Jess’ First Slumber Party

Looking back at my years in high school there was really only one event that stands out to me as a good story. I was sixteen and my best friend Kaitlin invited me over for a sleepover. She was my best friend since grade school but I’ve never been able to sleep over at her house until that night. My mother was pretty anal growing up and it took me a while to convince her she could trust me. I feel stupid about it now, but prior to going to her house I called Kaitlin up and asked her what I was supposed to bring to wear. I had no clue whether or not you were supposed to wear pajamas.

“Jess, you’re so awkward”, was the response I was given.

Apparently you do. I tried on the pajamas I planned on wearing that night. I looked into the mirror, the tank top I had chosen was a little too flashy but my breasts weren’t all that big at the time and it was just going to be girls there. My bottoms were pink and showed off the cute little butt I used to have. I smiled at myself in the mirror. I have a cute smile that I think got me a lot of boyfriends later on in my life. I also had smooth brown hair back then that went down to my shoulders.

I got in the very backseat of our van with my bag. The thought came to me that I wouldn’t be able to masturbate that night. I had just learned how to masturbate that year and I had been doing it at least once a day. My mom wouldn’t be able to see my lap since I had a whole row of seats in front of me so I got a crazy idea. I stuck my hand inside my pants and started to touch myself. It felt good at first, but as I realized we’d be at Kaitlin’s house soon I needed to do more to make sure I got off in time. I lowered my pants and panties just a bit so my crotch would be exposed to the air. I really started getting into it then. My mom was talking to me about being respectful and asking me questions about what I would do in case of emergencies. I was able to answer them at first but as I got closer to my orgasm I wasn’t able to concentrate as much. Every time I had to respond to her I had to make sure she couldn’t hear the lust in my voice. We turned onto the street Kaitlin lived on; I was running out of time. I took a risk and slipped my other hand under my shirt and gave my breast a squeeze. That did it, I started moaning quietly and I came right as we pulled up. I swiftly took my hand out of my pussy, sucked my juices off and pulled my pants and panties up. I got out of the car and my mom left in a hurry to make it to some book club on time. I knocked on the door and Sarah answered. Sarah was Kaitlin’s cousin, they were both a few months older then I was. She was wearing short shorts and a tank top. I couldn’t help but notice her breasts because they looked like they were ready to pop out of her shirt. She caught me staring and laughed at me.

“You haven’t seen me in a while huh?” she said.

“No, guess I haven’t”

She led me to the T.V room where Kaitlin was sitting on the couch. She had pig tails that day that made her look a lot younger. That and her breasts were the smallest out of all of us. She had a bright green shirt on that really stood out because they matched her eyes beautifully. I don’t think she had even started wearing a training bra yet because her nipples were slightly noticeable.

“Where’s your mom?” I asked.

“Out of town”, she said. “What you didn’t know?”

I didn’t know, to be honest, nor did I care. I’ve been kept under so much constraint from my mom throughout my teenage years and I loved the freedom.

“So Kaitlin, what’s the plan?” Sarah asked.
My heart skipped a beat. Apparently Kaitlin had invited some boys over as well. I got hella nervous to say the least; I hadn’t had a boyfriend then and always got shy around boys. Luckily it was boys I didn’t know. They were Kaitlin’s neighbors, Tim and Jake, and they didn’t go to our school. Jake was 18 and Tim was 16, Kaitlin told us they were both pretty cute.

We sat around and watched TV until they arrived. My mind was going crazy thinking about what could possibly happen in the next few hours. It was nine o’clock when the doorbell rang. I answered the door and was greeted by two handsome boys. Tim had short blonde hair and some freckles, he looked a little shorter then I was. Jake on the other hand was at least 6 inches taller and was gorgeous. He had black hair that was just a little shorter than mine and pretty big muscles. He gave me a sexy smile and I couldn’t help but blush. I let them in and Kaitlin came and greeted them. We all gathered and went to Kaitlin’s room shortly after their arrival.

After making fun of the boys for a little bit we all started to get a bit flustered. Kaitlin suggested we play a game, since we all seemed kind of new at this Sarah suggested we should each take turns and choose someone whose clothes we wanted to take off. I probably wouldn’t have wanted to do anything this crazy any other day but I had gotten wet since we all sat down and started talking. I looked around and the only person who seemed more embarrassed about this then me was Tim.