Five Pennsyls
Chapter 1

Copyright© 2016 by RICHARD the THIRD

Sex Story: Chapter 1 - Two parents plus five kids, all college aged. This is what happens when your life evolves around being rich and having lots of money. By the way, Mom and the three daughters are all gorgeous. She was a model before she got married to big money!

Caution: This Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Consensual   Romantic   Lesbian   Heterosexual   Incest   Mother   Son   Brother   Sister   Daughter   Group Sex   Anal Sex   Cream Pie   Double Penetration   Exhibitionism   Masturbation   Oral Sex   Pregnancy   Safe Sex   Tit-Fucking   Voyeurism   Big Breasts  

I am the middle child of five kids:

Peter 23
Polly 22
Paul 21, that’s me
Pamela 20
And Penelope 19

Our last name is pronounced (pen-cils)

Mom and Dad’s explanation for having five children in five years was that mom (Paula) wanted to get her figure back. She was and still is a literal trophy wife. I’d seen pictures of her winning some modeling awards, but the story isn’t really about her.

Dad (Peter Senior) also wanted her to get her figure back and agreed after Penny was born, to have a vasectomy.

He explained it to us as being a birthday present to Paula.

She explained it as not wanting anything to droop and sag and at her current age of 43, nothing was either drooping or sagging on the front or back of the really hot chick that I call Mom.

Dad was the best and thus the highest paid lawyer in Nevada. One of the reasons that all five of us kids had gone to a very well-known University almost 400 miles away in Utah, The University of Utah.

Dad’s great great grandfather came from Finland With the last name of Pennyslasson and over the course of time our last name evolved to become Pennsyls causing my youngest sister to have the most alliterative name of the bunch, Penelope Pennsyls.

Fortunately her middle name was Anne, which was what we all called her nowadays.

Peter was going for his masters in political science. Polly was in the process of getting her second bachelor’s degree in fine arts.

I was halfway through my bachelor’s degree in physical education, while Pam and Anne were loading up with required classes changing their major every other semester.

With dad’s power and influence, we were all in the same off-campus housing in three large apartments all on the same floor.

Why only three?

My older brother Peter had the brilliant idea that he and Polly would share an apartment, then I would get my own and Pam and Penny got one to share.

Why is that so brilliant?

Because we were getting monthly checks from dad all the while he was assuming we were in five separate rooms. We took all the money and split it five ways which is better than I had expected, considering my brother was the one who brought it up.

We took each other’s pictures posting them on Facebook hopefully making both mom and dad happy and keeping them from the unlikely idea of coming to visit us.

We have a plan in place provided they gave us at least a day’s notice with some friends in the same building.

Peter was two semesters away from being done with school with a plan to move to Northern California to go to work for the political arm of Google. That was a done deal that he hadn’t told dad about but he didn’t seem to care.

He didn’t have a girlfriend at least a regular one to drag him down, as he put it.

All three girls and I were working together to get as much school work done as possible when Anne asked me, “Why are you not dating anybody, big brother?”

“Girlfriends are just too much trouble when you’re trying to get good grades,” I responded.

“If you weren’t my brother,” Polly said, “I would date you.”

That got the girls all arguing about which of them would be the best for me if I could date any of them!

“Ladies, that is a ridiculous concept on its Merit! I can’t date any of you because you are my sisters that’s it ... end of discussion, OK?”

Pamela responded to that by walking over to me and asking me to stand up.

Worried about what was just about to happen she said, “Take a picture of us please? Now each of you stand next to him and we will take a picture.”

After that was all done we all looked at the pictures with Pamela saying, “I think Penny looks best with him, don’t you?”

They all disagreed again until Penny had an idea which was both fascinating and very very dangerous.

“I think we should each go on a date with Paul!”

“That’s ridiculous,” I said.

“Why?” My youngest sister said.

“Are you afraid to go on a date with each of us; is there something wrong with us are we not pretty enough for you to date?

That defense was flawed but I will just get them mad in the process so I agreed to it.

“Who would go first?” I asked hoping to start a fight between them,

Polly very quickly said that Anne should go first.

“You have to find a place to take her and come over to our apartment and ask her for yourself just as if you had never met her before,” Polly said.

They all agreed with that and liked that idea.

“And it can’t be a place you have ever been before Paul!” she added.

I want to go on the record and say that this is a very bad idea but I agreed to do it. “Give me a few days, OK?”

“That means that on Thursday you have to come over knock on the door and treat her like she isn’t your sister and ask her on a date that you will take the next evening!”

We all went back to work on our school stuff until Pammy and Penny left my room.

“My dear older sister don’t you see the problems that this could create?” I said to older sister.

“Actually, Paul ... The only problem I see is that just maybe the two of you might be the perfect couple.”

“What the hell are you talking about, the perfect couple?”

“She has told Pam and me in the last two months that she thinks she is in love with you.”

I had no words to respond to that, but Polly did by saying, “Just be yourself ... that’s all she expects.”

She closed her schoolbooks and stopped to give me a peck on the lips and used her favorite expression “Toodles, little brother!”

I wonder just how seriously I should take this whole thing.

The one thing I did do was to masturbate that night thinking about all three of them while imagining it was Polly I was taking on a date:

The first part of my dream was my walking up to the room that she and my older brother shared and knocked on the door. Of course in my dream my brother answered the door so I simply asked if I could speak to Polly privately.

She had walked out wearing a pair of Silk pajamas, simply saying “Yes, can I help you?”

“Pollyanna,” I asked using her complete name, “I had an idea swimming around inside my head and it was to ask you if you would like to go out to dinner with me sometime just the two of us. I don’t get much time alone with my oldest and prettiest sister.”

She agreed and turned to go back inside and I got her on her elbow turning around and giving her a very soft and tender kiss on the lips!

“Hmmm, that was nice little brother – how about tomorrow for the dinner date?”

“That would be fabulous,” I said, adding, “Wear something that shows off your fabulous figure why don’t you?”

She took the single step she needed for us to bring us chest to chest and lip to lip. She is rather built, almost as much as our mother.

I made the move with my lips and my arms and we had a very romantic kiss between the two of us and then our lips opened and it just became very romantic and very erotic...

And then I came in my pajamas!!!

Since I felt that I deserved it I turned over on my side and went back to sleep.

I was doing well enough in all my classes that I decided to blow the day off, so I got up took a nice cold shower and changed into some nice clothes.

I took a walk to Pam and Anne’s and knocked on the door.

Pam opened having obviously just crawled out of bed and said very mean spiritedly, “What the fuck do you want?”

“May I speak to Anne please -- I’ll wait.”

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