There's a First Time for Everything

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Yes! It feels so fucking good to admit it, I love fucking you so much! I love you! I have for a while, I wish it was something I could have been woman enough to admit then, but I love it, I love you, and your cock, your cock feels so fucking amazing!!!" Sophie squealed, reaching up and grabbing her tits, pinching her nipples and groaning as she fucked him wildly.

"You're so beautiful... I should never have let anything stop me from pursuing you, all that nonsense..." Von groaned in response.

"Grab my ass!" Sophie commanded.

Von slid his big, strong hands to grab her ass, better helping her ride him. "Like that?"

"Like that!" she squealed, laughing and groaning at once. "As soon as I figured this out about myself, I should've come right to you... we could have been doing this for months, we could have been fucking each other's brains out instead of holding back!"

He found that image she painted to be a seductive one, making him regret that they hadn't done this sooner.

Still, they could always try to make the most of it. "We'll have to make up for lost time... as often as we can..."

"We should tell our parents that we're boyfriend and girlfriend!" Sophie groaned. "Then they won't have a way of stopping us..."

Von rather liked that thought. "We could... but we'd have to find ways of sneaking away from them... I think they'd like to keep an eye on us, wouldn't you?"

"Maybe... but that would be part of the fun... part of the *danger*," she moaned particularly loudly as he squeezed her ass. "But there are ample opportunities for all sorts of wicked fun in this town, and they trust us because we're their *good* kids... I think we shall find many a chance to do this..."

Von would have gone into detail about how much his mother watched him like a hawk whenever he wasn't at church, but he thought that might not be the best for this moment.

What did feel best in this moment, however, was a bit of a warning.

"I'm... uh... I'm feeling something again..." he groaned, fucking up into her, yet feeling that undeniable pressure building in his balls once more.

"Me too... your cock is hitting so many sensitive places... just a little longer... and you'll make me cum again..." Sophie moaned, reaching down with one hand to play with her clit while she wildly fucked him.

"Yes..." Von responded, unable to stop, but needing to be clear since he was well aware that he was fucking her without protection. "But shouldn't I pull out... shouldn't we..."

With a fiery look of lust that would have gotten any man to do anything, Sophie locked her eyes onto Von's and said in her sweet, commanding voice, "Cum in me... I want you to fucking cum in me... I *need* you to fucking cum in me... do it, Von, fucking do it... cum for me and make me cum... I want to feel your hot cum inside me... please..."

Common sense might have made him think on this moment a little longer, but common sense had left a long time ago.

"Alright," he replied, helping her fuck onto him as he held onto her ass. "Soon, it will be soon, keep going, please, I love it, I love it..."

"Yes, yes, yes, here it comes, here it comes, here it... YEEEEEEEEEESSSSSSSSSS FUUUUUUUUUUUCK!!!!!" Sophie cried out, her pussy spasming as she came again, her juices positively spurting out this time as her orgasm tore through her.

"Oh... FUCK!" Von roared, cumming deep inside of her with more of his pent up cum.

The overwhelming pleasure made it feel like it may have been even bigger than last time, though he imagined her clutching cunt milking him had something to do with that. Shot after shot went deep inside of her pussy, making each of them quiver and moan as he emptied into her, and they let pleasure consume them.

Soon, she was an utter mess, shaking and sweating and breathing heavily, her hair a mess as she looked down at him with faintly teary eyes. Von looked up at her with a nearly divine awe, happier than he ever knew it was possible to be, and certain he had never seen a more beautiful sight.

Finally, Sophie collapsed on top of him, giggling and kissing him repeatedly and whispering over and over how much she loved him. Von found this a sentiment that was very easy to return, as he kissed her back eagerly, embracing her and holding her close in his strong arms. They held like this for some time, lost in their own world, this bed now their own personal raft in a great sea of bliss.

"Alright, alright, I've left you two to your own devices as long as I can, because what you were doing there was fucking beautiful, but I cannot hold off any longer..."

This voice was accompanied by slow clapping, and to see where it was coming from, Sophie rolled off of Von and onto her back next to him, better allowing the both of them to see a now cum-free Rose standing in the doorway of the bathroom.

"Rose," Sophie said, casual, as if she hadn't just had the fuck of a lifetime.

In his surprise, Von was considerably blunter. "I feel kinda bad... I sorta forgot you were here..."

"Oh, I am certainly here," she replied, bounding toward the bed and jumping on between them, lying down on her stomach so she could better make her presence known. "I washed up some time ago, but it seemed that the two of you needed a moment alone to sort your feelings out... and clearly, I was right. It was rather beautiful, I must admit, watching you two sort that out... and then the sex! Ah, the sex! We should all be so lucky for our first times to be as beautiful as that, and you, Von, holy shit did you deliver marvelously! It took everything I had not to pry you two apart and fuck the living daylights out of each of you, but I was good! I stayed in my doorway and I touched myself and I might have cum twice watching the two of you."

"We were that good?" Von asked, impressed.

"You were... good," Rose responded, kissing first Von, then Sophie, playfully. "Nobody is amazing their first time, but you were good... I've seen some big black cocks in my time, but none that compare with yours..."

For emphasis, she reached down and gently stroked his softening cock, rubbing both his and Sophie's juices off of it and pressing it to her lips, sucking them both down luxuriantly.

Turning her attention to Sophie, she continued, "And you know that my lust for you has no bounds, and that I absolutely adore your body... but seeing the two of you together, professing your love, ah... that really pushed matters over the edge. Call me a softie, but that made me so wet..."

Sophie reached between her legs, making Rose squeal in surprise.

"She's right," Sophie said to Von, almost conspiratorial.

Von grinned. "Good to know we pleased you."

"And happy to be pleased, believe me!" Rose replied, running her fingers over Von's chest with one hand, while groping one of Sophie's tits with her other. "Now, given this profession of love, I don't want to step on any toes, especially since I respect that some of your ideas about relationships might be a bit more... traditional, Von Everett... but if it's not a problem, I think I'd really like to fuck both of you into oblivion soon, if you find that acceptable?"

In many ways, Von still had a number of traditional ideas flowing through his mind, but, as it was, this day had certainly become more than a little non-traditional, and he wasn't going to let his errant thoughts get in the way now.

"Go nuts," he replied, loving the way it made Rose smile so broadly it lit up her entire face.

"Thank you!" she said, leaning in to kiss him, before she climbed on top of Sophie.

Now, by this point, Von had had a passing familiarity with the fact that Sophie and Rose liked to fool around, and had taken some distinct glee watching them kissing as they sucked his cock, but he hadn't even in the darkest recesses of his recently opened mind considered what it might be like to see the two of them properly fuck, or how truly beautiful a sight it might be.

Rose and Sophie kissed hungrily, as if this were the first time they had seen each other in years, their hands all over one another as they groped and stroked each other, their hands finding each other's pussies as they fingered each other. It was a sight to behold and one that held him enraptured, watching the two of them pleasure each other almost as if they didn't have to think about it, as if each knew the other's body so well that they automatically knew where they needed to be touched to be given the greatest pleasure.

Though enjoying the show, Von also took notes, watching and learning and meaning to put what he'd seen to good use.

It was watching each of them like this where Von first watched the two of them make each other cum, panting and groaning, moaning and calling each other some truly nasty names that only seemed to help both of these beautiful girls get off even harder.

While he needed to recharge after each orgasm, it didn't seem like they were bound by quite as much in the way of physical limitations. Moments after they each made each other cum messily, Sophie rotated under Rose so that each of them had their mouths available for the other's pussy.

Again, this was something that Von never would have once considered possible in his life, but watching the two of them eat each other out simultaneously proved to be a painfully erotic sight. In no time at all, this image had brought his cock back to full strength, and before he knew what he was doing, he was stroking himself again as the two girls ate each other's pussies. Though they were well wrapped up in each other, this was a sight clearly not lost on Rose, who flashed Von a quick, hungry smile, before she buried her face back between Sophie's legs and the two girls brought each other to orgasm again.

Gingerly, and with shaky legs, Rose now climbed off of Sophie, her face glistening with the other girl's juices as it had once been covered in Von's.

On all fours and giggling profusely, Rose looked back at Sophie. "Now, while I understand the two of you are now boyfriend and girlfriend, and I wouldn't want to interfere with that in any way, I meant it when I said I wanted to fuck both of you. If there's no issue there, Sophie Cusack, my hot and wonderful friend, and you, Von Everett, one of the most gorgeous men I've seen in some time, I'd really love some of that glorious cock... would that be acceptable?"

Sophie and Von exchanged a glance, and a silent, knowing nod, before he answered, "That would be... quite enjoyable, I think..."

"Fantastic," Rose purred, turning around to better give a view of her ass and pussy to Von.

She flexed her ass at him, encouraging, and looked over her shoulder at his somewhat bewildered face. "This would be right about the time where you should be on your knees behind me, sliding that long, fat cock into my tight, sweet little cunt..."

This made Von's cock twitch, and while the position seemed unconventional to him, he wasn't going to complain. He got up on his knees behind her, letting his cock lead the way as Rose reached between her legs and grabbed hold of him, rubbing his head over her hot, wet lips.

"Only your pussy?" Sophie teased. "I would have thought you would have had him balls deep in your ass by now..."

Von raised an eyebrow at this.

Rose laughed. "Not this time... it's his first time, and I wouldn't want to scare him off..."

Groaning at the way she rubbed his cockhead against her most sensitive parts, Von couldn't help but look down at her flexing ass, and the tight-looking hole winking within. "People... people actually do that with their... ass? I thought that was just stories..."

Sophie and Rose looked at each other and exchanged a laugh.

"That is so cute..." Rose chuckled. "Oh, Von Everett... we have such sights to show you. But, later."

"And *butt* later," Sophie said, sharing her own giggle, before turning her attention to Von. "We both love a nice cock up our asses, but it's also a little more advanced... we'll get you used to fucking our pussies first... but another time maybe, yes, we can have fun with our asses. Believe me, they're *much* tighter than our pussies."

"Yours was very tight," Von said, disbelieving of what she had to say.

"And so is mine..." Rose said, lining up his cockhead so that it parted her lips. "And it's about time you found out... come on, Von Everett... fuck me... this little slut needs to be fucked hard..."

With little hesitation, and Sophie's lustful encouragement, Von pushed forward and slid his cock deep into Rose's pussy. While she wasn't *quite* as tight as Sophie, her pussy still gripped his cock tightly, pushing him and urging him forward until every inch of him was buried within her. This was not without some resistance, of course, and Rose's confident voice began to break with every passing inch until she was whimpering and begging him for everything he had, but once he was all the way in, Rose looked back at him again with that painfully confident smirk of hers and simply squeezed his cock with her cunt.

This began the second fuck of his life.

There was little of the intimacy that he had with Sophie with Rose, but she more than made up for this with enthusiasm. While Sophie was soft and curvy, Rose had the tight, fit body of an athlete, and demanded a workout to match from him. Though he was ostensibly in control, being the one vigorously thrusting into her, she was in clear, complete control of this coupling.

"That's it, fuck me, fuck me harder! Fuck, I love big cocks like this, always getting so deep, stretching me in all the best ways, and your cock was built for a cunt like mine... fuck me, fuck me, fuck me, fuck yes... yes, a girl could get used to treatment like this... I know you two might be a couple now, but please, be sure to bring him by whenever you can, yeah?" Rose said to Sophie, before turning her attention back to Von.

"I think what you two have is a lovely and wonderful thing, but don't think for a second that I won't take any opportunity I can get to get some of your cock... fuck, it's so fucking good, keep going, keep going, keep fucking me harder, make me a cummy little whore... make me your fucking little slut for that big, black cock... yes, yes, yes!" Rose moaned.

Eagerly, Sophie crawled up next to Von and Rose, getting up on her knees so she could kiss him. "Slap her ass. Hard. That'll get her going like you wouldn't believe..."

"If you say so..." Von grunted, taking one of his hands off of Rose's hips and raising it above her ass.

SMACK!

Rose yowled pleasurably, only fucking back against him harder. "Ooh... fuck, you two really know what I like... but you can do better than that, Von Everett? A big, strong man like you with such big, strong hands... my ass can take more punishment than that..."

She grinned back at him challengingly, and although everything he had ever learned about how to treat a woman told him not to do this, she was asking so nicely, and she did seem to enjoy herself so much...

SMACK!

SMACK!

SMACK!

Rose was yowling and crying out, her body shaking in pleasure as she continued fucking back against him hard, matched only now by his own increased pace. Von had completely turned himself over to this delicious fuck, pummeling her pussy with his cock as he continued going at her harder and harder.

Sophie, for her part, got on her back and slid beneath Rose, the two of them now rubbing up against each other and making out as Von fucked Rose on top of his new girlfriend. He could see and feel their hands all over each other, both Rose and Sophie fingering Rose's pussy as he fucked her, feeling another orgasm building from seemingly nowhere as he kept fucking in and out of her.

SMACK!

SMACK!

SMACK!

It was with the final impact of his hand on her ass that Rose cried out in ecstasy, her body shaking in orgasm as if she had been electrocuted as her pussy gushed on his cock and sprayed against his inner thighs.

Impressively, Von hadn't cum just yet, but he knew that when he did, he wanted to be looking Rose in the eyes. He pulled out of her, rolling her off of Sophie and onto her back, then slid back into Rose's pussy, thrusting into her as she looked up at him with wide, impressed eyes.

"Not bad, Von Everett..." she groaned as he picked up the pace once more. "But it would be even better if my legs were on your shoulders, I think... I am incredibly flexible, after all, one of the many benefits of being a reformed cheer-slut..."

Admittedly, in this position, Von didn't have the best idea of how this was actually supposed to work, but Rose knew what she wanted well enough. She pivoted her legs into his hands and guided them one at a time onto his shoulders, before encouraging him to lean into her. This position really allowed some truly deep penetration, and solid traction for him, letting him truly fuck her as hard as she wanted.

Sophie snuck in, offering her hands and mouth and tits to both of them, alternating between kissing each of them while reaching down to finger Rose's clit. While Rose and Von did their best to kiss through this contorted, intense fuck, with Sophie's nimble fingers on her pussy, and Von's deep penetration, there was no way that this was going to last long. With one last, loud cry, Rose came again even harder than the last time.

It was all too much for Von as her muscles massaged him, forcing out another loud, grunting orgasm. His pumping slowed, he sent shot after shot of cum deep into her pussy until he slowed, then stopped, pulling out of her and falling to his back on the bed, panting and sweating and feeling thoroughly spent, and even more thoroughly satisfied.

He laughed, smiling as he looked to the two girls.

"Fucking WOW!" Von declared, laughing proudly. "Is it always this good?"

Sophie crawled next to him, curling under the crook of one of his arms, which he wrapped around her comfortingly. "It's pretty nice if you've got good people to share it with."

Rose situated herself wrapped in his other arm, grinning a sly, satisfied smile. "Which in this town, thankfully, you are rarely at a lack of options for. Not that I'm not rooting for you two, because I am... you make a cute couple, and I wish you nothing but the best, but... still, you must know there is a lot of fun that can be had with more than just yours truly to join you."

"Oh, I know it..." Sophie purred, then giggling. "I can think of a few girls who would lose their minds for someone like you, Von, all sorts of new experiences we can treat you to..."

Von was still trying to wrap his mind around confronting his longtime religious hangups, having his longtime crush now happy to call herself his girlfriend, and the fact that he'd lost his virginity to her and one of her friends... it was a lot to take in, and the thought of bringing anyone else into the picture, or any new, intensely naughty experiences, was almost overwhelming.

Almost.

Looking down, he saw his cock twitching to life, a fact that hadn't been lost on Sophie and Rose.

"Well," Von said, taking a breath. "I guess there's a first time for everything."

***

(Author's Note 2: Writing these stories is something I do in my spare time for fun, so if you're enjoying this, please, please, please drop some stars, reviews, or shoot me some feedback, as these really keep me going. Though I may not always respond, I do love hearing from all of you and seeing that you're enjoying my works. It motivates me to continue writing more. You've all been wonderful and I can't thank you enough for all of your kind words and encouragement and yes, even the constructive criticisms!

Before I sign off, I've one last thing to say. It's been a rough few years, and in times like this, it becomes very easy to give in to anger and let that rule your life. I ask that, instead of letting anger run your life, take a breath, ask yourself if anger is really best in this moment, and if it isn't, try to consider putting some kindness out into the world instead. It's a rough world out there these days, and while that doesn't look like it will change anytime soon, it doesn't take much to make it just a little bit better. Please be good to yourselves, and to everyone else.)

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
14 Comments
JohnnyRebBBJohnnyRebBB8 days ago

Could you please show us a timeline chart for each of your series?

AnonymousAnonymous10 days ago

Not bad but it took really long to get to the point

AnonymousAnonymous7 months ago

Although a spin-off story, this one can also stand alone. It is a great story, well-written, with fascinating characters. The author handles the religious element with great tact and respect, and this really adds depth to the story. A joy to read, this story fully deserves a five stars rating.

DarellionDarellion7 months ago

Love it. Great series, better spin offs.

bourbononicebourbononice10 months ago

good read, lots of possibilities with this group, maybe von and Ryan can team up with the book club. 5 stars

Show More
Share this Story

Similar Stories

Senior Year Memories - Addison A hung nerd helps a busty cheerleader get revenge.in Erotic Couplings
Bosom Buddies Ch. 01 A nerd befriends the 5 hottest girls in school.in First Time
Comforting My Neighbor's Daughter I fuck my innocent neighbor when she comes to me for comfort.in Mature
That's What Friends Are For Justin's best friend Samantha will do anything for him. in First Time
Beauty and the Geek Ch. 01 The rumors were true; the geek was hung.in Erotic Couplings
More Stories