Training Lolita

"Hello, sir. I'm Destiny, the new babysitter that your wife hired. I know that she's still out of town, but I came by to make sure I knew where the house was, get a house key, and learn more about the kids I will be taking care of later."

John stood there, slightly shocked, but definitely turned on by this turn of events. Evidently, Dana had been watching the babysitter porn samples he had sent over. He also wondered how much her friends knew about what was going on.

John must have hesitated a bit too much for Dana, because she leaned forward and said conspiratorially, "I hope this is okay, Mr. T."

John grinned and joined the little play acting game. "I'm sorry. I forgot that my wife had told me she had hired a new babysitter who was going to come by. She told me that she was going to get you a house key. I have it inside. Please come in."

Dana walked -- no strutted -- by John, swinging her hips in the very tight spandex shorts that allowed the bottom of her ass cheeks to peek out. Her tits jiggled very nicely, too. John peeked out the door to see if anyone else was watching this teenage vision enter his house.

John followed her into the living room where she walked over to the big screen TV that had DVDs on some shelves under it. She bent over directly from the waist, keeping her knees straight, and studied the DVDs. Her feet were a little more than shoulder width apart and the display was fantastic and nearly pornographic. Her shorts rode up, letting John see more of her delectable bubble butt and they were so tight in the crotch that her pussy was discernable. No panties?

John stood back a few feet and admired the nice legs, terrific ass, and barely hidden pussy in front of him. Jesus, Dana was just learning about sex, but already knew how to push all the buttons.

John grinned and said, "See anything you like?"

"Ummmm. Maybe." Dana turned her head without rising up at all, leaving her bent over showing most of her wares. She wiggled her hips. "Do you?"

"Maybe."

Dana rose up and came over to John. She motioned him down to whisper in his ear. "How am I doing with this scenario?"

John backed up a little and looked into her eyes. "Fantastic."

Dana backed up and started sucking on her Tootsie Pop. She made a production out of licking it and then looked directly at John. "Just maybe?"

"Well, that depends on you, doesn't it?"

Dana grinned and put the Tootsie Pop back in her mouth. She motioned to the couch. "Sit down."

John sat down and Dana crawled up onto his lap facing him. She straddled him and looked him directly in the eyes, rocking her hips as she rubbed her barely covered crotch over his rapidly hardening cock. "I'll make this very clear, sir. I don't want to take your wife's place and I don't want to break you up. However, I have a proposal if you are interested."

John put his hands on her hips and pulled her down onto his hardening cock. "I'm interested."

Dana wiggled her hips and ground her pussy against John's cock. "Yes, I see that you are. Well, the proposal is this. You and your wife use me at least once a month for babysitting and I will provide other services as desired."

Dear God, where was she getting all this? It was right out of a porn movie. Maybe that's where she got it. "I'm listening."

"Well, I only charge $12 per hour for sitting the kid, but the charges for you are a little steeper."

"I'm still listening."

"You take me home every night after sitting and I provide the following: a blowjob is only $50 -- and I swallow; I'll fuck you any way you want for $100. I'm working on getting ready for anal so that will be $200, but only when I'm ready. What do you think?"

John ran his hands over Dana's ass. "I think I need to sample the wares before I make up my mind."

Dana stood up. "That's fine, but I charge even for samples. What do you want?"

"I want your best blowjob, right here, right now. I want you to kneel right here in the living room and suck me off."

Dana grinned. "No problem. Now take off your pants."

John stood up, dropped this pants, and stepped out of them. He was commando and Dana grinned.

"I like that. Easy access on the way home. I'll be able to suck your big, hard cock in the car with no problem." Dana smiled as she showed she could use the dirty talk and pushed John in the chest. "Now sit down and I'll show you what you get for your fifty bucks."

John sat and Dana knelt before him. She put her hands around his shaft and looked up at him. "Nice cock. I think I'm going to like licking and sucking on it." She ran her hand up and down the shaft and then grabbed one of John's hands. She put it on a pigtail. "Handles. Use them when you want to fuck my mouth and give me that big load. And I bet you have a big load that tastes great, huh? Do you? Have a big load for Destiny's pretty little cock-sucking mouth?"

"Yes, I do." John was grinning so hard he could barely speak.

"Mmmm." Dana didn't answer John clearly because she was bobbing up and down on his cock.

John leaned back and let her work. He just enjoyed it for a few minutes and felt that he could last a long time since she had serviced him on Tuesday and Thursday. He finally grabbed her by her pigtails and pulled her up. "I want to sample that tight, teenage pussy now."

Dana grinned and stood up. She rubbed her camel toe. "You mean this tight, teenage pussy?"

"Oh, yeah."

Dana turned around and walked over to one end of the couch. Fortunately, it had soft rounded arms. She bent over one, resting her elbows on it. "Come and get it. Your tasty, young pussy is served." She wiggled her ass as John moved behind her.

John put his hands on her waist. Fuck, this girl didn't need any training, just a little practice. She was going to give him a heart attack at this rate.

Oh, fuck it! John yanked her spandex shorts to the floor and Dana lifted one foot so he could get them off one leg. As he figured, she was commando as well. She spread her legs and John stared up at the now hairless pussy. Fuck! She had shaved everything!

John was more amazed each time he met with this little vixen. He ran his hand over her pussy and ass. "I love a smooth, freshly shaved pussy. It's gorgeous."

"Mmmm. All my daddies like my pussy cleanly shaved."

"Well, this one does, too. Now get ready to be fucked."

"Destiny is always ready to fuck, Mr. T."

"Good." John stood and ran his hands over the two gorgeous globes of her ass as his cock settled into the crack. "Fuck, this is such a great ass."

John reached down and grabbed his cock. He moved back just enough to be able to center it on Dana's pussy. He rubbed it around, dragging the head up and down her pretty little slit. He loved being able to do this to this sweet, young thing as she was bent over, hanging onto the arm of the couch. Finally, he started pushing it into her tight, pink cunt. It felt so good. It was like a nice tight glove sliding over his cock. It was so hot and wet, he was able to immediately start fucking her and drive his cock home.

John reached down and pushed her top up over her tits, freeing the gorgeous globes. He kept humping up against her ass as he reached under Dana and kneaded her tits. He pulled lightly on the nipples and she groaned, arching her back and thrusting her ass and pussy back even harder.

John stood back up straight and grabbed Dana by the hips, increasing the leverage he had to drive his cock deep into her. Dana responded my arching her back so that her pussy was more available. Fuck, this girl was hot.

John continued to drive his cock deep into her, his hips slapping up against her ass. Dana was starting to get vocal to continue the dirty talk.

"Fuck that tight, teenage pussy, Mr. T. Ugh! Oh yeah. Ugh! Pound it! Ugh!" And then she came.

"Cumming!!!" She managed to barely say it before her body started jerking under him and she just kept muttering and grunting as she went through a 30 second orgasm.

John held up and let her control her movements during her orgasm, but he was still very hard.

Dana surprised him when she suddenly rose up, his hard cock slipping free. He looked down and could see how wet it was with all her excretions. He watched as she knelt and also stared at his cock.

"Look at the big, hard cock. It's so wet from fucking my teenage cunt." She reached up and held it by the root and licked and sucked most of the juices off. "I love the taste of my pussy on a cock." She grinned and John just stared and groaned. She just started having sex?

"Now I'm going to finish sucking this cock so I can get that delicious cum that you promised me."

And so she did. Dana lifted his cock up and kissed his balls. "Okay, balls, give me your hot cum." Then she licked up the underside and buried about 4 inches into her mouth. John moaned and grabbed a pigtail with his right hand. Dana reached over and found his left hand and put it on her other pigtail. She grinned at him with her mouth around his cock and pulled his hands with hers, to demonstrate how he should use these handles to fuck her mouth.

And so he did. He used the pigtails to start thrusting into her face. Dana had been paying attention to the porn she had been watching, because she kept her right hand around the root of his cock so that he wouldn't gag her. John just kept thrusting, knowing that it wouldn't take long.

John just enjoyed the actions as she fucked Dana's mouth. Oh, fuck, this was going to be a good one.

"Oh, fuck. Here is comes!"

John thrust and spurted, his first probably being enough to fill her tiny little mouth. But Dana swallowed and kept sucking. John spurted and spurted and Dana just took it all. She swallowed every drop. When John finally finished thrusting, Dana took one last suck and sat back on her heels. John had almost collapsed, his legs feeling wobbly from cumming so hard.

"Yum. That's delicious cum, Mr. T. I hope you make use of my services regularly."

"Fuck! You are so damn hot Dana. You can drop the act. I need to sit down and rest."

He sat on the couch and the naked little vixen sat to his right and cuddled up to him. "Based on the amount of cum I just swallowed, I think you liked that scenario."

"Who wouldn't? That was fantastic Dana. I assume you got that idea from the videos I sent?"

She grinned. "Yep. And then I watched some other ones like that with Mel and Debra."

"And did you guys play a little?"

"Of course. I used one of Mel's dildos that is almost the same size as you. Debra used a vibrator, but then Mel got down and ate Debra's pussy until she came. I watched and got really turned on by that, but I didn't do anything."

"Why not?"

"I don't know. I'm still getting used to sex. I just want to fuck you right now."

They sat quietly for a while, then Dana spoke up again.

"I think Debra knows I am doing something with you."

"Why do you say that?"

"I forwarded the emails you sent with the babysitter videos in them and forgot to strip your email address out of one. I think she saw it before I hid it and opened the link."

"Did she say anything?"

"No. She wouldn't."

"Okay, but if you have to tell her, I don't mind. Just try to keep it quiet and not get to anyone else."

"Yes, sir." She snuggled closer. "I don't want to lose my lover when I just started."

John liked the sound of that. He pulled her close. "Me neither."

They were sitting there recovering, John in just a shirt and Dana completely naked when there was a knock at the door.