Two MILF Crazy Weekend

I want to give Ortay a thank you for helping me edit this story.

My name is Jack. I turned 18 a few months ago and just graduated from High School last week. I start College this fall and will be attending the same school as my best friend Dave. He is 19 years old and a year ahead.

We both work in the summer for my dad who owns a landscaping company. It's made both of us very buff and eye candy for the ladies.

Dad turned to me at dinner, "Ok Jack, you have had enough time now to goof off. I expect you to be at work come Monday."

"Yes sir." I replied.

"By the way, when will Dave be back? Is he planning on working again this summer?"

"He will be back this Friday I think."

"Tell him I need him on Monday as well. We have a big project and I need you two to help lay some sod."

"I'll let him know."

Dad then looked at my mom, "Hey I'm glad you and Jane have become good friends. It helps with you giving her referrals. She has been able to get us a lot of new clients."

Mom laughed, "I try. Yeah she's great, we've even going to the movies this weekend."

"Hmm, well be careful she is a lot more outgoing than you. Don't need you getting caught up in anything!"

"Don't be silly! She's married too. She just likes having fun."

"'Fun' huh? I know what you're like." Mom didn't reply, just looked at dad and laughed.

My mom works for a real estate company. After a sale she always drops by dad's business to give referrals.

People who just bought a home who might want some landscaping done. Jane had been working as dads new sales rep for a few months. My mom and Jane have become very close friends.

They'd been going out almost every other night recently and spending a lot of time together.

Jane is nine years younger than my mom. She is married, has two young kids and works out a lot like mom but not at the same gym. She has long red hair which is normally tied up in a ponytail at work.

At work she loved to wear tight dresses or pencil skirts that show off her figure, I guess she's pretty flirty. The guys are always finding ways to talk with her and she clearly enjoys the attention.

My mom is 5'5", she is always complaining that she can not get below 130 pounds. I'm not sure why she complains because I think she looks good.

The simple truth is my mom is a MILF. She has long blonde hair with hazel eyes. She works out every day, has well-toned legs, a slim waist, and a little definition on her arms and ass. At work, she wears dresses that show off her body. It just so happens that her sales have always been very high.

Dave and my other friends have always loved coming over to my house, usually just to get a glimpse of my mom, I can't blame them. They always mention what a MILF she is and how they fantasize about her. Trust me I've had plenty of my own fantasies about her.

After dinner I sent Dave a text informing him that dad needed him at work on Monday. He was on board.

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On Monday Dave and I headed over to dad's job site. Mac, the foreman for this job, was already waiting for us.

"About time you two got here. We need to get this yard done today." Mac yelled out to us.

We knew what to do and started working.

After about an hour of working, we took a break. Mac asked Dave how school was going.

"It's ok, this past year I got all B's." Dave replied.

Mac smiled, "Hey did you get to meet the new office girl?"

"What new girl?"

Mac was laughing, "Didn't Jack tell you about the hottie? Guess Jack wants to keep her to himself." We all laughed at that.

I jumped in, "We didn't stop by the office, anyways she is married."

We finished the job around 3 P.M. and headed to the office. We looked nasty with all the dirt on us and as always we forgot to put on our shirts.

As we walked in Jane noticed us right away. "Well it seems our young studs are done for the day."

Dave's eyes got big as he looked at her. "Well, we might be talked into staying for someone like you."

Jane walked over to Dave. "So you're the new guy? You need to fill out some paperwork if you want to get paid."

I left the two alone for a while and went to get some water, and to let dad know we were back. I'm sure Mac already told him the job was finished.

As we were getting into my truck Dave said, "Wow, your dad was sure lucky getting her to work here. Have you checked out that body! And what a rack on her, and that ass! Oh my god, that ass! Dam, I think she was even hotter than your mom."

Jack chuckling, "I wouldn't mind having some fun with her, but she is married."

"Tell you what Jack, I'm going to see if I can seduce her."

"Good luck with that Dave!"

"You know, I've never had trouble getting the ladies once they catch a glimpse of my cock."

"Your kidding right? It's not the size that counts, its how you use it!" We were both laughing now.

"Nah, when your cocks as big as mine you don't need to move it around. They just want to try it, see if they can take it all in. You know how guys drool over women with big tits? No matter what they tell you, every woman wants a big cock at least ONCE in their life."

"Well you might be right but she is still married."

"Trust me everyone, man or woman, given the right opportunity will cheat if they think they can get away with it."

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From that day forward whenever Dave and I walked into the office, Jane went out of her way to make sure she greeted us. Dave would start flirting with her and she would always flirt back harder.

It was like a game and the stakes grew every day. After a few weeks, it started to look like they were in some kind of relationship. Everyone at the company started talking about them. So my dad asked me to find out.

The next day on the job site Dave and I were working together so I asked him about it. "Hey Dave what's going between you and Jane?"

Dave looked at me, then looked around to see who was looking. When he figured out it was just the two of us he said, "Don't tell anyone but we've gone past flirting now. "

"Ok, what's going on?"

"You can't tell anyone! As you know we've been flirting with each other all the time but she also been flirted with other guys. One day I was in the restroom.

I forgot to lock the door and she just walked right in. I was taking a piss and she saw my cock! She couldn't take her eyes off of it. She was actually speechless."

He looked around again to make sure no was around then he continued, "She walked up to me and waited until I had finished. She grabbed my cock and stared sucking me off. I couldn't believe it. Since then she's been giving me blowjobs after everyone has left to go home."

With a look of shock, "You're one lucky guy Dave."

He continued, "It gets better, we even fucked one time in the restroom. My folks are going to be out of town in a few weeks for their vacation. I'm trying like hell to get her to stop by so we can have more than just a quickie."

"Dam, you better keep me informed man."

"I will. Just don't tell anyone else. Don't need her husband to find out or for her to get fired over it."

"I won't say word."

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A few days later Dave came up to me, "You're not going to believe this! Jane's husband has to go out of town for a business trip next Friday. She has a babysitter and will be coming over to my place. Luck is on my side."

"You sure a lucky guy. You know I'm not going to believe you unless you have some pictures though."

"You're a sick bastard. Of course I'll have photos"

We both had a good laugh and off to work we went.

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Next day Dave was looking down so I asked him, "What's wrong?"

"My roommate from school is coming to visit same time Jane and I are having our weekend together. I knew he was an asshole, but I did tell him to stop by so I could show him around."

"Just tell him it's a bad weekend."

"I tried, but being the asshole he is. He's still coming."

"Then set him up with a date?"

"Good idea, but who?"

"Since Jane is going to be with you, just ask her if she has a friend who would help you out."

"Good Idea man." Just then someone yelled for us to get back to work.

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"Hey, Jack!!" Dave yelled

"Hey man what's going on?"

"That was a great idea you gave me a few days ago."

"What idea?"

'Asking Jane to bring a friend. She found someone. She won't tell me who but said it took her a lot of arm bending to get her friend to agree. Anyway, I think we're good."

"Cool, hope all works out for you."

"It will! Even if my roommate is an arrogant prick. Maybe he'll be cool this weekend."

"You got him a date. He owes you. It will work out."

"Hope so, but he doesn't take no from women. He keeps pushing until they give in."

"Don't worry, as long as you and Jane have fun."

That night at dinner dad was talking about mom's 40th birthday coming up. Looking at my mom dad said, "Don't forget we're having a big party for you Hun."

"Thank you for wanting a big party for me, but I'm having a big girly weekend with Jane. Her husband is gone and we're going to celebrate me being 40 like we're turning 20 again."

I choked on my food when I heard my mom say that. Mom looks at me, "Are you ok Jack?"

"I'm ok. Guess I need to relearn how to eat."

Dad looked worried, "I'm not sure I like the idea of you and Jane out partying all weekend."

"Oh, don't worry. She is married, and so am I." She smiled reassuringly at dad, "We're not going to get into too much trouble. Her husband is out of town and we figured it would just be fun. Maybe we will just run up to the casino."

I got up from the table while they were still talking and went into my room so that I could send a text to Dave. "I know who the blind date is... It's my mom!"

It took a few minutes before I got a text from Dave, "No shit. How you know?"

"At dinner tonight, mom told dad she and Jane had plans for this weekend."

"You think I should tell Jane that I know?"

"NO!! don't tell her. Don't want my mom to know that I know."

"k"

"Hey I want to know everything that happens. I have an idea. Why don't you let me put some cameras in your place the day before?"

"Guess you could do it after my folks leave. Don't want Jake or anyone else know they're there."

"k, give me a key tomorrow and I will set it up when no one is around. You will know about them but you won't know where they're located."

"Good plan. See you tomorrow."

At lunch the next day Dave gave me the keys to his place. I took the next day off from work and sat in my truck outside of Dave's house. When I saw Dave's parents depart for their vacation I waited another 30 minutes before I went in.

It only took me about two hours to set up all the cameras and microphones. I made sure I had them in the living room, all the bedrooms except his folks, and in the kitchen.

I then made sure all the cameras worked. Since Dave's house was right behind ours I made sure I could get a good reception from my house.

After I had everything all set up I went back to work. I found Dave working out in the company's yard, "All set up and ready for tomorrow?" Dave just smiled.

Dave's friend Jake showed up on Thursday night so Dave wasn't at work Friday. Jane was there and asked me if my mom was ready for the weekend.

"I don't know. I haven't heard her say much about it."

I left the office. I couldn't wait for the work day to be over. When I finally got home I made sure my cameras still were working. I saw Dave and Jake sitting in the living room talking. I turned the mic's on so I could hear them talking.

Dave, "I'm not sure who your date is tonight."

Jake, "That's cool, as long as she is fun."

Dave, "Don't get your hopes up man."

Jake, "You know me once I put the charm on, the women can never resist."

Dave, "You mean once you show them that monster in your pants. Or should I say, once you put the moves on them, you don't take no for an answer."

They both had a good chuckle.

Jake, "Man you know, I like being dominant and most women like a man who takes charge."

Suddenly I heard my dad yell for me to go out for dinner. I turned everything off and headed downstairs.

Dad asked me, "You want to go out or stay in and have pizza?"

"Let's just have a pizza tonight and maybe go out tomorrow."

He was ok with that. My mom came walking into the room. She had on blue jeans and a button down top. In tow a suit case packed for the weekend.

Dad gave her a hug, "You have fun this weekend. Hope you win at the casino and don't let Jane get you into any trouble."

"Don't you worry, I will be home sometime Sunday"

Mom looked at me, "What are you doing this weekend?"

"Dave's roommate from school is in town this weekend. So I'm just going to hang out here I guess. Maybe tomorrow go see if any of my other friends are around."

"You can keep your dad company if your staying home." As she left for the weekend.

After mom left dad had me order the pizza. I knew Dave's plan for tonight, he wasn't meeting the women until around 6. They were going out to eat then back to his place. Which gave me a few hours to hangout with my dad.

As we ate the pizza we talked about work and me going to school in the fall. Dad asked me, "What do you think of Jane?"

"Well dad I think she is cute and a hard worker. She does do a lot of flirting with us guys, but that's all it is. No one has said anything bad about her."

"Guess your right."

We talked more about a lot of things but mostly about nothing. I looked at the clock and saw it was getting close to 8. I made my excuse to dad about going to my room to play games. He just smiled as I left the room.

As soon as I got my room I bought up the camera feed. They had not arrived yet. I selected the camera pointing at the door to full screen for now. As I waited for them to show up I played some games on my phone. I heard the door open and looked at the computer.

I plugged in my headset and listen in and watched. Dave was the first to enter, followed my Jane, then my mom, with Jake coming last. They all went into the living room so I turned on the cameras in there.

Jake sat down on the couch, "Dave take the wine that the ladies got us and poor some out." Dave wasn't lying, Jake did come across as dominant.

Dave noticed Jake's tone but just smiled and went into the kitchen. Jane and mom both sat down on the love seat.

The women were talking softly to themselves leaving Jake out of the conversation. Dave walked back into the room with four glasses of wine. He handed Jake a glass then walked over to the women.

As he handed a glass to my mom he said, "Sue why don't you sit on the couch so Jane and I can sit tighter." Wow, he called my mom by her first name.

Mom smiled at him and moved over to the couch but sat on the other end from Jake. Dave gave Jane her glass as he sat down with her.

Jake got up and walked over to Dave and whispered something inaudible into his ear. Dave just looked at him as Jake walked back to the couch. Dave waited a few minutes then leaned over to Jane and whisper something to her.

What was Dave playing at?

Jane stood up, "Sue will you come with me." Mom got up and followed her into the kitchen. I'm glad I put some cameras and a mic in there.

Jane, "Look Sue I'm hoping to have some fun with Dave but you've got to be at least a little friendly with Jake."

Mom, "Ok, but I think he's an asshole. I'm not going to have sex with him, but you're right, I can be friendly."

They walked back into the living room and mom sat closer to Jake this time.

Even though mom did not want to be friendly with Jake she did start a conversation with him. She didn't want Jane and David to have a bad evening just because she didn't like Jake.

Jake, "Glad to see you're not going to be totally rude and talk with me."

Mom, "Oh come on...don't tell me you don't have any confidence. I know I'm older than you but come on we can find things to talk about." Guess mom was trying to make Jake feel unconformable.

Jake smiling, "You seem like a strong independent women out to bag a young stud like me. I'm sure we will get to know each other better and have a lot to talk about."

Mom also smiling now, "Yeah I've known guys like you. Once you get something in your head there is no reasoning with you. You are just too thick headed."

Jake looked at Dave and they both just started to chuckle. They all just started talking and getting to know each other. I stopped paying attention until I heard.

Mom, "So you two guys are saying that women are just like men. Men drool over women with big tits and we drool over guys with big cocks."

Dave, "Well, guess that's what I'm saying."

Jane, "So what are you proposing?"

Dave, "Don't worry it's very simple." He grinned at both women. "Jake and I will take off our clothes and we'll see how it affects you two."

Mom, "Forget it!...I really don't want to see you two naked. Your disgusting Dave."

Jake chuckling, "Hey no need for such hostility just because you are too straight arrow."

"Whatever...If you two young studs have something to prove then take your damn clothes off." She said dismissively.

Jake looked at David and said, "Ok lets get this over with."

David and Jake stood up and stripped down to their boxers. Dave looked at Jane and said, "You want the honors or does Sue."

Jane, "Well it's not going to be Sue." She walked over to Dave and slowly pulled his boxers down. As it got past his cock it popped right out and stood up.

Jane had seen it before and knew how big he was. Mom on the other hand gasped, "Oh, my god." As she saw how long it was. I think it just looked so long because of Dave slim waist.

Then Jake turned to mom, "Ok Sue, its your turn."

Mom walked over to Jake and pulled down his pants hesitantly. Jane and my mom's eyes exploded. They both had a big smile on their faces. Jake cock was just a little longer than Dave's. What made their eyes pop was how fat it was.

Both women just kept staring at their cocks. Looking at one then the other.

Jake, "Dave I think you just proved your point."

Dave laugh, "I know." Both guys went back and sat down. Jane sat next to Dave and started to play with his cock. Mom sat next to Jake but just kept staring hungrily at his cock.

Jake reached down and started to gently stroking his long thick cock while mom watched him. Jake even had the largest ball sack that I ever saw. They hung low and had to be full of sperm.

I could tell mom was mesmerized by his hard cock and was now breathing harder.

Jake could tell she was getting aroused, "Like what you see?" As he continued stroking his hard manhood.

She didn't answer him. That's when Dave said, "Ok ladies it's your turn."

Jane stood up and grabbed my mom and pulled her up also. Mom looked at Jane nervously, "Are you sure about this?"

Jane, "Damn girl you're already in a room with two naked young studs. If you're thinking you'll get into trouble, let me tell you, your already in trouble." Then Jane looked at Dave and Jake, "What happens here stays here boys. Nobody, I mean NOBODY, especially our husbands can EVER find out! Agreed?"

Jake and Dave both agreed.

Jane again looked at mom, "Come on let's have some fun." Mom reluctantly nodded and smiled.

Both women turned around to face away from the guys. They slowly removed their tops holding them in their hands, hiding their breasts. They smiled at each other as they dropped them to the floor at the same time. Jane was wearing a sexy lacy black bra. While mom just had on a plain white bra.

Jake laughed. "Wow only Jane has a sexy bra on! Guess Sue didn't want to wear anything sexy for us!" Mom shot Jake a dirty look.

Jane just looked at mom as she started to take off her bra. Mom followed but wasn't smiling like she was. They both slowly moved their hands reaching behind them to unsnap their bras.