It was that time of the year again: the end of the year orchestra trip. This year, they were headed up to Boston for the music festival (that’s what they call the competitions). It was my senior year, and he knew it had to be the best one of all.
The trip up was going to be around 14 hours, so they were leaving at night on Thursday. The orchestra had rented a double decker bus where the instruments and equipment would go on the bottom floor with the chaperones, and the students would sit up top. Luckily, seniors had first choice in seating, so my friends, Jack, Shelby, Valarie, and Mark, all chose seats in the back. As everyone who’s ever gone on a school trip knows, the bus ride is really one of the best parts, as long as you get the right seats.
Once the bus was packed, everyone started boarding, and very soon we were underway. Even though it was already late, everyone was so excited for the trip that they stayed up for the first few hours, playing games or listening to music or just chatting with their friends. My friends and I had started getting really nostalgic and were looking back at all their memories from past orchestra trips.
Then Shelby brought up a memory they had all been a part of from our freshman year. That year, we’d gone to Disneyworld. It was our last day in the park, and we had found a cave on the island in the middle of the magic kingdom (man made cave for anyone who doesn’t know what I’m talking about). We were hiding in the cave to avoid another kid who annoyed us a lot. While hiding in there, we were all talking, and when some of the other guests had passed by the section we were in, Shelby, who was always known by everyone to be a huge slut, seemingly out of nowhere admitted that it was one of her dreams to get gangbanged in Disneyworld. Needless to say, our jaws dropped, and our cocks got hard. Of course, nothing happened. We were all young and most of us weren’t too attracted to Shelby (at least we didn’t admit it).
About Shelby: she has medium length dirty blonde hair and big brown eyes. She’s short, at around 5’ even, and fat. But not in a gross kind of way. She has huge tits that looked like they would probably sag when bare, but she loved showing them off, constantly wearing low cut tops or tank tops. Earlier that year, at her birthday party, she’d even let us toss little things at her to try and get them in between her tits. She had a fat stomach, but I thought it was perfect on her, as well as a fat ass, but again, not ugly fat. Whether she actually slept around a lot or not, none of us knew for sure at that time, but she always talked like she did.
Back to the present on the way up to Boston. We were still talking about that time, when Jack asked what she would’ve said if any of us had said that they should. She took a minute to think it over before saying that she probably wouldn’t have… maybe.
She’d hesitated. We’d all seen it, even Valarie, who hadn’t been there for the original event, so she only had a limited idea of what we were all talking about.
A couple seconds passed, and I thought someone was going to change the topic, but then Valarie surprised us all and said that she thought the idea of getting gangbanged anywhere sounded really hot. God, what a shocker that was.
About Valarie: she is, without a doubt, the shyest girl I’d ever met before then. We were all close and hung out all the time, but she was the friend in the group that listened and took things in more than contributed. Not to say she was boring. When she did talk, it was usually something really funny or cool, but it just wasn’t often. She was pretty tall, almost as tall as Jack, who was and she had a very slim body; a flat stomach and small, round tits. She had light brown hair, and an olive skin tone.
Now we were stuck on the topic, although us guys were hesitant to say anything, thinking Shelby and Valarie would be offended in some way. So we listened to what they said, about how many guys they think would be the perfect amount, and the positions they would get in and, as girls must, which celebrities they would want to have involved.
Finally, the topic changed and we went on with how it had been. Eventually everyone got tired and went to sleep. When we woke up, it was morning and we were almost to the hotel we’d be staying at for the next two nights.
The sleeping arrangements were four to a room, so Jack, Mark, another senior named Nick, and myself were all in one room, and Shelby, Valarie, and two younger girls were in the room across the hall from us. The chaperones informed us that after 10pm, if you wanted to hang out with people from other rooms, it had to be in a public space.
Skip forward to the last night of the trip
The last night of the trip is the night where they do the awards for all the different schools. They have a dinner before the awards ceremony, and then a dance to end the night. This year, the whole thing took place in the hotel we were staying at.
We all got ready in suits and ties and whatnot and headed down to meet with everyone else before heading in. When we got down to the lobby, we found Shelby and Valarie. Shelby was wearing a short blue dress that was slightly low cut, and her hair was done up nicely. Valarie had her usual straight hair, and a short black dress that seemed like it hardly went below her ass. And speaking of her ass, we noticed something none of us had ever noticed before. Valarie had the most perfect ass ever. We all knew she had long shapely legs, but none of us had ever really paid too much attention to her ass. God, what a sight.
So we went in to where the event was taking place and found an empty table for all of us to sit at. We ate and had the award ceremony, which we did pretty well in, and then the dance started. The girls ran off before us, and we stayed behind and all of us simultaneously brought up Valarie’s perfect ass. We decided that the goal for the night was for all of us to dance with her before the night was over.
We made our way onto the dancefloor, being all smooth and not going straight for the kill. Jack went first. He came up next to her and put his hand on her lower back, and it was like she knew exactly what he wanted. She turned and immediately started grinding on him. We were shocked that it had been so easy.
I, not wanting to dance by myself while waiting, went over to Shelby who was all too willing to grind. And it felt great. I started with my hands on her hips, but as the song went on, I inched them farther and farther forward, bringing them around and down as much as she would let me. I was finally stopped right above her pussy. I could feel the edge of her underwear through the fabric of her dress. Finally, when the song ended, she turned around and I took the opportunity to really see how her ass felt. I grabbed her cheeks and lifted her up on her toes, and found that she was wearing a thong in the process.
Then it was my turn with Valarie, and again I slowly inched my hands forward to see where she’d let me go, but instead of going around towards her pussy, I moved my hands around to the front and then down her legs so that my hands were half on her dress and half on her legs. Still not getting any signs to stop, I started lifting her dress a little and moved my hands in between her legs. Finally I decided to go all the way and placed one hand on her underwear and to my surprise, I found it was soaking wet. So I started rubbing back and forth as the song went on, feeling my hand getting even more wet.
After another few songs, we had all danced with Valarie and had gotten to feel how amazing her ass was. But there was still a lot of time left for the dance. All of us went and sat at our table for a break, and Valarie and Shelby started whispering to each other. Then, they both stood up and told us they were heading back up to their room, and that we should come up once we’re done dancing.
Although we were confused, we ended up leaving after another couple songs. The three of us got changed into basketball shorts and t shirts and went to knock on the girl’s door. Shelby answered, but we all just stood there. It looked like she’d just gotten out of the shower. All she had on was a towel wrapped just above her breasts. After a couple seconds, she snapped her fingers and we all came in and sat on the couch or in a chair. Shelby walked back over to her bag and without any warning to look away or anything, she dropped her towel and started picking out things to put on. Our jaws dropped, and none of knew what to do. She turned around and asked if we were OK, but none of us know how to respond. She turned back around and bent over to grab something, and I decided there was no harm in trying.
So I walked up behind her and grabbed her big sagging tits. She stood up and yelled, “Finally one of you gets the idea!”
All of us were still confused, but before we could ask any questions, she turned around and told us all to strip. We did, and as before I could even get my feet out of my short, Shelby had gotten on her knees and was stroking my cock. The others were now all standing around, and Shelby started sucking my cock while signaling the others to come closer so she could stroke the others.
Then Valarie walked in from the other room, also in a towel. She’d just gotten out of the shower and she looked kind of mad. It turned out it was because she was mad that Shelby had started before she had gotten out.
Valarie dropped her towel and pulled Mark and Jack over to her and started sucking on Mark’s cock while stroking Jack’s.
After a couple minutes of one of the best blowjobs I have had, even since then, I pulled back and got Shelby to stand up and started making out with her while rubbing her big tits. Then I started rubbing her pussy, which was already soaking wet. I broke off the kiss and moved her over to one of the beds and pushed her down on her back by the edge and spread her legs as far as they could go and started eating her out. She was so sensitive that she let out a little bit of a squeal. I kept going until she grabbed the back of my head and pulled me away, but not before I gave her one of the best orgasms she’d ever had.
Meanwhile, Valarie had taken Mark and Jack over to the other bed and had Jack lying down on the bed where she was now sucking his cock with Mark standing behind her eating her out.
I pulled Shelby closer to the edge of the bed now, and she grabbed my cock, stroking it while lining it up with her pussy. She started rubbing my cock up and down across her clit, but before it could go any farther, I asked if I needed to use a condom. She responded with a sexy smile and commanded me to fuck her pussy. I took it as a no and dove right in. And god, what a tight pussy that was. Already I knew I wouldn’t last too long. I kept taking long strokes as she rubbed her clit.
After a couple minutes, I felt like I was ready to cum, and she pushed me away and told me to lie down on the bed. She got on top of me, and squatted with her pussy right over my cock. She lowered herself down so that only the tip was inside, and then impaled herself on my cock. She took charge and fucked me harder and faster than I ever thought a girl like her could and it felt amazing. Again, I felt that I was going to cum soon, but she stood up and got off the bed. I looked over, confused, and saw that Valarie was coming over, with cum dripping off of her perky nipples. I stood up beside the bed and started making out with her, grabbing her amazing ass. After a few minutes, I bent her over next to the bed and lined my cock up with her pussy, but then I noticed how perfect her asshole looked and decided to switch things up. I rubbed her pussy lips with my cock, and then kept going up, rubbing her asshole as I went up. I started going back down and stopped at her asshole. I waited for a response, and she turned her head around and just said, “What are you waiting for?” That was all I needed. I pushed slowly into her ass until my cock was completely buried in her tight ass.
As I fucked, I looked over and saw that Shelby was being spit roasted with Mark fucking her pussy and Jack with his hands on the side of her head, face fucking her with no signs of stopping or slowing down. Eventually, Mark and Jack had finished, and Shelby had cum dripping out of her pussy and down from her mouth. They all came over to Valarie and I and Shelby started making out with Valarie while I kept fucking her ass. Then Shelby came around to me, pressing her breasts up against my arm and Mark moved in front of Valarie, stroking his cock as he started to get hard again. Once he was good to go, he made Valarie open her mouth and started with slow thrusts, gradually getting faster until he was full on fucking her throat.
I could feel myself getting close to cumming, so I picked up the pace and I could hear Valarie moaning more and more. But just before I could cum, Shelby pushed me back and my cock popped out of Valarie’s asshole, leaving her slightly gaping for a moment. I looked at Shelby, confused, but she just brought me over to the bed and laid me down before straddling me. She told Jack and Mark to join us. She wanted to take all three of us now. So Jack stood by her head and Mark crouched behind her, stroking his cock right by Shelby’s asshole. She grabbed Jack’s cock and started sucking on it while also starting to ride up and down on my cock. After a minute, she stopped with my cock buried inside her and Mark shoved his cock all the way into her asshole, making her moan in pleasure. We started fucking again and after a little more, Valarie got on the bed and was standing with her legs on either side of my head. She looked down and winked before dropping down to bury my face in her wet pussy.
The five of us kept going and before I knew it, Valarie was orgasming, her legs shaking with each convulsion. But I kept licking and sucking making her scream. At the same time, Mark and Jack were nearing their limit. Jack grabbed Shelby’s head and took control, ramming his cock as far back as it could go until he was about to cum. Then he pulled out and shot his load all over Shelby’s face. Mark was the next to finish. With his last stroke, he pulled out and shot his load all over Shelby’s ass which also caused Shelby to have an orgasm from her ass. Finally it was just me, Shelby, and Valarie. Shelby kept riding up and down as I licked Valarie’s pussy. After another few minutes, I knew there was no holding back. I started lifting my hips and fucking back until all three of us orgasmed at the same time. I grabbed Shelby’s hips and pulled her down on my cock, burying it deep in her pussy. Valarie collapsed forward, and Shelby had to keep herself steady so that she wouldn’t fall over too.
Slowly my cock softened and slipped out of Shelby’s pussy. She got off and Valarie had moved over and the three of us laid on the bed catching our breath while Jack and Mark started getting dressed. Unfortunately, we didn’t have much time to rest, because the chaperones would probably start looking for us soon. We all got dressed and headed back to our own room, but before I left, I went over to Shelby and kissed her, grabbing her tits and making her moan one more time. Then I went over to Valarie and grabbed her ass and spread her cheeks apart while kissing her. Before I let go, I gave her ass one last squeeze.
The rest of the trip went by pretty quickly. We all sat together on the way back talking about how much fun touring Boston had been and whatnot, but we all knew that that wouldn’t be the only time we fucked. From that point on, we were all even closer than ever.
story by: luckyman95
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