The Housesitter

On her way to another babysitting job; she stopped at the store to make a few last minute purchases. She knew it would be several hours before the parents were home, so she made sure she had enough snacks and cigarettes to last. Soon she was on her way back to the car and to the house of her charge.

Quietly she knocked on the door, and the Lady of the House answered.

"Hi, Mrs. Brown, how are you tonight?" She asked with a friendly smile.

"Oh, I'm fine. Come on in."

Mrs. Brown opened the door and she walked in, careful to wipe her feet on the doormat.

"Could I talk to you for a minute?" Mrs. Brown asked.

"Sure..." she replied, unsure.

Mrs. Brown led her into the parlor and offered her a seat on the sectional. It seems Mrs. Brown was thinking she may be able to provide a little more service than just "watching" her son this evening.

"He's painfully shy, and we aren't quite sure what to do about it. We'd like him to meet a nice girl, go out with his friends - but all he does is sit in his room all night. I know he likes his computer, but there has got to be something else to help him come out of his shell."

"Well, what can I do?"

"We were hoping that maybe you could... teach him. You know, how to talk to girls, how to be comfortable around them. He has such a difficult time getting beyond his nervousness. Maybe you could help?"

"I can try," she answered, "I'm not sure what I could teach him..."

"Whatever you can do will help." Mrs. Brown said, "He doesn't know much and I'd love to see him gain some confidence."

"I'll do what I can." she answered matter-of-factly.

"Thank you. And of course, there's extra pay in it for you."

She smiled.

After Mr. and Mrs. Brown left for the evening, she waited a few minutes before venturing upstairs. The poor boy must be so painfully shy he didn't want to come downstairs, or he doesn't even know his parents have left. She looked around the house a bit, admiring a few paintings on the wall and looking at pictures of the young boy beautifully framed on the table. Finally she walked toward the stairs.

She walked up the steps slowly, looking at the pictures on the wall of the stairway as she climbed. Figuring the door with the posters and stickers on it was his, she knocked softly.

"Hello? Are you there?"

"What do you want?" the answer came back, with a nervous crack.

She pushed the door open slightly.

"Your parents went out... I wanted to let you know I was here..."

All she could see was the young boy's back - strong, sturdy shoulders and brownish-black hair. In front of him, she could see the glow of the computer screen. It looked like he was in a chat room. Music was playing also - beating, thumping hard-driving sounds that resembled someone trying to let out his deepest, darkest anger.

"Man..." he mumbled, "Doesn't she know I don't need a babysitter? I'm eighteen years old!"

"It's okay," she replied, "Don't think of me as a babysitter. I'm just a friend, come over to hang out."

"You're too old to be my friend, you don't even go to my school."

"Don't even think of that... look, I'm nineteen years old, we could be friends."

He looked at her for the first time, and she could see he couldn't get his eyes off her breasts - full and tightly constrained by her bra. The tight white tank top she wore didn't hide much either. She was glad she had worn it with the cut-off denim shorts she had made last summer when the jeans they came from were too long. They showed off her legs very nicely. He smiled.

"Okay... so, what's new?" He asked nervously.

"What are you doing on your computer?" she asked, inching herself a little closer to him.

"Oh, well, I was.. um.. just talking to some friends."

"About what?" she smiled.

"Um... girls."

"What do you say about girls?" Slowly she allowed her fingers to graze his arm as she reached to the monitor to turn it towards her.

"You know, just stuff. Every boy talks like he knows all about women."

"Do you?"

"No..."

"Why not?"

"Because I don't. I don't know anything about women. Girls don't like me very much."

"I couldn't imagine why..." she whispered into his ear, "You're so cute... I'd go out with you."

"No you wouldn't, you just want to make me feel better."

"No! I would", she said as she sat up, "All you need is a little confidence."

"Yeah, and where do I get that?" he smirked.

"Stand up." she demanded.

"What?"

"I said, stand up. I'll show you."

He stood up from his chair and looked at her curiously.

"Okay, now what?" he asked.

She leaned in closely to his face and he could feel her hot breath on his lips.

"Now, kiss me."

"What?"

"Kiss me."

"I couldn't... I ..."

"Kiss me. Now."

Softly he kissed her on the lips.

Immediately he blushed, and lowered his head.

Putting her finger under his chin, she lifted his head.

"It's okay..." she said softly, "Let Mommy help..."

She brought his lips to hers and kissed him again; softly, slowly. She parted his lips with her tongue and he let her tongue into his mouth. The kiss became a little harder, more passionate, and her hands began to explore his chest and arms.

She wasn't sure how much longer he would have let her just run her hands all over him – but she didn't want him to get too excited too soon. His inexperience might prove it a short venture already, she wanted to make it last as long as she could.

Slowly her hands drifted down to the front of his jeans. She could feel him getting hard already.

The boy took in a sharp breath when she touched his zipper; he felt a pure jolt of electricity go right through him when she brushed his cock through the denim.

"Oh my", she said, "Does that feel good?"

All he could do was nod, afraid to speak in fear this would end. Already his mind was racing; he was growing more and more excited by the thought. He only hoped he didn't lose control too soon.

She gradually lowered his zipper and pulled his jeans down to his ankles. Lightly, she pushed him over to the bed and he sat down with a bounce on the mattress. Next she removed his tennis shoes and pulled his pant legs off his feet.

"Socks, or no socks?" she asked playfully.

"Um... no socks?" he answered, unsure.

"Okay then..." she said as she removed them.

The boy sat, all at once amazed at what was happening, but afraid of not knowing what will happen next. Would she stop at any moment and tell him he was stupid for thinking she would do anything else to him? Would she continue touching and kissing him until he couldn't stand it any longer? Would he lose control totally and embarrass himself?

"Stop." She said. "You're thinking too much, I can tell. Lay down."

He did as she said, and reclined slowly, watching her eyes the whole time.

"Only think of what is happening now. Enjoy it. Don't analyze it."

As he lay down, she removed her tank top and calmly inched herself up on the bed over him. She reached behind her back and removed her bra, revealing her firm, medium-sized breasts to him. She sat next to his side, caressing his chest all the way down to his underwear elastic. Every time her hand was near his pelvis, she could see his cock jump with a shiver of excitement. She knew it was time to teach him something.

"So... did a girl ever kiss you... down there?" she smirked, nodding her head towards his cock.

All he could do was gulp and shake his head.

"Pity..." she said, "Maybe 'Mommy' should do something about that..."

Her head lowered down to his chest and she kissed a line down to his underwear.

"Looks like something is in the way..." she whispered.

Quickly she pulled down his underwear; unzipped and removed her shorts and put her hands around his long, firm cock. The touch of her fingers made him gasp, and she smiled.

She again lowered her head to his cock and she allowed just the tip to touch her lips.

"I've been told I'm good at this... so remember it to compare to all the other girls who will be doing this to you..."

Her tongue playfully rubbed the head of his cock, and the pleasure was almost too much for him to bear. He felt the urge to grab her head and push her down onto his cock, but he knew he couldn't do that... yet.

She felt him squirm a bit when she teased his cock and she liked the way he wiggled. It was all she could stand not to just swallow him down her throat and let him cum in her mouth as soon as he was ready; but she knew she wanted to take her time. After all, she was his first.

While her tongue still caressed him, she took him deeper into her soft, warm mouth. A small moan escaped her throat and he shivered again. She moved her head up and down, slowly at first, gradually gaining a more passionate pace as she worked him with her tongue at the same time. She could feel his cock pulse in her mouth; feel every vein bulge with pleasure. Small tastes of him on her tongue made her work all the more. Growing more and more frantic with her moans of pleasure, she continued moving at a faster and faster pace. Soon his hands were in her hair and she moaned louder still. She reached one of her hands down between her legs and began to play with her pussy while she sucked his cock harder and faster.

He moaned so loud she thought he would scream. She knew he was going to cum soon, and she wasn't quite ready for that to happen. Quickly she raised her head and stopped.

"Wait a minute." She said, "I'm not ready for you to finish yet."

His eyes showed the mix of pain and pleasure he was feeling. That felt so good he didn't want it to stop, but he wanted the release that orgasm would bring. He wanted it so badly he could almost taste it.

"Let me..." he said. "Let me do that to you..."

"Are you sure?" she asked. "Have you done that before?"

He blushed and lowered his head.

"No, I haven't." he said. "But I want to. Teach me how to..."

She smiled again.

"Okay... let me lay down."

He sat up and moved over, so she could take his spot on the bed. She removed her thong and lay down.

He was amazed at how beautiful she was, as he watched her lay there, spreading her legs for him. He could smell the wonderful, musky aroma of her pussy and he swooned a bit.How could this be happening?He thought.

Right away, he maneuvered himself between her legs and lowered his face down to her beautiful pussy. Unsure of what to do next, he looked up at her.

"Use your tongue," she whispered. "Touch my clit gently with your tongue, caress it. Then after a few minutes, you can do it a little harder. Not too hard, or it'll hurt."

He did as she said, rubbing his tongue gently along the lips of her pussy, to get it wet and to get used to it. She tasted amazing! He couldn't believe a woman tasted so good. He found her clit with his tongue and began slowly to play with it, caressing it, flicking it softly, and finally rubbing it a little harder and softer, in alternating paces. She was moaning, so he imagined he was doing it well. A moan or two escaped from his lips as well, and he could feel his cock throbbing with desire. She began to moan more often and louder each time, and soon she was clawing at the bed sheets and writhing with passion. He felt her pussy get really wet, and realized she was cumming. He smiled while still licking her, both proud and incredibly turned on. He had never made a woman do that before.He had never made a woman do anything before,he thought to himself. After a few minutes, he had to stop or he felt he would burst with excitement.

"Please...let me fuck you." He said.

She panted and moaned again.

"Please...fuck me." She said in a raspy voice.

He climbed awkwardly over her, and rubbed his cock on her still extremely wet pussy. He felt himself slip so easily and gently into her; he almost came at the sheer feeling of the inside of her. Slowly he pumped his hips and felt her raise her hips up to meet him. Their pace was very slow and steady at first. She talked to him while they fucked.

"Now, don't go too fast too soon... you don't want the fun to be over before it even begins, do you?"

He shook his head and closed his eyes, enjoying the feelings washing over him. Her pussy felt so good! He could hardly stand it. He wanted to fuck her so hard, but didn't want this wonderful feeling to ever end.

Their pace soon became a little more hurried, and both panted and moaned together, louder and louder. Her hips began to buck faster and faster, he had to steady himself up on his arms to keep pace with her, moving his hips faster and faster just to keep up.

"Oh..." he moaned, "Oh... I'm going to cum soon..."

"Oh yes!" she cried out, "Cum inside me! Oh, it feels so good..."

That was almost too much to bear and he thought he would lose it right then. He continued to fuck as hard as he could, holding on as long as he could.

She grabbed his hair behind his head and growled into his ear.

"If you cum inside me right now, I'm going to cum again too."

With the loudest moan he's ever heard escape his own lips, he couldn't hold on any longer. Her voice in his ear was all he could stand and he thrust his hips one last time – hard and deep inside her. He could feel himself shooting into her – his body convulsing and his voice moaning and growling louder than he ever thought was possible. Occasionally his hips would buck and convulse beyond his control and it was all he could do to keep from falling right over. She was moaning and calling out his name as she came over and over in waves. She could feel her pussy pulse as each wave of orgasm overtook her body and seemed to swallow him inside her. Her fingers clawed at his back, and she pulled at the bed sheets. They moaned together as they came together, holding on to each other and writhing together.

Soon their pace slowed more and more, until finally they lay still; him still inside her and both panting hard.

She smiled.

"Did you learn something?" she asked him, grinning slyly.

"Yes, I did."

"What did you learn?" she asked.

"Sometimes it's good to have a babysitter." He grinned.

They both laughed as he rolled over onto the other side of the bed.

"Sometimes it's good tobethe babysitter, too." She said.