Madison's Changing Life Pt. 02

Story Info
Madison's blackmail continues.
3.7k words
4.4
69.6k
33

Part 2 of the 18 part series

Updated 06/09/2023
Created 10/09/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's Notes: Continuing with shorter chapters. A lot more to come for Madison! Comments appreciated!

*********************

At some point during the night I must have passed out because I woke up with everything just as I had left it. My lights were on, laptop still open, and I was laying on top of the blanket on my bed. My mind started to come back around and I began to remember the horror that came into my life last night. I rolled out of bed and moved my still waking body over to my desk to check my e-mail, just to make sure that it wasn't a nightmare. To my dismay it wasn't. The e-mails were still there.

Subject: AND DRESS SEXIER

The last e-mail that was sent over last night stared at me. Now not only was I being blackmailed, but I had to 'dress sexier' while going to school as a teacher. How the fuck was I going to accomplish that?

I moved myself away from my laptop and started getting ready for the day, washing my face, makeup, brushing my hair, the usual, and then it was finally time to start to pick out my clothes for the day. I knew it had to be sexier than yesterday, but I refused to do anything crazy, so first things first. I slid on a pair of boyshort panties followed by a pair of black pantyhose and a white bra. Now I had to figure out what to put over top. My hands rummaged through my drawer until I found a white dress. It had some detail around the bottom and neckline, and ended just below my knees. It was sleeveless and shorter so I decided that qualified as 'sexier'. I also grabbed a white cardigan that I threw on to cover my shoulders. The bottom line was, I was still a teacher.

I grabbed my laptop and papers and threw them in my bag and headed downstairs to make breakfast just like I do on a normal morning. This was anything but a normal morning but I had to keep things normal for Emma and Sam, I didn't want them to know anything was wrong.

The toast went into the toaster, the jam and butter came out of the fridge and I yelled up to Emma and Sam to let them know that breakfast was almost ready. Eventually they both came downstairs, Sam first wearing almost the same clothes as the day before but a black t-shirt this time, followed by Emma. Of course Emma chose today to dress even sexier than usual. She showed up in the kitchen wearing her usual long shirt, this time a long sleeved t-shirt but she must have been wearing some short shorts underneath as it looked like she wasn't wearing anything at all. As she finally sat down for breakfast I saw the black spandex shorts come into view. Girls these days are dressed so much differently than when I was younger. It was casual and messy but somehow extremely sexy.

Breakfast ended in our usual fashion of very little talking. We all grabbed our stuff and we headed out to school again, Emma in the front and Sam in the back. My eyes kept darting down to my daughters legs as we drove. I didn't want them too but I couldn't stop myself. And then my brain would switch back to what that pervert was making me do and I just got mad again.

The school approached, we all got out and said our usual 'byes' for the morning. I walked across the school grounds and towards my class. It was another beautiful day and everyone was minding their own business. My only business right now was to get to class and try to find out where the camera was.

I walked into my classroom and closed the door and immediately looked up to where the camera angle looked like it was coming from. I didn't see anything. I looked around the whole room and I did notice a camera above my desk, but it was pointed out towards the class, there is no way it would have gotten the angle I had seen in the picture. What the fuck was going on? Then I pulled the blind down on the window of the door to see if there was some spot that wasn't properly covered, some place where a camera could poke through and take a picture. But again I just didn't see how it was possible. What the fuck!

At this point I only had a few minutes left until my first class so I opened the blind, went to my desk and took out my stuff and sat down. How the fuck was this asshole getting his pictures? How was I going to stop this motherfucker from blackmailing me further? Fuck. I just kept racing through these thoughts as my door opened and students started to pile in. For the next three classes I tried to focus on the task at hand, my classes, teaching, but as lunch got closer it was harder and harder to concentrate.

Half of my brain was mad, trying to figure out what was happening and how I was going to stop it, but the other half, the naughty half, was getting excited that soon I'd be able to masturbate myself to an amazing orgasm in my class again. Even worse, both sides knew that it was going to happen because I had no choice.

The bell rang, the students left and once again I followed the last one to the door, checking down the hall, closing and locking the door, and pulling down the blind.

"Well, here we go," I said to myself as I let out a deep breath.

I walked over to my desk and pulled out my chair like I did the day before. I sat down on it and moved forward so my ass was at the end. The e-mails said to do everything again, so I wanted to try to recreate the scene as close as possible. My hands rolled up my dress above my waist and my fingers pulled my pantyhose and panties down together below my knees. The cool air rushed up against my gaping pussy and it was then that I realized how wet I was, again. "What the fuck is wrong with me?"I said under my breath as my right hand shoved two fingers deep into my waiting hole.

In a few minutes I had four fingers ramming into me again, my left hand roughly rubbing my clit and my breathing was heavy. A few minutes after that I was cumming hard in my classroom. My hands grabbed a tissue and I cleaned up. My pantyhose and panties went back in place and my dress fell down into its original position. I looked up in the general position of where the picture was taken and held up my middle finger and mouthed "FUCK YOU".

The rest of the day went by as you would expect. Everyone else was their usual self and I was seething inside. I hated that I was being told what to do, that I was being blackmailed, that my whole life was being held in the hand of an obvious pervert asshole motherfucker.

The school day ended, Emma and Sam had something going on after school so I went home alone. I tried to distract myself by watching TV, going for a walk, reading a book, but nothing took my mind off of the situation I was in. I started making dinner in expectation of Emma and Sam's return. We ate, we chatted, they went to their room, I cleaned up, and I went to my room. If it wasn't for lunch and the asshole today would have been a regular day, a good day.

I opened my laptop on my desk and checked my e-mail expecting to see the worst, but to my surprise, there was nothing there. "Huh, maybe the asshole couldn't get a picture this time?" I said to myself as I started to unpack some papers from my bag.

An hour went by, no e-mail, then two hours, no e-mail. I was starting to feel hopeful. It was 10pm and it was about time to get into bed. I went to the washroom to get cleaned up, wash my face, brush my teeth. As I walked back to my desk after feeling so much relief I saw a new e-mail on my screen. No 'from', only a subject line. Fuck.

Subject: YOU LOOKED GOOD TODAY

"Well thanks asshole," I mumbled. Another e-mail came through. This one with an attachment. Great.

Subject: LOOK AT YOU

I clicked the e-mail and saw that this time there was no picture, but a video instead. My hand trembled while I moved the cursor over the play button. In front of my eyes was a video of me, in my classroom, four fingers deep in my cunt, fucking myself to orgasm, and the worst part of it was there was sound. It was like a deafening boom in my ears, the sound of my sloppy hole loving what my fingers were doing to it. My head dropped into my hands. What the fuck was I going to do?

Another e-mail came through.

Subject: SAME SHOW TOMORROW BUT NO PANTYHOSE

I let out a little laugh. I realized at that point that this wasn't going to be a short lived thing. The pervert on the other side of the screen obviously had some kind of plan, I didn't know for how long, but it was obvious it wasn't just for a day or two. Tomorrow would be the third day I had to fuck myself in my class room. This time without pantyhose.

I closed my laptop and got into bed. I wasn't sad, I was just mad, maybe defeated, disappointed, I don't even know, I just felt like I had lost. Maybe lost everything. I fell asleep faster than the night before into a dreamland of negativity.

***

Wednesday morning came and went. I had worn a similar dress from the day before, but this time no pantyhose as instructed. The school day went on as usual, the only difference was Sam was in one of my morning classes, but we kept a clear teacher/student relationship. Lunch eventually came, I closed and locked the door and pulled down the blind. Everything was becoming a little too routine. This was not what should be happening to me, not what should be a normal part of my day.

I sat on my chair, opened my legs, pulled down my panties and proceeded to four finger fuck myself to an amazing orgasm again. It almost felt as if each day my orgasm felt better, more relaxed, more at ease. It felt good but I hated it. Nothing was supposed to be the way it was. I cleaned up, finished the day and went home. Dinner, clean up, bedroom, every day went as expected except for the two things that didn't, lunch and late e-mails.

I sat at my desk as usual and waited for the doom e-mails to arrive, and arrive they did.

Subject: GOOD JOB YOU LOOK BETTER WITH NO PANTYHOSE

Awesome. The next e-mail came through.

Subject: YOUR VIDEO

I clicked play and saw myself fucking myself again, this time no pantyhose as expected.

Subject: TOMORROW NO PANTYHOSE AND THONG

"Fuck you pervert," I said and closed my laptop before going to sleep.

***

Thursday morning came just as the rest of the week, get up, dressed, breakfast drive to school. I did as I was told and didn't wear pantyhose, and I wore a thong. It wasn't the first time I had worn a thong to school so I didn't really mind it, the part I hated was being told, no being blackmailed to do it.

Third period eventually ended. Locked door, blind down, four finger cunt fuck, clean up, and back to normal for fourth period.

The day ended and I went home to try to relax. It was hard, I was feeling exhausted. The stress of my blackmail situation was just wearing on me. I was constantly angry, constantly worried, constantly thinking about everything. I got changed into my comfy clothes and laid down on the couch and napped until I heard Emma and Sam come through the door.

"Hey guys," I said as I got up.

"Hey mom," Sam said as he saw me on the touch, "are you tired?"

"Ya, exhausted," as I finally got up to my feet, "do you mind if I just order us a pizza?"

"Sounds good," Emma said as both her and Sam walked up the stairs.

Pizza was ordered, pizza came and we ate and chatted a little, but not a lot, just like usual. The leftovers were put away, dishes into the dishwasher and everyone went up to their rooms just like every other night. For Sam and Emma everything must have seemed normal. There was no way they could know what was going on with their mom. But for me, this was one of the worst weeks of my life, and I just had to fight through it.

I got up to my room, opened my laptop and got to work grading papers just like every other night. At this point I wasn't even worried about the e-mails, I just assumed they were coming. I was defeated and tired. It was what it was. And just like I expected eventually the first e-mail came through.

Subject: ANOTHER GOOD SHOW

"Ya ya, fuck off," I said only glancing up at the screen.

Subject: YOUR DAILY VIDEO

I clicked play mostly out of habit and there I was thong on, legs open, four fingers, cumming. I closed the video after only a few seconds. I knew what happened. I knew what would come next, tomorrow's 'task', fucker.

Subject: TOMORROW NO PANTYHOSE AND WEAR THONG

Well this was different, the same thing as today. Maybe this fucker was running out of ideas? Unfortunately I was wrong.

Subject: TOMORROW FINGER ASS NOT PUSSY

And there it was. The change. The next 'task'. I wasn't even that bothered by it. Firstly I liked playing with my ass, and maybe he didn't know that, so it wasn't really punishment. Secondly it wasn't a real change from today, same clothing, just a different hole. I could handle this. Honestly if this was the worst thing he could think of I could ride this out.

***

Friday morning came and went, breakfast, drive to school, class, three periods. It all flew by. Before I knew it, it was lunch again and time to do what I've done four other times this week. I locked the door and pulled down the blind. I positioned myself on my chair as usual, thong down, dress up, and started.

I spit on my fingers and rubbed the wetness on my asshole. It felt good. They didn't say anything about four fingers so my plan was just to put one or two in my hole and get off, nice and easy. My pussy was wet as usual. Even though I was being blackmailed I was still in my classroom doing something dirty and my pussy didn't know any better. I rubbed my hand on my cunt and then my ass making a nasty mixture of saliva and pussy juice.

I slipped a single finger into my ass and let out a soft moan. It had been a while since I had played with my ass and it felt amazing. My other hand came down and gently rubbed my clit. They said no pussy, but I hope that didn't mean no clit. I kept playing with myself, slowly pushing my finger deeper into my ass before I slid a second one alongside it. My hole started to respond to the action it was getting and relax. I planned to only put two in there to show this pervert I could control myself, but in reality I couldn't. A third finger slipped into my awaiting hole.

"FUCK," I said out loud, I knew they could hear, I knew it would be on the video, but it just happened.

My fingers started to piston themselves in and out of my hole, my other hand rubbing my clit harder and harder. My eyes closed and my head fell backwards. It was at this moment, for the first time this week it seemed, that I wasn't thinking about the blackmailer, about the pervert, about my life ending, I was just enjoying the feeling, fucking my ass in my classroom. I was loving it.

My hips started to move in my chair to match the rhythm of my fingers into my ass. A fourth slid into my hole way too easily. It was obvious to me, and would be to the person behind the camera that I was turned on, and not just a little. In and out, in and out my fingers rammed into my ass past the second knuckle. The feeling of being stretched out felt amazing. My hand pushed hard as I wanted to feel full. My other hand roughly slapped my pussy, my clit was on fire, and finally I came. Not just a regular orgasm, a massive one. I shook, I felt juices pour out of my pussy and out onto the floor. My fingers fell out of my ass as my other hand kept gently rubbing my clit. I was trying to catch my breath, trying to come back down to earth, and as my mind started to return to reality I remembered the camera, the asshole.

I started to clean up, pulling my thong back, and letting my dress fall into place. I was sweating and exhausted. I knew that the pervert got a much better show then he deserved, but I just couldn't help myself, it was what it was now, and I had to live with it.

I had Emma in my fourth and fifth period this week, and just like with Sam we kept a clear teacher/student relationship, but today I had to work extra hard to make everything seemed normal as I was coming down from a huge orgasm. Luckily I made it through the afternoon without anyone noticing how flushed I was.

The day ended and I made it home in one piece. Emma and Sam both came with me but quickly left to hang out with friends or something. They're 18, I don't ask. I had a nice long shower after they left and reheated the leftover pizza in the fridge, very glamorous.

That night I relaxed, I watched some bad TV and then a movie. I was still exhausted from the week, both mentally and physically, I just needed some alone time and to calm myself, and that is what I did. It felt good just to have a normal night, leggings, hoodie, comfy. My mind actually wasn't thinking about the blackmailing asshole for a few minutes. As the night wore on I got more and more tired and headed up to bed.

Part of me didn't want to check my e-mail, but the other half did, it was a constant good versus evil situation. I also didn't want to miss some instructions and ruin my life. What if he wanted me to do something and I didn't check my e-mail and then he sent out the pictures or videos? Not worth the risk.

I laid down on my bed and opened my laptop, and then my e-mail. "Fuck," I said as I realized there were already five e-mails waiting for me.

Subject: GOOD JOB TODAY

Subject: YOUR DAILY VIDEO

Subject: I WANT YOU TO RELAX TOMORROW

Subject: BUT I WANT YOU TO THINK ABOUT THIS

Subject: DID YOU KNOW YOUR DAUGHTER WAS SLUTTY LIKE YOU?

I read through the e-mail subjects until I got to the last one. "What the fuck?" I said as I sat up in my bed. I clicked the last e-mail and inside was a link to an Instagram account. I had no idea what was going on since I had Emma on my Instagram and this most definitely wasn't her name on there. I clicked the link hesitantly now thinking that maybe this really was the virus I always thought it was, but instead it took my to an instagram page with pictures, pictures of Emma, but not the Emma I knew.

My mind raced as I scrolled down the almost endless list of pictures in Emma's secret instagram account. Each picture showed Emma, my perfect daughter in seductive poses, revealing clothing, it was not what I was expecting to see tonight. I opened a few of the pictures, the first one had her in a super tight and short black dress, nothing on her legs, cleavage on show. The next one had her in tight and short black spandex shorts, but her legs were spread wide open. I kept scrolling and clicking. There was one with her wearing thigh high socks and a short skirt, she was bent over showing her panties. Another had her giving the peace sign sticking her tongue out and her eyes rolled back. Picture after picture showed my daughter in slutty poses. And maybe worse of all were the comments, strangers leaving lewd words on her pictures, "so fucking hot!", "you're such a slut!", "omg I want to fuck you so badly!", comment after comment was about her body, her sluttiness, how hot she was. As I read through them I started to see her replies to some of them, thanking the random strangers for their comments, for their comments of calling her a slut! My mind felt like it was melting, what the fuck was going on?

I checked my e-mail again and saw a new message.

Subject: ENJOY YOUR DAUGHTERS PICTURES

And then another popped up.

Subject: DON'T STOP HER OR I WILL RELEASE

And a third.

Subject: RELAX AND LET YOUR MIND WANDER YOU KNOW YOU WANT TOO

What a fucking pervert I thought as I read the subject lines. Who does this asshole think he is? I slammed my laptop shut and threw it on the floor and tried falling asleep seething again. My mind racing through the week, what I had done, what I had been told to do, and now the pictures of my apparently slutty daughter. Fuck, what the fuck was I going to do?

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
spankfunforspankfunforalmost 3 years ago

Love Mother and Daughter Getting Closer!

heavyandhornyheavyandhornyover 4 years agoAuthor
Thanks for the comments!

Thanks everyone for commenting. They have given me some thoughts on how to continue. I'm trying to write smaller chapters which are easier to edit and hopefully I can get them out sooner. Chapter 3 has just been submitted. It's a little bit of a slow burn but I assure you there will be more action coming soon. Thanks!

AnonymousAnonymousover 4 years ago
Plz be the son..

I hope it's her son Sam who is the blackmailer....

AnonymousAnonymousover 4 years ago
Suspense upped by a few notches

Who sends these mails? Someone we know already? Son?

Will she get an instagram account of her own?

Where is the series of tasks leading to? Just more degrading / humiliating tasks? Or a switch to RL submission?

Hope some answers come soon together with next chapters ...

AnonymousAnonymousover 4 years ago
My guess of who is the tormentor.

It could be someone in the tech office having access to all the videos of classrooms. Or it could be a classmate seeking revenge against daughter Emma for some reason of her choosing.

If we assume a boy nerd chasing Emma it will be so so. But if we make story spicy, we would add a young strong black woman who has Emma in her clutches for racism and makes her do suggestive posting on instagram to disabuse Emma of becoming a strong confident White woman but a submissive to her needs. Goal may be to eventually turn her into a slut for BBC. For her mother Madison, she was able to hack into the schools video system where she discovered tittilating evidence against her to send blackmailing email demands on what she should wear to school. Perhaps she doesn't like the vibes she is getting from Madison on her schoolwork and perceives it to be racial like Emma's.

Keeping both mother and daughter dancing on pins and needles as mother gets daily email tormenting on required dress issues and daughter on instagram suggestive postings while continuing wearing her conservative dress with a couple of buttons loose on sleeveless blouse vice wearing bra only. Goal may be to get mother to go out dating but only on mistress's stronger terms in choosing whom she will go on date with. Eventually change the direction of their lives much to their shock..

Show More
Share this Story

Similar Stories

Jasmine's in Trouble Ch. 01 A successful and sexy blonde is blackmailed into slavery.in NonConsent/Reluctance
Awakening: 7 Slutty Blackmail Tasks MILF's sexual awakening by being forced to do 7 slutty tasks.in Illustrated
The Taming of a MILF Ch. 01 Middle-aged wife pays the price for being a tease.in NonConsent/Reluctance
Playing "The Game" Ch. 01 Olivia decides to play a new game.in NonConsent/Reluctance
Black Screen Pt. 01 Cheating student loses control of her webcam and her life.in NonConsent/Reluctance
More Stories