Another one-off
I opened the door and slung my bag to the living room corner.
I saw my little sister’s bag, as well as another bag I didn’t recognize.
She knew better than to have friends over without mom being home!
She was only 12 after all.
As her 16 year old big sister, I was in charge when mom was away!
I quickly made my way to her room.
The door was closed.
Another broken rule!
I reached for the knob, but then heard her voice on the other side.
“Hehehe! I like the way thry look!” She said.
“Th-Thanks. How long do I have to stay in my underwear?” A boy’s voice responded.
A boy?!
UNDERWEAR?!
My big sister instincts kicked in and I barged into her room!
There my little 12 year old sister, Shanon was, sitting crosslegged on her bed with a pillow in her lap.
From what I could see, she was still fully clothed.
Whew!
But then, I looked at the boy sitting on the bed next to her in nothing but his boxers!
It was 13 year old Chuck Masterson from down the street!
I knew him, as he was quite popular with all the neighborhood girls, and even though he was only 13, even I had to admit, he was quite good looking.
Chuck threw his hands over his crotch!
I saw his clothes on the floor and quickly scooped them up!
“What the hell are you guys doing?!” I gasped.
Chuck looked panicked, his mop of blonde hair flopping as he looked from me to my sister frantically!
My little sister Shanon, never one to lie, spilled the beans instantly.
“Kylee! I didn’t hear you get home! Don’t tell mom!” She begged, standing up.
I again assessed the situation.
My 12 year old sister was still fully clothed.
Her 13 year old friend, A BOY, was in nothing but his boxers!
I, her 16 year old sister was now holding that boy’s clothes.
I did the math, but couldn’t solve the equation.
I looked back at Shanon.
“Don’t tell mom what?! That I caught you fooling around with a boy?!” I chastized her.
Shanon was quick to respond.
“We weren’t fooling around!” She exclaimed. “We were solving a bet!”
She said.
A bet?
What kind of bet between a 12 year old girl and a 13 year old boy requires him to be in his underwear?!
“A bet?! Huh?! What kind of bet?!” I asked, still holding Chuck’s clothes.
“Boxers or briefs!” Shanon said with a smirk.
I looked back at Chuck, who was now cupping his hands over his crotch.
He was also clearly wearing baggy boxers.
I then came to the realization that my little sister, 4 years my junior, had now gotten further with a boy than I had!
My own teen hormones kicked in and took control.
I was the older, more mature, more responsible one, after all.
I clutched Chuck’s clothes to my chest and shut the door.
“Oh. Well then.” I said. “I guess the answer is boxers.” I looked down at the baggy plaid underwear that was all Chuck had on now.
“Yeah!” Shanon chirped. “And I bet boxers! So he had to show me!”
Chuck remained still and silent.
“Um, yeah. So can I have my clothes back?” He asked, looking at me.
“But we were hanging out! Just stay in your boxers!” Shanon pouted.
My heart fluttered.
“If the bet was to hang out in your underwear, then that’s the bet.” I shrugged.
I couldn’t help but notice how good Chuck looked for a younger guy!
I’m ashamed to admit, but outside of sex ed, I’m really inexperienced.
Like I said, I’m jealous that Shanon had indeed gotten further with a guy than I had!
I had to correct that.
“I guess you should just be glad the bet wasn’t to get naked.” I said, unable to hide my own smirk.
Shanon giggled and Chuck blushed, his entire body turning red.
I felt my vulva pulse!
“Awww! I should have bet that if got it right, you’d have to get naked! Then I would get to see your weenie! Hehehe!” Shanon giggled.
The energy in the room shifted.
Chuck began trembling.
Shanon suddenly looked downright predatory, grinning with the mischief only a hormonally charged adolescent girl could conjure!
Chuck laughed nervously.
“Has anyone ever seen you naked, Chuck?” I asked.
“Wha-?! N-No!” He stammered.
“Why don’t you show us, then?” I said, almost losing my cool.
“I can’t do that! You’re girls!” He gasped.
At 13, I would think Chuck would be into sex by now.
After all, he willingly stripped to his boxers for my little sister.
“I think if you want your clothes back, you’re gonna have to show us your-“ My words caught in my throat.
This would be MY first time seeing a naked boy too!
I just nodded at his crotch.
Shannon was quick to continue the barrage.
“Ooooo! Yeah! I wanna see! I wanna see you all naked!”
It almost looked as though Shannon were about to pounce on Chuck!
Gah!
She really was about to get further with a guy than me!
No!
She wouldn’t know!
Just play it cool.
I quickly turned, opened the door and threw Chuck’s clothes into the hall!
I turned back to them, shutting the door behind me.
“I-I think I should go.” Chuck stood up.
Big mistake!
Shannon released all that pent up energy and pounced, lunging forward off the bed and yanking Chuck’s boxers to the floor!
I gasped.
Even though it was just for a split second before he covered with his hands, there it was!
I didn’t see any pubes, but I saw his penis and balls!
For MY FIRST time!
He cupped his hands over his crotch as he spun and fell face down on the bed!
Shannon, still gripping his boxers, yanked them all the off and stood up, giggling like crazy!
She gasped, staring at Chuck’s cute butt as he tried to sink into the mattress.
At least I’d gotten to see the REAL goods before she had.
I was ahead again!
But I wanted to see more!
Could Chuck get an erection yet?
Oh my god!
Would we get to see him HARD?!
I had to learn everything I could now!
But I also couldn’t let my little sister know that we were pretty much in the same boat together!
I grabbed his boxers from her and tossed them out the door again!
“Hehehehe!” Shannon giggled with glee.
“Oh! Shannon! We have a naked boy on your bed! What should we do?” I asked.
I was partially teasing Chuck, but also legitimately curious as to what Shannon intended.
We both just stared at Chuck’s bare butt.
And it was quite nice for a 13 year old!
I’d been ogling the boys in gym class since I was 10!
I couldn’t imagine Shannon’s excitement in this moment.
I suddenly remembered my position.
I HAD to keep my cool!
I’m in charge!
I’m the mature and knowledgeable one!
Shannon quickly hopped on the bed again and began trying to turn Chuck over!
“Hehehe! Roll over! I wanna see!” She chirped.
I hopped on the bed with her, on the other side of Chuck.
Just my weight on the bed almost rolled him over!
Together, with Shannon pushing and me pulling, we rolled Chuck onto his back!
“No please!” He begged.
Now that were holding his arms, we could really feel him trembling!
He definitely wasn’t as strong as the boys in my grade.
He didn’t have nearly the muscles some of them did, but I didn’t care about that, and neither did Shannon!
Chuck was really panicking now!
“Show us your weiner!” Shannon cheered one last time.
“On 3!” I said. “1, 2, 3!”
Shannon and I said ‘3’ in unison.
We each pulled one of Chuck’s arms away, reveiling his privates!
Neither of us said anything initially, but there it was!
I could see some blonde peach fuzz on his tight ballsack, but other than that he looked pretty hairless.
But his penis!
Oh my!
It was really cute!
It was bigger than I initially thought too!
But it was flopped over to the side, resting over his hip.
We were all frozen.
I took charge again, even though I really didn’t know what to do.
I just wanted to keep staring.
“What do think, Shan?” I asked, again barely masking my own nerves.
“Woooooow!” She let out a breathy sigh.
I was mentally taking in every detail!
His balls, his shaft, especially the cute little mushroom head at the tip!
My first naked boy!
Shannon leaned over to get a closer look and exhaled as she did, right over his privates!
When she did, his penis twitched!
“Ah!” Chuck gasped. “No! No! No!” He muttered and tried to roll over again.
But we held him down still.
Chuck wiggled his hips, making his penis move around, which made Shannon and I laugh.
But then we stopped laughing and watched as Chuck’s penis grew!
It twitched and pointed up!
I added these details to my memory of this moment!
It could move on it’s own like that?!
“It looks different now!” Shannon chirped.
“Oh!” I gasped, realizing Chuck now had an erection!
This must be a ‘boner’!
That also means this is the biggest his penis can get!
I looked at Shannon.
She was grinning and biting her lip so hard I thought it might bleed.
“Um,” I couldn’t speak.
There it was right in front of me!
A naked boy’s erect penis!
It looked like it had doubled in size!
“Shit! P-Please! Don’t look!” Chuck gasped.
“Yeah right!” I blurted out, almost laughing.
Looking at this boy’s naked body- seeing his smooth, erect penis- my hormones were going ballistic!
I looked at Shannon again.
She was going to try and go through this ALONE?!
I simultaneously felt proud of my little sister, while also being disappointed in her, but also understanding completely.
Regardless, we were here now.
We had a NAKED BOY, NOW!
Right!
I had to keep up my ‘big sister’ act.
How far could I take this?
This was my first time, too, after all.
Both Shannon and I were still holding his hands, but he wasn’t fighting anymore.
“It looks-“ Shannon paused. “Hmmm.”
I was also fascinated, being my first IN PERSON penis.
I didn’t know if it was big or not.
I liked how smooth the shaft was.
I liked the pink mushroom head, too.
I pictured how it would feel during sex.
I knew my fingers felt good.
I hadn’t used a dildo yet.
I then took in the full size of the whole package.
It fit Chuck’s body well.
It looked good.
“It looks funny!” Shannon finished her thought.
Chuck’s erect penis was pulsing!
I again had to put on my knowledgeable big sister act.
“Chuck! You have a boner! Hmhm!” I teased.
Using the word for the first time felt naughty, and I had to chuckle.
Chuck was panting, looking from Shannon, to his penis, then to me, on repeat.
“What now?” Shannon asked.
I was actually stumped as well.
We had him.
NAKED!
We could see and touch him ANYWHERE we wanted!
I suddenly realized the need to stay ahead of Shannon (as far as experience goes).
“Well,” I said, trying to hide my trembling. “Now that we’ve seen Chuck’s private parts, why don’t we touch them?” I suggested.
Shannon gasped and looked shocked.
“No! P-Please!” Chuck begged. “Don’t do that!”
He was nervous!
I felt my vulva pulsing!
I was getting wet!
I had to make the first move, before Shannon!
I reached forward and gripped Chuck’s penis in my fingers!
I gasped!
His skin was so smooth, but his penis was SO rigid!
I moved my fingers and the skin moved with them!
It was so strange, but also really neat!
I was elated!
I was touching a naked boy’s penis for the first time!
I was in a trance!
It was so warm!
It felt like it was getting harder!
His balls were moving as he breathed!
“Let me! Let me!” Shannon gasped.
I moved my hand and watched as Shannon gingerly pinched his penis!
She proceeded to touch his penis all over!
Even examining his pee hole!
I saw her shift, rubbing her thighs together.
She was enjoying this just as much as I was!
Shannon lit up.
“Chuck! I’m gonna tell ALL the girls in our class about this! I’m getting to play with your weiner!”
Chuck sat up at that, but Shannon was still holding his penis.
“Y-You can’t!” He gasped.
As the eldest, I pulled my authority card.
“Sorry dude. She’s holding your penis.” Saying it out loud made me tingle! “I think we can do whatever we want.”
Shannon seemed to get even MORE excited.
“Chuck! Now that I’ve seen you naked, will you be my boyfriend?!” Shannon asked.
I was shocked!
“Shan! You’re only 12!” I gasped.
Chuck gasped as well.
“So?” Shannon looked at Chuck again, still holding his penis in her hand.
“PLEASE! Shan! You can’t tell our friends about this!” Chuck begged.
I jumped on the opportunity to exert my authority.
“She absolutely can! She can tell ALL your little friends about seeing and touching you naked!” I said.
Shannon was beaming with the realization of the power I’d just granted her.
Shannon repeated her question.
“Chuck? WILL you be my boyfriend?”
“Um,” Chuck was trembling, staring at Shannon’s hand on his penis!
I took another jab at him.
“If you say no, Shannon and I will tell everyone you have a little penis!” I threatened.
Shannon gasped and looked at Chuck’s penis in her finger tips.
Admittedly, Chuck absolutely did NOT have a little penis!
In fact, he had a very nice, big, smooth penis!
But I knew boys were sensitive about size, so I felt like adding that into ny power play.
Shannon gasped.
“Chuck! Your penis is TINY?!”
She examined it as she angled it upwards.
Honestly, in her delicate hand, it looked pretty big!
“I don’t think-“ Shannon started to speak, but I had to cut her off.
“I just mean that if Chuck DOESN’T want to be your boyfriend, we’ll tell everyone about his small penis.” I corrected without completely backpedalling.
I re-established the power dynamics at play.
I reached down and gripped Chuck’s penis in my hand, replacing Shannon’s.
It was so hot and stiff!
I wondered what it would feel like inside me.
But Chuck would never know that.
My heart was racing!
I was in complete control over a naked boy!
I know he and Shannon are like, ‘a thing’, but I’m not about to let this opportunity to learn more pass me by!
Hell!
If I leave now, Shannon really WILL have more experience with a guy than I do!
No!
I have to maintain control of the situation!
I want to see EVERYTHING before Shannon does!
“So? Chuck? Will you be Shannon’s boyfriend?” I asked.
“Um,” He was still trembling.
Shannon was once again biting her lip so hard I thought she’d bleed!
My heart was pounding as I held Chuck’s penis.
I gave his penis a squeeze, making him moan.
“Well?” I asked.
“Y-Yes.” He muttered.
“Yes, what?” I pushed.
“Yes. I’ll be your boyfriend, Shannon.” Chuck said.
Shannon jumped up off the bed and squeeled with glee!
She bounced around her room a bit before hopping back on the bed next to Chuck.
“Yay! So that means I can play with your weiner whenever you come over!” Shannon blurted. “And we can hold hands, and kiss, and go on dates!”
She was overwhelmed with joy.
I was happy for her.
I felt pride as an older sister for having helped secure Shannon her first boyfriend.
But then another realization hit me.
She now had a boyfriend!
I was still single!
She was ahead of me again!
I was still holding Chuck’s hard penis.
If I had a boyfriend, I’d want to play with him naked all the time!
Chuck had an erection!
I can’t let Shannon and he be alone!
She might get even FURTHER with a boy!
No!
Whatever is going to happen, it’s got to happen with ME first!
“Shannon.” I said. “I want to make sure you know what to do, now that you 2 are a couple.”
Shannon looked confused.
“You know about sex?” I asked.
Shannon blushed and got timid and quiet.
Yes!
I still had authority!
Chuck also looked nervous.
“Like, when a boy sticks his penis in a girl’s vagina?” Shannon asked.
She squirmed and held her hands tightly in her lap.
I knew she HAD to be just as horney as I was.
Okay, she knew the basics.
“Yes. But do you know what happens to a boy’s penis?” I asked.
Shannon’s eyes darted to Chuck’s erect penis.
She shook her head.
I kept my guise as an authority figure going.
“When a boy get’s excited enough, his penis squirts sperm.” I explained.
Shannon’s eyes widened.
“That’s what makes babies.” I continued.
“So, when you guys are alone, do NOT let Chuck put his little penis in your vagina!”
I knew it was a crued description of intercourse, bit I just wanted to guage Shannon’s knowledge.
I was still ahead, it seemed.
Shannon gasped and looked at Chuck’s penis.
“Chuck! Are you gonna squirt your sperm?!” She asked bluntly.
“Um,” Chuck began panting.
I took charge again.
“He will if we keep touching his penis.” I said.
I then looked down.
This was it!
I was holding Chuck’s penis!
It was my first time!
I had just explained what would happen without actually having ‘first hand’ experience with what would happen.
Just an educated guess, really.
But I HAD to stay ahead of Shannon!
“So, Chuck. Should I play with your penis and make you squirt in front of my sister and I?” I taunted, but it was really more of a promise of things to ‘come’.
Shannon squirmed.
“Do it, Kylee.” She said with a breathy whisper, staring down at my hand on Chuck’s penis.
I was frozen.
Shit!
I’ve never done this before!
No!
All I have to do is play with it, right?
I’ve seen boys make the lewd gesture with their hands before.
‘Jerking’ they call it.
I gripped Chuck’s penis loosely in my hand and began moving up and down his shaft.
I’ll admit, it was sloppy as hell and I had NO idea what I was doing!
But that didn’t seem to matter, as Chuck began convulsing and breathing heavy!
God!
His penis was so warm and stiff!
But also, squishy?
How could a penis be hard and soft at the same time?
God this was fun!
I was actually playing with a boy’s penis!
Honestly, Chuck really did have a nice penis.
But I did wonder what it would be like to play with an even BIGGER penis!
I took another opportunity to further establish my authority, as well as make another jab at Chuck.
“You know, Chuck, if you had a big penis, Shannon and I could play with it together.” I said.
Shannon gasped.
“Too bad your penis is so small.” I sighed.
“It-it’s nah-not sm-small!” Chuck stuttered, his entire body convulsing.
God!
This was SO HOT!
I kept going.
“Yes it is, Chuck. And I bet you even squirt tiny. Huh? I hope you at least CAN squirt. Can you? Huh?”
I had no idea what I was saying.
I was lost in the moment.
I felt hot tingles spreading through my body!
I was squirming now, too!
What was about to happen?
Should I stop?
Should I put an end to this?
I realized that my hand was now sliding up and down Chuck’s penis rapidly!
It was slippery!
I looked at Shannon.
She was watching with wide eyes, biting her lip and squirming with her hands tucked in her lap!
That’s it sis!
Watch me jerk your boyfriend!
“Ah! Aaaaaaah!” Chuck moaned and bucked his hips!
A thick white jet of cum shot into the air and splattered his chest and abs!
I felt it as it shot from his penis!
I squeezed and kept stroking!
This was fun!
Another blast of white cum shot onto his abs, then another, and ANOTHER!
Shit!
Chuck was a shooter!
I kept stroking, but now there was just a clear trickle oozing with each stroke.
I was trembling now, too!
Holy shit!
I did it!
I just made a boy cum!
I wanted to cheer, to jump up and down!
God!
That was fun!
The way he shook!
His face!
I looked at Shannon again.
She had mix of confusion, delight and maybe a bit of disgust painted on her cute little face!
I snapped back into character.
“Hahaha! Jeez! Is that it?!” I let go, realizing I now had cum on my fingers.
“Shannon! I just made your boyfriend shoot! Oh my god! Hahaha!” I laughed, but I was watching Shannon intently, trying to guage her reaction.
She was in shock, it seemed.
I stood up and took in the scene.
She was still kneeling on the bed, hands tucked tightly in her lap, staring at Chuck’s naked, cum covered body.
Chuck was panting staring up at the ceiling.
I looked down at his penis, which had deflated and gone limp, rolling to his hip.
It was still a good looking penis though.
I opened the door, then turned back to them.
“I’ll be right back. Chuck, don’t move.” I turned and ran to the bathroom.
I washed my hands, reliving the moment.
I took a moment to wipe my own wetness away.
I then grabbed a rag towel from the laundry.
I made my way back to the room.
I heard Shannon giggling, and stood outside her bedroom, listening.
“Hahaha! Your penis got even smaller!” She said.
“It’s not small!” Chuck declared.
“It’s definitely smaller than it was!” Shannon said.
“Haha! I don’t know. Kylee said it was small, so it must be!”
“It’s not small, Shan! God! I never should have stripped to my boxers for you!” Chuck argued.
“Hehehe! Don’t worry! You’re my boyfriend now, and I like your penis! I’ll still play with it, even if it’s small!” Shannon said.
I found it sweet that she was being supportive.
Then again, it wasn’t like Chuck REALLY had a tiny penis.
I was officially jealous.
At least I was the one to make him shoot.
I was still ahead of Shannon!
Hell, maybe I’d even get to play along WITH her!
At least, until I can get a boy of my own.
I will probably have to tell her at some point, that Chuck doesn’t REALLY have a small penis.
But if it keeps him in line, and will prevent him from cheating on my little sister, so be it.
I heard the garage door open and burst into her room.
Chuck was still laying there, covered in cum, with Shannon kneeling next to him, still smiling at his naked body.
I tossed the rag towel on Chuck.
I then turned and grabbed Chuck’s clothes that I’d tossed in the hall.
“Mom’s home! Hurry and get dressed!” I warned stearnly, tossing his clothes onto the floor in front of Shannon’s bed.
Shannon and Chuck hopped up and began getting him dressed.
I chuckled as his flaccid penis flopped around while he wiped up with the towel and got dressed.
Shannon was also smiling and ogling him as he dressed.
“I’m going to go stall mom.” I said.
“Chuckles,” I addressed Chuck. “Remember, if you do anything to hurt my sister, we’ll tell EVERYONE about your little cock!” I threatened.
“Yeah! Your cock belongs to Kylee and I now!” Shannon said.
My heart fluttered at those words.
Chuck’s cock belonged to US!
My jealousy had turned into a true sisterly bonding moment.
