Keeping Up with the Carmichaels

Of all the days for the Carmichael’s to want Linda to babysit, they chose tonight. OF COURSE they’d choose tonight! It was only the single most important night of her eighteen years of living, in her opinion! It was her 18th birthday, and she was planning on giving herself to her boyfriend Kevin after months of keeping him pent up and leaving him sexually frustrated. She spent the day doing her hair, getting her nails done, hands & feet, as well as getting some sexy underwear for Kevin to take off with his teeth. She giggled at the thought of that. But instead of driving up to the university to spend some well deserved alone time with the best boyfriend ever, she got stuck sitting for the Carmichaels, who unexpectedly had to leave their son Jimmy while they went away for the night. Mr. Carmichael was her dad’s boss, and if she did things like babysit, she knew her dad would be in his boss’ good graces when it was time for a promotion. So when she got a call from Michael Carmichael (yes that is his real name) she almost didn’t answer. But at four times the normal pay, she couldn’t exactly say no.

So, instead of the leather pants she was going to wear, Linda opted to wear her school uniform: a green pleated skirt from freshman year that was entirely too short for her nowadays, and a white button-up shirt that was impossibly tight. A plan started to form in her mind. The Carmichaels needed her to stay overnight, and she knew Jimmy would be asleep by the time she got there. So she could Skype Kevin, and then she could give him a little show. He’d been so patient with her; when she was the school slut his senior year & her junior year, he wanted her to stop sleeping with every guy that asked just to make her feel good about herself. So, she took a vow of chastity for him, and hasn’t had sex in over a year. But being a nymphomaniac, she masturbated frequently- three to four times a day, to be precise. She wore sweats under the skirt and a North Face jacket over the shirt so the Carmichaels didn’t wonder why she was dressed so provocatively. She packed a few toys in her purse, got in her car, and drove the two hours to the Carmichael estate.

Michael & Kate Carmichael lived at the end of the county line, in the richest neighborhood. Linda’s family was pretty well off, but the Carmichael compound made her feel dirt poor. Five bedrooms, five bathrooms, indoor & outdoor pools, and so many other amenities that it made you feel like you were in an episode of MTV Cribz. One night’s pay from the Carmichaels paid for her car. And she was about to get four times that tonight. When she walked in, Mr. Carmichael was putting the luggage in their Mercedes Benz. “Hey, Linda, you’re such a life saver! I got a last minute call from my partners in Manhattan, and they needed us to come sort some things out. So we’re hopping on a red eye to go do that, and we should be home by lunch time tomorrow. You weren’t terribly busy, were you?” he asked. Mike Carmichael was really cute to Linda. He had golden blonde curls all over his head, he was very tall, maybe six foot five, but she loved that he had a boyish charm about him. He always made people smile. If she could compare him to anybody, she’d say he loosely resembled Will Ferrell. With as much of a fake smile as she could muster, Linda stated, “No, Mr. Carmichael; I was gonna go see my boyfriend for my birthday, but it can wait until tomorrow.” Mike put his hand over his mouth.

Ohmygosh, it’s your birthday today? I’m such an asshole! How about instead of four times, we’ll bump it to five times normal pay. Call it a birthday present for my favorite employee.” He asked as he smiled, and she nodded and chuckled. He was the CEO of a multi-million dollar corporation, and had thousands of workers under him, including her own father, so the line about his ‘favorite employee’ made her laugh.
She walked in and hugged Mrs. Carmichael as soon as she saw her. Kate Carmichael was the type of woman that Linda modeled herself after. She was five feet nine inches of pure seduction & power. Kate was a New York runway model, turned mother, and co-owner of her husband’s million dollar business. She was just as involved in the company as Michael was. Linda dyed her hair red to resemble Kate’s striking Auburn hair a few months back. But as famous and cutthroat as Kate could be, she always made Linda feel like a girlfriend. Giving her hundreds of dollars in brand new makeup, thousands of dollars in clothe that she got from fashion week in Paris, and always sat and had “girl talk” with her whenever they saw each other, as Mr. Carmichael called it. “I’m so sorry we had to ask you to babysit on your birthday, Linda. And we’re running late, so we’ll catch up tomorrow when I get, yeah?” Kate asked as Lind beamed. “You remembered my birthday?” she asked as Kate stopped, looked at her, and came closer. She reached behind her neck, unclasped her necklace, and put it around Linda’s neck. It was a gold heart with diamonds completely covering the charm. “Of course I remembered. You’re only eighteen once! This necklace was given to me by Princess Kate Middleton during her last trip to the states. Now it’s yours; happy birthday.” Kate stated as Linda squealed and hugged her boss tightly.

They said their goodbyes, and Linda went to check on Jimmy. As usual, he was dead asleep. So Linda went into the family room and set up her laptop. She spoke briefly to her boyfriend, apologized for not being there, and promised to make it up to him, starting with a show. She took off the sweats, revealing her slender legs. The pleated skirt barely covered her ass, and she could see Kevin already rubbing himself through his jeans. She turned on First Time by Young Joc on her iPod, and started to slowly sway her hips in sync with the music. Her shirt was straining against the buttons, almost pleading for her to take it off. She was barely a size B freshman year, and now has a proud 36 C cup size, and the shirt only proved that she had finally grown into her beautiful looks. She worked hard for her tight frame, losing her baby fat in the past year, and she was showing it off well.

Linda danced seductively as the song progressed, showing glimpses of the sea foam green boyshorts that hugged her ass perfectly. Kevin was close to the screen now, wishing he could reach out & touch her, Linda guessed. Finally, she stopped, and ripped off her shirt, making buttons fly all over the floor, and revealing her matching green lacy bra. She heard Kevin groan, and it made her feel so sexy that this successful college football player was putty in her hands. She felt up and down her body, moaning softly for his benefit, and sat down in a chair that was directly in front of the camera. She reached into her purse, and pulled her favorite dildo. She could see Kevin breathing heavily now. He knew that this dildo was an exact replica of his cock; she made him make a molding of it when he left for college so that when she masturbated, it was like he was still with her. She licked the head, and quickly made it disappear down her throat. As she pulled it out, she saw Kevin couldn’t take it any longer, and fished out his boner from his jeans, and was stroking it, watching Linda suck his cock clone. Linda moaned as she let the dildo made a saliva trail down her breasts, made a quick stop at her nipples, and continued south to her dripping wet pussy. She’d never teased anyone so mercilessly; after so long, she’d usually just impale herself on his cock by now. But it was all worth it when she moved her panties to the side and inserted the dildo slowly inside.

She closed her eyes and let out a sharp hiss as the toy invaded her tiny opening. She was so wet that it slipped right in, accepting it all at full length. She moaned out Kevin’s name as they toy plunged into her repeatedly, making her hot with desire. She remembered that she was still putting on a show, so she opened her eyes to see three new sets of eyes on her on Kevin’s side of the monitor. She jerked up instantly, and covered her wetness. “WHAT THE FUCK, KEVIN! THIS ISN’T A PUBLIC SHOW!!!” She screamed as the other guys cheered and applauded. She heard one of them tell Kevin that Linda ...

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