Babysitting two teenage boys and having to teach them about how to wank…
When I started babysitting in this house, they told me the twins were a menace. Absolutely uncontrollable. I have them a few days a week in the evening hours, both their parents having a lot of social engagement, and I have to make them dinner and make sure they go to bed early. Nothing too complicated, but apparently no babysitter has lasted long before me.
I’m young myself, only 18, but I have younger brothers the same age as these kids, 14, and I know how to put boys in their place. I was bracing for the worst.
But actually, up to this point, it hasn’t been too hard.
I found out early on that being a girl with decent sized breasts really helps in having them listening to me. Especially when I don’t wear a bra.
“It’s time for bed” I say, getting close enough for my nipples to be clearly visible under my shirt.
“Yes miss” they say politely, while staring at me in awe, and off they go to bed as I asked. Probably jerking off in their beds, but who cares?
It’s been a month and honestly the hardest thing has been having them stop staring at my breasts. But I kinda like it. I mean, what’s wrong with looking?
I have grown quite fond of the boys to be honest. They are polite and nice, and they love each other very much. They like me, I think, and they really started to respect me and listen to me, as with an older sister.
Today though, I had my first real challenge when I found them in their father’s office watching porn, and I knew it was time for a hard conversation. I sent them to bed, and then went to their room to talk to them before sleep.
“I wanted to talk to you boys about what you were watching” I say, sitting on the bed in between them.
“We’re sorry, miss” says the bolder of the two “we just wanted to see what sex looks like”.
“Yeah” follows his brother “like…research!”
I’m about to laugh. Research? But, of course, they are young teens. They are going to…research, one way or the other. But I’m aware of the issue with porn, how it affects young minds and boys in particular, giving them unhealthy expectations that translate into bedroom problems.
“You need to understand porn isn’t the same as reality” I tell them “People don’t really look, or act, like this in real life. I want you to know this because otherwise you’ll have issues with real girls…”
“What do you mean, miss? That girl looked like you” one of the twins says.
While flattered, I have to laugh “The video you were watching has an actress with really big fake boobs. They don’t look like that in real life”.
“So how do they look?” asks his brother, all ears.
“Smaller, and more squishy, and less… Up” I try to explain, I admit, very poorly.
A pause.
“Can we just see your boobs?” the request is almost a unison.
“No, you can’t!” I exclaim, taken aback by the boldness they are showing.
“But you said we needed to know how they look in real life!”
“I didn’t really say that…” I try to clarify.
“Please, miss…” they beg, doing the big eyes thing that always works when they ask for seconds at dinner.
Oh, well. Who cares? It’s just boobs. Better me than more porn, right? Or better me willingly than being spied over in the shower.
The boys look in silence, waiting politely for me to make a decision
“Ok. You can look” I say finally.
“Thank you, miss!” They reply in unison.
I lift my t-shirt and my boobs bounce free in the air. No bra.
I don’t have massive breasts, but they are…good. Big and perky, my nipples pink.
I must say, I really enjoy their reaction. They look stunned, as if they rested their eyes on the holy grail.
“They are just boobs, boys!” I chuckle.
They giggle at the word boobs, but I see them relaxing at the joke.
They start to really look, moving their heads to see different angles of them, even upside down. I try not to laugh.
The braver twin gets really close to the front of them. I can feel his breath on my skin, and my nipples get hard under his gaze. Fuck.
“Those are the nipples” I say, to diffuse the tension “They get hard in the cold, or with stimulation, or from arousal” when did this become a sex ed class?
“Can I… Touch them?” the bravest of the brothers, the one closer to them, asks “Please?” he adds right away, remembering his manners.
“Me too!” Says the other one, afraid of being left out.
Their hands are already lifted but kept at a respectful distance, waiting for the green light from me.
“I’m not sure…” I mean, I’m trying to keep these two off porn, not giving them material. But also… it’s not really a big deal. The only issue is: will they take advantage of my kindness?
“Please miss, just to see how they feel?” They ask in their polite boys’ voices “you said they are squishy… How are we supposed to know?”
“Ok, ok… but just a moment!”
“Yes, miss!”
“Thank you, miss!”
They each take one, sharing like good brothers, as always.
They caress tentatively. One takes a light squeeze. The other goes for the nipple, flicking it between his fingers. Then he pinches, hard.
“Ouch! That hurt!” I scold him.
At my exclamation, both boys retract their hands instantly.
“I’m so sorry miss, I didn’t know…” Says the one who mistreated my nipple. The other one is looking at him with the ‘look at what you’ve done’ face I usually reserve for them.
This is good. It’s a way to teach them something important “A woman’s body isn’t a toy” I tell them, seriously “You need to start with a light touch, and build up from there, based on her reaction”.
“Yes miss, I’m so sorry” the boy says, unable to look me in the eye. I see he’s almost on the verge of tears.
“It’s ok, you’re learning. You didn’t really hurt me.” I reassure him “Try again. Lightly, this time”.
“Thank you miss!”
They both immediately reposition their hands, squeezing and flicking and gently pulling. They got the note, and they check my reactions after trying something new. I nod politely and encouragingly, as they start pinching lightly, all the way up to a tight squeeze that almost makes me moan. Based on my very limited experience, I must say they are really good.
I’ve been fondled like this before, by a few older men (mostly family members) as well as my classmates in school, but this is different, it’s more respectful, and I’m really liking it.
My nipples are really hard now, and the two are definitely pleased with their work, their breaths more labored than when we started.
“Can I please lick them?” One asks “Just for a moment” adds the other.
I get back to reality. We went too far.
“No, boys, enough” I make a move to lower my shirt again, but they start begging.
“Please miss! We’ll go nice and slow, we need to learn before we go with a real girl!”
“We’ll lick them for just one minute”
“Promise, miss!”
Damn, they are cute when they beg “Ok, ok, but just one minute” I say with a defeated sigh.
Their mouths are on me as soon as I lower my arms.
They are squeezing them with their hands as my nipples are in their mouths, and they start sucking them lightly, as promised.
I let out a little gasp before being able to stop myself.
“Is this good, miss?” they ask, looking at me.
I nod, unable to respond, and they both get back to their respective boob.
I look as they suck at my nipples at different rhythms. They are panting a bit and they seem more and more excited as they squeeze harder, looking at me to check my reactions.
It’s driving me crazy. I’m struggling not to moan.
One starts to bite me lightly and I realize I’m getting excited from two little boys nursing on me, my pussy probably already wet.
“Enough!” I say aloud, standing up. The boys are red faced and hot. I see both have a hand on their crotch. Their hard dicks are visible under their pajamas.
Damn.
“Ok, now you have tried… That. You’re welcome” I say, with a tone of finality that I hope will conclude the begging.
“ But miss, we can’t sleep now!”
“No, miss we can’t!”
“We’re too hard to sleep!”
“Well, just… Wank it out, boys” I tell them. I don’t care what they do on their own.
“What’s that?”
I look at them, trying to understand if they are joking, but their faces just show confusion and curiosity.
“You don’t know what wanking means?” I ask, incredulous.
“No, miss” they shake their heads as one.
“You watch porn, that must make your dicks go hard! What do you do then?”
We go pee and after a while it goes down.”
“But we never got this hard, miss!”
Oh. Damn.
Now I feel bad. It’s my fault, I made them horny and now they will be up all night.
Oh no, what will I tell their parents?
I need to resolve this now.
I sit again between them, smiling sweetly.
“Ok, take them out” I tell them, as if the idea was a huge chore for me. Which, if I’m to be honest, isn’t. I’m horny myself, and maybe my wet pussy is influencing my decision of wanting to see their hard ons.
They lower their pants to reveal two identical medium sized very hard cocks. Impressive, thinking they still have to grow to their full potential.
They are holding them at the base, pointing them around as if they were joysticks.
“Ok” I start instructing them “move them like that, but up and down, moving the skin”.
Again, they look at me in confusion. Damn I’m bad at explaining this, but to be fair, I’ve never done it myself!
Maybe they’re visual learners. I hold my hand in a semi open fist and do the motion in the air “Like this” I say.
They try clumsily on their own dicks with less than perfect results.
“Ouch!”
“It hurts!”
Hurts? I realize that maybe they need some lubrication.
“Do you have some hand cream?” I look around, expecting to find cream I’ve never seen before.
They both shake their heads. Of course.
I lick the palm off my hand, leaving a steak of saliva on it.
“Do this”
They look disgusted.
“Oh come on!” I say “just try!”
They do it, but they aren’t convinced at all “It’s not enough!” one boy says, obstinately.
I’m getting frustrated “Yes, it is! Look!” Before thinking, I grab his cock and stroke it. I have quite a bit of experience in this already. I touched my cousin a few times, playing doctor, and some grownups asked me to do it when I was little, and more recently I’ve serviced a few boys at school… they were all more than content.
The boy looks shocked for a second and then gives a moan “Ooohhhhhh miss!”.
“Miss, miss it’s not fair, me too!” cries the other, offering his hard dick.
There’s no way I’ll get away with stopping now.
I lick my other palm and start jerking off the second twin.
“Ooohhhhhh, miss!” he also exclaims.
Their dicks are hard under my hand and I’m enjoying the feeling of touching them. This is so wrong… I’m so horny and I’m starting to really want… no. I need to finish this. Now.
“Suck on my boobs, boys” I say, hoping that will make them cum faster.
Their mouths are on my nipples right away, sucking me as if they were babies hungry for their milk.
“Good boys, suck me hard, yes” I pant, hoping they won’t notice my excitement.
I keep stroking them, trying to make them cum before I completely lose my mind and fuck one of these boys.
I close my eyes, lost in the moment, listening to the sucking noises and the rhythmic pumping of my hands on their young cocks.
I feel their hands fondling my boobs, caressing my skin, getting dangerously close to my yoga pants, knowing there would be no resistance if they were to get to my leaking pussy…
“Miss… Miss… I need to pee” one says suddenly.
“Me too, miss!” The other follows.
That’s exactly what I was waiting for: “You’re not going to pee. Just let go boys, cum for me! Cum for miss!”
“Aaaaahhhhhhhh” they almost scream in unison.
They start to shoot. As I’m pointing them both towards me, they both hit my boobs, my pants, and even my face.
“Yes!” I find myself saying, as their orgasms come to an end.
“Thank you, miss”they say, tired.
But I’m not satisfied. At this point, my sexual frustration is needing an outlet. I want these boys to pay for my current discomfort.
I keep wanking them, my hands steady on both cocks, using cum as lubricant, focussing on the tip of their still hard dicks.
“Miss, it hurts”.
“Please miss, stop” they beg. I don’t care.
“You wanted me to make you cum? I’m going to make you cum again, I don’t want to hear a peep”I say, severe.
They are twitching under my hands, but they both are accepting the sexual torture I’m putting them through.
“AAAAHHHH!”
“IT HUUUURTSSS!” They protest in vain.
“Shut up, boys. Cum again for me. Do as you’re told”.
A few seconds later, it happens. “I’M CUMMING, MISS” shouts one. “AAAAAAHHHHHHHHHHHHRRRHGGGGGHHHHHH” is all the other can say as he finally releases his second orgasm.
What a show! If I thought they cummed hard before, now they almost shower me. This looks more like squirting than a normal ejaculation.
I’m full of it. My hair, face, and tits are completely ruined.
I stop the wanking, smiling at them.
“Good boys. Now say thank you and go to sleep” I say, standing up and leaving the two boys completely stunned and depleted.
“Thank you, miss”
“Goodnight, miss’
“Goodnight, boys” I switch off the light before leaving the room, knowing well they will probably be asleep in a minute.
As for me, I have to go in the bathroom and finger myself furiously until I get to orgasm, licking the cum that’s still on my face.
“Everything ok?” ask their parents when they come back a few hours later, finding me reading on the couch, fresh clothes on.
“Yes, everything is fine” I respond “they are sleeping like little angels”.
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