She moaned. The tentacle was violating her in a way she hadn’t concieved of, but it felt so good. “Ah! No! That’s not supposed to go there!”

The denser tips pleasuring her rear followed her muscular contractions - letting them subtly guide the intruder rather than forcing its way into her. As the first of those things slid into her rear - feeling less than a cock and more of a finger, it struck a particularly good pressure point that drew out a lewd moan from her.

Another inch slid into her as the tentacle continued their curious, slow inspection of the catch...

“Haaaaahhh! It’s in my ass! It feels too good! Get out of my ass or I’ll cum!”

Why not both at once? he thought to himself as she went from threatening, to pleading, to demanding, to squirming.

For the time being, he kept at it - more suckers latching onto her neck and stomach respectively as he worked to bring her ever closer to an orgasm, keeping a slow - steady pace as she inched towards a climax. Tough, leathery things lined with shifting, eager nodules rubbed against her nethers, massaging her quivering cunt as she reached her limit...

Just before she could find release, the tentacles pulled back from her. One more of those languid strokes would have sent her off the edge. Put to the edge of an orgasm, even the suckers tugging on her nipples eased off. Absolute stillness descended upon the cavern as he held her at the edge of a wild orgasm, the tip of his alien cock just barely touching the quaking lips of her cute little pussy as he held her still.

“No...no...get away...it feels too good....It’ll be my first time!”

Her pussy quivered in protest as she was allowed to reach the very precipice of pleasure - then denied. As she begged those tentacles to pull back and get away, they did so - leaving the nude schoolgirl tied up in a rather precarious position. It shifted as if beckoning the tentacle cock pressing its tapered tip to to enter her slick, tight depths but her desperate plea had been answered. They left her body screaming for more, while her mind was rushed with the sensation of betrayal that her body was being forced to endure.

When her thighs attempted to push down on the tentacle cock, the lengths coiled around her legs pushed her back up, letting her stew in the sensation of pleasure denied.

“I’m going to break....no...” She keeps crying. “Thank you..for not stealing my purity...”

That was when her own arousal, with no escape, turned against her. Drops of her virginal nectar dripped from her flushed nethers onto the shaft that was pressed against her. Her hips moving ever so slightly to jostle the large thing that would certainly break her body if he fucked her pussy with it.

That was when the oversized shaft split open into five prehensile segments that eagerly coiled around her thighs, pinning her in place as her hips desperately tried grinding against the thing. The core of the shaft, a prehensile and dexterous length, now teased her clit, while the things holding her loosened up, as if challenging her to seize her own pleasure by moving her legs so as to let the sinewy core of that cock make its way for the first time in her.

Her mind was on the verge of breaking as she cried. “Leave me...alone...”

The central cock shifted directions at the last minute, using her pussy to lubricate itself before shifting to press against her rear. The tapered cock that she bit the last time returned to its position below and pressed against her quivering pussy, using it to add more lubrication to her - but aside from the subtle, distant yet pleasurable buzz keeping her at the edge of her orgasm, it moved no further.

It was quite the punishing sensation - if she would move her hips forward...?

She ended up moving her hips forward in struggle...which led to the tentacle taking her virginity and robbed her of her purity forever. The overload of pleasure turned her brain to mush. “Huuuu....” Drool leaked from her lips as her eyes were vacant. She was babbling incoherently.

As she yielded and moved forward, the fleshy organ worked into her slick pussy, her hymen crumpling away as the slender 'cock' emerging from the main tentacle pressed against her nethers slid through her insanely tight lips thanks to its natural lubrication and the coating of her nectar she had kindly provided.

There you go. Now then... let's discuss your reward... he mused as the girl moaned out loud as her virginity was taken.

With that, the tentacles that had eased off to tease her returned with twice the eagerness. Once where they had been content to languidly tease her, now the things worked to pleasure her fully, toying with her erect nipples, groping her breasts and even fingering her rear as they converged on her. Even the smaller tendril teasing her ass returned, pushing the head an inch or so inside her rear...

The girl continued moaning until she fainted.

The tentacles prodded her, then slapped her rear to get any response. Nothing, but the sensory organs latched onto her neck still felt her breathe, the thud-thud of her singular heart.

"... oh. Had a little too much to drink, didn't you." he spoke as he pulled back the intruder in her ass.

If he left her here, she would surely starve to death before she found her way out. For the time being, he readjusted his grip on her body, cushioning the most strained parts with folded tentacles forming padding and waited until she woke up. These initial samples he took from her body proved promising, and while she was fainted away, he took the time to carefully inspect his catch...

His catch was truly lovely. Tiny breasts and a supple ass.