Sorry, this took so long. RL and motivation, you know... I will keep updating, not sure how often though.
As for your comments: There's going to be a HiccupxToothless scene later on. Not sure about the other dragons though. I'll think about it. And I can easily build in a flashback chapter for Astrid before she got led to Hiccup, I even already know where :)
Hiccup can't say anything. The look of hurt and betrayal in Heather's eyes is more than he can bear. Her expression turns angry and she makes a step toward him, but he doesn't shy back. On the one hand, he's not afraid of what she might do. Whatever it would be, he deserved it! And on the other hand…
"Hey! Behave, slut!" Mona sneers and pulls at the chains around Heather's neck. She stumbles backward and Hiccup looks away from her. He doesn't want to see the tears in her eyes. Heather is strong, so unbelievably strong, but these people are about to break her. And they used him to do so.
His eyes land on Ruff instead, and in a way, her surprised expression is even worse. She doesn't look angry, not in the least. Of course, she enjoyed their encounter after all, and that makes it so much worse. Not just that he's raped a friend, now it felt even more like cheating. Because it was Ruffnut, and they've both enjoyed it…
He's wanted to apologize in any way, mouth a sorry toward those women he's raped in his cum-induced frenzy. But now, he can't say anything. There is no apology…
Lost in self-loathing, he drops his head.
Lisa and the other two lead them on and there is nothing he can do. He still feels their burning gazes on him, but he doesn't dare to look up again and keeps his eyes on the ground instead. He feels his cock filling out again, the Terror-cum working inside him, but for once it is barely more than a low burning. The shame about what he's done is too strong.
He barely registers as Farina and Mona lead their prisoners into another barrack and return soon after without them. He barely registers how they lead him on to another building, taller and more stable. And he barely registers how they lead him into a big room inside and lay him down on a gigantic bed. Giggling, they change his metal manacle against leather cuffs and tie his hands and feet to the corners of the bed, but even then he barely reacts.
What does it matter anymore?
He can't fight them and is completely at their mercy. They already made him do the worst he can think of. Whatever they do now, it doesn't matter anymore.
It takes him a while to notice that what they actually do is leaving him alone. As far as he can see, immobile as he is, the room is empty. And it stays empty. Hiccup doesn't know how long he lays there while nothing happens. Minutes pass while he embraces the hopelessness of his situation. More minutes pass and drag on as the hopelessness turns to apathy. Once again, the need in his groins has grown to a raging fire but there is nothing he can do about it. Maybe he screams, maybe he begs, but it doesn't register in his mind. There is no one around and after a while, he gives up. He gets lost in his burning body, drowns in the pain and need to cum with no hope of release.
It is pure agony, just burning darkness. His body is shaking, spasming, but he doesn't notice. After a while, even the shame over what he did to Ruff and Heather fades and he begins to wish he could go back to those small rooms and fuck another woman, any woman… anyone, if only the pain would go away.
The moment something hot and smooth closes around his cock is pure salvation. He thrusts up into whatever it is and it only takes a second or two until he cums, howling, and hot drops splatter on his belly. He's weeping in gratitude and murmurs low 'thank you's to whoever sits above him. Slowly, his vision returns and he sees a waterfall of golden hair and a pair of sparkling blue eyes.
Astrid!
Astrid is here to save him, just like she always does. He grins like an idiot and babbles countless 'I love you's toward her. Somehow, she must have escaped, must have found him. She's here, and now everything will be-
"Aww, listen to him. Isn't he the cutest toy we ever had?"
That is not Astrid's voice!
"Yes, yes, you've said it often enough. Now, get on with it, or I'll take him first after all."
Hiccup groans as realization dawns on him. His tormentors are back. It is not Astrid sitting on his lap and lifting herself to take him in right now. It is not Astrid who moans lasciviously as he fills her. And it is not Astrid who mistakes his hopeless groan in desperation as a noise of pleasure.
"Yes, dragon boy, this feels good, doesn't it?" Farina moans, and Hiccup shakes and sobs in disappointment. A great part of him doesn't want this anymore. He wants to deny the pleasure he feels as the blonde girl bounces up and down his cock, wants to deny how good it feels and how much he needs it. But he can't fight it for long.
Still sobbing, he spills into her as he cums. Farina presses down to take in all he has to give but keeps moving only seconds later. She's persistent, makes him cum five more times while she climaxes twice, before she slumps down on his sweaty chest, panting.
"Wow, now that was even better than I imagined," she coos, caressing his heaving chest.
Hiccup doesn't answer. There is nothing he wants to say and even if, he can't. His mind is spaced out, high on post-orgasmic bliss and disgust alike. His whole body is raw and hurting, it feels dry in so many ways.
"Nothing to say, huh? Ah, that's alright. Rest a bit, the night is still long."
Giggling, Farina climbs off him and joins her friends around a low table. Hiccup doesn't remember whether it had been here before or whether they'd brought it here, it doesn't matter either. All that matters right now is the food on top of it. There's meat, soft bread, and fruits, along with decanters filled with what looks like water and wine.
Suddenly, Hiccup realizes how hungry and thirsty he is. He doesn't even remember when he's eaten or drunk the last time, and the activities of the last… what… two hours? Had only worn him out further. With the burning in his groins quieted for now, there's another burning that makes itself noticeable. His burning throat.
"Water…" he croaks, eyes fixed on the clear liquid. "Give me… water…"
One of the girls, Lisa, turns her head in his direction and quirks an eyebrow. "Did you say something?"
"Water…" he tries again. "Please…"
She blinks, then fills a glass with wine and saunters over to where he lays. "Try again."
Hiccup's eyes are glued to the sloshing liquid.
"Please, let me drink… Lisa... plea-"
No, no, no," she interrupts him. "That's Mistress Lisa for you. Try again."
Groaning desperately, he swallows before trying anew.
"Mistress Lisa. Please let me drink," he forces out, as clear as he can and adds a quiet, "please…"
"That was better," she didn't sound convinced, but then shrugged. "Not perfect, but it'll have to do." She lifted his head a bit and pressed the glass to his lips before slowly tipping its content into his mouth. The vine was sweet and heavy, almost sticky, but he swallowed it eagerly. Once, he choked on it, but Lisa paused, let him cough, and then gave him the last bit to drink as well.
"Thank you!" he whispered after she'd brought him a second glass and he meant it.
"You can pay me back later," she said soberly and returned to the table.
"You're too nice!" Mona said and popped some small green fruit into her mouth. "I would have given him something else to drink, more directly."
Lisa snorts. "We'll get to that. First, he needs to recover a bit, don't you think? Farina had her fun, it's our turn next."