Summer Pool Fun

I want to give thanks to HeyAll for his help on this story.

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Summer is finally here and I just turned eighteen years old. As always I bought a summer pass at the community pool, where I'll hang out most days. I will be graduating next year.

In school I was on the cross country and track team. An average student and of course, like most average young men, I was obsessed with sex. Due to my overwhelming shyness I'd only had a few girlfriends.

This summer vacation started out the same as always with me hanging out at the pool. I noticed that Gray and his small group of friends were at the pool most days. Trust me, they were a group of ass holes. They were all on the football team and loved to bully whoever they could. I knew them but didn't hang out with them. Like me they all were eighteen years old.

Gray was very different to me. He stood 6'0 tall and was muscular. All the girls talked about how attractive he was. No matter how much he bullied them he constantly got laid every weekend. Girls who were with him told others how big his package was and they didn't care if he was a bully.

I guess I was jealous of him, as I was nothing like Gray. I was 5'8, skinny, and not on the football team. Girls wanted to date the football players and purposefully ignored us guys on the cross country team.

Since my mom was a schoolteacher she got the summer off. She also had a summer pass to the pool. This year she talked three of her teacher friends into also getting pool passes for the summer. They went early in the morning to swim laps. I always went after the pool was open for everyone else. I enjoyed not being at the pool the same time she was there.

Mom's friends names were: Pam Taylor, May Brown, and Kathy Miles. At thirty, Pam Taylor was nine years younger than my mom. She was also married and had two kids. All of my friends thought she was one hot teacher. To top off her sex appeal, her long, wavy black hair fell down her back, past her shoulders.

She stood about five foot and five inches with a very impressive figure. She was a full, beautiful woman, not fat or even plump, just built like a brick house. At school, she always wore a dress or skirt which showed off her long, muscular, smooth legs.

Particularly eye-catching was her gold necklace, which hung right between her cleavage, drawing your eyes to her impressive breasts. Back in school I was in one of her classes, and had fantasies about being with her.

May Brown was about 12 years younger than my mom with two little kids. She still hadn't lost all the weight after having her last kid. I remember her telling Mom that she was excited about swimming, hoping it would help her get back into shape. She had a very cute face and a great rack.

Kathy Miles was also nine years younger than my mom. She was married with two young kids and worked out a lot with my mom. She had long red hair, normally tied up in a ponytail at school. She seemed to always wear dresses or pencil skirts that showed off her figure, She was always friendly with the students. The guys were always finding ways to talk with her and she clearly enjoyed the attention.

After school hours Mom and Kathy enjoys working out regularly in the school gym. During cross country or track season they sometimes ran with us and they would wear tight jogging shorts. One time I caught some teammates of mine running slower on purpose so I dropped back to see what was up. They were watching Mom's and Kathy's asses while they're running, making crude remarks amongst themselves.

Guess I might as well tell you about my mom. Called June Hill, she attended church regularly. She stood about five foot and four inches. Even at thirty nine years old, she was hot, if it's not too weird for me to say that. She had straight shoulder length brown hair and green eyes.

I loved looking at her legs, enjoying the sight of how toned they were. This might sound crazy, but I really couldn't resist imagining the things you could do when looking at her fine ass and runner's legs, developed through her gym workouts. My friends all said she was a MILF.

Mom knew she was attractive and in fact didn't hide it. She even went out of her way to flaunt her physical assets when she noticed a guy checking her out. At school she always played down her physical assets, but it didn't stop the guys from checking her out. When she was hit on she always turned them down. She did enjoy flirting but never led anyone on, making sure they knew she was married.

The only bad thing about my mom being a teacher was that she taught at the same high school that I attended. I knew the teachers not just as my teachers at school, but also as friends of my parents. Only my friends and a small handful of other kids knew my mom and I were related.

Now that I told you about my mom and her friends let me get back to the story.

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I tried to get to the pool every day around noon before it gets to crowded. This year I noticed that a lot of college girls were there. Maybe they were always there, but I'm just noticing them more. I'm a people watcher and always found a place where I could see most of the pool. Gray and his friends were also there everyday.

I started to notice once a week Gray and his gang would surround one of the college girls and one of the guys would figure a way to take her top off. Then he'd play keeping away from her, as she held her tits trying to get it back. They made sure none of the underage kids could see and would move her to an area where the cameras at the pool couldn't catch what was going on.

The life guard at the area was a college guy and he would just laugh at the game. Once they had the young lady where they wanted her, they would make her show all the guys her boobs before giving her top back. None of the girls ever got mad, they seemed to enjoy the game as much as the guys. What the girls didn't notice was that one of the guys was always out of the pool with a camera.

This went on for a few weeks and all the adults at the pool heard about what was going on. One day the life guard was walking with Gray.

Gray saw me and called out, "Hey Mike you want to see some pictures?"

Like I said I wasn't friends with him but we did talk from time to time, "Sure, what you got some pictures of some wild life?" I said laughing.

"You could say that", he replied, as he handed me his phone.

As I looked at it I could see all the pictures were of the girls in the pool topless. "Wow, how did you get them to show you their tits?" I knew why but I wanted to hear his tale.

"Guess you can't see us in the pool. We steal their tops and before we give them back they have to remove their hands from their tits and show them to us."

"And they don't mind?"

"Not at all. It's all fun."

"Wow" was all I could reply.

"The best part is I and a few of the others have had sex with them."

"No way man. How did you work that?"

The life guard laughed. Gray looked around to make sure no one was close by, "You keep a secret?"

"I want to know, so ok. My lips are sealed."

"I show them the pictures I have of them showing us their boobs. Then I tell them if they don't want everyone else seeing their rack they have to have sex with me."

"So you're blackmailing them"

"Well I like to call it a business deal."

"You're crazy"

"Yeah, I know. Would like to get one of these MILF."

"I know four MILF, I think you can get." The life guard said.

"Really! Where?" Gray asked.

"In the mornings, during lap time. There is always four MILF doing laps every morning."

Gray smiled and I could see he was thinking. The life guard continued, "You'll have to get here around seven in the morning. I've never seen you do four at the same time, but if you want these four you're going to have to."

Gray took his phone back and walked away, talking with the life guard.

The next day at the pool Gray's gang was there but no sign of him. I didn't think much about it. Gray stayed away from the pool the rest of the week. On Friday Gray wasn't at the pool and his friends weren't there either. I figured he'd found something more interesting. A few weeks later I found out what it was.

On Monday Mom and her friends returned from the pool before I left. I'd started to come down the stairs when I heard May talking, "Hey I don't know about you guys but I haven't done anything like that since college."

"Yes it was fun, but those guys were students at our school. I know they were all eighteen, but it doesn't make it right," Pam said.

"It may not of have been right but I don't think we had a choice," Kathy added.

"Of course it wasn't right. All we can do is hope they don't open their mouths and tell anyone," my mom said.

Kathy laughed, "Stop being upset, even if they told anyone we will just deny all of it. People won't believe them. So Ladies just make it up as a fun day. At least I had fun."

"Here's my two cents if anyone cares. For being young that Gray has a commanding presence about him," May added smiling.

They were all giggling as I entered the room. When they saw me they became quiet and looked at me or should I say stared. I stopped in my tracks, "Are my clothes on backwards?" They all started laughing and said "NO!" together.

Shaking my head I left them and went to the pool. About fifteen minutes after I arrived Gary came up to me. "You said you can keep a secret and I'm holding you to it."

"Ok. Look I haven't told anyone and don't plan on it."

"Good, Your mom is a teacher right?"

Raising my eyebrows I said, "Yes and?"

"Her friends are over at your house all the time right."

Again I said "Yes, what's it to you?"

"Have you ever seen them topless? If no, would you like to?"

Not knowing where he was going with this, I replied, "No, but yes I would love to see them topless. I would love to see them completely nude, but I don't ever see that happening."

Gray laughed, 'Tell you what. I can make that happen. Are you in? Before you answer watch this." He tossed a flash drive to me, then continued, "Give me your answer tomorrow." Before I could say anything he was off.

That night I went to my room and put the flash drive into my computer. There were a few files on there for pictures and one with a video. I selected the video.

The first part of the video showed the pool, it looked empty. You could see that it was set up for lap swimming. Then Gray and a few of his friends came into view. The camera moved over to where the women's locker room area was. Mom and her friends were just walking out of it. Wow, they were hot in their swimsuits. It had been awhile since I'd see Mom in a swimsuit. Each one of them had on a two piece suit. The camera followed and Gray and two other guys walked up to them. There was no sound but you could tell they were talking, everything seemed friendly at this point. After talking the women moved so they could start doing their laps.

The camera must then have been turned off because the next scene showed the women holding their breasts and chasing the guys over to the side of the pool. I wasn't sure how Gray and his gang got the swim tops off the women but I guess that really didn't matter. Once Gray got to the edge of the pool he jumped up and sat on the side with his feet still in the water, holding all four tops in his hand.

The women finally caught up. With only their heads out of the water and their hands covering their boobs they looked up at Gray and yelled at him. The cameraman must have been close by now. I heard Gray yell out "Shut-up!!"

It went very quiet, the camera was focused on the women. One of the women yelled out "Give us our tops back now, ass hole."

Gray shouted "What part of shut up don't you understand!! I'm in charge so listen up! If you want your tops back you're going to do what I tell you!"

Then I heard someone yell, "FUCK YOU ASS HOLE!!"

Laughing Gary quipped, "Is that any way for a teacher to talk?"

"Just give our tops back now or..."

"Or what" Gray answered. Looking around he then continued. "I see there are a few more people entering the pool area, hmm, mostly men. I guess you can get out of the pool and give all of us a show. Or just do as you're told."

"What do you want?" Mom asked.

"Well all we want is to see your tits. So stand up, drop your hands and let us see them. No-one else will see with us standing around you."

The women just stood there and looked at each other then at Gray. They looked around the pool area that they could see from their position. With a commanding voice Gray continued. "Look Ladies you're wasting our time." He paused for a few seconds, he abruptly said, "Show us your titties."

"Excuse me? I don't think so," Mom said angrily.

"I'm getting pissed. You're wasting our time. If you want your tops back then show those titties," he replied with no hint of compassion.

"You're breaking the law!" Pam forced out with a whisper..

"Well then if that's how you feel. Let's go guys," Gray replied. He turned, still holding their tops, and started walking with the guys following.

"No wait, please, let us talk some more" Kathy yelled out.

Gray turned and gave them a real mean look, "Ok, don't take too long. We're not going to wait here all day!"

The women got in a very close circle and whispered to each other. As Gray moved to sit again, the guys returned to their positions around the women. Everyone was watching them at this point.

Gray shouted, "Goddamn you four bitches make up your minds!"

Kathy looked at him and said, "Ok, we'll do it."

Gray smirking now, "Ok, stand up and drop your hands to your side so we can get a good look."

The women were all facing Gray as they stood up. May was closest to the camera and her tits were the first I saw. They were a nice size, her areolas weren't very big and very light pink in color. Her nipples were small but hard. They could be hard because of the water temperature, who knows.

The camera then moved over Pam, her tits were about the same size as May's, but her areolas were much larger and a darker pink in color. Her nipples were larger and much more pointy.

Kathy was next, she had the biggest tits I've ever seen and every time she moved, her tits bounced. I wondered how she hid them. Her areolas were much larger and brown. Her nipples were also much larger then the other two and pointed out, making them look long.

Mom's were the last set of boobs to come into view. My Mom being the oldest of the group, had boobs that sagged a bit more than the others. Her tits were larger then May's and Pam's. Her areolas were very dark and large as well. Damn, her nipples when hard must have been at least an inch long.

Gray looked at the women and issued an order, "Ok, Ladies, turn around so everyone gets a good look at them sexy mature titties."

Slowly they started to turn around and showed everyone their boobs. Someone shouted, "You all have a great set sweet hearts!"

It sounded like each guy made sure they commented on their tits. As the women turned their boobs bounced and damn, my cock began to get hard from watching. As my eyes continued to stare at the boobs on the screen, I could see in their faces the embarrassment from being topless in front of these guys.

When the women were done showing everyone their tits Gray yelled out, "Ok bitches. Thank you for the show!" He then threw them their tops back and got up and left. That was the end of the video. Damn, I watched the video a few times before I put it away.

On Tuesday I got to the pool about the same time as always. There was Gray sitting at a table and he waved me over. Damn, I really didn't like this guy. I needed to ask him some questions before I made a deal with the devil. I walked over to where he was sitting. I noticed nobody else is around that area yet.

"So how did you enjoy the film?" Gray asked.

"I can't lie I enjoyed it, but before I agree to anything I have some questions. I know you blackmail the women, I don't want these ladies to get a divorce or lose their jobs. They are good teachers."

"I agree with you. That's why I only want you involved. Nobody else will know. And I don't blackmail, I make business deals."

"OK. I'm in, but I don't want them to know I'm involved right now."

"Deal."

We talked about the how's and when's. I told him I wanted to watch and that I had a web page that I never did anything with. I suggested we could film and upload it to that web page, I was the only one with the password. I had cameras that we could set up wherever he planned on doing this. He told me nobody was at his place during the day. So we left the pool early. I went home and got my cameras, luckily Mom wasn't home. I went to his place and set up the cameras and made sure they and the web page worked. We agreed he would start his part the next day and Thursday was 'it'.

On Wednesday I was getting ready to head out to the pool when Mom got back from doing laps. She came in looking upset about something. "Hey Mom are you ok?" I asked.

She gave me a nasty look "Yes, yes everything is ok. It will all work out in the end I guess."

"You get in a fight with your friend or just a bad pool day."

She smiled, "Just a bad pool day for all of us. You don't need to worry, I'm ok."

With that I headed out to the pool. Gray was there waiting on me again. "Hey, people are going to start thinking we're friends, ass hole." I said to Gray.

He laughed, "Well looks like we might be headed that way."

I told him about the mood Mom was in and he was happy about that. He didn't tell me what he told them, but that they need to be at his place by eight am. Later in the day we checked to make sure the web page and the cameras were working. I made sure I could tape what happened from the web page. Still not sure if this was a good idea or not, but my cock was overriding my head right then

On Thursday morning I got out of bed early to make doubly sure the web page and the cameras were working. I also reconfirmed that I could tape whatever happen that day. Then I went to the kitchen just in time to see Mom put her coffee cup into the sink. She looked in a much better mood than yesterday. She was wearing jeans with a red button-down blouse and heels. "Doesn't look like you're going to the pool today," I said.

Smiling, she replied, "Yes, us girls are going to breakfast and then we'll hang out all day; maybe get some shopping in."

"Have fun."

Just then the door bell rang. It was May and she and Mom left. I text Gray to let him know that they had just left. I then got my computer and set it up. Gray had the cameras. I still didn't know if this was a good idea. I guessed I could still get over there if I needed to stop this, what ever this was.

It was about an hour later when I heard Gray's door bell on the computer. So I sat down and started to watch the live show. Gray came into view and opened the door. All four of the teachers walked into view. Gray was smiling but I couldn't hear what was being said. The women moved over to the couch. They all sat down with Gray in a chair across from them. He had removed the coffee table that was there the other day.

Gray started, "Thank you for coming over and on time."

That's when I noticed there were three other guys in the room. "Hey!! It was suppose to be just you Gray! Who are these guys and why are they here?" Pam shouted.

With a smirk on his face, Gray replied, "That's Joe, over there is Jake, and this is Mike." The three guys just smiled. Gray continued, "They're here because I asked them to be here. So just live with it."

May talked next, "We're not here to socialize with you. Tell us how much you want so we can move on from here."

"Look Ladies, I don't want your money. What I want is you four bitches to do everything that I tell you. Or I'll send these pictures to the School Board. Your husbands might understand but the school won't. Yes, we are all 18 but we are also students. I don't think you'll talk yourselves out of it."