Sorry, this took so long. Again. But in case this helps: I got some interesting prompts lately and am plotting another story these days. Or rather a series of shorts... I'll see. It goes by the name "The Darkcup Chronicles" and I'm very excited to get started with that. I'll try to finish this first tho.

Hiccup

To Hiccup, everything is only a blur. His body and mind are at war with each other, the cold hatred he feels for Mona against the hot desire that's eating him alive. All he knows is that when someone grabs him by the shoulders and tears him away from the warm body beneath him, it hasn't been enough. She hasn't suffered enough and the need to cum is still ruling his every thought.

Like a wild animal, he fights the guards holding him and growls and hisses at them and tries to hump them when the burning need in his cock becomes too much again. He only stops when a hard slap hits his face, the pain enough to distract him.

"Look at what you've done! What a mess!" cuts Draga's harsh voice into his mind. "But she's dead now, nothing I can do about it. Guards, bring him into my rooms."

Hiccup's eyes dart to the limp body still lying on the bed and swallows. Draga is right, Mona is dead… Now it makes sense that she's stopped fighting him. The thought makes him sick. Has he really…?

He doesn't get the chance to keep thinking about that.

Rough hands pull him out of the room and soon there is no space in his mind to think about Mona anymore. The alcohol she gave him is still in him, heating his desire and making his head dizzy.

He's grateful when the guards throw him onto a hard, flat surface and he doesn't care when they shackle his arms and legs to the wooden construction beneath him. All he cares for is that the room stops spinning so much and the firm hand around his cock.

"More" he begs when the hand is too slow, the grip too light. He doesn't care anymore whether he's begging. "Please, I need more!"

"Oh, look at you, completely ruined," Draga purrs. Her hand moves even slower than before. "But that was to be expected with all the terror cum inside you and the booze Mona gave you. I have to thank you, you know? She was turning into an annoying brat, I'm actually glad you dealt with her for me. But I can't let my people know that, so you need punishment. Besides, I can't let you get away with that, you might think you can do so again one day. So, let's see…"

Her words leave a bad aftertaste in Hiccup's mind, but again he doesn't care much. Instead, he whines when her hand leaves him altogether. He yelps when the surface beneath him moves. Against his will, his legs part when the construction moves, leaving him open and vulnerable.

"W-what are you doing with me?" He expected her to make him fuck her again, but this seems different. It frightened him.

"Oh, you'll see," hums Draga while she steps between his spread legs. "You deserve a punishment for killing one of mine, but even though I expect you do not dare to work against my wishes ever again after all this, I still want you to enjoy it. To a degree at least. I certainly will."

He doesn't get the chance to respond and only gasps when he feels her hand at his ass. Feeling the Terror there at the beginning of all this madness was strange but this now is worse. She rubs over his rim and chuckles when he squirms in response. "Oh, you like that, don't you? I should have known. Maybe all this isn't even news to you." She goes on, rubbing a strange prickling oil over his hole, his balls, his cock. It makes him whine and throb even more, a constant teasing in addition to the raging fire inside him. It had been what, ten minutes since they found him? Fifteen? Too long without an orgasm and the need is already all-consuming again.

After some endless minutes, she does what he feared she would. Or hoped? He doesn't know anymore. He heard about it, even saw it a couple of times, with Tuff and Snot or when he happened on Gobber in his forge. But he never felt the desire to try himself. Now, however, he has no choice. He shrieks when she pushed two of her long fingers into him. It hurts, but thanks to the oil and his aroused state not as much as he feared. And then she hits something inside him, the same spot the Terror hit too, and it actually feels good. Amazing even. Like he will cum just from this small touch.

He doesn't though, at least not right away. It takes about a minute of Draga repeatedly pushing in and out of him and hitting that sweet spot until his body can't take any more.

He howls back arching when the climax tears through him without his cock even being touched and his cum lands all over him. "OH FUCK!"

"Yes, that's it. Good boy. Looks as if you like your prostate."

Hiccup again loses all sense of time when Draga goes on. She puts more fingers into him, then her whole hand, her fist rubbing deliciously over that sensitive spot inside him. It feels so good.

"No, don't stop, please," he whines when she eventually pulls out of him. Without her hand inside him, he feels strangely empty. He feels himself clench and wants her back inside him.

"Don't worry, I'm not done with you yet."

She steps past him and he catches sight of something that should frighten him. It certainly would have under normal circumstances. There are leather straps like he saw at Heather's and Fishlegs' once but the dildo that's attached to it is much bigger than what they used. His eyes widen when Draga steps back between his legs, the insanely big strap-on attached to her hips.

"Let's see how you like this, pet. It's still only training though."

And without much more preamble, she thrusts the monster dildo into his ass.

Hiccup screams as it stretches him beyond what he thought possible. It's too much, he's too full, can't think, can't breathe. It hurts. Then the uneven shapes drag along his insides and it feels good. He's caught between shock and pleasure.

Draga doesn't give him time to get used to this and directly pulls out only to thrust in again, deep. The pain is intense and his screams loud. But with every new thrust, it becomes more bearable. it's not that the pain lessens but that every time she hits his prostate intense pleasure surges through him. It mingles with the pain until he can't tell the sensations apart anymore. His legs, arms, and head shake and spasm uncontrollably as he cums again and without the manacles that hold him in place he certainly had hurt himself.

And Draga goes on and on and on. Whenever Hiccup catches sight of her leaning over him he feels disgusted at himself, at being degraded and humiliated like this. He is getting fucked by his enemy, not even for their pleasure but only for his and he enjoys is. But he also can't help it.

It is harder to cum from only this without her ever touching his cock but it feels so good, so intense. He relishes in the constant relief, certainly longer than any session with one of the girls before lasted. On and on she fucks him, possibly for over an hour, and her praises over how good he is for her, how surely everyone in their camp can hear his screams of pleasure, and how wonderfully ruined he looks cover him just like his cum.

A part of him wants this to never stop.

As always, comments are always welcome ;) Unless you're just here to tell me how sick I am. In that case, I can only wonder what brought you here in the first place 8-)