Roomy Service
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Room Service free porn video
Room Service
By Sasha Jenkins
Jake Thomas was 40 years old when he was introduced to
crossdressing. He only stood 5'4", had long red hair that
he kept in a ponytail and only weighed 140 lbs. He kept a
great many secrets about what certain guest's tastes were
and he also kept a huge secret of his own. He was bi-
curious but never had the courage to see if he liked it. He
had drunkenly told only one person about it and she seemed
understanding about it. But he had a commanding presence
and a charismatic nature. He was the manger of the staff-
cleaning department at a major seaside hotel. He was
responsible for overseeing that the cleaning women were
dressed in their sailor uniforms, room service was on time
and the overall cleanliness of the hotel. He never realized
how hard he pushed his staff, but he was soon going to find
out.
The employee Christmas dinner and dance was drawing to a
close and Jake was overseeing the decorations on the tables
and around the ballroom when Nicole, his chief cleaner,
brought over a couple of mixed drinks and offered him one.
Jake drank the first one in one swallow and wondered how
much liquor was used to make it.
"Jake, if we get the decorations done in record time, could
we start celebrating a little early?" Nicole asked handing
him the other drink.
Jake drank the rest of the second and looked around and
shook his head. "If you all would stop farting around and
actually get to work, then yeah, you can."
Nicole shot him a look of venom. "Jake, an hour ago you
said that we were ahead of schedule."
"That was an hour ago and you still haven't gotten the food
or the drinks out yet." Jake had to shake his head because
the drinks were getting to him.
Nicole shook her head and looked around. "Boss, would you
care to make a wager?"
Jake looked at her and thought about it for a second.
"Sure, why not?"
"If we get everything else put out in 15 minutes, would you
be interested in finding out how hard you push us?"
Jake thought about it and smiled. "Sure. Are you gonna be
my boss for a night or something?"
Nicole smiled a little evil smile and said, "That's exactly
what I was thinking. The thing is though; you have to work
for me, just like I would you, with no bitching or
complaining. Also, you will have to wear what the cleaning
staff wears."
Being the betting type, Jake didn't even think twice.
"You're on. You all have it so easy anyway. All you do is
cleanup a room a little bit and move onto the next one."
Nicole smiled her evil smile again. "Got it easy huh?
There's more to it than that. But you'll find out soon
enough."
Snapping her fingers, Nicole didn't even look around as 20
people came out of nowhere and instantly had food and
drinks on the tables and were had the decorations finished.
Jake looked around open-mouthed. He was sure that there
were at least a couple of hours of work left and his staff
had finished it in less than 5 minutes.
"What? But how?" Jake could only stammer. At once, all the
women started clapping and cheering at how they had
partially beaten Mr. Jake Thomas. One even shouted out,
"Now he gets to find out how hard WE work around here."
Jake looked back at Nicole and said, "Well, a bet's a bet.
When do I get started, Boss?"
She grinned at him. "Now is a fine time to start."
She took him by the hand and led him towards the staff
changing rooms.
Nicole led Jake by the hand until they came to the doors
designating the men's and women's rooms. But he was
unprepared when Nicole shoved him through women's door.
"What are you doing? This is for women only. I can't get
dressed in here!" He shouted.
"Yes it is. This is where you are going to get dressed in
your uniform and your makeup done." Nicole was laughing
behind him. "Did you assume that you were going to be
dressed as a male? Are you also going to wimp out on our
bet?"
Jake was hard on his staff but he was also always honest
with them too. If word got out that he made a bet, lost and
didn't go through with it, he would lose the respect from
his workers. He finally quit struggling and was led in
front of the mirrors where the women put their makeup on.
Nicole sat him down in a chair and turned him around so
that he could see himself in the mirror. She pulled his
hair out of its ponytail and smiled. "In one hour, you
won't even recognize yourself." Jake could only gulp and
nod at Nicole as she turned him around and began her task.
After an hour, Nicole turned Jake around to face the mirror
again and he was astonished at the woman looking back at
him. Here was a woman looking at him that he would
definitely seek. Full, pouty red lips, long eyelashes and a
little blush on the cheeks gave Jake a very attractive
feminine face. Finished off with his hair in a loose
ponytail that would let the sailor cap sit on it without
messing it up.
"You're right, I don't recognize myself." Jake turned to
look at Nicole. "I'm beautiful."
Nicole grinned. "Yes you are. Over there you will find all
of your uniform and if you need help, I'm right here to
help you out."
Jake got up and made his way over to a counter with clothes
and some toiletries set on it. He picked up a razor and
some shave-gel instantly knew that he was supposed to shave
his legs. But, he was one of the few men in the world that
other than the hair on his head, he didn't have any other
hair anywhere on his body. So, he put the razor and gel
back down and surveyed the rest of the items. A short,
pleated navy blue skirt, a pair of L'Eggs white sheer
energy pantyhose, a white and navy blue striped short
sleeved shirt, a white satin bra, a pair of white socks and
a pair of dark colored Keds. There were also fake
fingernails and some red nail polish.
Jake stripped down to his briefs, sighed and sat down at
the chair in front of the counter. He applied the
fingernails the best he could. He took the polish bottle
and bent over to polish his toenails. While waiting for
them the dry, he applied polish to his fingernails. When he
was finished, he gently kicked his feet back and forth
while gently waving his fingers. After the polish dried, he
picked up the bra and tried to put it on. Nicole
immediately came over and showed him how to correctly put
it on. She took out a pair of breast forms from a drawer
and inserted them into the cups. Then she made him take off
his briefs and giggled when she saw how small his manhood
was.
"I think that you will be able to figure out the rest of
the uniform without my help. I'm gonna be outside. When
you're ready, come on out." She turned to walk away.
"Oh yeah, by the way. You're name is Jasmine. You have a
nametag already on the shirt."
Jake sighed and turned back to the rest of his task. He
turned around and snatched the pantyhose up. Very
carefully, he sat down and pulled the pantyhose on, careful
not tear and snag it. He remembered when he was little when
his mother would get upset if she put a run in her
stockings. He stood up, tucked his small dick between his
legs and pulled the pantyhose up to his waist and put the
socks on. He took the skirt and stepped into it and zipped
up the side and turned the zipper to the back. He looked
back down and noticed the skirt stopped at mid-thigh. He
pulled the shirt on and settled it over his breasts with
the nametag sticking prominently of his left breast. He sat
back down and put the Keds on and was glad that they were
padded. Last, he put the hat on his head and walked over to
a full-length mirror.
Jake was stunned at the sexy creature looking back at him.
He was a walking wet dream. He couldn't help but twirl in
his skirt and feel the way the air and the pleats of the
skirt played against his white pantyhosed legs. He walked
over to the dressing room door and walked out in the open.
Standing there in front of him were no less than 10 of his
female staff and they instantly broke into oohs and aahs.
Nicole walked over to him and whispered in his ear, "I know
that you can speak in a feminine voice. I overheard you a
week ago mimicking one of the guests."
Jake stood there for a moment and shyly said, "Hi everyone.
My name is Jasmine."
At once all of the women rushed over to him and started
hugging him and shaking his hand. Jake felt strangely
energized by this because he had never once received a hug
from any of his female staff.
Nicole interrupted. "Ladies, please. Jasmine has her first
room to clean upstairs and I need to show her how to get
started. Come on, Jasmine."
Nicole led Jasmine to the 2nd floor where all the cleaning
supplies were. She helped Jasmine load her cart and took
her to the first room.
"Before you go into a room, first knock on the door and say
loudly, 'Cleaning Staff'. Then you enter if you don't hear
anyone." Nicole demonstrated and after a few seconds opened
the door. Inside the room, Jasmine and Nicole saw that the
guests staying in it evidently didn't care that there were
clothes everywhere or that there was garbage all over the
floor.
Nicole looked at Jasmine and pointed. "First, get all of
the trash off the floor and then pick the clothes up, fold
them and set them somewhere out of the way. Then dust,
spray and wipe down all of the dressers, tables and
counters. Then, go to the bathroom and clean it up. I don't
think that you will have any problems there. After all that
is done, turn down the bed, put a chocolate on the pillows
and move on to the next room."
Jasmine looked back at Nicole and smiled. "Is that it? I
told you that you have it easy."
Nicole grinned her evil grin. "Oh? I tell you what, some
rooms that you come to will have guests in it but won't say
anything until you come in. Then you can pick up 'tips'.
But you have to REALLY work for those."
Jasmine blinked at Nicole, not understanding. Nicole smiled
and said, "How do you think that I can drive a Camaro on my
salary?"
It dawned on Jasmine what Nicole meant. "I won't have to do
anything if I don't have to, right?"
"No you don't have to, but you make more money that way and
now you now why we have so many businessmen come back to
the hotel. No business means I'm out of a job." Nicole
tossed a little cosmetic bag to Jasmine. "This is in case
you need to redo your makeup. Now get to work."
Jasmine cleaned up the room and moved onto another one.
Inside of it the occupants managed to keep it mostly clean
even though they didn't have to. That one was a cinch.
Jasmine moved through a couple of more rooms without
incident until she came to one of the rooms frequently
requested by a wealthy landowner. As she moved into the
room, she saw that there was a handsome white man in his
sixties sitting on the bed with a smile on his face.
"You don't have to clean the room. But if you want to make
a good tip, then come in and shut the door." He said
gently.
Jasmine shut the door curiosity getting the better of her.
The man patted next to him and indicated that Jasmine was
to sit next to him. She smoothed her skirt back and sat
down next to him, crossing her legs.
The man placed a hand on Jasmine's leg and slowly caressed
up and down her thigh. Jasmine started at his touch but
settled back down at the sensations that the man was
causing. She felt her little dick starting to swell
underneath the pantyhose.
The man slowly looked into her eyes and said, "A good tip
to you if you do something for me."
Jasmine looked back at him and in her best feminine voice,
shyly said, "What do you want me to do?"
The man slowly ran his hand down Jasmine's leg until he
stopped at top of her sock. "All I want is for you to give
me a foot job while you feel up and down your legs. Then I
want to cum in your mouth."
Jasmine thought it over for a second and thought that this
was her big chance to see if she was really bi-sexual. She
nodded her head back at the man and he scooted back onto
the pillows, taking his trousers off and revealing a very
thick dick. Jasmine stared at it for a second, then bent
over and removed her socks and shoes. She spun around on
the bed revealing her red toenails to the old man. As she
inched closer to his crotch, she was amazed that for an old
man, his dick was large, hard and throbbing. Cautiously,
she touched one foot to the old man's dick and watched it
jump. Carefully taking the huge dick in the arches of both
her feet, she gently started stroking the old man's dick.
She watched as he moaned and he watched as she caressed her
legs and stroked his cock with her red toenailed feet. The
old man started breathing faster and faster as he prepared
to cum. Jasmine's little dick was straining against the
pantyhose as she moaned, slowly caressing her legs.
Right when she thought that she was going to cum herself,
the man pulled Jasmine around pushed her head down on his
dick. She almost gagged when it struck the back of her
throat, but she instinctively backed off of it a little and
clamped her lips around the base. She ran her tongue up and
down the dick and was rewarded with her first taste of cum.
She swallowed as much as she could but a little escaped out
and trickled down the side of her chin. Lost in lust,
Jasmine cleaned the old man's dick with her mouth and
slowly pulled back from it and looked up at him.
He smiled back down at her and said, "I love a woman that
will clean up after herself. Just for that, the tip is
going to be bigger." He nimbly moved off of the bed and
grabbed his wallet. He handed a couple of bills to Jasmine
after she had put her socks and shoes back on. Jasmine
accepted the money as the man turned to walk out the room.
"That's the reason that I keep coming back to this fine
establishment. Great service." He made a gentlemanly bow to
her and walked out of the room. Jasmine looked down at the
bills and for a second, thought that they were two tens.
But unfolding them, she realized that he had left her with
two crisp one hundred-dollar bills. She gasped when she saw
them but recovered and moved over the mirror to readjust
her makeup.
After that, Jasmine moved through a couple of more empty
rooms, cleaning and rearranging things until she came to a
room that was anything except empty. Inside the room were
three twenty-something black men and they all had the look
of athletes about them. From the smell in the room, it
smelled like there had been some drinking going on. All
three were sitting around a table, playing cards when
Jasmine walked in. She turned back around to leave,
apologizing for walking in on them when one of them called
me over.
"You don't need to run, honey. Come on over a sit down and
take a break."
Shyly, she walked over the bed a sat down, placing her
hands in her lap and staring at her feet. One of them got
up from the table and sat down on the bed next to her. She
looked over at him and smiled. He placed a huge hand on her
thigh and slowly caressed it.
"We know something about you, Jasmine. Our friend Nicole
said that you were bi-curious and that we were to take good
care of you. We're all bisexual so don't worry about a
thing." He leaned over and kissed Jasmine lightly on the
lips. She knew that she was going to have to thank Nicole
for this and give her a raise.
Slowly, Jasmine inched her way back onto the bed as all
three men took their clothes off and made their way onto
the bed, kissing and caressing Jasmine all over her body.
One pulled her shirt off while another one pulled her shoes
and socks off and nibbled at her toes. The one kissed her
first tore a hole in her pantyhose and sank down to lick at
her ass. Jasmine pulled the other two to either side of
her. One placed his cock onto her lips, which she greedily
took in her mouth and pumped the other with her fist.
The one that was licking her asshole found a tube of KY
jelly and started lubing her with it. Carefully, he worked
in one finger then two. He pumped his fingers in out of her
until he thought that she was loose enough, then climbed to
his knees and carefully put his huge dick to the entrance
of her virgin ass. He pulled her legs up onto his shoulders
and in one thrust, buried is cock deep inside of her pussy.
Jasmine knew that the moment he plunged into her she knew
that no longer had an ass. It was a pussy for this big stud
to use as he wished. He pumped in and out of her like there
was no tomorrow. This wasn't love making, but pure lust
filled sex. Jasmine moaned and wailed while she sucked and
mouth fucked all three cocks. As she was being fucked
orally and anally, she could feel a deep pressure building
inside of her and she knew that she was about to cum.
Suddenly, all three studs erupted on her and in her. There
was cum flowing out of her pussy and mouth. There was cum
all over her breasts, hair and face. All four collapsed and
slowly caressed each other. Jasmine was in sexual bliss.
Never had she cum so hard in her life.
They all there a little while and finally the men got up
and put their clothes on. One looked at her and said, "Damn
girl, you were pretty damn good for a virgin. Here's our
numbers in case you ever want to hook up again."
They all smiled at her as they passed by the bed and one by
one, they each dropped a hundred- dollar bill. Jasmine laid
there in a daze for a while when Nicole opened the door and
sat down on the bed next to her. She looked at the money
and grinned at her
"I guess that there wasn't anything that you didn't want to
do. How much have you made in tips?"
Jasmine sat up weakly. "Five hundred."
Nicole gasped at her. "Five hundred? I only made three
hundred my first time. So, do you still think that we have
it made?"
Jasmine started getting her clothes back on and said as she
was tying her shoes, "Yes. By the way, I'm giving you a
raise before I quit."
Nicole was shocked. "Quit? Why are you quitting?"
"Because, now I realize who I am and what I was meant to
be. Plus, I just made more money in a few hours than I make
in a day. I could work as a cleaning woman and make
'tips'." Jasmine giggled the last bit out.
Nicole was silent for a moment when she spoke up. "You
wouldn't have to quit. Just talk to management about just
working as a female in staff cleaning. You know how
understanding they are about things.
Jasmine looked at Nicole and smiled. "We'll see."
One year later, Jake Thomas had legally had his name
changed to Jasmine Thomas and the hotel management had let
her stay on as chief cleaner and had promoted Nicole as
Manager of cleaning services. Jasmine had started taking
hormones and didn't need to wear breast forms anymore as
she had a great 36C cup. True enough, Jasmine made more
money since deciding to become the woman she was than she
had in the last five years working as a man. But more
importantly, she was happier as woman in the last year than
she had been as man in forty.
The End
If you liked this story, email me at
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Miracle
- 15.04.2020
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