Adventures in Babysitting

He's going to be a heart-breaker in high school. I imagine he's at the age before the initial attempts at sex but he's already sought and found his father's porn collection and masturbates to its memories religiously. He probably jerks off the the cobbled together moments of sexuality which we stop noticing when we start fucking.

I have noticed him noticing me, and I like that. He probably looks at his friends' moms and sisters, imagining them in states of undress, trying to figure out the difference between who would shave and who wouldn't, and what that even means. I have been his babysitter for a few months now and have loved watching the crest of his discovery that he does, just like everyone else, want to fuck everything all the time.

When I walk into the room, he is startled, and I can tell the outline of a half hard cock under his jeans. He blushes blood red and moves his hand. Whatever he was watching on TV, it had inspired him to stroke himself through his pants. I can't help but smile at him, and I know he knows that I know.

"Good show?" I finally ask as I sit down, far enough away so he can look at me, watch my legs stretch onto the coffee table, take in butter pecan thighs and sloping calves, looking up to creases of cleavage and hills of collar bones that I offer up to his eye but not his hands.

He catches his breath a little. "Yep."

"What is it?" I stretch back just slightly. He mumbles something that I'm not familiar with and tries to focus on the television, his initial inspiration. "The girls on there are cute."

He smiles, blushing a little more, and then calming down. The bulge in his pants has only gotten bigger and he shifts his jeans to hide it and relieve it at the same time. I love this moment. He has stopped being his talkative self and I can't tell if he's trying to ignore me, but I can tell he's failing. Every time I shift, yawn, his eyes dart into the corners but his head remains rigid, as if stealing glances makes it ok. I ask him questions and his answers begin falling into single answers.

"So... HAVE you kissed a girl before?" 

"Yeah, of course." His bravado is adorable and I am more certain than ever that he has yet to do more than flirt with sex.

"Oh yeah? Second base?" He smiles and laughs a little, trying to hide his youth behind pride. "Third?" He shakes his head.

"No... nothing like that. I had a girlfriend for a while and she let me put my hands under her shirt a couple of times."

I smiled and winked at him. "Way to go, stud. Did you like it?"

"Yeah."

He has gotten harder and is struggling more and more to get comfortable, thinking I don't know he's aching to stroke himself. He tells me a little bit about her, his voice getting steadier as he describes her hair and penchant for bracelets.

"And do you jerk off?" He finally blushes and looks down, away from me. "It's ok if you do, everyone does. everyone should, at least... I do."

This is almost too much for him and I see the mental image reach him. "You... you do?"

"Yeah, absolutely. I love to." His eyes go a little wide. "You should definitely do it. It's really good for you to learn what you like."

"Oh... I... yeah." I giggle a little, biting my bottom lip, thinking about how struggling against his jeans.

"Yeah... you're hard right now, aren't you?" I narrow my eyes on his, making sure he stays with me, the TV becoming a distance flicker. He nods, and I refuse to give him back his gaze. I own it, just like I own the swell of blood to his cock.

I lower and soften my voice but not my eyes. He's mine right now but I want him to feel enveloped. "You want to stroke it right now, huh?" He nods again, and his hand is trembling. "Take it out."

He stares at me, unsure of what I said. I nod. He heard right.

I hope he has a cock like his dad, which I still stroke through jeans when he drives me home. Sometimes he'll pull off to the side and let me suck it for a while before he feels bad and stops right before he cums.

He pulls out his rigid cock, his hand wrapped around it. It's sweet to watch him both thrilled to be touching it and embarrassed by his own pleasure.

"Stroke it for me." He hasn't looked down or away. He simply nods and begins working his cock up and down the way he has taught himself. His breath is beginning to speed up as he squeezes.

"Slow. Don't cum yet." He nods, watching intently still, still held by my detached gaze. He is too nervous to go fast, afraid he'll cum too fast. "Pull down your jeans a little, it'll be more comfortable." He nods again, shifting to pull down his pants and boxers - blue and plaid just like his father's - and fully expose his swollen cock, still unable to speak.

"Do you ever squeeze your balls?" He shakes his head and I motion a little with my head. "Take you other hand and squeeze them just a little."

He shudders with the squeeze. It is a delicious little shudder through his shoulders and chest and he squeezes harder on his cock as he does it. "Slow. Just relax. Keep stroking, softer than that."

He takes direction so, so well, but I can tell he's struggling to hold on as his hand moves up and down, his other hand between his legs, stroking his balls almost investigatively. New buttons to push he has never known in this way.

"Slowly." He nods. I smile at him and he is being diligent. Little beads of sweat appear on his forehead as he struggles not to cum. He has been so good about not letting his eyes wander that I want to reward him. "How you ever seen between a girl's legs before?"

He shakes his head as his eyes go wide. I smile and shift on the couch, lifting one bent leg onto the cushion. I let him stare at the patch of fabric that hides what is still the world's greatest mystery to him. I slowly reach down, pulling aside the purple fabric, letting him see in person, a shaved and wet cunt.

He stares, his hand moving faster, and with a jolt, he cums, spraying his load over his hand and jeans, wave after wave making his face tighten and eliciting the smallest of whimpers. His eyes squeeze shut as he buckles forward a little.

His breath comes back slowly. I let him come back down to the world as I shift back to sitting on the couch as I was. "Go clean up and change - do you want ice cream?" He nods, still not using words.

I get up from the couch and let him open his eyes alone. When he comes back in his pajamas there are two bowls of ice cream on the coffee table. Butter pecan.