Tiffany and the First Jack and Jill
Introduction:
Learning about the opposite sex turned out to be fun
âYeah, what is it?â
âCan I come in?â
âJust a secâŠâ I tucked my semi-hard cock down the leg of
my shorts. âCâmon in Jill.â
My twin sister opened the door a small way and stood there.
âWhat dâyou want?â
âJack, I got a question.â
âNo.â
âYou donât even know what the question is you jerk.â
âIf you start with âI got a question,â I know itâs not gonna
be something I wanna do so the answer is no.â
âWhat if I was gonna ask if you wanted to see Tiffany
naked?â
âThen you would have said so. And I wouldâve asked how you
were going to arrange that miracle.â
âSo youâd want to?â
âHell yeah! I suppose youâre gonna say April foolâs now.â
âItâs June, Jack. But I should tell you, sheâs willing to
show you hers if youâre willing to show us yours.â
âWhat? You wanna see my junk?â
âActually, I can already see your junk,â 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.
âGet outta here!â
âReally, Jack, she wants to see you. Actually, she wants to
watch you, well, jack off. Sheâs never seen one before. And
sheâs afraid she never will.â
âAll sheâs gotta do is offer to give any guy a hand job and
sheâll see all the cocks she wants and then some.â
âYeah, and then evâryoneâll call her a slut. And Iâll still
not have seen one either. Ya want evâryone to call your sis
a slut?â
âWhy me?â
âCuz I told her you wouldnât tell anyone.â
âExactly what are we talkinâ about here?â
âTiffany comes over here tonight. Mom and Dad are going out
so weâll be here alone. Sheâll show you her, you know, and
then you jerk off while we watch.â
âYou wanna watch me jerk off? Thatâs kinda weird Jill.â
âIâve never seen it before. I donât wanna be all stupid the
first time I give some guy a hand job.â
âI donât wanna hear about you givinâ hand jobs.â
âWill you do it?â
âSheâs gonna get naked?â
âShe said she would.â
âSheâs gotta sit there naked while I do it.â
âI think sheâll agree to that.â
âAnd I want to have the opportunity to do it again later.â
âI dunno about that.â
âSee what you can do. Now, get outta here so I can do
something.â
âYou gonna jerk off now?â
âIf I donât Iâm gonna be in some serious pain.â
âCan I see it real quick?â
I stood up throwing my pillow away and dropped my shorts. My
hard cock stood straight out from my body, âNow get outta
here,â I said dismissing her. âGo rub your pussy til you cum
you little tramp.â
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. Iâd
have to work on that before Tiffany came over. Girls donât
want a guy to cum too quick, especially during sex. Not that
I thought weâd be having sex that night or anything. I
figure Iâd be lucky if she really got naked and let me see.
Maybe I could get her to finger herself while I watched, or
sheâd let me and maybe I could squeeze those little tits,
lick her nipples, maybe Iâd 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 Tiffanyâs 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 didnât mind.
Finally finished, I grabbed the sprinkler and snuck it near
Jillâs 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
sisterâs 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 didnât 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 wasnât 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
Tiffanyâll want to touch it. Would she think about it the
next time she touched herself? Maybe sheâd like something to
remember it by. I could give her a picture to take home.
Maybe sheâs let me take a picture of her as well. My
grooming done, my cock had swollen to about itâs 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. âYeah?â
âHey champ,â my dad said as he opened the door. âYour mom
and I are about to head out. Pizza is on the way. Money is
on the counter. We should be back by one. Donât forget, Jill
has her friend Tiffany coming over tonight. Donât giveâm too
hard a time. I donât wanna hear about it tomorrow.â
I nearly started laughing. In fact I donât know how I kept
from exploding. âPromise, Dad, I wonât botherâem.â
âDo me a favor, put on a shirt before you go down to eat.
Youâre sisterâll yell and scream about how youâre
embarrassing her in front of her friends. Sheâs already
complained to your mom about the sprinkler incident.â
âYou realize you and mom let her get away with murder?â
âYeah, well you may be the same age, but youâre her big
brother. Be nice.â
âHoney, câmon, weâll be late,â my mom said poking her head
in. âGood night Jack. Be good. Have fun tonight.â
âYou, too, mom. See you tomorrow.â She continued down the
hallway.
The doorbell rang. âThatâs probably the pizza. Put on a
shirt and come downstairs.â
I grabbed a polo shirt and pulled it on, leaving it
unbuttoned. âJill!â my mother yelled. âPizzaâs here! And so
is Tiffany! Your father ad I are leaving!â
I heard the front door close twice. We were alone. It
wouldnât be long now. Iâd 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 Iâm 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.
âCome and get it girls, before it gets cold!â I yelled.
Shortly later I could hear them tramping down the stairs.
âWhatâd we get?â
âHalf veggie, half cheese and half supreme, half pepperoni
and jalapeno.â
âYou know which oneâs yours then.â
âYep, already started,â 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
sisterâs. 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, âWhat did you put in
this?â
âJust a little Crown.â
âWhere did you get Crown? If you raided Dadâs liquor cabinet
heâll know.â
âDonât worry,â I said producing the bottle. âIâve had this
for a while. You donât mind, do you Tiff?â
âNo,â she said taking a big gulp of liquid courage. âI like
it. I donât get to have any at home but we had some at
Shannonâs last time.â
âAnytime you want some, you know Iâve got what you want.â
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 theyâd see it.
âReally Jack? I thought weâd eat dinner before the show.â
âWhatâs wrong now Jill?â I asked.
âOh my,â responded Tiffany seeing what Jill was pointing at.
âOh, sorry.â 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.
âItâs still there Jack.â
âWhat do you want me to do about it? Tiffanyâs sitting there
with her nipples pointing like erasers. I might as well take
these shorts off now!â
âNo Jack, thatâs fine. Just try and keep him under control
until weâre done eating.â
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 wasnât 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.
âWhat dâyou think girls? Want to do this down here? Or would
you rather go to one of our rooms?â
âI donât know if I can do it down here. what if your parents
came home early?â
âOk, we can use Jillâs room or mine.â
âLetâs use yours. I donât think I could explain the musky
smell to mom and dad.â
âWhat?â
âYou must be used to it. Your room has a scent. When youâve
been busy.â
âAnd nobody ever told me?!?â
âI always thought you knew.â
âIs it bad?â
âNo, it just smells like, well, manly.â I was not amused.
âGo on up. Tiff and Iâll clean this up. Weâll be up there in
ten minutes.â
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
Iâd let them have the bed to watch from. Iâd jerked off in
this chair quite a few times watching porn on my computer.
Now Iâd 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 shouldnât
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 captainâs chair and draped a leg over one arm.
âCome in.â
Jill came in first and shut the door behind her. âOk, sheâs
agreed to get naked and stay naked until you finish. You
canât touch her while sheâs naked.â she leaned close and
whispered, âShe just told me sheâs so horny right now she
wants to jump your bones.â She climbed on my bed and
stretched out like a cat. âYou can come in now Tiff.â
Music came from the hallway and the door opened. Tiffany
strutted in, in time with the music. She was better than any
stripper Iâd 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 Iâd seen the
hints of earlier. Her short, downy hair covered pussy, just
like Iâd imagined.
My cock was harder than I could ever remember. It was longer
than Iâd 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 sisterâs hand
cupped her breast as she watched from over Tiffanyâs
shoulder. Tiffany moaned. I moaned. Jill moaned.
My hand feverishly worked up and down my steel hard shaft. I
wouldnât last long. I couldnât last long. Even though Iâd
jerked off several times earlier my bodyâs 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.
âCum for me Tiff,â I pleaded. âLet me see you cum.â
âYes, Tiff, letâs show my brother how you cum. Then heâll
splash his man cum all over your naked body.â My sister
reached down between Tiffanyâs legs and rubbed her mound
while Tiffanyâs own fingers lightly probed her virgin pussy.
Her hips rocked back and forth and she moaned loudly.
âIâm cumming. Oh god, Iâm cumming. cum for my Jack, shoot
your man cum all over me. Oh god, oh g-g-god! Cum Jack, cum
for me!â
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 couldnât take
anymore. Finally my balls contracted ad I began to shoot
long streams of cum across Tiffanyâs chest, then her belly,
then between her legs, coating her and my sisterâs fevered
fingers.
Finally I sat back in my chair, exhausted.
âOh god Jack, that was the best ever.â
âI hear it gets better.â
âHow, how can it possibly get better than that?â
âFor me? For someone to do it to me. For you? For me to do
it to you. For us? To do it together.â
âAnd then what?â
âAnd then we try something new. I can hardly wait to taste
your hot wet pussy.â
âWhat if Iâm not ready for that?â
âThen maybe we just do this again.â
âYou would be ok with just this?â
âMore would be nice, but if Iâm doing anything Iâm happy.â
âWhat about a party?â
âWhat? with more people?â
âYeah, you bring a couple of your guy friends and we bring
another girl. Guys jack off, girls jill off. Itâs called a
jack and jill party.. Not quite as intimate as this but
kinda crazy.â
âYou have some people in mind?â
âYour sister likes Robert. My sister likes James. You think
theyâd like to join us?â
âI think theyâd go crazy for the idea if the âno touchingâ
rule wasnât there.â
âThatâs the thing, itâs not sex if thereâs no touching.â
âBut my sister was touching you.â
âThatâs different.â
âHow?â
âCuz weâre both girls. Itâs still just jillinâ. A guy
touches me and heâs gonna want to do more.â
âI 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
couldnât 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.â
âI bet I could tell,â said Jill.
âTell what?â
âIf you both sucked my nipples I could tell which was
which.â
âAnd if you canât?â
âIf I canât we do one thing for you today and we come up
with a list of touching rules.â
âOk, we need a blindfold. Jill sit in the chair and take
your shirt off.â
I grabbed a muffler from my closet and covered my sisters
eyes. âWeâre gonna spin you around for a second. then weâll
take turns sucking your nipples. When you think you know who
it is, say it. Three out of five guesses wins.â
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.
âOkay you two, tongues and lips, no hands. Iâm sure Iâd
recognize a guys hands.â
We spun the chair around clockwise a few times and then
counterclockwise. We stopped the chair and Tiffany leaned in
as I watched. My sisterâs breasts rose and fell with her
breath. I just realized I was gonna lick my sisterâs
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.
âTiffany, definitely Tiffany.â
I held my finger to my mouth in the universal âshhhâ 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.
âJack, youâre good at this too. Iâm sure that was Jack.â
We spun the chair. This time I leaned in. Jillâs breast was
still wet with Tiffanyâs 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 girlâs breast. I
flicked the nipple with my tongue. I opned my mouth in a
small âOâ shape and took the breast into my mouth. I played
with the nipple with my tongue while applying suction.
âKeep that up Tiff and Iâm gonna cum!â
We spun the chair again. I pointed at Tiffany.
She was gentle once more. I could tell sheâd done this
enough to know what my sister liked.
âJack, quit trying to be a woman.â
âThatâs three out of five I said taking the blindfold off.â
âWhat I got three out of the first four?â
âNo, you missed three out of four.â
âWhich one did I get right?â
âThe first.â
âThat 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.â
âLater. Okay Jack, what do you want?â
âTwo things, first, Iâll 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 hasnât had yet today.â
I sat back on the bed and tied the blindfold on. âFeel free
to use your hands however you want. Youâre the same size so
I doubt I could tell which is which.â
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 didnât
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.
âI think youâre right,â said Tiffany between breaths,
âTouching is good.â
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.
âThink thereâs any pizza left?â I asked.
Both girls punched me.