This is another true story that took place in the spring semester of my senior year of high school. The names are changed, but everything else is what really happened.
Matt: white, average build, 5’8”, medium length brown hair, 6.5”
Cayla: white, atheletic, 5’8”, long light brown hair, 32C
It was the last night of the orchestra trip up to Boston, which meant it was time for the dinner/award ceremony/dance, and everyone was really excited, because we knew we had done really well this year. Everyone was cleaning themselves up and getting ready for the night, which started around 6:30.
Since we were staying in the hotel that the ceremony was being held, we all headed down together around 6:15 to make sure everyone was dressed nicely and ready for the night. When Cayla came down, me and a bunch of my guy friends all knew that we had to dance with her. She was wearing a short, tight black dress, and we could tell when she turned away from us that all she was wearing underneath was a thong. Not only that, but when she started walking, we all saw how amazing her ass was. At that moment, there was no longer any doubt that she was the sexiest, most beautiful girl in the orchestra.
All the seniors sat at one table and were all making jokes and having a great time. They had two options for dinner: some sort of fancy chicken with potatoes and an assortment of vegetables, or the same thing with steak instead of chicken. This made us all look at Cayla, who we all knew was a vegan and had already been having an awful time on this trip when it came to food.
After dinner, they started the awards, and we placed first in our division, and a few individual students won some awards as well. We all cheered the loudest of all the schools and were so proud of ourselves at how amazing we had done.
Finally, it was time for the dance. At first, the floor stayed somewhat empty, since none of the schools knew each other, not to mention that two of the schools were all male Christian schools. After a while, everyone started to mingle, though most of the kids in my school still stuck together in the middle of the dancefloor, having an awesome time. Some of the guys started grinding together, making the Christian schools feel really awkward. Eventually, most of the schools left, and it was mainly kids from my school left. I saw Cayla, who had always been a really shy girl, dancing next to a few of her girl friends by the edge of the group, and I decided to go over and dance with her. I grabbed her waist and started grinding with her. She gladly went along with it, happy to not be dancing alone anymore. We kept going for a few songs, my cock getting rock hard as I watched her perfectly big and round ass grind on it. For most of the songs, she was bent over, and really getting into it, but during one song, she came up and grabbed my hands, and really surprised me.
When she grabbed my hands, she started to move them closer and closer to her pussy and, since we had moved in to the middle of a large group, she gently pushed my hands up against it. She was so wet, I could feel it through her dress, which just turned me on even more than before. At the end of the song, she turned around and let me squeeze her ass and whispered in my ear to meet her outside the ballroom. And, with a sexy smile and a wink, she grabbed her things from the table and left the room. After another song, I told my friends I was going to head up for the night, and grabbed my jacket and headed out. I left the room, and as soon as I turned the corner toward the elevators, Cayla grabbed me and pulled me in for a kiss. I broke the kiss to press the elevator button, and as soon as it got there, I pushed her into the corner, lifting her up as she wrapped her legs around me, and we continued to make out, all the way to the top floor.
When we got to the top, we ran down to my room and locked the door behind us. Immediately, Cayla started unbuttoning my shirt as we continued our passionate kiss. Eventually, I was left in just my underwear, which at that point had a huge bulge in it. Cayla started to rub it as I pulled her close and brought her dress up just above her ass. That ass was so amazing, I just couldn’t let go as I continued to squeeze and slap it. The fact that she was wearing a sexy little black thong made it even more amazing, with nothing in the way of my hands. Eventually, I broke the kiss and pulled her dress off over her head, leaving her amazing perky breasts and flat stomach naked for me to admire. Immediately, I grabbed her tits and started sucking on her nipples, making them as hard as they could get and making her moan louder and louder.
After a few minutes of switching between her amazing breasts and making out, she broke the kiss and pulled off my underwear, grabbing my hard cock and leading me over to my bed. There, she got on her hands and knees with her ass high in the air, to let me strip her of her tiny black thong. As I slowly pulled them off, I couldn’t help but stare at her beautiful ass and at how wet her shaved virgin pussy was. I spread her legs wide and got down to eat her out. The touch and motion of my tongue elicited loud moans of pleasure from Cayla, which just turned me on even more. In no time, she was about to have her first orgasm, but I stopped short and stood up, pulling her up and bringing her over to the open window. There, I pushed her firm tits up against the glass and spread her legs apart, with her ass facing out, ready for me to take her virginity. Slowly, I teased her with my cock, pushing it in until I met resistance, and then pulling it back out, until she was begging me to give it all to her. Happily, I obliged, and with one quick thrust, I rammed every inch of my hard cock up inside her tight pussy, making her scream from the shock and pleasure of the moment. Without skipping a beat, I continued to pound her newly deflowered pussy. With each thrust of my cock, she moaned and screamed, quickly building up until one last thrust sent her over the edge. The walls of her pussy tightened around my cock, sending me over the edge at the same time. Simultaneously, I came deep inside her as her orgasm shook her body, each wave causing her to tighten further on my cock, milking it of every last drop of cum. We stood there for a few minutes, panting and catching our breath. Finally, I pulled my now flaccid cock out of her, causing some of my cum to pour out of her into a puddle on the ground. We went over to the bed and kissed for another few minutes, until she realized that the dance was almost over. She quickly started to slip her dress back on while I admired her ass one more time, moving over to grab a handful before she kissed me one more time and headed to the door. Right as she was about to leave, she bent over, pulling off her little black thong, which she threw to me with a wink. I picked them up and knew I would be seeing her again very soon. She left and I went for a shower and waited for my roommates to get back so I could brag about how awesome my night was to them. They didn’t believe me at all until I pulled out her thong and showed it to them, proving what had happened.
The next morning, we packed our things onto the bus and headed back home. Cayla came back to sit with me again, holding a blanket and wearing her pajamas. She told me she was really cold and wanted to sit with me on the way back. She took her seat and pulled the blanket over the both of us. Then, she grabbed my hand under the blanket and moved it to the waist of her pants, letting me slide it down where I found she wasn’t wearing any panties. She gave me another wink while our friends were all preoccupied, and I knew she was telling me to do whatever I wanted. So, I started rubbing her pussy, and eventually started to finger her under the blanket as our friends talked amongst themselves and to us. None of the girls had any idea what we were doing, while all of my roommates looked at me with a knowing smile. She orgasmed quite a few times on the way down, and that night, when everyone else on the bus had gone asleep, she pulled the blanket down and gave me one of the best blowjobs of my life, swallowing every single drop of cum.
When we finally got home, she told me to call her sometime and gave me one final wink. I knew exactly what that meant, and I knew that the rest of my senior year was going to be a lot more fun.