I want to give thanks to Starkraven for editing and helping me with this story
Every year as I was growing up, our family would take a trip up to our cabin.
This year Dad invited his buddy (Bob) and Bob's family from across the street to go with us. Dad had finely saved up enough vacation time to take four weeks off this summer. He wanted to head up there as soon as his vacation started so that he could enjoy the great outdoors.
As luck would have it his friend Bob was also able to get his four weeks of vacation at the same time as my Dads. Mom was trying to time her vacation with Dad's also. Unfortunately her stern boss would only let her take a weeks' vacation this year because he said he depended on her too much at the office to have her gone for that long.
Mom knew this was a lie, and it upset her that her Boss was being such a scrooge. My parents talked it over with Bob and Pam (Bob's wife) and not seeing a better alternative, they decided the majority of the family would head up as soon as possible. Mom and Pam would make their way up to the cabin together once Mom's vacation started.
Meanwhile, I was quitting my job so I could go back to college. I really loved going up to the cabin, and this might be my last year to make it happen for quite a while. I figured I would have about a week to go up there around the same time Mom was able to take her vacation.
So, talking it over with my parents, we decided that it would probably be easiest for me to ride up with Mom and Pam when they started their vacations later. I must say, I liked that idea! The thought of just the three of us riding all the way to the cabin by ourselves was exciting. Pam had always been hot, and my Mom was a looker too, even if she was my Mom.
There had been more than one sexual fantasy involving both Pam and my Mom throughout my teens as I lay in bed masturbating and wishing I had something more than my hand to satisfy my adolescent desires. Dad and Bob had already taken the four younger kids with them and had headed up to the cabin. I was eagerly awaiting my vacation time, when my Boss decided to give me an early leave as he could see how distracted I was about the upcoming trip and the start of my college career.
He remembered going off to college and was willing to let me take off a week early so I could enjoy what was left of my summer. When I informed Mom about this she decided to do her best to convince her boss for just one more week of vacation, seeing as she was the only one keeping everyone else from starting out a little earlier.
When she got home from work, she smiled big and gave a little jump in her business suit. Explaining, she said her boss must have been in a good mood because he decided to relent and give her one more week off. Excitedly, she then got hold of Pam to inform her of the good news, and Pam said that the change in schedule would be no problem with her work, and she would be ready to go when Mom and I were ready.
Over hearing the conversation on the phone, I heard Mom and Pam planning to surprise their husbands, by deciding not to let them know they were headed up to the cabin a week early. Excitedly, my Mom hung up and began to pack to and get ready to leave on Friday night after both she and Pam got off work.
My name is Bill and as you could probably tell, I am 18 and getting ready to head to college.
I'm about five feet nine inches tall, and skinny as a tooth pick. In fact, my friends had nick named me super tooth pick because I'm so skinny. As I said, I have always looked forward to going to the family cabin as I love the outdoors and taking in what nature has to offer.
This is the incredulous story of my last trip with my Mom and Pam that started me down a sexual road that I would not trade for all the money in the world.
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Feeling my phone vibrate in my pocket, I dug it out and looked at the screen. It was Mom. Hitting the button, I put it to my ear, "Hey, Mom"
Briskly she said, "Bill I'm going to try and get off work early today so we can get started. Pam said she would be home by 3 P.M. Make sure you're packed and ready to go."
"Sure thing, Mom," I replied, pushing the end button as I headed for my room to get ready for the trip. I couldn't wait for the trip to start knowing I would be in the back seat and able to ogle the two MILFs that would be sitting in the front seat of our SUV.
Daydreaming about Pam and Mom, I started packing, and before I knew it, it was already 2:30 P.M. and Mom was walking through the front door. "I don't have time to change as I want to get on the road as quickly as possible with such a long drive.
We'll get a room on the road if we get tired," she hollered as she quickly went past my room to get her own belongings from her room where she had piled her belongings previously.
Stepping out into the hallway from my room and looking towards my Moms room. I hollered back, "Ok, Mom. Where is Pam?"
"She is on her way home now. She is not going to have time to change either." I could hear Mom's voice coming from her room and a shuffling as she grabbed her things.
I was laughing, "Wow, I'm going to be under dressed with you two."
They both work in management and have to dress to impress every day. Here I was in jeans and a T shirt. I wasn't complaining though because I love the way my Mom looks in her work clothes. She always wears dresses or skirts to work, with low cut tops which tend to show a lot of her ample cleavage.
Both she and Pam are about the same height, around 5 foot five inches or so. Pam's nylon covered legs are the sexiest legs I have ever seen, but Mom has a better figure. Pam has shoulder length brown hair, and my Mom's is red with a little more length.
Both MILFS still have trim fit bodies and can turn heads when they want too. I can't help but stare at either of them when they are in their work clothes. Something about business attire and high heels gets me horny. Thank goodness they don't know what my thoughts are or that they have never caught me watching them with those lust filled ideas.
"Well, don't worry; we're just going to be in the car unless we stop to eat or something."
Mom had on a red pull over blouse which showed some of her cleavage as always and a brown skirt which came down to her knees. She also had on her favorite red heels today and was wearing my favorite black nylons.
Looking out my bedroom window, I saw Pam just pulling into her drive across the street and running into her house. Soon, she came back out with her luggage in tow. She had on a white blouse and black skirt. Her three inch heels accentuated her buttocks as she scurried toward our driveway. I always thought that they were both sexy women in their work clothes, and today was not any different.
Heading down stairs I helped Mom and Pam load their luggage into the SUV. Clambering into the back seat, I pulled out my phone and began passing the time playing on one of my apps, while Pam and my Mom chatted in the front seat.
Every once in a while I would look into the front where they were sitting. Trying to be discreet, I caught glimpses of their legs as both of their skirts had ridden up as they continued to get as comfortable as possible during the trip. My horny mind raced and the situation was making my cock hard. Reluctantly, I got back into my game to make sure they didn't catch me looking.
About two hours down the road Mom said, "I'm getting hungry and I think we'll get off here at this next exit to eat." Explaining, she added, "Your Dad will never stop here and I always wanted to eat at this "Home Style Country" restaurant. It looks like it would have good food."
Sighing, I said, "Mom, Dad never stops here because there is no entrance ramp back onto the highway."
Pam turned her head to look back at me. "Well there may not be an on ramp here but the locals must be able to get back on somewhere. We might have to drive a little ways down the back roads to get back on, but what the heck; we don't have a time table to keep. They aren't expecting us at the cabin today or for a week yet."
Taking the off ramp, we got off the highway and pulled up in front of the restaurant. I purposely stayed behind the two women as we walked in, and I noticed that there were not many people in the place. At one table were four young men that looked to be in their 20's. Three other tables seemed to be occupied by small local families.
One of the four young men at the first table saw Mom and Pam he made a noise that sounded a little weird to me. Looking around, I noticed that all the men in the restaurant now had their heads turned and were checking out Mom and Pam in their polished work clothes and sexy heels. I don't think they even saw me with them.
One of the servers met us at the door and seated us at a table close to the four young men. As we sat down I noticed a game room and after we ordered our food I told my Mom that I was going to check out the games until our food got there. Getting up, I headed toward the game room.
Smiling Mom said. "Okay."
As I walked into the room I noticed all they had was old pinball machines. Something I never played much but I picked one that looked interesting just to pass the time.
While I was playing one of the guys from the table next to ours came up to me and asked leeringly, "Hey, aren't you a little young to be dating them women?"
Laughing, "No that's my Mom and our neighbor."
"Which one is your mom?"
"The red head is."
"Cool. I don't mean to be forward but would you like to play a practical joke on them?"
"What do you mean?" I cautiously asked.
"There's not much to do around here and when we get someone in here from out of town we always ask one of the group if they want to play a joke on the others. Sometimes they say yes and sometimes they say no," he explained mysteriously.
"So how does it work? We're not going to be here long as we're just going to eat and then head back to the highway."
"Well you don't have to worry about that. If you say yes, then we will go from there. Before you answer though, I have one more question for you."
"What's the question"
"Have you ever seen their tits and if not would you like to see them?"
A little surprised, I hesitantly replied, "Well, that's a little forward but I will answer your question. No, I have never seen their boobs but have seen them in their swim suits." Then looking at him with curiosity I continued "Yes, I would like to see those boobs, but I don't think they would fall for a joke to show them to you or me. They are both pretty intelligent women."
He was laughing now "You watch them shows on TV where they punk people into doing crazy things. Well that is kind of what we will do. Trust me, it is all in fun, and there is no harm in a little titty show, right?" He spread his hands and smiled disarmingly.
"Let me think about it. I'll let you know." I cautiously replied.
