A New Path

Part Three

Once again, Sheri's wrists and ankles were restrained, the pillow placed under her hips to elevate her perfect little ass. Chris left the room for a minute, and returned with a leather blindfold. It was basically two round eye patches, each coated in a soft material, with a black leather strap holding them in place. When on, and snug, not only could Sheri not see, but also the light pressure exerted on her eyelids prevented her from even opening her eyes. This added to her sense of dread, and Sheri was having doubts as to her ability to do what Chris had requested.

“Sir, I am not sure I can do this. I mean, can I take it? Will you be gentle with me?” She asked, tears welling up in her covered eyes.

“Of course I will be gentle at first dear, I do not want to injure you. As for can you do it, well to be quite honest, there is nothing to do. You are restrained, and soon, will be gagged. Once I begin, you simply lie there, and get fucked. In this moment, I will be using your body for my pleasure, and not for mutual satisfaction. You have received your orgasm, and now it is my turn. You either chose to please me this way, or chose to leave, and discontinue our association on this level. But you must chose, and chose now.” As he spoke these words, Chris had opened a tube of KY jelly, and was liberally coating two fingers with the clear, slippery goo. He reached down, sitting beside the prone submissive on the futon, and began to massage the lubricant around the outside of her tight, virgin anus. Sheri whimpered at the touch, but as he put a finger inside, the sensation was both alien and exciting at once.

This was the dirty place. You didn't have sex there; you shit from there, so why would a man want to fuck that dirty place? Wouldn't he rather have my pussy? That's what all guys want, right? But not this guy; Chris had said he wanted her ass, and now, it was put up or shut up time. Ever since her first sexual encounter, Sheri had wanted to please. She never knew why, or what that meant, just that it was very important to her that her partner enjoyed himself. Her difficulty in reconciling this in her own mind stemmed from her mother's teachings. Since she was old enough to know what sex was, it had always been preached that sex was ‘dirty', and something only done between married people. Her mother's religious convictions, though not shared by Sheri, certainly had left a lot of conflict in her young mind. The submissive personality type constantly warred with the voice in her head, her mother's voice, telling her it was dirty. One very distinct memory was from 8 th grade, a girl in Sheri's class was telling a story in the bathroom about catching her older sister giving a blowjob to her boyfriend. Although Sheri gasped, and giggled with the group, it was to mask her discomfort at not knowing what a blowjob was. That night, she had asked her mother what a blowjob was, and was surprised at the reaction she got.

“I don't ever want to hear you talk like that again. Only perverted men enjoy those things, and only a whore would allow a man to treat her that way. Now go to bed.” With that, she turned out the lights, and slammed the door to Sheri's room, leaving her daughter confused and upset. Weeks later, Sheri finally asked her friend Terri, the one who's sister had been the subject of the story, what a blowjob was. Though it didn't sound appealing, having a boy put his penis in your mouth, Sheri was not disgusted, and actually found the notion quite exciting. Part of her wanted to rebel and do exactly what her mother had said was dirty. Still, Sheri had never been able to get that voice out of her head, and even when being with boyfriends in the past, could never get comfortable doing anything other than vaginal sex. Always, it was her mother's angry voice, calling her dirty. Now here she was, about to allow a man to do something she believed to be very dirty on their first time together.

Chris had his second finger working into that tight canal, and was moving them in and out gently, twisting slightly, trying to get her muscles to relax a bit. “You have to chose now dear.” Chris said, removing his fingers to apply more lubricant. Sheri was not completely ready to surrender her ass, and had a lot of concerns, but she was more afraid to lose the opportunity she had with Chris. Here was someone who understood her need to serve, and despite her discomfort, had made her cum like mad even while she was uncertain. It was like a drug, and she needed more. “Yes Sir, I will do it.”

Sheri could not see the pleased expression on Chris' face. He was fighting mixed emotions as well in that her wanted this girl so badly, and saw so much potential in her, but she was so raw, and Chris was uncertain as to whether he wanted to commit the amount of time necessary to teach her what she needed to know. Part of him had been pushing her hard all night, trying to scare her off, make her quit, and now, she had submitted to his last demand of the evening. While he was going to thoroughly enjoy fucking that tiny ass, Chris had no illusions that this was going to hurt like hell for Sheri, and she would be a weepy mess when he was through. Maybe that'd make her run.

“Once I begin, I will not stop until I reach orgasm, do you understand this?” Chris asked, straddling her slender thighs, and rubbing the remaining KY onto his swollen cock.

“Yes Sir, I understand.” Sheri said meekly, and tried to calm herself, to relax her muscles so the penetration would not be so uncomfortable. Chris told her “Open your mouth” as he put the ball gag back against her lips. Sheri hesitated for just a second. ‘If I have this in, I can't tell him if it hurts too much, or ask him to stop. But he already made it clear; he doesn't intend to stop. Ok, I can do this.'

Sheri opened her mouth, accepted the gag, and Chris buckled it in place securely. Kissing her between the shoulder blades, Chris pressed the head of his cock against her puckered asshole, and Sheri whined a bit through her nose, anticipation of what was to come was making it difficult for her. Then the pressure began to increase, and despite her best intentions, Sheri's body instinctually clamped down for all it was worth. Chris frowned, and increased the pressure. He knew there was no way for her asshole to stop the penetration, especially as well lubed as she was, but understood that by fighting, she was making it difficult for herself. “Relax little one,” Chris advised “it's going in either way, and fighting only makes it harder.” Sheri tried to relax, but her body was clenching involuntarily, and the pressure was going from uncomfortable to painful. Then, the sphincter muscle yielded to the intruder, and the head of Chris' cock popped through the ring of her asshole. Sheri's whine became a long drawn out squeal, while Chris sighed “Yeah….that's better.” Giving her a couple seconds to accommodate his size, Chris began a slow, steady push deeper into her bowels. ‘God, this little bitch is tight! I can feel every muscle in her body squeezing me right now. She's like a velvet glove.' Sheri, on the other hand, was not experiencing such a wonderful sensation as that which was wrapped around Chris' cock. She was in pain, and felt like her asshole was splitting in two. ‘He's killing me! Oh please! I can't take this, stop.' her mind screamed. But what came out of her mouth was “MMMPPPHHH!” She was shaking her head from side to side, and pulling frantically at the restraints, all of which only had the effect of tightening her grip on Chris' cock further, and stimulating him all the more. Visually she was more appealing by the second. The defined muscles in her back, arms, and shoulders all standing out as she fought the restraints, the thin sheen of sweat building up on her skin from the exertion, and the black leather of the blindfold, gag, and wrist cuffs against her pale skin all combined to increase Chris' excitement. Finally, after it seemed to Sheri that she was stuffed beyond her capacity, Chris was fully inside her. He held still, and murmured encouragement and praise to her, while telling her to relax, and breathe. Slowly, her body became used to the large tool stretching her anus, and she stopped straining against the restraints. Then Chris pulled back out, and Sheri went apeshit! She felt like he was pulling her guts out through her ass. She screamed long and hard into the gag, but only a muffled trill came out. Sheri tried to lift off the bed, preventing Chris from pulling out, but the restraints kept her firmly in place. Chris was in heaven. As good as it had been penetrating her asshole the first time, the reverse stroke, and the suction being applied by Sheri's ass to keep him inside was amazing. He pulled out until only the tip of his cock remained inside her, took a second to look down at her tiny, horribly distended anus stretched around his cock, then plunged back home to his full length. The force of this penetration knocked the wind out of Sheri, and she couldn't believe the pain in her bowels. It felt like she was on fire, and she was sure Chris had ripped her severely down there. He was not hammering away with vigor, every thrust slamming painfully home, every retraction made her feel like she had to take a shit. Sheri was sure she was making a horrible mess, and even through the discomfort, that thought mortified her. She could feel his passion growing, he was moaning now, growling in her ear, and biting the back of her neck. His sweat and smell enveloped her. Very male, strong, but not offensive, it combined with her sweat, the smell of sex, and lubricants, and the leather restraints. Sheri found it quite intoxicating, and noticed, as Chris became more and more excited, she was also becoming aroused. She was aware of a dampness spreading between her legs, and began to push her hips back, despite the pain, which made her grimace, to meet his every thrust. She was grunting through the gag with the effort, and Chris growling became one long animal howl as he thrust deep, held still for a moment, then exploded. Sheri felt the flood of hot sticky cum in her bowels, felt his cock throbbing in her asshole, and felt Chris sigh as the tension left his body. She smiled to herself; happy to have satisfied him despite the pain she was in. ‘So this is how it feels to be submissive during sex.' she thought, feeling a bit dizzy as the endorphins and adrenaline in her system suddenly had no place to go.

Chris reached down between Sheri's legs, and felt how wet she was. He chuckled to himself, as his fingers began to explore her sex. Initially, she didn't react to his touch, but when he found the swollen little bud of her clit, Sheri jumped about a foot off the futon. Chris didn't waste any time with her, just worked her clit hard and fast, his semi-hard cock still in her ass. She started moaning, and trying to say something through the gag, but Chris couldn't make it out, and didn't care what it was. She was shaking her head ‘no', but all the while was grinding her hips into his hand. It didn't take long, and Sheri found herself swept away in an orgasm that was crashing around her. “Go ahead dear.” Chris whispered in her ear, and go she did. Once again, Sheri bucked and thrashed as she came. At one point she thought she was going to pass out from the intensity of the orgasm she was experiencing. Wave after wave, she came, screaming and biting the gag, until she was exhausted. Even after it had passed, Sheri's body trembled for several minutes. Chris slowly pulled his cock out of her sore, stretched asshole, and left the room. Sheri just lay there, in a state of bliss, and listened as Chris ran water in the bathroom, urinated, and cleaned himself. Then he came back into the room, and undid the ankle restraints, followed by the wrist restraints. “Kneel.” He told her. Sheri came up to a kneeling position on the futon, and started to put her sore arms behind her back. “No, just relax and stretch those a bit. Tilt your head forward.” Sheri did, and he released the buckle on the ball gag, pulling it free of her mouth with an audible ‘pop'. Sheri worked sore jaws back and forth, then swallowed, and said, “Thank you Sir.”

Chris smiled, and replied, “You're welcome. Here's a tissue, blow your nose.” Sheri did, making yet another honking sound. This produced an awkward giggle. “I must look like hell Sir.” She mused, sheepishly. Chris looked at her, and it was true. Her hair was tangled and matted with sweat, her face was puffy from crying, she had eyeliner running from underneath the blindfold, and her nose was red. She looked pretty ragged. “Nope, not like hell at all.” Chris answered; taking her used tissue, and helping her off the futon. “You look like a sub who has worked hard to please a dominant dear, and that makes you look beautiful.” Chris led the still blindfolded sub to the bathroom. “Turn around, sit down dear.” Sheri did, and Chris reached behind her to undo the blindfold. “Keep your eyes closed, then open them slowly. You have been in the dark for a while now, and they will be sensitive.” He advised, pulling it away from her head.

Sheri rubbed her tired, itchy eyes. They felt puffy from crying, and she began to squint as she opened them a bit, allowing them to become accustomed to the light. She was not sure what she'd see on Chris' face, and that thought made her nervous. Would he be stern, or disappointed with her? Would he be pleased with her efforts? She became accustomed to the light, and cautiously, Sheri looked up at Chris. What she saw warmed her heart. His face reflected satisfaction and caring, and he was smiling at her. He saw the relieved expression melt into tears, and quickly reached out to embrace her, pulling her tightly into his chest and stroking her hair. Then slowly breaking the embrace, Chris kissed her forehead, and said “Go ahead and use the bathroom, I am sure you're cramping up a bit right now.” Sheri nodded, and waited for him to leave the room, but instead, Chris retrieved a washcloth from the cabinet, and began to run warm water in the sink. Noticing her still staring, Chris turned to face her.

“Sir, may I have a moment please?” Sheri asked, grimacing as her need to relieve herself became more urgent. “No, you may not. You have no privacy with me, no modesty. Is that clear? You have to un-learn a lot of bad habits, and the need for your own space as to avoid embarrassment is one of them.” With that, Chris turned back to the sink, and began cleaning his cock with the warm washcloth. Sheri sat there, mortified, for a minute or two. ‘Yuck! He's going to be in here when I go? I can't do it with him here.' But she could, and her body was taking that decision away rapidly. Finally, with a loud squirting noise, her body expelled any remaining waste, combined with sperm and lubricant. Chris never looked back at her, or made any comment, only finished cleaning himself, and rinsed the washcloth thoroughly, but Sheri was humiliated all the same. She turned bright red, but managed to finish the task. Before he left the bathroom, Chris turned and said, “Use this cloth to clean yourself, then come into the living room.”

Seated, with a fresh cup of coffee, Chris was waiting patiently when Sheri made her appearance in the living room. She approached Chris, and without being to, knelt in front of him, hands behind her back. Chris smiled a bit, and then passed her a small black journal, and a pen. “This is yours, dear. In it, you will record all instructions I give you, the date it was given, as well as my rules for our continued relationship, and the consequences of any deviation from my rules. You are to keep it with you at all times, unless I dictate otherwise. Failure to have it with you will result in immediate punishment. Do you understand?”

Sheri took the journal, and looked Chris in the eyes. “Yes Sir, I do. May I ask a question Sir?” Seeing Chris nod his approval, she continued. “Why do you not want to be called Master, and how should I address you in public. For instance, should I call you ‘Sir' at school?” Chris took a sip of his drink, and then answered carefully. “I do not have you call me Master at this time, since I have not committed to making this a long-term relationship. Once I am certain you are trainable, dedicated, and serious about this process, and that it is not just a fling or some experimental phase you're going through, then I will offer you a collar. The collar is symbolic of our commitment to one another as Master and servant, much like a promise ring symbolizes a continued commitment, and a desire to move forward. At that time, I will be addressed as Master.” Chris paused a moment, allowing this to set in, then continued. “As for addressing me in public, for now, let's keep it simple. Just call me Chris as always, but understand that if I tell you to do something, I expect you to make it so. I will respect your right to keep this part of your life out of the public spotlight if you do the same.” Sheri nodded her understanding, and Chris went on. “Good, now a few things to put in your journal.”

Sheri uncapped the pen, opened the first page of the leather bound book, and awaited her instructions. “First, a few rules. #1, always keep your pussy and asshole shaved freshly. I don't want stubble, or one ounce of hair on that region. #2, refusal to follow any command will result in termination of our relationship. #3, Clean all penetrations. If I am fucking you, and pull my cock out, I expect your mouth wrapped around it. #4, be on time, and never embarrass me through your appearance, attitude, or enthusiasm. Others may be present as you are being trained, and your performance is a direct reflection on me as a Dominant. Make me proud, and life will be simple. #5, be gracious, willing, eager to please, and attentive to detail at all times. Attitude is often more important than performance. I do not expect you to do everything perfectly, just that you give your best effort always.” Chris stopped, and waited until Sheri had finished writing. She kept staring at the page for a moment, expecting more, but Chris told her “Look at me.”

Sheri looked at his face, noticing he was a bit more serious now. ‘He's teaching.' She thought, ‘and he is more intense, more in character when he is sharing information with me.' Chris studied her for a moment or two and then asked, “Do you have any questions about the 5 rules I have given you?” She bit her bottom lip, a trait Chris had began to notice she did when she was unsure of what to do next, then found her voice, and asked a question. “Yes Sir, #3, clean all penetrations…” Her voice trailed off. “Yes, anal or vaginal. I will look at what is going on, and determine if there is too much mess to have you perform this task, but you always assume you will be sucking and licking me clean. This is further incentive to keep yourself very clean.” Sheri swallowed hard, and despite her best efforts, Chris could see the disgust on her face. ‘Good' he thought, ‘she is concerned about that portion of the training. Now I have something to motivate her with.'

Chris stared at Sheri. “If there are no further questions,” she nodded no, “then I have a few tasks I want you to accomplish before our next meeting.” Sheri picked up the pen again. “First, on Monday, make an appointment to get on birth control. As fun as it would be to fuck your delightful little ass every time, you'd get pretty sore, and I do like pussy. Secondly, go to the adult toy store on 56 th street, pick up a flesh colored dildo that is the approximate size and shape of my cock. I want you to bring it with you to our next encounter. Are these both clear instructions?” Sheri looked up from the page. “Yes Sir.” Sheri looked at the clock on the living room wall, the time was 12:14 pm. Sheri was expected to go shopping with her mother first thing in the morning. “Sir, will I be allowed to go soon, I have to be awake early.”

When she looked back at Chris, he had on that wolfish grin she had already come to love and dread all at once. “Oh, you will be awake early dear!” Sheri noticed his cock was semi-rigid, and growing rapidly. “Now, before I loosen that ass up a bit more, let's work on your oral technique a bit.” Sheri crawled forward, thinking how this was going to be a long night, and took his stiffening cock into her mouth. Little did she know how right she was.