Babysitter With Benefits

Tiffany rolled over in bed, brushed her curly, dark brown hair from her face, and looked at the clock. It was seven o'clock in the morning, but she had nowhere to go now that she had gotten laid off from her job.

Despite her young age of only 23, she really enjoyed her marketing manager job. In this prestigious role, she spearheaded various clients and projects, wrote copy for advertisements, ran online promotional campaigns, and so much more. She was upwardly mobile that is until she got the axe. One day she was working and happy. The next, she was home hiding under the covers or scouring the web for her next opportunity.

She finally got up and walked into her living room, and there it was staring at her from the table--her checkbook. Numbers ran through her head, most of them subtractions from her bank account to pay bills. With the little amount she made from unemployment, she knew that she couldn't keep on paying them for long.

What was she going to do? She remembered back when she was in college, she used to babysit and made a small fortune because she was so good with the little ones. She loved kids and one day hoped she would have some of her own, though she still hadn't met the right person yet.

She briefly thought about jumping into babysitting again, but that would be going backward in life, not forward. And that wasn't right. But she needed the money in order to stay in her apartment. The last thing she wanted to do was move back in with her parents. She decided to continue looking for another job in marketing, but babysitting as a stopgap couldn't hurt.

Tiffany rummaged through her paper mess and pulled out her old black address book. She started to flip through the crinkled pages, using her delicate fingers to jump from entry to entry. With a sigh, she picked up the phone and started to make some calls. The phone line rang. A man picked up the phone and answered.

"Hello, is this Mark?"

"Yes, it is."

"Mark! It's so great to speak with you again. It's Tiffany. You remember me, right? Your old babysitter!"

"Oh! Hi there. I thought you would be conquering the corporate world by now."

"Yeah, well. My circumstances have changed a bit recently. I was just calling to... uh... ask if you needed a babysitter for your little one this weekend."

"She was just a little peanut when you babysat before, but she still needs some supervision. Why don't you come by on Saturday night? Say, eight o'clock?"

"Sure! That would be great. I'll see you then."

Tiffany hung up the phone, delighted that if she had to go back to babysitting that at least it would be for a family she liked and a little girl she enjoyed spending time with.

If this gig went well, she'd reach out to her other customers and see if they needed her babysitting services.

***

Saturday came around quickly and Tiffany took the time to get herself ready. She hadn't seen this family for the past five years or so and wanted to make a good impression. She put on one of her pretty polka-dot sundresses, carefully applied a light dusting of makeup, just for the sake of appearances, and hopped into her car.

As she was driving, her hands became clammy. She didn't think she'd be so nervous to babysit again, but her body was telling her otherwise. At the next stoplight, she found a tissue in her car and wiped her hands. Practicing some breathing exercises, she was able to calm herself down.

Arriving at the house, she parked in the driveway just like she did all those years ago, got out, locked the car, and headed to the front door. When she arrived, Mark was already standing there waiting for her.

"You look pretty tonight," Mark said, getting lost in her bright blue eyes and taking in her dainty dress.

"Thank you," Tiffany replied, blushing. "Where is Anna? I'd like to say hello to her."

"Oh, you don't know, do you?" Mark replied, a frown creeping onto his five o'clock shadow face. "Anna and I broke up about a year ago."

"I didn't know!" Tiffany exclaimed, putting her hand over her mouth. "I'm so sorry to hear that, and I'm also sorry for bringing it up." Secretly, she wanted to know why they had broken up, but she didn't dare ask. It really wasn't any of her business.

"You didn't know. Don't worry about it. Why don't you come in?" Mark looked down at the floor as she entered the house.

Tiffany wanted to make a good impression and she hadn't started off very well. She was just trying to make small talk and it backfired. OK, so she wouldn't talk about anything unless it had to do with the little girl. That way she wouldn't cause any more commotion.

Mark led her to the living room where his daughter, Kayla, was watching TV. "Kayla, look who's here!" he said.

"Tiffany!" Kayla exclaimed, running over to the babysitter.

"Hey there, kiddo! It's so good to see you again!" Tiffany picked her up and gave her a big bear hug.

"You two be good tonight," Mark said, walking back to the front door and grabbing his coat. "I shouldn't be later than midnight. It's just a boys' night out."

"Sure thing. We're gonna have lots of fun. Aren't we, Kayla?"

Kayla nodded her head and smiled a toothy grin.

The rest of the night was uneventful. They played some video games, watched some cartoons, and, when it got late enough, Tiffany walked Kayla to her room and read her a story until she drifted off to slumberland.

Once she was completely asleep, Tiffany went back downstairs to clean up the mess the two of them had made. She didn't want Mark to see the house in such disarray.

As she was disposing of all the food wrappers and organizing all of the video game cases, she heard a noise at the door. With a few games still in her hand, she went over to investigate. She heard another thud, and then the sound of keys jingling and the deadbolt turning.

Seconds later, Mark came through the door. He was home early. It was only ten o'clock. He hadn't been gone for more than a few hours. Tiffany was a bit disappointed because that meant she would make less money for the night.

When Tiffany took a closer look at Mark, he seemed a little unsteady on his feet. "Mark? Are you OK?" She went to help him when he staggered.

"Yeah. Yeah. Suuuure. I'm goooood."

"Can I help you with anything?" At this point, Tiffany could tell Mark was drunk and slurring his words. "Do you need anything before I go?"

"D-Don't go yet," he said. "I do need something. Let's sssit on the couch." Mark started to walk into the living room, but before he made it to the couch, he fell onto the hardwood floor. Tiffany rushed over to help him up. "I'm sorry," he said.

"Don't worry about it, Mark," Tiffany said, trying to help. "Let's get you up."

"You grew up to be one b-beautiful woman, Tiffany. You know that, right?"

Tiffany smiled at him, taking the compliment, but she didn't know what to say in response. Instead, she just focused on getting him back on his feet. Once he was standing again, she leaned against the back of the couch to steady herself so she could keep him upright. She was much smaller than he was.

Mark fell forward and his body pressed up against Tiffany's, her ass now pinned against the back of the couch. As they stood there, she continued to help him regain his balance, but it was then that she felt something in his pants poking her.

"Thank you, Tiffany."

"For what? I'm just trying to help. Anyone would do the same."

"Well, thank you for being here with me. I went out with the guys tonight and they said it would be hard me for to find anyone else to be with since I have a kid. They said no one wants a premade family, a kid who isn't theirs. And no one is going to want me."

"That's ridiculous, Mark. Don't listen to them. Any woman would be lucky to have a man like you."

"They would?"

"Yes, absolutely. You're a smart guy. And you're very handsome." Tiffany looked him over and, for an older man, he still had all of his hair and none of it was turning gray. She stared deep into his brown eyes, noticing for the first time there were flecks of amber that made his eyes come alive in the low lighting. As they gazed at each other, he spoke again.

"Would you?"

Tiffany didn't know how to answer. She thought he was attractive, but he was so much older than she was and she wanted to keep things professional. "Of course, yes, I would, but I'm just your babysitter, nothing more."

"I'm so glad to hear you say that because, ever since Anna left, I haven't been with anyone. I mean, yeah, I've had a date or two, but I haven't been... you know... naked with anyone. And when I saw you again, man, such dirty thoughts ran through my mind." Mark leaned in to get closer to Tiffany. "I'm going to kiss you now."

Tiffany, surprised by the kiss, pulled her head back. "Mark, I don't know what to say." A stunned Tiffany was frozen in her footsteps.

"You've already said everything I wanted to hear." Mark kissed her again while his fingers found the bottom of her dress and quickly ran up her bare thighs.

Tiffany's heart started to beat faster and faster from his touch. At the same time, her brain was working overtime processing the heated turn of events. She knew this was wrong, but she needed this gig to help pay her bills. She was just supposed to be the babysitter for his kid, but now things had gotten out of control and she couldn't say no. In fact, all she wanted to do was say yes. Forgetting about her worries, she wrapped her arms around his shoulders and began to kiss him back.

His fingers made it from her thighs to her soft, supple inner thighs and then brushed against her panties, which were getting warmer and wetter by the moment. "Oh yeah," Mark whispered into her ear.

Tiffany let out a quiet moan as his fingers went underneath the fabric of her panties and came into contact with her tingling mound.

Seconds later, he pulled his fingers back. He proceeded to pick her up and sat her on the top of the back of the couch. With one hand he held her in place and with the other, he slid off her panties and unzipped his pants.

That was the first time she saw him. His bulging cock was standing at attention and she spread her legs wide for him, leaving no doubt about what she wanted.

With his pants around his feet, he returned to Tiffany, used both hands to lift her off the couch and, with his cock directly in line with her vagina, impaled her on his hard rod. A loud moan escaped their lips as Mark buried his cock in her pussy and his tongue in her mouth. His daughter was asleep upstairs and he didn't want to wake her up.

Tiffany wrapped her arms and legs around Mark tight, allowing him to penetrate her so deeply it made her moan again. After hearing her moan a couple of times, he started to thrust faster and harder making Tiffany moan even louder.

Mark then stopped abruptly, putting her down. "You have to be quiet. I don't want anyone to hear us," he said, pointing upstairs.

"Right. Quiet. I got it." Tiffany smiled.

"Maybe we should go into the half bathroom. That way we can lock the door."

Mark grabbed her hand, pulled her into the bathroom, closed and locked the door, and pushed her shoulders forward so that she was leaning on the back of the toilet.

Despite not facing him, she could see his reflection in the mirror that spanned the entire bathroom wall.

"Give me a minute," Mark muttered, and then went to the cabinet under the sink. He pulled out some sort of weirdly shaped object. It had what looked like a plastic o-ring and a very long dildo on it.

Tiffany never used toys when she dated someone or even when she masturbated so seeing one was a shock and a turn on. He then pulled out a clear bottle and squirted the clear liquid in his hands and onto the toy. "You're gonna love this." He pushed her shoulders back down so that she was hunched over the back of the toilet again.

"What are you doing back there?" Tiffany asked, turning her head around to catch a glimpse.

"Don't look," Mark said. "It's a surprise."

She tried to see what was happening using the mirror, but her own ass was blocking whatever he was doing behind her. Then she jumped when she felt his fingers over her asshole and gasped when he slipped one of them inside her.

"What's the surprise?" she asked softly, excitement starting to build within her as he stimulated her sensitive nerve endings.

"You'll see," he said, grinning.

Suddenly, his finger left her little pucker, but she could feel herself getting wetter and her juices began to run down her leg.

"You liked that, right?" he asked.

"Uh... Umm... I don't—"

"You know, you're just embarrassed. Don't worry, you'll get over that real soon."

As Tiffany was standing there, legs spread for Mark, she first felt something larger and hotter than his finger trying to push into her asshole."

"Oooo," she uttered.

"Just relax, OK? Relax and let me in."

He pushed harder into her tight little ass until he split her open and could move freely in and out. "Oh yeah, Tiffany. You are so sexy," he whispered into her ear.

And then she felt something larger and longer enter her slick pussy. Was that the dildo she saw before? The tingling sensations that ran from her pussy down her legs and up her torso threw her body and mind into overdrive and she couldn't think or be still anymore. All she could do was wiggle and squirm underneath him and enjoy the ride.

He was fucking her from the front and behind at the same time. The feeling was euphoric and she had trouble controlling her body. She held onto the toilet to support her.

Several times, Mark stopped his thrusts and grabbed her hair, pulling her head back to kiss her, dipping his tongue in and out of her mouth. Then he'd let go of her hair and hold her hips, thrusting and grunting behind her, his cock and the dildo rubbing against all of her sensitive, naughty parts.

At one point, the dildo brushed against such a sensitive part, Tiffany started to buck against Mark and her whole body began to tense up. "G-Go faster, don't stop, please," she moaned.

"I don't know how much longer I'm gonna last. You're so tight," he said. Mark did his best to keep going, but the feeling and the pleasure was just too much for him to handle and he came in her ass just as she orgasmed all over the dildo still in her naughty vagina.

Tired and sweaty, Mark leaned on Tiffany, still supporting herself with the toilet. He grabbed her breasts and squeezed them, pinching her nipples making Tiffany jump at his touch.

After a few minutes, Mark caught his breath. "Are you available to babysit tomorrow night?"

Still recuperating and unable to speak, Tiffany nodded her head and smiled.