Neighbors Helping Neighbors

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Lonely woman and lazy neighbor work things out together.
4.2k words
4.09
26.4k
4

Part 1 of the 2 part series

Updated 09/22/2022
Created 11/02/2012
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Sex is really one of those things that if you haven't had if for a while, you don't really think about not having it. My husband left me to live with our marriage counselor that we were seeing to try and patch up our marriage; little did I know that my husband and he were seeing each other well before our marriage was on the rocks. Now they got to see each other more often. I guess I can't complain too much, I got the house and the car and he got to spend his life with his new boyfriend. I'm not sure if that balances out the thirteen years of marriage but fuck it. He's happy and I'm over it. I just wish I had some cock on the regular.

I've been set up on dates by my friends and family but nothing pans out. It is usually some nerd that is an accountant or a lawyer, and they end up boring the hell out of me or trying to make me into a happy little homemaker. Fuck that. I make a great living and kick ass at what I do. It took me a long time to get to the assistant vice president position and I'm not going to give it up because some lame-o thinks I should be at home making dinner and popping out kids, save that crap for the good little Christian girls that are scared of their own shadow. If I had the time to go out, I would be drinking whiskey and going to the strip club every night, but since I decided to make it in this world the only time I get is the time I'm working.

Since I have such a busy schedule, my house is usually a pig sty, one day I was talking to the neighbors, and they mentioned that their son was a lazy slob that just sat around the house all day playing video games and smoking weed. They said they were going to throw him out if he didn't find a job, but it has been three months and he hasn't even started looking for anything. I listened to them put him down for a while and I knew they were waiting for me to offer to help them out and have him clean my place, but I really wasn't interested at all. I wanted someone that actually gave a damn about cleaning my house, not some bum whose parents wanted him to learn responsibility, but for some reason I told them I would give him a week before I went to an agency. The mom said "GREAT! I'll go introduce you." Then ran back into the house and fetched her son. Standing there with the dad he tried to start chatting me up but I was busy working from my phone to care, then the mom came back with this skinny, scruffy haired kid, who looked like shaggy from Scooby doo. He had on a tie died shirt, with sweat bottoms and flip flops, which would have been alright, except that it was the middle of November.

"This is Walter." said the neighbor lady.

"Hey." He replied with a half ass wave of his hand.

I looked him up and down and just shook my head, but what was I going to do. I already told them I would do it for a week but I made sure to put on my phone to call an agency tomorrow because I knew this wasn't going to work.

"Ok." I said. Be over at my place tomorrow at 7pm sharp. I'm not big on people that run late.

"Ok. 7pm." Walter said with a shrug. "Can I go back to my games now? Jeez!" Then Walter went back inside and up to his room.

His mom looked happy, I wished I shared her joy about the situation, and said, "Good. This is going to be good."

"Yeah, we'll see. Look I have to get up early tomorrow, so it was great talking to you but I have to go."

"Oh we understand," said the dad, "thanks for helping us out. It means a lot. If there is anything we can do for you, just ask"

"Sure. Have a nice night."

When I got to the house I put my stuff down and immediately called a cleaning service to set up an appointment for them to come out.

____________________________________________

When 7pm rolled around there was a knock on the door and I forgot that Walt was coming over. When I answered the door, there Walt stood wearing jeans, a t-shirt, wearing shoes this time, but looked like he hadn't shaved in a week.

"Here I am, 7pm sharp." Walt said with a bit of spirit that I didn't see yesterday.

"Look Walt, I know that I told your parents that I would give you a chance but I'm a very busy woman and wasting my time with someone like you is a bad investment. I'm sorry but I already called the cleaning service. They will be here tomorrow." I was getting ready to close the door when he put a hand was on the door keeping it open.

"Wait! Look I know that I didn't make the best impression on you the other day and I'm sorry, but I need some money. I'm tired of living with my parents and need to get out of my house. My parents try and make me out to be this piece of shit but I really have been looking for a job for the past three months, no matter what my parents might have told you. I just can't get one because they won't get me some new clothes and the one's I have I've out grown, so every time I go to an interview I look like crap. There has to be something that I can help with? Anything!! I just need some money for clothes and to get myself on my feet."

When I looked at him he had a pleading look in his eye and I could tell that he was telling me the truth. The problem was I really didn't want him cleaning my house, but then I had an idea.

"How old are you Walt?" I ask him

"19",he replies, "Why?"

"Come inside and let's talk."

I opened the door wider and he walked in with a little bit of a suspicious look on his face. He comes in and I tell him to sit on the couch, which he does.

"Do you like wine?" I ask

"Umm, sure. I guess."

I go to the kitchen and pull out two glasses from the cupboard, pour one of my favorite reds for him and myself then head back to the living room. I hand him the glass before joining him on the couch. I watch him take a sip and can tell that he has never had wine before by the quick cringe that his face makes.

"Look, I'm still going to have the cleaning company come tomorrow, just because I like to leave these things to the professionals. Nothing against you, I just feel like they should be the one to clean up my house."

"Ok, so what do you want from me?" His suspicion is beginning to grow and well as my excitement.

"Well, I'll tell you. I'm a very busy woman and don't really have the time to get out and meet many men. So this is where you come into play. You're going to be my sex toy. Whenever I want sex, you're going to stop whatever it is you're doing and come give it to me. Understand?"

The look on his face was priceless. He was in such shock that he almost dropped his glass of wine on the ground.

"So you're telling me that you're going to pay me to have sex with you? Isn't that what a whore does?"

"That's exactly what I'm telling you. You're going to be my little man whore. See, you're figuring it out already."

"How much does it pay?"

"Getting right to the point, ok, well that depends on you. How many women have you had sex with? How big is your cock? What are you willing to do sexually? All these things are going to be factors in how much money you make from me. The happier I am, the more you make. I think that's pretty simple."

There was a look on his face like he was pondering his situation a bit. The look of being scared was becoming less and less, I could see it in his eyes, and look of intrigue was taking over.

"I'm going to answer your questions first before I tell you what I'm looking for out of this deal. First, I've had sex with two women. Second, I haven't measured my cock but the two women that I have had sex with say that it is very satisfying. Finally, I'm very open minded sexually but anything out of the normal, like whips and chains or sex in public is going to cost you more whether you get off or not. Oh and don't think that I'm going to let you put something up my ass without getting paid a shitload of money for it. Understand?"

I could see the boy change right in front of my eyes. This wasn't someone that just played video games all day; this was a man that knew what he wanted. He was driven and it was turning me on something fierce. I couldn't help but smile when I responded.

"That sounds acceptable. I agree to pay you more for different sex act that are out of the normal."

"I want a flat weekly fee as well."

"What? I don't even know if you're a good lay or not, and you want me to just agree to paying a weekly fee? I'm not okay with that."

"Ok, well, how about this, you can pay me what you think I'm worth but after I learn some things and get better, then we can renegotiate the terms of our agreement. What is a reasonable amount of time before renegotiation can take place? One month, two months?"

I was beginning to like him the more he talked and was getting a good feeling about the whole situation.

"I think two months is very negotiable. That will give me enough time for you to learn anything you think you need to know and me enough time to evaluate your performances. Two months is perfect."

"Two months it is then. Now, I'm thinking forty per fuck."

"Twenty." I reply

"Thirty-five" he counters

I look at him with my eye cocked up, "twenty-five"

"Come on. You're making how much money a year? How about thirty?" He said with a stupid smile on his face.

I think for a minute then say, "Ok. Thirty it is."

We shake hands and I look him in the face and our eyes lock. He looks deep into my eyes, not scared anymore, but like someone that knows what they are doing, a professional, just like myself. We stay there looking at each other and I'm can't take my eyes away for fear of losing control of the situation.

"We need more wine, don't we?" He tells me in a low tone voice, not taking his eyes off mine. I finally break the trance to look at my glass and realize that it is empty. Without saying anything more he grabs my glass from my hand and heads to the kitchen. I'm hot and bothered for some reason and I feel a tingling inside of me that I haven't had since I was younger. Walt returns with the fresh glass of wine and hands me back mine, then sits down, except this time he is close enough to me that our knees are touching.

"So tell me what you like and are into, so that I know how to make my money." He says this with a devilish grin on his face as he takes a sip of wine.

"Well, since you brought it up, I love to have my pussy eaten, the longer the better. I love it when a man can use his tongue and not use any fingers to please me. A creative tongue goes a long way with me, so learn to love the pussy."

While I'm speaking, he sets his glass down on the coffee table then turns towards me. He grabs my glass and puts it with his on the table, then turns facing me again, this time his hand moves on my leg and touches my thigh. I can feel myself getting wetter and wetter but I try and hold it back, not wanting to lose control of the conversation.

"What else do you like?" He says to me while his hand moves up and down my thigh, getting closer and closer to my pussy. I feel my eye flutter with his touch, but try and push out and answer to his question. "Umm, I love sucking cock and getting fucked hard." Once the words leave my mouth he moves in and kisses me way too hard. He has his tongue down my throat and keeps pushing harder and harder on my face, all the while he is rubbing my pussy and I know he can feel how wet I am from the rubbing. I have to push him off of me a bit and once I do he instantly goes after my neck. Kissing and swirling around in different directions. It isn't too bad but the stubble on his face is starting to bother me.

"You need to stay shaven."

He lets out a little laugh then replies, "Okay. I can do that."

He moves down to my breast where he unbuttons my blouse and pulls it back behind me. While he is back there he fumbles around with my bra, it takes him a time or two but finally he gets it free and pulls it off my chest. He stands back and looks at my tits like they are the first pair he has ever seen before then he starts grabbing them and sucking them so hard and fast that it almost makes me upset. When he reaches my nipples and pinches them way to hard I have to say something.

"Woah, slow down there tiger. They are attached and that does hurt, so take it easy."

"Sorry." He says, dumbfounded.

I'm not sure this is going to work out as well as I thought, but then he tries again and this time he is soft and sensual. Licking my nipples with his tongue while massaging my tits with his hands, which happen to be larger than I thought.

"Mmmmm, that's better."

He stays on my tits for a while then moves down to my suit pants. Again, he fumbles around with the zipper and tries to yank them off, almost making me fall off the couch, but when he finally gets them down he realizes that I still have my shoes on and again looks dumbfounded.

Jeez, what did I agree to?

He grabs my shoes and tosses them over his shoulder and I almost gasp when they barely miss the television, not really because of the television but more because they are my brand new Louboutin's. This kid better learn how to do this better or I won't have anything nice left.

He looks up at me with a smile and I respond with a half ass grin. Just waiting on you buddy, I think to myself. He comes back up to my panties and pulls them down in one smooth motion. Well, at least he can't mess that up. He looks at my pussy and pushes his head down into my box. He starts licking and sucking at a pace that is almost irritating; not really concentrating on one area or trying to stay in one spot, he is just all over the place. I try and look past it and enjoy the attention, but it is difficult when there isn't much of an effort being made on his part to figure it all out. He started with so much potential and now this? I think I will have him get naked and hope that there is something under his pants that make this worth my time.

"Stop. Stand up and take off your clothes." I think he can hear the anger in my voice and is a little taken back by it.

"Umm, ok. Is there something wrong?"

"Yes, but we will talk about it after this is all over. Now stop talking and take off your clothes."

He stands up and nearly falls over the coffee table almost spilling the wine. He pushes the coffee table back in a bit of a fever, again almost spilling the wine glasses. While moving the coffee table he kicks his shoes off towards the door. They make a loud thump noise and leave a mark on my white door. He smiles but I don't. He sees me not smiling and pulls his shirt over his head. I look at his body and can hardly believe that anyone can be that skinny. He has some good height, taller than six foot I figure, but he couldn't weight more than one hundred and thirty pounds. I try and look impressed as he slowly undoes his buckle and pants, which instead of pulling down he just sort of wiggles his legs and lets them fall to the floor. I look at his fruit of the loom underwear and see a decent size bulge. This might work out, if this kid can get his shit straight. I watch him take a breath while he has his thumbs in his waistband and then he pulls down his tightie whites all the way down to his ankles. When he bends back up I look down at his cock and I looked like it could be something that is satisfying. It dangled down his thigh and looked like it was about six inches when it was semi hard, so I was guessing it was more like eight when it was at full attention. There was something that did make me a little gaggy. It didn't look like he trimmed his pubic hair ever. There was this huge bush of hair that was all over the base of his cock and some hairs that was even as long as his cock. I was totally turned off by it.

"So," He said looking at me with a stupid look on his face, "do you want to suck it?"

"Not really." I replied. "That jungle down there has to go. I'm not saying you have to shave if off, but you definitely need to give it a good trim. Get that cock hard and come fuck me before I lose interest and kick you the fuck out."

The look on his face was almost funny. "How should I get it hard if you're not going to suck it?"

"Same way all guys get their dicks hard when they don't have a woman, jerk that bad boy off. Don't worry; I'm going to play with my pussy, since you failed in that department too."

The look on a man's face when they find out that they are not the little Casanova's that they think they are is priceless. I almost thought a tear was forming in his eye. I'm not sure but if he doesn't get better, maybe paying the extra for his ass might be worth it, just to watch him cry.

I began to start playing with my pussy with my eyes closed; I don't think I could look at the hairy monster anymore. I began moaning as I touched my clit and rubbed my wet pussy. I began thinking of who I wanted in front of me, a tall hansom man that was clean shaven and could get hard on command. I began to start getting hot and worked up when I heard Walt say, "I'm hard. Can I fuck you now?" I broke from my trance and looked at his rock hard cock, it looked wonderful but I couldn't get over all the hair, so I told him "Sure. I guess."

When he got between my legs I felt his cock against the opening of my pussy and before I knew what was happening, he slammed his cock inside of me and started pumping as hard and as fast as he could. I wanted to push him off of me but suddenly I felt him tighten up and a few strong shots of cum entered my body.

"Did you really just cum inside of me? Oh my god! You better not have anything or I'm suing the shit out of you and your family. GOD!!! What a waste of my time. Get the fuck off of me and get the fuck out!"

I pushed him off of me, which wasn't that difficult because he weighed nothing and immediately went to the bathroom to get as much cum out of me as I could. When I came back he was on his knees gathering up his clothes from the ground.

When he looked up as saw me, he stopped collecting his clothes and said, "Could you please at least let me know where I could improve?"

"Where can I start? You don't know how to eat pussy, you cum too damn fast, you throw your shit around my house like a damn baboon and you are a skinny little fuck. Jesus Crist, eat a damn sandwich now and again."

When I looked at him again he really was crying. Shit! I walked up to him and told him to sit on the couch and we will go though it a bit before he leaves. He didn't look at me he just kept his head looking at the ground with tears running down his face.

"Look, don't think of tonight as the end of the world, think of it more as a starting point. Here I will make a list of things for you to improve on over the next two months, and if you're really dedicated about doing this then you should have no problem figuring these things out."

I went to the kitchen and grabbed one of my yellow notepads and began writing. When I was through writing there wasn't much room left on the single page of paper. I tore it out and handed it to him. He took it then said, "Wow, is there anything that you did like about tonight?"

"Yes, you started off well with the eye contact. I was so horny and wet before we even started that you probably could have made me cum just from touching me in the right way."

"That's it?" He said sounding a little disappointed. "What about my cock? Did you like it?"

"I did. Well, from the parts that weren't covered by all the pubic hair. It's a nice looking cock."

When I said this he started to cheer up a bit, then he looked down at the list of things again, but this time actually taking the time to read some of the comments.

There was a long pause but then he said, "Ok. I can make this work if you have faith in me. Will you still give me two months to correct me mistakes?"

"If you think that you have it inside of you to change, then yay, I'll give you two months."

He didn't say anything; he just continued to look at the paper. Then he spoke, "I know this is going to sound a bit wrong of me to ask, but is there any way that I could get the first three payments in advance?" He asked with a shrug in his shoulders and a stupid look on his face.

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