A New Crosdresser Waitress In Town

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 from a Boston
University, 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 would 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. Everything 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 adamsapple and
my voice. Although mine doesn’t stand out that much, any
adamsapples 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 when 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, seemed 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 viola, 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 letch. 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 a
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 letch.

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 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 cocksucker 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 passed 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 warm creamy 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
think 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 wild sex, and I would
often fuck her in all conceivable ways, lots of oral sex
too as she loved the way I used my tongue on her clit.
Sixty nine was a favorite for her and we usually ended
up a session by taking each other to a shattering climax
without mouths. I would bang 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 then, 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 pm 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 till later, no rush to get
home on Sunday,” he replied.
1. “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 seemed 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 at 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 several 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 boy’s 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
haucking back in his 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 talk 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 cloths, 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 makeup 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.”

Leave a Reply