Madison's Changing Life Pt. 11

I woke up on Saturday feeling horny immediately. Unlike other days where I had regret, hatred or was confused on what my life had become, today I woke with a smile and a wet pussy. The events of the day before, the experiences with Jess, the bathing suit, just overall feeling slutty and sexy, it was starting to change how my mind worked.

Jess's panties laid beside my head and I picked them up again and sniffed them, taking a deep breath, savouring Jess's pussy scent. I loved it. I didn't want to love it, but I did, and I was starting not to fight it anymore.

I looked at my bedside clock and saw it was already 10:30am which was a lot later than I normally slept in. My hand grabbed my phone and I opened it up. Part of me hoping there was a message. I could feel my fight slipping away as I was getting more and more turned on. I didn't want to like what was happening, but it was hard not to. The fear of getting caught made me so excited even though I knew it would ruin my life. It was a sick and twisted way to think, but I couldn't help it. I knew I still needed to end this, to figure out a way to stop doing what I was doing, being forced to do, but it was getting harder to fight, and easier to give in. I hated myself.

To my excitement, or dread, there was a message.

Message: REMEMBER YOU NEED TO BE PUNISHED FOR CUMMING

Message: DID YOU FORGET SLUT?

I had forgotten. I forgot all about it.

Message: OPEN PACKAGE 8 AND WEAR IT ALL DAY

Message: HAVE FUN WHORE

God, the way the asshole spoke to me pissed me off so much. But the words slut and whore made my pussy twitch. It was such a frustrating mix of emotions every time I saw a message pop up on my phone.

I assumed package number 8 was some piece of clothing, but there was only one way to find out. I got out of bed and walked over to the pile of packages still laying there. After finding the one labeled "8" I noticed it had something hard inside. There was no way it could be clothing. My hands ripped it open and a large black butt plug fell out onto the ground. I gasped.

I bent down to pick it up and looked at it closer. It was big. There was no other way to describe it. It wasn't one of the little tiny ones you see some girls wear, this was at least one and half, maybe two inches wide. I held it in my hands as I inspected it. I moved it up closer to my mouth and licked it. I couldn't help myself. Having it in my hand turned me on so much. I ran my fingers along it before slipping it into my mouth, running my tongue over it. I moaned out loud which shocked me. I was so horny.

In the shower I let the water wash over my while my hand gently rubbed my pussy. The butt plug sat on the shelf in front of me, staring at me, ready to be used. Soapy water cascaded over my tits and down my ass. I reached around and made sure to play with my ass a little, sliding a finger, and then two into my hole. "Mmmmmm" I moaned as I slowly fucked my asshole with my fingers. It had been awhile since I played with my ass and doing it again made me feel like a slut. I loved it.

I grabbed the plug off the shelf and spit on it before bringing it around to my asshole to start to push it in. It was too big to just push in all at once, I had to work at it. I pushed a little harder with each stroke, moving it in and out of my ass. My other hand started to rub my clit as the plug moved further and further up my ass. It felt so good, so amazing, "oh fuck yes... fuck your ass you little slut," I said while continuing to push harder.

The toy was almost in as I was getting closer to cumming. I slipped two, then three fingers into my cunt while my other hand continued to push the toy deeper. I could feel the end of it start to slip in, it was stretching my hole nice and wide, just the way I liked it. My fingers rammed themselves into my cunt as the plug slipped all the way in. I let it sit there for a second before pulling it out. The best part was feeling my sphincter open and close around it. I started to fuck my ass with it while I fucked my cunt with my fingers. "Oh fuck... Oh fuck... god I'm such a fucking whore... oh shit... I fucking love it... I fucking LOVE FUCKING MY ASS," I yelled out as I got close to cumming. I kept working my fingers and the plug into my holes harder and faster, "fuck, fuck, fuck..." I kept saying right before the toy slipped in for the last time, my cunt spasmed, my body shook, I had to hold myself up against the wall so I didn't fall. My breathing was heavy, I was sweating somehow in the shower, my balance was off. I felt amazing.

As my mind cleared I stood back up and cooled down. Why was I being like this? Where was the conservative teacher I used to be? I knew that I always loved stretching my holes, but it never controlled my life. Now everything to do with being a slut was somehow becoming the main thing I thought about. It was taking over. Cumming in the shower wasn't bad, but the fact I did it while thinking about being blackmailed, and using a butt plug my blackmailer sent me made me shiver with disgust and lust.

As I got out of the shower I felt the plug move in my ass. Each step I took it moved up and down just slightly, but enough to make me notice it, and every time I noticed it it turned me on a little more. I looked over at my desk and noticed my laptop was still open, the green light was on, I turned and bent over a little, showing the blackmailer my ass. I wasn't sure why I did it, it just happened. Was I showing off to them? Was I enjoying it more than I would admit? I didn't want to think about it.

I put on a pair of panties and jeans. I knew the jeans would keep me from touching myself, unlike a skirt or a dress. I had to plan ahead. I threw a bra and t-shirt on and headed downstairs. Both Sam and Emma were already up and sitting in the kitchen having some toast and cereal.

"Hey guys," I said as I walked in heading to the fridge to get some orange juice.

"Good morning mom," Emma said before she got up and gave me a hug. It was weird, but nice. I wrapped an arm around her and hugged her back.

Emma went back to sit down and finished her food. My eyes watched her ass in her dark red leggings. I hated myself. She turned her head and smiled at me, I smiled back, hoping she didn't notice.

"So... what is everyone's plan for the day?" I asked.

"Oh, well I am actually meeting some friends at the mall today... could I borrow the car? Or can you give me a ride?" Emma asked.

Going to the mall actually sounded like a good idea. It was the weekend, and why not treat myself a little? Why not try to do something to take my mind off of everything that had been happening? Of course as soon as I moved I felt the plug in my ass and realized there wouldn't be much forgetting about things today.

"Ummm maybe I'll go to the mall too actually... I could use some new clothes... Sam, do you want to come?" I looked over at Sam at the table, "you can get whatever you want... on me..."

He looked up at me, "Oh... ummm... I guess... sure..." he was uneasy, but it was good that he agreed to something.

I grabbed a bowl and poured some cereal and sat down between Emma and Sam. It was a nice family moment even though no one spoke. I felt the plug push further into my ass as I sat there, I moved around a little, feeling it dig deeper and deeper. I loved the way it felt. I wanted to pull it out and push it back in again, over and over, but I couldn't. That is why I wore jeans.

Emma got up first, her loose sweater lifting a little showing off her midriff, "I'm going to go and get ready... can we go soon?"

"Sure, whenever you're ready," I said as I took another spoonful of cereal. I assumed Sam didn't need anytime to get ready.

Within a few minutes we were all in the car on our way to the mall. Emma leaned over closer to me while I was driving.

"Mom... just so you know... I'm still thinking about... you know... and... I think I might have a plan... maybe... I'll let you know..." she whispered.

I looked over at her and smiled, not wanting to draw attention from Sam, I mouthed "thank you" in silence.

The rest of the drive was silent, and when we got there Emma went ahead and met up with her friends. Sam and I walked in together, him in his tight jeans and t-shirt, and we walked through a couple of stores. I looked for some items, shorts, jeans, shirts, and he went off on his own. The problem was every time I did anything I felt the plug move in my ass, and everytime it moved the hornier I got, and the hornier I got the sluttier the clothes I wanted to buy. I started off with jeans and sweaters and was now looking at lingerie and spandex shorts. All I wanted to do was push my jeans and play with my cunt, but I knew I couldn't, I was trying to convince myself that I didn't want to either, but I knew that was a lie. I had to find Sam to distract myself.

It took me a few minutes but eventually I found him, but not where I thought I would. Sam was browsing in the teenage girls section. My initial reaction was surprise, but it made sense based on everything that had happened. I just wanted him to be happy.

"Hey Sam... how's it going?" I asked in a loving tone.

"Oh... hey mom... I'm just..."

"It's OK Sam... you can get whatever you want... just be... you... OK?" I smiled.

"OK..." I got a little smile out of Sam.

He had a pair of girls jeans in his hands, and a couple of t-shirts. I wondered if he wanted to go further, but wasn't sure if he should.

"Hey... honey... what about this?" I held up a black pleated skirt, a little nervous about what he would say.

Sam walked over and touched the material, a good sign. "Do you think this would look good on me?" he asked, I was surprised he opened up to it so quickly, but happy nonetheless.

"Yes, of course Sam, I think it would look amazing on you!" his skinny frame meant a lot of the clothes would look good on him.

Beside us was a display of different panties, 5 for $15, all piled together. I started to rummage through them picking up ones I thought would look cute on Sam. It felt a little weird doing this for my son, but at the sametime I was feeling extremely progressive.

"Hey, why don't you try these on too?" I said as I passed him a handful of panties. His face blushed right away.

"Thanks mom..." he said in his usual shy tone.

I followed him as he walked to the change rooms. It wasn't very busy so he didn't have to worry about too much embarrassment. I sat outside, feeling the butt plug dig deeper into my ass again and waited for him. My phone rang in my bag, it was odd because almost everyone texted me. I dug it out of the bottom of my purse and saw it was Tina.

"Hello?" I said as I accepted the call.

"Hey Madison... how are you?" Tina said with a little tremble in her voice.

"Ummm... I'm good... how about you?"

"Oh... well... you know... anyway... I was wondering if you'd like to go out tonight? Maybe to a club?" Tina was definitely nervous and I knew why. It was obvious she was told to make this call. I played along as if I had no idea why she was calling, but I was also curious as to why the blackmailer would want her to invite me to a club.

"A club? Tonight? Wow... I haven't been to one in so long... ummm... ya sure... why not! It sounds like fun actually!" It was the truth, it did sound like fun. I haven't been to one in a long time and maybe letting out a little bit of steam would be good for me.

"OK... awesome... ummmm how about I pick you up around 9 tonight? Is that OK?" Tina asked.

"Yes, sounds perfect Tina, I can't wait!" I said excitedly, "see you tonight."

"Bye Madison, see you tonight," Tina ended the call and I put my phone back into my bag. I didn't know exactly what was going on, why she invited me, or what the blackmailer had planned, but I was excited all the same.

My phone buzzed and I dug it out again. This time it was a text from the asshole.

Message: TINA IS GOING TO ASK YOU TO GO OUT TONIGHT

Message: SAY YES

I replied right away.

Me: I already did

Message: GOOD GIRL

My pussy throbbed when I read the words 'good girl'. Was I being good? Should I have said no? Did I fall into some kind of a trap?

Message: WEAR PACKAGE NUMBER 9 WHEN YOU GO

Message: AND CHECK YOUR PHONE WHEN YOU ARE THERE

Message: HAVE FUN SLUT

Fuck. I hated this fucker, but at the sametime my pussy was dripping inside my jeans. I was falling apart. I was starting to like being told what to do and it was killing me. How did I let this happen? How did I let my lust take over from my rationality? I needed to find a way to get things back to normal, but I didn't know if I ever would.

Sam opened the curtain and walked out wearing some jeans and one of the shirts he had grabbed. They looked great on him like I knew they would, but what I really wanted to see was the skirt, I wanted to see him in what I knew deep down he wanted to be in.

"They look great honey... but... why don't you try the skirt?" I said in the most loving tone I could muster.

He smiled and re-entered the change room. I waited patiently, my mind thinking about seeing Tina tonight, wondering what she would wear, thinking about how sexy she was, and of course wondering what the blackmailer had planned.

Sam opened the curtain and came out, this time wearing the black skirt. It was short on him, ending higher than mid-thigh, I could see his black boxers reaching down below the bottom of the skirt. He gave me a big smile.

"So what do you think Sam?" I asked, looking over his outfit again.

"I really like it... it feels... right..." he said with a smile. It was nice to see him smile.

"Well, why don't you try it on with a pair of the panties I picked for you? It will look better without your boxers showing," I said completely serious. It would look better, but I don't think he was expecting it.

"Ummm... OK..." he said a little unsure as he returned into his room.

A few more moments passed, and a few more thoughts about tonight flew through my head, before Sam came out again.

"Wow... much better," I said immediately as I looked him over. Now I could see his thin legs go under the skirt without the boxers. Suddenly I could see the femininity. If I just saw his legs and the skirt I would have thought he was a girl. "You look amazing Sam."

Sam spun around letting the skirt move and wave, a big smile on his face. The longer he stood there the more I noticed something not quite right though. At first my mind couldn't quite figure out what it was, it wasn't something I'd seen before so it wasn't obvious, but eventually I realized he was getting hard under the skirt. I could see it raise a little in the front. I wasn't sure if he knew, or if he thought it wasn't noticeable. I didn't want to say anything, I didn't want to embarrass him, but at the sametime I thought he should know.

"Sam... why don't you show me the panties you have on..." I said. I knew if he showed me it would be obvious.

"Ummmm what?" Sam said, clearly not sure what to do.

"Oh it's OK honey, just show me, I've seen everything before... remember?", as soon as I said it I knew it was a mistake, he blushed right away, memories of me catching him springing up in both of our heads.

"No... it's OK..." he responded softly, clearly embarrassed, the thing I was trying to avoid.

"Oh no... please honey... I promise it will be OK... I won't say anything..."

Sam spun around so his back was too me and lifted the skirt, showing me his ass covered in a pair of pink lace boy shorts. Again if I didn't know it was him, I would have thought it was a girl for sure.

"OK Sam... turn around, I want to see everything," I said.

Reluctantly he started to turn, and while he did I heard the words, "I'm sorry" come from his mouth. I saw it almost right after, his cock was straining against the material. My face went red as I saw it even though I knew it was there.

"Oh... ummm... I see..." I tried to show some level of surprise.

"Sorry mom... I just..." Sam started.

"No... no need to say anything Sam... it's perfectly fine..." I interrupted, "but I think... maybe you should take care of that honey."

I couldn't really believe I said what I did. His face turned the brightest red I had seen, and his eyes grew big in shock. He stood there not knowing what to do.

"It's OK... just go in the change room, and you know... take care of it..." I said, trying to make my original comment seem completely normal.

Sam with the same shocked look on his face went back into the change room with his hard cock still hidden in his panties. He closed the curtain but didn't get it all the way across and from my seat I could see just a sliver of what was going on inside. I was about to get up and fix it for him but before I could I saw his cock pop out from his panties and his hand wrap around it. I sat back down, trying not to watch but it was impossible.

For the next few minutes I watched as Sam stroked his cock in the change room, his one hand holding the skirt up, and his balls still held inside the panties fabric. His pace got faster and faster as I sat there. I couldn't help myself any longer, I looked around to see if anyone was nearby but didn't see anyone, I started to move my ass around on the seat, grinding the plug in my asshole. My hand came down and I started to rub my pussy over my jeans. It felt so wrong watching Sam and touching myself, but the plug was making me do crazy things, I just couldn't control myself. I was so horny I wanted to cum so badly. It was taking everything I had not to undo my pants and just fuck myself right there. My only saving grace was that Sam finished quickly. I watched as his cock erupted with spurts of cum onto the mirror in front of him. It started to slide down the mirror slowly and then I saw him get down on his knees and start to lick up his own cum from the mirror. I almost fell off my chair which was good because now his head was lined up with the curtain meaning he would have seen me. I quickly got up and walked away, my head spinning, just before he could see me.

I never would have imagined Sam doing something like that, but maybe I should have after I found him masturbating. My mind was completely oversexed. It couldn't handle anymore sexual thoughts, between Emma and Jess and the blackmailer, and now Sam, I was going crazy.

Sam came out of the room looking a little sheepish but I said nothing. I paid for the clothes and we headed out and back to the car in silence. I knew that Emma was getting a ride home from a friend so Sam and I left. The silence continued on the ride home, Sam clutching his bag and my eyes staying focused on the road ahead.

We rolled into the driveway and I finally felt I needed to say something.

"Sam I had a lot of fun shopping with you today... and you know... don't worry about what happened," I reached over and hugged him.

"Thanks for clothes mom," he said before opening the door and retreating inside. I followed soon after, heading up to my room.

I took a nap and a shower, the butt plug in my ass the entire time, my mind fighting with thoughts. When I woke up I heard some girls talking downstairs and assumed that Emma just invited some of her friends over from the mall. It was already 8pm when I got up, I knew it would be a long night so any extra sleep was an added bonus.

I sat at my desk and did my makeup, spending a lot more time than I usually would, it wasn't every night I went out to a club. I was looking forward to a night out, dancing, drinking, maybe letting loose a little. And I enjoyed spending time with Tina, so it was bound to be a good time. I had no idea where we were going, but I assumed the blackmailer picked the place anyway. Or maybe they didn't? It didn't really matter.

Now that my makeup was done I went over to the packages that were left and picked up number "9". My bathrobe wrapped around me, naked underneath except for the plug. I ripped it open and out flew a few different items. I reached down to pick them up and removed the contents from their own plastic wrap.