Boy, Conquered

At first he didn't recognise her, then the poor woman turned her head sideways and caught his eye. Caroline! His beloved Mistress.

Caroline's long blonde hair, always so well kept, was now tousled and bedraggled. Her breasts hung beneath her, marked by bruises, her bright pink nipples stretched torturously long by lead weights suspended upon chains, attached to her delicate flesh with cruel looking clips. The porcelain skin of her back and buttocks was criss-crossed with more bruises and fresh red welts. Despite this, her beauty still shone through, though a small quiet voice deep within Matti's mind whispered that her situation in fact enhanced it.

"This slave has proved rather popular" Meredith near purred as she taunted. "I hear she's exquisitely tight. Well, you're about to find out."

Turning towards her charge, Meredith looked up at him, her hand reaching inside his robe, grasping his cock.

"You are going to kneel behind her, and you are going to fuck her tiny little bottom. Hard, I want to hear if she squeals like I've heard she does. You will use her, as if you were a Master and she your fuck-toy. You will give her no pleasure. And you will do this, as a sign of your loyalty."

Matti stood stunned, speechless, and danger flashed behind those pale brown eyes. He felt her grip his genitals tighter.

"Either you are mine, and you will do this, or you are still hers. If so, you will be cast down with her. And I don't think you would survive that pet."

Meredith spoke lightly, casually, but Matti sensed the intent. Meredith released her grip on him with a grin, untying his robe, pulling it from his shoulders, letting it pool at his feet. Stepping back, she slapped his bottom, gesturing for him to approach the fallen Arvalonian Lady.

The boy walked slowly over to her, moving behind his former Mistress. His eyes dropped to where her cunt lay, framed prettily by her thighs. Her sex had been shaven completely smooth. Most of the time Caroline displayed small, tidy lips, tightly closed, separated by a thin slit. Now they were swollen, glistening, parted with the inner lips fully on display, her entire sex a deep pink. Matti recognised the appearance of her when she had been well-fucked, and wondered how many cocks, male and female, she serviced each day.

He knelt slowly behind her, whispering so that only she could hear,

"I'm so sorry Caroline."

"Do not be," she replied quietly. "You must survive. Do as they say, use me hard, show no mercy."

Gently, almost reverently, Matti placed his hands on her bottom, careful to avoid the marks from her most recent caning, and used his thumbs to part her small round buttocks. Whilst Caroline had used his bottom daily, and had also taken him often into her vagina, he had never put anything more than a finger or tongue into her nether hole.

Her anus was as he remembered; small, pink, tightly puckered. She seemed dry, and completely closed, and Matti guessed that whatever else she may have undergone, her rectum had been off limits this day, to be saved for him, and this humiliation, alone.

Meredith broke the silence. "You may use a single finger to lubricate her."

Matti stopped, almost objecting before a whispered, "It's ok" from Caroline.

Still, he hesitated for a moment. He knew from years of giving his bottom up to first Caroline, then Meredith, that even his practiced bottom required two fingers to open and lubricate him to be able to easily and painlessly take a cock inside fully. Knowing though that if he disobeyed her fate would be far worse, he reached for the pot of oil which had been placed within reach, thrusting a finger inside, coating it completely. Then, using one hand to keep her buttocks open, he reached out and pressed his fingertip against her. He allowed himself to take in every sensation as he gently, but firmly ran his fingertip around the rim of pink skin. Then, pressing directly on the small dark hole at its centre, he pushed forwards, her anus opening easily, his finger slipping inside her. He was first struck by the heat of her, then by how smooth and tight her sphincter was. As he eased his finger further into her, she gave a soft moan, and his cock twitched. He hadn't realised until now how hard he'd grown, a delicate strand of pre-cum already running down to the floor between her spread knees.

His finger slipped past the second knuckle, and then his hand was pressing against her opening, he twisted his finger as he started to withdraw it and Caroline moaned again; she always had when he twisted his finger in her bottom whilst eating her soft cunt. In and out he moved, twisting, spreading the lubricating oil along with inner walls, his breathing heavy, erection throbbing, until the spell was broken.

"Enough pet!" Meredith commanded, the possessive term reminding both boy and fallen woman of who now ruled this city. "Fuck her now. Hard and deep. I want to hear her cry out."

With a small nod Matti slipped his finger from Caroline's bottom. Even with the brief attentions, her hole still looked impossibly small and closed up. Still keeping her small round buttocks parted, Matti brought his cock up to rest against her bottom. He heard Caroline breath out, and relax against him, pushing back slightly, the delicate rim of her anus appearing to kiss the tip of his cock. He responded by slowly pushing back against her, putting pressure on that delicate opening. His former owner gasped beneath him as her body surrendered to him, and slowly he began to feed the length of his penis into her rectum. Even after months of mistreatment, she was tight, almost painfully so. Though she had long since had her anal virginity taken from her, Caroline's bowels gripped his aching cock like a vice as he eased into her. Eventually, his belly pressed up against her buttocks, his thighs hard against the backs of her own.

He rested a moment, wanting to allow her to grow used to the size of him, but she hissed a warning.

"Don't wait. Fuck me, hard. You have to."

Knowing her to be right he arched him bottom back, slipping most his length from her, and driving back in. She cried out beneath him, but before he could pause she whispered,

"That's it. Do what they want."

He obeyed her, as he had for years, ignoring his feelings and began to fuck her, driving in and out of her small tight bottom. He squeezed his eyes tight shut, blocking out what he could, but the physical sensation of being inside her was so intense. He dimly became aware that part of him was enjoying the experience.

He gripped her buttocks harder now, digging his fingernails into the pale flesh, hearing her cry out. His cock throbbed, feeling every ripple and spasm of her tight bowels, driving in and out of that small pink anus, gazing in fascination at how it bulged in and out, stretched taught around his cock. 'This is what she is for now, she is just like me, to be fucked and used', he thought, as he drove ever harder into her, his former Mistress uttering staccato cries at the bottom of each thrust, Matti's hips slapping against her small round bottom. As he fucked her the weights hanging from her abused breasts swung back and forth, stretching her small nipples to their limits. Even so, he became aware that Caroline was playing an active part, rocking her hips, arching her back as he drove into her. He wondered if she was wet between her thighs.

He hasn't noticed her approach, but suddenly Meredith was kneeling behind him, stroking his balls and bottom.

"That's right baby, fuck her, use her. You belong to me now, you love me now. She's just two pink, fuckable holes. She's nothing pet, and you are such a good boy for fucking her so hard. I am going to reward you so handsomely. You're going to feel my tongue in your sweet little hole, then I'm going to make love to you so nicely, and we're going to cum together you and I."

As she spoke her softly caressing fingertips slipped between his buttocks, tracing lightly over his opening, slick with sweat.

"When we're done with her she's to be given to the soldiers. That pretty, neat slit of hers will never be the same again. She'll be ruined, gaping, you'll be able to fit your entire fist in her without lube."

The images she conjured played across his mind in explicit clarity, and Matti was conflicted, still feeling love and protection for his former Mistress, yet the submissive core of him undeniably excited by the thought of someone being used so thoroughly, of Caroline's perfect body in such carnal use.

Meredith briefly reached further forward between Matti's legs, finding the wet and swollen slit of his former Mistress. She grinned, the Arvalonian slut was a submissive at heart after all. She curved two fingers up between the smooth labia into the woman's empty hole, enjoying the feel of Matti's cock thrusting back and forth through the narrow wall between her openings. She was rewarded with a deep moan, Caroline unable to prevent it passing her lips. As she enjoyed the moment, Meredith heard her boy's breathing change, felt his thrusts become more urgent, and she knew he was getting close. She withdrew her fingers from Caroline's abused, slick cunt, and cupped his sac closely, massaging his testicles, whilst pressing a fingertip against his anus. She didn't even need to press into him, he did that himself as he drove backwards, impaling himself upon her digit, before thrusting back inside Caroline once more. Meredith curved her finger, reaching his prostate, finding it firm and sensitive. She saw Matti's grip on the fallen noblewoman tighten still further, his hips a blur as he threw back his head and gave a yell. Deep inside of Caroline's rectum his cock spasmed violently, endless amounts of his semen flooding her bowels.

--

She had fully intended to deliver Caroline to one of the soldier camps, to be used repeatedly, but Meredith had enjoyed the experience so much she kept the woman. She was given menial domestic duties, supplemented by a role as a toy for Meredith's sexual amusements.

Meredith never used Caroline herself, but she regularly watched Matti do so; always in the manner he had done so in that stone cellar: one finger to lubricate, then sodomising her hard and deep. Often she would have Caroline lay flat on her front, a pillow beneath her mons raising her bottom. Matti would lay on top, penetrating her bottom, and in turn, Meredith would mount the boy. His head buried in Caroline's hair, breathing her scent, her tight, rippling rectum holding him tight, as Meredith thrust into him in turn, always produced Matti's most violent and long-lasting ejaculations.

There were occasions when they could be alone together, and in those much treasured tender moments, Caroline and Matti were able to make love, equals now. They both inherently knew Matti's bottom belonged to Meredith alone, and as Caroline only ever got used anally during their sessions for their Gorran Mistress, Matti and Caroline would always make love missionary, face to face, kissing softly as his cock slipped sweetly into the warm embrace of her cunt. Those stolen moments, although fraught with risk, gave the Arvalonian pair great succour, and as time went on, Meredith was called away more and more often to attend court, and they were able to come together more and more often.

One such day, as they lay beneath the cool silk sheets, her legs wrapped tight around his waist, the indescribably wonderful feel of his erection arcing in and out of her, Caroline whispered in his ear,

"There is to be a rebellion. The Gorran court is fractured, confidence is high they can be driven out."

Matti gazed into her eyes, searching for hope there.

"And what about us? And Meredith?"

"Most of them will be executed, but her... her I want to keep."

"Keep alive?"

"Yes, but also keep. I want to do to her everything she has done to you, to me. The thought of it, it drives me on."

She spoke of revenge, but her whispers were more urgent, and Matti noticed she had lifted her legs, wrapping them higher around his back. He obliged sinking deeper into her, and she gave a small cry as he pressed against her cervix.

"Fuck me now pet, fuck me now, yes baby, harder now."

He did. Both of them filled with urgent need. Hope that freedom might be close. Thoughts of Meredith cast down to servitude. But it wasn't simply revenge that motivated those thoughts Matti realised, but a sexual thrill, a desire to fuck and use Meredith as she did them. Caroline felt the same way, he knew instinctively, and as they came together both of them had images of Meredith on all fours, submissive and waiting in mind. Aravlon would rise again.