Chapter 2

The rest of the summer went by fast. Mom and dad had a few more parties without any incidents like Mr. Wards retirement party. School was starting up next week. I still hang out with the guys. They haven’t been back to my house since the party.

I was bored to death. The only thing that kept coming to mind was those videos. I kept rethinking what Dave wanted to do, blackmail the five MILFs. I really didn’t want to blackmail my own mom; therefore, I couldn’t blackmail the other four MILF.

What I eventually came up with maybe I could just mess with their heads. Being a bored male teenager puts a lot of fantasies into your head. I had to come up with a plan. I thought about it almost day and night. Like Mr. Ward said don’t want to ruin their lives. Which I didn’t, but mess with their heads is another thing. It took me few weeks to work out a plan.

The first thing I did was to buy a burner phone. I made up a name and address and an email address. I know they can still be tracked but I was trying to make it hard for whoever did, if they did. Next, I loaded a few of the videos onto the phone. I made sure I could just send a picture and not the whole video. Once I had all of that done, I still didn’t know if I wanted to go through with it.

My next move was a little harder. I had to get a hold of mom’s phone so I could get all of the other women’s phone numbers. I thought it would be harder getting Mrs. Lee’s number, but it wasn’t. She had become friends with my mom and the other three teachers.

School started back up before I had a good plan put together. Hell, I never did get a good plan but I went ahead anyway. I was in study hall not long after school started. The teacher we had didn’t mind if we use our phone in study hall as long as we stayed quiet so other could study.

I didn’t have any homework and was again bored to death. My thoughts drifted to the MILFs and the videos. I wasn’t really thinking when I started a group text. “You five need to know. This summer I was out and came across a yard sale. To my surprise it was Mr. Ward’s estate having a yard sale. I found a box of flash drives and DVD’s. I bought all of them. Was I ever surprised at what I found? Well to make a long story short. Here is a picture of you five. The question is what, will you do to keep this from getting out. We all know there is no doubt the four of you will be fired and one husband in deep trouble if this became public. By the way there are several other videos to go along with a bunch of still shots.” I downloaded one picture of the five of them in their birthday suits with a smile on their faces. None of us guys were in the picture. I was smiling when I hit send.

Being they didn’t know who the sender was I really didn’t think I would get a reply. The next day in study hall I turned my burner phone on and had five replies to my text. “Who is this? What do you want? Where did you get this picture? You want money?” Were the four main replies. I all most laughed out loud. Good thing I didn’t. The head messing has started I thought. I replied back: “No money at this time. I already told you where I got the picture from. For being teachers, you don’t comprehend well, do you? Now answer my question what will you do to make sure this doesn’t get out?”

I left my burner phone in my locker at school that night. Which turnout to be a good thing. I normally get home before mom but today she was there waiting on me.

Mom: “Give me your phone!” I didn’t say anything, handing it to her. She knew who ever sent the text wasn’t from my phone because of the number. She went through every file on my phone. She looks at me when she didn’t find what she was looking for. “Do you have another phone?”

Me: “No, why would I?” She just gave me a dirty look as she walked off.

Next day in study hall I had another reply. They must have gotten together: “We talked about your question. We’re guessing you already know this, but we want to make sure. We are all married and four of us are teachers. The other is a wife of a teacher. If you want money, we will try to meet your demand. We are willing to do anything you want as long as it doesn’t ruin are livelihood.”

Since mom had already checked my phone, I started bringing my burner phone home so I could keep it charged. I still only turn it on at school during study hall to check it.

I know my mom and the other three teachers wore way too many khaki slacks with baggy tops. Mrs. Lee I’m not sure what she wore since I really don’t see her much. I know mom had a few nice skirts and dresses. I’ve seen her only wearing them to school if there was something special going on. Same with the other three teachers. The first task was to get them to dress up more for school and get them to send me a nude selfie.”

I text them back: “You really didn’t answer the question. Again, I don’t want money right now. I want you to send me full nude pictures of yourselves to me. I want to see your faces, tits and pussies in one selfie. Tomorrow, You four teachers will wear a skirt, and a white tight blouse with heels. Don’t send the pictures as a group text. For you Mrs. Lee, you will wear a skirt, tight white blouse with heels. You will come to school to eat lunch with your husband. You’ll eat in the school cafeteria. Don’t test me, make it happen.”

That evening mom gave me a nasty look. Me: “What did I do?”

Mom: “Nothing, I’m just not in a good mood.”

Next day mom had on a nice skirt and a white blouse. It wasn’t tight. She didn’t have heels on. She is testing her tormentor. This might be fun. The four MILFs half dress the way I told them. Mrs. Lee did show up for lunch with her husband and they both ate in the cafeteria. Well, it’s a start.

Finally, I was in study hall. I took my phone out I had five texts. All five of them did send me my picture. I enjoyed looking at them smiling as my mind began to work on what I would demand next. I sent a text to each of them. The same text just to each induvial. “Thanks for the picture. Now shave the hair off your pussy and send another one. However, I am disappointed with each of you. Where were the heels I demanded you to wear? Your blouse was too loose. I know you don’t think I’ll send the picture or maybe it’s not graphic enough for you. If you don’t do what I tell you one more time, I think a lot of people are going to see a lot more of you, if you get my drift. Tomorrow, you will wear a skirt and a tight yellow blouse. If you don’t have one go shopping. Don’t fuck with me bitch.” I download another picture. A different one for each. It was a picture of them nude with one of us, I didn’t send a picture of me with any of them.

Wow I couldn’t believe I just called my mom a bitch a long with the other four MILFs. We’ll see what happens next. I was home before mom. When she got home, she looks like she was in a hurry.

Mom: “We need to talk when I get home young man, but right now I need to go shopping.” Out the door she went.

By the time mom finally got home dad had fixed dinner. We ate and after dinner mom went up to her room. She didn’t come down for a while. I was already in my room getting ready for bed, when she came into my room shutting the door.

Mom: “Now tell me the truth. I saw a picture of me and Dave. I was nude and Dave was clothed. Now tell me again how long did you guys stayed at the party.”

Me: “Busted. We were getting ready to head back to Tim’s, when you ladies all took off your bathing suits. Being young horny teenagers, we stayed. Mr. Ward took some pictures. I thought when he died, they would have just disappeared. I didn’t tell you about that because you were so drunk, I didn’t think you would have remembered. I was just trying to be a gentleman. How did you get a copy of the picture?”

Mom: “Someone is tormenting me and the other four ladies. How many pictures and with whom?”

Me: “Don’t kill me. You and the other ladies posed with all of us guys. Yes, mom you posed with me also. It gets worse. You and the ladies, no better way to say this, you all had sex with us. No mom you didn’t have sex with me.”

Mom just stared at me for a moment: “Shit, who ever got those videos knows everything. Okay I understand why you didn’t tell me, but you should have.”

She left the room. I knew she would let the other four MILF know. I think I have them in my pocket now. I need to see what I can make them do without them finding out I’m their tormentor.

The next day mom was wearing a nice skirt and a nice yellow blouse. It was tighter than the white blouse she had on yesterday. Now I need to decide if it’s tight enough or get into her shit again. I couldn’t wait until I got to my burner to see if they shaved their pussies.

Back in study hall I again took out my phone. All five MILF text me with a new selfie. Their pussies were all shaved. I need to give them another task. All of my texts will be to each individual MILF from now on, unless it needs to be a group text. I know they will compare with each other. My text: “Glad to see you did as you were told. Keeping me happy is the only way to keep these picture/videos from getting out. Your next task: You will make a five-minute video of you bouncing your boobs for me. Examples: Hand under tits bouncing them, jumping up and down, swaying them around. I don’t really care how you bounce them, but you better have them bouncing for five minutes. I also told them how to dress for the next day. One question: have you told anyone about what you’re doing to keep these pictures from going public? Don’t disappoint me slut.” Wow in the last two days I’ve called my mom bitch and now a slut.

Mom didn’t get home until late. She had to go shopping again. After dinner mom came up to me: “Jason, I need to know how to work my video on my phone. without me holding it.”

Me: “I don’t believe you don’t know how to do that. Okay, but why?”

Mom: “I told you about my tormentor, well I need to send him a video.”

Me: “Do you want me to just video you?”

Mom: “Oh no! I don’t need you or your dad any more involved than you already are.”

I just gave her a look. I took her phone showing her how to do a video without holding onto the phone. After she headed to her room I got to thinking. Has she told dad what’s going on. I’m sure she did. I guess I’ll have at least one good video tomorrow.

Next day when I check my phone, I had four videos. Three of them stated they haven’t told anyone. My mom said she only told her son about me, but not the whole story. Mrs. Lee sent a text: “I’m not doing this. I have had enough.” I knew I would have to come up with some kind of punishment for Mrs. Lee. I thought about it as I watch the video my mom sent. Before I started it, I turn on my timer on the phone I want to make sure it was five minutes long.

She was in her bedroom with her hands under her boobs moving them up and down and all around. As she bounced her boobs she was also playing with her nipples. She was smiling. As the video played, she seems to get more into it. She was actually having fun by the time it ended. It was a few seconds over. All of the women’s videos were about the same. They must have talked about it before hand.

It didn’t take me too long to decide what to do with Mrs. Lee. I took one of her pictures and blocked out her face. You could tell it was her if you knew her. I found an adult web page where you can post amateurs pictures. The pictures would stay posted for ten days before disappearing. I post the picture. I sent a group text: “This is what happens if you disobey. Next time Mrs. Lee’s face will be shown.” I added the link to the web page and hit send.

Next, I sent each one another text with their next task. “Ladies, all of you except one completed your task. Your next task is to video yourself nude masturbating. This one need to be at least ten minutes long. Plus does anyone else know about me, your tormentor? I also gave them instructions on how to dress.” I hit send. Again, mom had to go shopping after school.

Next day Mrs. Lees text: “I didn’t think you would post any of the pictures. Please take it down. I’m sorry, I’ll compete all task from now. Please I beg you to take down those pictures. I have not told anyone about you.” Still no video.

My text back to her: “Listen up bitch, still no video of you bouncing your boobs. Your task last night was a video of you masturbating. You’re not begging you’re asking me to post another picture this time with your face showing. Now bitch you’re at home. It’s just you and the kids. Hubby is at work teaching. Get off your lazy slut ass, get me those videos by the end of the day, plus your next task which is: A video of you in the shower. Again, you have until 5 P.M. Or everyone will see a picture of you nude with your face. Stop fucking with me bitch!!”

I got a text right back from Mrs. Lee: “I’m sorry I’m getting right on those videos now. Please I’ll do anything you want just don’t post anymore pictures.” Mrs. Lee is now in line, I hope.

My next text to Mrs. Lee: “You have until 5 P.M. You need to be punished. This Saturday have your husband babysit. Go over to Sandy Moore’s house. The other four sluts will be there. They will punish you. They will video it and send it to me. Now get off your lazy ass and make those videos.”

My next text was a group text to the MILF with their next task which was a video of them in shower. I waited a minute before my next text to the group: “Mrs. Lee still not doing as told. This Saturday you all will go to Sandy’s Moore’s home. Be there my 10 A.M. The five of you will go down into the basement. Where all of you will spank Mrs. Lee. Use one of the ping pong paddles. You each will give her 20 very hard smacks on her bare ass. Don’t be easy on her, or I will post pictures of all of you on that adult site with your faces showing. You know by now I will.”

I got a group text back from my mom: “I had something planned and won’t be able to do this.”

My I replied in the group text: “Bitch. I don’t care what you have planned. I just told you what you’re doing. You five bitches better get on board, or I’ll ruin your lives. Know this you five will do anything and everything I tell you to do. If you haven’t realized, you five belong to me You will obey my orders no matter what it is!” I didn’t get any more text from the women.

Later in the day I receive a text from Mrs. Bishop: “I’ve had to go out and buy new clothes every night. I sure the other ladies also had to. Please, let us go back to wearing clothes we already own.”

I sent her a reply: “The clothes I’m telling you to wear are clothes you should already own. If you don’t, well guess what I’m doing you a favor. I’m not your husband stop the bitching.” I’m sure she informed all of the other MILF what I told her.

I notice the other four MILFs did send a picture. I have sometime left in study hall, so I watch my mom’s video. As the video came into view mom was nude laying on her bed. I was smiling as I watch in delight. She looks gorgeous laying there. Her breast bounce ever so slightly as she rocks her hips. Her hand was concealed by her thigh right now. It didn’t take much imagination where it was as she rock rhythmically.

Here I was in study hall getting aroused as I watch my mom. She had sound on and I could hear her moaning as she started getting more intense playing with her pussy. Her free hand works its way to one of her nipples, she begins to pinch and pull on it in rhythm with her other hand which she continues to thrust in and out of her sweet wet pussy. Mom raised her hips as she was getting closer to getting herself off. Even with one hand playing with her one tit, the other tit would jiggle. I can now see she had three fingers rubbing around her pussy. Every once in a while, pushing them deep inside of her.

Mom was going strong as she moans: “Oh god YESSSSSS!!” As she started having an orgasm. When she finishes, she looks into the camera: “Hope you enjoy the show.” As she now had both hands playing with her breasts. She squeezed them roughly as she smiles into the camera. She was satisfied with getting herself off. She rose off of the bed turning the camera off.

As I turn off my phone, I notice I was the only one left in the room. I got up I was going to be late for my next class. Oh well shit happens.

I stop by Tim’s on the way home just to hang for a while. When I got home, mom was already taking a shower. I’m guess she is filming it. The weekend was coming up.

On Friday I text them: “Don’t forget to be at Sandy’s house by 10 A.M.”

Saturday morning, I’m eating breakfast with dad, when mom walked in. She was in jeans and a nice top. Damn I forgot to give instruction on how to dress for the weekend. But then how would I enforce that since they didn’t know I was their tormentor. I believe they are trying to figure it out. I’ll have to figure out how to let them know I’m watching them even while they are at home.

Dad: “You haven’t left yet? I thought you had to be at your sisters early today.”

Mom: “Something came up. Hannah, Irene, Emily and Betty agreed to coming over this morning. I call Pam letting her know I won’t be there until lunch time.”

Dad: “What came up?”

Mom: “Just some stuff us girls need to talk about. You still going to the golf course?”

Dad: “Yep, as soon as I’m done here.”

She got herself some toast and coffee. Looking at me: “What are you doing today?”

Me: “Going over to Tim’s.”

Mom: “I haven’t seen him for a while.” I didn’t say anything. After I was done eating, I went in the living room turning on the T.V

Dad headed out to the golf course, about 9:45 the MILFs started showing up. They all were wearing jeans and nice tops. Mrs. King: “How are you doing Jason?”

Me: “Just fine.”

Mrs. Lewis: “What are your plans for this weekend?”

Me: “I’m headed over to Tim’s in a bit. Other than that, not much.”

Mom came into the room: “Okay ladies let’s go to the basement.” All five of them walk down the stairs. When I heard the basement door close, I got up and went over to the basement door to see if I could hear anything. Everything was muffled. Then I heard Mrs. Lee yell: “Ouch!! Not so hard.”

Mrs. Bishop; loudly: “You almost got us all fired. I don’t know who this asshole is, but he means business. We’re filming this like he said and you’re going to get 20 very hard whacks from each of us.”

Mrs. King: “I have no problem with spanking you. What were you thinking. Just do what he wants. At least he isn’t asking for money or sex.”

Mom: “I had something plan but now I have to be here spanking you. I don’t want to be fired. I for one don’t need any of those pictures or videos getting out. Don’t worry you’ll receive 20 hard whacks from me.”

Mrs. Lee: “Sorry, guess I deserve this.” They stop talking and the spanking continues. I could hear Mrs. Lee crying now. I decided to head over to Tim’s. I’ll watch the video later.

Sunday morning, I was in my room watching Mrs. Lee getting her spanking. The other four MILFs did not take it easy on her. I sent them a text letting each know what I wanted them to wear: “First I want to say good job on spanking Mrs. Lee. Hope we don’t have to spank anyone again. Tomorrow, you all will wear a dress that shows a lot of cleavage. Stockings and high heels. Make sure you have a nice necklace on.” I told Mrs. Lee to send me a few nude photos since she will be home with the kids. Mrs. Lee is getting over big time. I need to come up with something for her to be humiliated.

About noon mom and dad were getting ready to go out, Me: “Where are you two going. Maybe I like to go too.”

Dad gave me a weird look: “Really, a teenage boy wanting to hang out with his mom and dad.”

Mom laughs: “We’re going shopping. I need a new dress.”

Me: “In that case I think I’ll stay home.” Dad just laughs as they left.

Mom and the other three MILF teachers looked great in their dresses, mom’s and Mrs. Lewis’s dresses were particularly nice. It looked like their boobs were about to pop out at any moment.

I really don’t know what was going on with me. I started this just to fuck with their heads a bit. You know, see if they would do as I said. I really didn’t want to ruin them or cause them to lose their jobs. But with each task I give them, I feel this rush when I get the video or pictures. The feeling of power as I push them further and deeper under my control. Plus, I’m noticing mom seems to be actually enjoying obeying me. Other than Mrs. Lee the others also seem to be getting into it. Just not as much as mom is.