A to Z Fuckstories - C is for Cassidy

Sorry for the wait! I slept like a baby that night. A baby that had been sucked dry, that is. I woke up, hoping it was Saturday. However, It was only Thursday. I had another two days before the weekend, and that gave Alex, Jenna, and her s****rs two more days to remove all the sperm from my balls before what I assumed would be a very painful weekend. I took a quick shower and ran my hand through my buzz cut before dressing and driving off to school. Somewhat to my relief, Alex did not enter my car this morning. School went as usual. Jenna said hi, Alex winked. And now another girl in my class, Catherine, was acting strange. She usually nodded or something, but today she was avoiding eye-contact completely. I shot a quick text off to Alex before class. “Did you tell catherine?” Of course, halfway through first period, I got a response. Thankfully my teacher is blind, so I was able to read the “hell no” that was displayed upon my screen. Band came and went. No flashes. Finally, Calculus. Today, our teacher was gone for something, so our sub let us work with the person sitting behind us. Alex and I finally cleared up what was going on, in a very hushed conversation. “Why has Catherine been acting weird around me all day?” “Jess told.” “What? But why?” “She was so grateful you let her suck you, but then she decided that since you left and we destroyed her, you didn’t really care. So she said she was going to tell one person every day until you made it up to her.” “How am I supposed to do that? Have a foursome with you, Jenna, and Lauren so I can do to you what you did to her?” “She just wants sex.” “Oh, well I can do that. But what do we do about Catherine?” “Fuck her to, if she’s up for it. From what I can tell, she would be a great fuck.” Alex slid a slip of paper across the desk to me. “This is Jess’s number. She has yours and is waiting for you to text her. After school should be soon enough.” The rest of the day passed in slow agony as I awaited the time when I could text the sultry sophomore that would soon be riding my cock. **** After English, I hightailed it out of class. I needed to send Jess that text. So I quickly sent her a text that said “when do you want to do it?” It didn’t take long for her to send back “now. your car. we will discuss it” And so I went to my car, where Jess was already sitting in the passenger seat, waiting for me. I got in the driver’s seat, and looked over at her. She smiled sweetly and said “So, is your house good? I want your cock.” Suddenly, a pair of hands covers my eyes from the back seat. “What the hell?!” Jess laughed. “Don’t worry, it’s just another person that wants to give you a try.” “Who?” “Cassidy, silly.” I breathed in sharply Cassidy was Jess’s best friend. They looked similar, except Cassidy’s ass and tits were a little bigger. Cassidy also wore braces, and instead of tennis shoes like Jess, Cassidy wore Uggs. She uncovered my eyes, and I glanced in the rear-view mirror at her already cum-covered face. My look of confusion must have showed, because Jess smiled and told me Cassidy ate her out every day during their eighth hour PE class. Needless to say, I sped home, wanting a piece of those asses. Cassidy and Jess let themselves in while I ran around back to grab the extra keys from the garage. I didn’t want anyone entering who didn’t have a key. This was my time. When I entered my house, I could hear moans coming from my parent’s bed room. I cautiously walked my way over, only to discover that it was Jess and Cassidy. Jess had taken the liberty of removing her short jean shorts, panties, and shirt, leaving her with just her black lacey bra. Cassidy had removed everything before putting her Uggs back on. She was completely nude and ready for taking. Jess’s eyes were closed and her head was thrown back. Cassidy had one hand on her tit, the other trying to get Jess’s bra off. Her head, meanwhile, was busy being buried between Jess’s legs, eating her out. As quietly as possible, I removed all of my clothes. My erection was clearly visible in my jeans before I removed them, and now it was standing tall, waiting for relief. I made my way over to Jess and her open mouth. The bed was fairly new, so it didn’t squeak as I crawled on it and stood on either side of Jess’s head. I eased myself down so my cock was inches from her face. And without warning, I plunged it into her waiting mouth. She choked and gagged at first, my cock an obvious surprise to her. However, her mouth quickly formed around it and began to lick my cock. I slowly pumped myself in and out of her warm, moist mouth. Her breathing became rapid around the base of my cock and she began moaning onto it. I’m pretty sure that was from Cassidy bringing her to an orgasm. As the humming subsided, I grabbed the headboard and repositioned my legs to get leverage. Then, I f***efully shoved my shaft in and out of her mouth. I facefucked her for a couple more minutes before I felt pressure building up in my balls. I moaned slightly, and I felt Cassidy wrap her arms around my waist. She pulled me back and to the side so I was sitting next to Jess. “Don’t go too fast, big boy,” Cassidy giggled as she wrapped her hand around my shaft. “I told you it was big, Cass. Did you bring that condom?” Cassidy reached into one of her Uggs and pulled out a condom. She smiled seductively. My erection somehow grew as I saw her cum covered brace face. Jess leaned on my shoulder. “She’s great at eating out. She rubs her braces on my clit and it just pushes me over the edge every time. I really wish I could braces to return the favor.” Cassidy just smiled and dropped to her knees on the floor beside the bed. She took my cock into her mouth, careful not to bite me. Her form was a little sloppy. I didn’t mind because I figured it was because more of a rug muncher. That suited me just fine. It meant that she had a perfectly good gag sitting right behind me when I fucked her. She wasn’t nearly as practiced as Alex or Jenna and her s****rs. Her tongue was a bit all over, but not in the good way. She wasn’t sure whether to use it or put it in her cheek, or under my dick, or on top of it. She kept her lips curled into her mouth so her teeth wouldn’t scr**e over my dick, but she occasionally lost her holding and her teeth lightly bit on me. It didn’t feel too bad, but it wasn’t something I wanted to make a habit of happening to my member. Jess reached down and grabbed Cassidy’s head, forcing her to suck me deeper. Her pretty face was contorted in a look of surprise. She choked slightly as her mouth widened to take my cock. She came up for air quickly before she went down for more. She deep throated me again, barely choking this time. She excitedly came up again. “I did it without choking that time, Jess!” “Good job, Cass. Now, rub him off.” “Do what?” Cassidy had a confused look on her face. I wish I could blow my load right then to cover her face. “Grab it, and stroke it. And it’s REALLY effective if it’s pointed at your face and you smile up at him,” Jess said, as she reached around and grabbed my shaft. She stroked it slowly, showing Cassidy the proper technique. Cassidy reached up and grabbed it too. Jess moved her hand and placed it over Cassidy’s, guiding it for a short time before letting her do it on her own. Her hand was a little cold, but it warmed up pretty quickly. I could feel my heart beating in my cock as she stroked it slowly, no knowing she was going to get a very large load right in her face. Jess moved from behind me to behind Cassidy, whispering in her ear words that fell short of me. Cassidy smiled up at me, making eye contact. And without warning to me, I spewed. The first load hit Cassidy’s nose. As she tried to turn away, Jess held her head in place. Her other arm was wrapped around Cassidy’s middle to prevent her from using her arms to block her face. The second shot landed in Cassidy’s black hair that was drawn back into a pony tail and drifting over her left shoulder. The next two shots hit her left eye and forehead. The fifth and final shot hit her lips. Cassidy’s tongue instinctively shot out to lick it clean. She moaned as she tasted her first male jizz. “That was great.” I couldn’t muster much other than that. Cassidy smiled and opened her right eye. “Jess, why didn’t you tell me this was so awesome.” I saw her smile deviously behind Cassidy’s head. “Just wait until he get inside of you.” Before she could say anything, Cassidy was being f***ed onto the bed by Jess. Jess pushed her onto her stomach, and then sat much like Jenna did when I first buttfucked Alex. She held Cassidy’s arms and she made Cassidy’s face be shoved into her pussy. She looked at me and told me to put the condom on then take whichever hole I wanted. I knew her ass would be tighter than anything I’d ever fucked before, so I chose to pop her cherry. I slowly pushed my way into her tight virgin pussy. Jess laughed as I got a surprised look on my face. “We took each other’s virginity with a strap-on. We figured it would be less painful when we decided to finally have sex.” I moaned at the thought of the two sexy teens sliding a fake dick into each other’s sopping wet cunts. The thought almost sent me over the edge, but the last couple days taught me to hold it in. I eased myself in and out of Cassidy for several minutes before I started to speed up. She had given me several sl**pless nights with her sexy body, and she had no idea. I was going to make her pay anyways. I began to furiously pound the vagina I should have removed the virginity of. She moans loudly into Jess’s vagina and Jess moans out loud. After several more minutes, I couldn’t take it anymore. I had blown already today, and having been made to cum several times since Monday, I couldn’t take it. I pulled out, and winked at Jess. My hands gripped Cassidy’s hips firmly as I rubbed my cum-covered dick on her virgin asshole. She winks back and reaffirms her grip on Cassidy. As she nods, I slowly slide my dick covered in Cassidy’s cum and a combination of her and Jess’s saliva into Cassidy’s puckered little hole. She screams into Jess’s pussy, the sensation new, or so I thought, to her. “This is better than prom last year!” She somehow got her head away from Jess enough to talk. I froze in her bum. “Didn’t you go with Trevor?” Trevor was the quarterback and a senior last year when Jess and Cassidy were freshmen. “Yeah, I knew he’d want something after prom, so I promised him a blowjob. He made me go blindfolded because he said it really turned him on. When I went down on him, I felt someone else grab my hips as he grabbed my head and f***ed it farther down on his cock. The person that grabbed my hips stuck it in my ass and I would have woken up the neighbors screaming if I didn’t have that cock in my mouth. Turns out that the cock that was in my mouth was his b*****r’s.” I resumed fucking her halfway through that story, so naturally it took a lot longer to tell. She had to stop between words to moan. Jess grinned through the entire thing, horny as fuck. Cassidy collapsed not long after, and Jess let her go. She crawled over the sexy body of her best friend and pulled my cock from her bowels. She turned around, stroking it, and then pushed it into her own ass. She fucked herself on my rod for only a couple minutes before it became too much for me. I moaned and she pulled it out and turned around. I didn’t even have to stroke it, and I blew right on her pretty little face. Three or four loads, one right after the other, hit her face. She moaned and rubbed her tits. As I collapsed, she turned on Cassidy. They began making out furiously, Cassidy trying to get as much of my cum off her friend as possible. I watched as Jess quickly switched it all into a 69-position and they ate each other out for several minutes. I got hard again, and jacked off, but it didn’t take long before I was blowing my third load of the day on Cassidy’s face. Nearly unconscious, Cassidy and Jess helped me up to my room where Jess gave me a farewell blow job before Jenna picked them up outside. **** I woke up to my mom yelling at me that supper was ready. I was dressed. And there was text on my phone from Jess. “That was fun. Next time we add catherine and my pussy to the menu ;)”