Trailer Trash

I hope you enjoy this story.

Edited by DRGriffin

My situation with the Woolsey's changes

After the weekend, Jake was now in control. On Monday, I awoke with instructions texted from Jake already. Work out, big breakfast, play with myself for at least fifteen minutes but no orgasms, shower and dress in one of the slutty outfits. He also instructed me to send him a picture each time I changed clothes.

As I was running, I began to wonder what I was doing. I had to admit several things to myself: First, my life was more exciting than it had been before I made the deal with the Woolsey's. I had been bored but now my days were far more filled.

I found Jake exciting. I loved his cock. I constantly thought about him fucking me. I wanted him to be in command. I wanted him to kiss me and tell me he at least liked me but the strange thing was I liked that he was making me earn those things. He could fuck me anytime and anyway he wanted but I had to earn the kiss. Even without the deal with the Woolsey's I wanted Jake to own me. The few words Jake spoke were all important. It was like I wanted the challenge of finding out more about Jake.

I also had to admit I am an exhibitionist. I have to be forced but none the less I like it. I didn't choose to be running with tits flying and ass jiggling but I could feel the tingle between my legs. While Jake was parading me around shopping the day before I was in a constant state of arousal. He didn't make me do anything I didn't enjoy. Maybe I really am a trailer trash slut. Maybe this really is who I was all along. After all, I had always lived in a trailer park and isn't this what people thought of when they thought of trailer trash.

Finally, today is the first payment from the Woolsey's. Didn't I start this to help Cherry? And I am about to accomplish at least the first phase. I concluded that no matter what Mistress Sid or Mister Jake demand of me, I would make enough to secure Cherry's four-year degree.

When I got back from my run I had two texts. One from Jake telling me to use an anal plug when I masturbated. He finished like this.

Jake: 'I am going to take that trailer trash ass soon. You need to get serious about being prepared or it will hurt.'

Then I got this text.

Mistress Sid: 'Congratulations on your first month. Come for dinner tonight. I want to talk to you as a mother and pay you. It will only be us. Dress as you please. We are not playing tonight.'

I was taken aback by this invitation. What could Mistress Sid be up to? And does she mean to dress conservatively. She had cut up almost all my old clothing and the new stuff was certainly not demur.

Me: 'What time?'

Mistress Sid: 'Seven.'

So, I had breakfast and then masturbated with one of my new toys and the medium sized anal plug inserted. This one did hurt. I showered, put on one of the outfits Mistress Sid had cut up, a bra with the cup cut in half, a shirt with half the buttons cut off and a cut off skirt. I sent a picture to Jake.

Me: 'Here is the outfit I am wearing to Walmart. I am just running errands this afternoon.'

Jake: 'Your outfit is acceptable for Walmart.'

Me: 'Mistress Sid wants me to come to dinner and dress conservatively.'

Jake: 'Mistress Sid told me about the dinner invite. No need to send me a picture.'

Me: 'Do you know what she is doing?'

Jake: 'I do but you need to talk to her. You are on your own tonight. Good Luck.'

I so wanted to talk to Jake. I found myself most afraid that she wanted to pay me the one installment and call off the agreement. And it was not about the money. It was that I couldn't imagine not having Jake's attention. I wanted this to continue with Jake even though I knew it was going to get harder. After the experience with the medium sized plug, I couldn't imagine what taking Jake thick dick in my ass would feel like, other than painful.

I ran my errand in the slutty outfit. No doubt I flashed someone each time I bent over. Both upstairs and down. I was getting used to both the people who drooled over the risqué attire and those that treated me like a villain, mostly women.

At six I started to drive to Mistress Sid's house wearing the only outfit she had left untouched. It was a modest dress that covered from neck to the knee. I did wear a bra with the cup cut out. I was beginning to feel comfortable with these.

This time I parked in the driveway. I hadn't told Cherry I was coming over but this time it wouldn't have bothered me to run into her. I hadn't seen her in over two weeks and I was beginning to miss her even though we talked by phone most days.

Melville met me at the door. "Good to see you again Melville."

He said, "Yes Miss it has been a little while. Mistress Sid wanted me to tell you that tonight you aren't her slave, so treat her like anyone else."

I gave Melville a quizzical look wanting more but Melville simple lead me to the dining room and asked, "Would you like a cocktail? Mistress will be here in a few minutes."

The dining room was huge with a table that must sit over a dozen people. There were two places set at the end of the table. I said, "Just a glass of white wine will be fine."

Melville came back with a glass and left me.

Mistress Sid came in and I stood. She hugged me and said, "Thanks for coming. Let's dispense with this."

She handed me a check in the amount we had agreed to. I said as I gazed at the check, "Thank you Mistress Sid."

She said, "No need for the Mistress. Just call me Sid. Please have a seat."

We sat and I just couldn't stand it, "I don't understand what is going on here. Can you tell me?"

Sid smiled, "I know you are anxious but nothing bad is happening except I want to change the nature of our relationship but we are not backing out of our deal if that is what is worrying you. I want us first to get to know each other a little better."

She rang a bell and Melville came in. "Melville please bring out the first course."

Melville came back with a salad for each of us and poured Sid a glass of white wine.

I said, "You said we should get to know each other better first. But I think you know all about me."

"I do but you don't know me, do you?"

"No, I guess not."

Sid smiled as we began to eat. She said, "Well you know that Rod and I are spoiled rich kids, right?"

I was at a loss of how to answer this.

"Our father was very successful but also something of a deviant. Rod and I have also faced that we are also well outside the norm. Rod and I get our jollies from dominating people. We learned that from Dad. As such we could never maintain normal relationships. Hence, we have made a series of deals with people to help them by using them to feed our depravity. We learned this from Dad. I think you knew this?"

"Well, I'm not sure know is the right word but certainly guessed from what Mom has told me. What about your mother?"

Sid answered, "She looked away from everything Dad did including how he raised Rod and me. Our relationship with our mother was not the usual one. Dad controlled everything."

"I am so sorry."

Sid said, "Oh it seems bad but for us it didn't seem unusual at all. I know it seems that all of us, Dad, me and Rod, have taken advantage of people but, we always have tried to give our, ah, conquests a longer-term benefit like with you. We get the fun of our obsession and you get a better future for Cherry. Right?"

"I certainly agree that the deal you made with me is to my family's benefit. I must admit my big fear was that you would cancel the deal. I mean you have given me to Jake."

Sid said, "I am going to explain that. Let me do it in my own time."

I nodded and relaxed a little. She rang a bell, Melville came in and Sid instructed, "Bring us the main and pour us more wine." Melville brought is the main course and refilled our glasses.

I had one bite is a fish and said, "This is very good and the wine is excellent."

Sid said, "I am glad you like it." She paused for a minute and said, "Yes, we agree that our arrangement has been mutually beneficial. Now let me tell you something I don't think you knew about me. I have a son."

She paused and looked at me to respond. I was stunned and finally said, "Well my goodness. I didn't know you were married."

"I'm not and never have been. I was very young. A little younger than you when you had Cherry. It was an accident. Don't ask who the father was. No one will ever know except me."

I asked, "What is your son's name and where is he?"

"His name is Randy and he is in medical school. He is brilliant. Let me back track. Not many people know about Randy because to start Dad hired someone to take care of him. As I got older I wanted Randy back. It was obvious to me that Randy was exceptionally smart. So, we sent him to special schools. So, I have been a part time mother to Randy. On top of that I don't have many close friends or maybe none. Everything with Rod and I is transactional. We make money and dominate people. Which means we are never close to anyone."

"That sounds awful."

Sid said, "I know but no need to feel sorry for us. We have lived the life we want. But, I want Randy to have a normal life. So, I have kept him away from what Rod and I do for pleasure. Our Dad didn't do that and that is one of the reasons we are like, well, the way we are."

She stopped, rang the bell and had Melville clear the table. "Melville, we are going into the sitting room. Merilee, would you like some coffee or more alcohol?"

"I think I should switch to coffee. I have an hour drive back home."

Sid laughed and said, "Well, at least this time you will be fully clothed."

I laughed and nodded. We went to a small sitting room as Melville brought us coffee.

Sid started back, "Randy has been living here since this semester started. He is in his last year of medical school before his residency. And he is only twenty-one. He has lived a sheltered life. He has hardly dated up until now. For a while I thought he was gay. Which would be fine with me. You should know I don't judge people's sexual preference. After all, how could I?"

I nodded my understanding and I was beginning to guess where this was going.

She continued, "So he has been living here. He met Cherry the very first week she was here. He has been dating her or she has been dating him. Not sure the best description. But they have seen each other almost every day since they met. Randy has never reacted to anyone like he has to Cherry."

"What?" I exclaimed

Sid nodded understanding, "Yes, I know. Who could have guessed."

I then said angrily, "I can't believe she hasn't told me."

"Don't tell her I told you. Be patience with her. She is confused herself with this. In my defense, I have tried to get the two of you to talk. I know you and Cherry have a great relationship. In fact, I am a little envious of you and your daughter. I think it is just that you both are finding yourselves and neither of you are prepared to admit what is happening to you. But you will. However, I think our relationship has to change because of what Randy and Cherry are doing."

I said, "Are you trying to tell me they are in a sexual relationship?"

"Well, yes. And it happened quickly. Please know that Randy is not like Rod and me. He is almost exactly opposite of us. Which brings me to why you are here. You need any more coffee?"

"No, I'm fine." At this point, my mind was numbed. It was so strange to in one evening I go from her sex slave to potentially a future mother-in-law.

"So here we are. While I think, it would be fun to spend three months playing with you, I can't do anything that might hurt my son. He is a sweet innocent boy. Not because of anything I have done but because I mostly turned over the raising of Randy to others. I know he have fallen hard for Cherry. The last thing I want to have happen is for my obsession to hurt Randy. So, I want to offer you an out from our agreement in return for not making Cherry my enemy. So here is the deal, I will pay off as we agreed and you are free from us."

I thought, I can't believe this. I get enough money to help Cherry with school and I can quit this sex business. But then I thought about the weekend with Jake and how much I liked the attention I had received from him. As much as I hated myself for wanting to continue this, I really did want Jake for the next few months to be my tormentor.

Sid had been quiet while I thought and finally said, "Why are you thinking so hard about this? Do you want this to continue?" Sid gave me a sinister smile. I think she knew I did.

"Well, this doesn't seem fair to me. I think I understand now why you wanted me. I like being dominated. I, however, agree we can't get in the way of our children. You said that Jake was taking over as a gift to him. Why did you do that?"

Sid answered, "Jake's firm has done a good job for us and we know him very well. I wanted to do something special for him. I also thought the two of you would be good for each other. What are you thinking?"

"I would like to be Jake's as long as he would have me."

Sid smiled, "I assume you mean you want Jake to be your master for as long as he will do it. But you agree that you will never tell Cherry I had anything to do with your transformation."

"Yes, I hate to admit it but I want Jake to torment me like he did this weekend. I hate myself for wanting that but that is what I want."

Sid said, "It is time to accept who you are. Rod and I have. Cherry and Randy are figuring it out now. That is good with me. You are Jake's for as long as he wants you. I will agree to fund Cherry for her four-year degree no matter what Cherry and Randy do. You will agree that you won't turn Cherry against me. I will also agree to not do anything to pull Cherry and Randy into my lifestyle."

I stood and hugged Sid into me. She looked back at me, "Gosh, I would like to have one more night with you. I love those tits."

I couldn't believe I said, "Oh, maybe we can arrange that!"

I left Sid's house for the first time fully clothed and without having to put out.

Jake continues his domination of me

Tuesday and Wednesday, I continued the routine dictated by Jake. He made me diddle myself without an orgasm both days and by now I would do anything to get off. He continued to force me to wear slutty clothes everywhere. While I still didn't want to do this, I also found myself liking the attention I got from men and a few women. I couldn't go out without getting stares.

I was talking to Cherry almost every day on the phone. She still wasn't telling me about Randy but I knew it was coming. She had already begged off coming home the coming weekend but promised me that she would be home the following week. She said that mid-terms were coming up and she needed to study. But I guessed that it was more to do with Randy.

Wednesday morning, I got a text from Jake.

Jake: 'Tomorrow, you will watch porn with Mark and masturbate together.

Me: 'Can I have an orgasm?"

Jake: 'You can do anything but fuck. Enjoy.'

Me: 'Yes Sir.'

As strange as this is I started tingling with anticipation.

When Mark got home that afternoon I made the arrangements for our date. I told Mark that there was a movie I wanted to watch with him the following afternoon. He agreed to be home by two.

The following day, I began to worry about how I would spring on Mark that the movie I wanted to watch was one of my porn movies. But I decided that Mark was a guy and would like that. I realized that Jake wanted to humiliate me in front of my husband.

So, at one I started preparing for Mark. After showering and preening all the significant bits, I was faced with how much of a tart did I want to look like. I had to decide what does trailer trash like me wear to watch a porn flick with her husband she can't screw. Ultimately, I decided to wear a pair of thigh highs with a built in garter belt, a pair of stilettos and lots of makeup, dark red lipstick, thick red mascara, and lots of red accents for my cheeks. I also wore my slave collar, multiple gold chains that draped around my neck and wrapped around my belly. I also wore ankle bracelets. Jake had bought me the jewelry on our shopping trip.

I put out my toys on the coffee table and put the video I wanted to watch in the DVD player.

It was about thirty minutes before Mark said he would be home. I looked in the mirror and thought,

'If I don't look like a whore now I never will.'

Jake wanted me to text him a picture of what I was going to wear on my movie date with Mark.

It was almost instantaneous that I got a text back.

Jake: 'If I could get away this afternoon, I would be there. You look like a trailer trash ready to be fucked. Holy fuck, you are hot. Too bad it is only for your wimpy husband. Remember you are to save that pussy and ass for me this weekend. That's right you are mine starting Saturday at one.'

I was dripping wet and his response only made me more so.

Me: 'I am so excited. I wish you would come fuck me now. I feel like such a slut and it is making me unbelievably anxious. I am ready for you to take me any way you want.'

What was I thinking? I had just invited him to do whatever he wanted with me. There must be something wrong with me.

Jake: 'I will see you tonight.'

Me: 'Yes Sir.'

At the last minute, I decided to put on a tee shirt and only spring my slut-wear on Mark as we started the movie. Mark walked in almost exactly at two.

To my surprise Mark wasn't alone. There was a man with him. He was old and disheveled.

I jumped up and ran to the bedroom yelling, "Mark, I didn't know you were going to bring someone home."

I slammed the door as Mark said back, "This is Bruce, he needed some place to stay tonight."

I heard Bruce say, "Don't worry Mark, it looks like your wife had something else in mind."

Mark said, "Oh it will be okay."

I wined back, "This ruin all my plans."

I decided to text Jake.

Me: 'Mark brought someone home'

Jake: 'So'

Me: 'I can't watch a porno movie with someone I don't even know'

Jake: 'Why not?'

Me: 'I just can't'

Jake: 'You will unless Mark says no. Didn't you tell him what the movie was?'

Me: 'No'

Jake: 'If you don't I will punish you.'

Me: 'Yes, Sir.'

Jake: 'Use your medium anal plug. That ass needs to ready for the weekend.'

Me: 'Yes Sir.'

I went back into the living room where Mark and Bruce were drinking a coke.

I said, "Mark, I wanted us to watch an, ah, adult movie together and enjoy ourselves."

Mark said, "Oh good that sounds like fun doesn't it Bruce?"

Bruce said, "Fine with me but I think I need a shower first. Mind if I use your shower?"

Mark said, "No problem. No need for anything but your underwear. Melons doesn't mind."

I looked at Mark with daggers in my eyes. Mark showed Bruce to the shower.

When he came back he said, "Jake put me up to this. He told me to bring someone home to join us. Bruce knows that he can't fuck you and I won't allow him."

I was fuming mad, "What! You mean Jake told you to do this."

Mark smiled, "Yep. He said if you objected that I should tell you that you will enjoy it."

I sat fuming until I realized that Jake was setting me up for additional humiliation. I calmed down a little and decided I had no choice unless I was prepared to stop with Jake.

Bruce came back wearing a pair of Mark's boxers.

Mark said to me, "Are you ready to start the movie?"

I said disgustedly, "Sure, why not."

I kept my tee shirt on as Mark started the movie.

It was a spoof on a spy film with a lot of buxom, naked women along with large dick men. You know standard porn. The opening scene had the lead women, fake blonde with fake boobs and little acting skills being screwed by the lead male, fake blonde with pumped up muscles and a dick that looked a lot like Jake's.