A New Waitress in Town

Introduction:
THE NEW WAITRESS
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. Every thing worked out except the job. In Boston there was 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 adams apple and my voice. Although mine doesn’t stand out that much, any adams 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, 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. “Your 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 buy taking each other to a shattering climax with out 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 til 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 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, your 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 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 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 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.”

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