First Time for Everything (Patreon)

Since there was a three way tie in the poll I decided to write a second story for this week. But I kept it deliberately shorter and more sex focused so I wouldn't run wild with it and risk not actually finished before the month was over lol. I hope you guys enjoy!

“This is perfect!” Gwen exclaimed.

“Yeah it's great!” Kevin agreed.

The young couple surveyed their unexpectedly picturesque little hideaway, identical smiles spreading across their faces. Having just snuck away from their friends and family for a little private time finding a completely secluded and entirely empty stretch of beach was fantastic. Finding it right as the sun was beginning to set and the sky was a brilliant explosion of oranges and purples was perfect. They stepped onto the warm sand, took one look at each other, and it was all over. Throwing the towel they'd brought along onto the ground without a second thought Gwen and Kevin were all over each other like wild animals. Her lips met his and they practically dropped into the sand. Or more accurately she pushed him down and straddled his waist. Immediately removing her blue bikini top and tossing it aside Gwen pressed her modest, freckle covered breasts against his chest. She moaned into his kiss and shivered as something hard rose to meet her already sodden bikini bottoms. While she busily grinded against his erection and ran her fingers through his hair Kevin was grabbing two nice handfuls of her firm bubble butt. His fingers slipped beneath the fabric to grope and squeeze her trembling skin. It was clear where his priorities lay as he started to thrust upwards against her sex at the same time she pressed herself down against this bulge. Although she couldn't exactly fault him for his eagerness. They were absolutely dying to be together now that both of them had turned eighteen. With the possible issues of legality now fully behind them they were able to fuck like rabbits as often as they wanted. Which was exactly what they planned to do from that point onward.

“I think I forgot the condoms.” Kevin groaned, suddenly breaking their kiss to stare at her warm green eyes, “Should I go back and get them?”

“Not on your life!” She moaned. Tossing her bright orange hair out of her face she kissed his neck several times in quick succession, “You're not gonna need them anyways!”

“What d'you mean?” Although his voice was noticeably distracted she knew he wasn't going to let such a juicy hint go by unremarked upon, “Why won't I—”

Interrupting him with another kiss Gwen eventually pulled back and sat up straight. Slowly and purposefully rubbing her ass against his cock she bit her lip and asked, “Think about it for a second . . . think nice and hard . . .”

Kevin started to open his mouth but no sound came out as he stared at her with an awestruck expression, “Seriously?”

“Mmhmmm!”

“But I thought you—”

“I changed my mind.” She cooed, “Now shut up and stop protesting. Before I change it again!”

“O-okay!”

Sliding backwards and hooking her fingers into the waist of his trunks Gwen yanked down her boyfriend's swim wear. His thick cock immediately sprang to attention and she giggled at the sight. The last time he'd been this hard was the night they'd first said 'I love you'. It was quite comical to see what got him to such a degree. She bent down and grabbed the base with both hands while wrapping her lips around the tip. Lacking any sort of lubrication she'd have to make sure he was good and prepared before they went any further. Luckily for both of them she never passed on a chance to go down on him so this was a rather enjoyable little prelude for the both of them. Kevin immediately groaned as the familiar sensation of her warm mouth and skillful tongue washed over him. He managed to watch her slide all the way down to the base as her hands flattened against his thighs and her eyes shut. But when she started pulling back the pleasure was too much for him to handle and he fell back against the sand with another moan. Gwen brushed some of the hair from her face and let out a nice, wet slurp upon reaching the tip. For a moment her tongue darted out to slide across the neck of his shaft but it quickly vanished behind her lips. Actively fighting the instinct to keep going like usual she bobbed up and down his prick a few more times in the sloppiest way she could. By the time she pulled back his length was dripping in saliva and about as perfectly lubed up as could be. So without a word she pulled away and moved beside him.

Although he felt her doing something next to him Kevin was still just a little too dazed by what was happening to really process it all. His shaft twitched in the cool air for several seconds until he found the strength to sit up. Upon doing so he found Gwen smiling at him on all fours with the towel they'd brought stretched out beneath her. Quickly seeing the eager glint in her eyes and the seductive sway of her hips he scrambled to his feet. Only to kneel behind her and suck in a breath as he stared down at her perky little ass. It'd always been one of her best features, excluding those like her intelligence and personality, so finally getting to do more than spank and ogle it was kind of a dream come true. So much of one he couldn't help but bring a hand down on her partially exposed cheek. Gwen let out a small yelp as he spanked her ass, both buttocks jiggling pleasantly from the impact. When she looked back at him he offered an apologetic shrug. She responded by pushing her ass towards him and arching an eyebrow. He gave her a look of pure adoration and playfully swatted her other cheek. She tensed and flinched away from him for a moment as ripples of pleasure flickered through her. Although she'd been turned on pretty much since the moment they decided to sneak off her pussy was practically overflowing at this point. Torn between the desire to keep getting spanked and the need to feel his cock inside her she gave him perhaps the most arousing expression she could give. A combination of love, lust, and longing all mixed into an open mouthed, narrow eyed stare. As soon as he saw it Kevin reached out and tugged her bikini bottoms down in one quick movement. They slid down to her knees and were quickly forgotten by both teenagers as the excitement of what came next overtook them.

“Are you sure about this?” Kevin asked as he rested one hand on her ass while the other grabbed his cock, “We don't have to do it if you're having second thoughts or anything.”

“Kevin,” Gwen said in a breathless voice, “I love you. I love how caring you are. It's one of the best things about you. But right now you need to shut up and stick your cock in my ass.”

He could only laugh at her vulgarity and shrug his shoulders. Who was he to argue with Gwen? Gently spreading apart her buttocks with one hand Kevin stared down at the cutely puckered and unassuming little hole clenched mere inches from his cock. She smirked at the intense look on his face, without the context of everything else his expression was like that of a surgeon about to perform a dangerous surgery. As he slowly pushed forward and she felt his tip press against her ass her focus shifted. With a quiet exhale she did her best to calm her inexplicably frazzled nerves. Despite the practice she'd done before this and the confidence that'd led to this point she was still more than a little nervous in the actual moment. Kevin definitely had more girth than a couple of her fingers and part of her wasn't sure she could really take all of him. But the moment of truth arrived before her misgivings could go beyond thought at the moment he started to push much of them melted away. Her body shivered and she inadvertently tensed as the slick head of his cock was momentarily rebuffed. Wisely continuing to push forward at the same gentle pace Kevin didn't let up and little by little Gwen's ass started to relax enough for him to find purchase. She let out the breath she didn't realize she'd been holding and, seemingly counter intuitively, pushed out instead of pulling in.

With that simple but immensely helpful act he was able to slid an inch or so into her amazingly tight ass. Both of them moaned with identical pleasure, neither able to believe how good it already felt. Even if they stopped right there and didn't do anything else the unexpected satisfaction and thrill of the moment was enough to make the entire thing a success. Thankfully Kevin had no intention of stopping there and Gwen never would have let him anyways. She felt his strong hands slide around her waist and her body trembled a little. A soft whimper spilled from her lips as he resumed pushing forward, his movements even more tender than before. Her arms started to buckle beneath her as the exertion of keeping them steady proved more difficult with every centimeter of cock that entered her ass. It was a feeling both familiar and alien. Juices seeped out of her untouched pussy and the closer he came to burying his full length inside her the wetter she got. There was something intensely naughty about letting him take her anal virginity. Their actual first time together had been a sweet, fumbling mess but this was so much more . . . deliberate. They knew exactly what they were doing and she could absolutely feel that in the way he moved. It might have been new territory in many ways but the undoubtedly careful way in which he slid inside her wasn't. There was something reassuring in that even as Gwen looked forward to the point where he'd start really giving it to her.

“See?” She finally panted as his hips came to rest against her buttocks, “T-told you?”

“Oh yeah?” He asked, “What did you tell me?”

“I—Ohhhhhhhhhh!”

Bending over her and sliding one hand between her thighs he pressed two fingers against her clit before she could give him whatever snappy retort she planned. The instant burst of pleasure from his unexpected touch cut short any desire to keep talking. For both of them. The feeling of her inner walls trembling around his cock was simply too amazing. He started slowly rubbing her sensitive bud, his back straightening as much as possible so he could gradually pull out at the same time. Gwen squirmed and moaned as she felt him scraping against her during his exit. Her body seemed unable to process that sensation and the immensely enjoyable touch of his fingers against her clit. Instead of the two feelings overlapping with one another and melding into a beautiful storm they vied for her attention like bratty children. One would gain the upper hand and her mind would focus entirely on it for a few seconds until the other suddenly surged into prominence. Usually because some small but enormous feeling change would occur. Like when he stopped pulling back and instead began to thrust forward once more. Just about the entire time he was sliding back in she barely registered his digits teasing her clit. But then when came to a stop all that unnoticed bliss came screaming to the forefront along with a small deluge of fluids and plenty of moans from each of them. It was no surprise then when he swiftly found a steady rhythm that kept them both in such a state, his hips bouncing against her ass at a gently increasing pace while his fingers matched the tempo. Nor was it a surprise that after a few minutes of such an experience Gwen was perched on the edge of a nice, quivering orgasm.

While not as big as what he'd caused when his face was buried between her thighs the climax looming over her head was still one that made her stomach do flips and her heart skip a beat. About the only thing she was able to do before it washed over her was allow her arms to crumple and her face to rest against them. She'd have to rely on his firm grip to keep her upright as ecstasy washed over her and conscious thought faded into nothingness. Her ass clamped down around him so tightly it slowed him down to a crawl, the spasms coursing through her making Kevin moan almost as loudly as his girlfriend. If her pussy was incredible her asshole was unbelievable. He wanted to start thrusting like he did when they were going absolutely wild, the urge almost overwhelming in the face of her obvious satisfaction. Few things made him harder than hearing her moan like that because of him. In fact keeping her going was pretty much his sole motivation for continuing to move as fast as he possibly could. Any thought to his own state was a far off concept despite how large it was beginning to loom over him. And as it so often did her orgasm transitioned rather nicely into his almost faster than either of them could react.

“Oh God!” He groaned.

Gwen giggled and looked back at him, a knowing grin spread across her face. Both surprised and flattered by how quickly he'd reached orgasm she couldn't help but ease him a bit, “Already?” She asked, “I was just starting to enjoy myself!”

Gritting his teeth and moaning again Kevin thrusted a bit harder and a bit faster. He barely heard her teasing over his own pleasure. Never in a million years had he expected her to do something as kinky as anal and that, more than just about anything, was the source of his rapidly draining endurance. As much as he wanted to keep going and give her another orgasm such a feat was well beyond him. Her ass was just too tight and too wonderful. But as he built to a frenzied crescendo of wild thrusts and breathless groans an idea popped into Gwen's head. Although she was more than happy to let him finish inside her as a final little treat there was something even more fun they could do. After a few more seconds of thoroughly enjoyable sex she suddenly and wordlessly pulled forward. Too focused on trying to last as long as possible Kevin didn't realize what was happening until his cock was suddenly emerging from her tight little ass. Although the mild discomfort of such an abrupt ending certainly wasn't welcome as she rolled onto her back and slid towards him Gwen was all too happy with her choice. She grabbed his shaft with both hands and madly stroked his cock while sitting up and offering a wild grin. He looked down at her with a mixture of surprise and disbelief, unable to process what was happening. When she slowly closed her eyes and licked her lips he realized what she was finally letting him do. A split second before cum erupted out of his tip to streak across her blushing face.

Thicker and more copious than she'd experienced in quite a while, or perhaps even ever, Gwen was quite taken aback by how potent his climax was. In just a single spurt he managed to cover a good portion of her face and force shut at least one of her eyes. Another followed soon after to land across an untouched stretch of blushing skin and suddenly she couldn't open either eye. Her lips were under no such limitation so she gladly parted them in time for a third jet to land right across them. The pungent smell of jizz filled her nostrils while rivulets of it started dripping down her cheeks and soaking into her hair. As Kevin groaned load after creamy load was unleashed on her face. Each one was met with a little shiver and a slight widening of her smile. Being unable to see them coming she reflexively jumped ever so slightly as they landed but under the circumstances she could easily ignore her usual dislike of surprises.  For close to thirty second she lay beneath him stroking his dick and milking him for every drop he had to give. And when there was nothing left she licked what little cum she could off her lips and moaned up at him. Laying there, drenched in her man's cum with a freshly fucked asshole Gwen had never felt closer to Kevin. Had she been able to open her eyes the look on his face would've told her how he felt the exact same way. It was quickly communicated when his hand gently brushed against her cheek, purposefully touching one of the few places not plastered with jizz.

“The showers are kinda far from here . . .” He said.

“Yeah . . .” She laughed, “Can you help me down to the water?”

“Of course.” Moving back and tucking his cock into his trunks he added, “Do you wanna put your bikini top back on?”

“We can worry about that after I've rinsed off my face.”

“Right. 

She took his hand and let him pull her to her feet. Before she could bend down to do it Kevin pulled up her bikini bottoms and she smiled at his kind gesture, “I love you Kevin.”

“I love you too Gwen.”