Trailer Trash Pt. 03

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The Woolsey's have me take two large penises.
15.1k words
4.66
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13

Part 3 of the 8 part series

Updated 06/08/2023
Created 08/16/2017
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slimpic11
slimpic11
269 Followers

I hope you enjoy this story. There is a little rough sex in this story. If that offends you, you may want to skip this story.

Edited by DRGriffin

I tell Mark what is happening

The next morning, I was awakened by noise from the kitchen. I looked at the clock and saw that it was almost eight. I arose, looked in the mirror at my naked ass and saw no marks. My nipples were still sensitive as I touched them but there were no marks from the clamps. My ass still hurt a little and my pussy felt like I had a truck driven through it but all in all I was okay. I threw on a tee shirt and went to see what was causing the noise.

It was Mark cooking. The smell caused my mouth to water and I almost forgot about my hurting body. Mark said, "How about some pancakes?"

This was the first I knew that Mark could cook anything. I was so hungry I would have eaten anything. I said, "When did you learn to cook?"

Mark laughed and said, "I'm not sure I can yet but I am trying." I couldn't remember the last time I heard him laugh.

The tee shirt barely covered my privates but I had already decided that Mark was essentially not there. So, I sat on the stool at the little kitchen counter without concern for what he saw. He poured me a cup of coffee, ladled four pancakes on a plate and placed it in front of me. I poured on some syrup and ate a bite.

Mark looked expectantly and asked, "How is it?"

"Excellent. Where did you learn to cook?"

"Are you really interested?"

I nodded my head with my mouth stuffed full of pancake. I realized I was starved and I still needed to put on a few pounds for Mistress. Mark looked clean and sober.

"Yes, I really want to hear."

Mark stood on the other side of the kitchen counter eating his pancakes. "Well after the incident with Jerome and Bernice, I decided I had to do something with my life. Not because I think we will get back together but because I realized I was wasting my life. I also concluded that being a drunk wasn't good for anyone. So, I went to an AA meeting Thursday. I had gone for 24 hours by then without a drink."

I said still wolfing down pancakes, "That is great Mark, but please do it for you not me."

"I am. I know you have given up on me. I just appreciate that you haven't kicked me out already. I don't know what is happening to you but I promise to stay out of your way."

I felt something like, oh I don't know, maybe guilt even though I didn't have anything to feel guilty about. I decided to say, "Good, continue."

"I have gone to a meeting every day since. I know that it is only the seventh day but it is the longest I have gone for, well, ever. I was an alcoholic at sixteen. Anyway, my sponsor offered me a job as a cook at the homeless shelter. He knew I didn't know how to cook but the people down there are training me. Pancakes were the first thing they showed me. Funny thing is, I enjoy cooking. It helps me keep my mind off my problems. My sponsor said that the people at the shelter think I have an aptitude for cooking."

I said, "Mark, I am very impressed and happy for you. May I have a couple more? I am really hungry."

Mark smiled, "Sure, glad you like them."

Mark continues, "Anyway, I'll usually be at the shelter for breakfast and lunch six days a week. I won't make much money but at least I am learning something and it makes me feel useful. The only reason I am here this morning is that they want me to work tonight. But Merilee, I plan to stay out of your way. I know that I have been a bad husband. There are two steps that will involve you in the twelve steps but I'm not ready yet to take them. Just know I am sorry for the person I have been."

"Mark, I think we have to admit that we were never really compatible. I know that now. But we have shared raising Cherry. While we haven't been good for each other, we have raised an outstanding daughter. Let's be proud of that."

Mark racked two more pancakes on my plate as he said, "You are right. If there is anything I can do for you other than stay out of your way, I would like to help. It is helping me to continue living here while I am getting on my feet. I owe you."

"Thanks for the pancakes. These are very good but this is all I can eat. I think I want to explain what is happening with me. Without getting into specific details, the Woolsey's offered me an opportunity to make enough money to fund Cherry's education. Mom had done something similar for me to make it without a husband or a skill. They are paying me for some number months to be their sex slave."

Mark's jaw dropped. "Why would they even think you would accept?"

I said, "Because they knew I was submissive even when I didn't. They thought it because of their experience with Mom and we are so much alike. No matter they are right. I am submissive. Said a different way, I am a slut or a slut in training. I want to do the things they are making me do. Last night I passed the oral sex test."

"So that is why you were sucking Jerome's dick."

"Yes, but I liked it. Next Monday is the big dick test. I have to take a couple of really large penises."

"You mean larger than Jerome?"

"That is what I understand."

"My goodness, his is the largest I have ever seen."

"Me too. But I have only seen three. Rod Woolsey, Jerome and yours."

"Mine is really small, I know. You will not insult me by telling the truth. That is one of the things I am determined to do from now on. I am going to accept who I am. Is Rod as big as Jerome?"

"I would say about the same."

"So, you will have to take Rod next Monday?"

"No, he fucked me last night after I passed the oral sex test. Apparently, there are people larger than Rod and Jerome."

"My goodness. Well best of luck. I clearly can't help you with large dick practice. Is there something else I can help you with?"

"The same way I can help you. Be supportive."

"That is fair. I appreciate your support and you can count on me. I know I haven't given you any reason to have confidence in me. But I am determined this time. Shake?"

He reached out his hand. I considered hugging him but decided that might give him ideas. We shook.

Mark said, "You know I liked when you told me what to do. Maybe we are both submissive."

I said, "Maybe."

Mark smiled and said, "I need to get to work."

I said, "I like the way that sounds." Mark had the kitchen cleaned up while we talked.

After he left I looked in the bag Mistress had given me. There was a large dildo with fake balls and a suction cup base. I used a tape measure to find that it was twelve inches long and a little over two inches wide. I thought about how large Rod and Jerome were. I guessed about eight inches but nowhere close to two inches wide. I was sore from Rod screwing me one time. How could I take one much less two dicks larger than Rod?

I was so worried about being able to do what they wanted I decided I needed to talk to Mistress. I text her and asked if I could talk to her before work tonight.

I had a session with Regina. She gave me some advice how to gain additional weight in the right places. She gave me an additional supplement and wanted me to eat more.

I knocked on Sid's office door at five. As I entered, she said, "Slave stand there with your head bowed."

I waited for about five minutes before she said, "Remove your clothes, and come stand in front of my desk."

I did as she commanded, and stood in front of her desk with my head bowed. She inspected my body, touching my nipples which reacted to her touch by getting hard and standing out. She rubbed my ass where she had spanked me the night before.

Finally, she touched me between the legs and my vagina obliged her by getting her finger's wet. She laughed and said, "You are a very responsive slut, aren't you?"

"Yes Mistress, I am for you."

"Were you sore this morning?"

"My tits, ass and pussy were very sore this morning. Sir Rod's dick really stretched me. That is why I wanted to talk to you."

"Okay."

"Mistress, I looked at the dildo and I am worried I will disappoint you Monday night. I can't imagine taking two penises in one night that size."

"You will or be punished like you can't imagine. On Friday night, you will go to the Platinum Club and see Tobias. You will do a special show for at least five guys in the VIP room by taking half of the dildo in your slutty cunt in a show. You will fuck yourself with it while they masturbate on you. You will then give Tobias and anyone else he chooses a blow job. You will do what Tobias tells you to do that night. The two people you will do Monday are not as long as the dildo I gave you but have that girth. After Friday night, you will not touch your pussy. I want you tense Monday night. Understand?"

"Yes, Mistress but I could barely take Sir Rod, I just don't think I can have my pussy stretched enough by Friday night."

"Ok, I will be generous. You can have Jerome tomorrow for two hours. You will be ready for Friday night's show."

"Yes Mistress. One more thing if I may?"

"Go ahead."

"I want to do this long enough to get Cherry four years of college."

"Yes, I thought you would. You are realizing what a nasty slut you really are. Aren't you?"

"Yes Mistress. Seems like it."

"Tell you what, I am going to let you have Jerome all you want until Friday night and you can have all the orgasms you want until then. That should make it easier."

"Thank you, Mistress. I would like to fuck Jerome."

"I think you need to show your Mistress some appreciation. Don't you?"

"Yes Mistress. Anything you want?

"Give your Mistress an orgasm. Remove my clothes."

I removed her blouse. She had more muscle that breasts. She did have large puffy areola on her buffed pectoral muscles. I removed her skirt. She wore no panties. She had huge glutes and thighs. There was no sign of hair anywhere but the butch haircut on the top of her head. I assumed she had removed all her body hair via laser treatments. She was smooth, pale and hard all over. She had a tattoo of a flexed muscled arm on her Mons Pubis. The elbow touched the top of her slit.

After I removed her clothes, she sat on the couch and spread her legs. I knelt between her legs and started to lick her pussy. While I much preferred sex with men, it was getting to be somewhat pleasant to have sex with women. I thought I was getting better at it. As she began to moan, I could sense the excitement she was feeling. I focused on her clit. As I licked it elongated to show outside the hood. I took the miniature penis between my lips without touching it with my teeth. I gently flicked it with my tongue as her juices flowed into my mouth. Her moaning became more intense.

Her hip rolled up and down causing her pussy to bounce up and down on my mouth. I let her fuck my mouth like this until she said, "Oh yeah my nasty slut, that is the spot. I am ready to cum. Oh, yeahhhhhhhh."

I could feel her pussy and powerful legs contract causing her to tremble. It felt like a good orgasm for Mistress. I was pleased with myself. I didn't move until she said, "That was very good. You have been a good slut tonight. Now get me dressed before you go to work. I will have Jerome at your trailer at ten tomorrow morning and then whatever you work out is between the two of you for the rest of the week. You have made me very happy with your decision to accept our offer to help Cherry."

"Thank you, Mistress."

Preparation for the large penis test

Mark had left for work before I got up. I was excited to have Jerome to myself for a couple of hours. My pussy, tits and ass had healed. I wanted to have sex badly. I bathed, shaved and put lotion over my body. My vagina seemed to be dominating me. It was seeping.

I couldn't decide what to wear. I didn't have that many option that were sexy. Maybe just go nude. Maybe just a tee shirt, one that was very thin. Maybe one of the three outfits purchased from Elsa. Maybe just a bra and panties. I decided I wanted something he could take off. Then it hit me. I still had the negligee I wore after I recovered from delivering Cherry. It was a one night stay in a downtown hotel Mark and I called our honeymoon. I rummaged through my drawers and found it at the bottom of one.

It was a pink frilly baby doll with old fashioned panties. I put it on and looked in the mirror. The top was nearly transparent but my bottom was covered. I thought, 'You look almost like you did eighteen years ago.' Somehow this seemed right.

With a mixture of excitement and apprehension I waited for Jerome. Excitement because I wanted to fuck Jerome ever since Mom had. Apprehension because he could be my son.

There was a knock on the door. I opened it. Jerome said, "Hi, Merilee, you look beautiful."

I smiled, "This old thing?" I hugged him and kissed him deeply. He kissed me back just as eagerly.

When he released me, I lead him to the couch, sat him down and got on my knees to remove his shoes. I knelt between his spread legs, unbuttoned his shirt and pulled it off. I unsnapped and unzipped his jeans. I pulled them over his hips as he raised.

Standing I slowly pulled the top over my head.

Jerome said, "Merilee, you have the most beautiful tits."

"You think prettier than Bernice?"

"Well it would be hard to call."

"Thanks for being honest. You called Bernice Granny, call me Mommy."

Jerome gave me a sly smile as he said, "Yes Mommy."

I had placed the giant dildo on the coffee table. I said, "Baby boy, I really appreciate you helping me out. I need to get this thing in me somehow Friday night. I am thinking you are at least close to being this big around. If I can take all your real penis, then I think I might be able to take this silicon dildo."

I sat next to him. He wrapped his arm around me as we kissed again passionately. The kiss lasted. He was rubbing my chest while we kissed. My nipples were standing out already. He found them and gave each a light pinch. I moaned and my underwear got a nice spritz of moisture. Jerome moved to nibble my tits. He couldn't get enough of my G's. I knew this was making him hard. I was anxious to have him in my tight vagina.

I hated to stop his munching on my breasts. I slipped off my underwear and said, "I am ready to try out your big boy. You ready?"

Jerome said, "I'm here to help so up to you."

"Let's first try it with you on top. Take it slow so I can get used to you."

I laid back on the couch, while Jerome positioned between my legs with his hard penis ready. He lowered himself, the head entering my sopping pussy. I was so excited to have this nineteen-year-old wanting to screw me. It somehow made me feel sexy to know this. My head was propped on the arm of the couch so I could see what he was doing. When he was a third of the way in I could feel the pain of being torn apart. I put my hand on his abdomen to stop him.

I said, "Let me get used to that much before you give me more."

Jerome said, "Mommy this feels so good. You are so tight."

He lowered his mouth to my big soft breasts and kissed them all over. This helped me relax. The pain was beginning to diminish. I said, "Ok baby boy, I am ready for you to move slowly just don't go any deeper until I say so."

He started a very slow movement in and out. I felt so full as his penis. It was hitting me in exactly the right places. Before long I was having orgasms. I could see that Jerome was getting a little deeper but very slowly. Each time he pushed harder I could feel the pain of being stretched.

Jerome said, "Mommy you are so tight. I'm trying to hold out but I'm not sure how long I can. But you know I can get it back up soon."

"Baby boy, I know. Please enjoy yourself. I'm certainly enjoying you. My orgasms are almost continuous. Can you feel them?"

"Yes Mommy, I can. It feels too good for me to hold out much longer. I am about half way in now. Is it still hurting you?"

"A little but nothing like when Sir Rod fucked me Monday or when you first entered me. You have a wonderful penis. Mommy really likes it in her."

He continued to stroke me. I forgot about the task at hand and just enjoyed being fucked by this young man. I was amazed at how long he could hold out despite his excitement. I was moaning with my eyes closed. I looked into Jerome's eyes. He was staring at my large breasts rolling from side to side.

I smiled at him, "You like looking at your Mommy's breasts. Don't you?"

"Yes Mommy. I can't hold out much longer. Here it comes."

I started having my largest orgasm. I screamed, "Oh mmmmmyyyyyy. Your large shaft feels so good."

I could feel the juices running out the edges of my pussy. He must have shot his jizzum in me for at least a minute. He was hosing me very deeply, the deepest anyone had been in my vagina. He was three quarters of the way there. I was beginning to believe I could do it.

Jerome penis shrank out of me. When he sat up I stayed where I was and grabbed the giant dildo. I wanted to see how much I could accommodate already. My vagina was sopping from my juices and Jerome voluminous ejaculation. I pushed it in and the head of the silicone penis went in with no trouble. I pushed a little and a third entered without me feeling too stretched. It felt good. I was still excited. So, with the additional pressure on my clit and rubbing across my g-spot, I had a big orgasm.

My eyes rolled back in my head and I moaned loudly. After the shudder past, I looked up and Jerome smiled, "Looks like mommy doesn't need me anymore."

I smiled back at him, took the dildo out, sat up, and hugged him, "Baby boy, you feel so much better than that silicone thing. I think with a little more practice I can get it in. It is really only a little larger than you."

I kissed his cheek then pulled him into me and kissed him deeply. I asked, "Are you able to go one more time for me?"

"I have enough time to go once more. Can I have some water before we start again?"

"Where are my manners. You want something to drink? I do plan to feed you lunch before you go."

"Both would be good. I have another appointment, real tech work, at one. So, lunch with you would be good."

I fixed us both a glass of ice water. I could feel his eyes following my ass as I did. I handed him the glass of ice water and asked, "Do you think my hips are too slender?"

Jerome said, "Actually, I was thinking you are getting a little extra padding and it looks really good. Your breasts are so large a little extra booty would look sexy."

I rubbed my hands down my hips and said, "That is very nice of you to say. I am trying to add a little here." I slapped my ass cheek as I said this.

Jerome took a big gulp of water, "You have a wonderful body. I don't think I could ever get enough of it. Are you ready for more practice?"

I looked down at his growing penis and said, "I think Mommy is making you hard again just by showing off her body. What if I did this?"

I bent over at the waist, letting my tits hang down, and took his growing penis in my mouth. He cupped my hanging breasts in his hands and squeezed. It felt so good as he put more and more pressure on them. I really wanted to keep his penis in my mouth longer but realized I needed as much penis in pussy time as possible. I thought that I needed to get used to the feeling of a penis head hitting my cervix. Being able to relax was a key to accommodating the dildo in my throat.

I raised up, straddled his hips and slipped his now hard dick into my vagina. This time half of it slipped in before I thought I needed to stop. What's more it felt great. There was no pain. I had a large orgasm. My body shuddered and I made a gross feline sound.

As the tremor past Jerome said, "I think Mommy is getting used to my big dick."

I could barely talk but mumbled, "It felt so good, I wish I could keep it in forever."

slimpic11
slimpic11
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