Helping Hands

Chloe squirmed on the bullet inside her. Ollie had become such an expert teasing her with it, while keeping a couple fingers free on the same hand to caress her labia and her clitoris. She uselessly squirmed around on it, too horny to remain steady for even a moment. She was seconds away from her climax, from all her worries and stress melting away.

But she couldn't finish yet. Familiar terror set in, and Chloe thrashed her arms at Ollie, and launched herself up to a sitting position on her bed. The mighty pounding in her heart overtook any sensation of pleasure, and she stared at the door in maddening dread, while her warm sweat turned to glacial ice. The old wooden door, painted and repainted, but still showing signs of age, was a magnificent, original fixture of that old cottage. And sticking out, shimmering under glorious golden sunlight, a brass key calling to her. Chloe had lived in this house her whole life, and always forgot about that damn key.

"Relax, Honey Bun. I locked it." Ollie told her. He rose up next to her, and brushed her hair back over her shoulders. He ran a hand up her stomach to get a cheeky squeeze of her breasts before she noticed. Wearing that T-shirt during their play frustrated him to no end. Chloe shot him a sweet smile.

"Thanks." She sighed. The two laid back together. And Chloe felt her wetness. Her edge was already a forgotten dream. But her stress stubbornly remained and it felt a heavier burden than ever.

"I told you I locked it before we started. Did you forget?"

"...Yeah." Chloe blushed while she answered. But she hadn't forgotten; just a few seconds prior to that pseudo panic attack she remembered well that he had locked it. Chloe had struggled to cope with stress since she was little, and her best friend Ollie, oafish as he was, rarely helped to put her fears to rest. At least, since they turned eighteen the year prior, he had come up with one way to help her.

Chloe kept her eyes fixed on the prominent crack decorating an otherwise plain white ceiling. She could feel Ollie's eyes burning into her, but couldn't muster the courage to stare back into him and let their souls talk. He was conventionally handsome, for a teenager, with lush, vibrant brown hair styled with an expensive haircut.

To him, Chloe was the most beautiful girl in the world with golden hair and eyes the colour of the clearest oceans. With a perfect, busty body.

They began again, with Ollie slowly inserting the bullet into her wet pussy, and Chloe closing her hand around his meaty cock. Slowly stroking up and down on the shaft, Chloe cast her mind back to that first day where their relationship changed forever:

"Ollie! Get out!" She screamed when her best friend walked in on her changing. Smirking and taking a moment to admire her sexy body, even though she wore her underwear, Ollie closed the door and called out from the other side.

"I'm not sorry. You're looking good, 'Chloepatra'." He half-heartedly remarked. Chloe stomped up to the door and turned the key. The heavy bolts slammed into place burdened by Chloe's fury. Leaving her had against the key, she paused dead. And cursed herself for forgetting to lock the door when she knew Ollie was coming to pick her up. They were headed out for the day and she was already stressed out enough about the logistics of getting there and back again afterwards.

On his side of the door, Ollie gormlessly stared down at the tent he had pitched in his trousers, hardly concerned about what Chloe would say when she saw it. He had not the sense--nor had the shame--to hide the effect Chloe had on him from her innocent eyes.

"Gross..." She mewed when she opened the door.

"This is your fault, Babe. Better take responsibility."

"Fuck off." She thoughtlessly erupted. Hoping to backtrack, she checked over the stairs to make sure her parents were out of earshot. "Go to the bathroom and take care of it."

With no more convincing, Ollie turned and headed to the upstairs toilet. Not wanting to hear that, Chloe returned to her room, and sat staring into her small collection of makeup, unsure whether she had the fortitude to wear any that day.

She sat aimlessly rummaging for ten minutes before heading back to the bathroom.

"Ollie. What are you doing in there?" She asked in hush tones. "We need to get going."

"Sorry, Sweet Cheeks, but I'm a sixty minute man. So unless you want to lend me a hand--or two--this might take a while. I bet I'd cum real quick if you did it."

"Lend you a hand?! You pig!" She called out. Still, the clock was ticking, and she was a time bomb. In situations like that, Chloe was prone to stupid mistakes. The bomb went off, and the payload was too much stress for her to bear.

"Fine... Come to my bedroom." She conceded. A defeated Chloe dawdled back, and Ollie emerged to follow.

Inside the feminine room of Chloe's childhood, Ollie lay down on the bed wearing the hugest grin she'd ever seen from those pearly teeth.

"You're loving this, aren't you?" Chloe asked.

"Not at all. I'm about to be, though."

"Hurry up, get it out." She answered. Though Ollie had another sarcastic comment on his tongue, he chose not to spill it and not try his luck any further. He unzipped his trousers as asked, and made sure to squeeze as he grasped his cock. He made a show of revealing it to his best friend, making sure to point it upright and pull back his foreskin for the very best view he could offer.

"Impressive, huh?" Ollie asked.

"Is it?" Chloe genuinely begged. She had no clue whether this was big or small, or just average. Chloe had never watched porn in part thanks to the child filter her parents had on their router. And this was her very first sexual encounter.

Overcome by curiosity, the teen wasted no time reaching out for him, and she wrapped her dainty hand around his cock. In his embrace, it was a knife. But in hers, it was a mighty broadsword. A dribble of pre-cum wet his crown, and Chloe, lost in her own mind and without hesitation, ran her thumb over to it and spread it around. She jumped when she felt Ollie's hand guide hers.

"Whoa, sorry Lamb Chops. Didn't mean to spook you. Are you enjoying this that much?"

His question made Chloe sigh before she even considered it. Yet the question tumbled around in her head. She was enjoying herself, she realised. The way her heart pounded, the way her mouth hung open and the way her hand moved as if controlled by someone else all painted the image of a teen girl overcome by lust. But there was also the distinct pang of regret in her gut. To do this for a boy she wasn't dating made her feel easy and cheap. Her face twitched between emotions she had no time to sort through. She could only lean into one or the other. So she made the brave decision to let go of her worry, and enjoy this as Ollie wanted her to.

Chloe took hold of his shaft and began to stroke, overtaken with a trembling electricity.

For Ollie himself, this was the first time he felt someone else's hand around his cock. It was an awesome feeling, and he knew instantly that he wanted it again, if only Chloe could manage it.

Chloe remained on her knees, in between the gap of Ollie's open legs, in the perfect position to lean in and give his snake a kiss. But she didn't. There was no way she could force herself to go any further than this despite how her pussy now slobbered for more.

"How long is this supposed to take?" Chloe tore her eyes away from Ollie's impressive cock to his eyes. He stared at those full lips, softly pouted waiting for an answer. He couldn't take a huge smile off his face.

"It'll take all day if you go that slowly. Go faster."

"You're awfully bossy for someone getting a handjob. I don't want to hurt you."

"You won't." He encouraged. Chloe's hand shook left and right as she frantically rubbed up and down the length of his cock. Ollie made sure to put a show on for her, and let out breathy groans for her work. It did put a smile on Chloe's face. Having this effect on him made Chloe feel sexy, and that helped reduce her anxiety a little.

When Ollie finished all over his stomach, he smirked up at her and her face soured.

"Whatever you're going to say, just forget it."

"Little help cleaning it up? Come on, Foxy, you know you're dying for a taste."

"Not a chance. I have a box of tissues, clean up and then we really need to get going or we'll miss our train. We probably already need to run there now."

Somehow, Ollie talked Chloe into doing it again another day. And then another. And finally, her willpower was broken down enough that she let him return the favour, and from then on they frequently masturbated each other on her bed...

Digging herself back out of that daydream, Chloe smiled at Ollie. He was too casual sometimes. He didn't often know what to say to make her feel better when the everyday stress of life--that she felt unequipped to handle--began to weigh her down. But it was he who was responsible for their current relationship; friends with benefits, and Chloe felt so thankful that he was her best friend.

Something clearly ate him up inside. He pushed the bullet inside her a little deeper, and got an excited moan from her. So he pulled it back and let her regain her composure.

"Did you go on that date?" He asked.

"With Brad? Yeah." She answered.

"Alright... Can I ask if you... Nevermind."

"What are you so shy for? Just ask."

"Did you have sex with him?"

"I didn't want to. But he kind of expected it... It would have stressed me out too much to say no."

"Then you're not a virgin anymore?"

"No."

Their conversation died away, replaced by the keen, even needy moans rumbling from deep within Chloe. A deep flush painted her cheeks, and her eyes shut and her face twisted lewdly to engross Ollie in her rapture. He wanted to kiss her, to stuff his tongue in her mouth and explore it and love it and know it as he knew his own. He wanted her, he had never kept that a secret. And he couldn't break eye contact even as he saw a mischievous spark ignite inside his friend. She opened her eyes, glanced to him, and stopped stroking his dick.

Ollie wore plainly his disapproval, but Chloe sat up out of his grasp, and climbed onto her knees. She pulled off her T-shirt, revealing those incredible, plump breasts and laid down against Ollie, resting her tits on his arm. Her head rested on his shoulder. She continued stroking his cock, but he couldn't get the angle to pleasure her.

"Wanna hear about me and Brad?"

"You and another guy? Hard pass."

"I think you'll like it."

"No way. I'm not a damn cuck!"

"It's not like that, I promise. Please trust me." She hinted. There was a glint of unease in her eyes, and more than a hint on Ollie's raised lip. But in the warmth of her form, his chest eased.

"Okay." He gave in.

"Just... Don't laugh."

"Okay?" He repeated.

"There was something missing from it. He felt good, sure, but it kind of just felt like I was doing some painful exercises. Whatever 'magic' you're supposed to feel when you have sex, it wasn't there, if you know what I mean."

"My first time--with Molly--didn't feel that great either. But we had sex another couple times, until she got all jealous of you. It gets better."

"That's not it."

Chloe let out an exaggerated sigh, realising she'd have to bend over backwards to make him understand.

"Brad wasn't going to make me cum."

"His prick was too small, eh?"

"No! It's not that. But when he figured out that he wasn't doing it for me, he stopped and warmed me up with my toy. Then he fucked me after that and I came really hard. But I kind of... Cried out your name. I could tell Brad wasn't happy about it, but he chose not to call me out on it, and he finished himself inside me... But he hasn't called me since. And he won't answer my calls either."

"What a dick!" Ollie raged.

"I know, right?"

"No, if a girl does something you don't like you don't just ignore her. You ask her about it. You don't just ghost her!"

"I've never seen you this riled up."

"Of course I'm riled up. This is you we're talking about. You're my princess, Chloe, no joke. I won't ever let someone treat you like that."

"I'm your princess? I like that. Thanks, Ollie. But you do understand the irony of you complaining about other people's toxic behaviour, don't you?" She giggled.

"My toxic behaviour is endearing." He jested. "If it wasn't, you wouldn't be so addicted to my cock. I'll never do anything that makes you feel like shit. You know that."

"Yeah, I do."

The conversation risked dwindling again, but Ollie had plenty of fuel to keep the fire burning.

"So... You said Brad had a small dick, right?"

"I did not!"

"Was his cock bigger than mine?" As he asked, Ollie flexed his dick, drawing Chloe's full attention to it.

"Smaller."

"Knew it."

"It wasn't small!" She corrected, before he started thinking himself King of the Earth.

"Sorry to break it to you Angel, but I've ruined you for other men."

"Do you even listen to the actual shit that comes out of your mouth? You're not my boyfriend."

"That's what you think. But I'm counting down the days till I get you in a wedding dress."

"So you've mentioned eleventy million times before."

Chloe snuggled in to her friend, and Ollie took the opportunity to reach for her arse and take a squeeze. She didn't fight him. It felt nice to be wanted after being ignored by Brad.

"Hey, Ollie?"

"Yeah, Love Muffin?"

"Would you actually want to be with me? Even though I can be a bit of a wreck when I'm stressed?"

"A bit of a wreck? You're the last stop in Crazy Town. But yeah, I'd go out with you in a heartbeat if that's what you want."

Ollie was always so forwards, admitting his feelings like that came naturally to him. But Chloe, she couldn't do that, she knew she found him attractive and she wouldn't give up his friendship for all the riches on Earth. She loved him. But that was a far cry from being in love with him. And she wasn't sure whether she had those feelings for him, or whether she'd even be capable of recognising those feelings at all. Her mind then went back to sex. After her experience with Brad, she knew Ollie's cock was big. So big it was actually a little intimidating. She worried it would hurt her.

"Well... You're never going to see me in that wedding dress." She retorted, hoping to get the conversation back onto easier topics. But Ollie smirked, he wasn't going to let her off that easy.

"Tell you something, Bad Kitty, you and me getting together, it's inevitable. It'll happen, whether you like or not. One day, you're gonna fall madly in love with me."

"Shut up."

"Make me." He answered. In another reckless move, Chloe did. By placing her lips to his, she made him. Sharing a kiss did get both their hearts pounding. Chloe didn't seem particularly good at it. It wasn't her first kiss, but it wasn't far off. And it had to come to an end eventually. And the look Ollie gave her drew a heavy blush on her face from cheek to cheek.

"See? Inevitable."

Maybe it was, Chloe thought to herself. After all, he hadn't always masturbated her and she hadn't always done so for him. And now, even it was losing its power. She had long since wondered what his cum had tasted like, after he put the idea in her head that very first time. Her own tasted wonderful, and his looked like the thickest soup. Yes, she nodded firmly to incite possession of the spirit of confidence. This time she would take command, and she climbed over him, straddling his chest, facing away from him. He stared at that perfect arse, and she leaned down to get her mouth to his cock. And her pussy to his lips.

Plunging that thing down her throat, Chloe could never admit that she'd prepared for this moment, with a cucumber. Just admitting it to herself summoned an exasperated, silent laugh from her core. And she felt weak again. It was a memory best left forgotten.

"This it too big." She muttered, struggling to fit it in even after her practise.

"Well, it ain't a worm, I can't just cut it in half. If I could, I could help Brad with his pindick."

"It wasn't small!" Chloe laughed. "You better not go around saying he has a tiny dick or he'll have my head."

"Let him try. Gives me a reason to kick the shit out of him."

"Don't get all macho and go looking for a fight. You're not a gladiator, this isn't Ancient Rome, and I'm not going to get so turned on I soak my panties seeing you two rip each other to shreds."

"Well ain't that a shame. Think I'd win?"

"...I guess so."

Chloe was distracted from saying anything else when Ollie put his tongue to work. He'd clearly practised as well, though Chloe would be too nervous to ask how. His tongue probed her pussy he so desperately desired to claim as his own. He teased her virgin arsehole with her bullet, and Chloe was surprised to find she enjoyed it. It entangled her ever further into euphoria. He did not insert it into her, instead only massaging her with it, circling it around her hole and making her wish he would. Her eyes practically rolled back into her head, and her mind dulled as her orgasm approached. She lovingly ran her soft lips and warm throat up and down on Ollie's shaft, and massaged the tip of his cock with her tongue as they continued to pleasure each other.

His flurry of lashes against her most sensitive spots spurred the most erotic sounds from Chloe's lips and past the thick shaft filling her mouth. His tongue was her lifeline, to deny her an orgasm now would destroy her. His cock was straining in her mouth. She was expertly taking his whole shaft, and driving her nose down to his balls with each stroke. Neither could hide their true feelings, as they both began to hump the other. Ollie fucked Chloe's blissful throat and Chloe massaged her clitoris with Ollie's skilled tongue.

It seemed funny how often they reached this outcome: They often came at the same time, in perfect sync. And once again, they had reached their limits at the same time, and were due to cum again at the exact same moment. And yet, just as Chloe began to shiver, and hit that point of no return, Ollie pulled his tongue from her just briefly, even at the risk of ruining her critical orgasm.

"Don't make me cum yet."

"Huh?!" Chloe begged. But Ollie ignored her plea, he just buried his face into her cunt once more, and his tongue worked miracles, paralysing her with pleasure and sending her over that edge with more wonder than ever before. She couldn't hold herself close, even Ollie struggled to grab her fat arse and pull her in close and steady.

"Ollie!" She cried out through a prolonged climax. She thought it would never end. Nor did she want it to. Ollie wouldn't take his tongue off of her, until she had given him everything she could and then some. She collapsed against him, resting his big cock against her cheek. She kissed it softly and meekly, hoping to regain strength soon enough to finish him. She wasn't willing to give up her chance to taste his cum for the first time and get that little bit closer to becoming a woman.

"Why did you make me stop?" She begged so submissively.

Chloe rolled onto her side, lifting her leg from him. She made sure to keep his cock against her face, and rested her boobs on his leg this time. They stared deeply into each other's eyes.

"I didn't think it was fair that only Brad got to hear you scream my name."

"You..." Chloe realised she was too exhausted to come up with any sort of witty retort. So she just smiled at Ollie. And he smiled back.

"Don't stress yourself out. That's what I'm here for... Thanks, Sexy Thing. For everything you do for me."

But she didn't need to come up with a witty retort for that. She just kissed his cock again, and began to muster her strength.

"There's still something I need to do for you."