Author: Cheerleader Fan
Title: Unnamed draft
Summary: A 10 year old boy's life changes when his parents hire a sitter for the evening.
Keywords: fb cd voy nosex a russian girl and PANTIES!!!

Chapter 1

Timmy Johnson didn't know it yet , but his life was going to take an odd turn this evening. It was about 6PM on a Friday night much like any other. His parents were going out for date night, but his 12 year old sister Katie had already left for a friend's birthday/slumber party. This meant that she wouldn't be around to baby sit him and since he was only 10 years old his parents couldn't just leave him.

Earlier that day Timmy's parents told him they would be hiring a sitter and he was far from happy about it. You see, Timmy is a bit of a brat and the last thing he wants is someone bossing him around. This evening that someone would be Irina Volkov and Timmy could not have been more upset. Timmy only had Irina baby sit him a few times and he did NOT like it. Irina is 15 and the daughter of Russian immigrants. Her own parents were strict and that authoritarian mindset had rubbed off on her rather strongly.

At this time Timmy was in the living room playing video games. The doorbell rang and knowing it must have been Irina Timmy unhappily got up to answer it, pausing his game in the process. Timmy opened the door and sure enough there was Irina, a slender blonde girl who stood about a foot taller than his own four feet and change. Irina was nice looking, he had to admit, so at least there was one good thing about her. She had full lips, green eyes and a very light complexion, enhanced with the slightest bit of makeup. She was wearing a grey skirt and a pale purple knit top. Her body was the sort of fit physique you'd expect an athletic teenager to have. Her only fault, if you could call it that, was that her breasts were a little on the small side.

"Is your mother available?" Irina asked Timmy, a somewhat impatient look on her face.

"Come in," Timmy said curtly as he threw the door open. "MOM," he yelled  turning his head around so that she might hear him upstairs, "the babysitter's here." Timmy then runs off back to the living room and his paused game.

A few moments later Timmy's mother Susan comes down the stairs already dressed to impress. She's just wearing your standard little black dress, but it clings to her curvaceous body like a second skin.

"Hello Irina, I'm so glad you could make it tonight," Susan says, "I called around but all the usuals were busy so you're a godsend."

"It's my pleasure, Mrs. Johnson," Irina replies respectfully. "I wasn't doing anything tonight and I could really use the money."

"Well, Ward and I are sure glad you're free tonight," Susan continues. "The emergency numbers are on the fridge and please help yourself to whatever you want tonight. We'll probably be home pretty late, but I want you to make sure Timmy is in bed no later than 10."

"That will be no problem, Mrs. Johnson," Irina replies, "I didn't have too much trouble with Timmy last time."

"I'm glad to hear that. Most of his babysitters tell me he's a handful," Susan says with a laugh.

Just then Ward Johnson comes down the stairs and sidles up next to his wife. "Ready to go, honey?" he asks.

"Just about," Susan turns towards the living room and raises her voice. "Timmy, come out here,"

"HOLD ON, I'M AT A BOSS," Timmy yells back from the living room.

"Well pause it already," Susan calls back brusquely.

A moment later Timmy walks into the kitchen where his parents are with Irina. "What?" Timmy asks obviously annoyed.

"Well aren't we just a bag of sunshine?" Susan asks her son sarcastically. "Timmy, your father and I are leaving now and I want to make sure you're a good boy for Irina here, OK?"

"Fine" Timmy sighs.

"I suppose that'll do," Susan chuckles then turns to Irina. "Don't forget, bed by 10."

"And if he gives you any crap," Ward adds, "don't hesitate to send him to his room for a while."

"Yes sir, Mr. Johnson," Irina replies with a smile. "I'm sure he'll be good for me."

"We'll see you later then," Ward finishes as he and Susan step out the door. A couple of minutes later their car is speeding away and it's just Irina and Timmy in the house.

"So, you were playing a game? You can get back to that if you want," Irina tells Timmy and he turns to take off. "Before you go though, have you had dinner yet?"

"I'll just grab  something later," Timmy answers impatiently, desperate to get back to his game.

"Your parents put me in charge and I'm going to get dinner out of the way early OK? Now what do you want?" Irina asked Timmy again, obviously annoyed with his attitude.

"Quit being a bitch," Timmy sneers. "I said I'd eat later.

"Well that was fast," Irina replies in a stern tone. "Come here," she goes on as she grabs his arm and pulls him towards the living room. "On the couch, and if you're good for five whole minutes I'll forget any of this happened."

The two of them sit down on opposite sides of the large leather couch in the spacious living room of the Johnson home. Irina let out a deep sigh and looked towards the TV where Timmy's game is still paused.

"So what game is this, anyway?" Irina asks Timmy, all anger gone from her tone.

"Like you care," Timmy scoffs.

"OK then, go to your room," Irina tells him calmly. "I'm going to fix some sandwiches and when I'm done I'll come get you. Till I do I want you to think about why you're acting up like this. And no computer or toys."

"Jeez, FINE!" Timmy huffs and heads down the hall to his room.

Irina chuckles to herself and heads back into the kitchen to knock out a couple of sandwiches. Surely he can behave for the five minutes this will take, Irina thought to herself.

Not even five minutes later Irina opens the door to Timmy's room and finds him on his computer rapidly typing away on facebook, no doubt venting to one of his friends.

"A-hem" Irina clears her throat loudly. "I thought I said no computer."

"Why do you have to be so strict?" Timmy countered.

"Because as soon as your parents left the house you've been pushing me. I asked you if you wanted dinner and you gave me attitude. And clearly I can't even trust you in your room. Know what? Come here." Irina motions to the door with her free hand, the plate of sandwiches in her other."

Timmy slowly heads out the door and Irina follows him out. "K, now what?"

"This way," Irina orders and pushes open the door to Katie's room.

"Katie will kill me if I go in there," Timmy tells his babysitter.

"It'll be alright, it's just till you calm down. Go on in," Irina instructs him. "At least there's nothing for you to do in here but sulk." She hands him the plate of sandwiches and heads back to the door.

"How long?" Timmy asks, worried that he'll never get back to his game at this rate.

"It won't be long," Irina informs him. "Just be good and we can start fresh, OK?"

Timmy lets out an annoyed grunt and turns away from his babysitter. Irina just closes the door and heads to the downstairs bathroom. All this arguing really got to Irina and she almost didn't notice how badly she had to pee.

Inside the bathroom Irina reached under her grey skirt and pulled her iridescent blue thong down as she sat on the toilet. A moment later she heard the tinkle of pee as she emptied her bladder. Feeling much relieved Irina patted herself down with toilet paper and stood, pulling her panties back up and letting her skirt fall back in place. She reflected on how the night was going so far and decided she was being too hard on Timmy and would just let him back out to play his game.

Her mind made up Irina left the bathroom and headed toward Katie's room. She opened the door to find that Timmy had knocked down the pile of dolls and such Katie had decorating one wall of her room. Well, so much for letting Timmy off now.

"What on Earth are you doing?"Irina almost screamed at Timmy. Startled the boy turned, dropping the two dolls he was playing some kind of war games with. "You're going to clean up this mess right now, then I'll decide whether I should just send you to bed early or not," Irina continued.

"Come on, it's nothing," Timmy says reaching for the two dolls he dropped. "I'll get it later."

"No, you know what,"Irina tells him, her voice having calmed. "If you're going to play with dolls you may as well just be a little girl."

"Whattayamean?" Timmy asks confused and angry at the same time.

"C'mere," Irina says grabbing his arm again and pulling him towards Katie's closet doors. She throws one of the doors open and turns to Timmy, lowering herself till she's eye level with him. "Go ahead Tammy," Irina teases him, "pick out some clothes. For the rest of tonight you're a girl."

"No way!" Timmy shouts and tries pulling away from her.

"Fine then, I think this will work," Irina says pulling out a white blouse and a black three tiered skirt. She leads Timmy over to the bed and tosses the clothes onto it. "You're GOING to do what I tell you, Irina continues. "Or I'm going to break something and tell your parents you did it.

"You can't do that," Timmy says, his voice having lost much of its bluster.

"I can and I will," Irina tells him matter of factly, "unless you put on those clothes for me. But since you're being so difficult we can go get you a pair of panties, too."

"Nooooooo," Timmy whines. "Please don't."

"I don't know what else to do with you," Irina tells him. "And this time you're picking them out." Irina leads Timmy over to Katie's dresser and opens the top drawer. Sure enough it's chock full of the sort of colorful panties you'd expect a 12 year old girl to own. "Go ahead," Irina commands Timmy, who's just staring at his sister's drawer of panties with a terrified look on his face. Irina grabs his right hand and plunges it into the panties.

They're so... soft. Timmy thinks to himself as Irina moves his hand around the drawer. Not really even thinking about it Timmy puts his left hand into the pile of preteen lingerie and begins to explore them. A few moments later Timmy's hands come out clutching a pair of silky periwinkle bikini briefs.

"Those will do," Irina tells him. "I'll leave you to yourself so you can get changed. With that Irina heads out of the room, closing the door on her way.

Timmy just stares at the soft panties in his hand for a few moments then he puts them down on the bed next to the outfit Irina had picked out for him. His pulse quickens as he pulls his shorts down followed by his tighty whities. Timmy picks up the panties, steps into them and pulls them up his smooth legs. They pass his thighs and come to rest around his boyish little butt. They feel so different, Timmy thinks. Especially up front. They feel so nice against his tiny penis.

Timmy then directs his attention back to the bed, picking up the skirt and stepping into that as well. He pulls it up and ties off the little drawstring. It's a good thing that was there because Timmy was quite a bit smaller than Katie, so without it it's doubtful the skirt would have stayed in place. Timmy pulls his T shirt off and tosses it before reaching for the blouse. It was short sleeved, which Timmy was glad for, he didn't really care for long sleeves. Timmy slid his arms into those short sleeves and pulled the shirt to the front where he tried to button it. He was confused though because the buttons were on the wrong side.

"Almost done?" Irina called out from the other side of the door a few moments later.

"Umm," Timmy answered as he fidgeted the last button closed, "Yeah, I'm all done."

Irina opened the door and entered. Standing before her was a ten year old who may as well have been a girl. "Well, don't you look pretty," Irina said. "Here, let me help you with that." Irina came up to Timmy and began tucking the blouse into the triple tiered skirt. "Turn" she said as she continued tucking the blouse around. Timmy obediently began turning. Irina's hand slipped into the waistband of the skirt rubbing first his hip, then his bottom and finally lightly brushing Timmy's boyhood as she finished tucking him in. Timmy looked up at his babysitter as he blushed.

Irina stepped back a couple of feet and clapped a couple of times. "Very nice," she finally said. "Look," she pointed at the mirror in the corner of Katie's room. Timmy turned, following her hand and as he caught sight of the mirror a little girl looked back at him.

"Whoa," was all Timmy said. "That's me?" He shook his head as he said that and his somewhat shaggy hair shook, verifying that it was indeed him in the mirror.

"Give it a spin," Irina encouraged him, making a circle with her fingers. Timmy eyed the mirror again and pirouetted, the three tiered skit flying away from his waist as he did. "Pretty cool, huh?" Irina asked.

"Y... yeah... kinda." Timmy agreed.

"So," Irina continued, "How are you right now?"

"I'm... Ok," Timmy answered.

"Good, then how about we clean up this mess, huh? Don't want your sister seeing this, do you?"

"No," Timmy agreed and together the two of them wordlessly began cleaning up Timmy's older sister's room. The task completed Irina looked up to Katie's dresser checking the time. It was only 7:30PM in what was quickly becoming the strangest babysitting job of her life.

"I believe you have a video game to complete," Irina said and waved towards the bedroom door.

"Really?" Timmy asked. "I can?"

"Well, you've calmed down for me and you didn't even fight me when I asked you to help clean your sister's room. I think you've earned it."

"Thanks, Irina," Timmy said and ran towards the living room his skirt bouncing as he did. Irina grabbed the plate of uneaten sandwiches and followed her charge out of the room. Timmy headed straight for the living room and his game while Irina headed back to the kitchen. She pulled a couple of cans of Coke out of the fridge and headed into the living room.

Irina had a seat near Timmy, who was giddily playing his game. "So Timmy... or should I say Tammy? What game is this anyhow?"

"Ohh it's the new Resident Evil," Timmy replies, "and I guess you can call me whatever."

"You're taking this whole situation rather well," Irina praised Timmy. "Mind if I ask you about it?"

"Yeah, sure," Timmy says, pausing his game. He turned towards his babysitter and she gave him one of the cans of coke and one of the sandwiches.

"Do you like being dressed like this?" Irina started, an obvious question.

Timmy took a bite of his sandwich and thought about it a moment. "It's nice. I never realized how much nicer girl's clothes were than boys clothes. When you shoved my hand into Katie's panties they all just felt so... so I dunno... nice."

"Well I'm glad you like them," Irina told Timmy. "I like my girl clothes too. Like this skirt, here, feel it," Irina took Timmy's hand and put it on her skirt right where it rested on her left thigh. Timmy ran his hand over the silky material, careful not to move it too far from where she had put it. This was the first time he'd ever had his hand on a pretty older girl's thigh like this and it really exited him. "We girls get to have all kinds of nice clothes." Irina then gently took Timmy's hand off of her thigh and he laid it in his lap.

"Yeah," Timmy said in a bit of a daze. "You girls sure are lucky."

"So are you Tammy," Irina said. "Remember? I told you you're a girl tonight."

"Oh yeah," Timmy giggled, "I suppose I am."

"Hmmmm," Irina thought, "Oh here's one, are there any other clothes you'd like to try on at some point?"

"I dunno, what else is there?" Timmy asked his sitter.

"Well, Tammy, all kinds of things. There's bras, although you'd have to wear a training bra because you don't have any breasts," Irina motioned to her own not particularly impressive pair. There's all kinds of different shoes and stuff. Bikinis and other girl's bathing suits. And there's Lingerie, of course."

"What's lingerie?" Timmy asked innocently.

Irina giggle a little bit. "Do you know what sex is, Tammy?"

"Yeah, well, kinda," Timmy answered.

"OK, well lingerie is a special kind of clothing girls wear to make themselves look sexy," Irina told him. "It drives guys wild."

"That sounds neat then. I'd like to wear some of that," Timmy says excitedly.

"I don't think they make lingerie in your size," Irina tells him.

"These aren't really my size either," Timmy says. "Katie's bigger than me.

"Yeah, she is," Irina agrees. "Say, do you guys still have any of Katie's old clothes anywhere?"

"I think mom has a bunch of boxes upstairs in the attic."

"Let's go look," Irina suggests. "I doubt your sister wants you wearing her clothes anyway." Irina stands up as she finishes her sentence.

"Probably not," Timmy agrees. "Come here, attic is this way. Timmy leads Irina up to the second floor and to the end of the hallway. "It's right up there," Timmy says pointing to a trapdoor in the ceiling. He runs into his parents' room and returns with a chair. "Think you can reach it?" he asks his sitter.

"Probably," Irina replies as she steps onto the chair and reaches up. Her fingers just reach the handle and she pulls it down. "I'll go first," Irina tells Timmy as she unfolds the ladder prepares to climb it. "Hold it steady for me," she tells him. Timmy comes forward after Irina takes the first few steps and he grabs onto the ladder steadying it as best as he can. Timmy looks up and catches a perfect view straight up his attractive babysitter's skirt. At first he thought she wasn't wearing any panties at all till he caught a bright flash of blue material where her legs met. Aside from that little bit of fabric everything Timmy saw was sexy teenage flesh.

In a moment it was over as Irina reached the top of the ladder and stepped into the attic proper. after calling down that it was safe Timmy climbed the ladder reaching the top right about the time Irina found the pull chain for the closest light bulb.

"It's over here, I think," Timmy said and started to move towards the other side of the attic.

"Hold on," Irina said.

Timmy turned and looked at his babysitter. "What is it?" He asked.

"I just want to say I'm sorry for trying to blackmail you earlier. That wasn't right of me, but you were just being so difficult. I hope you understand."

"It's OK," Timmy assured her. "I was being a little shit." Irina smiled at that.  "Anyway, I think the boxes are over here," Timmy stopped at a collection of five boxes. Two were labeled Timmy and three were labeled Katie.

"Jackpot!" Irina said as they grabbed the three boxes of Katie's clothes. They each opened one of the boxes and started searching through them.

"I've got skirts and stuff," Timmy called excitedly.

"Mostly blouses and the like here," Irina responded.

The two of them turned to the final box and opened it together. Peering inside the both laid eyes on Katie's old panties training bras and a few pairs of tights. Irina reached in and removed a few of them uncovering a box within the box. Both of them were obviously curious at this so Irina removed the smaller box and began to open it. Inside she discovered a beautiful little dress that Katie must have worn to a fancy occasion.

"Ohh I remember that," Timmy said. "That's the dress Katie wore when my aunt and uncle got married.

"It's very pretty," Irina commented.

"I think it might fit me," Timmy went on. The wedding wasn't that long ago."

"Well let's get it downstairs and find out," Irina suggested as she put the dress back into the box. "Why don't you grab anything else you want and come on downstairs. I want to get a closer look at this dress."

"OK," Timmy agreed as he started going through his sister's old things and taking what interested him. What ended up interesting him was all of the panties, the training bras a couple of skirts dresses and blouses, so he just went ahead and packed it all into the box that had the dress and panties in it. He did his best to put the rest of the boxes back carefully and headed towards the ladder.

He peeked down through the trapdoor and saw Irina inspecting the dress. From this angle he noticed he was able to see just a little bit down her shirt, but since her breasts were pretty small he didn't really see much but the lace of her bra.

"Can you take this?" Timmy called down as he held the box of goodies. Irina folded the dress back up and gave him a nod so he carefully dropped the box down to her. Irina was able to catch it and placed it on the floor for now. Timmy climbed down and the two of them headed back to the first floor to go through what they had.

They ended up going straight to Timmy's room and began to sort though their haul of treasure. In all Timmy had brought down 14 pairs of panties in various colors and materials, six skirts, three dresses and five blouses, not counting the formal dress.

"I'd really love to see you in this," Irina told Timmy as she held the dress up. It was an ankle length dress coral in color with a zip closure rear and a bodice with medium sized straps and beaded with floral patterns.

"I would too," Timmy agreed as he began unbuttoning his blouse. "Could you turn around though? I'm going to change my panties after I take this skirt off."

"OK," Irina said as she turned away from him.

Timmy went back to task and stripped off the skirt then slid his sister's panties off of himself before picking up a smaller pair in pink that was actually a close match to the dress he was about to don. Timmy stepped into the new pair of panties and pulled them up. They were more snug than the pair he was wearing before and he really liked the way they almost gripped his bottom. They were also a little more snug up front, but since he didn't have much of anything there they weren't in any way uncomfortable.

"I think I'm going to have to help you with this dress," Irina mentioned. "There's no way you're going to be able to zip it alone. Are you decent?"

"Well, I have my new panties on anyway," Timmy informed her and Irina turned around to see him standing before her, nude save for the tiny pink panties.

"Gosh," Irina complimented. "I thought you were cute before. Now come on over here. I've got it unzipped just step into it for me." Timmy steadied himself on Irina's shoulder while she held the dress for him as he stepped into it. With both of Timmy's feet in the middle Irina lifted the dress up and assisted Timmy in getting his arms through the straps. "OK, Honey, turn around for me," Irina instructed and Timmy happily turned his back to her. Irina pulled the zipper straight up and it was done. The dress was a perfect fit.

Feeling the slight snugness around his torso Timmy knew he was fully secured in his beautiful dress. He turned toward his babysitter and smiled broadly as he showed off the coral dress.

"It's perfect," Irina said. "How does it feel?"

"It's so smooth," Timmy told her. "And a little tight up here," he motioned to his chest. "But it feels nice that way."

"Lets go out to the rec room," Irina suggested. "I have an idea and I think you'll love it.

"OK," Timmy smiled as he followed her through the various rooms till they arrived in the rec room. "What's up?"

"Gimme a minute," Irina said as she fiddled with the stereo that was along one wall. She fiddled with the dial till she found a station playing your standard classical music, complete with violins and horns. "Here," she said as she turned towards the pretty little boy across the room from her and extended her hand. Timmy came up to her and took her hand, not quite sure what she was doing. Irina placed her free hand on Timmy's waist and instructed him to put his free hand on her shoulder. She proceeded to lead Timmy around the room in a not particularly well coordinated dance. While Irina knew quite a bit about dance, her Russian parents being very particular about her learning it Timmy had no clue how to do it. Nevertheless the two of them had a blast dancing around the rec room for a good half hour or more. On one circuit of their dance Irina happened to notice that the clock on the wall read ten past ten.

"Shit!" Irina exclaimed.

Timmy looked up to his dance partner quizzically. "What is it?" he asked.

"Your parents wanted you in bed ten minutes ago," she informed him.

"Really? It's that late already?"

"Yeah it is," Irina said somewhat worried. "And we still have to do something about those boxes in your room. If either of your parents saw those they'd surely flip."

"It's alright, I got the perfect place," Timmy assured her. "There's a spot in the basement no one knows about that can easily fit all of this."

"Well that's good," Irina said. "We've also got to get you back into your own clothes." With that said she began to lead Timmy back to his room so they could straighten up.

"Can I wear my panties to bed?" Timmy begged as they made their way across the house.

"I don't see any harm in that as long as you wear them under your boy clothes and don't let anyone see them."

Finally back in Timmy's room Irina unzipped Timmy's dress and allowed him to step out of it. On impulse she gave his bottom a spank.

"Hey, what was that for?" He asked her, his cheeks a rather bright shade of red.

"That was for being a little shit earlier," she said with a smile. "I hope you never act like that to me again."

"As long as we can keep doing stuff like this I'll be the best boy you could imagine," Timmy assured her.

"So, you'll be my perfect little princess?" Irina asked with a laugh.

"Your perfect little princess," Timmy agreed.

"OK, princess, how about you go put your clothes on and help me with this?"

With no further prodding Timmy pulled his boy clothes on over his tiny little pink panties and helped his babysitter clean everything up. After the two of them stowed Timmy's new wardrobe in the basement Irina sent him off to bed. She even tucked him in and gave him a kiss on the forehead before calling him her little princess. she then shut off the light and closed his door.

Irina then headed back to the kitchen to grab a snack before hopping on the couch and watching TV and waiting for the Johnsons to return home. She sure was glad she took this job tonight. She hadn't had this much fun babysitting in, well ever. and to think, she mused, the Johnsons are paying me to do it.

End chapter one.