7 comments/ 67331 views/ 76 favorites Cumming on Caitlyn Ch. 01 By: BradGarrettStories Hey there! This is a fun tale that even I will admit stretches the boundaries of realism like a rubber band, but then again, not every story has to be plausible. Sometimes our fantasies take us to the ridiculous, but that's fine in my opinion. That being said, with so many different viewpoints and attitudes regarding sex, this scenario is not completely outside the realm of possibility. There is a bit of sexual humiliation and degradation, but it does turn out differently than you might expect upon reading that. I also want to thank the fabulous Katie_Ames for not only editing this story with me, but also for believing in me when I came to her with this crazy idea. I think we made it work, especially if you had seen some of the earlier drafts. ;) Enjoy! ------------------------------- "Dude, she is going to be so pissed at you," said Darren quietly as he stood by, watching his friend Matt stroke his cock. "No way man, she will love it," replied Matt quietly as he stood to the side of the couch, his pants undone and his hand silently stroking his erection which was pointed towards the face of their sleeping friend Caitlyn. "Whatever dude, it's your funeral," said Tyler, the last friend of the quartet. Now in the summer after their senior year, the three guys and the lovely, sleeping Caitlyn, had all become friends after meeting on the swim team their sophomore year. The past few years had seen them grow into a fun, close-knit group. They were inseparable and to them, Caitlyn was just like one of the guys. Yes, she was beautiful with a great body, but she liked what they liked. She was an avid football fan, loved cracking jokes and making fun of people, drinking beer with them whenever they could sneak some and she was able to hang with them when it came to shit-talking each other and pulling pranks. Throughout their time knowing each other, they loved to rib each other and attack an unsuspecting member of the group with some sort of playful prank. They did everything from drawing on each other's faces with permanent marker when someone passed out to pantsing each other at inopportune times. Other times, they would attack each other with shaving cream or barge into the bathroom while someone was doing their business and surprise them with water guns or silly string. On more than a few occasions, the guys had even flashed an unprepared Caitlyn with their dicks. There was a lot of sexual smack talk between the guys and Caitlyn, but to the group's knowledge, no one had actually slept or even messed around with her. They had, however, seen her boobs a few times. The first time was after a particularly snarky comment about the size of the guys' dicks when they group flashed her. None of the guys were small by any means, but that didn't stop her from saying that they were "built like little boys." The guys attacked her and relentlessly tickled her and as she writhed around screaming and flailing, her tiny t-shirt had rode up to reveal her braless B-Cup breasts. The second time was during a bout of drinking and Caitlyn had meant to flash the boys her bra, but in her inebriated state, she had forgotten that she had removed it earlier. Caitlyn had a propensity to go braless about as much as when she actually wore one. Her breasts were perky enough that she really didn't need to wear one and she enjoyed the freedom. She also got a bit of a thrill watching as the guys tried desperately to sneak peeks at her erect nipples through her shirts without being caught. The only other time that the boys had been given a glimpse of her tits was she they were out swimming in her parents' pool, only this time it had ended up being more than just a glance. She had laid out on her stomach and undid her bikini top to take in some rays while the boys swam and roughhoused in the pool. She flipped over and let her bikini top just rest on her tits instead of refastening it back. As she lay there with her eyes closed, Matt had quietly exited the pool and in a flash, grabbed her top and jumped back in the water. She quickly bolted up, her hands covering her breasts and demanded that they give her back her top. They ribbed her and asked her what she would do to get it back to which she said, "Fine, you wanna see my tits, I don't care." She dropped her hand revealing her perky breasts to the leering boys. They eventually gave her back the top, but not before getting a good look at her magnificent chest. That was their relationship. It was fun and full of pranks with an undertone of sexuality. Even with all that, Matt's newest idea for a prank was one that was probably pushing the line. While sitting around and watching a movie, Caitlyn had drifted off. This was something each of them knew was a dangerous thing to do in this group. Dressed in only a pair of soffe short and a tank top, she looked so beautiful and peaceful curled up on the couch. Matt had gotten the idea in his head that he would cum on her face when he noticed that she had fallen asleep. "Guys, she's out," he said quietly. "I have an idea." With that, he stood up and unzipped his pants, pulling his soft dick from its confines. He immediately began to stroke himself to hardness while looking down at the beautiful face of their friend. The guys laughed at him, but made their warnings apparent. She could really get pissed at him, hell at all of them, for this prank, but once Matt had an idea in his head, it was almost impossible to change his mind. She squirmed a bit on the couch, trying to get more comfortable, but remained asleep as her friend silently jerked his cock at her. Tyler and Darren stood on watching, unable to turn away from the lurid sex act that was happening in front of them. They all had a desire to fuck Caitlyn. She was sexy, fun and gorgeous. Closer and closer to release, Matt was stroking his cock faster and faster. His dick was maybe a foot away from her face as his orgasm began to build. He could feel himself getting closer and right before he was about to explode, he said loudly, "Caitlyn!" Caitlyn sleepily opened her eyes to her name being called and right as she noticed the head of Matt's dick pointing directly at her, he exploded with long strings of hot cum across her sleepy, beautiful face. She screamed out at the debasement and moved to get out of the way, but Matt landed four good blasts of cum on her before she was able to move. "What the fuck?!?!" she screamed out as she stood up, her face dripping with Matt's load. Matt started laughing now and the guys just stood back, unsure of exactly how this was going to play out. "Did you just cum on me?" she exclaimed, her hands up in a questioning, unbelief stance. "You know something is going to happen to you if you pass out around us," Matt said as he continued laughing and holding his deflating cock. "So you think it is OK to just nut on my face while they watch?" she said with a bit of anger in her voice, her arm angrily pointing at the two bystanders. Matt just stood there with a smartass smirk on his face. Unbeknownst to the other guys though, this wasn't the first time Caitlyn had been the recipient of Matt's cum. ~ A few weeks back, right after graduation, Tyler and Darren had been unable to hang out so Matt and Caitlyn spent the day together at her parent's house. Being avid swimmers, they took advantage of the great weather and spent some time in the pool. Matt, who was used to wearing a speedo for the team, went a bit more conservative and wore a standard pair of board shorts. Caitlyn, however, who was used to wearing one-piece swimsuits for events, chose to go with small, bright orange triangle bikini with black trim. The suit clung tightly to her well-toned body and accentuated her figure. He was already in the pool when she came out on to the deck from the house and he couldn't help but steal glances at her when he felt he could. She really had blossomed over the past few years from a somewhat awkward, lanky girl to this beautiful woman he secretly watched now. Matt, along with the other guys, had also developed well over the past few years. Rigorous workouts and constant training had left them all in peak condition. It wasn't the first time he had lustful thoughts over Caitlyn. Hell, all the guys had. They had all used her image while masturbating on more than one occasion. It didn't help that she was dressing in skimpier clothes now and flirting with them more. Caitlyn was simply beautiful. Smokey blue eyes with a sleepy, seductive look to them coupled with full lips, dimples and a slightly raspy voice that sounded sexy and exotic was enough to turn the heads of lots of guys. Matt and the rest of the guys were protective of her though. She was their friend as well as their desire and they weren't about to allow some dipshit mess with her. She placed a towel down on one of the reclining lounger chairs, smoothing it out and giving him a great view of her ass. She then turned to Matt who was now resting with his arms folded on the side of the pool and said, "I think I'm just going to lay out." She then got a stern look on her face and said, "Don't be trying to steal my top again either or I will kick your ass." "Oh, like you could," laughed Matt. "But come on, don't just lay out, come swimming. I don't want to fuck around in here by myself." "Oh, so you wanna fuck around with me in the pool then," she said, her double meaning apparent. "Maybe," he replied and smiled. "Well too bad Romeo, I wanna lay out today," she said. "Not an option," he said. "You're getting in this pool with me, one way or another. Do you wanna do this the easy way or the hard way?" She started to sit down on the chair and said, "Neither. I'm laying out and you aren't changing my mind. Maybe I'll swim later, but for now, I just want to get some sun." "OK," he said, "just remember, I gave you a chance." He pushed himself up out of the pool and started to walk over to her. Caitlyn didn't move and just reclined back onto the lounger. He stood over her now, dripping with water, his suit clinging to his body and she took the chance to eye-fuck him from behind her sunglasses. He was handsome and his body was spectacular. Well defined chest flowed perfectly into his sculpted abs which led directly to his low hanging board shorts. What really caught her eye was the bulge he was sporting which was very apparent thanks to the wetness of his suit. "Last chance," he said. "I already told you, I would swim in a little while, but not right now," she said. "Now go away little boy, you are blocking my sun." He looked down over her fantastic body and then went for the strike. If there is one thing he knew about Caitlyn's body, it was how incredibly ticklish she was. He bent over and immediately jabbed his fingers into her sides and started tickling her. She immediately screamed out and bolted up into a sitting position, wildly grabbing at his hands and trying to push them away. With her sitting up now, he grabbed her closest arm and pulled her up, her flailing keeping her from being well grounded and immediately threw her over his right shoulder. He hooked his arms around her legs to keep her in place and then turned towards the pool. "Dammit Matt, put me down," she wailed as she tried to wiggle out of his grip. He said nothing in return and just headed back from where he came. As he walked towards the water, he turned his head slightly and took in the curves of her fantastic ass which lay, squirming, right next to his face. He could only imagine what it would be like to spank her. Sure, he'd slapped her on the ass plenty of times, but there was a difference between slapping an ass playfully and spanking a naked ass in an act of sexuality. Without really paying attention to it, his cock had become even more engorged from the close contact with her. He got to the edge of the pool and switched his left arm over to her legs to steady her and placed his hand on her hips. As he started to lift her off his shoulder, she screamed out quickly, "No, no, no, no, no, no." He ignored her pleas and with a strong push, he lifted her off of him and threw her into the pool. She surfaced from under the water, gasped for air and wiped her face so that she could open her eyes. "You are such an ass," she said, accentuating the word 'ass'. "Uh, hello, is this the first time you've met me?" he quipped back. He looked down at her and she once again took in his body as he stood over her. She couldn't help but notice that the bulge in his suit had grown. Had he gotten hard just from messing with her? She was so horny over the last few days and this was definitely not helping. All she could think about now was getting that cock into her pussy. Somehow, today was most likely going to be the day that their friendship changed, even if she had to be the one to jump him and fuck his brains out. "Uh, hello, my eyes are up here," he said, noticing her gaze was fixated on his crotch. Not willing to give in so easy to her desires just yet, she decided to do business as usual and mess with him. "Yeah, sorry about that. You have to stare pretty hard to find something so small." "Oh, you are gonna get it," he said and jumped in. She screamed out as he attacked her and tickled her more. She was laughing loudly but managed to get out another shot at him. "It's like, aaaaaaah, hahaha, it's like trying to find Waldo, haha, aaaaaaah, ha, you can never find him." She continued to laugh as he tickled her and he then went to dunking her under the water. They played and roughhoused for a bit before settling down and just lazily swimming around for a while. "So whatever happened with you and what's-his-name?" he asked. "Who? Oh Brice? Good God, I didn't tell you?" she asked. "Nope, not that I can recall," he said. They had moved over to the edge of the pool at this point. "I caught him sexting with another girl. Like really dirty shit too," she said. "Oh, that sucks. You really liked him, didn't you?" he replied. "Well, he was hot, sure, but the dude couldn't carry on a conversation for shit," she said. "What a douche. Did you know the girl?" he said. "Oh my God, it was his fucking cousin, can you believe that shit?" she said animatedly. "What?" he replied. "Yeah, yeah, and he's telling her shit like, 'I can't wait to fuck your ass again baby' and 'I really wish you'd let me fuck your pussy'. He even told her he wanted to stick a cucumber up her ass. Who the fuck says that to their cousin, especially when I'm right fucking there ready and willing for him to do that shit to?" "Wait, you'd let him stick a cucumber up your ass?" he said, surprised. "Really? That's what you focused on? He's fucking," she paused slightly for effect, "his cousin," she said emphatically. "Yeah, I got all that. He's an idiot, he's fucking his cousin, whatever. I don't give two shits about him. You, I do," he said. "Aww, that's really sweet of you," she said. "Yeah, yeah, now back to the cucumber in your ass," he started. "Oh my God, shut the fuck up," she started. "What I want in my ass is none of your concern." She gave him a snarky face and then changed the subject. "Hey, let's go inside and watch a movie. We can sneak some beers too. My parents aren't going to be home for a while." She went to the edge of the pool and started climbing out. He blatantly watched as her ass came into view and marveled at the way her suit cling tightly to her firm cheeks. Without giving it much thought, he reached up and smacked her across the ass. She yelped and jumped the rest of the way out of the pool. She then turned to him and sarcastically called him, "Ass!" "Yes, thank you for the anatomy lesson, but I already know what it is," he said with his normal smartass smirk. She let out a frustrated growl, turned and walked inside. Matt pulled himself out of the pool and walked up to where his towel was. He began to dry off as he watched her doing the same. His thoughts couldn't stay away from imagining his friend naked and his cock buried deep inside her pussy. Today was a rarity. He had almost no alone time with her so he told himself that today may be the best opportunity to make a move on her. When he was dry enough to go inside, he threw the towel over his shoulder and waited for her to finish. He continued to take in the view of her sexy body and had to readjust his cock in his shorts so that his hard-on was not overly obvious. She turned around almost immediately after he made an adjustment, maybe a second away from catching him touching himself. "You ready?" she asked. "Yep," he replied. The two went inside and headed for the living room. "I'm gonna grab a beer," she said. "You want anything?" "He plopped down on the couch and said with a grin, "Got any cucumbers?" "Fuck you," she said with a laugh. He laughed back and said, "Not right now, but maybe later. For now, I'll just take a beer too." "Whatever," she said and walked into the kitchen. She came back with two bottles and handed him one. "Watcha wanna watch?" she asked. "Got any porn?" he replied. "Oooh, sorry, no porn on DVD there buddy," she teased. "How about Gravity?" "That's fine, whatever. Just keep me well lubricated and we can watch whatever," he said. She moved over to the shelf of Blu-Rays and selected the movie. With her back to Matt, he took full advantage and let his eyes roam over her body once again. He could feel there was a change in the air, something he didn't normally feel around her. Nerves maybe? Either way, it was very reminiscent of other times he had been with a girl before they started to do anything sexually. She popped in the movie and came over to the couch and sank down next to him, curling her legs up under her which leaned her still bikini clad body in Matt's direction. She grabbed the remote and started the movie. They sat in silence, watching the movie and occasionally looking at the other one. Nothing was said which was a rarity between them. Caitlyn practically gulped down her first beer and with a quick shake of the bottle jumped up and said, "I'm gonna get another one." Matt looked at his beer, gave it a quick shake and said, "Hey, grab me another one too." "Get up and get it yourself," she quipped back. "I'm not your beer bitch. In fact, get your ass up and go get me one too." She turned around to go sit back down and as she passed in front of him, he grabbed her arm and pulled her down into his lap. She squealed and landed squarely on his crotch and immediately felt his hard-on beneath her ass. It took her a moment to process what she was feeling through the thin materials of their swimsuits, but it was clear. He was engorged. His cock was hard. He was turned on. He grabbed her other arm by the wrist and held her in place. She feigned disobedience and tried to escape his clutches, laughing with him and squirming, but she was really enjoying his hard member that was pressed against her ass. He switched his position with his hands and began to tickle her exposed flesh as she sat sideways on him. She thrashed around and began to scream and laugh. He watched as her sexy body twisted and flexed as her fantastic ass ground against his aching cock. There was a brief pause in the assault and she defiantly taunted him. "Whoa there soldier! What's that doing there?" she said as she looked down, indicating that she felt his hard dick. Without missing a beat, he looked at her and said, "What's it look like? I'm poking you in three spots at once!" He immediately went back and began jabbing and poking his fingers into her side which initiated another round of screams and laughter mixed with her body squirming on top of him. She eventually thrashed and kicked so much that she moved from sitting sideways on him to straddling him, her tan, toned legs on either side of his as they sat on the couch. He stopped his attack, his hands resting on the sides of her stomach and her hands lightly grasping a mix of his hands and wrists. Her young, pert breasts heaved in front of his face as she breathed heavy, working to catch her breath. Cumming on Caitlyn Ch. 01 "Uh, hello, my eyes are up here," she said, echoing his exact words that he had taunted her with earlier by the pool when he caught her looking at his crotch. "I know," he said, "but I like the view I have right now." He smiled and then looked up at her. Their eyes locked and they stopped talking. They both, simultaneously, began searching out the answers to unspoken questions in the face of the other. Eyes darting back and forth from one to the other while the sat in silence except for the sound of their breathing and the unnoticed movie playing in the background. Neither of them could be certain how long they sat like that, staring at one another. He waited for the right sign. The little tell that would let him know that she wanted him as much as he wanted her. She finally gave it to him. The slightest notion, but he picked up on it like it was a flare going off on a darkened street. She subconsciously bit the left portion of her bottom lip, an almost imperceptible act, but he caught it. He removed his right hand from her side and brought it up, sliding it across the left side of her face, his fingers parting her slightly damp hair and pushing it back from her face. He grasped her head and without hesitation, pulled her face towards him and kissed her dead on. Their lips mashed together and they passionately kissed. It was a hungry act, both starved for the connection. Her hands went from his wrists to the back of the couch on either side of his head and she fell into him, her breasts smashing against his chest and her hair shrouding their faces. His left hand began to explore her body, up her side and then down again before grasping and squeezing her ass. She began to rock her hips, grinding her pussy against the shaft of his cock. He removed his right hand from her face and wrapped it around her body, pulling her in even tighter. Their tongues danced in each other's mouth, moans of pleasure coming from both of them. He moved his hand again and started untying her bikini top. The string easily gave way from her back and then he moved to the one around her neck, making quick work of that one as well. She pushed up, presenting her breasts to him. The flimsy material clung to her upturned tits. He reached up and pulled the top off of her, revealing her gorgeous, erect nipples. He took one mound in his hand and moved his mouth to the other, taking the hard bud into his mouth. She let out a moan as he sucked and nibbled on her. He moved his other hand from her ass and used both to fondle her while switching from one to the other. He then pulled her back down and they resumed kissing. He could feel the warmth of her tits as they pressed against his chest. He placed both hands back on her ass and helped her rock her body against his straining cock. With a swift motion, he grabbed both of the string ties on either side of her bikini bottoms and pulled them out, releasing them. He pushed her back and motioned for her to stand. She reluctantly got off him and stood before him, the bikini bottoms clinging only to the moisture between her legs. He pulled them down, revealing her bald pussy, wet and glistening from her excitement. As he sat before her, he ran a finger up between her legs and felt the slick juices between her lips. He inserted a finger into her hot hole and watched as she became weak-kneed. He removed his finger and quickly stood up in front of her. He kissed her again before pulling away and began to undo his shorts. Without hesitation, she dropped down to her knees in front of him and her hands went to his bulge. She cupped the large protrusion as he finished undoing his shorts and then he pulled them down, his cock bouncing into view. She grabbed it, fueled by lust, and began to stroke him. She watched, as did he, her tiny hands grasping and wanking the hard shaft. She leaned in and took the head of his dick into her mouth. He grasped her head as she began to blow him and he watched his dick slide in and out of her beautiful face. Her eyes were closed and she was moaning even more than him. He was lost in the feeling of her talented mouth as her lips and tongue explored his cock and he couldn't believe his luck. He, like all of the guys in the group, had always wanted to fuck her and here she was, naked on her knees with his erection in her mouth and she was hungrily devouring him. He could tell that she wasn't just sucking him because she felt like she had to. She was turned on by having him in her mouth. He felt like he could have let her just suck the cum right out of him, but he didn't want to waste this opportunity should it be the only one he got. He reached down and pulled her up, his cock slipping from her mouth. She had a bit of disappointment on her face, but he ignored it and pulled her in, kissing her once again. She reached down and began to stroke his shaft and he reached down in turn and started to finger her wet pussy. It was sloppy and needy by both of them, two friends caught up in the passion of their first time together. That was elevated by the fact that this was a somewhat forbidden affair. They were friends. They were part of a group that was close-knit and sex between the group was not done. But in this moment, they were betraying the group. Betraying their social status as friends and giving into their hormones. They both had what the other one needed. The means to a physical connection and most importantly, an orgasm. He pulled her back down onto the couch, she once again straddled him. Their lips continued to press feverishly against each other as their bodies adjusted for the impending penetration. He reached around her body and grasped his own cock, lining it up against her sopping pussy. She felt the thick head of his dick parting her puffy, red lips and sunk her body down onto it, impaling herself. In unison, they both moaned as he penetrated her for the first time. He grabbed her ass, firmly squeezing the tight flesh between his fingers and began to rock her up and down, plunging a little more of his cock into her tight pussy with each thrust. They went at it with reckless abandon. She used her legs to rise and fall back on his cock and he assisted her by holding her ass and rocking her. They kissed. Their mouths feverishly tasted each other, kissing between moans and gasps for air. He moved down and took one of her nipples between his lips and sucked them as her body rose and fell, repeatedly impaling herself on his dick. They fucked like this for a good ten minutes, kissing and groping each other, fucking like they were starved for release. She gyrated her hips so that he would continually hit that perfect spot inside of her. She could feel her orgasm coming. Building. She began to buck on his cock, her body was shaking. "Oh my god, oh my god," she said over and over as she built towards release. "I'm so close," she announced, "I'm going to fucking cum, oh my god, oh my god!" She bucked against him until her orgasm finally exploded through her. She continued to ride him, drawing out the feelings of immense pleasure. His hands gripped tightly against the flesh of her hips as he continued to rock her body up and down on his sensitive dick. He could feel himself getting closer. "I don't have a condom," he said but didn't stop thrusting into her tight pussy. "Are you on the pill?" "Just pull out and cum on me," she said, her breathing still ragged. "OK," he gasped, his hands speeding up and slamming her up and down on him. "Do you want me to cum..." heavy breath, "on your tits..." another heavy breath, "or your back or what?" "My face," she exclaimed, "cum on my face." They were both breathing heavy, loud grunting and moaning filled the room along with the sounds of skin slapping against skin. "Oh my God, I'm gonna cum," he said and pushed her off of him. She stumbled down to the ground and repositioned herself on her knees in front of him. He was already standing now and stroking his cock, pointing it at her upturned face. Her hair was wet with sweat, partly sticking to her cheeks and forehead while the rest remained disheveled. He only stroked a few more times before he threw his head back and let out a loud roar as his cock exploded across her face. He regained control of his head and looked down, catching the second blast shoot from his dick on to her skin. Her mouth was open and her eyes were closed as she lost herself in the feeling of his hot cum covering her. He let go a few more large jets before his orgasm subsided. Caitlyn was dripping with Matt's large load, but she was not content to let it end just like that. She leaned forward and found his cockhead which she took in her mouth. Her hand reached up to stroke him and she began to clean. She bobbed back and forth slowly, removing the residual cum and extracting the rest from inside him. She finally let his dick slip from her mouth with an audible 'pop' and then sank back down on her folded legs. She held her head up to keep the cum from sliding down and off her face and just smiled, her eyes still closed. "Holy shit," she said, her words causing the strings of cum across her mouth to bubble and sputter. She licked her lips, drawing globs of the hot cream into her mouth and down her throat before finishing, "that was awesome." Matt fell back against the couch and reclined on the cushions, half-lying, half-sitting and tried to catch his breath. Caitlyn stood up and walked out of the living room only to return a few minutes later. Her face was now clean and her hair was fixed, but she was still as naked as Matt. She dropped down on the couch next to him and curled up in a ball with her head resting on his chest. "Fuck, why haven't we done that before," she asked. "Beats me," Matt said. "It definitely isn't from a lack of want." "Well, it better not be the last time," she said. "Oh, it won't," he said. He titled his head down to hers, his hand caressing her long hair and said, "Sooooo, a facial huh?" She buried her face in his chest and said, "Oh my God, I know. I've just always wanted a guy to cum on my face and it just seemed like a good time to ask for it." "Hey, I'm not complaining. You look hot with cum on your face, that's just not something I expected from you," he said. "Well, then you definitely wouldn't expect what I did in the bathroom," she said. "What?" "I didn't just wipe your cum off my face," she started. "I collected it with my fingers and ate it." "What?!" he exclaimed. "You should have done that in here. That would have been fucking hot to watch. You do not need to keep that shit a secret from me girl." "Wanna know another secret," she said, curling up closer to him and looking up at him. He just nodded, looking down at her face before letting his eyes wander further south to take in her naked body once again. His hand came up and began to grope her exposed tits. "I've actually wanted to fuck all three of you for a very, VERY long time," she said. There was no humor in her statement, it was just a confession. A long held, pent-up confession. "Well," Matt started, "I've got news for you. We've all wanted to fuck you too." "Really?" she said, repositioning herself to get a better look at his face so that she could judge the seriousness of his response. "Oh fuck yeah," he said. "They've told you that?" she asked. "No, not flat out," he started. "We don't just sit around talking about how we want to bang our hot friend, but we all know we do. Trust me." "Oh fuck me," she exclaimed. "I've been rubbing my pussy raw thinking about fucking you three and NOW you tell me that you all have secretly wanted to fuck me too." "Fucking us three?" Matt smirked. "Sounds like someone wants to get gangbanged." He laughed at himself. She did not. "Well, no, I didn't mean it like that," she started, then trailed off, "at least, not all the time." "Fucking hell, you have thought about it, haven't you?" he exclaimed. "No," she said, but her face gave away her deceit. He just stared at her, as if he was willing the truth out of her. She stared back, matching his gaze, trying to keep the truth concealed, but she lost out. "Ok, yes," she said and quickly covered her face with her hands. "You dirty slut," he laughed. The degrading name sent a bolt of electricity straight to her clit, but she played it off as embarrassment from her confession. She pushed him against his chest and yelled, "Shut up, ok? It's not like I think about that every time, but fuck, you spend most of your time with three hot, half-naked guys and you are going to eventually think about them all sticking their dicks in you. "Uh, no I wouldn't," Matt said, feigning a look of disgust. "Oh for fuck's sake, you know what I mean," she said. "So, is it like a train, one of us right after the other or do you think about having all of us inside you at the same time?" he questioned. "This is so fucking embarrassing," she said and hid her face again. "Well, which is it," he pushed on. With her face still buried in her hands, she mumbled, "Both." "Well, holy shit, we've been hanging out with a closet nympho and we didn't even know it," Matt teased. "I can't help it," she said, "and that's not even the most embarrassing part." "Oh, do tell," he said, readjusting himself on the couch. His cock was coming back to life and laying heavy against his inner thigh. "Well, no point in playing it coy anymore," she said. "What really gets me going, what really makes my pussy wet, is when..." She stopped, embarrassment stalling her confession and burning her cheeks red with humiliation. "Oh hell no, you can't stop there," he said. "Fine," she said frustrated. "My best orgasms are when I think of you all being very demeaning to me." "What?" he said, stunned by this admission. "Are you fucking with me now?" "No," she said, "I'm not. Think about it. All day long, we are together and you all fuck with me, rip on me and tease me. That's a huge part of our friendship. I just imagine, as you all are fucking me, that you do that, only on a sexual level." "Ok, that makes sense," he said, his eyes trying to figure out how serious she was. "Like, what are we doing that makes you so hot." "Oh you know, calling me names, teasing me, spanking me, tying me up and tickling me or playing with my body but not letting me cum," she started. "Oh my God, this one time, I dreamed that you all made me dress up in a ridiculous outfit and crawl around on my hands and knees, going from one of you to the next and then the next and each time I got to one of you, you made me beg you to let me suck your dicks. You fucking made me beg and it was so humiliating, but fuck it made me hot. But then you would only let me do it for like a few seconds before making me stop and pushing me on to the next one. You all were making me expose different parts of my body to you in very slutty ways and you were calling me all sort of cheap names. I woke up thrashing and cumming in my bed with my fingers buried in my pussy." "So you are telling me that I've been wasting my time trying to get Tara, Miss Prudebitch, to do something, anything, with me and yet, I've been hanging around with a dirty slut this whole time? That bitch is so prude, she will barely even stroke my dick, let alone suck it and here you are dreaming of getting gangbanged by us," he said. Caitlyn's pussy flooded as he called her a dirty slut and her cheeks flashed red with heat once more. "So, you really want to be our little fuck toy," he said, becoming bold and empowered with this new information. She nodded, her mouth open and her lips parted. He could see her visibly swallow hard. She was quiet, but breathing hard, visibly excited from divulging her secrets to Matt. "Oh, I can make that happen. We've all wanted to fuck you," Matt said, "but I want to play with the fuck toy a little more by myself first." He grabbed her and pulled her to him, kissing her once again and running his hands down her body to her ass. ~ But that was then. This was now. She moved towards him and pushed him on his chest. Her face was still covered in his cum and was now starting to drip down, the fresh cream making lurid spots on her shirt. She had made no attempt to clean herself. "What the fuck is wrong with you?" she said. "Oh, whatever," he said as he tucked his dick back into his pants. "You know you liked it girl. You're just mad because you didn't get to watch me stroking my dick the whole time." She glared at him. He looked back at her, their eyes locked and with the most subtle of movements, he widened his eyes and nodded his head slightly towards her. It was a minute expression filled with a world of information. This was the catalyst that she had wanted. This was how he was making it all happen. "I gotta say though, you look hot with cum on your face," he said with a laugh, echoing the same thing he had said to her when they first had sex. He was hoping this nod back to their secret affair would be enough to spark the memory. The room was tense. Again, silence as she glared at him. And then the realization of what he had set in motion sparkled across her eyes. She spun around to look at Tyler and Darren. "And you two just watched as he jerked off on me. Just let him do it, huh?" "Hey, you know when he's going to do something, there's no talking him out of it," said Darren. "We told him you'd be pissed." "Pissed?" she said. "You think I'm pissed just because fucktard over here came on me while I was sleeping and my two other closest friends just stood by and watched, doing nothing?" She walked up to them, glaring at both of them. "You're damn right I'm fucking pissed," she said with an angry look on her face. Her eyes going back and forth between the two of them. The room was once again filled with silent tension. After keeping them in suspense at what would be her next outburst of anger, she surprised them. "After all this time that we've been friends, everything we've been through together and this happens and you two do nothing. Not a goddamn thing. So yeah I'm pissed because apparently Matt is the only one of you three who thinks I'm sexy enough to jerk off to." The guys stood there in disbelief, trying hard to process what she just said. "Wa . . . wait," stammered Tyler. "You're pissed because we didn't cum on you too?" "You're damn right I am," she yelled. "Three years waiting for any or all of you to make a move on me and nothing." The guys looked at each other and then back at her and quickly started to backpedal. "What the hell? None of us made a move on you because none of us thought you were interested in us that way. We didn't want to ruin our friendship by trying to date you," said Darren. "Yeah, I mean, we all think you're hot as shit, but we were just trying to be respectful of you," said Tyler. "Who the fuck said anything about dating? All day long, I am with three hot guys, each of whom I'd gladly fuck, but none of you has had the balls to try anything beyond pulling your dicks out or trying to look at my tits. Matt may be an asshole, but at least he had the balls to do something," she said. "Wait, you'd gladly fuck any of us?" said Darren whose face was plastered with shock and disbelief. "Fuck yeah I would. As much time as we spend together, we should definitely be fucking. It's fucking idiotic not to. I have needs too and do you know how hard it is to find a guy that wants to date you when your three best friends are dudes?" she said. "Cait . . . Caitlyn, we've always thought you were sexy as hell," said Tyler. "You have?" she said, the cum cooling and drying on her gorgeous face. Her brow furrowed in an expression that could only be described as grateful sweetness, like she was truly touched by his statement. Cumming on Caitlyn Ch. 01 "Oh yeah," piped in Darren. "Sooo, do you think I still look sexy with cum on my face?" she said, a playful demeanor returning to her. "You look sexy all the time," said Tyler. Matt walked over to them now and stood with the group, looking at Caitlyn with his cum drying on her face. "I think this is the sexiest that I have ever seen you look," he said. She bit the left corner of her bottom lip and then said, "Well, if you all think I look good with cum on my face, maaaaybe we should add some more." They looked at her again with surprise on their faces. Her beautiful blue eyes seductively narrowed and she looked back and forth between the two guys. "Matt here already got to cum on my face, without invitation I might add," she said and shot Matt a playful scorn before turning back to the other guys, "so I think it is only fair if you two get to as well. Would you like that? Would you two like to jerk off onto my face?" "Are you serious?" asked Tyler. "Dead serious," she said as she dropped down to her knees in front of them. The guys just looked at her, unable to figure out if she was fucking with them. She could see their hesitation and decided to clear any doubt from their minds. She reached up with both of her hands and placed one on each of their crotches and began to rub their bulges through the fabric of their shorts. She noticed they weren't hard yet, but still seemed to be concealing some decent sized equipment between their legs. The boys jumped at first, her sudden contact surprising them, but they quickly calmed down and enjoyed the feeling of her petite hands massaging them. Almost in unison, she could feel their cocks responding to her touch, growing larger and more rigid behind their confines. "Don't you all want to cum on me?" she asked, a seductive smile creeping across her face. They both nodded, unable to speak. "I'll show you mine if you show me yours," she said, her voice raspy and playful. They looked at her with a puzzled look on their faces. She reached down and grabbed the bottom of her tank top and lifted it over her head, revealing her braless, perky breasts to them. She tossed the garment on the floor, leaving her kneeling on the floor in only her shorts. She reached up and began to fondle her own tits, squeezing them together, her fingers pressing in on the firm flesh. She scooped a glob of Matt's cum from her chest and moved her hands, taking her erect nipples into her fingers, smearing the semen on them and began to squeeze and pull them. This caused her to close her eyes and tilt her head back as the euphoric sensations ran through her body and down to her pussy. "I want your cum so bad," she moaned, exaggeratedly, her eyes still closed. "Please," she begged, "do this for me." The sight of the sexy friend topless and caressing herself as she begged for their cum was enough for them to throw caution to the wind and risk this being some elaborate prank meant to embarrass them. They were both hard as rock and dying to fulfill her wish. Both of the guys undid their shorts and pulled out their cocks. At the sound of them undoing their clothes, Caitlyn's eyes shot open and she saw their dicks come into view. They, like Matt, were reasonably well endowed and her pussy responded to the sight of their pricks pointing at her. "Oh fuck yeah," she said, "stroke those big cocks for me. Cum all over me like I know you want to." Tyler and Darren wasted no time and began stroking their cocks, pointing them at Caitlyn's beautiful face. She continued to play with her tits, but slipped her right hand down into the waist and of her shorts. She began to massage her clit with fast, circular motions which sent waves of pleasure through her body. She moaned, fighting between the urge to shut her eyes and lose herself in the feelings and wanting to watch as her friends jacked off, looking at her. It excited her that they all wanted her. Three gorgeous guys, her closest friends, lusting after her, all wanting their way inside of her. She wasn't lost in the absurdity of the situation though. Most sexual relationships begin with a kiss, some fondling, maybe oral sex, followed by vaginal sex or some variation. Kinkier explorations came later, but this was different. She was presenting herself to her friends as jack off material, like a girl in a magazine or porno that they used as visual stimulation while they came. She knew that they masturbated to her, at least she thought they did. They damn well better have cum thinking about her. She knew she had many times thinking about one, two or even all three of them using her and her body for sexual gratification. She tried to be sexy around them, going braless and wearing skimpier clothing. She liked teasing them and hopefully turning them on. It made her pussy sopping wet and in need of satisfaction as soon as she was alone, thinking of their hard cocks penetrating her young body. She was moaning non-stop as her fingers massaged her sensitive clit and teased her nipples. She opened her eyes and looked at her friends stroking their cocks. She bit her lip, lost in the lust. She felt herself building toward an orgasm, just the start, but she could feel it was going to be a strong one. "Please cum for me boys, cover me with it," she pleaded, her fingers teasing her closer. "Tell me how much you want to fuck me." "I want to fuck you so bad," said Tyler, his hand flying up and down his shaft. "Me too," said Darren who was breathing heavy and grunting loudly. Caitlyn felt a hand reach around and start playing with her other tit, caressing the firm mound and twisting her other nipple. Matt had knelt down behind her and was helping her fondle herself. He took his other hand down and began to play with her ass. "You fuckers better tell me before you nut 'cause I don't want that shit on me," he said to the two guys stroking their cocks a foot away from Caitlyn's face. He then tilted his head towards Caitlyn's ear and said, "You going to be our little fuck toy slut from now on? Let us fuck you any time we want?" "Oh God," she shuddered, "Yes, YES, fuck me whenever you all want, anyway you want. Fuck! I've wanted you all for so long." Her body was shaking as she brought herself closer to orgasm. "I'm gonna cum dude," said Darren who stepped closer to Caitlyn. Matt removed his hands from her body and moved away. "Yes, please, fuck, cum on my face," she panted breathlessly. Darren growled something fierce and several spurts of hot cum crashed against her face. "Oh my God, yes," she screamed. With her mouth open, she received some of his load in her mouth and she greedily swallowed it down and began licking her lips for any remnants. "Oh fuck, I'm gonna cum too," said Tyler. "Oh, cum in my mouth and on my face," gasped Caitlyn whose hand was furiously rubbing at her clit. She opened her mouth and stuck out her tongue right as Tyler unloaded onto her face and tongue. She swallowed it down, moaning as she did. Her face was covered in globs of hot semen and all three of the guys watched as she closed her eyes and masturbated in front of them. Her body was convulsing and shuddering and her breathing was becoming more ragged and shallow. They stuffed their cocks back into their pants and watched as her supple, young body writhed in front of them. She began to shake more, and quick flutters of sound escaped her gasping mouth. "Oh my god, oh my god, oh my god," she said over and over, building a tiny bit louder each time. Then she seemed to stop breathing, no sound coming from her as she tensed up until she finally screamed out and her body convulsed uncontrollably. She rocked back and forth between and sitting and elevated kneeling position as her orgasm coursed through her body. It seemed to go on forever in their eyes, thirty seconds, maybe longer, before she finished riding it through to completion. She then allowed herself to fall backwards onto the ground and catch her breath as she laid topless, legs spread with her hand still in her shorts and her glistening breasts rising and falling from her breathing. She opened her eyes and looked up at her three friends. They were all looking at her, taking in her naked body. She stared at them for a second and then began laughing. "Holy shit, that was awesome!" she exclaimed. She withdrew her hand from her shorts and laid them both on her flat stomach. "That was so fucking hot!" "I can't believe we just did that," said Darren. "I can't believe we never did it before," said Caitlyn. She let out a long, satisfied exhale and a content smile spread across her face again. With her eyes closed she said, "You boys taste so fucking good," and then started giggling almost uncontrollably. This sparked them to start laughing with her. "So, can a girl get a hand getting to her feet or what," she said and then reopened her eyes. The guys immediately reached their hands down, taking her hands into theirs and pulled her up. "Thank you boys. Give me a moment, let me go clean up and I'll be right back," she said. She walked out of the room and they guys started talking about what had just happened. Matt explained to them about his time with Caitlyn and what had sparked all of this. "So that's how you knew she'd be down with this," said Tyler. "Yep, it was," he paused, "loosely planned," he laughed. "Well, how was she?" asked Darren. From behind them, they heard, "Why don't you boys find out for yourselves?" They turned around to see Caitlyn in the doorway, completely nude. She was standing with her weight primarily on her right leg with her hip cocked out to the side and her hands clasped behind her back. She had a look of mischief in her eyes and she was slowly biting her lower lip. To be continued...