Tiffany and the First Jack and Jill
Introduction:
Learning about the opposite sex turned out to be fun
“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.
