2 comments/ 45483 views/ 3 favorites Caroline's Undoing By: SireLooksinMA In the Beginning...... The bright winter sun streamed through the windshield bathing her in its soft warmth. The two hours that they had been driving took their toll on her and she was nearly drifting off to sleep in the sun. She looked over at him and smiled to herself; he seems nice enough and she HAD been talking with him for months now on the Internet. She felt as though she knew him so well.....why had all of her friends warned against this weekend get-away with him? No matter now. It was done and they were on the way to his mountain hideaway. He was a tall man...substantially taller than her five foot two inch stature. He must be six feet tall at least. Although he was an attractive man, it wasn't his looks that attracted her to him. There was something about his manner....a calmness that shone through in his deep voice and everything that he did. He had a certain self-assuredness that stopped short of arrogance. He seemed to know that she would agree to go away with him even before he asked. How could he see so deeply into her she wondered. "Does he really know what I'm thinking?" She couldn't resist...she had to find out more. Caroline was a secure woman.... independent and confident. Years of raising her children alone after her husband left had made her that way. Always the consummate professional, she was quite conservative in most things that she did. This weekend was out of character for her. Still....something about him made it impossible for her to turn down his invitation. Before they left her suburban home, she had packed warm clothes, a silken bathrobe, pajamas and her beauty supplies. At his request, she had worn jeans and boots that laced up the front. The loose-fitting sweatshirt covering her exposed breasts was her own idea. Now, as they approached his cabin, she squirmed slightly at the thought of how brazen she had been to wear a sweatshirt and no bra. "We're here," Phillip announced as the car pulled into a deserted driveway just at twilight. Caroline could now see why he had requested the boots. There was nearly two feet of fresh snow even this late in April. Such a gentleman, Phillip was. He always opened the doors for her and now he insisted on carrying her bags to the cabin. And yes...the cabin! So filled with charm! Snow piled along the walls so high that it met the snow covering the roof. Only the front porch provided an escape from the snow to gain access to the entry. Once safely inside, Phillip sat Caroline down in an overstuffed chair and covered her with a warm blanket from the car. It was so cold and she could feel her nipples, taut and erect now, rubbing on the rough fabric of her sweatshirt. She watched as Phillip moved swiftly around the open cabin...lighting gas lamps and candles. It was only a matter of minutes until he had a fire roaring in the fireplace and it's warmth began to reach Caroline. Pushing the blanket from her shoulders, she leaned forward rubbing her hands in the warmth of the crackling and popping fire. Phillip was still lighting candles. He had them all around the cabin, but many close to where Caroline was sitting. Their aroma mixed with the smell of the wood of the cabin to create such a delightful contrast. Phillip appeared with a tray. On it was a bowl filled with chocolate covered strawberries, two champagne glasses, and an ice-bucket from which protruded the neck of an already opened champagne bottle. Quietly, without saying a word, he poured her a glass and handed it to her. "Oh, I love chocolate covered strawberries," she said as she reached out for one. "Not so fast, My Dear.....I'll give you one," as he reached for the stem of a strawberry from the bowl. Slowly he raised it to her lips...brushing it across them gently. She giggled like a school-girl. Why was she so much out of character when she was with him she wondered. And how, just how, did he know of her passion for strawberries? His teasing done, he held the strawberry for her to take. She loved the chocolate and wrapped her lips around the fruit as though it were her lover. As she did, she realized that he was staring deeply into her eyes. His eyes probing her soul. She could feel her face flush and her breasts begin to tingle. The nipples sprang to life immediately. Uncontrollably she began to moisten. She bit the strawberry from the stem and averted her eyes. Whether he could tell what she was feeling she did not know, but he quickly had another strawberry for her. This time she was a willing participant in his game...rolling her tongue around the plump berry before engulfing it with her lips. The champagne, the fire, the candles, his deep piercing gaze all had her head spinning. She was thankful when Phillip took her glass from her. She was afraid that she might drop it. But then he did something that she did not expect. He placed his hands on the arms of her chair, leaning over until their faces almost touched. Standing in front of her, his strong legs straddled her knees. There was a passion in his eyes and his voice was soft and deep. "There is something that I will want from you tonight." She caught her breath. Had she been wrong about him? Was she in danger? Somehow those questions melted away...she knew that whatever it was that he wanted...she would be drawn to give to him. "It's your submission, Caroline. I want you to submit to me. To turn yourself over to me completely. Can you do that? Do you trust me enough?" Her eyes half closed, she began to protest slightly. But his stare ate through her defenses. "Yes, if that's what would please you," she finally murmured. Smiling now.....Phillip moved away briefly and re-appeared with a small duffel bag. In the glow of the fire, she could see the shine of leather as he pulled two thickly padded cuffs from the bag. She rested her arms on the arms of the chair and let her head fall back on the soft cushioning of it. Phillip was kneeling in front of her now...she didn't resist as he began to unlace her knee-high boots. First one and then the other slid off in his deft hands. With the boots gone now, she could feel him pulling her legs toward him and the soft suppleness of padded leather wrapping around her ankles. She drifted off to her own world as her legs were stretched apart. She could hear the metallic rustling of chains and open her eyes slightly to see Philip securing her legs to bolts in the floor that she had not noticed before. Now...for the first time she felt completely helpless. Although her hands were not bound, she seemed unable to do anything to stop him. There was a passion growing within her that was consuming her... she was flooding her jeans with her juices. Phillip came to her now...straddling her waist, he reached under her arms and guided her up to her feet. He had to support her since her legs were extended by the ankle cuffs and the chains. She was guided to her knees and his hands slipped under her sweatshirt. Although she felt like as if she should protest, she couldn't find the words...any words. She was in her own space. His fingers found her erect nipples..squeezing them slightly...but all she could do was let out a slight moan. With the encouragement of her moan, Phillip pulled the sweatshirt over her head....leaving her naked from the waist up. The warmth of the fire covering her exposed skin. She knelt there before him...entranced. Watching him as he removed two more cuffs from the bag. A wave of apprehension swept over her as he placed first one and then the other cuff on her wrists. More chains bound her wrists to the floor. She was now on her hands and knees wearing only her now moistened jeans. Her eyes grew wide with panic as she saw Phillip remove a large two-sided knife from the bag. Sensing her fear, Phillip smiled slightly. "I thought you trusted me. Have no fear, My Pet.....I'll do nothing to hurt you." With that, he knelt behind her. She could feel the cool blade against her ankles causing her to draw a breath and hold it. Her heart was pounding as the blade traced a line along her calf. Not cutting...just barely touching. She breathed a sigh of relief as she felt the knife pull against the fabric of her jeans...easily slicing through them. In seconds he had her jeans and panties sliced off. She was now completely naked and absolutely vulnerable. Strangely she liked the feeling....she was completely aroused and she knew that she would do whatever he demanded. He came to her again. His hands exploring her body. She moved against him...responding to his wandering fingers and hands. They cupped her breasts, tickled her pubic hair, entered her. She couldn't help but breathing out a moan of delight as his fingers slid inside her and found her clitoris. Unaware of her surroundings or time, Caroline had drifted off into her own environment. She opened her eyes to see Phillip kneeling at her head. She raised her head...her lips parting slightly as she saw that he was wearing only a robe. As her eyes fixed on the swelling in the front of his robe, her tongue circled her lips. She was not even aware that she was doing it...but she wanted to please him so much right now. "You want me, My Dear don't you? I can see it in your face. Are you ready to give yourself to me completely?" He asked. "You know that if you do, you do so freely but completely. You will be mine to use as I desire. You will be available to me whenever I wish and in whatever fashion I wish." She quickly nodded her approval. Caroline had had many sexual relationships and was quite adept at oral sex, but nothing had prepared her for what was about to happen. As he opened his robe, she could see that Phillip was as aroused as she was. He was of average endowment, but she had never seen a phallus that seemed to her to be as gorgeous. She couldn't help herself...she strained against the chains to try to touch her lips against the swollen purple head. Phillip smiled, "Take it between your lips only if you agree to be mine. Only if you agree to wear my collar as a sign of your submission to me." Softly, he brought himself to her and she was a willing participant. Her lips wrapped around the silky-soft tip of his cock. The pre-cum on the tip was a treat for her and she circled her tongue around and around in it. She had never before had a man in her mouth who was so gentle with her. She could feel his hand on the back of her head, but it didn't force her onto him. He let her take him at her own pace. She was hungry for him and slid her lips further and further down his shaft. Her excitement heightened by knowing that she had now agreed to be his whenever he desired. Deep inside she wished that he would want her often. To Caroline's amazement Phillip drew back from her. Her lips followed after him but he was out of reach. "I have almost cum, My Dear. You can't have that yet. I must test you more first." With that, Phillip released the wrist and ankle chains from the cuffs. With an ease that shocked her, he swept Caroline from the floor, placing her gently on the over-stuffed chair again. She was quick to comply with him as he postured her in the chair with her butt on the very edge....leaning back against the pillowy cushions with her arms on the chair arms. "Now, My Dear....I'm going to be doing some things, but I want you to remain absolutely still...do you understand?" As he spoke, Phillip was dragging the back of his hand along Caroline's thigh. She tensed with anticipation as she nodded her acknowledgment. "If you move, I will have to punish you for your disobedience." Where it came from she did not know..the first she realized of it was when the tip of the feather began circling her hardened nipple. She flinched and squirmed slightly at its touch only to scolded by Phillip for moving. The feather traced its path along her body.... slowly tickling her...making her tremble and move against its soft touch uncontrollably. She opened her eyes as the feather stopped it course to see Phillip staring at her with a slight scowl. "I told you that you must remain still, My Dear. You mustn't move!" he warned. "I told you that to move would result in punishment.... you will have to feel the sting.... but that will wait." With that, the feather returned to its journey... its tip winding up one thigh, across her belly and down the other... only to reverse its path once crossing the sole of her raised and bare foot. The sensation was unbearable although pleasant. It took all that Caroline could muster to control the urge to move her body.. as if to scratch at a persistent itch. Finally, when she knew that she could take no more without displeasing him with her movement, she pleaded with him to stop.... tears welling up in her eyes. "Since this is our first time together and you have not yet learned to control your body or your emotions, I will end that part of your training here. In the future, I expect you to be able to withstand more and more of the exploration of the feather...even as it touches your innermost parts. But now, you will learn the joy of other exploration." she was told. "Later you shall also experience discipline for your disobedience." With that, her pulse quickened yet again. Her mind wandered... flooded with thoughts of what he might be talking about. At once embarrassed, shy, anxious but still profoundly aroused at the taboo nature of the thoughts and delights she was experiencing. Her mind was spinning... everything seemed a fog... almost as though it was not happening to her but that she was a casual observer of the intimacy. Only the sensations of his touch belied the reality of her experience. Then she felt him. For the first time his fingers were finding their way into her... gently but firmly. She tense and he stopped briefly.. only to tell her again not to move. With her whole heart and soul she struggled to comply with him.... for him. Her body answered to its own commands now and she began to moisten for him.. against his fingers. He was kneeling between her legs now and his index finger had found her clitoris. Never had she felt such a gentle touch rubbing the length of her. It was as though all of the love in his body, more love than she had ever imagined possible, ran through that finger and into her. It was too much... her head flew back deeply into the soft leather of the chair.. her eyes rolled back... her hips began to rotate against him. How it happened or when it happened she didn't know; but she soon felt his finger replaced by his warm, moist broad, strong tongue. It probed her and left a broad swath from her bottom all the way up to her clitoris. Then his lips wrapped around the organ as his tongue circled it. As she drove against him in wave after wave of orgasm, she could feel his hands pulling her cheeks to his face. She flooded him with her cum.... and succumbed to the overwhelming darkness that took her senses from her. CHAPTER 2 The Choice Consciousness came slowly back to her. The sense of confusion that she felt waking up in a strange environment eased as she took stock of her surroundings. The still burning candles, the warmth of the fire, the smell of the wood all restored her memory of exactly where she was. It wasn't until she realized that her body was curled against his... spooning... fitting perfectly into the curves of his body that she remembered what had already happened to her. His hand was strong, gentle and warm as it cupped her breast. She could feel his breath on her neck. Somehow, she couldn't quite remember how, she had gotten to the soft rug of the floor, and they lay there together both covered by the thick warm blanket. Only when she tried to move did she realize that she was chained to the floor, still helpless. Her rustling awakened Phillip. As He arose from the blanket Caroline noticed that Phillip wore his robe loosely over his shoulders, still open in front. His exposed genitals inexorably drew her gaze, which he noticed immediately. "Caroline, I asked you before if you were willing to submit yourself to me completely, do you remember that?" He asked. She nodded her head that she did, but began in protest, "Yes but it was just..." Before she could complete her sentence he raised his finger to her lips as if to silence her. "It is too late for 'but' My Dear.... you have already given me your answer... you are mine now. All that is left is for me to accept you. Do you understand that?" The panic was evident.... her eyes grew wide and her lips trembled. But slowly the chains worked their magic and Caroline, for the first time in her life, began to feel the complete security of surrendering all control. This man had been so gentle with her... so loving... and she had never been more aroused than she was earlier... nor had she ever cum so hard. So hard in fact that she had lost consciousness. It was the warmth in her soul that he had given her that began to drive her now... to formulate her thoughts for her... to express her innermost self through the words that she was about to speak. "Yes.... I remember.... I will do whatever you want." "Good," came the curt reply, and Phillip was gone... disappeared to another unseen part of the cabin... leaving Caroline to glow in the warmth of the fire pondering the meaning of the submission that she had just given. It was Einstein who once said that when a man is with a pretty woman, to him hours seem like minutes. Conversely if the same man sits on a hot stove, seconds seem like hours. That is the concept of relativity. To Caroline, the time that Phillip was gone seemed like days! On the one hand, she was concerned about turning herself over to him, yet on the other she longed for his touch. When he finally did return, she could not withhold her relief. A smile burst across her face. It was then that she realized that he carried something..... a flogger. It was the type that one sees in an old movie about pirates and sailing ships... the kind that brought so much pain and often death to the seamen on whom they were used. The blood pounding through her veins sounded like a drum-beat in her ears. "Oh no.. please... don't hurt me! I told you I will do what you want!" Once again Caroline's heart sank. Once again she was concerned for her safety. But once again something inside her coupled with his deep but reassuring voice calmed her fears. "My Dear... you moved when I had commanded you to be still. That breach cannot go unpunished. I now give you a choice, Caroline. You may accept your punishment and continue with the process of becoming mine, or you can refuse it and I will release you from your promise of submission. If you choose to be released, My Dear, that will be the end of US. Which will you have, the flogger or your freedom?" The choice was clear enough. No sane person would choose to be whipped rather than released from her chains. Yet the freedom that Caroline found in her restraints sealed her fate. As though it was another person responding for her... someone deep inside her... Caroline said, "I'll accept your punishment." With that, Phillip smiled... his eyes filling with tears of joy that made Caroline's heart soar. It was a new experience for her... feeling like this just because she could see the pleasure that she had given another. There was a wonderful warmth growing inside her. He brought her to her hands and knees and adjusted the chains in the bolts in the floor so that she was secured firmly. She could feel the soft leather of the flogger drag slowly across her exposed buttocks. The anticipation was sensual and she knew that she would endure the pain to please Him. "As I administer your punishment there are some things that I will teach you. First, when we are in private, you must always call me Sire." With that, he drew the flogger the length of her back. The tips of each leather strand gently caressing her skin, making it tingle. Caroline's Undoing "As you accept your punishment you will acknowledge each blow by counting it off.. like, 'One, Sire,' and, 'Two, Sire.' You will also tell me how much pain it brings you on a scale of 1 to 3. 1 will be very light and 3 will be, 'I can't take anymore.' Do you understand, My Dear?" Now the flogger was gliding between the cheeks of her ass falling strand by strand across her wet pussy. The sensation was intoxicating and Caroline responded as though she had always known that this was what was meant for her life. "Yes Sire." No sooner had the words escaped her mouth than her ass cheeks began to burn from the sting of each strand marking a line across her soft flesh from the first blow. "One Sire," she almost screamed. "That was a 2 on pain," she gasped. "Good," he said as Phillip began to give Caroline more and more instructions between each stroke. He quickly found the strength of the blow that would reach a 3 for pain and continued at that level stroke after stroke. His voice was soft and loving... he urged her on to accept more and more for him.... to learn from him... to come to him. Caroline struggled to absorb her lessons, but the burning pain was making it harder and harder for her to concentrate. Despite her efforts she drifted deeper and deeper into some place that she had never known; a place where the pain of the flogger was replaced by a sexual arousal like none other she had ever experienced. Just as her delirium made his words begin to vanish into the night, she realized that the flogging had stopped. Through her dulled senses she could feel him caressing her burning red bottom. The pain had given way to something else.... a euphoria... a buzz of sorts. She was only marginally aware of what was happening to her but she knew that once again she was aroused like she had never been before. His lips were soft and warm and brought great delight to her as they roamed over the red mark left by each strand of the flogger. Even as the flogger and now his mouth worked her bare ass, he was so caring that he had opened her heart to him. She wanted more than anything to have him... to please him. The lubricant was cold as his finger worked around the tight circle of her ass. Anal sex had never been something that Caroline had wanted to try. "It must hurt," she had always told herself. Now, though, knowing what was about to happen to her, she gave in. She felt her muscles relax as the spongy head of her new Master's cock slowly eased into her. With his hands on her hips, he guided her back onto him. And now she wanted it... she wanted all of Him... in any way that he would have her. She yearned only to please him. Her genitals were on fire as his pace quickened and his strokes lengthened. She had been brought almost to orgasm by the flogging and his kiss, and now screams of delight issued from her mouth as her cascading climaxes tightened her muscles around him. He was driving into her so hard now that she was almost losing her balance and with everything in her, she wanted him to cum. She wanted him to join her in the crashing orgasm that she was having. Before that could happen, Phillip withdrew from her, allowing her to collapse to the floor... panting and spent. CHAPTER 3 The Collar As she lay there breathless, she could feel the chains being released. Strangely, she was glad to feel the security of the cuffs still firmly about her ankles and wrists. "You have performed well, My Dear, and given yourself to me in every way that I commanded of you. Now it is time for me to accept you as my submissive. Do you understand what this will mean?" he asked. Still trembling, she shook her head no. His smile was warm as he helped her to her knees. She was there before him... naked... staring at his cock as he had instructed her during the flogging session. Using a pair of short silver chains with clasps on each end, he first chained her wrist cuffs together behind her back, and then her ankle cuffs. Her focus was still on his cock which was inches from her face as he worked. She realized how much she wanted him again... her nipples were once again hard and her pussy moist. She could feel the blood rushing through her labia, engorging the moist lips. Breathing in gasps now, she leaned forward to try to take him in her mouth... she wanted him so much. The subject of her attention began to stiffen as Phillip realized her desire for him. "Not yet, My Dear," he smiled as his hand gently guided her back away from his rapidly arousing member. He next fastened a wide black leather belt around her waist. It had silver rings front and back that matched similar rings on the sides. Through the side rings he passed two longer silver chains which attached one to each of the wrist cuffs. The other end he held in his hands. "Look up at me My Dear," his fingers gently raising her chin to meet his gaze. "It is now that you will become mine... for now and forever. This collar that I hold will be a symbol of your submission to me. You will wear it at all times in remembrance of your commitment to serve and service me in any way that I choose at any time that I choose. Do you understand?" "Yes Sire." "You will accept this collar only if you agree to do as I command. Only if you agree to submit your will to mine. Only if you agree to give yourself completely to me. Do you understand? "Yes Sire." "From this day forward, you will never again wear any clothing that in any way restricts my access to your pussy or your ass... do you understand?" "Yes Sire." "Every part of your being will be devoted to pleasing me...and you will, in turn, get your pleasure from that and from me as I see fit. Do you understand?" "Yes Sire." "If I command you to please me, even if others are present, you will drop to you knees and do as I ask, Do you understand?" "Yes Sire." "If I ask you to please another with your lips, or your pussy or your ass, you will do as I command. Do you understand?" "Yes Sire." Her mind was racing now. The thoughts of what she was about to do flooded her consciousness. All the while her juices flooded her. Somehow, from somewhere that she never knew existed within her, came the irrepressible urge to be his. To submit to him totally. This was all making her slightly dizzy as her heart pounded. So much so that her protective Dom had to place his hand on her shoulder to steady her. His touch burned her... his hand so hot... her skin shivered with delight at the feel. "To all of these things that I have told you, do you submit yourself freely, Caroline?" Knowing that at your request I will release you from your submission.... never to see you again." The thought of being released from his protective bonds drew a cold shiver from her. She WAS his now and she never wanted to be released. "Yes Sire." As he attached the soft leather collar around her neck, he finally said the words that she had unknowingly been longing to hear for hours if not all of her life, "With this collar, I claim you as mine.... mine to serve and service me as I wish... mine to protect and nurture you." With that, he guided Caroline forward to his now fully erect manhood. "Take it gently, Caroline and please me as you have pleased no other man." At long last, her lips touched the fleshy soft tip. Her tongue swirled in the pre-cum already dripping from him. Her eyes closed and she savored in the taste of him. His glorious cock was now her point of worship and her mouth caressed it.. engulfing the whole thing. Her hands tugged at the chains yearning to cup his balls in them... to stroke him into her mouth.. to hold his ass and pull him into her. As he began to pump into her mouth, he released the clasps binding her wrists together allowing her hands to move to him... constrained only by the chains through the belt rings. She devoured him now... needing him like she had never before desired or needed anything. Her nipples brushed against his thighs... her heart pounding... her breasts heaving... her pussy soaked. It was then that she felt him begin to tense. His hands wrapped lovingly around her head and with a voice that uttered as much of a moan as words he said, "Take my cum, My Dear.... it shall set you free in your submission to me!"