A/N: Dang, didn't realise it's been so long since i updated this lewd little story. My apologies on that front, may this Helena lewd appease thee~

Do enjoy~

Box of Wonders

Chapter 5: Helena

Helena was tired.

Part of that was due to a string of late nights followed by afternoon sorties or training sessions, part of that was just down to general fatigue. Thankfully she finally had some time off and didn't have anything planned for the next week, but she wasn't the type to just lay in bed and sleep, even when she was as exhausted as she was. More than that she was stressed out, something she knew fair well.

It was perhaps because of that fact that when she walked down the halls of the dormitory one early morning, Arizona – who was passing her by – stopped to chat.

''Are you okay Helena?''

''Mm. Just a little tired.'' Helena smiled up at the taller woman. ''You?''

Arizona smiled back. ''I'm doing okay. I'm not sure if you heard but I got a little... friend from Akashi. Apparently she's selling them to others too.''

Helena's curiosity was piqued. ''Little friend...?''

''It's a box of tentacles.'' Arizona explained shortly, her cheeks gaining some pinkness. ''It's for um... private uses. If you know what I mean.''

Helena didn't. Perhaps because of her fatigue it just didn't compute... not until a flustered Arizona looked around to make sure nobody was looking, then thrust her index finger through a hole made of her other index finger and thumb. ''O-Oh.''

''Mm.'' Arizona smiled bashfully, fidgeting. ''U-Um... if you want, you could borrow him, he's quite nice...? I-I've loaned him to some of the other girls before, so he's got experience...''

Helena's first instinct was to decline such an embarrassing offer, but the knowledge that others in the dorms had used him... it admittedly tempted her. She wasn't super active sexually, unlike some other ships who casually hooked up for flings whenever they felt like it, and she doubted she'd ever be that confident – if she was to be with a guy, she'd probably only do it if she had feelings for him, not for something casual. That said, a tentacle box wasn't a guy, and she was really pent up...

''...when can I borrow him?''

Arizona just smiled, ushering her back towards her room.

X-x-X

Morning came and went, and the hot summer afternoon inevitably followed.

''Hn... maybe this one? It looks a bit small though...''

Helena's soft murmurs could be heard clearly within the quiet comfort of her room, the cruiser's brow set into a soft frown and her lips pursed. She swapped her purple gaze between the two bikinis laid on the bed in front of her; one a deep blue and the other a more teal colour, both in similar designs that showed off lots of skin, though she was more troubled by the size of the tops; she wasn't keen on showing too much if possible, unlike St. Louis who didn't mind such things.

Given it was still summer the girls in the Eagle Union dormitory had decided to go to the beach in a big get-together sort of deal, and as such Helena had to pick out a swimsuit. Personally she would've preferred a one-piece swimsuit over a bikini, but St. Louis had gone through the effort of shopping for swimwear in both her size and preferred colours, and she didn't have the heart to tell her sister to go buy another one, just because she was picky.

''Hm... may as well try them on...'' Helena murmured to herself, sighing.

Reaching up Helena pinched the edges of her arm-length black gloves, tugging them down and peeling them off, tossing them onto the bed. Her dress came next, her lithe hands unfastening the straps behind her back before she reached down to the hem, tugging it up and over her head. The movement sent her blue hair fluttering and Helena ran a hand through it, idly pushing it down her back and leaving herself clad in her underwear. Her thigh-highs and garters went down only moments later, one foot at a time planted on the bed and allowing her to tug them off, soon leaving them neatly folded on the bed next to her two bikinis.

Unbeknownst to Helena the dormant box behind her wasn't so dormant after all; the lid opening a tiny bit and allowing the tentacles within to peek out, watching intently as Helena reached beneath her back and unclipped her white bra, shrugging it off. Bending forwards the curvaceous cruiser pulled her white panties down over her shapely ass, said underwear falling down her legs and ending around her feet, summarily stepped out of and leaving her naked.

''Hm... guess I'll try the blue one...'' Helena murmured to herself, picking up the blue bikini bottoms and stepping into them; tugging them up her waist and adjusting the pre-tied knots until it was a more comfortable fit.

Her bikini top came on next, taking a little longer as she tied the knot first and then turned her bikini top around, hefting her ample breasts into the cups. It took a little adjusting, tugging the cups a little to fit her boobs into them, and also forcing her to loosen the knot a little so it wasn't such so tight; but just barely she managed to make the bikini top fit. Though even then it was still quite snug, and left plenty of cleavage on display.

''Mn... St. Louis normally knows my measurements... maybe I grew again...?'' Helena mumbled to herself, adjusting her bikini top some more.

Unbeknownst to the cruiser the tentacles slowly began to emerge from the box, slithering through the air towards her. So busy fumbling with her top she didn't even realise until they were right behind her – and that was only because one tickled her waist, brushing against the side-tied knot.

Dubiously Helena tilted her head, turning to face the tentacles – and squeaked as she saw them.

A squeak that turned into a yelp when one tentacle went between her shoulder blades, stroking her flesh with its slick, sticky length – and then pulled on the back of her bikini top, easily forcing the loose knot undone just as another tentacle undid the one behind her neck, instantly causing her blue bikini top to go slack. Reacting swiftly Helena crossed her arms over her bust, holding her top to them and giving her some sense of modesty as she turned to face the tentacles.

''H-Hey! I didn't say you could come out ye- eek!'' Helena's attempt at scolding was cut short as two tentacles grabbed each of her arms, pulling them apart – causing her top to flutter onto the floor and make her bare her breasts to the dozen of tentacles hovering before her. ''A-Ah... wait, no, this is...''

A surprised moan tumbled out of her mouth as an eager tentacle went up between her breasts, two more pushing her tits together – allowing the lucky tentacle between her breasts to thrust itself up-and-down, practically giving itself a titfuck. The two tentacles pushing her breasts together soon curled around her plump chest, squeezing lightly and coaxing a soft whimper out of Helena, her cheeks darkening as she was molested by tentacles.

''Hey...'' Despite that the soft-spoken cruiser couldn't find it in her to resist. She was going to do this sort of thing this evening anyway, so she supposed she may as well go with it...

As if sensing that the tentacles grew more bold, one curling around her from behind – before it went between her legs. Helena gasped at the feeling, shivering as the sticky tentacle pressed itself flush against her ass and curled around, hugging her crotch snugly with the tip touching her belly-button. It rocked back-and-forth a little, rubbing itself against her clothed pussy, the fabric of her bikini bottoms shifting with the motions and rubbing against her pussy, the stimulation coaxing whimpers of arousal out of Helena.

The tentacle retreated after a moment, and the cruiser squeaked as it slithered up through the gap in her bikini bottoms, pushing and rubbing against her pussy. Helena squirmed at the feeling, anticipation quivering through her – and then at last the tentacle pushed forth, prying her folds apart and squirming itself into her womanhood. The feeling was novel and pulled a high-pitched mewl out of Helena, the cruiser tense as the sticky tentacle pushed itself in deeper and deeper, rubbing spots within her that a dildo never could.

Until soon it nuzzled against her cervix, the feeling making Helena arch her back with a shaky sigh. Getting penetrated so deeply whilst standing was definitely a new feeling though, a moan working its way out of her throat as the three tentacles toying with her breasts continued their lewd ministrations; squishing her plump breasts whilst one eagerly thrust itself up between them, the bulbous tip poking out from her cleavage and aimed at her face, the thought of getting a facial from a tentacle making her quiver.

''Ah... ah... ah...'' Helena panted as the tentacle in her pussy kept thrusting; making her subconsciously shift her legs open a little wider, making it easier for it to go in. ''Hey... hold on a sec, so I can move...''

The tentacles all paused, and then after a moment the one in her pussy withdrew – though the moment it escaped it pulled and tugged on her blue bikini bottoms, causing them to loosen and eventually fall off her hips, leaving her naked before the tentacles. Blushing a burning hue Helena twisted around, moaning as the tentacles playing with her chest retreated long enough for her to put her hands on the bed and bend herself over, presenting her ass to the tentacle mob.

Then with little hesitation one tentacle nuzzled her folds, and pushed back into her. Helena moaned at the suddenness of it, feeling no pain as the tentacle wormed its way into her womanhood and soon pushed against her cervix, rubbing up against it. She'd heard stories from Arizona about it penetrating cervix's; the thought a little scary, yet also shamefully arousing to the cruiser, her walls clamping tight around the tentacle as she grew tense with anticipation.

And then another tentacle came down, and whipped her ass.

''Ah~!'' Helena squeaked in surprise, cheeks burning as her butt stung. ''H-Hey, that- ah~!''

A loud smack echoed through her bedroom as the tentacle came back down against, slapping her curvy ass – any pain overwhelmed by the slick, sticky tentacle that pumped into her pussy, another one nuzzling her clit teasingly. Biting her bottom lip Helena endured the stimulation, but was unable to hold back the moans that bubbled up her throat. Doubly so when a tentacle slithered up her stomach and went back between her breasts, thrusting between her boobs as another two went back to groping and massaging her breasts.

Just as she was starting to get used to the sensation another curveball was thrown at her in the form of a tentacle curving around to her face, pushing against her lips. Mewling softly Helena parted her lips and accepted the tentacle into her mouth, sucking on the head and shivering as it wormed its way into her mouth, her tongue slapping and slithering over the bulbous tip before being pressed flat against the bottom of her mouth as it went in deeper, making her deep-throat it was a wet grunt.

''Mmph, ghk, ghk...'' Helena shut her eyes as she sucked on the tentacle, enjoying the one that was fucking her pussy at the same time.

Not to be left out the other tentacles smacked and slapped her ass with growing vigour, the whip-like strikes just hard enough to hurt and sting, but not enough to leave permanent marks. The mix of pleasure and pain wasn't one she thought she'd love, but with each successive smack Helena found herself sinking into shameful pleasure; moaning as she was spitroasted between the two tentacles.

The tentacles quickly began to pick up speed too. Thrusting back-and-forth they pistoned into her mouth and pussy with vigour, the latter being particularly vigorous in how it scraped her walls and pushed against her cervix. As if to reinforce that Helena felt another tentacle prod her folds – and she gasped as it pushed inside, the two tentacles stretching her insides apart as they fitted snugly within her, thrusting in sync. A third tentacle then teased her pussy lips before managing to wriggle itself in as well, sending powerful shudders through Helena's body as all three tentacles rammed into her womanhood, their combined girth far thicker than any cock.

''Mmph! Guh, Mmk!'' Helena moaned sluggishly around the tentacle in her mouth, feeling heat mount within her stomach. ''Mm...!''

As if sensing her rising pleasure the trio of tentacles plunged into her wet pussy faster, her arousal helping ease them into her and pound her cervix, hammering against it – until one inched deeper than it should have. It went deeper, wriggling, pushing; until soon it plunged into her womb, eliciting a muffled squeal from Helena as it penetrated her so very deeply. Her long legs buckled as the other two tentacles followed, all three of them thrusting and probing her birth canal, all whilst tentacles continued smacking her ass and fucking her breasts, the constant friction leaving her overloaded, and soon unable to hold back.

''Ah... guh, I, o-ohh...!'' Helena tensed, screwing her eyes shut. ''M-Mmph~!''

Pleasure hit her like a freight train, a powerful jerk flinching through her body and preluding the powerful muscle-weakening shudders that followed. Her walls pressed down tightly upon the three tentacles – triggering their own climax. The other tentacles also reached climax, bulges running down their dark green lengths until the one between her tits came first, shooting hot grey ropes of cum up her collarbone, her bent-over position meaning much of it fell short of hitting her and made a mess down on the bed beneath her. The tentacles squeezing her breasts fixed that by pushing her breasts together and aiming their heads into her cleavage; spewing their sticky load between her tits, making a mess between them.

The tentacle in her mouth pulled out just in time to spray its own cum across her face; ropes of grey cum hitting her cheeks, her forehead, across her nose and lips; it gave her a plentiful facial that left Helena moaning, flinching when she got some in her mouth. The tentacles spanking her reached their own orgasms; spraying ropes of cum across her bare back and ass, their hot cum streaking up her spine and between her shoulder blades, much of it getting on her butt.

Helena's attention was on the trio in her pussy, however; gasping as their cum flooded her womb. It was hot and sticky, splattering into her innermost parts in thick gushes, petering out... before the second tentacle came. Its delayed orgasm effectively gave her a second creampie; fresh cum spewing into her womb and coaxing a dumb moan out of Helena, her legs buckling.

And then the third tentacle came, pumping even more of its seed into her filled womb, so much cum filling her that it profusely seeped out of her sex, dribbling down her inner-thighs or dripping between her legs and hitting the hard wood floor with loud wet splats, the mere sound causing her knees to buckle with embarrassed bliss.

''A-Ah...'' Helena let her mouth hang over, panting. ''Hau...''

The tentacles all pulled out, eliciting a shiver from the cruiser, and she moaned as the ones between her breasts left too; causing plenty of cum to dribble down her stomach. Panting Helena leaned down and collapsed onto her side on the bed, uncaring that she felt some wetness beneath her sweaty body; she was going to clean up later anyway. However laid on her side she presented an ideal victim for the lascivious tentacles, a target they seized with vigour.

''M-Mm?'' Helena's cheeks burned as she felt a fresh tentacle nuzzle her pussy. ''Really...? You just came, but you're ready for more...?''

The tentacle eagerly nuzzled her folds, spreading them a little but putting no more than just the tip in. She was so sensitive however that even just the tip was enough to make Helena mewl, shivering as she debated whether to 'let' them. The tentacles did their best to convince her, one tentacle teasing her with just the tip whilst another rubbed her sore ass, coaxing her into going another round.

And with an embarrassed moan, Helena agreed, smiling shyly. ''Fine...''

Keeping her legs flush together she propped herself up on one hand, mewling as the tentacle teased her pussy lips – and then moaned as it pushed inside, claiming her. A second tentacle eagerly followed and corkscrewed around the first, both of the spiralling tentacles spearing into her womanhood and fucking a moan out of Helena, her slick insides seizing around the tendrils but failing to stop them from kissing her cervix once more, pushing and prodding against it.

Until with only a little trouble they wriggled their way through it, forcing a strained moan out of Helena – tempted, almost, to open her legs wide to make it a little easier. Yet there was something distinctly pleasurable about laying on her side and letting the two tentacles enter her like this, pumping their sticky, slippery lengths in-and-out of her tight hole. The other tentacles weren't willing to be left out either and one slithered up behind her, going not for her pussy but prodding her other hole-

-and Helena let out a hurriedly-stifled cry as it plunged into her asshole. It felt weird to have something in her ass and even more to feel it wriggle about inside her rear, the slick tentacle moving about and making her almost dizzy with the pleasure.

''Nn, ah, i-it feels good...'' Helena mewled out, unintentionally encouraging the tentacles.

Something she found out as two bud-tipped tentacles slithered through the air to her breasts, the buds opening up to reveal their inner petals to be covered in countless small tentacles – before they jerked forth and attached themselves to her nipples, eliciting a squeal of surprise from Helena as the hundreds of tiny tentacles licked and stroked at her sensitive tits, sending electric jolts rushing up and down her spine.

The tentacle fucking her ass wasn't alone though, a second, thicker one with ribbed bumps all along it prodding her hole too before forcing its way into her tight ass. Helena couldn't hope to hold back her stilted cry, a hand over her mouth the only thing stopping it from becoming a shriek as she felt all the little bumps along the tendril as it plunged into her asshole, her tensing muscles only enabling her to feel the little bumps all the more.

''Mn! Ah! Y-You're being a little roug- ooh~!''

Her loins ached pleasurably as the two tentacles in her pussy plunged up into her womb, thrusting back-and-forth rapidly and raking the walls of her baby chamber, making her see stars. Her breasts tingled and her ass ached as they too were assaulted by the tendrils, all of it happening so fast, so intensely that Helena couldn't even think straight, rapidly reducing to little more than a willing cum-dump for the tentacles. A fate they were happy to ensure.

''Mn! A-A-Ahh~! Y-Yes! Ye- hyaa~!''

Helena squealed as she finally reached her second orgasm, cumming from the intense, relentless sensations inside of her – and seconds later the two tentacles in her pussy came too, bulges travelling along their slender lengths and pouring their thick grey cum into her womb, replacing the cum inside it and causing all the excess to pour out around them. The tentacles in her ass came a few seconds later, the normal one shooting its grey load deep into her ass whilst the ribbed one swelled in size, intimately allowing her to feel the bumps rub against her insides, before it exploded its load into her depths; thick, profuse spurts making her back tense from the infusion of tentacle seed.

''A-Ahh...'' Helena trembled as the tentacles on her breasts released her nipples and slithered away - a shudder passing through her as the other tentacles pulled out as well, leaving her empty.

Empty, aside from their cum.

''G-Good boy...''

It would not be the last time Helena borrowed Arizona's tentacle box, that was for sure.

[END]