Trailer Trash

I hope you enjoy this story. This part of the story is being told in Merilee. There is a little rough sex in this story. If that offends you, you may want to skip this story.

Edited by DRGriffin

Mistress Sid takes me to buy outfits to her liking

The following morning, I awoke nude, with crusted cum, snot, sweat and tears over my body. I got to the bathroom before Mark was awake from his drunken sleep. The shower felt great. It was so good to be clean. I inspected my ass for bruises. There were none. My ass was still smooth and skin perfectly white. I called Mom and asked about trimming my pussy hair and she said to come over any time. I made breakfast for myself and Mark. He started on that day's drunk early.

I walked over to Mom's trailer. I gave her an update about the previous night's activity.

I finished by saying, "Mom I have never been so humiliated in my life. But Mistress Sid gave me two big orgasms. I never had an orgasm like that with Mark."

"What they are doing to you is similar to what was done to me. Then their father, Noah, was the one doing the damage. Sid trained under Noah. It does sound like they were harder on you than me the first time. Maybe they have evolved their techniques. What did you think of Rod's dick?"

"It was the largest thing I have ever seen. I could only get a few inches past the tip in my mouth. There must have been at least seven inches left for me and I have until Monday to be able to do it. I'm not sure it is possible for me to accomplish what they want."

Mom laughed, "Oh, it is not that hard. I don't think I did much better with Old Man Woolsey at first. He had a big one also. Want me to help you learn how to give a blow job?"

Now I laughed, "Never thought I would ask this, but would you?"

"Sure baby. Want to work on it after I do your pussy?"

"No, I have to be at the club by one. We are going shopping for acceptable clothing. They destroyed the clothes I wore last night and that was my most revealing outfit. If this keeps up I will be going over there nude. Can you come over tomorrow?"

"Sure."

I said, "Thanks."

Mom said, "Let's take care of your pussy hair. Remove your jeans. Come to the bath room. We first trim the hair short and shave what we want completely gone." In about fifteen minutes my pussy hair was gone except a well-trimmed V-shape of red pubic hair on the Mons Pubis.

When Mom finished, she said, "You need to shave every time before you play with the Woolsey's. I tell you what, let's get a wax kit and we can wax each other clean. That lasts a lot longer and is not as likely to cause razor bumps. I still like to stay nice and trimmed."

"That would be great. Mom, thank you so much."

"I will come over tomorrow to start blow job training."

I hugged Mom and thanked her again.

I had lunch, dressed and headed to the club. It was strange but I wasn't nearly as anxious and very excited. Sid greeted me in a very friendly manner saying, "Ready to try on your cocktail outfit?"

"Yes, ma'am." Sid nodded to let me know that was good.

We went to the dressing room where she showed me my locker. Next to my locker was Cherry's. Sid said, "Let's see how it looks."

"Yes, ma'am." I got undressed in front of Sid.

Sid smiled, "I see you followed my instructions. Bernice?"

I said, "Yes, ma'am."

I put on the outfit. It fit nicely but it was cut more severely than the others. While I had more tit flesh than most, I was sure mine was scoped lower than anyone else's. The areola was covered but barely. The U neck opening was cut to show the entire top half of my breasts. The strip between my legs was barely an inch wide. I would have to be careful, even wearing fishnet pantyhose or my pussy lips could show.

It wasn't quite slutty but definitely provocative. After last night, I wanted to be flexible about this. Sid said after giving me a moment to look, "I like it. What do you think?"

"Mistress, I think whatever you do."

"No we are not playing now. Can you wear this while serving drinks?"

I thought how to answer and decided I could but said, "It is more provocative than I have seen other girls wear. I would be more comfortable with a more modest look."

Sid smiled, "Well you are going to get more tips with this outfit. If you allow a little touching you will clean up. Let's try it tonight and if it doesn't work then we will modify it. Okay?"

I decided I could do it for one night anyway. After all who would see me anyway. I said, "Yes, ma'am."

Sid smiled a brilliant smile, "Excellent let's go shopping."

"Yes, Ma'am."

"Good, I will be waiting for you at the front door."

We walked down the street from the hotel bar. We stopped in front of a gym, named Just Press. Sid said, "You have a membership to this gym. There is a personal trainer, named Regina, who is expecting you. I will send her contact info to your phone. I want you to have a larger better shaped bum and a flat stomach. She knows how to shape it plus you need to be in good shape for the next few months."

"Yes, ma'am."

We came to a small clothing store called Elsa's. A young sales person greeted us. Sid said, "We want to see Elsa."

As she walked away Sid said to me, "You are to do what Elsa tells you. She is my very good friend. Do you understand me?"

"Yes ma'am."

"You need to be a good slut and make up for the poor performance from last night."

"Yes, ma'am, I will. I will make you proud."

As she slapped me on the butt, she said, "Good girl."

Elsa came up to me directly, hugged me, pressing her huge breast into me and said, "This must be Merilee. Good to see you, my dear Sid." Elsa was probably close to sixty and large. She was wearing a black leather bustier pushing up her amble breast. She was probably a 40D. Big in the waist and hips. Over the bustier she wore a pleated white lacey skirt. She had goth tattoos over her chest and arms and obviously wanted to display them. She was oddly sensual. She stepped back and said to Sid, "She is pretty, isn't she? But she sure does try to hide it. Dear, is this what you usually wear?"

I said, "Yes, ma'am." I wanted to tell her my best outfit had been torn off me the night before.

Elsa had a broad friendly face, big smile and large blue eyes. Her hair was spiked and platinum. She frowned a little, "Do you want to look attractive?"

"It really hasn't been a priority. I have had to concentrate on raising my daughter. I do want to make, hum_." I was stuck. Did I say Mistress or Sid?

Elsa came to my rescue, "You would like to make Sid happy."

"Yes, ma'am."

"We can do that. Let's take our time to get you a couple of acceptable outfits today."

Elsa and I walked around the shop, where she showed me many different options. There was one dress I liked and I thought maybe would be to Mistress Sid's liking. Elsa picked out a couple of very slutty outfits. At least, I thought they were slutty but no more so than what Elsa was wearing now. I was beginning to readjust my opinion of slutty.

Elsa showed the three outfits to Sid and she nodded yes. I saw four or five customers in the shop and the sales person who greeted us. Sid grabbed my arm to whisper in my ear, "Do what Else tells you."

"Yes, ma'am."

The fitting room was larger than most. There were mirrors on the back and side walls. There was a large couch also. Elsa hung the outfits on the wall hook and said in a much more commanding voice, "Remove your clothes."

After I had my clothes off Elsa stood in front of me, we were almost the same height but she must have outweighed me fifty pounds. I had my head bowed, she took my chin and raised it to look in her deep blue eyes and said, "You are a beautiful female. You just don't know how to use your beauty."

I said, "Thank you, ma'am."

With her hand still on my chin she leaned in and kissed me very deeply. She said, "Look dearie, I love men. By that I mean I love cocks. But there is nothing wrong with enjoying a nice little orgasm from a woman. Sid has told me to give you an orgasm that she can hear. That is what I am going to do. My advice is to enjoy it. By the time Sid is finished with you will know how to please a man but will also like messing around with someone like me. Understand?"

"Yes ma'am, I understand. Please give me an orgasm. I have thought of nothing but Sir Rod's large beautiful penis since last night."

"It is worth remembering but nowhere the largest you will experience. He can fuck and on a few occasions, I have been privileged to have him buried in my slutty pussy. Mistress Sid told me to do this. I am already getting wet. Are you?"

"Yes, ma'am, I am very wet. Would you kiss me again?"

She kissed me again, this time French. She pressed a finger in my vagina. She released me from the kiss and said, "Dearie, you are very wet. I think you came in here wanting an orgasm. This will be easy. Remember Sid wants to hear the orgasm. It is your way of thanking her."

"Yes, ma'am, I will be loud."

She bent to kiss my nipples as she stroked my labia. I lubricated her hand. After she nibbled on my nipples for what seemed like five minutes, she took her other hand and lightly pinched my left nipple. "Dearie, you have the prettiest tits. They are so full and on your slim body are magnificent. They stand up well for such large jugs while mine if not in this harness would fall to my waist. Do you know how attractive you could be?"

I said barely able to breathe, "No, ma'am. I don't know much about sex."

She whispered back, "Hang around Sid and you will find out a lot. I bet you would like your nipples pinched hard. Wouldn't you?"

"Yes, ma'am. Oh, please pinch my nipples. Please ma'am. Oh, gawd your finger feels so good there."

She had moved one finger to my clitoral hood and found my elongating pleasure spot. She then pinched my left nipple hard. I screamed loudly, "Ohhhhhhhhhhhhhh."

She whispered to me, "Good girl. You liked that didn't you. I think Sid may have heard you."

"Yes ma'am. Please do the other."

She moved to my right nipple. At first, she stroked it gently. Her finger was slowly masturbating my clit. With any additional pressure, I would have exploded. I think she knew she had me but wanted to make it last longer.

She then squeezed my agitated nipple. This time harder than the first. The pain seemed to enhance the pleasure she was giving me with her finger. Elsa, put her index finger and her thump around my sensitive clit and rolled. The orgasm had started but it would last. I said loudly, "Oh my, thank you. Thank you. Ohhhhhhhhhh...!"

Elsa pinched my left nipple causing my orgasm to reach another level. Elsa whispered, "Thank Sid. Make it loud."

I said at what I thought was a loud volume, "Oh gosh, gosh, oh gosh. Thank you Mistressssssss...!"

Elsa continued to roll my clit between her finger and thumb while kissing me on the lips. My legs were shaking and barely able to hold me up. Elsa placed her free hand on my back to support me and pulled me into her. As the orgasm subsided, Elsa guided me to the couch and let me sit down. She gave me one more peck on the cheek as she stood over me. "Now that wasn't so bad was it."

My breathing was beginning to get under control as I barely got out, "No, ma'am. I mean that was a nice orgasm. Thank you but I am so embarrassed. Not sure I can walk out of here."

"No choice, now let's show Sid how good you will look for your next session."

The outfit started with a shelf bra which was a triangle that fit under my breast and attached to the shoulder straps in a triangle surrounding the nipples. The band under my breasts was a one-inch leather strap. It was surprisingly comfortable while hiding very little. Then came the garter belt. It was also a one-inch black leather strap with a clasp. She adjusted it to strike at the navel. Attached were leather garter straps in front and back that dangled to mid-thigh ready for stockings. It had a one-inch leather strip at the buckle that covered to just past the Mons Pubis. There were two elastic bands that fit in the crease between my legs and pussy and attached to the belt in the back. This left open access to my crotch and ass crease. She gave me some black lacy stockings to put on.

The skirt was black pleated pin stripe that struck me about two inched below where the belt struck and ended about half way between my crotch and the top of the stockings. The top was a vest made of the same material as the skirt. It had a strap that buttoned at nipple level allowing a one inch opening for my cleavage to be seen completely. It was cut away at the strap in such a way that the leather band of the bra could be seen and all my stomach was visible. The arm holes were large enough so that the sides of my breasts were visible. Since the bra pushed my breast up and out both sides, the exposed flesh was accentuated.

Elsa turned me to the mirror and I had to admit it was sexy. I had never worn anything like it. Elsa asked, "What do you think of this?"

I took in a breath and said, "I can't believe it is me. It is well, hah, memorable. Isn't it?"

"I would say so. Let's go see what your mistress thinks."

I was still flushed from the orgasm. But when I stepped out there were four women and two men waiting to see me. My face and neck turned redder. I was so embarrassed. They all gave me a grin that said they knew what had happened in the dressing room.

Elsa placed a hand on my back and said to Sid, "Well?"

"Elsa, I have never seen that before. Is it new?"

"Yes. Merilee is the first to try it. I want to post a picture. Is that ok?"

Sid said, "Sure, from the sounds we heard coming from the dressing room, I think she owes you."

I said, "Oh, why not."

The sales assistant took a picture. There was a bulletin board with other customers wearing their outfits.

Elsa said, "I think we have a winner her dearie. Let's try the next one."

Sid was half Elsa's size but she was clearly in control. She put her hand under Elsa's skirt and said, "Elsa I think you need to take your time and maybe get a little reciprocal treatment. It feels like you need it. I will wait to see the next outfit."

Elsa said as I nodded my agreement, "Thank you, Mistress."

When we got back in the fitting room, I removed my clothes without being told. Elsa removed her skirt, showing that she wasn't wearing panties. She unsnapped just enough buttons on her bustier to expose her nipples. She sat on the couch. I could now see that the pattern on her chest was spider webs over each breast with the center of the web being her big areola. The flesh of her breast was so liquid that it rippled just from breathing. Her pussy was completely bare.

I said, "I don't know what to do so please tell me. I want to please you."

Elsa smiled, "We will both please your Mistress. Let's start with a kiss and fondle my breasts."

I sat next to her and felt small. I kissed her and took a massive breast in each hand. Our breast couldn't have been more different for large breasts. Her breast had almost no shape on their own, were soft and fleshy while mine felt stuffed full. After a kiss, I moved down to suck each of her nipples. My hands moved to her big fleshy pussy lips. Again, our pussies were very different. Where her pussy was very fleshy with lots of folds and loose labia, mine was tight. When I felt it, it was all soft and fat. Where mine was hard in comparison.

Elsa said, "Rub my lips hard but don't put your finger in yet. Nibble my nipples with your teeth." I did this as she began to moan softly. "Kneel between my legs and eat my pussy lips. Squeeze my tits hard before you pinch my nipples."

While I was doing this, I couldn't help but notice my pussy was pulsing like it wanted to have another orgasm while I did this big sweet woman's bidding. When I pinched her nipples, she moaned now loudly enough for all to hear, "Ohhhh yeah, my nasty slut. Work it." Then a little softer she said, "That's the spot. Stick your tongue in there and pinch both nipples hard."

I knew she wanted some pressure on her clit. I pinched her nipples one more time and this time she screamed louder, "Oh my gawd!" I thought she was ready to have her orgasm when she opened her eyes, looked down at me and said staring me in my eyes with a broad smile, "Put your hand on your pleasure spot and have an orgasm with me. I will make the noise and you stay silent."

I smiled back, took my right hand, placed it between my legs and started humping it while I attacked her clit. It wasn't long before she screamed, "Oh dear, oh dear. Thank you, Mistress." I knew she said this for Sid. I also started having another orgasm and was happy my mouth was buried in her big fat pussy lips as it muffled the noises I was making. I kept manipulating her pussy until she stopped her shutter. I stayed between her legs until she reached down, pulled me to her and whispered, "Thank you. It wasn't so bad, was it? I know I am old and wrinkled. Hopefully, it was okay for you."

I looked in Elsa sweet soft blue expressive eyes and said, "Actually, it was very good. Thank you for letting me have the second orgasm. Not sure Mistress would like it though."

"Oh, I think she is very pleased with you today. And me too. Now let's get the second outfit on.

The second outfit was much simpler, blue mini skirt, white nearly transparent blouse and a blue bra with a large opening for the nipple and half my breast to protrude. My areolas are small but very red and my nipples can form hard elongated nubs. Both were very visible through the blouse and the blue bra could clearly be seen.

I stepped out again very red from embarrassment and flushed from my orgasm. Elsa was giving me a side hug and said, "Isn't this nice?"

Sid said, "Very sexy. It sure sounds like you girls are having fun with this."

Elsa said, "Yes, we have had fun."

She looked at me and wanting me to say something. I said, "Thank you, ma'am. You and Miss Elsa have been very good to me today. Thank you so much for the outfits."

Sid smiled, "You have been good today. I must run. Merilee, you can also have the pink dress to wear every day. I think you will have time to see Regina and still be at the bar in time for your shift. You get free bar food anyway. I will see you tonight to see how your shift goes."

"Yes, ma'am, thank you."

I tried a short sleeve pink jersey dress. It zipped up the front from the bottom. The material was stretchy and fit like a glove. It had a little extra support for the breasts meaning no bra was necessary. Without panties, there would be no panty lines. It hit me mid-thigh but had a V to where the zipper started showing some inner thigh close to my crotch.

Elsa said, "Here are some panties you could wear with it, if you need to cover up a little." It was a pink thong. I put them on appreciating the extra cover.

Elsa packaged everything up, we hugged and I went to the gym. I found Regina. She was about thirty, small, lean and muscled. She had a pair of gym shorts and a sports bra for me to wear. The shorts barely covered my bottom and the sports bra showed a lot of cleavage. I did about forty-five minutes with Regina. She had me do squats of all variety. It was clear she was mainly trying to shape my butt.

I did my shift at the bar. I thought it went fine. I received a lot of tips and got mostly complements. There were a few crass comments about my anatomy but even those were probably meant as a complement.

Just before eleven when the bar closed Sid came up and said, "How has it gone?"

"I think fine. I have made a lot of money in tips."

"You see the outfit works for you."

"Yes, ma'am, it does. Thank you so much."

She whispered in my ear, "It is not so bad being our slut, is it?"

I whispered back, "No Mistress."