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Andrew Roller Presents
NAUGHTY NAKED DREAMGIRLS
in
JACK and JILL
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Chapter One
Jill was just tidying up the cabin when Jack came back from the
cockpit.
"Nice flight," Jill smiled brightly. Jack always looked quite dashing
in his pilot's uniform.
"I see you survived the passengers," Jack murmured.
"Barely," Jill sighed. "There were enough crying babies on this plane
to qualify it as a maternity ward."
"I finally got some information on that exclusive club," Jack
confided.
"Really?" Jill exclaimed. For months now they had been hearing
rumors of a private resort for pilots and stewardesses. Membership was
by invitation only.
"They've got some place, or so I understand," Jack said. "Steam
rooms, whirlpool baths, indoor pools with slides...but they don't just take
individuals. You've got to sign up with another person of the opposite sex.
To keep out lonely hearts, I guess."
"I'll sign up with you!" Jill beamed. She had been dying to get away
from the grind of being an inflight hostess.
"Well, alright!" Jack agreed. "Get your stuff and come on, then. I've
got an appointment with a lady there in half an hour."
Jill and Jack were riding toward Waikiki several minutes later,
eyeing a gaggle of no-frills tourists as they clambered onto a city bus.
"Who would you have asked if I'd said no?" Jill smiled. She wondered
if she'd been the first stew Jack had asked to accompany him.
"Nobody," Jack said. "I'd have just tied you up and bundled you into
the nearest taxi." Jill gave Jack a light slap.
"Oh, you!" Jill cried mischievously. "I didn't know you liked me that
much."
"Well, now you do," Jack replied, and rested his hand on her bare
thigh.
Jack was stroking the inside of Jill's thigh, beneath her miniskirt,
when the taxi pulled up the driveway of the Waikiki Hilton. Jill, who had
been trying to suppress a squeal for the last five miles, breathed a sigh of
relief as Jack took his hand from her and rummaged for his wallet. A
moment later both of them had been escorted out of the cab by the hotel's
door man and were walking hand in hand toward the elevators.
At the appropriate floor Jack and Jill exited and headed toward the
suite number Jack had been given over the phone. After a moment of
looking they found it, and knocked on the door.
A girl no more than 20 opened the door and admitted them with a
smile. She wore a beautiful jacket with a deep decolletage with a
matching knee length skirt that hugged her hips. A pearl choker sparkled
about her neck. The girl introduced herself as Mindy and led Jack and Jill
into another room where a second girl, barely older than the first, rose
and lightly shook hands with the couple.
Jill was by now feeling quite comfortable, as she was the same age
as the girls whose job it apparently was to screen applicants to the
private club. The girl behind the desk introduced herself as Diane, and she
and Jill immediately fell into a friendly female conversation.
Diane did not dwell long in the realm of small talk, however. With
smooth professionalism she made a seamless transition into the reason
for the couple's visit. At this point Jack was deftly brought into the
conversation, and he related that he and Jill were looking for a place
where they could relax and blow off steam.
"We're a very closely knit group," Diane said after pointing out the
club's various facilities and the yearly dues, both of which were
substantial. "Not only must you be either a pilot or a stewardess, but you
must be attractive as well." Jill swallowed at this, then silently berated
herself for doing so. She was just as attractive as the sultry Diane,
although she was not wearing a dress that displayed her cleavage quite so
prominently. Jill glanced at Jack, and noticed that his eyes were still
fixed more on Diane's bust than her face as he conversed.
"Nudity is quite common on the club grounds," Diane went on. "Do
either of you think you would have a problem with that?" Jill and Jack sat
like mute stones for a second, then both nodded that they would not.
"Good, then let's see what you've got," Diane commanded. Jill and Jack,
seated on separate chairs placed next to one another, exchanged puzzled
glances. Diane rose from her chair behind the desk.
"Lower your pants, please," Diane said pointedly to Jack.
"You want me to undress?!" Jack cried.
"Have you ever been in the military?" Diane asked.
"Sure, that's where I learned to fly jets," Jack said.
"And what were you required to do before you were admitted?" Diane
said, her bust looming ever larger as she strode over to where Jack was
seated.
"Oh. Yeah. Strip naked...bend over...," Jack said, beginning to catch
Diane's drift.
"Well, I don't need you to get naked or bend over," Diane said. "But if
you're going to parade your penis around the club it's got to be the right
size."
"Uh, I dunno...it might be too big," Jack said. He unzipped himself,
remarking silently that while he had not expected to display his manhood
before two gorgeous females he certainly had little objection to it.
"Largeness is not a problem," Diane grinned. "At 25 I expect you'll
pop out fully hard," she added as she watched Jack reach inside his pants
for his prong. Sure enough, Jack's rod came out stiff and throbbing. Diane
reached down and stroked it several times to make sure it was at its
maximum extension. Jill eyed her jealously. Then Diane produced a cloth
tape measure and measured Jack's dick. Mindy appeared and wrote down
Jack's size on a pad.
"Mmm, ten inches," Diane breathed. "Now open your shirt so I can see
if your dick matches your chest." Jack, his penis still wobbling nakedly
from the opening in his trousers, began undoing the buttons of his jacket.
Diane loosened his tie and began on the buttons of his shirt. Mindy, seeing
that Jill was as yet still unexposed, walked over to her and, with a smile,
lifted up her skirt.
"Please pull down your panties a little, so Diane can inspect your
pussy," Mindy said softly to Jill.
"But I don't want to," Jill protested.
"I felt scared too at first, when I joined," Mindy said. "But the only
way to really have fun is to play without your clothes on."
"Did you agree to come with me?" Jack asked of Jill over his
shoulder as Diane bared his chest.
"Yes," Jill said testily. Perhaps out of envy of Diane's intimate
proximity to Jack, she tugged on her panties, pulling them down. The
panties, perhaps as reluctant as Diane herself, separated from her crotch
only after the waistband was already halfway down her thighs. Jill,
having raised her bottom slightly, plopped it back down on the chair.
Mindy touched her pubic hair and twirled a finger through its curls.
"How is she?" Diane, pleasantly preoccupied with Jack, asked Mindy.
"Small...tight...neat little pubic thatch," Mindy reported. "Spread your
legs a bit more, please," Mindy said to Jill. The girl hesitated for a
moment, then obeyed. Mindy touched a finger to Jill's slender labia lips
and then intruded inside, up to her first knuckle.
"Jack!" Jill cried, squirming in her chair but otherwise still dutifully
holding up her skirt. Jack reached over and stroked Jill's long blonde mane
with his hand. Diane kissed his chest and then knelt and introduced the tip
of his penis to her lips. She ran her tongue around the flange of Jack's
penis as she dipped a hand into his trousers to squeeze his balls.
"Mmm, nice and tight," Diane remarked of Jack's testicles. "And full.
Do you think you can save it until tomorrow night? I want more time to
admire your loaded balls."
"You can admire them now all you want," Jack said. Beside him Jill,
despite the finger up her pussy, appeared most concerned with the
intimacy between Diane and Jack.
"No, any more now would be unprofessional," Diane said, and rose,
releasing him. She turned to Jill, who sat looking glum and afraid as
Mindy withdrew her digit from her and popped it into her mouth.
"Tasty!" Mindy remarked. Diane gave her a scolding glare.
"I must see your breasts as well dear," Diane said matter-of-factly
to Jill. Mindy, meanwhile, skipped over to Jack.
"I want to see your great rod too," Mindy exclaimed. She ran her wet
finger around the crown of Jack's penis.
"Don't make him come!" Diane warned, glancing back over her
shoulder as she undid Jill's blouse for her.
"I won't," Mindy said, letting go of Jack's dick. "But I'd like to." She
smiled at Jack. Then she leaned forward and pecked Jack on the cheek.
The swell of the upper half of her bosoms was not lost on Jack. As Mindy's
lips touched Jack's cheek he lightly squeezed her right breast.
"Put your dick away," Diane told Jack.
"Here, I'll help you pack this monster away," Mindy said brightly to
Jack of his dick. She knelt down and began struggling to get his fully
erect penis back inside his pants.
Diane's fingers pulled apart Jill's blouse, revealing a frilly white bra
beneath.
"So modest," Diane muttered of Jill. She reached around behind Jill's
back and fought with the clasp of her bra. Her eyes glanced down at Jill's
little United vest, which lay in a heap about her waist. "Your vest gives
you support, you know. You don't really need a bra," Diane said to Jill.
"I-I guess so," Jill said. Diane released the clasp and Jill's
restrained breasts gave a visible surge forward. Diane smoothed Jill's bra
straps off her shoulders, revealing her creamy white mammaries.
"You'll be able to get an all-over tan at the club...if you want one,"
Diane said to Jill. She cupped Jill's white breasts in her hands and
weighed their fullness. "Mmm, I'm jealous," Diane said of Jill's breasts. "I
wonder how big these are?" Diane got out her cloth measuring tape again
(which she kept in her bust) and ran it around Jill's breasts, abjuring the
girl to sit up straight.
"Gosh! You and I are the exact same size!" Diane exclaimed to Jill.
"We can trade bras."
"I thought you didn't wear one?" Jill, still slightly sullen, asked.
"I don't in public," Diane replied. "But I do in private...without a
blouse." Diane leaned forward and kissed Jill lightly on the lips. "Now get
dressed. I've got another appointment due any minute."
"Unh! That was tough!" Mindy exclaimed, wiping her forehead with
the back of her palm. "But fun." She beamed at Jack, and at the bulge in
his zippered up trousers where the penis she had finally managed to get
back under cover lay.
"Our next meeting is tomorrow night," Diane informed Jack and Jill
several minutes later as Mindy helped Jill close up the last buttons on her
vest. "Dress formally, but not stiffly. As newcomers you're expected to
show up for cocktails so everyone can get to know you. Cocktails are at 4,
to give us time for some dancing and games before dinner. After dinner
you'll each be required to select a small ritual to undergo for admission to
the club."
"A ritual, eh?" Jack said. "How's fucking you sound?"
"You'll be given several choices, but laying me is not one of them,"
Diane said smartly. "However, I beg you not to release that heavy load of
yours until tomorrow night."
"That's a tough request," Jack said. "But for you, I'll do it." Had Jack
known what Diane had in mind for his poor balls he would have
masturbated on the spot.
Several minutes later Jack and Jill were walking briskly, hand in
hand, along the busy sidewalks of Waikiki toward a restaurant Jack had
suggested. The close observer would have noticed that their clothes were
slightly disheveled, and their stride somewhat stiffer than the lolling gait
of the natives and tourists around them.
"Well, what did you think?" Jack asked Jill. "I swear I didn't know
they were going to undress us."
"If those girls weren't my age I would have gone screaming out of
there," Jill remarked. "But I felt embarrassed. They seemed so sure of
themselves...so sophisticated...so worldly...even that silly girl Mindy."
"Don't feel bad," Jack consoled her. "They interview people every
day...or often, anyway. You can understand how they wouldn't want a bunch
of ugly bastards roaming around that nice resort of theirs. It would, you
know, spoil the decorum. You look very beautiful in the nude and you
shouldn't be ashamed of it."
"You don't look bad yourself," Jill smiled. "I didn't know your dick
was that large!" She covered her mouth with her hand and leaned forward
and giggled as she said it.
"You've got quite a large endowment yourself," Jack smiled at Jill. "I
never realized, with that vest and blouse and bra and all you wear."
"You don't they're too large, do you?" Jill asked, a note of concern in
her voice.
"No, no!" Jack said. "Breasts can be too big, in my opinion, but yours
aren't. They're just right for accommodating a dick like mine between
them."
"Jack," Jill confided. "I don't know if I can eat. That probing
interview got me all wound up."
"Me too," Jack replied. "I'm hot, to say the least. Where did you make
reservations?"
"At the Beachcomber," Jill said. "It's right up the street."
"Mine are at the Everest," Jack said.
"Are you really as, uh, full as that girl said you were?" Jill asked
Jack.
"I haven't come in a month," Jack said.
"A month!" Jill exclaimed. "I guess that would make your balls
pretty swollen."
"Let's see what kind of a room you've got at the Beachcomber," Jack
suggested, to delighted agreement from Jill.
"I promised not to come," Jack said, taking Jill's soapy hand from his
dick as they stood naked in the steaming shower. "Any more of that and
I'll break my pledge."
"You really like Diane, don't you?" Jill asked. They stood face to
face, their bodies wet but only their private parts lathered with soap.
"Sure," Jack said. "But I like you too. A lot. And you and I are going
to have the time of our lives at that club. And that means no breaking
promises."
"She won't be able to tell," Jill said.
"Yes she will," Jack said. "Now turn around. It seems we're missing
a few areas in our washing here."
A little later Jack and Jill sat on the suite's king size bed, dry but
still naked. The toweling off they had given each other had done little to
lower their boiling passions.
Jill put her hand to her pussy as she sat cross-legged before Jack,
his erect penis still looming pleasantly before her.
"Well, I can come, even if you can't," Jill said, and began rubbing
herself. "You'll just have to watch me, I guess."
"Oh, no you don't," Jack cried, and tumbled atop Jill. He grabbed a
nearby pair of her discarded nylons.
"What are you doing?" Jill asked. Jack had clamped her wrists
together and was binding them with the nylons.
"You're going to stay tied up all night long, young lady, to make sure
you behave," Jack said.
"No! Jack! I don't want to!" Jill cried, but fought back with only half
her strength. Jack tied her wrists securely to the bars that made up the
bed's headboard, then planted his ass on her tummy and thrust his dick
between her breasts. He squeezed Jill's breasts together and began
threading his penis back and forth between them. Jill, her pussy still
aflame with desire, stopped kicking her legs and gazed down at the
delectable dick just inches from her mouth. A bead of saliva formed on
her lower lip and she licked it away with her tongue. Jack gave several
more thrusts and then, just stopping in time, fell on his back beside her.
"Go to sleep now," Jack said. He slid a hand underneath the small of
Jill's back and let his fingers glide down between her legs to tease her
clitoris. Jill turned her head toward Jack and their lips meshed. She
bucked her hips once or twice as their kiss lasted, urging Jack's fingers to
explore her further, to no avail. Jack touched just the tips of his digits to
her, lightly and intermittently. His penis stood erect, pointing at the
ceiling, straining as if a vagina was planted on the ceiling above them.
Outside the sky grew dark and the lights of Waikiki winked on.
Jack and Jill had made the round of most of the guests the following
evening when Diane appeared and asked them to pick their punishments for
initiation to the club.
"You should pick each other's initiations...that would be most
romantic," Diane advised, handing the list of male rituals to Jill and
the female initiation sheet to Jack.
"I want you to tease Jack but not let him come...all night long, just
like it says here," Jill said ruefully.
"Well, in that case you can give Jill an introductory whipping," Jack
said, finding that item on the list.
"Oh, you!" Jill cried. "My daddy never even spanked me!"
"Sounds like we should make up some lost time then," Jack smiled.
30
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