Homeless - Cover

Homeless

by TheMoose63

Copyright© 2006 by TheMoose63

Erotica Sex Story: Three rich kids, a house to themselves and looking for some pussy. Enter a homeless woman and what can happen? How will the boys treat her? Can the woman save her dignity? Warning this has a solid ending!

Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa   Teenagers   Consensual   Orgy   Oral Sex   .

There were always the three of us, Billy Wagner, Terry Goodman and myself Robert (Rob) Cook all of us life long friends. We were the Three Amigos, The Three Musketeers maybe even the Three Horsemen of the Apocalypse (naw, there were four of them), anyway we were all 17, seniors in high school and right now very much on the look out for some pussy. We lived in the very upscale gated community of Metropolis just north of San Diego and our families all had money, real money if you know what I mean. Terry's folks had left on a two week vacation and his house was now our very own playpen. We knew we had a place to screw any conquests we could find and there was always plenty of booze available for our own entertainment or to hopefully ply any nubile young thing right out of her panties. The only real problem was that we were now into our third night of trying to find available girls but there didn't seem to be anyone interested in partying with us, none, nada! It was Saturday afternoon and we were sitting around Terry's house, drinking his dads' beer and trying to come up with a good game plan, any plan for Christ sakes.

"Fuck it," Terry said, "Let's take the car and go see what we can find."

"Alright," I replied. "Where are we going that we haven't already been?"

"I'm thinking that we go over to Oceanside, there gotta be some girls over there, Christ with all the Marines around there's gotta be some strange pussy looking for a couple of nice guys — nice rich guys!"

With three aye votes we all piled into Terry's black Mercedes convertible and started our 30 minute cross county trip to the beautiful city of Oceanside. We parked the car down by the pier and walked up and down the beach looking for any girl that seemed available but there weren't any female candidates we liked so we piled back into the car and a drove around town, still we had no luck. We had spent almost two hours in Oceanside with not so much as a nibble so we had decided to head back home and drink to our failure. That was the plan until Terry turned up Hill Street to head back to the freeway. We had stopped for the light on Mission when I saw the homeless woman standing on the corner holding her sign that read, 'Homeless — Will Work For Food. Please Help' and that gave me an idea. She looked to be around thirty but in her filthy clothes and with a dirty face who could really tell. She had on some really old clothes and she definitely needed a bath but she wasn't ugly or anything. She had bleached blonde hair with her much darker brown roots showing through about an inch and as I starred at her she gave me a really big smile. The light changed and Terry's foot touched the gas and the car jerked. "Hang on guys," I called as I reached into my wallet and took out a $10 dollar bill and handed it to her. "Here you go lady."

She took the bill and tucked it inside her shirt and most probably inside her bra. "Thank you sir and May God bless you."

"What the fuck did you do that for?" Terry asked starring at me incredulously.

"Well I was thinking..."

"That's always been a big problem for you Rob." Billy chimed in.

"Fuck you. Look did you guys see her sign? It said she would work for food and I was thinking..."

"We don't need any God damn work done." Terry said interrupted my train of thought.

"I know, I know. Look, how much money do you guys have with you?"

Billy pulled out his wallet and counted, "$85 bucks." Terry reached into his pocket and pulled out his money clip, "Here, you count it Rob." I counted $225 dollars and I knew that I had just a little over a hundred on me.

"Alright we have over $400 dollars between us so why not make the lady an offer, say $350 to screw all of us."

"For Christ's sakes Rob she's a dirty old fucking homeless bitch and I'm not sticking my dick into some trash eating bitch." Terry said.

"Me either." Billy mimicked.

"Alright, fine but let's think about this. So far we haven't found any girls willing to party with us and we have a house all to ourselves, we also have all the booze we need but once again what we don't have is any pussy! Hey, we've been looking for three days now and - nothing. I say we offer the lady the $350 and if she accepts we take her home, clean her up and fuck her, now what in the hell is wrong with that?"

Terry turned in his seat and looked at me. "I don't know Rob, I'm not sure my folks would want me to bring a homeless woman in their house, you know with all their stuff and everything."

"Of course they wouldn't. You think she's going to rob us? Hell we'll be with her the whole time, she can't do anything while were watching her and besides they'll never know anyway, Christ Terry who's going to tell them? Come on turn the car around and let's go back. If you're too chicken shit to ask her I will." Terry turned the car around and when we got back to the intersection he pulled into a gas station and parked. I hopped out and walked across the street to where the woman was standing, her back to me. "Excuse me lady." She turned and starred at me, kind of all scared and hesitant like maybe I was going to beat her up or something then her eyes sparkled with the recognition that I was the guy who had just given her the $10 dollar bill.

She backed away from me a bit. "What... what do you want kid?"

"Well I was looking at your sign, you know food for work and I... actually my friends and I, have a proposition for you."

"Uh huh, what kind of a proposition is that? I don't do anything illegal."

"Look lady we live on the other side of the county in a real nice house and... well there isn't anybody home right now but there is plenty of food and booze and a nice hot shower and, well the three of us were thinking that maybe you might like to come over and party with us, what do you say?"

"Party? What kind of a party do you have in mind?"

"A $350 dollar party. $350 dollars and it's all yours if you come with us. Hell we'll even bring you back here if that's what you want."

"Three hundred fifty dollars?"

"That's right."

"So what do I gotta do for that kind of money, kill someone?"

"Nope, nothing like that at all. Actually were looking for a little fun, you know, sex."

She starred at me for a long time and I was pretty sure she was going to tell me to go fuck myself but she didn't. "So you're going to give me $350 bucks to go to some fancy house, drink your booze and fuck the three of you, is that about it?"

"Yup, that's it."

She starred across the intersection at Terry and Billy sitting in the Benz, then turned back to me. "I want the money up front, before I get into the car."

"No problem lady. Say what's your name?"

"Tami. Tami Hoag."

"Alright Tami Hoag, my name is Rob and those two guys over there are Terry in the drivers seat and Billy sitting shotgun, now come on let's go." We walked back across the intersection and over to the Benz. I put my hands on the door next to Billy. "She wants the money up front, cough up guys." They all took out their money and I counted out the $350 and gave it to Tami who slipped it inside her bra. I opened the door and pulled the seat forward and Tami crawled into the back and I followed. Terry gunned the engine and we took off, headed back home for a party and a little pussy. As we drove along I looked at the homeless woman and indeed she looked to be in her early thirties. Her hair and face were a mess but she seemed fairly clean otherwise, at least for someone living on the street. She was tall and thin which showed off her large breasts. While we drove I saw Terry starring at Tami in the rear view mirror and Billy had turned sideways in his seat to look at her too. I put my hand on her knee and she jerked away but when she realized what she had done and she relaxed a bit and picked up my hand and set it back onto her leg. Feeling a little bolder now I reached over and slid my hand inside her blouse and cupped her breast. She didn't stop me but all I could feel was the wad of money inside her bra.

A half hour later we were almost to Metropolis and when Terry made the left turn and drove through the gates and up the hill and in to his driveway I was starting to get excited. We stopped and Tami whistled at the opulence of the two acre piece of property. Terry pushed the garage door opener and then eased the car into the third space of the five car garage and then he closed the door. We all got out of the car and Terry keyed the code into the alarm system and when it shut down the four of us walked into the house. Billy immediately went to the fridge and grabbed a beer.

"I'm getting a beer, anyone else want one?"

"Yea, grab me one," I yelled then I turned to Tami and asked if she wanted a one too. She nodded her head so I yelled back at Billy, "Grab a bottle for Tami too."

Terry was really nervous about the whole thing and you could see him twitching as he watched Tami look around the house at all the expensive furniture and decorations. "Grab me one too Billy." Terry yelled then he put his arm around my shoulder and leaned down and whispered, "This was your bright idea Rob so you get her skinny ass upstairs and into the shower before I fucking puke looking at her."

"Hey no problem bro, be nice." I turned to Tami and took her by the hand. "Come with me Tami, we'll go upstairs and get cleaned up."

"OK, actually it's going to be really nice to have a long hot shower... say do you think there might be some old clothes lying around somewhere that I could have, I'm pretty much out of anything serviceable." She took my hand and smiled as we walked up the staircase each of us sipping our beer.

"Sure, I'll ask Terry if maybe his mom has something you could have, you're both look to be about the same size." We walked into the master bedroom and Tami was stunned by the sheer size of the room, the huge dressers, the California King bed in the center of the room and especially the his and her walk-in closets. She walked all around the room touching and feeling almost everything then she walked into the bathroom.

Looking around the huge tiled room she said. "My God this place is a palace!" When I walked in Tami was standing in the middle of the bathroom looking inside the shower stall, an 8' by 8' square, stand alone, glass enclosed shower stall with sixteen separate shower heads.

"So I guess you like it?" I asked.

"God yes I can't wait to get cleaned up, Christ it's been... weeks since I've had a hot shower."

Tami wasn't the least bit shy about disrobing in front of me and maybe that's because of her life on the streets. She unbuttoned her dirty and worn blouse and tossed it onto the floor. She looked over at me and smiled then looked down at what had to have been a white bra at some point in time but was now nothing but a faded yellow and grimy piece of torn cloth with only one functional shoulder strap. She reached behind her and unsnapped the bra and took it off and held it until she could take something out of the cups then she tossed it on top of the blouse. She was holding her money in one hand and a small folding knife in the other. When she saw me looking at the knife she smiled.

"You don't have to worry Rob; it's for protection - on the streets. It can get nasty out there — for a woman."

I nodded my understanding. Tami bent over and shucked off her shoes and then pulled off her filthy jeans. She wasn't wearing any panties. Her body was a lot better looking than I had originally thought; her breasts looked to be about the size of grapefruits and were real white with dark red areolas and finger tipped sized nipples, surprisingly her breasts didn't have much sag to them. Her pubic hair was the same brown color as the roots on her head. I noticed that her pubic hair was pretty long and in need of a trimming. She had long legs and a heart shaped butt and I thought that she must have been really pretty at one time. She walked over to the shower and opened the door and stepped inside. I saw that Terry and Billy had joined us, standing in the doorway watching her as she undressed.

"God the bitch doesn't look half bad without those rags." Terry quipped.

"Look Terry why don't you try and treat Tami like a woman and not like just another piece of your furniture and you need to don't call her names either, Christ Terry she's a person just like us only less fortunate. Try and have some manners would you! Oh, and could you see if your mom has some old clothes she wouldn't mind donating, something that just might make Tami feel a little better."

As I as berated him I noticed for the first time that he had brought a bottle of vodka upstairs and was sharing it back and forth with Billy. "Alright I'll see what the fuck I can find, after all why shouldn't my family be the outfitter for the poor and downtrodden. What the hell size is she anyway?"

"Christ Terry how the hell should I know? Why not ask her, she's right there in front of you." Terry looked at Tami standing in the shower washing her breasts with a washcloth.

 
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