Flirting with the Sitter

Introduction:
“Hello, Mr. Peterson,” Billy said as the door opened. The Petersons were friends of his parents and when their regular babysitter cancelled, they asked if Billy would be willing to look after their kids. Billy hadn’t done any babysitting in a year, not since getting real summer jobs, but he was home this weekend from college and didn’t have any other plans tonight. Besides, Tim was in 1st grade, so it wouldn’t be like taking care of a baby. He expected to spend most of the night lounging in front of the TV making sure the house didn’t burn down.
“Hello, Billy. This is our son, Tim,” he said referring to a short, scruffy looking 7 year old standing behind him, “and our daughter Sarah is downstairs.”
‘Sarah?’ I thought? ‘I’m stuck with two kids now?’
“Tim goes to bed at 8, Sarah at 10. Make sure she finishes her homework before then. We’ll be home around 11.” He continued on.
Anyway, I was getting a little grumpy inside. Instead of being able to send the kid to bed early and then lounging about, I’m going to be stuck with her underfoot most of the evening. I knew there was a catch.
I briefly wondered why they needed a babysitter at all, but I guess that while Sarah might be old enough to stay at home, they didn’t think she was old enough to look after her little brother on her own.
Anyway, Tim and l went downstairs to the living room. Tim ran off to the far end of the room where a mini basketball hoop was set up. I saw Sarah sitting at the coffee table in front of the TV (which was off); her flowing blonde hair that went down almost to the floor. She was wearing a loose shirt and a skirt, with just the hint of a figure developing underneath. She was sitting on the floor cross-legged such that I could see most of the way up her skirt.
I wondered if she knew what kind of view she was giving me, when she shifted her legs to a more modest pose. I then saw her glance up at me and smile.
“You wanna play ball,” Tim asked, and that seemed as good an idea as any. We played one-on-one for about half and hour. It’s surprising how competitive a game can be between a 7 year old and a 20 yr old confined to his knees the entire game. Just as I’m about to take a long range shot, I feel something swat the ball out of my hand.
Sarah is standing behind me, holding the basketball that she pilfered from me, grinning like the cat that ate the canary. Tim started laughing as Sarah dodged around me heading towards the hoop, laying the ball up in the basket.
I picked up the ball as it rolled back to me, and both Tim and Sarah take positions between me and the basket. I make a feint to the side and then try to push between them. Tim runs towards me and jumps on me, but he can’t pull me to the ground. I try to continue on towards the hoop when Sarah also jumps on my back. This knocks me to the ground and both of them fall on top of me. As we land on the ground, I can feel her soft body roll over me. She lands upside down, with her shirt lifted halfway up her body, and her skirt lifted high enough to flash me a view of her panties. She seems to pause for a moment, letting me enjoy that view, before getting up and fixing her clothes.
I glance at the clock and see that it’s just after 8pm. “Time for bed, Tim,” I say. I follow him upstairs as he gets ready for bed. I read him a bedtime story, “One Fish, Two Fish, Red Fish, Blue Fish.” (I think kids like that book, not because the book is interesting itself, but from how much trouble parents and sitters have pronouncing all of those tongue twisters.) After getting him tucked in, I close the door to his bedroom and head down the hallway back towards the stairs.
I hear someone come up behind me. “Now that Tim’s in bed, what adult games are we going to play?” Sarah asks.
Well, I was hoping she would stay out of the way and I could just relax, but instead, she’s still pestering me. “What do you know about adult games?” I ask.
“I know this,” she says and gives me a hard kiss. I chuckle at the effort. “What?” she asks.
“That’s not much of a kiss. You just pushed against me and squeezed. It’s like a little kid kiss.”
“Show me a real kiss then,” she retorted.
Maybe this is the easiest way to get some peace. I bent down towards her and pulled her face towards me. I kissed her hard, forcing my tongue in between her lips and running it over her teeth and around her tongue. One hand was holding her head in place while the other one ran down her back and gave her buttock a squeeze. I was rougher than I normally am, but I wanted to make the impression on her.
As I disengaged, she stood there in the hallway looking stunned. I left her there and went downstairs, sat on the couch, and turned on the TV. As I’m flipping channels, I wonder if I went too far, but I figure she’d recover soon enough.
I see Sarah slowly walking down the stairs, as if pondering something. She sits down next to me and says, “You mean, like this?” She turns my head towards hers and gives me a kiss. She obviously learns quickly, since this kiss has much more substance to it than her earlier effort. Her tongue, which was mostly limp when I kissed her, is now circling around my mouth, interacting with my tongue, and her lips are showing life as they move over mine. I’m also keenly aware of her hand on my leg supporting her. I’m starting to appreciate her in a new light.
After a few moments, I break off the kiss. “You don’t know what you’re getting into,” I tell her, fearing that this might get out of control.
“Then show me.”
“I can’t do that,” I say.
“I know you’ve been looking at me,” Sarah replies. Now I know that those views I was getting earlier from her were intentional. “Teach me what games big boys and girls play together.”
At this point, I know I can’t talk her out of it. Instead, I try a different approach. I lean towards her and start kissing her again. My hand immediately moves up her side and cups her budding breast. I notice that she doesn’t wear a bra, and that the nipple crowning her small mound becomes hard under my touch.
I was expecting her to jump away, but instead she pushed her body towards mine more. Her hand was moving up and down my leg, heading towards my crotch. I could feel my member reacting.
I decided to push her to see how far she really wanted to go. I leaned her back on the sofa and moved over her, not breaking our kiss. I slowly lifted up her shirt, exposing her. She didn’t give any resistance. My hands started moving over her bare tits. Her nipples were being throbbed as they crossed the gaps in my fingers. She was squirming a little in pleasure and I could feel her breath getting ragged during our kiss.
I broke the kiss and moved my mouth down towards her chest. I first licked the flat area between her tits, and then slowly worked my way across and around the mounds. I could see that there was definitely some development there, even if she was only an ‘A’ cup at this point. As my lips approached her pointed, pink nipples, I could hear Sarah’s breath quickening. When I started circling the tip with my tongue, she let out a loud moan and arched her back up towards me. I continued like this for a while, letting the new feelings of pleasure course through her.
Then I lifted by head back up and said to her, “It’s your turn to make me feel good now.” I expected this is where she would balk and end our little game, but instead she sat back up and moved her hands towards my crotch. She started rubbing over my jeans and felt my cock.
“Oh, you mean here?” she said coyly. “It feels very squished in there. Isn’t it uncomfortable?”
“It only gets hard during these games; the rest of the time it’s more flexible. When it gets hard, the best thing to do is to let it out.”
She took the hint, moving her hands to the snap of my jeans and then pulling them down my legs. My erection jutted prominently up into the air. At first, Sarah just looked at it, but then she reached out and put her hand on it. She started squeezing it similar to how you would milk a cow. I put my hand over hers and showed her how to slide it up and down instead. The touch of her petite hand felt very nice.
While she was doing this, I took my hand and starting stroking her thighs. My hand drifted further up her leg with each pass, sliding up under her skirt. It soon reached the edge of her panties and I could tell that my touch was having an effect on her. When my finger ran along her cleft, feeling the moisture that was soaking through her panties, I could feel her breath catch again and the motion of her hand became irregular. As I continued stroking with that finger, I moved the other hand underneath her skirt as well.
In a quick motion, I hooked my hands underneath her panties and pulled them partway down her legs. My finger immediately returned to her pussy and started stroking it again before she had much of a chance to object. There was a surprised look in her face as I exposed her privates, but that was quickly replaced by a look of pleasure as my finger stokes the fires of her pussy even hotter.
At this point, I had lost most of my reasoning and just wanted a chance for my cock to deflower this innocent girl sitting here. As she was lost in the waves of pleasure, I asked her, “Do you know what that cock you’re holding is for?”
I leaned her back on the sofa again and moved over her. I slid her panties off her feet and then moved between her legs. My hand never left her pussy and was still churning away. As I moved my body down to her, I could see a look of confusion or uncertainty in her eyes.
“I’m not sure…” she stammered as I lay down on her. Her shirt was bunched up above her tits again with her skirt flipped up to her waist, exposing all of her private areas to me.
“You were the one that wanted to know what games boys and girls play.” I knew I should probably stop at this point, but the compulsion was too much. I moved my cock towards her opening and guided it in place with my hand.
“But…” Sarah started to say as I flexed my hips, pushing the tip of my cock into her virgin pussy. “Oh…” she gasped at the contact.
“This might sting a little,” I warned her. I moved just a little bit, enough to get her wetness on the end of my cock and then pushed in hard.
She screamed out as my cock penetrated deep into her. I could feel her membrane tearing as I pushed all of the way in. Once buried deep inside her, I paused to let her get used to my size. Then I pulled all of the way out of her and slammed my cock back inside.
The feeling felt very tight and snug. She was definitely wet all the way through. I looked down and could see a little trickle of blood leaking out the edge of her pussy and staining my cock as I worked it in and out of her. Looking back at her face, I could see tears on her cheeks. However, the pain was fading from her face, replaced with look of pleasure. She started moving instinctively to match my movements.
All of this was too much for me as I surged inside her once more and held there as my cock let forth a burst of juice deep in her pussy. The first burst was followed by another and another as I emptied myself completely in her. Sarah obviously knew something was happening from the way my rhythm changed, but I don’t think she understood what was going on. My movements slowed and I came to rest on top of her, with my still pulsing cock buried deep inside her. As I lay there, Sarah smiled up at me.
Now that I had calmed down, I realized several things. Most college girls are on the pill (or at least the ones that are having sex), but she probably isn’t. Well, what are the odds that it’ll happen this one time?
I also felt a little bad that she didn’t get off the way I did. Maybe there will be another chance to show her.
But my biggest worry is what Sarah would tell her parents. “Did you like our little game?” I asked.
“Yes,” she said between gasps. “It didn’t seem the same as what the other girls talk about.”
“Anytime you want to play some more, just let me know. But you can’t tell anyone else about it. It’s our little secret.” Hopefully I can show her more next time and that will keep her parents off our back.
As I got up, I looked at the pool of blood and semen that was dripping out of her and onto the skirt. “Let’s get you cleaned up and off to bed,” I said.
She hopped up and gave me a squeeze, before bounding up the stairs. “You’re the best sitter I’ve ever had.”
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