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You are here: Home / Adult sex stories / Tiffany and the First Jack and Jill by MysteryMan611

Tiffany and the First Jack and Jill by MysteryMan611

by MysteryMan611 June 27, 2023 Leave a Comment

A literotic sexstories: 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

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