A Very Fun School Trip Pt. 02

This is based off of a true story, so the names have been altered. I'm still getting used to writing this type of story, so if you have any feedback, please give it :)

This is part of a series about I'm writing, so if you want to have a better understanding of what's going on, I'd recommend reading them in order.

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After having just finished our first round of fun, we both knew we couldn't let this end here. The reason we hadn't had sex was because she wasn't on the pill and I had no condoms on me. We decided that we'd split up for about 15 minutes, try and find a condom, and meet back up in my room at 10:00.

I headed next door to Teddy and Jacobs room, where I was greeted by them both, the smell of weed, and a bunch of guys celebrating the end of our trip with shots. Teddy took one look at the look on my face and shouted "He finally did it!"

There was cheers all around, congratulations from people I had barely talked to, and the one person that wasn't cheering was Tom. It was okay though, because Tom thought he had a chance, and Tom was one of those nice guys that thinks they deserve the girl simply for trying to be nice to her. No one liked Tom. I tried to hush the cheering and stated loudly and clearly my reason for being there.

"Guys, I have a request. Does anyone have a condom I can use because I want to fuck Sammie so bad." I was handed three condoms, and left after doing a couple of celebratory shots with my friends.

When I was walking back to my room I ran into Sammie at the door, who said with some sadness that she hadn't found any. When I told her that I had found some, her face lit up and she basically started jumping up and down with excitement. While I fumbled with the key trying to open the door, Sammie started rubbing my cock through my pants and kissing my neck. We were out of our clothes before we even made it on to the bed, and while I vigorously licked her pussy she wrapped her lips around my dick and started sucking. Not wanting to cum before having sex however, I stopped her from sucking so I could get the condom on. As soon as it was on I started rubbing my 7.5" cock up and down against her pussy to tease her. She started to quiver from excitement, and began to push against my dick as well. I wanted to tease her for a little longer, so I kept roughly rubbing my cock against her clit, so I could hear her beg me to put it in. At last I heard the words I was looking for as she gasped between moans for me to put it in already.

I pushed into her tight pussy and immediately felt enveloped by its warm, tight feeling. I was only in about half way before I started to pull out. She began to complain but I quickly pushed it back in, this time deeper, feeling my thick cock fill her pussy up. Her complaint ended mid sentence and melted into a moan of pleasure. When she felt me start to pull out again she moved herself forward, accidentally making me take my cock all the way out, and when I pushed it back in I buried it all the way up to the hilt. She let out a sharp moan as it went all the way in, and I began to slowly pump my cock in and out of her tight, wet pussy. I started slowly in a missionary position but I started speeding up almost immediately. As I heard her moaning pick up to a faster pace, I flipped us over so I was below her and she was riding my cock. She began to straddle my dick, taking it all the way out before quickly sitting down on it, letting it slide all the way in before repeating the process. I couldn't help but push against her pussy as she pushed down against my dick, making it go deeper and deeper.

Close to cumming for a second time in one night, I decided to push my luck and put one finger on the edge of her asshole and started rubbing. She paused for a moment and looked down at me. I continued to rub her tight, beautiful asshole and she brought her attention back to riding me. I then pushed her back down so her legs and ass were in the air, and her back was on the bed with my dick still in her pussy. I spat on my index finger, pulled my dick out of her pussy, and then pushed my dick into her pussy at the same time as I pushed my finger into her asshole. She moaned so loud I heard the party in the room next door stop momentarily, and we both froze and covered our mouths with our hands. Then, after a few moments of silence, the sounds of the party resumed, and a few seconds later, so did the sex. I started slowly pushing more fingers into her rosy asshole, until I was pushing three fingers in and out of her ass as I filled her pussy with my cock. Then, in one move, I pulled my fingers out of her ass, pulled my dick out of her pussy, and as she moaned that she was cumming, I pushed my dick into her ass and she let out a yelp of pain. I was about half of my shaft length deep in her asshole, which was so tight I was worried my dick might fall off. I started to pull out a little bit, worried that I had overstepped some unspoken boundary, but Sammie reached both of her arms around me and pulled me further into her perfect ass.

Concerned, I said "Hey, uh, I don't know if this is your first time doing anal, but thats a lot of dick to take in your ass at one time and I don't want to hurt you."

She returned my gaze with fiery eyes and said "Will. That was one of the best orgasms of my entire life. I'm not letting that go unreciprocated, and if this is the best way to get you to cum, so be it."

Not being one to argue, as I was in a state of extreme bliss as I felt her tight asshole continue to tighten and relax around my cock, I told her we could continue, as long as she followed my instructions. She nodded silently in agreement.

"First, you have to relax a bit Sammie. It feels great if your asshole is tight, but also my movements are restricted a bit if it's too tight." I felt her asshole relax a little bit, and I started to pull myself out. As my dick left her asshole, I felt her give a sigh of relief. I then began to push against it again, and forced my way through that rosy opening once more and into her ass. I pumped in and out over and over, until I couldn't hold back any longer and came. We both looked over at the clock to check the time. It was only about 1:00 am, and the night was still relatively young. We both knew this couldn't be the way this night of fun ends, and as I threw out the condom Sammie started walking towards the bathroom. I figured she was going to use the toilet, but the second I heard the shower turn on, I knew that we had other things in store.

END OF PART 2