A New Waitress
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The New Waitress free porn video
The new Waitress
By Mary-Margret
Moving to a new community is always difficult, especially
when you're alone, with no friends or relatives to turn to. The
advantage though is that you can be anyone you want.
My name is Robin and I recently graduated University from
Boston, where my family has lived since coming to the US from
Ireland. I was only two years old when we came here and have no
recollection of Ireland at all. I was very settled in Boston, a
good school, swimming competitively on the school team, an
excellent job as a waiter at an upscale restaurant, girls, you
name it. Things were about to change though, as I decided to do
post graduate work at a specialized tech collage in Kentucky. It
would be a two-year program, which would launch my career in
electronic design. I had not carefully considered the change in
atmosphere from the big city to a small hick town off the
interstate.
The school was stately and old with character. It had a
pool which I would make use of as I swim every day. Classes were
to begin in ten days and I had flown in to get an apartment, get
a few things, and find a job. I had sold my car in Boston so I
could buy one here. Every thing worked out except the job. In
Boston there were plenty of good jobs for students. Working as
a waiter in a five star restaurant paid for four years of my
schooling. But there were no such places here. There were only
a couple of fast food joints, a small cafe, and a drug store in
this town. Then I heard about the Fifth Wheel. It was a
roadhouse at the exit ramp off the expressway. It had a small
motel next door and was a haven for truckers passing through.
The clerk at student services said the waitresses there did very
well, but since they only hired women I was out of luck.
I decided to check the place out. Maybe they had work for
men as well? It was early and the place was empty, but what a
barn. It was huge. The kitchen was a giant BBQ, for steaks and
ribs, the only menu items. There was stage for bands and a big
dance floor. A couple of waitresses were getting ready for the
late shift, and I couldn't help but notice how beautiful they
were. They were all tall, leggy, with great bodies and long
gorgeous hair. The uniforms helped too. They wore black silk
western shirts like Johnny Cash, a black leather mini skirt,
black stockings, high-heeled boots and a western scarf, like
sexy outlaws. I bet they hauled in great tips.
One of the waitresses asked me if needed anything, so I
inquired about the job opening they advertised. She said there
were no openings in the kitchen, or for bus boys, but the boss
has been looking for a new girl to wait tables for a while. That
left me out. She said most girls were either intimidated about
their looks, didn't like the uniform, or were too squeamish of
the boss. She did mention that he was a pig and that any self-
respecting girl would never work for him. She got back to work
when he entered the room. He was about forty, tough looking,
with a couple of scars on his face, gray hair in a brush cut,
smoked a cigar, but wore an expensive looking suit without a
tie. I left feeling vanquished.
Back in Boston I gathered the last of my things. My family
was watching Mrs. Doubtfire on the television when it dawned on
me. I had done some acting in high school. I stood in front of
a mirror and did a quick assessment. I was very slim, one
hundred twenty-five pounds, from running and long distance
swimming, yet my legs looked strong. I have a fair complexion,
no hair on my chest, a small nose, but full lips, green eyes,
and my blond hair I keep short for swimming. I tried to imagine
myself as a woman. To think of it I was never the brutish
masculine type at all.
Later that night when everyone was asleep, I put on my
sisters dress, pantyhose and bra. I stuffed the bra, and donned
an old wig off my moms.
I applied makeup from sister's kit in the bathroom. Once
more I stood before the mirror and I liked what I saw. It needed
work but it could be done. The next morning I did some shopping
downtown in the gay district. I bought some special items like
panties which conceal the obvious, custom high heels, and a
magnificent redhead wig. The wig actually gets glued to the skin
to stay in place and look more realistic. I also picked out a
sexy dress for the interview. One stop at a lingerie store and
another at the drug store for makeup and I was set.
I needed an extra suitcase to fly back to Kentucky. The two
big problems I would face now were my Adam's apple and my voice.
Although mine doesn't stand out that much, any Adam's apples
show a little. Since the waitresses wore western scarves around
their necks, mine would be hidden, so I decided to where one for
the interview too. My voice is far from deep, but trying to
squeak up an octave all the time would be real tough. That's
were Mrs. Doubtfire reminded me about the accent. The accent
threw everyone. Since I was well practiced mocking my mother all
my life, I was able to do a pretty mean impression of an Irish
woman. I figured since my birth certificate states I was born in
Ireland that it would be believable. My name is gender neutral
so I wouldn't need to fake one. It seemed to be working out.
Once in Kentucky, I finished moving into my new apartment,
bought a car, and went to check the Fifth Wheel. The job was
still available and school was five days away. I immediately
practiced walking about the apartment in the high heels. They
were tough getting used to. I did my makeup several times for
practice. With false eyelashes, mascara, lipstick, the works, it
took over an hour to put on.
Finally the day of reckoning came. I was nervous but
remembered to be confident like my old drama teacher had taught.
I used to shave my body hair for swim meets so this was not new
to me. I clean shaved my armpits, legs, even my crotch, for full
effect. Then I carefully shaved my face very close taking my
sideburns away too. I covered myself with body lotion, powder,
and a hit of perfume. I applied my false fingernails, my wig and
did my makeup. I put on a black pushup bra over my foam tits
which I had placed silicon inserts in. They gave me a nice 36C
bust. I also wore a small corset, not that I needed to be
thinner but it gave my hips a feminine flair. The black panties
forced my dick up in the crotch so no bulges would show. I then
rolled on black, seamed stockings attaching them to my garters
on the corset. I picked out the black and white gingham two-
piece dress. I wore a white blouse under the tight waistcoat and
pulled up the skin tight, mid thigh skirt. I put my high heels
and a scarf on and voila, instant babe. I did look great, no
shit! My ass looked exceptionally round and squeezable with the
help of the corset and high heels.
My backdoor goes out to the parking lot, so I snuck out to
my car. At the Fifth Wheel I confidently strutted in, turning
lots of heads, hopefully for the right reasons. The waitress who
greeted me was the same one I spoke with the week before. She
showed no signs of recognizing me or of catching my act. When I
told her that I was here for the job she said she loved my
accent. She said the boss was going to like me but warned me
that he was a leech. She wished me good luck and went to set it
up with the boss. His office was on the second floor overlooking
the lounge. He opened the door and looked down at me. He stared
at me expressionless for a couple of minutes. I posed
femininely, crossing my legs giving him a good look at my long
legs. Finally, he waved me up, and I demurely went up to his
office.
His office was full of hunting trophies, and fish on the
walls and stunk of cigar smoke. He had me sit on a leather sofa.
I handed him my resume and references, which he perused. "What's
your name sweetheart?" he growled.
"It's Robin, sir", I gave back trying best to sound like my
mother.
"I'm Carl, not sir, and what are you? Irish?" he shot back.
"Yes, from Dublin originally, came to Boston for
university", I replied confidently.
"And you end up in this shit hole looking for a table job,
lot a good that school is. I never finished high school, and
look at me." His manners were deplorable. Satisfied with the
quick glance of my credentials he said, "All right, let's get a
look atcha", signaling with his finger to do a twirl. I felt
awkward but kept in mind what he was looking for. I did as he
asked.
"Nice, good body, great ass, and I love your red hair.
Don't got a redhead on staff," was his approval. "Bet the
customers go for that fancy accent of yours too", he continued.
Confidently I gave another voluntary turn but this time he
grabbed my ass on the way by. He chuckled and smiled. For a
split second I had to decide to react or not, it was momentary
shock. I just gave him a coy smile to keep him happy. He really
was a leech.
The real shock however came next. He had bought my act
completely, but said, "I like you Robin, a whole lot, so how bad
do you want this job?"
I wasn't sure what he asking and said, "I'm sorry, I don't
follow ya."
He continued, "I mean what are you willing to do to get the
job?"
I didn't like the sounds of that but was in too deep now.
"Anything, of course", I replied. With that he stepped closer to
the couch, still puffing on a cigar saying, "Good, let's see
what you can do with this", unzipping his fly and whipping out
his penis. I thought again about bailing, but I had gone too far
to back out and thought, "How bad can it be?" I've had blowjobs
from several girls and none of them seemed to mind. Besides,
it's not gay if I am a woman, which I was at the time. And that
big dick stared right at me with its one eye.
I mesmerized at it. It was about seven inches long, but
really fat, with angry looking veins bulging from its skin. A
drop of pre come glistened on the monstrous purple head. It was
already hard. I felt complimented by that and slowly leaned
forward to kiss my new friend. He sighed his pleasure as I ran
my tongue down the length of his shaft and kissed his bull size
balls. I took each one in my mouth and gave it a suck. I then
grasped the base of that shaft with my hand as I slowly licked
my way up to that head and licked away the fluid in the eye of
that mighty knob. Although the same length, it was easily twice
as thick as mine.
I put that thought away as right then I was a woman sucking
a man's cock. I opened wide and took it into my mouth until it
touched the back of my throat. I sucked hard on it and pumped
the base at the same time. "You're a great cock sucker Robin,
you must have been doin' this for a long time." Little did he
know that I was a rookie. With my spare hand I massaged his
balls and continued sucking him like that for ten minutes. I
looked up at him and saw him looking at me. I maintained eye
contact as I pushed the head of his cock past the back of my
throat until I had completely engulfed him. He moaned, closed
his eyes, held on to the back of my head and pumped a gusher of
jism down my throat. I nearly gagged, but he eased off enough to
let me swallow. He came for about a minute and I drank it all
down. For a moment I was proud of my accomplishments as a woman.
I licked Carl's shrinking dick clean, then he put it away.
He told me to pick out a uniform and that I should start the
next night at eight. He poured two shots of bourbon from his
private stock and handed me one, which I pounded back. He told
me that I would get a hundred dollar bonus for that and if I
came by his office the day before payday to repeat the
performance that I would see yet another hundred dollar bonus on
my check.
Neatly, I wiped my chin and got up to leave. I could feel
his gaze still burning into my ass. Just before stepping out, he
remarked, "That is one sweet ass! If your ever lookin' fer
someone to fuck it, or yer pussy, let me know."
What Gaul! I simply retorted playfully, "Sorry Carl, I'm
not that kind of girl." He was howling hysterically as I left.
I introduced myself confidently to the other waitresses,
being careful not to say too much, and picked out a tight
fitting uniform. The other women bought my act as well, not one
giving so much as an inquisitive look. My adrenaline was still
rushing when I arrived home as I snuck back in. When I was
finally safe and sound I took a deep breath and surmised. I
still could not believe that I just gave a man a blowjob. And
did he honestly thinks that I would back each week before payday
to do it again? Huh!
It was about that time when I realized how excited I was.
My dick was straining against the tight material of my panties.
I pulled up my skirt, dropped my underwear and my exposed member
sprang free. I rationalized that the thrill of not getting
caught turned me on and masturbated to a very quick orgasm. I
stared at myself in the mirror for an hour in disbelief that the
woman I stared at was me.
Working at the Fifth Wheel was all it was cracked up to be.
Everyone has a great time, the people are all real friendly, and
I made more in tips my first night than I made on my best night
at Chez Pierre. It was a major success. As a woman there are a
lot of differences on this job. I had no idea how much ass
grabbing, pinching, and propositioning there would be. On an
average night, about fifteen to twenty guys would ask me to have
sex or go out with them, all of whom I had no choice but to turn
down. I also felt a hand on my ass about every fifteen minutes
or so. I tried to handle it all gracefully as the other girls
did, with a smile and a hand smack, but never pissed the
customers off. If you wink at them after rejecting them they
keep coming back. The bouncer kept the serious drunks off of us.
One weird thing happened one night when I spied a heavenly
brunette at the bar trying to get picked up. She had a long
skirt on with a slit up to her hip and a low cut blouse. She was
definitely hot and I was unconsciously staring at her. Suddenly
she made eye contact and smiled. I had momentarily forgot that
I wasn't a man and quickly had to turn away. Later, when I was
clearing she came up to me and slipped me a note saying 'I want
to eat you! Call me, Amy' and her phone number. I really wish
that I could have taken her up on the offer but alas had to
forget about it.
I was all nervous that day before my first payday. I didn't
know why. After all, I had no intention of repeating the
blowjob. Since that interview though, it was all that I could
think of, every night, eventually masturbating myself to sleep.
Every day I saw Carl, smiling at me, relishing that moment.
"What a sick, ugly man he is", I thought to myself as I knocked
on his office door.
"Come on in darlin', I knew you'd be back", he giggled as
I shut the door behind me. Twenty minutes later, I was
swallowing Carl's salty load of cum for the second time. Again
he offered to fuck me and again I turned him down, as this scene
would become our weekly ritual. After each time I gave him head,
I went to the ladies room to freshen up, and my dick would be so
hard that I had to jerk it off to keep it from getting in the
way. I had to admit to myself that I really did enjoy doing it,
that it wasn't just for the money, which scared me.
Luckily, I finally met someone at school. I met Sandra at
the pool, while doing my morning workout. She was a regular
swimmer too. We got along great and started dating. We could
only go out in the afternoons because I worked five nights a
week. I told her that I did night deliveries for a large bakery
to throw her off. If I said I worked at a place she might be
inclined to come visit. Sandra was perfect though. She had blue
eyes, shoulder length blond hair, stood only five foot two and
had a killer hard swimmers body. She complimented me often on
how slim and smooth I appeared. Being a swimmer she knows that
the serious male swimmers shave off all their body hair.
After a few dates, we were having sex, and I would often
use Sandra to reassure my masculinity, fucking her with every
fiber of energy that I had. We would meet between classes, or
just after classes, have wild heart stopping sex than I would
have to go to work. We were in love and our relationship worked
for three months but the one problem she always had was the lack
of evenings and weekend time I had to spend time with her. It
was frustrating when she would want an evening out and I could
not do anything about it. I wasn't going to quit my rewarding
job. She got mad with me a few times on the subject and our
relationship began to show some strain.
Meanwhile, work was never better, the tips were rolling in,
and I had many admirers other than the boss. This one driver,
Roy, was a regular on Friday nights, was especially sweet on me,
asking me out every week. He was good looking as far as guys
went, in a Harrison Ford kind of way. But every week I continued
to reject him.
Then one Friday it happened, Sandra and I had a big fight
again because she wanted me to go with her and some friends to
a party. She was furious with me when I refused to call in sick
for the night at my 'bakery' job. After she stormed off, I got
ready for work as usual, donning my feminine persona for The
Fifth Wheel. At roughly 11:30 p.m. I noticed a group of college
kids come in for a few drinks, they were already pretty loaded.
Horror seized me when I discovered that one of them was my
Sandra, and that they were being sat in my section. My heart was
racing, and panic was setting in. I quickly grabbed one of the
other waitresses and asked to swap tables claiming one of the
boys had given me a rough time before and handed her $20.00. She
agreed thankfully for me.
As much as I tried to avoid them, I couldn't help but
notice one of the guys was all over Sandra. He was touching her,
put his arm around her, whispered in her ear. She was drunk and
giddy and pulled the guy, Steve, I think his name was, on to the
dance floor. They were like a train wreck from being so drunk.
When the band played a slow song she was hanging onto him
tightly, pressing her body against his. At one point he leaned
down to kiss her and she responded by giving him a long soul
kiss and greedily sucked on his tongue for all to see. I was
pissed, but could nothing about it, so I took it out on the
customers. I could blame it on PMS later. Finally Sandra, Steve
and their friends all left at 1:00 am and I cringed thinking
what they would do next. Roy was there that night and noticed my
dismay. He offered his help in any way and when I looked into
his deep blue eyes, I said,
"Will you still be in town tomorrow?"
"Ya, I usually don't head out til later, no rush to get
home on Sunday," he replied.
"Think you can take me out to dinner tomorrow, around
seven? Not here, out of town?" I asked batting my big eyelashes.
"Sure!" he stumbled in disbelief. I told the boss I was
feeling ill and might have the flue. They would not likely
expect me the next night.
I didn't hear from Sandra at all the next day. I followed
through with my date with Roy, enjoying dinner 15 miles away
from town. I had bought a new dress, a sexy blue number that
concealed the chest well, but was very leggy. I wore my black
seamed stockings, and 4" pumps to highlight my nice ass. I also
bought a 2" wide pearl choker to wear around my neck. I really
looked delicious and Roy told me every chance he had. We danced
for a while and he got a chance to let his hands feel up my rear
while I pressed my fake boobs against him. We kissed several
times, and I did become caught up in the moment, feeling like a
real woman. I to constantly fix my lipstick from all of the
making out we were doing.
Back at the motel, I had planned to just call it a night,
but I was as horny as he was and did not want to stop. While
making out in the car I could feel his hard on pressing on my
thigh through his pants. I would be too cruel to leave him like
that. As a guy I felt sorry for him, hell I felt sorry for
myself. My dick was cramped up inside my tight panties with no
room for movement. I stopped us for a minute and I told him that
I really wanted to have sex with him but was on my period. I
could see the disappointment in his eyes and decided to do what
only my boss knows about. I pulled out Roy's erection. It was
massive, maybe 10" long and thick. I gave it a few kisses and
long licks like an ice cream cone. Roy was in heaven; I could
tell he liked it so I gave him my best effort sucking his cock
better than I ever did Carl's. He was hard to deep throat but I
eventually got most of it down. I don't think he ever had head
like that and when he came I thought I would drown. I swallowed
desperately. His red-hot man sauce ran out the corners of my
mouth, down my chin and onto my dress. It was beautiful. I
cleaned him up with my mouth and wiped the remainder from my
face. He gave me a goodnight kiss on the forehead and I left him
and went home. I masturbated for two solid hours and came seven
times thinking about my evening.
For the next few days I was depressed. I figured that I
lost my girlfriend for good and that I was in falling in love
with a guy I could never be myself with. I was a mess. This
lasted a few weeks until in early January. The boss was giving
funny looks all day, not looking very pleased and it was getting
me worried. It was the day before payday and that meant the
usual blowjob in the office. I was scared when I went up to his
office.
He had some documents scattered on his desk that he was
leaning against. Usually we sat on his couch and I would lean
over and do him but something was different today. I just wanted
to get it over with and get out of there so I sank to my knees
on his hard wood floor and unzipped his pants and took out his
ugly cock. I went right to work. He seemed to take a while to
get hard this time. As I sucked him as best I could he
eventually got stiff and started fucking my face like he usually
did. This was a good sign. He soon popped his load, right on
queue right down into my stomach. As I was getting up, ready to
get out of there, he stopped me.
"Robin, that's a boys name right?" he asked.
"Girls or boys, I suppose," I nervously added.
"Ya, but you're a boy, right?" he pursued. "Or at least one
of them queeny fags, right?" I looked at the hunting trophies on
the wall and pictured my own head up there. I was silent and
shaking in fear.
He went on, "while doing the tax forms I noticed this thing
here, stating that your previous returns were filed as a male.
I thought it was a mistake so I called your last employer in
Boston to tell him. He assured me that you were very defiantly
a boy. So I thought about it for a while and needed to take
another look at you. I'll give you credit, you had me fooled. I
don't like being fooled. Who else knows about this?"
"No one! No one, just me I promise." I pleaded still using
my feminine voice. I was horrified that he would kill me or beat
the shit out of me at the very least.
"Stop, I ain't gonna hurt ya," He said. I was getting ready
to leave and asked,
"So I guess I'm fired then? I'll not say a word to anyone
on my way out and you'll never see me again, promise." A look of
disappointment came over his face.
"No, you're not fired! Hell you're the best waitress this
place ever had. Not to mention, you suck cock better than any
waitress I ever had. If you can keep up the act and keep your
mouth shut about this, you can keep working as long as you
want," he continued much to my relief. I was about to go and fix
myself up when Carl stopped me again. I was confused. My relief
was beginning to slip away.
"There is just one more thing," he said. "Now that you
don't have to hide what's under your skirt from me, I believe
it's time that I finally get to fuck that hot little ass." He
had his brawny hand on my arm and wheeled my around to his desk.
As I slammed into it Carl pushed me face down onto the desk. My
skirt was hiked up to my waist and I felt him pull my panties
down to my thighs. I thought about yelling for help but realized
that I preferred not to attract any attention. I heard him
hawking back in is throat before spitting a big gob of spit on
my ass. He probed with one of his meaty fingers at my anal
entrance finding the mark and working the saliva in. After a
minute of that he unzipped and pulled out his rejuvenated cock,
ready for action. He spit again into his palm and worked the
saliva over his angry member. Soon his familiar cock head was
pressing against my sphincter. It hurt like hell as he shoved it
in rather quickly. He didn't let up until I could feel his hairy
balls slapping against my sac. He grunted his approval of how
good and tight my ass felt around his dick.
Carl began pounding in and out of me while holding onto my
hips. I was in tears from the pain that he chose to ignore.
Slam! Slam! Slam! His cock was relentless in its anal assault.
It was quite rough and my own cock was free and rubbing against
the leather of my skirt, which was pinned against the top of the
boss's desk under both our weight. He had just had an orgasm
less than ten minutes before and at his age I knew that I was in
for the long haul. I was surprised to find that my dick was
equally as hard as the one plowing my bottom. It was about ten
minutes into the fucking that the pain I was feeling turned to
numbness. I started to enjoy the feeling of being filled. I
concentrated on trying to get Carl off as quick as possible. I
started fucking back. I met his thrusts with mine and worked my
ass in a circular motion. I found myself panting,
"Fuck me! That's it baby, fuck my sweet ass!" Carl loved
this and shifted into high gear, fucking me with everything he
had. I loved it too. Finally after almost twenty minutes of
drilling, my boss buried himself to the hilt and released his
blistering hot sperm into my rectum. We were both panting like
we just ran a marathon. He pulled out of my bum without
ceremony. I suddenly began to feel somewhat empty. Carl brought
his wet, flaccid unit around the desk to my face. I obediently
opened my mouth as he pushed it inside. I dutifully cleaned his
nasty cock up for him until it was spit shined. As he was fixing
himself up he said,
"Good piece of ass, I'm gonna love fucking that every week
before payday from now on. Don't worry you'll get the two
hundred I promised. Hurry up and clean up, I need you back to
work before the rush. Don't forget to clean my desk too." What
did he say? I soon realized what he was talking about. I had not
noticed that I had cum all over his desk and my skirt. I must
have been paying so much attention to his orgasm that I didn't
notice my own at the same time. Wow! Like a kitten I lapped up
my jism from his desk and swallowed it down. I used Carl's
private bathroom to tidy up my clothes, hair and makeup. My ass
was so sore, I didn't think I could finish working but somehow
I managed.
I was Carl's bitch from then on; fucking and sucking his
angry looking cock anytime he pleased. I did negotiate more free
time as compensation. The one thing lacking in my life called me
a couple weeks later. Sandra was very apologetic for being so
selfish to me. She admitted that she had sex with someone else
but regretted it. She said that she loved me and wanted me back
and said she would be more understanding from then on. I was
happy about that and told her that I would have more free time
for her as well. I couldn't wait to kiss and make up and told
her so. She told me to meet her at her place right away for make
up sex. But before I could hang up the phone to leave she said,
"Oh, one more thing, could you come dressed as the
waitress, I have always had this lesbian fantasy."
Lianne
- 08.08.2021
- 24
- 0
