Jen: A Beauty to a Beast

Here are a few stories about another girl who confused the hell out of me. Her name is Jen.

I've known Jen since she was probably fifteen years old or so. My family was already friends with Jen's family but it wasn't until my oldest brother married Jen's Mom that Jen and I began hanging out.

Jen and my oldest niece would often hang out together and since they were closer to my age I'd always want to hang out to them. I was older then Jen so I never tried doing anything with her as much as I wanted to until she became of age.

To give a description: Jen was really cute when I first met her. She was fairly short, maybe 5'2 or so, and weight no more then 115lbs. She had dirty blonde hair and a great body. One thing I really liked about her is the fact that she was kind of ditzy and air headed.

I knew Jen looked innocent but didn't think she really was.

One night, Jen and I got bored and decided to take a walk around our home town. As we walked her and I told stories and made each other laugh and we even held hands as if we were a couple.

Eventually, the topic turned to sex. It was that night that she freely admitted what her sexual pleasures were and even told me that she shaves her Pussy. I knew that Jen had a few boyfriends but wasn't quite sure if she fucked any of them or not.

I asked her if she liked cum. Her response was that she hasn't really experienced too much of it in order to really take a liking to it. I asked her where she's ever had it and what she said shocked the hell out of me.

"I've had it in me." She said.

What shocked me even more was when she told me the name of the guy who almost knocked her up.

I knew the guy and really didn't like him. He was a literal dirty, stinking, rude bastard and I couldn't think of what Jen saw in him. I asked her if she's ever had cum on her face or in her mouth and she told me that she had never done anything like that. I told her that I'd really like to do that to her if she'd ever want me to.

Suddenly, a huge summer rain storm unleashed and our walk was cut short. Jen and I ran full speed to her house where we hugged each other good night before I made my way home a few more blocks over.

The next morning, I had just woken up when I heard a knock on the front door. I opened my bedroom window and called to who ever it was.

Turns out, it was none other then Jen standing outside.

"Do you want to go for another walk?" Jen asked.

"Yeah, let me take a quick shower and I'll be down." I told her.

Ten of fifteen minutes later, I went downstairs and opened the door and went outside.

It was then that I noticed that Jen was wearing a very tight pair of denim shorts and a yellow and black flower pattern bikini top that was probably two or three sizes too small for her rather large tits. Each one of them looked like cannon balls.

Jen and I began to walk, We decided to take a walk along the foot path that ran alongside the canal that snaked it's way through the middle of our home town. Like the night before, the two of us told stories and laughed.

When we reached the halfway point between the park at the head of the foot path and the highway at the end our conversation dropped off and it fell silent for a couple of awkward minutes when Jen asked me something I think I will always remember.

"Do you still want to cum on me?" she asks.

I swear if I was drinking something right then, it would have resulted in a spit take.

"Yeah, if you want me to yeah, I wouldn't mind that at all" I said. "I even know a place where we can go."

There was a clearing in the woods no more then two hundred more feet down the path which would have been a good spot for us to mess around.

Jen looked nervous so I just waited for her to make a move. I even ended up telling her that we wouldn't even have to have sex and she didn't even have to suck me off or anything, as much as I would have liked that.

We continued walking and when we reached the clearing in the woods I pointed it out to Jen.

"See, we can go in there if you want."

Now, I don't know if I was pressing her into it, or if she was just too nervous, but to my dismay, she chickened out.

We just kept walking and went back to my house where we just hung out there for the rest of the day.

This next story is kind of fucked up because of the circumstances leading up to it.

Jen accompanied me, my oldest Niece, my oldest brother and my Dad to the cemetery where my Mom is buried to visit her grave not long after she passed away.

We only stayed at the cemetery for about ten or fifteen minutes when we all piled back into my Dad's van. On the way home, Jen noticed that I was a bit teary eyed and she laid her head on my left shoulder and I swung my arm around her.

A minute later, I noticed that my hand was actually cupping her left tit perfectly and my middle finger was right over her seemingly erect nipple. I felt that and lightly, but firmly began brushing my finger back and forth across it.

I'm not sure to this day if Jen felt that or not, but if she did she never said anything about it.

Here is another confusing story about Jen.

Jen called me up and asked me if I wanted to go get a late night bite to eat. We started driving to the all night breakfast restaurant when we saw our friend Craig walking and we picked him up to go out to eat with us.

When the three of us got to the restaurant we ordered our meals and sat and talked while we waited. Craig excused himself to the restroom leaving Jen and I to chat at the table.

I was talking to Jen looking her dead in the eye when suddenly I felt one of her feet come up and it rubs lightly back and forth on the shaft of my cock a few times. Right in the middle of a sentence I let out a high pitched excited squeal.

It startled the other patrons around us enough that they all stopped talking and looked at our table. Jen just sat there with a teasing smile on her face.

I swear Jen wanted me, but why I never done anything with her. I'm kind of glad though because Jen went from looking like a slightly less attractive clone of Britney Spears to looking like Honey Boo Boo's mom. She got fat and ugly.

Dodged a good one there I guess.