Dark Romance (sispuppet & LaBellaMia)

Caitlin whimpered when he told her she couldn't and when he took her off, she closed her eyes and then nodded. Taking the panties from her mouth once she was upstairs, she undressed and then slowly moved to the drawer. She took everything out, laying it out for him so he would use what he wanted at his pleasure then moved to the bed and leant over the edge, legs slightly spread. If he wanted to cuff her or gag her he could, if he wanted to punish her he could. Not that she deserved punishment. Oh god she wanted to orgasm so bad. Her clit was swollen, liquid heat running between her legs and down her thighs.

She heard him open the door and glanced at him before looking down, brushing her hair to one side, remaining quiet as she kept herself exposed for him, the plug visible with her stance as she was leant over and naked. Cait was a hot and throbbing mess and her self control was nearly at it's end. She just hoped he gave her permission soon or she might just lose her hold on keeping her orgasm at bay.

Alex steps inside the room and closes the door, locking it behind him. He looks Caitlin up and down. Her pale back is flawless above the waist. Along her ass though are a number of red marks still lingering from her various punishments. He walks over and presses his hand to one of her cheeks. Seeing Caitlin shudder just from that touch, he chuckles. She was barely holding herself together as it was. Grabbing the plug, he slowly pulls it out, hearing a groan from the girl. “Don’t worry.” He tells her. “You’ll have something else there soon enough.” Turning around, he walks back to the dresser.

Alex puts the toy aside to be cleaned later as he examines the other objects laid out for him. He tries to decide what, if anything, he wants to use right now. First he stops at the gag. No, he wants to hear what sounds she makes as he enters her. The handcuffs wouldn’t be needed either since he still has the straps on the bed. In the end he decides on nothing. There would be enough fun had already tonight, and there would be opportunities for other things later. He turns back and returns to the bed with only the small bottle of lotion in his hand. He pours some in his hand, working his shaft out of his pants without stripping, giving it two slow strokes with the lotion before spreading some on a finger. Without saying a word, he slowly works it along the girl’s asshole, pushing his finger in before slightly before taking it out.

Caitlin listened to him moving around and when he pulled out the plug, she felt the throbbing as the muscles moved to try and go back to what they were normally. As his finger entered her, she moaned softly and then felt him take it out. Caitlin wanted to beg for release. But she couldn't speak. It was his rule that she wasn't allowed to talk and she just wished she could. Cait didn't want to gvet punished for talking out of turn but if he kept on, she might well get punished for orgasming without permission.

Her hips moved back against him, wishing he would do more than just a finger. Caitlin felt empty, needy and so soaked her juices were spilling down her thighs and there was an unending throbbing in her clit where he had nearly got her to orgasm before he made her stop. The sorry bastard, she thought bitterly, closing her eyes, sweat beading on her forehead as she tried her best to keep her climax at bay.

Alex presses his hands to Caitlin’s ass, squeezing each cheek before moving up and taking hold of her waist. He holds her tight, moving her back towards him. Slowly, he rubs the length of his shaft along her crack, teasing her with the tip but not actually entering her. “You’re awfully quiet.” He says, fully aware of his own rules keeping her from making a sound. “You must not want this.” He spreads her ass, pushing his length inside until the head is pressing against her tight hole. He pulls back after running from the top to the bottom of it. “I guess we can just call it a night then.” He says as he once again rests his length against her. “I’m sure you have no complaints.” Leaning in, Alex starts kissing her neck while he fondles her, resisting the urge to chuckle. “Unless of course, you do want it…” His teeth close against her ear lobe, biting it softly. “What do you want your master to do?” He whispers into her ear. “He wants to hear you beg for it.”

She moaned when he gave her permission to speak and beg. Pride shoved aside, she whimpered and then started to speak. "I want you to fuck me Sir. I want to feel you inside of me...and I want you to let me cum. Please Sir...please...please let me cum. Let me feel you moving inside of me, let me feel you spill yourself in me. Please sir..." she panted, trying her hardest to not orgasm before he gave her permission. "Oh please sir...use my body, fuck me, cum inside me, let me cum, all those things...please...please," she said, whimpering and biting her bottom lip almost hard enough to draw blood. She was begging him just like he wanted, saying what she wanted and she just hoped that he would let her orgasm before she lost control of herself.

Alex listens to her begging, letting her go on until she was out of breath before chuckling softly. “Well if you insist, then who am I to deny my little pet her treat?” He whispers to Caitlin before throwing her to the bed. She gets back up to her hands and knees, staying on all fours while turning her head to look at him. “Just like that…” Alex lets her wait for him as he slowly strips off his clothes. He spends a couple of seconds undoing every button of his shirt before gently folding it up and laying it on a chair. Next he removes the belt, and sees Caitlin brace herself for it.

“Not tonight dear. You’ve been so obedient so far.” He tells her as he unzips his pants and pushes them down before adding it in a pile with his shirt. His underwear and socks come last, once again being placed with his other clothes. He walks over to the bed again, climbing on it. “You’ve been so patient. Well you don’t need to wait any more.” He promises her. Spreading her for him again, he presses his cock to the hole and with a push, begins to enter her last virgin hole.

Caitlin watched him as he undressed, slowly and deliberately and then he was moving onto the bed. When he started to spread her, she lowered her head and then felt him pressing at her anal passage and then he was starting to enter her. Thankfully, the anal plug had done it's job and his entrance was eased but he was still bigger than the plug. Moaning, she felt his entire length enter and then felt his waist pressed against her ass as he bottomed out.

"Mmmm..." she sighed then closed her eyes, lifting her head andpressing herself back against him, hoping that he would give her permisson to cum. He hadn't exactly done so so she didn't want to do it and then get in trouble for it.

Alex lets out a long breath he hadn’t realized was held once he’s all the way inside his mistress. The new experience, a first for the both of them, is nearly enough to make him cum. He wants to savor it though. He starts to pull back out until only the head of his cock is inside her before pushing in slowly again. He repeats this once more, taking his time to adjust and make sure it’s comfortable. He pulls out again and waits, taking a deep breath before thrusting in harder than before, pushing with all his strength until he’s all the way inside the girl. Caitlin is rocked forward, the force knocking her off her balance and causing her to fall face first onto the bed. Alex pulls out, fiercely thrusting in again with the entirety of his cock. He groans out in pleasure. “Is this what you wanted? Do you like having your master fuck your ass like this?”

Each slow thrust was so uncharacteristic of him that it was nearly disconcerting. Then he slammed into her and Cait found herself falling face first into the sheets and gripping them while her ass was still high in the air while he fucked her. "Y-yes," she panted. "Y-yes sir," she agreed and then moaned, her clit still swollen, her body still despeate for release. God help her she needed some damn release. She pushed back against him, staying down because she knew he would only slam into her hard enough to knock her down again. "I like it. Please don't stop," she begged him, once more pride shoved to the side. It was impossible to have pride in the bedroom with this man. A man who enjoyed her begging and moaning and sometimes her degradation but he hadn't once taken it to far.

“Oh, I have no intention of it.” He tells her. He pulls out once again, and holds his position this time until his quivering cock aches to be inside her again. He thrusts hard, filling her, fucking her fast as sweat starts to pour down his body. He knows he wouldn’t last much longer at all, and sure enough, within a few minutes, he feels the now familiar tightening of his balls as his cock is hilted inside the girl. He releases his full load inside of her shaking body, his cock throbbing against her walls with each thick burst. His nails drive into her waist, holding her up and against him until he’s poured every last drop of his cum inside the girl’s ass. When he finally pulls out, he falls back on the bed, turning so that he’s next to her. “Did you cum?” He whispers pantingly into her ear, not having paid attention at the end of it.

Caitlin grunted with each thrust, fighting her orgasm as he slammed into her. It was the hardest thing she had ever done and when he found his own pleasure and filled her ass with his seed, she shuddered, gripping the sheets even as he kept her close and when he pulled out, she just remained as she was, to afraid that if she moved, she would shatter. At his question, she swallowed and lifted her head to look at him. "N-no sir," she stammered weakly then closed her eyes. "You didn't give me permission Sir..." she said on the next breath, trying to not move because she was so hot and bothered. Her whole body was covered in a thin sheen of sweat and her sex was still hot and ready and throbbing but he still hadn't given her permission. Her eyes were shut, only to concentrate on not orgasming.

Alex looks at her in surprise. She had managed to hold it together through all of that? He could have sworn he gave her permission to cum, hadn’t he? He tries to remember, but his whole mind is in a haze. Shaking his head, he pushes himself up and lays her back against the bed. “That simply won’t do. You need a proper reward, you know that?” He tells her, planting a kiss on her lips. His hand runs up her chest, giving Caitlin’s breast a squeeze. He feels her react strongly to it, and knows that she is barely keeping herself stable.

Alex moves down on the bed, spreading his lover’s legs open. He presses his hand to her sex, feeling the moist warmth. His finger barely brushes her clit and still she bucks at him and whimpers. Smiling, he leans in and licks gently at her outer lips. He feels Caitlin shudder at the touch of his tongue, and tastes her sweet arousal in his mouth. He leans in closer, lapping at her wetness, and letting it invade his senses. His tongue slowly works its way around the girl’s clit, not touching it directly for the first few seconds before he gives it a quick flick and moving downward to probe inside her.

As he started to kiss her, she kissed him back and then he's moving down to start on her pussy and the more he touched the closer she got to orgasm. As his tongue probed, she couldn't hold back any further, she exploded. Her juices flowed and her inner muscles contracted as he touched her. She couldn't help it and her body just tipped over the edge. The orgasm was so strong that black spots danced in her eyes. "Oh god...oh god..." She just started convulsing and then gave a sharp cry. Waves crashed over her of nothing but pure ecstacy and then it became to much and she collapsed onto the bed, replete and barely conscious, even as her insides quivered from orgasm. "Th-thank you," she whispered softly and then lost the fight with her consciousness and slipped into total darkness.

Alex keeps licking and suckling at Caitlin’s sweet juices all through her orgasm. He only stops once she collapses and thanks him. Going any further would probably just leave her sore anyways. Smiling at the events of the night, he moves up once again on the bed. Caitlin opens her eyes, looking at her master as he leans into her and presses their lips together. His tongue finds hers, licking along it gently so she can taste herself on him. “You’re welcome Caitlin.” He whispers to her.

Getting up and going to the bath room, there’s the sound of running water before he returns and picks her up. Just like on their first night, he carries her gently to the tub, setting her down in it before climbing in himself. “I’m glad you enjoyed yourself tonight.” He says, kissing her neck as his hand moves to her ass, he runs his fingers along it before moving back up to her waist.

Caitlin had actually passed out but woke up when he kissed her only to fall right back to sleep from pure exhaustion. Her next conscious thought was being submerged in the hot water of the tub and she opened her eyes and watched him enter the tub as well. She slipped into his embrace and then looked at him before laying her head on his shoulder as his hands roamed her body. "It was good. Better than good," she whispered and then lifted her head, kissing his lips before just curling against him in the water. "I'm exhausted now though," she admitted, her fingers lightly tracing his shoulder and moving downward to interlace their fingers.

After a moment, she lifted her head and then gazed at him. "I am glad you are my first lover. I don't think if I had been with anyone else before that it would be as good as it is with you. Even if I was apprehensive at first." She kissed his lips then drew back before smiling gently. "I'm very happy right now..." she promised, giving a smile.

“I’m happy I’m your first as well.” He tells her. “That I’ve managed to make you happy, well, I still can’t believe it.” He mutters as he hugs her tight. He stays in the water a while longer as Caitlin drifts off to sleep in his arms. Draining the tub, he grabs a towel next to him and dries her off before slowly making his way back to the bed. Laying her down, he climbs in next to her, brushing a strand of hair aside before planting a kiss on her lips. “Good night beautiful.” He whispers to her before he goes off to sleep.

“That looks amazing on you.” Alex says as he watches her standing in front of the mirror. The dark blue dress glimmers and hugs her tight, the small slit traveling up her legs. The front dips low enough to show off a bit of cleavage while staying classy. The high heels she has on accentuates her long pale legs and the curve of her ass even more. Alex can barely keep his hands off of her, but he knows he has to wait. This dinner party would be very important. He checks her choker, the small necklace looking fancy enough to pass as any other piece of jewelry. Especially when accompanied with the bracelets and earrings she has on. There’s one last item he had to make sure she had on though.

Stepping up behind her in his own dark blue dinner suit, he wraps an arm around her waist, pressing his hand to her crotch. “Did I put it on like I told you to?” He asked, though he knew it was pointless. Over the past week, it had become apparent just how obedient Caitlin had become. Ever since that night where she held herself together to the point of bursting, she had never once disobeyed him. Just the thought of that much control over her had him hard. They don’t have time though, so he forces himself to calm down.

Caitlin looked at him as she grabbed her clutch. They were headed out to some dinner at an associates house and he had come home with a pair of underwear that would vibrate and was operated by a simple dial that had four different speed settings. As he wrapped his arm around her and touched between her legs, she blushed. "Yes sir. I certainly did though I admit they do clash with my strapless black bra," she said, turning and kissing his lips. "And don't worry. I will stay next to you, keep my head down and won't speak unless addressed. Do I get to attend as Caitlin this time or do you have a new persona for me?" She asked softly, looking up at him and giving a gentle and trusting smile.

It seemed like everything was so much better between them compared to those first few days. Her obedience was a sign of respect to him and to his position but outside of the bedroom, he treated her like an equal. Sure he still had his sadistic side but now that he had accepted it, he didn't hurt her in anger and any sort of hurt was always mixed with pleasure and it had created this almost impregnable bond between them.

She straightened his lapel slowly then her green gaze lifted to watch his features. Her dark red hair was pinned in a neat and stylish chignon and she looked the part of a proper guest to a billionaire.

"Well that can’t be helped.” He tells her. “Not many options in colors over there. Don’t worry though, I’ll order more for later.” He promises. Smiling at her knowledge of the rules, he nods and holds out his arm for her. “It sounds like you have it perfectly figured out. Keep this up and I’ll give you a reward tonight.” He says. At her question, he looks her up and down. With her still being 17, it would be safer to go with a disguise. He had completely forgotten about it though, and it would delay them to have her change before dying her hair. Besides, the mix of her red hair, green eyes, and blue dress were too alluring for him to want to ruin. “No, you’re perfect as you are.” He tells her. “Caitlin will be a fine guess so long as she follows my rules.”

The limousine is waiting for the out front, the driver holding the door open so they can climb inside. Alex decides to have some fun during the short drive to the party. Kissing Caitlin’s neck, his hand travels up her leg to her panties, pressing two fingers against her sex. He turns the device on, giving a brief test to make sure it works. Judging by the reaction, it’s exactly what he wanted. Stopped in front of the manor, an attendant opens the door and greets them. Caitlin clutches Alex’s arm tightly. She may have become a quick enough expert at walking on high heels, but doing that as there’s a constant vibration against her clit is no easy feat. “Steady yourself.” He tells her, putting a smile on his face as they walk into the party.

Caitlin looked at him and then smiled. As they rode to their destination, she had to control the gasp as he put the underwear on one of it's settings and shed could feel the soft vibration on her clit. Low and thankfully not intense but she got the feeling he would be moving it up and down in intensity at his own discretion. As the limo came to a stop and the door opened, she faltered and gripped his arm in a vise, trying to keep her composure. She righted herself and then started to walk in with him. This was a real party with a good one hundred people gathered in the foyer and ballroom of the mansion where people of all types were enjoying the fine wine and h'ors d'eurves. She kept her hand in the crook of Alex's arm, glancing around but keeping her face slightly down, hearing the chatter and soft piano music playing in the background.

"Ah Alexander..." a woman said approaching and giving a smile. "You must introduce me to your dear little friend." The woman was an heiress by name of Alice Durham who's father had gotten rich through a very successful investment firm. She had wanted to sink her claws in Alexander Jacobs for years and saw the young thing on his arm as mere ompetition she would have to get out of the way.

Alex walks around the party, and for once doesn’t feel out of place. Any man not here with his wife had some young escort around him. It was badge of honor, in a way. The more successful you are, the sexier and more beautiful your date was. Alex smiles as he rests his hand on Caitlin’s. If that was the criteria, then he considered himself the most successful man in the room.

They barely start to make their way around the crowd before she shows up. Alex resists the urge to roll his eyes. He knew her father, and was even good friends with the man. Unfortunately, it was painfully obvious how spoiled she was, and even more obvious, just what she would do to be even more spoiled. “Good evening Alice, how is your father?” He asks, returning the polite courtesy. He leans in and gives her a kiss on the cheek before turning his attention to Caitlin. “This is my… confidant, Caitlin.” He says. Girlfriend isn’t a generally accepted term in these places, and calling her his live in mistress would only cause problems. “We’ve been together for a short while now, but she’s already managed to steal my heart. Come now dear, no need to be shy.” Caitlin nods and softly replies to the girl.

“Hmm, well, hopefully it’s just his heart you’re after. You seem pretty enough to get by on your own, no?” Alex is about ready to slap the hypocritical bitch, but holds his tongue, smiling as though he didn’t notice the hidden slights against his lover. “I really should be off now. We do need to catch up Alexander. It’s been too long.” She gives a sultry smile before turning and walking off.

Alex waits until she’s out of earshot before leaning in to whisper into Caitlin’s ear. “There are quite a few rumors about that one.” He tells her. “The word dead fish has come up more than once.” He quickly fixes his stature and continues walking around the party. High school level gossip wasn’t exactly the mark of a wealthy man after all. He takes the time to introduce Caitlin to a variety of people, always giving her a quick note of who she would be saying hi to, and what to expect. “Be careful around him. After a few drinks he gets grabby. Blames it on the alcohol, but it’s obvious he’s just looking for an excuse.” He whispers as they reach one large man. “He smells weird. He’s a great guy. The absolute best in his field, but well, he smells weird. Just don’t bring it up.”

Caitlin nodded at everything he said, the underwear a bit of a distraction but she did her best to look composed, keeping close to Alex as he introduced her to certain men or women. The woman Alice's words had made her cheeks flame but she had bit her tongue and pretended that she hadn't heard her. Once they had made the rounds, she sipped at the champagne in her hand, trying to not concentrate on the vibrating against her clit. "I guess they think I'm some gold digging little girl out to get all of your money..." She smiled at him then looked down. "Though to be honest, I wouldn't know what to do with all the money in your bank. I think I could live off a million for years," she grinned then flushed and looked down, feeling a surge of pure heat move through her and it nearly took her breath.

She could see the crowd of beautiful gowns and tuxedos, hear tinkering laughter. "I don't think I have ever been surrounded by so much opulence," she murmured then turned and looked at him, smiling gently then biting her bottom lip. "I sort of feel like Cinderella," she giggled lightly. "Except I don't transform at midnight. I get to be your Princess." Cait blushed then looked down once more.

Alex’s rule of no talking is temporarily forgotten as he quickly acts to comfort her. “We both know that’s not true though. Trust me, this is one of the matters that I couldn’t care less what their opinions on it are.” He smiles at her comment concerning his money. “Probably put most of it away, and hire some young, sexy looking guy to accept your odd, sadistic kinks.” He suggests, winking at her. With Caitlin’s comment about being his princess, he laughs and takes the glass from her. “I think someone’s had a bit too much now.” He tells her jokingly before leaning in, brushing her hair aside to whisper in her ear. “You’re forgetting the rules too quickly.” He walks them around a pillar, just out of sight of the party. All it would take is one person to randomly wander by to see them.

He gives Caitlin a hard kiss as his hand slides up. There’s a quick flick, and the setting on the panties is raised to the next level. “Do try to behave yourself, or I may have to not let you cum tonight.” He warns as he straightens himself up and steps out with her on her arm again. There’s no dinner planned for the evening, only the h'ordeuvres, and drinks. Some seats are available for anyone who doesn’t wish to keep standing, but for the most part, people are walking around and mingling. “Hurry up now. I still need to show you off a little more.” He says as he pulls her along.

Caitlin blushed. She had maybe had half a glass and when he pulled her to the side, she kissed him as fully as he kissed her and then gasped when he raised the intensity of the vibrations and as he pulled back, she had her eyes shut tightly to try and regain control so that she didn't orgasm. As he pulled her from their alcove, she put on that facade of sheer subservience, shy and quiet, biting her bottom lip and letting him lead her where he may. The humming against her clit had her feeling a little shaky but she didn't orgasm though with the higher intensity, it was slowly becoming n teasingly difficult.

Eyes seemed to follow the as they walked and she heard some remarks made about her that made Caitlin flush. She wasn't used to a guy calling her sexy or anything like that besides Alex and with him, at least it sounded respectful. As they approached a few men and their female counterparts, she kept close to Alex, glancing around to see Alice Durham glaring daggers at her and she turned away, not daring to glance at her and tried to keep a straight face while her insides quivered.

Alex moves his hand down to her waist while they’re walking, becoming more possessive of her as the night goes on, and the other men become more open with their comments. “Do you like their compliments?” He asks her when he sees the redness in her cheeks. “Don’t forget who you belong to. Your master wouldn’t approve of you running off with some other man.” He mutters, running a finger along her choker.

He excuses himself and Caitlin, explaining that they just need a bit of fresh air. Stepping outside, he waits until they’ve walked a good enough distance away from prying eyes at the party before pushing her against a wall and leaning in to give her a deep kiss. His hand travels up her leg, even pushing her dress up along the way. If they got caught, needless to say it would be hard to explain what’s happening, but at the moment Alex isn’t in the mind to care about that. He grips her thigh tightly before his finger moves to the crotch of her panties, pushing it to the next level. “Oh Alexander, it was a bit stuffy in there. I thought I’d join you.” He curses under his breath and quickly pulls away as Alice turns the corner. Their heavy panting and Caitlin’s state with the setting now one away from the max makes it obvious that the two aren’t looking to be disturbed. She raises her eyebrows as she steps closer to them. “Oh, is your date not feeling well? If she needs to go home and rest, then I could keep you company for the evening.”

Alex glares at her as he steps closer to Caitlin, gripping her arm. “She’s fine, just needed a bit of air. We’ll be going home a little later. There isn’t much to do there these days that we haven’t already.” He informs her. Not usually being one to brag, he can’t help but make it clear that Caitlin is not simply a one night occurrence. “Now if you’ll excuse us.” He says, nodding politely as he looks to Caitlin to see if she needs help walking.

"I don't forget at all," she whispered then walked with him to the little alcove just our of sight of everyone else. She moaned. "All yours Sir," she promised then moaned as he kissed her, panting when he moved the panties up, gripping his coat. She would of continued to grip if that stupid woman hadn't started to come around. Caitlin straightened slowly and then looked down, brushing hair out of her face, blowing out a deep breath and then felt Alex move closer to her, being protective and possessive and then her cheeks flood with color. The woman's face was priceless to say the least. As Alex looks back, she just gave a nod to signify she was alright and then walked with him back toward the main room.

"Well have fun with that gold digging tramp," Alice was spitting. "You bastard....I hope that whore takes you for all you are worth," she spat then turned and left. Caitlin felt warmth in her cheeks and kept her eyes down because the underwear was driving her close to orgasm. She hoped she wasn't looking sickly because it was getting harder to keep the orgasm at bay but she would. No doubt.