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  • Cumming on Caitlyn Ch. 01

Cumming on Caitlyn Ch. 01

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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.

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