Tiffany and the First Jack and Jill by MysteryMan611

“Yeah, what is it?”

“Can I come in?”

“Just a sec…” I tucked my semi-hard cock down the leg of

my shorts. “C’mon in Jill.”

My twin sister opened the door a small way and stood there.

“What d’you want?”

“Jack, I got a question.”

“No.”

“You don’t even know what the question is you jerk.”

“If you start with ‘I got a question,’ I know it’s not gonna

be something I wanna do so the answer is no.”

“What if I was gonna ask if you wanted to see Tiffany

naked?”

“Then you would have said so. And I would’ve asked how you

were going to arrange that miracle.”

“So you’d want to?”

“Hell yeah! I suppose you’re gonna say April fool’s now.”

“It’s June, Jack. But I should tell you, she’s willing to

show you hers if you’re willing to show us yours.”

“What? You wanna see my junk?”

“Actually, I can already see your junk,” she said staring at

my shorts. My teenage cock had hardened with the talk of

naked girls and made an appearance at the bottom of my

shorts. Hastily I threw a pillow over my lap.

“Get outta here!”

“Really, Jack, she wants to see you. Actually, she wants to

watch you, well, jack off. She’s never seen one before. And

she’s afraid she never will.”

“All she’s gotta do is offer to give any guy a hand job and

she’ll see all the cocks she wants and then some.”

“Yeah, and then ev’ryone’ll call her a slut. And I’ll still

not have seen one either. Ya want ev’ryone to call your sis

a slut?”

“Why me?”

“Cuz I told her you wouldn’t tell anyone.”

“Exactly what are we talkin’ about here?”

“Tiffany comes over here tonight. Mom and Dad are going out

so we’ll be here alone. She’ll show you her, you know, and

then you jerk off while we watch.”

“You wanna watch me jerk off? That’s kinda weird Jill.”

“I’ve never seen it before. I don’t wanna be all stupid the

first time I give some guy a hand job.”

“I don’t wanna hear about you givin’ hand jobs.”

“Will you do it?”

“She’s gonna get naked?”

“She said she would.”

“She’s gotta sit there naked while I do it.”

“I think she’ll agree to that.”

“And I want to have the opportunity to do it again later.”

“I dunno about that.”

“See what you can do. Now, get outta here so I can do

something.”

“You gonna jerk off now?”

“If I don’t I’m gonna be in some serious pain.”

“Can I see it real quick?”

I stood up throwing my pillow away and dropped my shorts. My

hard cock stood straight out from my body, “Now get outta

here,” I said dismissing her. “Go rub your pussy til you cum

you little tramp.”

Her eyes locked on my cock as she slowly shut the door. I

could see her other hand rubbing between her legs. My sister

was going to go masturbate while thinking about my hard

cock. Weird, right?

It took me all of thirty seconds before I shot my load. I’d

have to work on that before Tiffany came over. Girls don’t

want a guy to cum too quick, especially during sex. Not that

I thought we’d be having sex that night or anything. I

figure I’d be lucky if she really got naked and let me see.

Maybe I could get her to finger herself while I watched, or

she’d let me and maybe I could squeeze those little tits,

lick her nipples, maybe I’d ask her for a blow job. I was

hard again. I spent the next ten minutes edging before

shooting another load as I thought about Tiffany’s lips

around my cock.

I spent the rest of the afternoon doing yard work. The lawn

needed to be mowed, then the clippings raked up and thrown

on the compost. The bushes out front needed trimming. My

sister spent her afternoon moving her sunbed around the yard

avoiding me while I worked. Of course, I got a nice $40 from

dad for the work so I didn’t mind.

Finally finished, I grabbed the sprinkler and snuck it near

Jill’s sunbed. She was snoozing in the sun, her bathing suit

untied to prevent tan lines. Her ass was already golden

bronze. I turned on the water and got a quick view of my

sister’s B-cup tits as she sat up screaming in the cold

water. I made a beeline for the bathroom and locked the door

so I could shower away the sweat and grime in peace.

Drying off I looked in the mirror. Not bad, I thought. The

beginnings of a six pack, no fat anywhere. I didn’t need to

lay out for a tan, my yard work in the neighborhood took

care of that. My cock was of decent size, not porn sized

anyway, but nothing to be embarrassed about. I did decide a

little grooming would be in order before his debut. Not

shaved, but trimmed anyway. I hoped Tiffany kept herself

trimmed. Watching old time porn was such a turn off, all

that hair. I wasn’t a big fan of bald pussy, but it was

better than a huge bush. Short trimmed hair, that was what I

liked.

My cock began to swell as I trimmed aroud it. I wondered if

Tiffany’ll want to touch it. Would she think about it the

next time she touched herself? Maybe she’d like something to

remember it by. I could give her a picture to take home.

Maybe she’s let me take a picture of her as well. My

grooming done, my cock had swollen to about it’s full

length, though still too heavy to stand before getting fully

hard.

I put one foot on the countertop and grabbed my cell phone.

I took a picture in the mirror from my six pack down. I took

my cock in hand and stroked it a couple of times getting it

to full mast. I snapped another shot showing its full

hardness. Next, I pointed it straight at the mirror and took

a shot that would be great for a POV for a girl giving a

blow job. Finally, I stroked myself until I shot a load at

the mirror. I stood there and took a picture of the cum

sliding down the glass before cleaning up.

Back in my room, I put on some loose fitting shorts before

transferring the pictures to my computer. I printed them out

on one glossy page and then deleted the evidence. These were

for Tiffany. No need to save them for anyone else to find.

The rest of the day seemed to drag on forever. When it

seemed like the day would never end there was a knock on my

door. “Yeah?”

“Hey champ,” my dad said as he opened the door. “Your mom

and I are about to head out. Pizza is on the way. Money is

on the counter. We should be back by one. Don’t forget, Jill

has her friend Tiffany coming over tonight. Don’t give’m too

hard a time. I don’t wanna hear about it tomorrow.”

I nearly started laughing. In fact I don’t know how I kept

from exploding. “Promise, Dad, I won’t bother’em.”

“Do me a favor, put on a shirt before you go down to eat.

You’re sister’ll yell and scream about how you’re

embarrassing her in front of her friends. She’s already

complained to your mom about the sprinkler incident.”

“You realize you and mom let her get away with murder?”

“Yeah, well you may be the same age, but you’re her big

brother. Be nice.”

“Honey, c’mon, we’ll be late,” my mom said poking her head

in. “Good night Jack. Be good. Have fun tonight.”

“You, too, mom. See you tomorrow.” She continued down the

hallway.

The doorbell rang. “That’s probably the pizza. Put on a

shirt and come downstairs.”

I grabbed a polo shirt and pulled it on, leaving it

unbuttoned. “Jill!” my mother yelled. “Pizza’s here! And so

is Tiffany! Your father ad I are leaving!”

I heard the front door close twice. We were alone. It

wouldn’t be long now. I’d be seeing my first live pussy and

jerking off in front of Tiffany and my sister. I could feel

my member slowly swelling in my shorts. I loved wearing

these shorts and I hate wearing underwear. I guess I’m sort

of an exhibitionist at heart. Whenever I get hard he puts on

a show for anyone looking his direction. Pizza in the den

was going to be a fun start to the evening.

When I got downstairs I was alone. Tiffany had evidently

joined my sister in her room. I grabbed the pizza boxes and

a two liter bottle of coke before heading to the den. I made

a second trip grabbing cups, ice, and a surprise, a bottle

of Crown Royal I had stashed. Before I yelled for the girls

I made some weak Crown and cokes and situated myself on the

couch such that they would probably sit on the floor across

from me while we ate on the coffee table.

“Come and get it girls, before it gets cold!” I yelled.

Shortly later I could hear them tramping down the stairs.

“What’d we get?”

“Half veggie, half cheese and half supreme, half pepperoni

and jalapeno.”

“You know which one’s yours then.”

“Yep, already started,” I said stretching out on the couch.

Like I figured they sat across from me on the floor.

Tiffany looked hot. Not too much makeup. Tank top, No

visible bra. Loose leg shorts. Her tan was as dark as my

sister’s. Her blonde hair shone bright in the den lights.

Her nipples, my god her nipples, were visibly poking the

thin material of her shirt. Guess she likes showing off too.

My cock appreciated the preview and began to fill ready to

make his appearance.

Jill took a drink and spluttered, “What did you put in

this?”

“Just a little Crown.”

“Where did you get Crown? If you raided Dad’s liquor cabinet

he’ll know.”

“Don’t worry,” I said producing the bottle. “I’ve had this

for a while. You don’t mind, do you Tiff?”

“No,” she said taking a big gulp of liquid courage. “I like

it. I don’t get to have any at home but we had some at

Shannon’s last time.”

“Anytime you want some, you know I’ve got what you want.”

I sat up to pour another drink for myself. I spread my legs

and felt fresh air touch the head of my cock as it lay there

along my leg. If the girls looked up they’d see it.

“Really Jack? I thought we’d eat dinner before the show.”

“What’s wrong now Jill?” I asked.

“Oh my,” responded Tiffany seeing what Jill was pointing at.

“Oh, sorry.” I put a pillow on my lap which did nothing to

hide the snake poking his head out the leg of my shorts. the

girls still had a full view.

“It’s still there Jack.”

“What do you want me to do about it? Tiffany’s sitting there

with her nipples pointing like erasers. I might as well take

these shorts off now!”

“No Jack, that’s fine. Just try and keep him under control

until we’re done eating.”

I watched Tiffany squirm as she sat. I caught her looking up

my shorts several times. Her free hand kept reaching for the

napkin in her lap that wasn’t there. Jill too seemed

affected. Her nipples were now poking against the material

of her shirt.

Before we finished eating I poured a second drink for each

of the girls, a little stronger this time and a third for

myself, a little weaker.

“What d’you think girls? Want to do this down here? Or would

you rather go to one of our rooms?”

“I don’t know if I can do it down here. what if your parents

came home early?”

“Ok, we can use Jill’s room or mine.”

“Let’s use yours. I don’t think I could explain the musky

smell to mom and dad.”

“What?”

“You must be used to it. Your room has a scent. When you’ve

been busy.”

“And nobody ever told me?!?”

“I always thought you knew.”

“Is it bad?”

“No, it just smells like, well, manly.” I was not amused.

“Go on up. Tiff and I’ll clean this up. We’ll be up there in

ten minutes.”

I climbed the stairs to my room. I opened the door and

sniffed. Nothing. Maybe I was used to it. I turned my desk

chair around facing the bed. I only had one chair so I guess

I’d let them have the bed to watch from. I’d jerked off in

this chair quite a few times watching porn on my computer.

Now I’d have porn on my bed to jerk off to.

What an opportunity, I grabbed my SLR camera and pointed it

at my bed it was always sitting on my desk so it shouldn’t

arouse any suspicion. I set it for video and hit the start

button. Seconds later there was a knock on my door. I sat

back on my captain’s chair and draped a leg over one arm.

“Come in.”

Jill came in first and shut the door behind her. “Ok, she’s

agreed to get naked and stay naked until you finish. You

can’t touch her while she’s naked.” she leaned close and

whispered, “She just told me she’s so horny right now she

wants to jump your bones.” She climbed on my bed and

stretched out like a cat. “You can come in now Tiff.”

Music came from the hallway and the door opened. Tiffany

strutted in, in time with the music. She was better than any

stripper I’d seen online. She was wearing a colorful short

silk robe which clung to her body. She came over to me and

undulated her body erotically before leaning in and kissing

me lightly on the lips. I nearly reached out and pulled her

into my arms but held back.

She moved away and turned her back towards me. She opened

the robe slightly and it slipped from her shoulders. She

turned back to me and her hands held the robe to her

breasts. She turned away and bent forwards lifting her robe,

exposing her ass and just a hint of the space between her

legs. As the music climaxed she turned to me again and held

the robe open, her body there for me to drink in. Her pert

breasts topped with those delicious nipples I’d seen the

hints of earlier. Her short, downy hair covered pussy, just

like I’d imagined.

My cock was harder than I could ever remember. It was longer

than I’d ever seen. It strained as I groaned. It pushed the

leg of my shorts aside and stood proud in front of Tiffany

and my sister.

Tiffany sat on my bed. She raised one foot and set it to her

side. This opened her legs and I could see the warm moist

hole that craved my hard cock. The same place my hard cock

craved to be. She was wet and horny. She slid a finger

between the folds of her wet pussy, her head leaned back and

she moaned. finally she stretched her body out on my bed,

turned on her side, her leg propped up keeping her fully

open to my gaze.

I wheeled my chair close to my bed. I slid my shorts over my

erection and down my legs, never taking my eyes off Tiffany.

I propped both feet on the edge of my bed and spread my legs

wide. giving the girls a great view of my cock and balls.

Precum oozed from the tip. Normally I would grab a little

baby oil to facilitate my fun but not today. My copious

precum fluids gave me plety of lubrication. I spread it all

up and down my shaft and over the head. I moaned at the

sensations I was feeling. I wanted to close my eyes and

fantasize as I often did but my fantasy was in front of me.

Tiffany slid her fingers over her fur covered mound and

through her silky folds. Another hand, my sister’s hand

cupped her breast as she watched from over Tiffany’s

shoulder. Tiffany moaned. I moaned. Jill moaned.

My hand feverishly worked up and down my steel hard shaft. I

wouldn’t last long. I couldn’t last long. Even though I’d

jerked off several times earlier my body’s senses were in

overload. I could think only of the naked girl in front of

me and how I wanted her to be part of what was happening to

me.

“Cum for me Tiff,” I pleaded. “Let me see you cum.”

“Yes, Tiff, let’s show my brother how you cum. Then he’ll

splash his man cum all over your naked body.” My sister

reached down between Tiffany’s legs and rubbed her mound

while Tiffany’s own fingers lightly probed her virgin pussy.

Her hips rocked back and forth and she moaned loudly.

“I’m cumming. Oh god, I’m cumming. cum for my Jack, shoot

your man cum all over me. Oh god, oh g-g-god! Cum Jack, cum

for me!”

I stood up and started furiously sliding my hand up and down

my steel rod. The purple head topping my cock looked like it

was going to explode. My body felt like it couldn’t take

anymore. Finally my balls contracted ad I began to shoot

long streams of cum across Tiffany’s chest, then her belly,

then between her legs, coating her and my sister’s fevered

fingers.

Finally I sat back in my chair, exhausted.

“Oh god Jack, that was the best ever.”

“I hear it gets better.”

“How, how can it possibly get better than that?”

“For me? For someone to do it to me. For you? For me to do

it to you. For us? To do it together.”

“And then what?”

“And then we try something new. I can hardly wait to taste

your hot wet pussy.”

“What if I’m not ready for that?”

“Then maybe we just do this again.”

“You would be ok with just this?”

“More would be nice, but if I’m doing anything I’m happy.”

“What about a party?”

“What? with more people?”

“Yeah, you bring a couple of your guy friends and we bring

another girl. Guys jack off, girls jill off. It’s called a

jack and jill party.. Not quite as intimate as this but

kinda crazy.”

“You have some people in mind?”

“Your sister likes Robert. My sister likes James. You think

they’d like to join us?”

“I think they’d go crazy for the idea if the ‘no touching’

rule wasn’t there.”

“That’s the thing, it’s not sex if there’s no touching.”

“But my sister was touching you.”

“That’s different.”

“How?”

“Cuz we’re both girls. It’s still just jillin’. A guy

touches me and he’s gonna want to do more.”

“I was just watching and believe me I wanna do more. I want

to feel your tits, suck on your beautiful nipples, run my

fingers between the folds of your pussy. I want you to touch

my cock, carress my balls, stroke me til I cum. I bet you

couldn’t even tell if it was me or Jill doing it to you.

Anyway, if there are limits to touching it would be easier

than no touching at all.”

“I bet I could tell,” said Jill.

“Tell what?”

“If you both sucked my nipples I could tell which was

which.”

“And if you can’t?”

“If I can’t we do one thing for you today and we come up

with a list of touching rules.”

“Ok, we need a blindfold. Jill sit in the chair and take

your shirt off.”

I grabbed a muffler from my closet and covered my sisters

eyes. “We’re gonna spin you around for a second. then we’ll

take turns sucking your nipples. When you think you know who

it is, say it. Three out of five guesses wins.”

This was so cool. Jill was sitting topless in my desk chair.

Tiffany was across from me still naked. I was standing

around with my junk hanging out as well. How could I fool my

sister into thinking I was Tiffany. How does Tiffany do it?

I pointed to her and mimed for her to go first.

“Okay you two, tongues and lips, no hands. I’m sure I’d

recognize a guys hands.”

We spun the chair around clockwise a few times and then

counterclockwise. We stopped the chair and Tiffany leaned in

as I watched. My sister’s breasts rose and fell with her

breath. I just realized I was gonna lick my sister’s

nipples, suck on her breast, make her feel good. And she

wanted me to do it.

Tiffany was gentle with Jill. she flicked the nipple with

her tongue then carressed the areola as well. She took the

whole breast in her mouth and sucked.

“Tiffany, definitely Tiffany.”

I held my finger to my mouth in the universal “shhh” sign. I

started the chair spinning again and stopped it shortly. I

directed Tiffany to go again. she did the same to the other

breast.

“Jack, you’re good at this too. I’m sure that was Jack.”

We spun the chair. This time I leaned in. Jill’s breast was

still wet with Tiffany’s saliva. I blew softly and watched

as the papillae stood up. I touched the nipple with the tip

of my tongue. My first time touching a girl’s breast. I

flicked the nipple with my tongue. I opned my mouth in a

small “O” shape and took the breast into my mouth. I played

with the nipple with my tongue while applying suction.

“Keep that up Tiff and I’m gonna cum!”

We spun the chair again. I pointed at Tiffany.

She was gentle once more. I could tell she’d done this

enough to know what my sister liked.

“Jack, quit trying to be a woman.”

“That’s three out of five I said taking the blindfold off.”

“What I got three out of the first four?”

“No, you missed three out of four.”

“Which one did I get right?”

“The first.”

“That means Jack was only the third time? That time was

amazing. You know how to use your tongue Jack. you need to

let him show you Tiff.”

“Later. Okay Jack, what do you want?”

“Two things, first, I’ll take the blindfold and see if I can

tell which of you is touching me until I shoot. And then I

want to watch the two of you. Or rather I want to watch you,

Tiffany, give my sister something she hasn’t had yet today.”

I sat back on the bed and tied the blindfold on. “Feel free

to use your hands however you want. You’re the same size so

I doubt I could tell which is which.”

I felt four hands sliding up and down my body as I lay

there. I was still hard from earlier. A pair of lips kissed

my nipple while a soft hand cupped my balls. My hips lifted

from the bed anticipating, no, begging them to touch my

shaft. Another kiss, this time to my other nipple. Lips

brushed across my lips, a tongue touched my lips. Too late I

opened my mouth, whoever it had been had moved on.

Baby oil drizzled on my chest, my abdomen, and my elongated

cock. Hands smeared my body. Locked fingers finally found my

hardness. Together, I could tell they were working together,

their hands slid up and down. A nipple found its way to my

lips. And it was gone replaced by a pair of lips pressed

against mine. This time I responded. Our tongues touched and

an arc of electricity joined us as one. Another mouth took

my nipple back in her mouth and nibbled lightly. The hands

quickened their pace stroking up and down. I reached out and

felt flesh.

Yes, that was Tiffany on my right. My fingers slid between

her legs, between her lips. My thumb rubbed her button. I

could feel her body responding. A hand grabbed my other hand

and placed it between another pair of legs. Now I was

confused. Which was Tiffany and which was Jill. It didn’t

matter. I slid my fingers between both sets of nether lips,

careful of their unbroken hymens. My thumbs rubbed them as

they stroked me. Their lips switched places. Now I was

furiously kissing the other, our tongues dancing.

I felt my body building towards its imminent explosion.

Never before had it felt so good. I was thrusting with my

hips as their hands slid up and down. Their bodies were both

reacting wildly to my probing fingers. Soon, soon, my body

spasmed! I went rigid as I felt a shower of cum land on my

stomach and chest.

Exhausted by pleasure I collapsed. My fingers continued

their work though and I felt the flood of juices as the girl

on my right had her silent orgasm while our lips were locked

together. She slid off my fingers and embraced me as the

girl on my left took her spot, our tongues dancing as my

fingers danced between her legs. She sat back and guided my

fingers with her own.

“I think you’re right,” said Tiffany between breaths,

“Touching is good.”

Tiffany removed my blindfold and together we watched my

sister as my fingers brought her to a momentous orgasm. When

she finally collapsed the three of us lay there together

while we regained our strength.

“Think there’s any pizza left?” I asked.

Both girls punched me.