Trailer Trash Pt. 08

I looked at Josh and smiled, thinking how much he was like Jake, "Yes Sir. I must learn to be more confident in myself. Please punish me for my lack of confidence."

I draped myself over his lap. The skirt was so short it automatically showed my bare bottom.

Slap came the first hit on my right ass cheek. I said, "Thank you Sir, May I have another."

Slap. "Thank you, Sir, may I have another."

He said, "Tell me why I am having to punish you."

"I need to be more confident." Slap. "Thank you, Sir. May I have another."

Josh said, "What are you going to do differently?"

"I am going to be more confident in myself." Slap. "Thank you, Sir. May I have another."

This time he jerked off my little thong panties. I thought I heard them tear. He rubbed my red ass. He let his hand find my dripping slit. I had an immediate orgasm.

He said, "You are so hot. Your labia are swollen. I think you might like to be fucked."

I said, "Oh please Sir, fuck me. I want that nice big dick in any place you desire. But maybe I need a little more punishment. I appreciate your help."

Slap. "Thank you, Sir. May I have another."

Slap. "Thank you, Sir. May I have another."

Josh said, "Tell me what I want to hear about what you can do for us."

I said, "I will be the best Investigative Assistant the Gannon's boys would ever want. I can do a lot of things for you."

Josh said, "Good. Your ass is red enough."

He picked me up and sat me on the couch. He kissed me deeply with my knees on either side of him. I felt his hands fumbling to pull the top off my swollen breasts. As he kissed me I felt his hand take both of my big sensitive breasts in his hands. He squeezed them with his tongue deep in my mouth. He kissed down my shoulder blades, down my chest and finally found my hard-red nipples. I had my head laid back of the couch, eyes closed, and enjoying every touch of my body.

His hands drifted to my swollen cunt-lips. As he nibbled first one nipple and then the other, he stroked my wet swollen labia. I wanted that beautiful dick buried in my pussy but in the meantime, this was giving me the nicest small orgasms. I was moaning.

He had the little skirt at my waist, with multiple finger in my vagina, one focused on the clitoris, he was kissing and sucking on my stomach, navel and Mons Pubis.

His mouth replaced his hands on my clit. I said, "Oh Sir. Oh, my Sir. Oh, my gawd that feels so good. Thank you for that nice orgasm."

He spent a lot of time eating me until I just couldn't stand it anymore. I said, "Please fuck me, Sir. I want your beautiful dick so badly."

He stopped, looked at me in the eyes, stood and said, "Undo my pants and you can have it in your pussy."

I smiled at him, undid his belt, unzipped his pant, pushed them to his knee, and grabbed his hips and pulled him into me.

I was wet and ready; the whole thing went in with one smooth move. I had gotten good at taking these big fat dicks like Jake and Josh.

Josh said, "Melons, that is one tight wet pussy. It feels so good to be in there."

We kissed deeply as Josh had his penis buried deep in my cervix. I had a large orgasm even with him being still. I almost passed out. The room went dark and I almost forgot what was happening.

As I was coming to I heard a deep rumbling sound that said, "Josh boy, I see you are busy. I will come back."

I jerked a little as Josh said, "Melons this is Del. Del this is our interviewee Melons. Melons why don't you give Del a blow job. That would be a good start on the interview."

I said, not exactly knowing the person who said it, "Del let me see that thing of yours. I am sure I can take care of you while Josh does me."

Del removed his pants, stood on the couch with his legs on either side of my face and said, "Here you go baby. Josh, do you like that ass you are seeing."

Josh said, "It is as ugly as Melon's melons are beautiful. I will try not to look."

I think Del must have been watching for a while as he was already hard. He had an average sized penis and easily fit in my mouth. Josh now started pounding my pussy as Del fucked my face. I really didn't have to do anything but take one dick in my mouth and the other in my pussy.

Del said, "Gracious this slut can really suck cock. She could sure suck the rust off of iron. I see why Jake is interested in having her here."

Josh said, "She has many talents."

For some reason, this crass talk about me was turning me on, I put my hands on Del's hips to stop him to say, "I also have a nice tight ass that knows how to appreciate a dick. I love it all. Del your precum tastes sweet."

Josh said, "Del, I always knew you were a sweet boy."

Del said, "Kiss my ass boy. You are right there anyway."

I said, "Boys, concentrate on giving your slut all the jizzum you have. Oh, my gawd, I am having so many orgasms."

I started Del's hips moving again.

Josh said, "Melons I am ready to cum. Have a nice orgasm with me."

I started feeling his dick getting a little larger before I felt the explosion deep inside me. I had another near passing out orgasm.

When Josh finished, Del said, "You said your ass was available too. I think I will try that out." He jumped down, turned me over, took some of Josh slick residue from my pussy, forced it into my tight hole, and shoved in his dick wet from my saliva. It went in easily. He wasn't nearly as large as Jake and Josh, so it slipped in easily. All the work I had done with the anal plugs was paying off.

Del said, "Gracious girl that is one tight fit but you are right. That ass of yours knows what to do. My little dick slipped in like it was a tight pussy."

I said, "It feels good in there. Slide that dick of yours in and out slowly and I will show you talent."

As he started a slow in and out motion. I matched it with a loosening and tightening of my anal muscles. After a few strokes, Del said, "Holy shit girl. You are milking my dick like the udder on a cow."

I knew he couldn't take this long. I put my hands between my legs to give myself an additional orgasm. Josh was sitting beside us now, playing with my nipples giving me additional stimulation.

I said, "Oh yeah, Del, fuck that ass like you like it."

He said, "Holy shit girl. I can't give you anymore. Del just can't hold out any longer. I am going to fill your dirty asshole."

I said, "Del, fill this dirty girl full. I want your spunk running out of my ass."

Del said I thought loudly enough for the whole building to hear, "Take that, take that. I am pumping that lovely ass of your full of Del sperm."

I said just as loudly, "Oh yeah baby, I want all that."

Del shot several streams in me before he pulled out with a pop. I then felt some material wiping the excess off my ass. I turned around and sat on the couch, took first Josh's cock in my mouth to clean it off and then Del's. I realized Josh had wiped me off with the remnants of my panties.

Josh hugged me, helped me recover my nipples as I pushed my skirt over my now well used pussy.

Josh looked at my panties and said, "Well I think we have destroyed these. You can expense them."

I said, "No need as Jake bought them to start with."

Josh smiled, "Maybe Jake has some in his desk for the rest of the day." I shrugged. "Well as I said this is Del. Why don't you go with him to his office so you two can get better acquainted?" Josh laughed and said, "Well maybe a butt fuck is as acquainted as two people can get. Maybe you two should talk business. Del we need to have Melons in Jake's office at six."

Del said, "I know my decision now but sure I will answer any questions this sweet slut has for me."

I followed Del to his office, now wishing I had on panties. I sat making sure to keep my legs together and hands in my lap to keep my short skirt in place. I found out that Del was fifty-five, had been a policeman for thirty-five years and a detective for twenty. He had worked with Jake and was his partner for many years. He gave me some ideas of how I could work with him on investigations. I had to admit this was giving me some ideas of things I could do for Gannon's Security other than answering the phones.

At six he took me back to Jake's office. The door was open, Del shook my hand and told me, "Hope to see you here again. Good luck to you."

Jake waved a hand for me to sit. "Well how was the tour?"

"Very informative. I really think there is a place here for me. I know I would have to learn a lot more about the business but no doubt that I can help you. Del gave me some really good ideas of how to help grow the PI side of the business."

Jake said, "Melons, Merilee, I like the confidence. Did you lose your panties somewhere?"

I hadn't been so careful when I sat down. "Yes Sir, you said I should be nice to Del. So, I was very nice to him."

"Shit that turns me on. Don't you think I need to get something?"

"Yes, Sir I do." I got up not bothering to cover my slit. I was still high from being fucked by Josh and Del. I pulled my top down, put my arms around Jake, kissed him deeply as he kneaded my G-cups. As I kissed him I unbuckled his pants, let them drop to the floor. Jake was a commando guy. As we kissed, him kneading my tits, I stroked his hard member until it was completely extended.

I broke off the kiss, turned and bent over his desk, sticking my ass as high in the air as I could. Since I still wore the fuck me shoes, I was bent more that ninety degrees with the little skirt at my waist. I said, "Take either one Sir. They are yours."

He pushed his dick in my swollen pussy. It was till full of Josh's cum. He said, "Is that Josh cum I am feeling?"

"Yes, Sir it is. You both have such nice fat dicks that fit so tightly in my pussy. I hope it still feels good even though this is seconds. It is your pussy Sir. I hope it was okay to let Josh take it."

Jake said, "You know I am fine with that. It just shows that you want this job."

I said, "Oh my gawd, that feels so good." I wiggled my ass back and forth as his dick explored my depths. "That was such a good orgasm. Don't you want to take my ass also? It is already slick and ready with Del's cum."

Jake said, "Oh really. You let Del take your ass. No need for me to ask his opinion."

I smiled to myself and said, "I didn't want to take a chance he would say no."

Jake shoved his dick to the hilt without any resistance from my well-trained ass. I said, "That feels nice. It's all yours."

Jake said, "Del must have given you a full load. It is tight in there but plenty lubricated."

I heard someone say, "Are yawl talking about me?" I looked up to see Del and Josh at the door.

Jake said, "Yes we were." He stopped moving. I smiled at the two of them. "What is the answer?"

Josh said, "How can you say no to someone that has your dick buried in her ass."

Jake said, "You can't."

I said with elbows on Jake's desk showing off my large hanging breasts, nipples rubbing the desk top, "I really want to know if you guys think I can earn my money here. I don't want to just be a sexy slut in this operation."

Josh and Del looked at each other as if they had been asked to solve a Calculus problem.

Josh then said, "Melons, you are a beautiful, hard-working, smart and caring woman that could help this male dominated firm. But I also think you will liven up things around here and make it more fun."

Jake said, "That is all I need to hear. Now guys let me finish this delicate negotiation. I am doing my best to get us a good deal. Close the door as you leave."

Del and Josh took one last look as I smiled at them.

As they closed the door, Jake started pounding my ass again with that nice fat cock. I put my hands in my sensitive pussy. I can barely describe how it felt to have this man who was so commanding with everyone, taking my butt. I manipulated my pussy to keep it giving me stabs of pleasure. I could feel Jake's dick buried so deep in my ass that it was simulating my G-spot. Whatever he was hitting, it was making my pussy intensely sensitive. The stabs of pleasure with the stimulation from Jake's cock and my fingers was again making me cum over and over.

Jake said, "Melons, your ass is so beautiful. It now matches your chest. It has such a wonderful shape now. I love the way it shakes now when I slam into your butt hole."

I said, "Thank you, Sir. I am so happy that you like it. I worked hard for you."

He was breathing very hard and I could feel his penis expanding deep inside me. I knew that he was ready to fill me up. Jake said, "I am ready to cum."

"Sir I want to feel all your sperm in my nasty hole. I can't believe how good this now feels. It is so intimate. I want all of you."

He started shooting ropes of cum in my tight hole. I was already drenched from Del. I could feel it running out of my hole onto my legs. I didn't want it on my stockings so I spread it over my thighs to stop it from running. Jake was slumped over my back with his hands slowly rubbing my naked breasts.

Jake pulled me upright, turned me around and kissed me deeply. He said, "You are the best. Want to go grab something to eat."

I said, "No thanks, I am really not dressed for it. Plus, Mark is holding dinner for me. He wants to know what I plan to do."

Jake said, "Ok, but before you go we need to finalize on the job. Do you want to come to work here as my Investigative Assistant?"

"Yes Sir, I do. I will do a great job of you. You haven't told me the compensation."

He gave me a salary and also a commission on new business I brought in for the firm including Lutz's.

"Sounds fine to me."

"You will start tomorrow."

"Yes Sir. You won't be sorry"

Jake said, "I love the confidence. You are going to do fine."

I asked, "How do you expect me to dress tomorrow?"

Jake hit his head and said, "I am so stupid. I want to make something crystal clear. We have a professional environment at Gannon Security. Today was different. I made something very serious for us something of a game. But I don't want you to get the wrong idea. You will be Merilee tomorrow and I want you to dress in the same outfit as everyone else, slacks and one of our shirts. There is a locker downstairs for you containing a few of our company shirts."

"So, you had already decided to offer me a job before today?"

"Almost. Josh and I were agreed but I did want Del's opinion.

"Okay. It was fun. You want me to wear a bra and real panties tomorrow?"

"Yes. The shirt has Merilee on it. When we are playing you will be Melons. Understood?"

I said, "Yes Sir. I think I can still wear a bra. Maybe I will wear one with the tips cut out."

Jake smiled, "That works. We are going to celebrate your first day tomorrow night after work. I will provide that outfit."

"Sounds good. Now let me go have dinner with my husband."

We hugged and I drove home. As I drove home I was so happy with the day. The only thing that could have made it better would have been if Jake would have taken me home with him.

Dinner with Mark

I got home after seven.

Mark said as I entered, "Hi Merilee. From the looks of you it was a good interview."

I smiled, "It was. I got the job."

"Well, are you happy about that?"

"I am very happy. I think it will be a very interesting job. It is also a serious job. Jake said that I would be Merilee at work and have to earn my way in the company. I won't dress like this, a slut. I will wear this." I held up the golf shirt. "I even have to wear a bra."

Mark smiled, "Good. Want to change before we eat?"

"I am starved. If you don't mind me looking like this I want to eat."

Mark said, "Good with me."

As we ate I told him about the job. Mark was really interested. After I had exhausted this discussion Mark said, "I have a favor to ask you."

He seemed apprehensive so I encouraged him, "Mark, you know I want the best for you. Name it."

"Well Teddy has met me a couple of times for lunch. She called me today and asked me to go on a real date. She knows that we are married in name only. We wanted to have your permission before we really dated."

I laughed but realized that was not the right thing to do. "Mark, you certainly have my permission to do whatever you want. I have given up the right to judge you for almost anything except as a friend. So please go ahead. I think it is great."

"Merilee, it was really Teddy. She wanted your blessing."

"Tell Teddy that not only does this have my blessing, I am very happy that you are moving on with your life. I know it is not with me except I hope we remain friends and will always share Cherry. Let me reiterate, I only want the best for you. I am so proud that you have straightened out your life. I like you now. We do have one problem or I do. How are we or I going to explain this to Cherry? I mean I preached to her about not trusting boys, stay a virgin, dress a certain way and all that stuff. Now I am going to have to tell her, forget all that. It is okay that I am a slut."

Mark said, "I will help you. Between the two of us, I think we can explain it to Cherry."

I said, "It will be hard for me to explain something I don't understand."

We spent the rest of the evening planning for Cherry's return Friday night.

My first day at Gannon Security

I came to work dressed as Jake had commanded. I did wear one of the cut-out bras. I wanted to remind myself I was still a slut. But it was a very serious day. I worked very hard with mainly Del and Josh. But I did see Jake several times during the day. At six, I went to Jake's office where he was waiting.

He said, "Well, how was it?"

"I have a lot to learn but I feel very good about it. No doubt, I can help with a lot of the office work and organization. The computer stuff Josh showed me will take some training but I will get it. I am most excited about working with you and Del on investigations."

"We need to concentrate on getting more of that type business. I have heard officially that we have the Lutz business. Papers are to be signed tomorrow. With Lutz's business, we will get to a scale that attracts larger client. It really is a game changer. Josh is so excited."

"Oh, Jake that is great," I said as I jumped up and clapped my hands. I rushed over to jump in Jake's lap to give him a big hug.

He whispered in my ear, "We couldn't have done it without you. I am taking you to a romantic evening at Costello's Hideaway. I think you will like it. We can play. You can be Melons tonight."

"But I don't have the right attire to be Melons."

"Look hanging there." He pointed to a dress hanging in the corner. "We have reservations at seven. How long do you think it will take to get ready? The locker room will be empty if you want to shower. I am going to change shirts and put on a jacket."

"About thirty minutes. I stocked up my locker with toiletries this morning."

After talking a little about the Lutz deal, I went to the locker room with the dress and shoes. The dress was a red draped halter style mini dress. It was made of a stretch material that was tight around my hips and barely covered either the top or bottom of my ass cheeks in back. It hit about three inches below my crotch. The top had a tiny strap that went around my neck, attached to metal rings about half way between the start of my cleavage and where my tits naturally hung. The halter was loose-fitting that barely covered my breasts and gathered and draped at the waist. No way to wear a bra. The back was completely bare. The front cinched below my navel. Bending over showed the entire breasts. No underwear came with the outfit. I was glad that my G-cups still had their own shape and didn't just drupe to my waist. He also had a pair of red stilettos pumps for me.

I topped the outfit off with some blood red lipstick.