Ms. High heels

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Amy was average height and had long straight blonde hair with blue eyes. Her bust was a triple D and a nice plump ass. She had average skin and always wore a medium amount of make up every day all day no matter what. Amy picked up the news paper to search for a job hoping to find something that would pay her rent. "To many hours. Not enough pay. Not qualified. BINGO!!!" She almost hollared. It was a diner looking for a waitress the pay wasn't impressive but with tips it could be perfect and the hours were manageable. Off to bed and first thing in the morning "I'll go check it out" she explained to herself with a long yawn. (The next morning) Amy awoke bright and early and started getting ready she gathered her clothes and slipped off her night gown. She grabbed her jeans and after adjusting her thong she slipped them on and buttoned them up. She turned looking at her Ass in the mirror making sure the jeans made it look just right then slipped on her undershirt then her button up shirt and started doing the buttons leaving 3 buttons at the top undone to compliment her breasts. Next it was off to the bathroom. She started brushing her hair to perfection. Next was her make up which took her a hour and a half to put on. She slipped into her heels and glanced at the time "shit I need to hurry" she told herself and ran out the house. She climbed into her roommates car and headed to the diner. The 30 minute drive to the diner wasn't bad but seemed to take forever as her stomach growled for breakfast. In no time she was pulling into the diner and headed to the front door. "Not to big not to small this seems like the perfect place" Amy said as she walked through the door. Amy walked up to the counter immediately and told the lady"I'm here for the job opening". "Right through that door" the lady explained. Amy smiled at the lady and walked to the door knocking on it. "Come in" a lady's voice said. Amy was shocked she was expecting a man to own the place. She took a deep breath then opened the door. "You must be here for the job I'm Stacey the owner of this diner. Please sit" the lady told Amy. "Yes ma'am" Amy politely replied as she sat down. "I won't waste either of our time with all the obvious questions. Most were explained in the add. I am however looking for hard workers and employees I can trust. This isn't a big business so trust is important to me. " Amy quickly replied " yes ma'am I'm honest hard working and will prove I'm trustworthy if you give me the job". Good you get one 10 minute break you get a sausage biscuits for breakfast for free when you arrive but eat it before the customers show up. Do you understand. " Stacey asked Amy. "Yes ma'am" Amy replied. "Good you will be waitressing tables 1-10 the tables are numbered so you'll do fine. If you accidentally waitress someone else's tables they get the tips not you so stick with your tables" Stacy explained. "Yes ma'am" Amy replied back. Stacy stood up"good you start now your shift is from 6am to 2pm then the afternoon waitresses will be arriving. Oh and table 10 in the back is reserved at all times for one customer named Mr. Jerry. If Mr. Jerry isn't here and someone else sits at his table you will kindly move them to another table.   You will be polite to Mr. Jerry and give him what he wants. I don't care if he asks for Cubans you will run to the store and get him a box of Cuban cigars I don't care if he wants you to belly dance you will give him what he wants. Understand. " Amy said" yes ma'am but why if I may ask" Stacey looked at Amy" because a year ago the kitchen caught fire and burnt half the diner down and I was going to have to close the place down and Mr. Jerry handed me a blank check when he found out and said there's no limit all I ask is that you rebuild this place so I don't have to find a new diner to eat at. In the 10 years I was open that was the only time I've heard him speak besides placing his order and he won't let me pay him back so it's the least I can do." Stacey opened the door still looking at Amy. Amy walked through the door looking back"I understand everything Ms. Stacey I won't let you down" Stacey pointed to a lady then closed the door. Amy walked up to the lady" I got the job and Ms. Stacey pointed to you. " "yea you won't talk to her let alone see her much anymore she stays in her office mostly. I'm Jessica the other waitress I waitress tables 11-20. That's Jammie she's the cook you won't talk much with her either. If you need anything ask me. There's no dress code so anything from modest to casual wear and while there is no dress code please nothing skanky. Any questions." Jessica held out a notebook. " not at the moment and I'll pretty much dress as I am today." Amy said as she took the note book. "Write your orders in there hang it in the kitchen window be sure to put the table number on it and I'll take care of the cash register until we decide your ready. Other than that that's it. Everything around here becomes a routine even the customers are the same every day with the occasional new person."  Amy said thank you as the first customers started walking in. Most of the morning went by smoothly even the lunch rush wasn't to bad. At 1:00pm a man walked in and sat at table 10. Amy rushed over" hi I'm Amy I'm your new waitress may I ask your name" the man looked up "I'll have a number 5." Amy asked again "may I ask your name sir" the man replied with "I'll have the number 5" Amy gave a weird look then walked to Jessica "whose that man at table 10 is that Mr. Jerry. " "yes and he wants a glass of water. He orders the same thing every day at the same time every day no exceptions." Jessica quickly replied. Amy placed his order and made his glass of water making sure it was full of ice. She walked back to the table and placed his drink on the table and asked"will the be anything else Mr. Jerry." "No ice" the man simply said. Amy was confused and just stood there. The man pushed the glass forward. Amy almost jumped at the glass of water realizing what he was talking about. She quickly grabbed the glass" my apologies Mr. Jerry" and with a quick turn she quickly walked back to the sink and emptied the glass out and refilled it with just water. "Table 10 order up" Amy was once again confused. She thought to herself wow that was fast there were atleast 5 orders in front of his. She shrugged it off and grabbed his plate headed back to his table. " here is your club sandwich and your water with no ice Mr. Jerry" she set the plate on the table in front of him and the glass of water to the side. "Will that be all Mr. Jerry." The man nodded then tapped the table three times with his finger. Amy smiled "enjoy your meal Mr. Jerry" Amy told the man as she walked away. Amy almost starred at the man waiting for him to get done with his meal. He ate slow and sipped his water occasionally. She noticed he was dirty. She paid especially close attention to his clothes which were not impressive a t-shirt a pair of old jeans and old boots considering he had checks with no limits. She struggled it off simply saying to herself maybe he is a drug lord or something I don't know. Suddenly she noticed he pushed his plate away signifying he was done with his meal. Amy rushed to his table ready to ask if he enjoyed his meal when suddenly she stepped wrong and what seemed like slow motion her ankle went side ways and she fell to the floor just as she reached his table. She just laid there a few seconds recovering from the pain and embarrassment when suddenly she felt a hand grab her arm. Amy looked up seeing Mr. Jerry standing there trying to help her up. Amy started to stand but was only focused on her arm. The man had a very firm grip on her making sure she was balanced until she was back on her feet. Amy's heart dropped as the man started brushing her clothes off once she was standing again. All she could think was the one person she was supposed to cater to was now brushing her clothes off like a child. The man was thorough even brushing off her chest and never once tried to look down her shirt. Once he was done he looked down at her heels and said "cute. Not practical for a waitress but cute." Amy blushed. "Follow me" Mr Jerry said and released her arm and started walking. Amy started following the man almost out of instinct. Mr. Jerry walk out of the door to a old rusted pick up truck. Amy was shocked she was expecting a nice car or even a jacked up truck from a man with a no limit check. Mr. Jerry looked at Amy then with a smile said "thank you for walking me to my truck Ms. high heels" then tucked some money in her front pocket. " that's for my meal the change is your tip. Enjoy the rest of your day. Your shift is about over" then the man got into his truck without another word. Amy walked back inside and pulled the money out of her pocket. She instantly ran back outside to catch the man before he left but it was to late he was gone. She walked back inside and found Jessica " Jessica Mr. Jerry made a mistake and gave me to much money" she explained. "Mr. Jerry doesn't make mistakes he is very precise I guess you could say. His meal costs 15 dollars even which I'll take and the rest is yours to keep." Said Jessica as she held out her hand. Amy handed her 15 dollars "but that means he gave me a hundred dollar tip" Amy looked at the clock and it was 2:00pm exactly. Time to go she thought to herself. She put her notebook in her back pocket and started to head to her car. On the way home she past a shoe store and pulled in. "Ms. High heels huh. Well if the man likes high heels the least I can do is get a new pair for him to see tomorrow considering he tipped me so well. " Amy said out loud to herself. 45 minutes later she walked out of the store carrying 4 bags. She struggled to get into her car with the 4 bags but after a few attempts managed to do so. "OMG I can't believe I just spent a hundred dollars on shoes. Oh well maybe if I'm extra nice to Mr. Jerry he will tip me again tomorrow."  Amy smiled and had enjoyed spending some money on herself but it was time to go home. She started her car and headed home again. As Amy walked through the door her roommate stood in front of her holding her hands out "can I have my heels back please" Amy slipped the heels off and handed them to the girl "I'm so sorry I had to use them for a job interview but I bought some of my own now" the roommate walked off rolling her eyes. Amy almost ran to her room in excitement and opened her closet and lined the shoes on the floor of the closet. She managed to get 6 brand new pairs of heels in one day. She sat on the floor for probably 15 minutes choosing wich pair she would wear tomorrow. "I'm definitely wearing these tomorrow" Amy said almost hollering in excitement. They were pink with a little jewel that dangled down by the buckle. "They will match my pink t-shirt I'm going to wear tomorrow." She plucked the shirt off the hanger and placed it on the dresser with a pair of jeans and the heels. The rest of the day was pretty normal. She washed her clothes, cleaned the dishes and picked up the house a little before changing into her night gown and heading to bed. The next morning came and Amy jumped out of bed excited she slipped her gown off slipped her shirt and pants on then headed to the bathroom to brush her hair and do her make up. She walked back into her room and grabbed her new heels slipping them on. A smile never left her face once the shoes were on. She headed to work eager and happy. As her shift progressed through the morning her mood mellowed out. At 1:00 pm Mr. Jerry walked in the door and Amy met him with a smile "right this way to your table Mr. Jerry." Amy walked him to his table and allowed him to sit down before saying "will you be having your usual Mr. Jerry." He nodded and she walked away as she wrote his order down and placed it in the kitchen window. She proceeded to get his cup of water and waited for his order. In a matter of minutes his order was ready as she expected. She grab his plate and his drink and walked back to his table and set his plate down in front of him and his drink to the side. "The number 5 and a glass of water no ice. " Amy twisted a little and rest one hand one the table and the other on her hip as she lifted her leg behind her "I hope you like my new heels as well Mr. Jerry. Will that be all" the man nodded then tapped the table 3 times with his finger and proceeded to eat his meal. Amy went back to waiting other tables making sure to watch Mr. Jerry. Once Mr. Jerry pushed his plate forward Amy rushed to his table "did you enjoy your meal Mr. Jerry. " He nodded then reached into his pocket and held some rolled up money out. Amy reached forward and grabbed the money but as she did the man turned her hand over. "Bitting your nails isn't very lady like" the man said right before letting go of the money. Amy quickly pushed her hands and the money in her pockets embarrassed. "Hmm it seems your wearing less make up as well" the man said as he stood up to leave. Amy walked with him to the front door "may I walk you to your truck Mr. Jerry. " Amy said in hopes things would turn around." "No thank you" the man told Amy before walking out the door. Amy's heart sunk deep into her chest. She was confused as to what she did wrong. Not to mention she didn't know why she wanted to cry right now. Amy looked at the time and noticed she was done with her shift and proceeded to walk out and drove off. Her mind was flooded with thoughts of what had happened at the dinner with Mr. Jerry. Only one thought stood out though, and while she was confused as to why it was important Amy turned the car around and pull into a parking lot the sign out front said beauty salon and make up. Amy rushed through the doors. A hour later Amy walked out with a new set of false pink nails and a bag of make up. Amy did as she usually did, she drove home put her make up in her room and started her daily chores, dishes cleaning up a little then off to bed. As Amy woke up the next morning there was no smile but instead a look of determination. She wore another pink shirt similar to yesterday's, a pair of jeans and the same heels as the day before. She rushed to the bathroom to brush her hair then put on her make up. She walked out of the bathroom and posed in the mirror she loved the way her make up looked now she went from wearing a medium amount of make up to wearing what's considered a lot of make up but she loved the look. She started smiling and headed off to work. The day seemed to drag by hours felt like days. She was only worried about 1:00 pm. At some point Amy stopped torturing herself and forgot about the time only paying attention to who walked in the door. "FINALLY" Amy almost cried out as Mr. Jerry walked through the door. The man waited at the door as Amy walked to him " welcome back Mr. Jerry. Your table is ready for you" Amy said as she held her hand out to point the way and follow him as he walked to his table and sat down. " your usual will be ready in a few minutes Mr. Jerry" said Amy as she walked away placing his order and getting his water. "Order up for table 10" someone yelled from the kitchen. She grabbed the plate and the drink and placed them as she normally did "will that be all Mr. Jerry." The man nodded and began to eat. Amy's heart dropped something was wrong she couldn't place it but she knew it was. "Did I do something wrong Mr. Jerry." The man shook his head no then tapped the table three times with his finger. Amy got excited suddenly " thank you Mr. Jerry please enjoy your meal sir" started cleaning not far from his table as she starred at him. As usual the man pushed his plate away and Amy headed towards him "did you enjoy your meal Mr. Jerry." The man nodded as he stood "follow" he said as he headed towards the door. Amy squealed in excitement and followed him to his truck. " I hope you like my new heels Mr. Jerry and my new nails" she said holding out her hand so he could view them. " I do. Your coming along nicely Amy. " the man said as he took her hand in his to view her nails. Amy let out a another squeal like a school girl. "Good night Amy" the man said as he started to get in his truck. Amy leaned in the window" may I do anything else for you Mr. Jerry" "not tonight Ms. high heels your doing very good" the man said as he handed her 15 dollars before starting his truck and heading off. Amy walk back in handing Jessica 30 dollars" I'm sorry I forgot to pay for Mr. Jerrys meal yesterday day" Amy headed home not stopping this time. She did her normal routine then she headed to bed. She layed awake thinking not able to sleep. She just realized Mr. Jerry had shaved. She rather enjoyed the freshly shaven man. Her mind started to wonder off. His sharp jaw line not to mention his muscles. He wasn't buff like a body builder but she easily saw his muscles through his t-shirt. And a man in jeans just did something to her. She was so happy when he said she was doing very good. She let a low moan as she orgasm not realizing she was softly rubbing her almost dripping wet pussy before falling asleep. Amy woke up the next morning and got dressed wearing a new pair of heels and did her make up like yesterday. She glimpsed at the clock. I've got twenty minutes I'll sit down and wait before I leave. She started remembering that afternoon and out of what seemed like pure reaction she shoved her hand down her pants and started rubbing her pussy through her panties. She felt amazing. Amy never really masterbated much but this felt right this felt amazing. She managed to rub herself to a orgasm before leaving for work. Amy pulled her hand out of her jeans and started her day as usual. The morning shift was almost unbearable, it seemed like it took days to pass by. Finally 1:00 pm came and she stood at the door and greeted Mr. Jerry and walked him to his table " if there's anything I can do for you Mr. Jerry please don't hesitate to ask. I'll be right back with your food. " Amy placed his order and made his drink. She brought him his plate setting it in front of him and his drink to the side. Amy stood there as he ate. She was silent waiting. Once Mr. Jerry slide his plate forward he tapped the table 3 times and Amy squealed like a school girl in excitement. Mr Jerry stood and walked to his truck as Amy followed him like a little puppy. Amy had not noticed her pussy started to get wet the moment he walked in the door. So much so she smelt herself but didn't realized it. Once they reached his truck Amy said" your meal is on me tonight Mr. Jerry. May I do something to please you sir" Amy waited with a big smile. "Come here" the man said. Amy walked up to him face to face still smiling. The man said good girl before grabbing her jeans and jerking them down in the parking lot. Amy blushed but was only happy she was able to do something for him tonight. His hand slide her panties over and felt her soaking wet pussy"have you been masterbating" he firmly said. Amy still smiling and said "yes sir once last night and once this morning sir." " good girls don't masterbate without permission" the man explained. Amy tried to speak but couldn't all she was focused on was his hand on her pussy. "M may I I um m m masterbate nnnnow sir" amy managed to force our. "No" the man said as he slipped a finger in her needy pussy. He slipped a finger deep inside her pussy and pulled it back out then pushed two fingers in as deep as he could. Her pussy eagerly excepted both fingers as Amy's eyes rolled back before she lost her balance from orgasming on his fingers. The man caught her in his arms " would you like to go shopping with me Amy" Mr. Jerry asked her as she regained her balance. " OMG yes please sir" Amy said. The man picked her up in his arms. Her jeans still around her ankles in the open parking lot. He set her in the seat of his truck. They proceeded to leave the parking lot and head to a mall. Amy sat there just now comprehending wat had happened in the parking lot. "I don't care what happened it felt so good. He makes me feel so good. I'll do anything he asks of me." She told herself. They arrived at the mall and proceeded to walk in. It was a mall she had never been to before and it seemed secluded as if hidden. " pick anything you want and it's yours Amy" the man said as they walked through the front door. Amy blushed " Mr Jerry sir will you help me decide what to buy" she said looking down at the floor. "Yes" the man said. 3 hours later they walked out of the store with probably atleast 30 bags. They placed the bags in the back of the truck. Mr. Jerry pulled on bag back out. "Come here" he said and Amy walked in front of him he grabbed her shirt pulling up and she raised her arms allowing him to take it off. Next he undone her bra and took it off. Amy stood there smiling the attention was bliss to her and he was so gentle with her. "Your heels take them off" he told her. She slipped the heels off. He unbuttoned her jeans and slid them off of her along with her panties and she stepped out of them. She stood there naked. He took her clothes and tossed them on the ground. He handed her the bag "dressed" he said and Amy did exactly that she pulled a strapless push up bra out of the bag. She didn't know why he got her this she had very nice breasts already but she put the bra on. She looked at the cleavage it gave her triple D breasts and she absolutely loved it.  It pushed them very high and almost looked as if her breasts would fall out of the bra any moment. She noticed her areoles were just barely covered by the bra. She pulled a skirt out of the bag and stepped into it and slide it up. She noticed first how tight the skirt was she could barely slip it over her plump ass. She then noticed the length of the skirt rested less than half an inch below her ass. She would have to be careful not to bend over at her hips. Next was the shirt. She pulled it out of the bag and proceeded to slip it on. It was a band aid type shirt. It wrapped around her breasts only. She adjusted the shirt  making sure to show the maximum amount of cleavage and the shirt rested maybe 3 inches below her bra. She then slipped her heels back on and looked back in the bag. Hmmm no panties she thought. She walked over to her pile of clothes bending at the hips to grab her panties. Suddenly she felt a very firm smack on her ass. "No panties" the man said. Amy's feeling almost got hurt but the sting on her ass headed straight for her pussy. It was instantly soaked. "Yes sir" Amy said before climbing in the truck. They started to drive off in the truck when Amy said " how may I repay you for all this wonderful stuff sir?" "It's a gift from me to you Amy you don't need to repay me" he replied. Amy then focused on her needy wet pussy. She shifted her legs slightly trying to find some relief but none was found. She tried to focus on how to repay him but her needy pussy kept interrupting her thoughts as she sat there when suddenly something caught her eyes. She didn't think she just reacted and leaned over unbuttoning the mans jeans and reached in pulling his semi hard cock out. Before he could say anything she wrapped her lips around the head and started sucking as she stroked his shaft waiting for him to get fully erect. The man pulled over and in no time he was rock hard. Amy's pussy got even wetter she was in blissful heaven as her mouth watered while she sucked his head. She proceed to push his cock in and out of her mouth only being able to take it about half way in. She felt each vein on his thick cock on her lips. She stopped only briefly to breath but never removed his cock from her mouth. The longer she sucked his thick cock the wetter she got. She felt his cock start to pulse and jerk in her mouth and she immediately pushed his cock to the back of her mouth suddenly feeling him cum she gulped and swallowed each load down just as fast as he could pump the next load in her mouth. Once he stopped cumming she licked his cock clean and look up smiling "it's the very least I can do for all your kindness sir."
           (To be continued)