That was amazing."

She could feel his cum seeping out of her pussy and down her leg, onto the counter, "You made me all dirty," she pointed between her legs to the messy mixture of their juices, "Do you want to clean me up?"

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CharrlaCharrla12 months ago

Not bad, but the actual sex part was rushed. It took all of, what, a paragraph or two? Draw it out more next time. And careful with "it's." Its only gets an apostrophe if it's the contraction for it + is. If you mean the possessive its (the dog bit its tail), there is never an apostrophe.

WriterOfRomanceWriterOfRomanceover 2 years ago

Very hot, but there's no "barrier" to "shred" the first time a woman has sex.

james3363james3363about 5 years ago
Only your second story? Wow....

Amazing story made even more so by you saying this was only your 2nd story! I've been on this site for years and you definitely have the ability to write well. Looking forward to many more from you. Perhaps a story where the guy and girl continually get close to getting caught many times to bud up the tension? I'm sure you could do wonders with an idea like that. Maybe under the table stuff that shows reluctance and then allowance? Keep writing and we'll keep reading more from you.

ldydvknldydvknover 10 years ago
Hell Yes

Love it. Perfect.

AnonymousAnonymousalmost 12 years ago
very hot

great story. made me so hot and wet!

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