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Four Teachers are Blackmailed Ch. 01

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Four MILF teachers end up blackmailed.
14.3k words
4.5
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Part 1 of the 2 part series

Updated 06/09/2023
Created 01/24/2020
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Thecsm
Thecsm
1,517 Followers

Thanks to Smoothed for all of his hard work in editing this story. Also want to give Agedrooster thanks for helping in the development of this story.

*****

Everyone in this story is over the age of 18.

It is the first day of summer vacation between our junior year and senior year of High School. Tim and Dave are over at my house hoping to catch a glimpse of my hot mom and her three friends. We are sitting around and I am watching them play the X-box. While we play, we talk trash mainly about the jobs we got for summer. Tim and I had already turned 18 and Dave will be 19 by the end of the month.

My mom walks into the living room. Dave looked up.

"Hey Mrs. May how are you today?" he asked.

"I'm doing fine and you?"

"I'm doing great now that I have gotten to see you." Dave raised his eyebrows playfully.

My mom knows that Dave has a crush on her. She just smiles at Dave, then turns to me.

"Hey Mike, Jane, Sue and Kay will be by later. You don't mind, do you?"

Before I could answer Tim jumps in, "We don't mind at all."

"Guess that answers your question mom. Do you want us to move to the basement?" I ask, as she smiles at us.

"No you can stay where you are," she says, walking by and leaving us in the living room.

Dave and Tim are my best friends; we've have been friends as far back as I can remember. If you see one of us, the other two aren't too far away. Dave is a lot taller than Tim and me, at around six feet four inches, with me being six foot even and Tim at five feet and ten inches. All three of us played on the football team.

We're not muscle-beach muscular but we are very fit. I have heard girls from school talk about how attractive we are. We normally don't have much trouble getting young ladies to date us, especially with Dave having picked up a reputation with the ladies of having a large package. However lately we seem to be going through a drought with the women.

About an hour later there is a knock on the door. Dave jumps up and answers it.

"Well hello Mrs. Hill, Mrs. Powers, and Mrs. Peterson." Before they can say anything Dave yells out, "Mrs. May your friends are here!" With a glance back to the ladies, he invites them inside.

As they enter the house, mom joins us in the living room. "Hey girls," she calls out and escorts them over to the dining room table. Our dining room and living room are really the same room, with the dining room sitting just off from the kitchen.

As they sit, Mrs. Powers asked, "What are you three guys up to this summer?"

"I start a job with Big D's security next week," I said.

Tim answered, "I'm working down at Joe's party store."

"I got a job with Green's Landscaping, and I started about a month ago," Dave answered.

"Oh, I thought you had to be 19 to work there Dave," Mrs. Powers said.

"Yes, you do. They hired me because I turn 19 in two weeks. The boss man said he needs young strong men, and he could train me. When I turn 18 then I will be able to go out on jobs with one of his crews. I tried to talk Tim and Mike to work there, but they both already had jobs lined up."

"Are you going to have a big party for your 19th birthday?" Mrs. Hill asks.

"I'd sure would like to, but my mom said no, and I don't have a place to have one," Dave said.

Mrs. Hill turns to my mom, "Kathy, Dave is turning 19 in two weeks. You have a good size basement why don't you let him have it here."

"I don't think so. Jack will be out of town," Mom replies.

"Well he needs to have a party. I know the four of us can be here to make sure it doesn't get out of control." Mrs. Powers adds.

"I still don't think so." Mom says looking at Dave. He is giving her a real sad face hoping she would change her mind. Then she adds, "I'll have to think about it."

As we play on the x-box I am listening in on my mom and her friends. They are very competitive and I hear them getting on mom about throwing Dave a party, but she stood her ground and kept saying no.

----------

A few days later as I came through the door mom says, "Mike, about that party for Dave. I talked it over with your dad and he said it will be ok, but only ten people max and no more. Plus my friends will be here to help me chaperone since your dad will be out of town."

"No problem because we decided we would go down to the Back Door Saloon that night around 10 PM."

"I'm glad you're going to do something for Dave. I know you can get into the saloon at 18 but you can't drink any alcohol." Mom just had to remind me.

"I know, but we were going to try to pick up some girls our age and dance."

"Well that sounds like a plan," she says pleasantly.

"Can we can meet up here around five before we go? We can shoot some pool before hand."

"Sure, but remember no more than ten people."

"Yes mom."

I go upstairs and send Dave and Tim a text about what mom told me.

------------

Later that day I walk into the kitchen where my mom is, "Hey mom I need to let you know that Dave has invited a few guys from where he works."

"As long as there are no more than ten total here at the house I'm ok with it."

"Well yeah there will only be ten of us but some of the guys are in their 20's." I hold my breath, hoping she'd be OK with it.

"In that case I need to meet them to make sure they understand no alcohol."

"Dave already told them."

"I'm sure he did, but I would feel better if I met them beforehand."

I was feeling a little humiliated that she didn't trust Dave or me. I tell her, "Ok, but I think you should trust us, besides you and your friends will be here to check."

"Alright you win but we will be checking." She said.

-------------

Today is Dave's 19th birthday and mom had me cleaning up the basement. I tried to tell her we would only be here for a few hours, and it didn't need a big clean up. But she insisted that it had to be cleaned. Around four, mom's friends show up. They all come down to the basement to ensure that I had done a good job on cleaning.

They finally give their approval and we all go back upstairs. Around four thirty the doorbell rings.

Its Tim. "Hey, Hello ladies and you too Mike. Oh, I spoke to Dave he said they will be here shortly."

"Cool," is all I say and Tim and I head down to the basement. Before I get to the bottom of the stairs the doorbell rings again. I turn and run back up the stairs to answer the door. It is Dave and his friends from work.

"Come on in guys," I say.

Dave is the first to walk in followed by a small group of six guys. They all seem to be in their early to mid 20's. They must all have the same wardrobe because they all wore a pair of tight fitting jeans and a tight T-shirt. Their muscles seem to want to rip right thru their T's. All six look like they haven't shaved for a few days. With all that said they are handsome in a ruff way.

Dave speaks first. "This is Mike and here are the ladies that I've been telling you about. Please stand up ladies and let me introduce everyone."

"Ok!" My mom said as the ladies stand.

Pointing at my mom Dave starts to introduce the women. "This is Kathy May, Mike's mom. I hope you didn't mind me using your first name."

"No, that's ok." Mom says.

"Good standing next to Kathy is Kay Peterson, next to Kay is Sue Powers and finally Jane Hill." Dave is grinning from ear to ear, now looking at the guys who have all filed into the room. Dave continues, "Ladies this here is my foreman Jake, next to him is Bob, Rich, Sam, Josh, and the guy with the camera is Sean."

Jake jumps in. "It's great to finally meet you. Dave talks about you ladies all the time. Trust me it's all good. Kathy, I hope you don't mind me calling you by your first name?"

"No that's fine Jake." Mom answers.

Smiling Jake continues. "Good, good, I know you said no alcohol but I did bring a gift for you fine ladies. It's a bottle of wine for each of you. Plus one for you to enjoy tonight. Don't worry there is no alcohol for us guys tonight. I hope you're not upset about this and will accept my gift."

Before my mom could say anything Sue answers, "Thanks Jake, we'll enjoy your gift."

My mom gives Sue a dirty look. Then turns and smiles at Jake, "Thanks Jake for the kind offer and we do accept."

Jane heads to the kitchen, "I'll get some glasses for the wine. Don't worry Kathy I know where they are."

Kay follows Jane and says, "I'll help her."

"Ok guys we're in the basement let's go." I tell the guys. As the guys headed down to the basement Jake was still talking to my mom and Sue while Sean took pictures. I'm not really understanding what or why Sean felt he needed to film everything.

I was waiting on Jake not really paying attention to what Jake was talking about with the women. I did notice my mom and Sue laughing at what he was saying. Jane and Kay return with the glasses and Jake opens the bottle of wine for them and even pours their first glass.

As I close the gap between me and the group I could hear what Jake was saying, "This wine is home made by one of our customers. It's very good and I hope you enjoy it. I'll come back up in a while to see if you liked it."

"Thanks for the wine and I'm sure we will enjoy it, but if it's not good we will be honest and tell you," Sue says.

"That's all I can ask for, enjoy." Jake gives me a smile on his way downstairs.

As I head down after him, I hear Jane say, "That Jake sure is cocky."

"Yeah, he may be arrogant, but dam he's hot," says Sue.

"Damn all of them are Hunks!" adds Kay. Then I was out of ear shot and didn't hear anything else.

------

We are shooting pool and getting to know one another. Jake, Sam, and Bob try to see who could bullshit the best; all three of them have silver tongues. They should have been used car salesmen, because they could talk about anything and everything. They were guys who could walk into a room of strangers and you would think they have been friends with them for years.

To myself I think, "The women were right these guys do have an arrogant cocky attitude, especially Jake."

It is Bob who shouts out, "Fuck Dave hands down your right. Those four bitches are MILF's."

"So you believe me now," Dave answers Bob.

"Maybe we should invite them down here to join us," adds Rich.

"You guys know they're married," I say.

"Doesn't bother me Mike, not one bit," Josh says laughing.

"Hey Sam come with me. I think I'll go check and see if they enjoyed the wine." Jake says.

We all watch Sam and Jake walk up the stairs. I look at Dave, "You having a good time?"

"I think it's going to get a lot better in a few."

"You mean once we get to the club?"

Dave laughs for some reason, "I'm hoping before we go to the club."

Bob, Rich, and Josh break out laughing. I look over at Tim and he doesn't get the joke either. Sean must be real shy because he hasn't said much all night so far. He just takes pictures and smiles.

It must have been about 30 minutes since Jake and Sam went upstairs, but I wasn't really paying much attention since I was in the middle of a pool game with Tim. Then I hear footsteps on the stairs coming down to the basement.

It's Jake and damn he has the ladies right behind him. Jake sees me looking and with a smirk, says, "Hey Dave you didn't tell me these girls are teachers. Plus they teach at the same school you go to. Damn I would have done better in school if we had fine bitches like this at our school."

I thought for sure mom and her friends would have hit Jake for calling them bitches, but nothing happens. They are just smiling and each of them has a bottle of wine in their hands.

Dave is smiling. "I didn't think about telling you."

"Well, they have decided to come down and join us. They like the wine so much they're going to drink the other bottles that I gave them. Hope you guys don't mind but Kathy still insists that you all don't drink while you're here."

I noticed Sean is taking pictures of the group coming down the stairs. As they walk into the room, Jake takes them over to where Dave was standing. I also notice Sam wasn't with them.

With a smirk Jake is talking with the ladies, then says to Dave, "Ok, Dave you're in luck tonight. These bitches told me they're going to give you a big birthday kiss."

I still don't understand why these four teachers have not jump down Jake's throat for calling them bitches. Something just doesn't feel right to me.

"OK who's first?" Dave asks.

Jane walks up to Dave and gave him a kiss on the check.

Jake frowns. "NO, NO, NO! We agreed on a good proper kiss. On the mouth with tongue. Come on Jane do it right now. It is his first time being kissed as an adult, after all."

Jane looks at Jake then leans in and gives Dave a big wet kiss on the lips. Their kiss quickly turns to them playing tongue hockey! When she is done Sue takes her turn and gives Dave another big sloppy kiss. Then Kay takes her turn.

When it is mom's turn, she looks at me first. Maybe she wants me to intervene. But I'm just watching.

She smiles at Dave and says, "Happy birthday Dave. I know you've wanted this for a long time." She then leans in and gave him a wild kiss which also included a lot of tongue.

Jake again smirks. "Ok Mike let's get some dancing music on. Now, ladies you all need to give Dave a good slow dance and then dance with the rest of us."

I can't believe what I'm seeing. Mom and her friends are doing everything Jake tells them. I would never have believed my mom would kiss Dave like that, and now she is dancing with him! I guess the wine must be pretty strong.

I make sure to cue up some slow dance songs. We watch as each one of the mature women give Dave a long slow dance. When they finish dancing with Dave they start dancing with the rest of us. As everyone danced Sam came back down the basement with a few more bottles of wine.

"Ok, Just as you asked for: a few more bottles of wine." Sam says, looking at me he continued, "They enjoyed the wine so much they wanted more for later."

After a while Jake and his friend have the women off to one side of the room. The women, along with Jake and his crew seem to be having a good time. Everyone is laughing and smiling.

Dave, Tim and I are shooting pool when Jake yells out, "Hey Dave we need a judge over here. We're having a contest to see who has the sexiest bra on."

My mom whispers something to Jake. He laughs, then looks at me. "You don't mind, I hope because your mom thinks she is going to win."

"Knowing how competitive these ladies are even if I did mind they're going to do it anyway," I reply, laughing.

Dave moves over to Jake. "Ok how does this work?" he asks.

Jake takes charge. "Ok line up ladies. Make sure there is some room between you. Kathy since this is your home you're first. Dave get over here and stand in front of Kathy." The women all move until they were in a line. Dave gets in front of my mom. Tim and I move to where we could have be a better views. Sean is still taking more pictures.

The women are all wearing jeans, with my mom, Jane and Kay having on pull over tops. Sue is wearing a button down top. Nothing sexy, just normal tops.

Jake looks around and seems happy where everyone was. "Ok, Kathy take your top off. Don't worry about Mike. He must have seen you in a bathing suit before?"

Mom smiles at Jake and looks at everyone but me before she starts pulling off her top. I am excited about seeing my mom take off her top not just in front of me but also in front of Tim and Dave. Dave has had the hots for her as long as I can remember. This is so hot. Plus there are six guys she hasn't met before.

She reaches down and slowly pulls her top over her head. I watch every move she makes. I've seen her in a bathing suit but for some reason this just seemed different. As she pulls her top off, her bra comes into view. Its just a plain white bra. Not sure how she figured she was going to win. As her top passes her bra, her boobs bounce a little. She finally gets it over her head. Jake holds out his hand for her to give her top to him.

Dave makes sure he checked her out by looking over every inch of her. Dave then says, "Next."

Jane is next Dave moved over to stand in front of her. She also pulls off her top over her head and hands it to Jake, who was handing over to Bob. He puts them on a counter by the dryer. Her bra was red and lacey. Dave makes sure he checks her out too. Kay is next she was wearing a large black bra.

I'm thinking Sue's got this if she has on anything but a plain bra. Dave is now in front of Sue. She has on a white button-down blouse. She slowly unbuttons her blouse starting at the bottom. As she unbuttons her brown bra slowly comes into view. Then she opens her blouse and takes it off. I am disappointed all the women had on plain white bras.

Dave announces, "It looks like it's a four-way tie."

Sam says, "we got to have a winner." All of us guys agreed. Even the women seem to be in agreement.

Jake smiles at Dave, "Let me think. You four go ahead and have some more wine."

I was off to the side when I hear Dave say, "Why don't we exchange phone numbers, that way I will be able to thank you for a wonderful party."

The MILF's all laugh and one says, "okay I don't see the harm." Dave smiles as all of the girls added their numbers to his phone, then added his to theirs.

Sue finishes adding her number to Dave's phone and grabs her glass. "Hey we're almost out of wine. Do you have any more? It really tastes good."

"Got it covered," Sam says as he runs up the stairs.

The women are sipping on their wine and talking with Jake and Bob. I try to listen in but can't hear them. A few minutes later, Sam comes back down the stairs with four more bottles of wine.

I was starting to wonder where all the wine was coming from. The girls must have finished off at least two bottles each. I would have expected them to be completely drunk by now. They aren't acting drunk but seem to be okay with any suggestions Jake gave them.

Jake turns around and smiled at Dave and the rest of us and says, "ok the women have agreed to see which one of them has the sexiest panties on." He crows. "Ok ladies line up again same as last time. Dave get over here you're still the judge."

Everyone moves into position. I make sure I have a good view again. I can't believe mom and her friends are going along with all of this. I'm not sure why, I guess because of the wine, but neither mom nor her friends would ever have agreed to stripping normally.

I think about putting a stop to it all, but my cock is hard as a rock and overrides my thoughts.

Jake makes a few adjustments with where the women are standing. "Ok Dave start with Kathy first again."

Dave moves in front of my mom, "Ok, Kathy let us see what you got on."

She smiles at Dave, then reaches down and slowly unzips her jeans and then pulls them down her long legs. As her white granny panties come into view everyone kind of sighs because there is nothing sexy about her plain white panties. After she finished stepping out of her pants, Dave just smiles and checked her out from head to toe. I look at him and chuckle. He is practically drooling looking at my mom almost naked.

Dave moves down the line, inspecting each woman. None of them are wearing anything that even looks sexy. Jane has on blue panties, Sue has on s red thong, and Kay has on white panties with red dots all over them.

Dave announces, "sorry to have to say this again but it's a tie."

Sam adds, "guess we're going to have to think of something else to get a winner."

Jake looks at Bob and nods. Bob goes over and picks up the ladies jeans and puts them on the counter with the tops.

Sue notices what Bob did and says in a loud voice, "hey give us our clothes back!"

"Not until we have a winner. Anyway, you sexy ladies need to dance with the judge. Hey Rich, lets listen to your play list. I think you have a much better song selection."

Thecsm
Thecsm
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