Madison's Changing Life Pt. 05

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Madison starts to like it and opens up.
5.6k words
4.51
46.6k
27

Part 5 of the 18 part series

Updated 06/09/2023
Created 10/09/2019
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I woke up the next morning, Monday, with my mind in high gear. After the weekend of teasing and the webcam show the night before I was feeling horny and that wasn't good for my war with the pervert. I thought back to the night before and how much fun I had showing off. It made my pussy a little wet just thinking about it.

As I got out of bed I remembered the e-mails as well, I had to dress sexy today, but I had no direction. What do they think is sexy? I had to balance what they wanted and what would be appropriate for school. My hands started to dig through my closet and drawers looking for something that would work. What I settled on wasn't something I really liked, and not something I had worn in years, really it was more office attire then school attire, but it was what I had, and I thought it would work.

After my shower and make up I started getting dressed. I slipped on a pair of very small thong panties as I knew my skirt would show anything else. My hands grabbed the tight black skirt and I started to pull it up my body, up over my ass and on to my waist. I reached around and zipped it up from behind. The skirt was just above my knees, and went up to my waist, clinching everything in, but also showing every curve. It looked good on me I thought, but definitely not something I would wear usually. I then picked a white bra and white button up shirt which I did up except for the very top button and tucked into my skirt. I didn't wear any pantyhose, so my bare feet slipped into a pair of sensible black heels. I spun around looking at myself in the mirror. I looked like a different person, so professional, so put together. I looked like someone who actually cared what other people thought when they looked at me. I wasn't sure if I liked that or not.

I headed downstairs to make breakfast as usual and yelled up for Sam and Emma to come down. Eventually I heard footsteps on the stairs and they walked into the kitchen, I could feel Emma's eyes look me up and down as she walked in.

"Wow mom," Emma said, "lookin' good!" there was a definitely chuckle hidden in there.

"Uh, thanks?" I responded, still a little unsure on how to handle this.

"All the boys in school are going to start having a crush on you," Emma laughed as she ate her breakfast.

"I hope not!" I said in shock. The last thing I needed was teenage boys looking at me like a sex object. I already had one pervert using me.

Emma just chuckled, she knew she was egging me on and apparently enjoyed it.

"SAM!" I yelled upstairs gain, "Do you know where your brother is?" I asked Emma next.

"Nope, I didn't hear him this morning," she said while eating and checking her phone.

"Fuck," I said probably too loudly, but it didn't seem like Emma heard. I realized then that swearing was becoming a little too easy for me lately.

I left the kitchen and walked upstairs and knocked gently on Sam's door but heard nothing in response. My hand turned the knob and I walked in to see him still sleeping under his blankets.

"Sam, you have to get up and get ready," I said while gently rocking him. He started to stir.

"I still don't feel welll," he mumbled out. I sat on the edge of his bed and looked at him, and then at the time.

"Hmmmm, OK, well why don't you stay home today, I'll tell the school when I get there," I wasn't really sure how sick he was, but I was running late and he's old enough to make his own decisions, so it was what it was. "I'll see you later, hopefully you'll be feeling better," I said softly as I left his room and closed the door before heading back down to the kitchen.

"Ready to go?" I asked Emma as I walked in.

"Where's Sam?"

"He's not feeling well so he's staying home today."

"Ya, sure he is," Emma said with a smirk. I didn't disagree with her, but it was what it was, we were already going to be late. We walked out and went to school, just the two of us. As we got there and I parked Emma has one last thing to say before we parted ways, "Hopefully the boys don't stare at you too much today!". I could feel the blushing run into my face but Emma was already gone, meeting up with her friends before walking into the school.

As I stepped out of the car myself and started to walk into the school towards my class I could feel the eyes peering at me. I didn't really understand it, I wasn't showing a lot of skin, my skirt was almost down to my knees, my shirt covered all of my arms, I wasn't even showing any cleavage, but for some reason people seemed to notice me. I knew my clothing was different then what I normally would wear, my skirt was tight and I hardly ever wore shirts like this, but still, it was just clothing. I pushed on and continued to my classroom through all the peering eyes. I could hear people whispering as I walked by, looking at my ass while I passed. I would be lying if I said I didn't start to like the attention. Last night was people I couldn't see, but now these were people who saw me and I could look at in the eye, for some reason it made it even hotter, even dirtier. I could feel my pussy getting wet.

My first class started and I tried to compose myself. I could tell the students in front of me where talking about me, about what I was wearing. I just tried to focus on the work in front of me, on doing my job, on teaching. Every time I got up from my desk I could see student's eyes raise from their books and look at me. As I walked through the aisles as they read I felt their eyes follow me. For some reason today students seemed to have a lot more questions as I walked by, forcing me to bend over and help them, giving a better view to the students around them. One time I dropped a piece of chalk on the floor and had to bend over to pick it up, I felt like laser beams were focused on my ass from the students eyes.

Each class was the same, and each class turned me on more. I loved the feeling of people looking at me, at wanting to see me. I never realized this about myself before. Maybe it was because I've been alone for so long, I haven't had the attention I needed, or maybe it was just another one of my kinks, but whatever the reason was, I liked it.

As my third class finally came to an end I was so ready to get off, to fuck myself and cum right here in the class room. As the last student walked out before lunch I was about to close the door when my brain shifted into mother mode. Sam. He was at home sick and I knew the right thing to do was to go and check on him. My eyes looked up at the clock and I had just over one hour until my next class. I went through the timing in my head, I could go home to check on Sam, rush back, get off as I had to do, and then be ready for my next class all in an hour; if I hurried.

I shoved my papers in my desk, grabbed my purse and walked quickly out to the parking lot. I could feel my skirt slip slowly up my legs as I walked, not by a lot, but just the feeling of the extra exposure for some reason turned me on even more. It was starting to feel like I was discovering this hidden part of me. I knew about my love of getting stretched out, but this was something new, something I hadn't tried before, being exposed a little, having people look at me, maybe even want me, it was hot and turning me on.

I got to my car and quickly drove home, I wasn't really thinking of much until except for being quick and efficient. As I opened the door and walked in I almost immediately heard some weird sounds, something like from a TV or computer. It sounds like Sam was awake and watching something, it sounded like Sam wasn't nearly as sick as he let on this morning. Annoyed I walked up the stairs towards his room. The closer I got, the more I started to hone in on what the sounds were, not just regular TV sounds, there was moaning and swearing, I was almost certain he was watching porn. So he said he was sick and then stayed home to jerk off? I was pissed off at this point. Here I was rushing home to check on him and this is what he is doing?

In retrospect I should I have known not to do this, but I did it anyway, I walked up to his door and opened it without knocking. What I saw inside shocked me beyond belief, and I know it shocked him to see me in his doorway.

As I walked in my eyes adjusted to the darkness in his room, the blinds drawn shut, the only light coming from his computer screen. The image he was staring at was of a blonde teenage looking girl getting double penetrated by two giant black cocks. If I wasn't in such shock I would have found the scene to be hot beyond belief, but I couldn't concentrate on that, all I could see was my son, Sam, and what he was doing.

My eyes focused on him as his head turned towards me, a look of absolute horror on his face. He was kneeling on his bed, no shirt on, his hard cock in his hand. But that wasn't what really shocked me. What really made me head spin was what my son was wearing. A pair of red thong panties, my panties. He had them pulled up around his hips, but had the front pulled down so his hard cock could be free for him to stroke. The scene made my head spin. What the fuck was happening?

I stumbled backwards as I tried to leave the room. "I'm sorry...," I stuttered as I left, not knowing what to say. I finally exited the room and ran downstairs leaving his door open. I heard Sam yell, "MOM!" from behind me. I made my way to the kitchen and collapsed in a chair, my head fell into my hands, my brain racing. "What the fuck," I said to myself. I just caught my son masturbating to porn wearing a pair of my panties. Why was this happening? Why was this happening to me? First my daughter with the instagram account, and now my son liked to masutrbate in his mother's panties? It seemed like my world was falling down around me again.

I heard footsteps in front of me, it had to be Sam but I had trouble raising my head and looking at him.

"Mom... I uh... I'm sorry," Sam was struggling to get words out, I kept my head in my hands. "I just, uh, ya..." he continued, obviously not knowing what to say. Neither of us did.

After a minute I finally built up the courage to look at him. My head slowly raised and my eyes moved up his body. He had thrown on a pair of grey sweat pants, the ones that were too tight, he had no shirt on, his skinny body on show. He probably didn't realize it but I could see the sides of the red panties above his pants on either side and it was obvious his cock hadn't full receded yet as I could clearly see the outline. I tried to collect my thoughts as I looked him in the eyes.

"Uh... sorry Sam... I was just shocked," I said, what else was I supposed to say? "It just wasn't what I was expecting."

There was an awkward moment of nothingness, and then finally he spoke.

"I won't do it again..." he mumbled. I could tell he was embarrassed and ashamed at what had happened. Maybe not with what he was doing, but getting caught for sure.

What was the right thing for a mother to say? Should I tell him good and make him feel bad for what he was doing? Masturbating wasn't evil, I was just shocked. I masturbate, and most people do, everyone has their kinks too, me especially. I worked through the responses in my head, and what I finally said was maybe too much the other direction, too positive, but I'd rather be positive and supporting then negative with my kids.

"No, honey, it's OK... you should do what you want, what feels good," I paused before continuing, "we all do what feels good to us, I want you to feel comfortable to do whatever you want, OK? If you aren't sure about something, just talk to me, I promise I'll be open minded, OK?" I said all of this in a calm and measured tone, trying to reassure him. I waited for his response.

"OK... thanks mom... I'm going to go back upstairs," he said while turning around and walking away. I watched as he went, he ass kind of swaying as he walked. I could have scolded him and told him to go to school for the afternoon, but it was obvious he was struggling right now, I didn't want to force him to do anything, at least today.

I got up from the chair and headed back out the door. This lunch period was not going as planned. Beyond the whole Sam ordeal, now I was behind schedule with only 20 minutes until my next class started. I raced the car and drove as fast as I could go back to the school. I almost ran through the yard and school and into my classroom, slamming the door behind me before I locked and closed the blinds. Twelve minutes left. "Fuck!" I said as I ran over to my desk. My mind was racing, I was supposed to do something different than usual. "OK, what do I do?" I said to myself in a panic.

I pushed the stuff on my desk to the side, moving some of it to the floor beside my desk. I kicked off my shoes and slide on to my desk. I leaned back making sure my pussy was pointing towards the door so the pervert could see what I was doing. My legs bent and I pulled the skirt up under my ass. Ten minutes left. I pushed my panties to the side exposing my cunt to the air. My other hand unbuttoned some of my shirt exposing my bra which I pushed down down as the same hand pinched one of my nipples.

My other hand started to rub my clit as I could feel my juices running down my thighs. My mind started to wander. Eight minutes. I shoved three fingers into my cunt right away and started to move them in and out roughly. My hole didn't need to be warmed up, it was always gaping and ready to go. My other hand roughly pulled on my other nipple. I wasn't even thinking about the blackmail, I just needed to get off. As much as I tried not too my mind kept running to one place, back to lunch, back to seeing Sam in my panties and his cock. The more I thought about it the more I thought about his cock, it looked huge now that I thought about it, maybe eight or nine inches I think. Maybe I was exaggerating, I don't know, but it looked amazing, rock hard, his balls cupped by the red panties. Oh fuck I was so horny. I could hear myself moaning outloud as I continued to fuck myself. Four fingers were now jamming their self into my sopping hole. 4 minutes left.

I knew that some students might show up early, I knew I was running out of time, I had to get off right away, right now. I tucked my thumb into my waiting cunt and pushed, my hand easily slipping into my giant fuck hole. My hand balled up into a fist as I reached over my body and I started to roughly fuck my fist in and out of my body. My moaning was loud now, I was getting worried that someone could hear my. My other other came to my mouth to muffle my sounds. The fist in my cunt started to exit and enter harder and harder, all the way out, I was punching my pussy like I haven't done in a while, it was so hot, being on my desk, in my classroom, punch fucking myself thinking about my son's hard cock. Everything was so dirty, so nasty, I just couldn't control myself.

I heard a knock, my time was up, "FUCK," I said outloud, there was no way I could stop myself. I knew I only needed a few seconds more, I kept fucking myself harder and harder until I finally cummed. I could feel my cum juices pour out of my pussy and on to my desk. My head fell back, my body went limp, my breathing heavy and my heart pumping hard. I heard another knock, but my body was too limp to do anything about right now. I had to calm myself, to get myself back to an even keel. The minutes seemed to flow by, my brain not properly functioning. Finally I heard another knock, harder this time. I had to do something or someone would get suspicious. I pushed myself up off the desk and got to my feet, my legs were wobbly.

The first thing I did, and I don't know why I did this was I licked my hand that had been in my pussy, I ran my tongue up and down it tasting myself. I could feel myself blush as I did, but it just felt natural, like the thing I should do, it just happened. After a few seconds though my mind started coming back to life and I remembered where I was. My hands pulled my skirt back into place and I wiped my juices off the desk before putting things back into place. I pulled my bra back into place almost forgetting to do it. I straightened my hair and walked over to the door opening it.

"Sorry everyone!" I said as people starting walking in, "I was just finishing up a phone call."

Luckily I was only about 5 minutes delayed, anything longer and people may have gone to ask questions. As the students kept flowing in and sitting down I started to realize their eyes kept looking at me in a weird way, I was trying to think of what it could be, did I have something on my face? Was I still sweating? Did I smell bad? It was only after everyone was in the room and I started walking back to my desk that I saw what was going on. In my reflection in the window I saw it, my chest, I had forgotten to button up my shirt, my bra was on display, not fully thankfully, but everyone could see it nonetheless. The problem was what could I do about it now? If I did up the buttons now it would draw more attention to the situation. "Fuck" I said in my head. I continued class as usual with my bra out in the open, trying to conceal it as much as possible, but also realizing more and more how much I liked showing off like this. My brain worked overtime for the rest of the class and I was realizing that the blackmailing pervert was somehow bringing out my dirty self more and more. As much as I hated them, I was actually starting to like what was happening. But there was no way I would ever admit that to them. Fucker.

Finally my fourth period class ended and the students left giving me the time I needed to button up the rest of my shirt. I knew that there was no way that news of this wouldn't get out and spread around the school. Almost every student would know about it by the end of the day that was for sure. My face blushed as I realized Emma and Sam would be two of those students, hearing the rumours about how their mom had her shirt undone in class. I shook my head thinking about how my life just kept slowly unravelling around me.

My next class funneled into my class and took their seats. I could hear the whispering again, the stares, the comments. It was obvious that the news had already spread to this class. I tried to ignore it and just focus on teaching but it was hard, I just couldn't wait for the class to end so I could get out of here.

The minutes seemed to tick by extremely slowly, dragging the last class out as long as possible. At one point it seemed like time was actually going backwards. I waited and tried to fill time until I was eventually given reprieve and the final bell rang. The students filed out of the class, and then I grabbed my things and walked out to my car as usual. I tried to ignore the stares, but they just kept coming and forcing their way into my soul. I got to my car and sat down inside, waiting for Emma, and trying to hide myself from anymore peering eyes.

I saw Emma coming from ahead of me and I looked up at her with a smile. She opened the passenger door and sat down, not looking at me or saying anything.

"Hey honey," I said as I backed out of our spot and started driving. All I got in response was silence.

Shit. I was almost certain I knew what was going on. She had heard the rumours about her mother having her shirt undone in class. My eyes stayed straight on the road while my mind tried to figure out what to say, and how to fix this issue. I also thought about how none of this would be happening if it wasn't for that asshole with the e-mails.

"Hey, honey... I think we should talk," I started while slowly driving home, "I'm assuming you heard about my... wardrobe malfunction today... uh, it was just an accident," it really was an accident, even though it hadn't started that way. I didn't mean to have it undone the whole time.

"Was it an accident though mom? Really?" thankfully Emma started talking, but kept looking ahead, "I mean yesterday you're wearing slutty clothes around the house, and now you're showing your bra in class, what the fuck is wrong with you?"

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