Breaking Her In

I should note that this story was written for a certain unnamed someone. All persons in this story are above the age of 18.

*****

It was the cold that woke her up, and as she woke up, she became more and more agitated.

She was naked, yes, and her pussy freshly shaven. Her nipples were hard from the cold, jutting out proudly from her 32D breasts. She shivered as she realized her long blonde hair was up in a ponytail. Her arms and legs ached, and she recognized that she was bound up on the wall. Her eyes took in an unfamiliar sight.

It was a dungeon, she thought. A sex dungeon. Her eyes fell on all sorts of things meant to increase her pleasure. . . or punish her. Paddles of various shapes and sizes, whips and floggers that made her whimper in fear. Nipple clamps, both alligator and clover clamps, edged in rubber. Dildos and vibrators of all shapes and sizes and colors, with different functions. Butt plugs and Ben Wa balls, laying haphazardly next to a bottle of anal grease. Hot wax was heating up nearby. A St. Andrews Cross stood bold as brass across the room from her. Up on the wall, hundreds of bras, g strings, corsets, and crotchless panties leered at her.

Suddenly the door opened, and a man entered. He was tall, fit, and physically imposing. His dark black hair was tousled, his dark brown eyes amused and excited at the game he was going to play with this little girl. She was shaking, the poor thing. He gently let her down off the wall, but made sure she was kneeling in front of him.

He finally spoke. "Do you know what I am, little one?" he asked softly, his low voice soothing.

She nodded. "Yes, sir."

He smiled. She was polite. He liked that. "Good, little one. So you know that my word is law, and your body is forfeit?"

She nodded. "Yes, sir."

"Good little one. Now, it's time to start," he said. He pointed to the wall filled with outfits. "I would like for you to choose ONE bottom and ONE top. They must to be to your tastes, but also so I can play with any part of your body as I wish. Understand?"

She nods and looks at all of the different outfits. She hesitantly chose a simple black g string and a black corset that just supported, not cover, her breasts.

"Good," he cooed to her softly, looking at her hungrily. "Come here," he told her. She walked over to him and stood before him. "Kneel." She knelt. He smiled. He liked obedience. "I will be good to you as long as you follow orders, understand?" he asked.

"Yes, sir," she said.

"Good. Now, lay down on my lap, face down, ass up," he told her. He licked his lips in anticipation.

"Yes, sir," she said, laying down as he instructed. She was quivering, from fear or excitement she didn't know.

He ran his hand up and down her tiny, tight ass. He peeked between her cheeks to see that she had no stretching of her rosebud. He gently pulled on her ponytail. "Little one, I'm going to give you a choice now. I notice that you have yet to have a cock in your ass. Would you like to be fucked in the ass first, or second?" he asked softly, still rubbing her ass soothingly.

She gave it some thought but ended up shrugging. "Whatever you want, sir," she said politely.

"Little one, I want you to choose," he told her, still stroking her ass, his voice gentle, but a little firmer.

"It is not my place to choose, sir," she replied.

"Last chance, little one, or I choose for you," he said sternly, frowning slightly.

"You choose, sir," she replied.

He quickly grabbed a butt plug and shoves it into her ass without any lube, her screams making him smile. "See, when I give you a choice. . . I expect you to choose. . ." he explained, picking up a paddle and rubbing it over her ass. "That just earned you fifty swats, little one. You need to count each one, or the punishment will start over."

She whimpered. "Yes, sir," she whispered.

"Good, little one," he whispered before he began spanking her quick and hard. She counted, but miscounted around number 26 or so, and the punishment started over. She miscounted again at 45, and she winced as he rubbed her very sore, red, ass. "So close, little one," he whispered. "So close. But I must start over."

She whimpered out each number now, tears streaming down her cheeks, being careful not to miscount this time. When he was done, he set the paddle down and gently rubbed over her burning ass. "I don't wish to punish you, little one, but I will if I must, do you understand?" he asked softly.

"Yes, sir," she whimpered.

"Good," he whispered. "Now, I'm going to take your pussy, then your ass." He sensed her tears and wiped them away gently. "It's okay," he told her. "You did very well, and I hope not to do that again." He helped her up off his lap and undid his jeans and slipped them off, exposing his cock. He led her over his legs and had her straddle him, taking his cock in her. She moaned loudly trying not to put any pressure on her very sore and hurting ass.

"That's it, good little one," he purred, moaning loudly himself as he felt her tight pussy close around his large cock. "That's very good."

She began slowly riding him, feeling stuffed. Her moans escalated very quickly.

"Now, little slut," he groaned out, feeling pleasure. "You know you're not allowed to cum without my permission, right?"

"Yes sir!" she whimpered. She was getting close, but she held it back.

"Good. . . who owns this cunt, slut?" He slammed into her, his hands digging into her hips.

"You, sir!"

"Who owns this ass?" Another slam.

"You sir!"

"Who owns YOU?!" A harder slam, followed by a smack on the bright red ass.

"YOU, SIR!" she screamed.

"Good. . . fuck I'm getting close. . . Beg for my cum in your slutty pussy." He gasped, loving how tight she was. He slammed into her harder.

"Please, put your cum in my slutty pussy. . . please sir, I want it so bad, please sir, I'm your little slut and playtoy, please sir, cum inside of me. . ." she begged.

He growled and slammed into her harder, encouraged by her begging, and came hard inside of her, shooting rope after rope of sticky, warm cum into her pussy, growling softly in pleasure while she thrashed and moaned on top of him, feeling him fill her up over and over again.

"Very good, little one," he said softly, wrapping his powerful arms around her and pulling her to him. "Did you cum?"

"No, sir," she whispered, shaking from the need to cum while he held her.

"Good girl," he muttered in her ear before attacking her neck, making her gasp and arch her back against his. She whimpered and moaned, thrashing.

"Now, for being a good little slut," he whispered in her ear. "I'm going to grant you a small reprieve from not being fucked, since your ass is next." She gave a soft whimper and he chuckled. "You've had the plug in there for a while so you're a bit more open than you were when we started," he reminded her. "Now, little one, I'm going to affix clover clamps to your nipples, alright?"

"Yes, sir," she whispered softly, sliding off his cock and kneeling down, presenting her breasts.

"Very good girl," he purred as he grabbed the clamps and gently attached them to her nipples then watching her double over as she gasped and moaned, wanting them off, they hurt her nipples so badly. "Now, I'm going to give you a choice of how you can take my cock, slut. You can take it on your hands and knees, or you can lower yourself onto me. Which will it be?"

She brought her head up, shuddering, still in pain from the clamps attached to her. In her pain filled state, she whispered, "I don't know, sir. . . which will make it hurt less?"

He gave a soft, amused smile. "Well, on your hands and knees, I control how fast and hard. If you're on top, then you can control how fast you go."

She thought for a moment before shaking her head. "I can't decide, sir. . ." she whispered.

"Oh, little one, do we need to go over this again?" he asked. He crouched down so he was eye level with her, and caressed her face with a soft, gentle thumb. "It'll be worse if you don't cooperate, and I choose. I don't want to punish you, I want to use you, but I want you to submit. Do you understand?" She nodded, too afraid to speak. "Good. Now, except for not choosing earlier, you've done a good job. Close to earning the right to cum. Do you want to go back and have to work harder for that?" She shook her head and whimpered softly. He gently kissed her forehead. "Then choose, please. Don't make me punish you again."

She nodded and whispered, "On my hands and knees, sir."

He was pleased with her choice and smiled. "Then on your hands and knees, slut. And keep that ass up at all times. You don't want to know what will happen if you don't. Okay?"

"Yes, sir," she whimpered as she got on her hands and knees, presenting her ass to him.

Gently he removed the butt plug and checked her out. There was no damage done, and he grabbed the lube and gently spread it around her tiny little rosebud and on the head of his cock, causing her to gasp in surprise at the coldness. He gave a smile and positioned himself before slowly feeding himself into her, getting more aroused as she scrunched up her face in pain and whimpered. He rubbed small circles into her side soothingly, feeling her tense up. "Relax, little one. . . Otherwise it's going to hurt more. . . ." She did her best to relax, and it was enough for him. "Good slut," he told her as he slid his full length into her and rested for a moment, feeling her wonderful tightness. "Good. . . good. . ." he moaned, running a soft hand over her sore ass. Giving it a light smack, causing her to gasp, he began slowly pumping in and out of her, while she moaned and whimpered in pain underneath of him. She didn't dare move, and he began moving faster and harder, his balls swinging to hit her clit, and soon she was crying out in pleasure as well as pain, spurring him on, making him go faster and harder.

"Christ," he groaned. "Your ass is fucking perfect, you whore. . . " He was close to cumming again, and he leaned forward slightly and grabbed her ponytail and brought her head up roughly, causing her to gasp and whimper. He pounded away a few more times before slamming hard into her and spraying the insides of her tiny ass with his seed, letting out a massive groan of approval. She whimpered and clutched at the bed sheets, her swinging tits aching, her ass hurting even more than before. Tears fell from her eyes and soon, he gently tugged his still hard member out of her and she collapsed against the bed, crying softly and whimpering.

"Oh little one, did that hurt?" he asked gently, wiping away her tears. She nodded, then winced, expecting a blow. He shook his head and chuckled. "There is nothing wrong with showing pain, little one. Pain can be just as beautiful as pleasure." She gave a small nod, watching him. "You'll learn that, in time. So relax. Did you get some pleasure from that?" She hesitated, then nodded. "Good, little one. . . That's what I want. . . Punishing you is to train you, not meant to be mean or vicious. . . unless that's what you want. Do you know why I ask you for choices?" She shook her head. "Because I want you to be able to decide how much pleasure you receive. I want to give you pleasure, but I want you to be able to choose. It pleases me when you do so, and I'm thankful you did so this time. I don't like punishing you." This was a small lie, he liked hearing the cries of pain when he was punishing her.

She nodded, then did something she didn't even expect herself. She crawled over on the bed to where he sat, watching her. She gently laid her head in his lap, her eyes looking up at him. Smiling, he brought his hand over and gently began to stroke her hair. "Do you like this, little one?"

"Yes, sir," she said softly. "Very much so."

"Good, little one," he murmured. "That's what I like to hear. Do you want more?"

"Yes, sir," she said softly, blushing.

"None of that. . . there's nothing wrong with saying what you want. You may not get it when you ask for it, but I don't know what to do to you or what you want until you ask for it, okay?" He gave a soft smile of reassurance.

"Yes, sir," she said, quietly.

"Good girl," he said. "Why don't you suck me a little bit, and we'll go from there, alright?"

"Yes, sir," she said, moving so she can get his cock in her mouth better. Kissing the head reverently, she started to suck gently but firmly, moaning softly as she tasted his cum and her juices and the lube he used from her ass. Groaning, he let her work, still stroking her soft blonde hair. He didn't want to cum in her mouth, not just yet. He felt the cold metal of the nipple clamp chain brushing against his thigh and it caused him to get harder, causing a squeal of surprise from his slut. He gave a soft, amused smile and let her work, gently pushing her head to get her to swallow him. She eventually did, and the sound of her gagging and sucking made him grin, watching her little body shudder. When he decided she had had enough, he gently pulled her away from his cock and kissed her cheek. "Very good, little one," he told her and he saw her eyes light up in happiness. He gave a gentle swat on her ass. "Lay down; we're going to try something new," he explained to her. "I assume you saw the hot wax?" she nodded, her eyes widening. He smiled and stroked her cheek as she laid there, naked, her arms and legs spread so he could play with her. "I'm going to remove the nipple clamps now; feel free to scream," he told her and he gently removed the clamps, causing her to scream and curl up. He gently slapped the insides of her thighs. "Don't curl up, it makes it worse," he told her. Nodding, she laid back into the spread out position, whimpering softly, her nipples hard and standing at attention painfully. He gently sucked on each nipple watching her buck and squeal and whimper. He held her hips down and smiled. "Where do you want the wax, little slut? You may point."

Nodding, she pointed to the undersides of her breasts and in between them, as well as the crease caused by her legs joining with her groin. She gently brushed her mound.

He smiled, watching her hesitantly touch where she wanted the wax. "Alright. Now, keep still, or else it's going to get places you don't want." Nodding, she forced herself to relax.

Smiling, he gently took the hot wax and spread it on the places indicating. She gasped when she first felt the wax hit her body, causing her body to arch slightly. He chuckled as he watched her, waiting patiently for her to calm down and when she had, continued. "Does that feel good, pet?" he asked her.

"Yes, sir," she moaned softly.

"Good. Now just let it warm up your body and harden, doesn't that feel delightful?" She nodded, the wax slowly hardening and cooling, it felt relaxing and she let out soft coos of pleasure. He smiled and when it had hardened completely, he gently brushed it off and she resumed her position of her head on his lap, her eyes wide. He stroked her hair again, thinking about what to do next with his little nubile slave.

"Up," he said after a few minutes of contemplation. "I'm going to see how high your pain tolerance is, little one."

"Yes, sir," she whimpered softly.

"Shh, it'll be okay. I just want to know your limits. You may even surprise yourself," he assured her, smiling indulgently.

She nodded and slowly got up from his lap. "Where do you want me, sir?" she asked.

"Go over to the cross; I'll put you up there. Face it," he told her, thinking about the best way to spank her tiny little ass.

"Yes, sir," she said. She walked over to the cross, a bit sore from everything that's happened. She faced the cross, trembling from the cold and fear.

He walked up behind her and gently ran his hands over her tiny body. "If you relax, it won't hurt as much," he told her, his voice barely above a whisper.

Nodding, she took a deep breath and forced herself to relax, but still she trembled. He gently lifted her up and placed her hands and legs into the restraints. She rested her head against the beams.

Deciding on his hand for now, he gently rubbed her tight little ass. Her rosebud still hadn't closed completely from the butt plug and fucking it had and it made him smile.

Out of nowhere, he began spanking her ass, gently at first, but getting harder as he listened to her cries become moans as she got used to it. She would feel pain, then pleasure, then more pain. It was just a continuous cycle.

Finally tired of his hand, and his hand beginning to sting from the force of the slaps, he contemplated the next utensil to use while he rubbed her ass and she gave a soft moan of mixed pain and pleasure.

Deciding on the paddle from earlier, he rubbed that over her ass and gave her the same treatment as before. The cries turning into moans took longer this time, and he adjusted accordingly. He looked at her face and noticed that there weren't any tears yet. "Feeling okay, whore?"

"Yes, sir," she whimpered.

He selected a thick stranded flogger and ran it up and down her back, letting her shiver from the feeling of leather. He ran it between her spread legs and brought the strands up to his nose. The fresh scent of her juices lingered and he touched the leather slightly, smiling as he found that they were wet. "You're enjoying this, aren't you?"

"Yes, sir," she admitted.

"Good. . . I'll see that you're rewarded for being good," he told her. "Just a little bit longer."

The flogger came down on her ass and she gave her first true cry of pain, throwing her head back. He waited for her to relax again before throwing the second one, and the same reaction happened, red stripes appearing on her ass. Again, he waited and then threw the third strike. Then the fourth. Always gauging her reaction and soon wasn't giving her time to adjust to it. Her cries turned to yelps, but not moans. He noted that and looked to her face, and saw a few tears leave her eyes, but he could tell that she was holding back.

"Little one, what have I told you about expressing pain?" he asked gently, stopping the flogging for now. Huge welts were beginning to appear on her ass.

"That pain can be just as beautiful as pleasure, and that it was okay to show that you were in pain, sir," she said, whimpering. The tears she had were small, but genuine.

"That's right, little one. You want to cry more, don't you?"

"Yes, sir."

"Then cry. I'm going to continue until you're sobbing, alright?"

He began flogging her again, and her soft tears soon turned into loud sobs. She dug her nails into her palms and drew blood.

He saw this and stopped. Quickly releasing her from her bonds, he held her while she cried, gently prying her nails out of her hands. "Shh, little one, it's over now," he whispered for a while, letting her calm down, rubbing her back. She had done well and impressed him with how far she went.

Once her tears had died down, he smiled and brought her head up so she could look at him. Her eyes were puffy and red from crying, and her lower lip trembled slightly. He kissed the top of her head gently, tenderly. "You did very well little slut. I am impressed and will reward you properly. For now, let me take care of you."

"Yes, sir," she whispered.

"It will hurt a little bit, but I don't want these welts to become scars, alright?" he said. "Go lay face down on the bed, little girl. I'll be back shortly."

"Yes, sir," she whimpered. He sent her off and watched her waddle to the bed and lay down. Grabbing a soothing cream, he walked over and began massaging her wrists and ankles, bringing circulation back and soothing the aching muscle beneath. He realized this was a sub who needed affection after any session, no matter how mild. Those usually made the best subs, because they understand the bond. Opening the soothing cream, he began to gently spread it around on her sore and aching ass.