(G/M, MG, MM, con, rom, teen2)
This story might be fiction or might be true it is up to you as to what you think but it is for mature readers only. You can see a list of all my stories on the authors page under the author, Playtime69. Comments are appreciated at ShortStories@PlayTime69.e4ward.com.
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WARNING this story is a bit lacking in sex and has somewhat of a romantic but sad tone to it. If you want a story to "Get Off On" in a hurry skip this one but if you want something that will grab at your heart feel free to read on. Would love to hear your thoughts on this change to my regular story writing.
The Waitress
by: Playtime69
I have been a traveling businessman ever since my wife died from an unexpected complication to a basic surgery. I was deeply in love with her and when the doctor told me it was just a simple procedure I went to work not expecting there would be a problem. Then when I received a call saying there had been a complication and she had died on the operating table I simply fell apart. If it had not been for my boss I probably would not be here today. He worked with me giving me the time off I needed to keep it together. He then went beyond being nice and allowed me to be a traveling businessman. I sold my house and hit the road traveling to different areas never staying in any one place more than a week at a time but returning to each place every three to four months. Pretty much I could go and revisit areas I wanted to as often as I wanted so there were some I went to more than others.
I was in my early fifties when things got a little interesting. I had always looked much younger than my age as I worked out often at the hotel gyms and usually stayed at places with pools so I would get to do a lot of swimming. I had all my hair with its natural color and my cock was a nice 8" long that did not get used near enough. I typically would masturbate to some porn sites but on occasion I hooked up with different women I had got to know on my trips and from time to time I would find some new ones but they were always from people I had got to know. Guess what I am trying to say is I never went looking for hookers.
I had been in town a few days making some contacts and decided I would take an afternoon off and watch some porn so I made it back to my hotel room where I stripped down and got my lap top fired up. Surfing along I found two guys one being older and one being younger were doing some kissing. Usually I do not watch guys kissing so I was just about to move on when they broke the kiss and the older guy went down on the younger guy's uncut dick. This was more interesting so I continued to watch.
He sucked his cock for a few minutes then while still sucking he shoved a finger up the guy's butt hole finding his prostrate. He massaged his gland while pumping his cock in and out of his mouth. The young guy could feel his cum started to flow began to moan telling the older one he was about to blow. Timing it just right the old guy waited and when he knew the cum was about to fly pulled his lips from the cock but with his finger still up the guys ass he made the cum shoot. It shot alright as one stream went right in his mouth and the next four or five shots hit him in the face.
He pulled his finger from the young guys ass and raised up to where they were face to face. The young guy then kissed the older one again but quickly moved to licking his own cum while going back and forth to kissing him. I had been touching and playing with myself up until this point but when they started kissing again and then the fact the one was licking the cum off the other's face was too much for me to watch. Even though I was excited up until that point and was as hard as a rock I could not get that scene out of my head. I tried some other shows but it was no use. I was horny and my cock was as hard as a rock but because I had skipped lunch I decided to take a break and go out to eat.
I quickly got dressed and went to a national chain, bar and grill, that I had been to several times. I went in and found a waitress I knew and took my seat. I placed my order making small talk with the waitress I knew. While I ate I looked around watching others eat and work.
There was one waitress that caught my eye. She seemed to be in a hurry getting orders and taking the food to the tables. She did little smiling but when she did it was a very cute exciting smile. Her hair was medium length and medium brown. Her hair was in a pony tail off to the side of her head and had bangs across her forehead. There was just something about her that made me watch with close attention. I am not sure if it was her looks or her dedication to her job but no matter what it was caused me to watch her every move. She was short not even looking five feet tall and very thin. She probably did not even weigh 90 pounds with her clothes on but she looked healthy and as fast as she was moving and as hard as she was working I knew she was not sick.
I finally got the nerve and asked my waitress if the other waitress was married, divorced, or had a boyfriend. I asked some other questions and decided to make my move. I asked my waitress to ask her if she was interested in meeting me after she got off work. A few minutes later the waitress, I later came to know as Amy, looked over at me and gave me a big smile. My waitress told me she was interested and that she got off work at 11:00 and for me to come back. I finished eating and left thinking about how much fun the night was going to be.
Not knowing where we were going to end up I went back to my room and cleaned it up. I then took a shower and put on some nice clothes. I made sure I was back at 11:00 and waited outside. It was about 11:30 and still no Amy and was about to leave when I spotted her walking out the door. She looked around and when she spotted me she smiled and quickly walked up saying she was sorry but her boss made her work overtime. We talked a few minutes then I asked if she wanted to go back to her place or mine.
She paused then said, "Your place is fine."
I asked her if she wanted to ride with me but she wanted to drive her car. I walked her to her car and found it rather messy and full of different stuff. I did not comment and did not really think much about it. We went back to my hotel room where I let the office know about the additional car so they would not tow it then we went into my room. I asked her if she wanted a beer but said she was not 21 yet. I was surprised she admitted that as most would take the beer anyway.
I made a comment, "I thought you had to be 21 to serve alcohol."
She responded with a slight giggle, "No. You only have to be 18 to serve as long as there is someone 21 or older in charge." Then she asked, "Ummmmm, would you mind if I took a shower and get out of these clothes?"
I smiled and told her to make herself at home. She went to her car and in a few minutes she was back with a couple of bags. I figured they were full of her personal items and some clean clothes. She went into the bathroom and I heard the door lock. While she was in there I sat on the bed and drank a couple of beers. She had been in there quite some time and I was starting to get worried.
"Are you ok in there?" I called out.
"Yes, sorry. I will be out in a little bit." She answered.
I had a couple more beers and was really feeling good and horny thinking when she walked out she would be in some little sexy nightie and ready to fuck. Just like she said in a little bit she appeared but nothing like what I expected. She was not wearing any make-up and had on an oversized tee shirt that looked very worn. It was clean but looked old and well used. She put her bags on the floor by the wall and when she bent over I saw her panties. They too looked clean but very plain and very old and worn with some holes in them. All this really made me question who she was and why she really agreed to come to my room.
"Would you like to sit on the bed and watch TV?" I asked.
She smiled looking a little relived as she got into bed next to me. I put my arm around her as she snuggled up next to me. Without forcing myself on her I gently placed my other hand on her private area on top of her night shirt. She in turn put her hand on top of my privates that were covered by some sleeping shorts. I had already removed my shirt revealing my hairy chest. She placed her other hand on my chest and rubbed my hair. I leaned over and kissed her. She kissed me back being the first to open her mouth telling me to give her my tongue. I did so while I slipped my fingers inside her worn panties. She spread her legs inviting my fingers inside her pussy. I slipped a finger inside finding her hot and wet.
We continued to kiss while I finger fucked her tight slit. Her moans increased as I played and eventually I had her flat on her back. I straddled her small body as I pulled her panties off and threw them to the floor and pulled her shirt off her small body. I then pulled my shorts off revealing my super hard 8" cock. I could see fear in her face as my cock bounced up and down. We went back to kissing as I lowered myself and my cock found her small slit. I could tell this was going to be a tight fit because her pussy lips were closed tight. I was not sure if she was a virgin or just had not had sex in a while but either way I knew I had to go slow and be careful.
Slowly I lowered myself until my dick head was on the inside of her pussy lips then slowly very slowly I pushed until the head of my cock disappeared inside her twat. I could tell she was in pain but was not going to say anything. I was as careful as I could still going slowly I slid in and out of her hole until I could tell she was use to the feel of my oversized member. Finally, after almost an hour of work I was fucking the little girl. I had not been in a pussy hole that tight since I was a kid experimenting with the other children in the area. She eventually got use to me and was feeling the excitement of being fucked. My hands were all over her small but exciting breasts as my cock pistoned in and out of her cunt.
Without notice she screamed, "Yes! Yes!! Yes!!! Fuck my pussy. Fill me up with your cum! Make my cum coat your cock!"
I could do little more than grunt and moan as the effects of all the beer plus the work I was having to put out to fuck this hot chick was taking all my strength. I managed to ask if she wanted me to cum inside her or on her.
She grunted back, "It is safe. I am on the pill."
That was it. I could take no more and blew a load so big that it even amazed me. My entire body shook as my orgasm had taken over every muscle in my body. She too came and drenched my cock as it was still slowly sliding in and out of her pussy. Her tiny body convulsed as her orgasm trailed off. A couple minutes later we were back to holding each other but this time we were both naked not even trying to cover ourselves.
"Wow, that was great!" I commented.
She said nothing but held me tighter. I too gave her a tighter squeeze. While we rested I asked her if she wanted to spend the night or did she have to go home.
Amy being a little shy with her response finally said, "I...well...ummmm. You see I do not really have a home. I live in my car. So if I have to leave I have to find a safe place to park before I can go to sleep."
"I am so sorry. I did not know. Of course you can spend the night. And, it is not because you slept with me. You could have stayed the night even if we had not made love." I replied and in my mind we had really made love and not just had sex.
She again squeezed me tighter and I could feel wetness on my shoulder from where she began to cry. Without looking at her I simply asked if she wanted to talk about it. I knew from experience it helped sometimes when others knew about my problems even if they could not help.
She fought back the tears a bit and began to tell me her story. She told me when she was 16 years old her and her boyfriend got caught having sex. Her parents told her to leave the house and live with him if they were going to continue to do so. He was much older and lived on his own. Not long after she moved in with him she caught him fucking another girl and she left with not much more than the clothes she was wearing. She had grabbed some personal pictures and a few clothes but just what would fit in her car. She tried going home but her parents told her she was on her own and she was not wanted any longer. Without a place to live and with very little money she slept in her car. She ate when she could find something but it was not long before she had worn out her welcome with the few friends she had.
Luckily about that time she turned 17 and managed to get a job being a waitress by lying about how old she was. She had only worked there a few months when I met her so, yes, she was 17 when we fucked the first time but I really thought she was 18. It took all the money she could get to pay for gas for her car and for food so the only clothes she had was what she had when she moved out.
By the time she was finished with her story I was heartbroken. My eyes were watering and my nose was running. I not only felt bad for her and what she had been though but felt bad for having sex with her because I knew she only did it because she figured it was the only way I would let her sleep in my room. She had not slept in a bed in months and before I knew it she was asleep holding on to me like she would hold on to a teddy bear.
I laid awake for a while thinking. I knew I just had to help her just like I had helped others. The difference was I believed Amy's story. But then again, I had believed the other's stories too then had been proven wrong. I had given money to one girl that used the money for drugs and alcohol then another actually was buying condoms so her boyfriend could fuck her. There was something different about this girl and if she was lying she was doing a really good job of it.
The next morning when we woke up Amy told me thanks for everything and how she had not slept in a real bed in months and had not had a good shower in over a week but she knew it was over. She then started packing up her stuff. I told her I had to go make a few contacts but would be back and for her to stay. I gave her some money to go next door and eat then gave her a room key to get back into the room. Yes, I know. I was taking a chance. She could have stolen my lap top and all my stuff but it was a chance I was willing to take. I said nothing else but did kiss her good bye as I left.
I am sure she was a little confused being left along with all the stuff in the room but she got dressed and went to eat. When I got back I found not only was all my stuff still there but so was she and she was again asleep in the bed. I hated to wake her but had no choice.
"Amy." I called as I kissed her on the top of the head. When she woke up I said, "I am going to have to leave soon but I told the office I was going to pay for one more night and that you would be sleeping here. You can use the laundry facilities if you need to wash clothes just make sure you leave before 11:00 tomorrow morning."
I could see in her eyes many things. I could see appreciation for what I had done for her but I could also see confusion as to wondering why I had done so much for her. She grabbed and hugged me, telling me thanks, and that it really meant a lot to her to have someone to talk to. I told her I had one more surprise but told her she had to trust me. She said she did so I had her get in my car with me and we went to the department store down the road.
When we got there I told her I wanted her to pick out some new panties, bras, and basic clothes she really needed. I explained I did not have much money but wanted to help her out as best I could. This time she did not just tear up she started crying. I too had to fight back the tears as I wanted to do so much more for her but just could not. She did as I requested and quickly picked out a few things being very frugal with my money. I even had to make her buy a larger pack of panties so to make sure she would have enough. When we were back in the car I told her she needed to throw away her old stuff that was no good any longer which she agreed to do.
"We have one more stop to make." I said.
"Ok." She replied.
I pulled up to the local post office and took her inside. I got her a post office box and paid for the next year. I then bought her some stamps and envelopes. I told her I would write her to see how she was doing if she would write me back. I told her how she could get letters to me since I was all over and did not have a home either. She wrote down all the information before we walked out.
I took her back to the room packed my stuff and left. We both were in tears as I left her because I had been so nice to her and myself because I felt so bad for her. I could not get her out of my mind and that first night I sent her a letter telling her to stick with it and that things would get better. I told her all about my past wife and what I went through so I knew it was hard when you had no one. I told her I would never forget her and that I would be back as soon as I could.
It seemed like I made record time in getting back as it had only been two months. She knew I was coming from the letters I had sent her so it was not a surprise when I showed up to eat where she worked. She was still homeless and living in her car but she was happier and looked really good. It was funny that we never spoke about sex or even sleeping together. I had been treating her more like a daughter than a girlfriend and since I was more than twice her age I was not sure she even wanted me as anything other than a father figure. I will have to admit the sex we had that first night was some of the best sex I had ever had. Later, I found out it was the best she had ever had to that point too as her ex boyfriend's cock was only 4" long when he was hard.
I told her where I was staying and gave her a room key of her own. I told her I was going to be in town for a week but doing traveling outside of town so would be gone a lot. When she got off work she went straight to the hotel room and let herself inside. She kissed me then immediately took a shower getting dressed in a much nicer sleep set. She crawled into bed with me and kissed me hard telling me how much she missed me.
This time I let her make all the first moves because I wanted to know what she thought of our relationship. It was not long before I found out. She kissed me on the mouth then pulled the covers back moving down to my growing cock she pulled my shorts down revealing my grown manhood. In one quick move she slid the entire shaft into her mouth sucking as she pumped it in and out. Since the last time we were together I had not had sex with anyone other than my own hand so to have her lips locked around my member was shear heaven. She fucked my cock with her loving mouth and in a few short minutes I told her that if she did not stop I was going to explode. Hearing this she not only did not stop but she sped up sucking even harder. I erupted with what seemed like a gallon of cum which she eagerly drank down.
When she got me all cleaned up she told me she had not been with anyone else and dreamt about me every night. She also told me she figured I had not been having sex either and knew I would not last long so to make sure I would she gave me a blow job first thing. We both laughed about it because we knew it was all true. I waited only five or so minutes and I was back hard again. Finding out her favorite position was doggie style I helped her strip and had her get into position. I again took it real slow as I slid my long hard cock back into the best pussy I had ever had. I fucked her with all the strength I had my balls smacking at her pussy lips with each stroke into her cunt. Our moans of pleasure increased as we fucked until I exploded once again but this time inside her pussy. She not only had an orgasm she had multiple orgasms this time because she was much more relaxed.
I was working during the days and she worked until 11:00 or so each night. This did not leave us much time together but what time we did have was very precious to us both. We not only fucked each night but we got to know each other. The little things only couples would know. I took her shopping again and got her some more clothes but since she still lived in her car there was no since buying her much of anything else. I did buy her a teddy bear so she would have something to cuddle with when I was not around. She love that bear and took really good care of it.
I made sure to write and send her money as often as I could. She too wrote me often. I made special trips to see her whenever I was close enough and made sure I got back to the area every two to three months. We were as close as two people could get and in love more than most husband and wives were.
When she turned 18 I asked her if she trusted me. She said she did so I told her to tell her boss she had lied on the application but now she was 18. She did not want to do that because she knew he was going to fire her and she was really close to having enough money to get a room to live in. I knew the manager pretty good by then and had a good idea what would happen but also knew of my own plans. She did as I asked and sure enough she was fired but, he told her she had done such a good job that if she waited one month and reapplied he would hire her back and would even hire her back at a higher pay since she had experience. He even told her he would wait until season ended to fire her so he would not have to replace her when she was gone. When the time came and she was let go I had her ride with me. I took her everywhere I went and she stayed in my bed with me every night for one month we were the happiest people in the world. We got some funny looks from people because we looked like father daughter more than a boyfriend and girlfriend did.
When the month was up we both were sad because now we were back to being separated. The time we spent together just made us love each other even more. She went back to work. I went back on the road. And we both went back to writing each other more. Amy finally got a small room but when I would visit she would stay in the hotel room with me as she could not have male guests where she was.
The next year was hard on us both. With each visit it was harder for me to leave her not because I felt sorry for her any longer but because I loved her so much. She too felt more love than she did the first couple visits.
I could not stand it any longer and on her nineteenth birthday I asked her to marry me. Without a second thought she said, "Yes." Since I had no family, no home, and no relatives we decided to marry in her home town. It was not going to be complicated or big because she had no one either. She had not spoken to or had any knowledge of her parents since they told her she was not wanted any longer. She had very few friends so the guest list was very small.
Once we were married we found a house and bought it not even thinking about my job. When the honeymoon and my vacation was over which was taken up by moving and setting up the house I had to go back to work. Again I was gone three to four months at a time. We trusted each other and knew nothing was going to cause problems except we missed each other even more. I talked to my boss and he found me a position not far from where we bought the house. I would be home every weekend and some weeks I would be able to stay home all the time. This worked much better as now we were more of a family.
I talked Amy into getting her GED and then she started some college classes. I worked hard and was able to be home most of the time as I did some work from the computer from the house. Our love grew and grew as we grew into a perfect couple. Well almost perfect. My big fear had crept upon us and there was nothing we could do about it. In time I got old and retired but Amy was at the peak of her life. I knew I would someday get old and was afraid she would find someone else. Well only half came true. I did get old but she stayed with me. I do not know if it hurt more to have her with me of if she had left me. Every time I thought about it and looked into her eyes I could see the love she had for me but also the loneliness as I could not do things and be with her the way we were at the beginning.
I pushed her to get her college degree and from there she was able to get a very good well paying job. Now it was Amy that was off to work every day while I was at home. I missed her then as much as I am sure she missed me when I had to go off to work. I just know that if nothing else I had helped one person get though life in one piece. A person that was destine to fail without someone's help and love.
So if there is anyone out there that finds themselves in a situation to help someone think twice before you walk away without doing anything. If you are a person in need of help give it time and just maybe that one special person will come out of nowhere to save you from sure self destruction. I wish I could say it will happen but there are more people in need than there are people willing to help so just be patient cause someday just the right person might come along. I just wish I could help all the Amys of the world sex or no sex but I cannot see that going to happen.
The End