An Awkward Chat
I tremble as I sit, naked, hands clasped over my crotch, at the kitchen table across from my little sister Janine and her 2 friends, Yuna and Marie.
My older sister, Heather, paces behind them, glowering.
I shift, making the hard wood of the chair creek beneath me.
The hard wood beneath my hands also trembles.
“What the hell were you doing to them?!” Heather scolds.
“Nothing!” I yell.
Janine, Yuna and Marie giggle conspiratorially.
“That’s not what I saw, and thats not what they said!” Heather continues her interrogation/accusation.
Rewind.
My name is Shylo.
I’m a 13 year old boy, and I live with my 2 step sisters Janine and Heather.
Janine is 11 and Heather is 15.
As opposed to their flowing, radiant, coppery red hair, my hair is blonde, cut into a trendy ‘bowl’ style.
I find myself in this current situation because of the situation that preceded it.
I was supposed to be watching Janine and her two 10 year old friends, Yuna and Marie, after I got home from soccer.
(They’re all double digits. They can take care of themselves, right?)
I made sure they had snacks and were entertained with a tv show, then, headed to the bathroom to shower.
As the warm water and scrubbing eased my muscles and washed away the grass of practice, a thought that came to me in the shower regularly, made it’s presence known-
I shared this bathroom with my step sisters.
Heather stands right where I stand now, naked.
I picture her long red hair, weighed down by the running water and shampoo, flowing down her porcelain back.
I picture the suds streaming down her spine, rolling over her supple hips and into her butt-crack.
I picture her turning around.
In my mind, her breasts are perky, with little pink nipples and she has a small patch of copper pubic hair.
My own hands find their way to my penis.
I scrub my sparce pubic hair and work my hands along the shaft of my penis and balls.
I’m glad I can shower at home.
I already get made fun of during practice.
Even when I wear briefs, a good portion of my penis flops out of the leg hole, pinned to my thigh by the elastic.
It’s not always obvious, but my teammates HAVE noticed.
Fortunately, the teasing is relegated to light warnings about possible wardrobe malfunctions.
My thoughts still on Heather,
I keep scrubbing and soon, my penis is fully erect!
I finish washing and grab my towel.
After drying off I hang the towel up and head to my room.
The incident:
I can hear the tv in the livingroom.
Janine, Yuna and Marie are still watching cartoons.
I walk quickly and quietly to my bedroom.
My penis is still rock hard and begging for release!
I kick the door closed behind me.
I lay on my bed and proceed to grab my penis and begin tugging.
My thoughts again drift to Heather.
I picture her in front of me, naked.
I keep jerking.
Usually, I can cum in seconds thinking about my older step-sister.
But right now, I need something more!
A realization.
Heather isn’t home right now.
My thoughts and judgement are clouded by hormones and a need for release.
I slip out of my room and walk quietly half-way down the hall to Heather’s room.
The thrill of sneaking naked down the hall when 3 little girls are just around the corner is something new.
I quietly open Heather’s door and slip inside her room.
My eyes adjust to the dimness, lit only by the natural daylight coming in through the blinds.
I make a b-line to her dresser.
It’s as though I’m being guided by my throbbing penis!
I open the center top drawer and feel my penis twitch as I behold it’s contents.
There, folded tightly and lined in perfect simetrical order are her panties!
My trembling hand hovers over them as I make my selection.
A pale, pink, non-patterned pair catches my eye.
I pluck them from the drawer.
The trifolded garment unfurls in my fingers as I lift them up, examining them.
The simple, solid cotton garment offers even coverage, both front and back.
I picture them ON Heather’s slender form.
My penis twitches.
I press them to my mouth and nose.
Inhaling, I smell the sweet scent of lavender detergent.
I shut the drawer.
I clutch the panties to my chest and sneak back to my room.
I glance back at the livingroom, still hearing the sound from the tv.
Clear.
As I make my way down the hall, I picture Heather, naked, keeping my penis fully erect.
I enter my room, kicking the door closed (I thought) and lay on my bed.
I grip my penis and begin tugging, resting the panties over my face and picturing Heather naked!
I find my rhythm and keep tugging.
I don’t have any concept of ‘oral sex’ yet, but my tongue flits out, gently flicking the crotch of Heather’s panties.
I’m breathing heavy now, getting fully immersed in my fantasies.
I look down at my penis.
Fully erect, it points to the ceiling, 2 inches of shaft exposed on either end of my fist.
I pump my hand, rhythmically, fully aware of the ‘end result’ I strive for.
I inhale deeply.
Though the panties smell of detergent, I picture it being not too dissimilar from Heather’s actual scent.
I adjust the panties to cover my face, inhaling deeply.
Suddenly, the door swings open.
There, stands Janine, immediately flanked by Yuna and Marie.
I freeze.
After a moment of silence, I realize the position I’m in.
First, I rip the panties from my face and toss them away.
Next, I try to cover my crotch with my hands.
Too late.
I sit up.
“Guys! Get out!” I yelp.
Janine abruptly turns, covering her face.
Yuna and Marie do no such thing.
The two 10 year olds giggle and point.
“Oh my gosh!” Yuna yelps.
“Wow! He’s naked!” Marie shivers, hugging herself.
I stand, trying to be authoritative.
I point, moving one hand away from my privates to gesture for them to leave.
In my flustered state, I fail to remember the size of my own anatomy.
My remaining hand is only covering the lower portion of my penis, leaving the top half of shaft, head and lower portion of my balls completely exposed.
Yuna practically faints, momentarily, swaying on her feet.
I move forward, hoping my posture and anger scare the girls away.
Marie giggles.
Janine turns back around as I move towards them.
She points at my hand on my crotch.
“Shy! We can still see it! Oh my gosh!” She yelps.
I look down, already knowing what I’ll see.
Sure enough, 1/4th of my erect penis looks back up at me, exposed over the top of my hand.
I cover with my pointing hand, completely shielding myself.
Yuna and Marie begin pointing as well.
“Guys! Get out!” I yell.
Janine is doing her best not to look, instead looking back and forth between her friends and anywhere else.
Janine freezes as her eyes lock onto a crumpled garment on the floor.
She hops over, stepping around her friends and picks Heather’s panties up.
She unfurls them.
Our eyes meet as she recognizes the garment.
“Shy! Why do you have Heather’s panties?!” She gasps.
Yuna looks at them, then back at me.
“Ew! He had them on his face!” She scrunches her face in a disgusted grin.
Marie giggles as, she too, contorts her face in disgusted amuzement.
“Give those back!” I yelp, stepping forward and reaching out.
This partially uncovers my penis and balls again.
Janine points.
“Shy! We can still see it!” She yells.
I cover again, though, at this point, all three girls have seen everything.
My modesty is forever lost to my 11 year old step sister and her 10 year old friends.
“Janine! Give me those panties and get out!” I demand.
The girls share a quick, silent look, then grin.
Yuna takes the panties and shakes them in front of her.
“Come get ‘em!” She teases before bolting out the door.
Janine and Marie burst into excited giggles as they immediately follow Yuna down the hall.
I’m momentarily frozen by the turn in events, but I quickly return to my senses.
My only thought is that I need to retrieve Heather’s panties at all costs!
I run out of my room, giving chase.
I hear the frantic giggling from the livingroom.
I cover with my hands again as I round the corner to see Janine on the couch, grinning with her hands beneath her legs.
Yuna and Marie sit just like her on the chairs in the opposite corners of the room.
“Give me those panties! I need to put them back!” I demand.
“You’ll have to find them! Hehehe!” Janine teases.
“No! Where are they?!” I again demand.
The girls just shake their heads, giggling.
“Maybe they’re ‘underneath’ something.” Janine teases.
“Maybe they’re ‘underneath’ some ONE.” Yuna adds.
“I bet you really want to get to the ‘bottom’ of this, huh?” Marie grins, rocking back and forth on her hands.
No!
One of them is sitting on them?!
I don’t have time for this!
I go to Janine first.
I uncover as I crouch and grab her ankles.
She gasps as my erect penis bobs free!
I try just pulling her off the couch by her legs, but she’s somehow gripping the attached cushion with more strength than her slight frame should be capable of!
I place my hands on her shoulders trying to pull her forward.
“Shy! Whoa!” She yelps.
I freeze, immediately seeing my mistake.
My erect penis is now only inches from her face!
“Hehehehe!” Yuna giggles and shifts in her chair.
Does SHE have them?!
I abandon Janine, accepting that she just got another look at my genitals, this time, up close!
I move swiftly to Yuna.
She tucks her hands beneath her butt.
I grab her shoulders and try to pull her forward.
As with Janine, this puts my erect penis in dangerously close proximity to her face!
“Ew! Hehehe! Shy! Your weiner’s SO BIG!” She giggles and squirms as I try and see behind and beneath her.
Yuna seems to have the ability to increase her weight or something, as I am unable to move her enough to determine whether or not she has Heather’s panties.
Out of the corner of my eye, I see Marie pull her legs to her chest as she sits on the other chair.
She must have them!
I abandon Yuna, walking with as much menace as I can muster in this current situation, hoping she’ll surrender Heather’s panties and this game of keep away can end.
Marie tucks herself into a tight ball as I approach.
Her eyes go wide and I see her pupils shift side to side as they track the subtle sway of my stiff penis as I walk towards her.
“Give ‘em.” I say flatly, putting as much authority in my voice as possible.
In utter defiance, Marie sticks out her tongue and cackles.
I grab her wrists and try to pry her arms from around her knees as ‘gently’ as possible.
I manage to get her hands on her knees, which remain tucked to her chest.
I pull, spreading her legs apart, trying to get her to move so I can get the garment I’m certain rests beneath her.
In all my hurried, flustered movement and with the girls’ highpitched giggling, I failed to hear the front door open and close.
I have my hands on Marie’s knees, trying to move her enough to get Heather’s panties back when I hear it.
“SHYLO!” Heather screams.
Everyone freezes.
“What the hell do you think you are you doing?!! Get off of her!” Heather shoots forward.
In the instant it takes her to reach us, I realize the compromising position I’m in and how it must look to Heather.
I lift my hands away from Marie’s knees and hold them up as I stand straight.
My erect penis juts forward, stopping inches from Marie’s face!
Marie grins wickedly.
“Ew! Shy! Get your big weiner out of my face!”
With that, Marie gently slaps my erect penis!
The contact of her soft fingers is electric!
She and I both gasp.
Heather grabs my arm and pulls me to the center of the room.
She has a death grip on my arm, and I can’t escape.
I hold my free hand to my privates, trying to shield as much as I can, but the damage is done.
On top of that, the excitement has me dangerously close to cumming!
The reality of my situation sinks in.
Heather is screaming at me with so much fury, her words feel like physical blows.
She’s crushing my arm as she drags me to the kitchen.
She kicks one of the chairs around the dinner table out and pushes me down.
“Ow! Hey!” I yelp.
I adjust my hands to cover my erect penis completely, letting my balls fall between my legs as I adjust to hide them as well.
“You sit RIGHT there! Don’t move!” Heather’s voice is cold and authoritative.
Her usually milky skin is as red as her hair!
Heather turns and exits the kitchen, heading back to the livingroom.
I could hear Heather and the girls talking.
A few hurried, muffled statements from all the girls in rapid, layered succession that I couldn’t make out.
“WHAT?!” Heather bellowed.
She practically flew in from the livingroom to confront me.
I’ve never seen my older sister’s pale skin so red.
Her eyes blazed.
The girls slipped in behind her, grinning and holding back laughter.
“Sit, all of you.” She says, stearnly.
Back to the now:
“What the hell were you doing to them?!” Heather scolds.
“Nothing!” I yell.
Janine, Yuna and Marie giggle conspiratorially, sitting at the table accross from me.
“That’s not what I saw, and that’s NOT what they said!” Heather continues her interrogation/accusation.
“What THEY said?!” I looked at the girls, a sinking dread setting in.
All 3 were smirking, but then quickly shifted to nervousness as Heather looked at them.
“He took your panties and then said he wanted OUR panties!” Janine shuttered.
“Liar!” I yell.
“It’s true! See?” Janine pulled Heather’s panties from beneath her shirt.
She tossed them on the table.
Heather snatched up her undies and clutched them to her chest!
“He said if we didn’t give him ours, he would hit us with his thingy!” Yuna pointed.
I felt sick.
“I DID NOT!” I screamed.
“DID TOO!” The girls yelled back.
We screamed back and forth as the noise rose to a cacophonous roar before Heather clapped and yelled “Enough!”
She pointed at me.
“SHY! UP! NOW!” She gestured for me to stand.
Her tone terrified me to my core!
“NOW!” Her green eyes flared.
I scooted back from the table and rose, doing my best to hide my erect penis.
Heather’s eyes widened as she looked at my hands.
Though 2 years older than me, and presumably much more ‘knowledgable’, I was unaware that Heather had only a ‘baseline’ knowledge of male anatomy.
“Hands on your head, Shy. Now!” She demanded.
I looked at the girls.
“Heather! No! They’ve seen enough!” I beg.
“So, you admit to chasing them around with your dick?!” Heather gasps.
The girls giggle at Heather’s ‘curse’.
“What?! No! I was just trying to get your panties back!” I yelped.
“Yeah! That’s why he said he was going to hit us with his thingy!” Yuna pointed.
“Yeah! His ‘dick’!” Janine smirked, wickedly.
Heather fumed.
“SHYLO! HANDS! HEAD! NOW!” She pointed.
Sitting there, I held my hands over my penis, feeling it twitching, dangerously close to going off thanks to the situation!
I looked at the girls.
Janine smirked wickedly.
Yuna was squirming, biting her lip.
Marie was giddy!
Heather lunged, kicking with her foot to swing my chair out.
She grabbed my arm and pulled me to my feet, her furious strength making it seem effortless.
“Heather! Please!” I begged as she pulled on my arms.
I squirmed, already feeling the hot sting building in my penis.
Heather had seen it, but not to the extent the other girls had!
I wanted to keep it that way!
“Uh uh! You had no problem showing these LITTLE GIRLS your dick before, so why hide it now?!” She scolded.
She tucked her panties into her waistband and pulled on my wrists.
The girls scooted around to get a better look.
Heather momentarily relented, causing me to loosen my grip for a moment.
Then, with frightening speed, Heather shoved her hands down my arms, gripping my penis with both hands!
“Ah!” We both yelped.
“Wha-?! Shy! OH MY GOD!” Heather yelps.
Her eyes dart down to look at my penis in her hands.
BOTH hands!
“Heather! Pl-!” I start but Heather squeezes.
Her grip is frighteningly firm, but her hands are undeniably soft.
I look at her wide, green eyes as they dart between mine and my erect penis in her hands.
“Uhn!” I moan as she squeezes.
“Please! Heather! That’s too much!” I beg.
Heather narrows her eyes.
“Enough!”
Still holding my erect penis in one hand, she pulls her panties from her waistband again.
After balling them up in her fist, she squeezes my penis!
“Ah!” I gasp.
Heather then shoves the balled up garment into my mouth.
The taste is chemically floral and not as pleasant as the smell had been.
“Now.” Heather steps to the side, still gripping my throbbing penis.
She finally takes a moment to examine my genitals.
“Heather! You’re touching his weiner!” Janine gasps.
“Yes. I am.” Heather squeezes.
“Mmmm!” I moan, her panties in my mouth muffling my voice.
The chat:
“Shy. We need to have a chat about what you were doing to Janine and her friends.” Heather says, coldly.
“MfmmmMfmph!” I try to speak, but the panties muffle everything!
Heather squeezes.
My body trembles!
Her hand is petite and soft, but her grip is forcefully strong!
Heather looks at the girls.
“Janine. Yuna. Marie. This might be awkward, but I need you to tell me EXACTLY what happened.”
“Mmumuhmmuhmumph!” I frantically mumble.
Heather squeezes my penis again!
I tremble and stop mumbling.
This is dangerous!
My beautiful older step sister has no idea how close I am!
I can’t lose my last bit of dignity here!
Not in front of these girls!
My eyes meet Janine’s, pleading.
I see a glint of something, and then, the slightest smirk.
“We were watching tv.” Janine started.
“Just cartoons.” Yuna added.
“Then we got hungry.” Marie continued.
“So we went to get Shylo to make us something.” Yuna nodded.
“We went to his room, and he was-.” Janine winces, still playing innocent.
“He had your panties on his face! And he was-“ Marie blushes, deep red and grins.
“He was playing with his wiener!” Janine points.
Heather’s emerald eyes burn bright and her lips curl in disgust.
Still with one hand on my penis, she pinches the bit of wadded panties sticking out of my mouth and shakes them, threatening to shove them deeper!
“When he saw us, he threw your panties at us and got up!” Yuna shivered.
“He was real mad and scary!” Marie cowered.
“But don’t worry, Heather. I got your panties back from him! That’s when we ran!” Janine nodded. “We kept your panties safe, while he chased us around!”
“Yeah! And he kept trying to hit us with his big wiener! He was grabbing it and swinging it and- Oh Heather! It was so scary! Just look how big it is!” Yuna lays it on thick.
Heather squeezes even tighter!
She grits her teeth and glares at me.
The cold in her eyes makes me shiver.
Heather tightens her grip even more!
Too tight!
She manages to start cutting off blood flow!
Tears begin flowing from my eyes!
We both look down.
Veigns have popped up on the exposed portion of shaft and the mushroom head is turning a deep purple!
The dark color is spreading to the exposed section of shaft.
Another agonizing moment goes by before Heather, mercifully, loosens her grip.
She keeps holding my penis, the threat of another painful squeeze ever present.
She looks down, panting.
The anger, glowing embers in her eyes.
“Oh? You think his ‘big wiener’ is ‘scary’?” Heather asks.
I gulp.
Did I just hear a slight ‘purr’ in her voice?
“Well, maybe not ‘scary’.” Janine corrects.
“But it’s still huge!” Yuna points.
“Yeah!” Marie nods. “And chasing us with it wasn’t nice!”
Marie hops up from her seat.
“I had to slap it away when Shy shoved it in my face!” She points.
“Hah!” Heather gasps.
She again applies the ‘strangle hold’ from before to my penis!
“Ugh!” I groan and raise up on my toes!
“H-Hea-Ther!” I choke out, but it sounds like “M-Mum-Mem!” through the wadded panties.
For a tense moment, I seriously think Heather is gonna rip my dick off!
“Heather! Stop! I think it hurts!” Janine yelps.
Heather freezes, still strangling my cock!
But again, showing mercy, she loosens her grip.
“Janine.” Heather looks over her shoulder. “It’s SUPPOSED to hurt. Shy shouldn’t have chased you with it, and CERTAINLY shouldn’t have had it anywhere NEAR your faces!”
Heather squeezes again, looking down.
She loosens her grip again.
She looks me in the eye.
That glint of fire flares as they narrow.
“You said Shy had my panties, and was touching himself?” Heather looks over her shoulder.
The girls nod.
“He had them on his face!” Yuna added.
Heather’s grip tightened, momentarily, then loosend to a soft ‘hold’.
“Hmm.” Heather looks at me.
“Shy,” She says stearnly. “Were you SMELLING my panties?”
Both me and the girls gasp!
I press my tongue against the wad, trying to dislodge it.
Heather squeezes.
I clench my eyes closed, squeezing more tears down my face.
I nod.
The girls giggle.
“Oh? And do you LIKE how they smell?” Heather asks.
“MMM!” I nod furiously.
“Hehehehe!” The girls giggle.
“Ew! Shy!” Janine scolds.
“No no, Janine.” Heather glances back. “He clearly has ‘good taste’.” She smirks.
Heather looks down.
She loosens her grip again.
I see that glint in her eyes as she looks back up at me.
“Janine? What do you think of Shy’s ‘wiener’, really?” She smirks.
Janine hops up and steps next to Heather.
Janine leans in and looks at my penis.
Her eyes are wide and her mouth, agape as she takes it all in.
“It’s definitely ‘big’ isn’t it?” Janine looks up at Heather.
“I’d say.” Heather cocks an eyebrow.
“Mummumuffafa!” I mumble, desperately.
Heather reaches up and wipes the tears from my face.
“Now, now, Shy. Don’t be so, well… ‘shy’.” Heather smirks.
“Are they all that big?” Yuna asks.
“I don’t think so.” Heather shakes her head.
We all look at my penis in Heather’s hand.
“I can see why you girls would run. I would too, if Shy chased me with this thing swinging around. Hmhm!” Heather smirks.
Heather narrows her eyes, but keeps smirking.
“Shy, we’re going to ask you some questions. I think it’s important that me and Janine get to know our brother a bit better.” Heather looks down. “Don’t worry. They’ll just be simple yes or no questions, so you can just nod or shake your head. Got it?”
I nod.
“Good boy. First, a test. Shy, do you ‘like’ having my panties in your mouth?” Heather asks.
Before I can nod or shake, my penis twitches.
Heather grins.
“Hehehe!” The girls giggle.
I keep my head still.
“Shy? Answer the question.” Heather squeezes.
I quickly nod ‘yes’!
“Eeeeeeeeeewwww!” Yuna squeals, scrunching up her face in a grin.
Heather beams.
“I thought so.” She shrugged.
“Shy?” Janine asks. “Do you want to taste MY panties? Hehehe!”
My little sister asks.
“M-mm! Mph-mummum!” I shake my head violently from side to side!
A definite ‘NO’!
But…
My penis twitches!
Heather gasps.
I look at her- pleading!
I can’t help it!
I don’t want to taste Janine’s panties!
It’s just a reflex to the taboo question!
Heather narrows her eyes and smirks.
“Hmmm. I’m not sure. Another question, just to lock in a baseline.” Heather suggests.
She leans in and whispers in my ear.
“That can stay between us, for now. They already caught you jerking off while sniffing MY panties. I don’t want them knowing how perverted you REALLY are.” Heather squeezes.
I wince.
“Shy?” Heather asks. “Are you embarrassed to be standing here in front of these little girls while I hold your big dick?”
I nod.
Heather feels my penis twitch.
“He’s telling the truth!”
“Good!” Yuna yelps!
“You should be! It’s real naughty! Hehehe!” Marie adds.
“Hmmmm.” Heather thinks for a moment.
“Shy, do you play with yourself a lot?” She asks.
“Hehehehehe!” The girls giggle.
Such an embarassing thing to admit in front of them!
But…
I nod.
“Eeeee! Hehehehe!”
The girls squeel and giggle hopping up and down.
“Mph!” I feel it.
“Mmmmmmm!” I look down.
Heather is slowly, subtly tugging my penis!
“Shy.” Heather asks. “Do you LIKE standing here naked where we can all see your big dick?”
She stops tugging.
I shake my head.
My hard penis twitches!
Heather lights up.
I shoot my eyes at her.
“LIAR!” Heather gasps with a grin.
“How do you know?!” Janine yelps.
“His ‘dick’ gave him away!” Heather shakes my hard penis a bit.
“Mmmm!” I moan.
“Huh?” Janine asks.
“You see girls, he can nod or shake his head, whenever-
Lie-
But his dick twitches in response, so I KNOW if he’s lying or telling the truth!” Heather explains.
The girls share confused looks, but then, Janine gasps.
“You called him a liar when you asked if he ‘liked’ being naked in front of us! You mean he DOES?!!”
“MMPH! Mumumph mumph!” I argue, but my penis twitches.
Heather grins and shakes her head.
“Shy! That’s so gross! You LIKE showing us your big dick?!”
I shake my head aggressively, no!
“Mmmmm!” I groan.
Heather squeezes, making me freeze.
“Next question.” She looks at my penis. “Hmmmm.”
“Can I ask a question?” Janine asks.
Heather grins.
“Of course. This is an open discussion.”
Janine hops over in front of me.
She grabs my penis above Heather’s hand!
“Oh!” Heather gasps.
“Mph!” I yelp.
Oh gah!
Heather lets go as Janine moves her small hand down to the center if my cock!
Janine is holding my penis now!
“Oh, um, Janine?” Heather suddenly seems nervous.
“Wooooooow.” My little sister sighs.
Her hand holds my cock in the center taking up only the middle 3rd of my length!
Janine’s eyes grow wide as she looks up at me and smiles.
Yuna and Marie practically materialize at her sides!
Janine gently squeezes.
“Mphmummumphmumum!” I protest to my little sister’s touch, but Heather keeps me still.
Janine holds my penis for an agonizingly long time before Heather prompts her-
“Janine, you have to ask Shy a question.”
“Oh! Hehehehehe! Right! Hmmm.” Janine giggles and thinks.
“Shy. Since you like being naked for us, do you want to show YOUR friends your big wiener?” She grins.
I shake my head aggressively, but Janine’s touch and the thought of girls in my class seeing me has an effect.
Me penis twitches sharply in Janine’s petite hand!
Janine gasps and grins.
“Mumphmummumphmphmph!” I try to cut her off.
“He does! His wiener is twitching!” Janine declares proudly.
Heather smirks.
“I’ll have to remember that.” She narrows her eyes.
“I have a question!” Yuna chirps.
Janine lets go as Yuna reaches out.
Yuna tentatively reaches out.
She rests her fingertips along the top of my rigid shaft!
I shudder as it tickles!
“Mmmmmmm!” I moan.
“Has your wiener always been this big?” She grins, looking from me to her hand on my penis and back again.
Of course it hasn’t!
But, with all the talk about how big it is, I just go with it.
I need this to end!
I nod.
“Liar!” Heather scolds.
Yuna looks startled and confused.
“But his wiener didn’t twitch.” She offers.
“Keep him here! I’ll be right back.” Heather starts to exit the kitchen.
She glares at me before leaving.
“Keep your hands on your head.”
She then looks at the girls.
“If he moves or tries to do anything else to you like before, yell.”
Heather then exits and heads upstairs.
Yuna is still holding my penis.
Her grip is gentle.
I move my hips slightly.
My penis moves in her tentative grasp.
“Huh?!” Yuna gasps.
I freeze.
“Shy! That’s naughty! Hehehehe!” Yuna giggles.
She then looks at me and grins.
“Do it again.”
Against my better judgement, I slowly move my hips again, gently moving my penis back and forth in her delicate hand!
Fuck!
It feels good!
“Mmmmmmm!” I moan, closing my eyes as Janine and Marie watch.
Yuna stays perfectly still, content to simply hold my hard penis as I slowly thrust.
This is bad!
It feels too good!
Too good and too naughty!
Too good to stop!
Janine and Marie get closer.
“Shy! That IS naughty!” Janine beams.
Marie looks on in stunned silence.
I try to force myself to stop!
Yuna is still holding my penis, and I’m still moving back and forth!
If I keep going-
“Eeeeewwwww!”
Yuna squeals as she lets go.
I look down.
“MMMMMM!” I groan in dismay as I see the clear stream of fluid hanging from the tip of my penis!
I almost drop my hands to grip my penis and finish myself off, but then I remember the girls are watching!
And, I remember Heather’s warning.
I’m unsure of what she’ll do if I disobey.
I keep thrusting my hips.
I look at Janine, pleading.
I thrust my hips, slowly, while nodding at my twitching, leaking erection.
“SHY! THAT’S SO GROSS!” Janine yelps.
I instantly hear the pounding footsteps from above us.
Along with the girls, I track them with our eyes- through the cieling, down the stairs- through the livingroom, until Heather bursts back into the kitchen with a large, beige binder in her arms.
“Everything alright?” She glares at me.
She then looks at my penis and gasps.
There’s a clear string of precum stretching to the floor!
Her mouth drops open in shock!
Heather walks over and slams the binder onto the table.
She keeps glaring as she regards the clear string of liquid hanging from my erection.
“SHY! DID YOU-?!” She yells.
I shake my head.
“MMMMPH! MUMMUHMUMUM!”
“He was humping Yuna’s hand!” Janine points.
“Hehehehehe!” Yuna lets out a low, gutteral giggle.
“WHAT?!” Heather yells.
She walks over to the counter and grabs a wad of paper towel.
She then steps to me, shoving the wad in my chest.
“Wipe.” She scolds.
The force she shoves me with is enough to make me stumble.
I do as I’m told.
I take the paper towel and wrap it around my penis, collecting the leaking precum.
I can’t help but give myself a few tugs.
“Hehehe!” The girls giggle.
“Shy!” Heather hisses.
I stop and hold the paper towel out to Heather.
“Ew! No! Just drop it for now.” She points to the floor next to me.
I drop it where she points.
“Might need them again.” She smirks.
No!
She wouldn’t make me-!
Would she?!
In front of ALL of them?!!!
“Mmmmm!” I groan as my ordeal continues.
Heather goes back to the binder.
“Now. Shy just lied. You asked if his ‘wiener’ had always been that big? And he said YES?!”
My heart drops into my gut.
She opens to a center page.
“This was 5 years ago, but look at that!” Heather points to the page with a ‘thud!’
The girls gather and immediately begin giggling.
They look from the page, to me and back again, stunned grins on their faces.
“He DID lie!” Janine gasps.
Heather smirks, wickedly.
She removes a photo from the page and walks it over to me.
“Proof!” She holds it up in my face.
There, a picture of 8 year old me, getting out of the tub.
My legs are spread and I was clearly caught off guard.
But the memory returned.
My then, new, 10 year old step sister, Heather had dug out her dad’s polaroid camera and the first thing she caught was my prepubescent body getting out of the shower.
Just as she’d said, I was definitely NOT as big down there as I am now.
My penis is limp and tiny.
It’d be another 2 years before I grew into my current size.
Heather grins as she kneels in front of me.
She holds the picture next to my erect penis.
The girls gather behind her, leaning in for the direct comparison.
“Jeez, Shy!” Janine sighs. “Your wiener’s gotten a lot bigger since then! Hehehe!”
All the girls being so close, leaning in, Heather on her knees in front of me-
My penis begins twitching, violently!
Heather gasps, her eyes going wide.
“Mmmmmmm!” I groan as I feel it!
Heather looks up at me.
My body begins convulsing.
Janine, seeing my erect penis bouncing up and down on it’s own, misreads the situation.
“Shy! Quit being naughty! Hold your thingy still!”
To my horror, my little sister grabs my penis.
“MPHMUMMMMMMMMMM!” I scream, my voice loud, but still muffled by Heather’s panties.
My knees wobble.
Heather, realizing the danger, stands and grabs Janine’s wrist, pulling her hand from my penis!
Her delicate fingers slide down my shaft and over the head.
I clench with everything I have!
My penis twitches up and down, up and down-
Precum stringing to the floor!
Janine’s touch as almost too much, and now, I’m left in a dizzy, almost painful, excrutiatingly embarassing limbo!
“What’s happening?” Janine asks, concern now present in her voice.
Heather takes stock of the situation.
They’ve all seen my erect penis, balls, everything.
My body has no more secrets from my sisters and their little friends.
Well, there is still ONE secret,
but Heather is unsure even SHE should see that.
Still though, Shylo was masturbating to her panties when he was supposed to be babysitting.
And after everything the girls had accused him of, Heather wondered, did Shylo deserve that final, ultimate degradation?
She herself had determined he enjoyed her panties, and to a degree, was enjoying being naked.
I stand here, on the verge of what is feeling likely to be, the most powerful orgasm of my young teen life.
An orgasm I should be having in the privacy of my own room, with my own hand.
An orgasm away from the eyes of my sisters and their friends.
The girls.
They’re all just staring!
My cock is throbbing and leaking!
I’ve never let so much precum build up before!
Gah!
This is so embarassing!
Heather stands straight.
She steps to my side.
“Shy,” She holds her hand out, hovering it near my penis, but not touching.
“I think we’ve all seen enough.” Heather says, taking stock of the situation.
“Awwwwww!” The girls groan, collectively.
“Are you ashamed of yourself?” Heather asks, true disappointment in her voice.
I wince.
And nod.
“IF you ever get to babysit alone again, are you going to try and attack the girls again?” She asks, more ‘venom’ in her tone now.
“Hehehe!” Janine giggles.
“Yeah, Shy! Are you gonna chase us with your big weiner again?” Yuna grins.
Marie just stares, smiling.
“Muh-mummum- muh-mummum!” I argue, but nod.
My penis twitches.
“I can’t tell if that’s a ‘yes’ or a ‘no’.” Heather narrows her eyes.
She knows.
She’s just dragging out my agony.
Janine, still blissfully unaware of the precariousness of the situation smiles.
“I know how to tell! Remember?”
Janine swiftly swoops to my other side, opposite Heather.
Both Heather and I watch in horror as Janine reaches over and wraps her delicate hand around my penis!
The reaction begins.
“Shy, are you gonna chase us with-“ Janine starts.
Before she can get the rest of her question out, the gentle touch of her hand puts me over.
My penis gives it’s final involuntary twitched before the ripples of orgasm override everything else.
Like earlier, I begin thrusting in Janine’s gentle grasp.
“-your big wiener?” Janine finishes her question.
My penis responds, but it isn’t the answer everyone is expecting.
“Mmmmmmmmmmmmm!” I groan as I give in and thrust into Janine’s hand.
‘Splurt!’
The sound us audible as a thick jet of cum shoots from my penis!
“Oh! Shit!” Heather yelps.
I’m not sure if her initial intention is to remove Janine’s hand from my penis, or if it is to replace it.
But neither are what happens.
Heather’s hand wraps around another portion of my penis, as well as part of Janine’s hand, locking it in place.
The addition of Heather’s touch results in another powerful wave of orgasmic sensation rippling through my body.
‘Splat!’
The first jet of cum splatters the floor between Yuna and Marie.
‘Splurt!’
The second wave resulting from Heather’s touch erupts forth.
Both my sisters-
Younger and older-
are holding my penis!
‘Splat!’
The second jet of cum hits the floor.
I look at Heather.
She’s staring at my penis in her’s and Janine’s shared grasp.
I thrust again.
And again!
The initial ‘wave’ of orgasm resulting in my double ejaculation retreats.
I stop thrusting.
Janine and Heather’s hands, though, keep moving!
They’re now actively tugging my penis!
Is this Heather?!
Or Janine?!
“Ewwwwwww!! It’s slimy!” Janine scrunches her her face.
“Uh huh!” Heather gasps, a short ‘moan’ accompanying it!
Tug.
Tug.
Tug.
“MPH! MMMMMMM!” I moan and shiver as one final ‘jolt’ of orgasm leaves my body in a final ‘squirt’.
Splat.
I pant through my nose.
Shivering.
Heather and Janine keep tugging, but I feel my penis stretch, becoming more pliable as it softens.
“Oh!” Janine gasps.
“Oh! Oh god!” Heather also chirps, realizing what just happened.
She pulls her hand away, along with Janine’s.
She pulls Janine back, avoiding the cum puddle.
“Um, okay.” She looks at me, then at Yuna and Marie.
She points at me, then at the puddle.
“Clean that up! We’ll be back!” Heather leads Janine away, leaving me with Yuna and Marie.
I kneel and begin wiping and sopping up my cum with the paper towel.
I can feel Yuna and Marie staring.
They’re whispering to one another.
I stand and walk to the trash can, tossing the paper towel away.
I walk back over to the 2 girls who just witnessed my ultimate degredation.
I don’t bother covering, as they’ve now seen literally EVERYTHING!
They both giggle and keep glancing at one another, then at my penis, then back again.
I take a deep breath and press my tongue against the wadded panties, the soft cotton having absorbed all the moisture from my mouth.
I cross my arms and lean against the wall.
Heather and Janine return.
Janine looks nervous, now.
Heather looks stearn.
I stand and place my hands on my head again.
Heather smirks.
“Right. Shy, go get dressed.”
I do as she says.
I move to take the panties out of my mouth, but Heather stops me.
“No. Leave those in.” She says flatly.
I sigh and continue to my room.
I hear Heather begin talking to the girls as I walk down the hall.
I pass Heather’s room, where I’d absconded with her panties, my penis twitching again with the thrill I’d felt.
I hastily get dressed as the reality of what just happened sinks in.
My step-sisters-
Their friends-
Just witnessed the most private thing imaginable!
Heather-
JANINE!
Of all people to make me-!
I look at my bed.
I think back to moments earlier-
Getting caught by the girls.
I don’t know how I’ll ever be able to look at either of my adopted siblings ever again, not to mention Janine’s friends.
Gah!
How stupid!
I should have gotten dressed BEFORE trying to retrieve Heather’s panties!
I press my tongue against the wadded fabric.
I move my hand to tug the panties from my mouth, when I’m stopped by Heather clearing her throat from my doorway.
I turn and reflexively put my hands on my head.
Heather grins and shakes her head.
“Shy, sit down.” Heather points to my bed.
I sit.
Heather shuts my door and walks over to sit beside me.
She looks around, then, behind her at my mattress.
“So, this is where you jerk off usually?” She smirks.
“Mphmummuh.” I mumble.
Heather looks at me.
“Guess we can take those out now so we can ACTUALLY chat about things.”
She reaches up and pinches the panties.
She pulls and I gag on the dryness as they exit my mouth.
“Ugh! Cack! Cack!” I choke on the dryness.
“Mlem!” I lick my mouth, trying to restore the moisture.
The taste of the floral detergent lingers.
“Heather! I swear! I didn’t do anything to-“
Heather lifts her finger to my lips.
“I know.” Heather smirks. “The girls confessed.”
“Huh?!” I gasp.
“Well, they confessed to making up SOME of what they told me you did.” Heather corrects.
I feel a wave of relief wash through me.
“But you still chased them around, NAKED! What were you thinking?!” Heather shakes her head.
“I was trying to get your panties back.” I mumble, sheepishly.
“Jeez, Shy!” Heather hugs herself. “It’s so gross! Janine told me THAT part was true. You had my panties on your face? While ‘touching yourself?!” Heather shivers.
Heather lays bare the sheer perversion of the act.
I can’t look at her.
Heather examines the panties in her hand.
“Gah! And these were a clean pair, too!” She scolds.
She huffs.
I can see out of the corner of my eye, she’s examining her panties.
“Shy, look at me.” She instructs.
I turn my head to see her green eyes glowing with a softer warmth than the rageful fire from before. “What you did was disgusting, and wrong. We’re family! And chasing them, NAKED?!! Even if you weren’t trying to strip them, that was SO stupid!”
“I know! Heather! Please! Don’t tell mom and da-!” My words catch.
Our parents!
They’ll KILL me!
Heather smirks.
“No shit.”
Heather looks behind her to my bed again as she leans back.
“And now, you’ll need to deal with Janine, Yuna and Marie. They’re not likely to forget this.”
“What do I do?!” I gasp.
“Well, for starters, DON’T chase them around naked! DUH!” Heather actually smiles sitting back up.
“You owe them an apology, for sure. Even though you didn’t ACTUALLY try and hurt or strip them, you still chased them with your, how did Yuna put it?” Heather pretends to think.
“Oh, right! ‘Big wiener’! Hah!” Heather actually chuckles.
“Heh!” I blush.
Heather is looking at my shorts.
She looks over at my shut door, then back at my shorts.
She looks at the panties in her hand.
“Shy, you didn’t have these on your dick, did you?” She asks.
“Wha-?! NO!” I yelp. “Just my face! I swear!”
I gulp at my confession.
“Hmhmhm!” Heather chuckles. “Well, good. I still need to wash them, since they’re wet with your spit. Yuck!”
Heather looks at the door again.
“Wait here.” She stands and exits my room, leaving me sitting on my bed.
At least it seems the worst has passed.
Gah!
Still!
They’ve all seen everything!
It really was stupid-
Chasing after them before getting dressed.
My dignity is forever lost to them.
I play back the stupid game of ‘naked keep away’ they’d forced me into.
Ugh!
I cover my face as I lay back.
“Shy.” Heather speaks as she returns, closing the door.
She walks over and sits next to me again.
I sit up.
“Just so you stay OUT of my room from now on, here. Hold out your hand.” She nods.
I do.
“Don’t get caught with these, and don’t do anything until you KNOW you’re alone.”
“Huh?” I blink.
“This is to stop you from becoming a panty thief deviant.” Heather blushes with a smirk.
She places a light blue, balled up garment in my hand.
She stands.
She walks back over to the door and turns to look at me.
“I know this was an awkward chat, but I think we both learned some things.” She smirks. “Now, you still owe the girls an apology, but I’ll give a bit to gather your thoughts.”
Heather grips the knob, facing away from me.
“By the way, ‘those’ are the ones I was wearing earlier. Nice and fresh. Enjoy.” She exits, closing the door behind her.
I look at my hand.
I unfurl a crumpled up pair of light blue panties!
My penis twitches!
I rip off my clothes, panting.
Every moment from earlier plays out in my head, refueling my pulsing erection!
I lay back, grip my penis and press the garment to my face!
The floral detergent smell is faint in this pair.
Still present, but masked behind a sweet, ‘tangy’ aroma.
I inhale.
Amazing!
I flick my tongue.
A sweet, but sour, somewhat ‘musty’ taste dances across my tongue, it compliments the smell perfectly!
I’m stroking, faster than ever!
I rapidly reach orgasm as I let out a muffled yell into the panties, “HEEEEEAAATHERRRRR!”
I feel the hot sting of release, followed by the wet splatter of semen on my chest and abs.
I keep tugging, but this time, I’m quickly spent-
Drained.
I pant, keeping the panties pressed to my face, tugging my quickly deflating penis.
I relax.
I inhale one more time before tucking the panties beneath my pillow.
I stand and walk to my closet.
I dig through my hamper and pull out a dirty pair of boxers.
I wipe myself down and toss the boxers back in the hamper.
I dig out a fresh pair from my drawer, as well as a fresh shirt and shorts.
I get dressed and go to exit my room.
I open the door and gasp as I see Heather leaning against the wall, another smirk plastered on her face.
“That was quick.”
Had she heard?!!
“Come on. The girls are ready for your apology.” Heather gestures down the hall.
We start walking.
I brace myself for what is surely going to be another awkward chat.
An Awkward Chat (One-off. Complete.)
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NudeBaG
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An Awkward Chat (One-off. Complete.)
Last edited by NudeBaG on Sun Jul 05, 2026 12:42 pm, edited 2 times in total.
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Re: An Awkward Chat
Fantastic story, NudeBag! A tour de force for sure! Can't wait for the next part.
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NudeBaG
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- Jeepman89
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Re: An Awkward Chat (One-off. Complete.)
I just realized the story is complete. No worries. Great story.
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Skylar21
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NickTwisp
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Re: An Awkward Chat (One-off. Complete.)
This is certainly one of the best "boy caught masturbating" stories I've ever read.
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NudeBaG
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Re: An Awkward Chat (One-off. Complete.)
Wow!NickTwisp wrote: Sun Jul 05, 2026 4:29 am This is certainly one of the best "boy caught masturbating" stories I've ever read.
Thank you
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