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!
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"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."
