Madison's Changing Life

Another day, another envelope. I had already gotten up and changed into my outfit of the day. A grey sweater overtop of a black tank top. No bra. What was the point anymore? A knee length maroon skirt flowed from my waist. I picked up package number six, the last package, and held it in my hands. It was hard and seemed somewhat large. There was no way for me to know what it was, there was some kind of inner package. As I inspected it, getting ready to open it my phone pinged.

Message: GOODMORNING

Message: OPEN PACKAGE 6 AND BRING IT TO SCHOOL

Message: DURING A CLASS YOU MUST INSERT IT IN YOUR ASS FULLY

Message: AND WEAR IT FOR THE REST OF THE DAY

Message: AND OF COURSE HAVE FUN

Why did they always have to end with "have fun"? What kind of sick game were they playing? The worst part was I was finding it fun. They had broken me and now I was almost taking part because I want to, not because I am being told to. The thought frightened me, but it was true. I hated myself.

My hands tore the package open and out fell a grey triangle shaped object wrapped in a hard plastic casing. Bending down and picking it up and I realized what it was, a butt plug. This wasn't like the one I had before and lost at the club, and especially not like the one I borrowed from Emma. This one was huge in comparison. I opened the plastic and pulled the toy out, taking a closer look. My mouth opened in shock as I felt it, it was solid with just a little give. I wrapped my hand around it but couldn't reach all the way. I clenched a fist beside it and realized it was a little bigger than my hand. Would I be able to take this in my ass? I had some large toys, I had fisted by ass before, but this? This looked big even for me. And on top of that how would I manage to do this in a classroom full of students? Suddenly I was sweating. This all seemed impossible, and I realized why it was the last package, this was the one I would fail at, this is the one where the blackmailer would take advantage and say I didn't complete my task, this was the day where my life ended.

Message: I don't think I can do this

I waited for a response. I knew what it was going to be.

Message: YOU DON'T HAVE A CHOICE SLUT

And there it was.

Message: It's too big

Message: And how can I do this in class?

I waited again, deflated.

Message: YOU CAN TAKE IT SLUT I KNOW YOU CAN

Message: YOU WILL FIGURE IT OUT

Defeated. There was no way out. It had to be done. But how?

The first thing I knew I was going to need was lube. There was no way I would be able to get this plug into my ass without it. No amount of saliva would work to get it inside. I grabbed some from my bedside table and threw it into my bag. I pushed the plug in with it, my bag bulging from the sides. It was obvious something huge was in there, but would anyone know what it was? I didn't think so. I looked at myself in the mirror, looking deep into my eyes, "you can do this," I told myself, taking a deep breath, "you can do this."

I walked downstairs with my bulging bag and put it by the front door before heading into the kitchen. Sam and Emma were already there eating breakfast and looking at their phones.

"Goodmorning," I said as I walked in and headed to the coffee maker. Of course they hadn't thought to make me any.

"Morning mom," Sam said, lifting his head slightly to look at me.

"Hey mom... I like your outfit today," Emma said. I looked at her and she gave a glance indicating she thought the blackmail was over. If only she knew.

I was trying to get my mind off of things so I tried to have a normal conversation, "so anything exciting going on today you two?" I asked, taking a sip of my finally ready coffee.

"No, not really, same as usual," Sam said, going back to his phone.

Emma looked up at me and smiled, "well I have one really boring class today... the teacher's name is Madison, ugh," she said jokingly, rolling her eyes.

"Ha ha, very funny," I said back with a little chuckle. Were things feeling normal again? They seemed to be, but I knew they were far from normal.

The rest of the breakfast had a relaxed feeling too it, it was nice, and felt right. Somehow everything was feeling more balanced than before. I tried not to think about what I had to do that day. We loaded into the car and drove to school, my bulging bag in the trunk out of the view of prying eyes. I looked in the rear view mirror. Sam was looking outside, gazing at the people as we drove by. I hoped he was OK. I hadn't been able to spend as much time with him lately, everything had been such a mess, hopefully soon I would get back to being a better mother. My eyes then shifted to Emma. She continued to dress in her new way, more slutty, more with the times I guess. Her hoodie was big and loose on her today, but her leggings were low, showing off her ass, it was clear a thong was underneath. She looked relaxed, confident, in a way I was proud.

We got to school and said our goodbyes. I took an extra second in the car so I could grab my bag in peace. I carried it under one arm as I walked in, trying to conceal the large toy hiding inside. There was no reason to bring any attention to it. As I walked through the hallways I felt like everyone was staring at me. Was it true? Maybe not, but I couldn't shake the feeling. Was it because of my shirt the day before? Maybe it was because I was dressed so conservatively today, such a change from my outfits lately? Or maybe everyone had x-ray vision and knew I was carrying a giant butt plug in my bag? I was happy to make it to my classroom.

I had planned to get it over and done with early, but I just couldn't do it. I froze. I didn't know how to do it. Before I could figure out a plan students started walking in. I got up and did as I usually did, greeting them, and starting class. I pushed the thought of the plug to the back of my mind and focused on the class in front of me.

I only had a few minutes between my two classes so I didn't have the time to plan anything again. I started feeling anxious. Was I going to leave this to the last minute? I didn't want to do that. If anything went wrong I was fucked if I did that. I couldn't leave myself open to such a potential disaster, I had to do it sooner. My third class. That was the one. It had to be. The only problem was Emma was in that class. I closed my eyes for a second trying to comprehend what I was going to do.

I heard the door open and got up again, greeting my next class of students and began as usual. This time my mind struggled to focus. I knew when I was going to make myself take a giant plug in my ass in a class full of students and knowing this suddenly made it seem real. I was feeling anxious now, scared, worried, but also determined, it had to be done.

I wish I could have done the task at lunch, that would have been easy. Well maybe not easy to get it in, but without the risk of getting caught at least. But that wasn't the instruction. I had to do it during a class, and that's what I was going to do. As my lunch period continued on I sat at my desk, my leg touching the bag holding the object. I ran through the plan in my head.

Step One: Take the toy out and place it on my chair.

Step Two: Put lube on the toy.

Step Three: Push my chair all the way in under my desk to hide it.

Step Four: Start class as usual, then change to individual studying, sit down on my chair and insert plug.

Step Five: Take a deep breath.

That was my plan. It seemed simple, but it also worried me in a few ways. Firstly what happened if someone saw the plug even if my chair was pushed all the way in? Secondly, what happened if I couldn't get it in? I couldn't bounce on it, I couldn't use my hands, I had to sit on it and wait and hope it went all the way in. That was it. And thirdly, and the worst one, what happened if someone came to my desk while this was happening? How would I explain this? How would I tell them I couldn't move, I couldn't get up? There was a lot of risk, but I had to do it. "You can do this Madison," I told myself. I looked at the clock, 10 minutes before class.

I got up and picked up my bag, opening it and pulling out the butt plug. It looked like it had grown while sitting in my bag. Next I pulled out my chair and put the plug on it. It looked ridiculous sitting there. The fact that it was going to be inside me soon seemed even more ridiculous. Finally I pulled out the lube I had brought with me and lathered up the toy making sure it was covered with enough to get me through this. I looked at the glistening giant below me and shook my head. The chair was carefully pushed under my desk and I walked to the door to see if anyone would be able to see if when they walked in, luckily I didn't think they would. I walked to the window that overlooked the school field and tried to relax for a few minutes before everyone arrived. This was my life now.

The door opened and I greeted everyone, I was hoping the smile I put on hid my extreme nervousness. I watched as Emma walked in and sat half way back, I hoped she would never find out what I was about to do. For the next while I did my usual lesson, writing on the chalkboard, explaining things, answering questions. I checked the clock, timing was running out, I had to get started or else I wouldn't have enough time.

"Everyone, for the rest of the class please open to page 127 in your textbooks. Do the reading and then answer the questions following it," I said out loud as I walked back to my desk. It was now or never.

I pulled my chair out from my desk, I looked down at the giant toy sitting there, still glistening, ready to be sat on. I moved into a sitting position, lifted my skirt up so I had access, and sat down slowly. I could feel the toy forcing its way into me. At first it felt good, the tip, the easy part, but the lower I went the more I could feel it stretching me open. I couldn't believe I was doing this. Sitting on this giant butt plug in class. Something about it caused me to get more turned on though and I slid down a little further. It was impossible to know how much more I had to go. I wanted to believe I was almost there but I could be only an inch down too. I just didn't know.

I sat there for a few minutes, waiting to see what would happen. Would I sink further, taking it all slowly but surely, or would I be stuck here, without it all inside of me? I didn't know. I could feel my ass stretch slightly over time, but I made a decision to reach under me and feel how much was left. "Fuck," I said under my breath making sure no one could hear me. I still had at least a quarter of the plug to go. I looked at the time and started to panic. I only had 15 minutes left to get the whole toy inside of me. Something had to be done. My hands both went under the desk and I tried to pull my ass apart, each hand grabbing on cheek and gently pulling, opening myself up. It worked, a little. I felt the toy slip a bit further, but not enough. I knew I couldn't bounce or move too much, it would draw attention to me for sure. One of my hands moved to my front and I started to play with my clit, it relaxed me, I slid down a little further. 13 minutes.

I couldn't hold my ass and rub my clit at the same time, I only had two hands. I thought through the options, how could I do this? How could I get it done? The worst possible idea popped into my head. I worked for a different option, I needed to find one. I couldn't. 11 minutes.

My hands emerged from under my desk and I picked up my phone. No messages from the asshole thank god. I opened the texting app and found Emma's name and started typing.

Message: I need your help

Message: Pretend you have a question and come and see me

Message: Pull up a chair beside me

Message: Act normal when you get here

I paused.

Message: I'm sorry

I looked up at Emma and watched as she lifted her phone to see what all of the messages could be. I watched her face as she read through my messages, her face changing after each one. She looked up, our eyes locked, a confused look on her face.

"Uhhhh, Ms. Edwards... can I come up and get some help?" Emma asked from her seat.

I looked at her, "yes of course Emma, come on up."

One of the boys in the class made some remark about getting help from mommy. Emma swiftly told him to shut up. Good girl.

I watched as she walked towards me, our faces locked, she was trying to figure out what the issue could possibly be. She grabbed a chair and sat beside me. I was so embarrassed. I couldn't believe I was letting Emma, my daughter, see me like this. I watched as her eyes went down to my waist, looking at my skirt rolled up, my ass exposed. She could see the bottom of the toy on the chair, but not how much was inside me. I looked at her, sadness in my eyes, she wrote something on a page in her notebook.

Her Note: WTF?

I grabbed my pen and wrote below it.

My Note: blackmailer is making me do this

She took a minute, pretending to open her book, "So I have a question about this section," she said out loud doing a great job of hiding what we were really doing. She then wrote another note.

Her Note: It's OK

Her Note: How can I help?

I couldn't believe I was going to write what I was. It was beyond crazy. I pretended to help her as I wrote something down, "well you see this is connected to part A," I said.

My Note: I need you to

I paused. I couldn't believe this.

My Note: I need you to hold one of my ass cheeks open

I looked at Emma. Expecting her to freak out. But she didn't.

Her Note: OK

Her Note: It's OK

How was she handling this so well? I felt like my soul was dieing doing this to my daughter and here she was handling everything better than I ever thought possible.

I felt her hand graze my ass as I grabbed the other side, we both pulled gently and I felt myself open up a little more, another slight descension. 8 minutes.

Emma and I made some other bullshit up about the work as we continued to pull my cheeks in opposite directions. My other hand moved to my pussy, I started to rub, glancing at Emma to see what she thought, to see how she was handling everything. She mouthed "it's OK, keep going" to me as I rubbed my clit harder.

Something about this situation was turning me on again. I felt so fucked up thinking like this. How could having my daughter involved make me feel more turned on? I felt myself slip down further again, I reached under, removing my hand from my clit to feel how much was left. I was almost there, one more little movement and it would all be inside of me. I felt so stretched out and deep down I was loving it. 4 minutes.

More bullshit talking to cover up our situation and I went back to rubbing my clit, harder and faster this time. I looked back over at Emma who was pretending to look at her text book. I glanced at her legs, they looked amazing. Wow she was beautiful. I looked at her ass up against the back of the chair. Perfection. No panty line I could see. Was she wearing a thong? The more I thought about Emma the more turned on I got. It was sick and twisted but it was working. The more turned on I was the lower I moved on the plug until finally I felt my ass touch the chair. My hand and Emma's were squeezed against the hard plastic. We removed them and looked at each other, I mouthed to her, "thank you." It felt amazing having this giant plug dug deep into my hole, I loved the feeling, the sensation, but I was feeling beyond guilty for what I was just thinking about. How could I do that?

A few moments later the bell rang. Emma got up and grabbed her things, putting the chair back and going to her desk to get her school bag. I got up from my chair and immediately felt the strange object inside me. It was awkward to walk, to move, with something so large lodged in me. I struggled to get to the door, saying bye to the students. Emma walked out last, I grabbed her hand.

"I'm so sorry..." I looked at her, ashamed.

She grabbed my other hand and held them both tightly, "it's OK mom... we can talk later..."

The look on her face was one of disappointment I think. I couldn't be completely sure, it was just kind of bland and flat. It hurt me to see her like that. Was I ruining her life? Should I just let my life be destroyed so she doesn't have to deal with my situation? The thought passed through my mind as I stood there, staring into the distance. Before I knew it my next class was entering the room, saying "hi" and sitting in their seats.

It was hard to move around the room with the plug inside me. Every step seemed to push it into a new area, I felt pressure and uncomfortableness with each step. It wasn't the most pleasurable feeling, but the mental understanding of what I was doing was. My pussy pulsed every time I thought about how dirty I was being, how much of a slut. What kind of teacher teaches with a giant plug up their ass? I tried to remind myself that it was because of the blackmailer, that they were making me do this, that I was doing this against my will, but it wasn't really convincing. Part of me loved it, I couldn't deny it anymore.

I sat at my desk until the end of class, spreading my legs slightly, sinking ever so slightly further down the toy, it was becoming part of me. Subconsciously my hand slipped under my skirt and I rubbed my pussy while my students continued to read. It felt so wrong, but so right at the same time. Before I knew it yet another class was over and it was time to go. Time to face Emma.

After a very slow and ginger walk to my car Emma and Sam were standing at the car, waiting.

"Took you long enough," Sam said, looking a little annoyed.

"Sorry, just had to finish up one thing," I said back, my eyes moving to Emma.

She gave me a look as I continued to walk a little weird. She knew what was going on, what was still inside me. Her look was as blank as before. We all got in the car and headed home. We didn't talk, it was silent, awkward, I wanted to speed home to get there as fast as possible. When we got there I quickly went up to my room. I had to get the toy out of me. To be honest it was starting to bother me, it felt like it could just be pushed out of me at any moment. I got to my room and threw my bag on the floor and headed to my washroom to work on the removal. Unfortunately before I could get there I heard a knock on my door. I straightened my skirt and went to open it.

"Emma?" I said as I opened my door. She pushed her way in and closed the door behind her.

"Mom... what the fuck was that today?" she said a little angry.

"Emma... I'm so sorry... I didn't have a choice!" I replied.

"What do you mean you didn't have a choice? You didn't have to do any of it! Especially not including me in it!" Emma said loudly, pacing around my room.

"I didn't have a choice! I swear! If I didn't do it I would have been exposed... my life... our life ruined!" I started crying as I said it.

"Ugh! Mom! This is crazy!" Emma calmed a little, my last words causing her to think about my predicament too.

"I know honey... I know... but... I think it might almost be over... maybe..." I walked closer to her, touching her arm.

"How do you know?" she said looking at me.

"Well... see... I was given packages... of things... they were left for me," I started, I could tell she was confused, "and ummmm... the thing today was the last one... so I'm hoping that was it... that it's over..."

There was silence for a few moments. I was waiting for her response, Emma was thinking through what I said.

"Are you sure?" Emma asked. A good question.

"No... I'm not... I just... I hope," I stumbled out as I wiped a tear from my eye.

"God mom... I can't believe this shit..." Emma said, a little louder again, I couldn't even imagine what she was feeling.

I gave her a hug, squeezing her tight, holding her, but every second that went past was one closer to the plug wanting to push out of me. I had to get it out right away.