Sir Daddy Longlegs Chapter 1

Chapter One:



A Day of Firsts


A full moon appears through the ragged trees as clouds pass in the distance. A smattering of stars glitter around it. Thunder rumbles in the distance. There’s a smell of rain in the air and a chill envelopes the petite figure as it passes through the woods. She shivers in her thin and ragged dress as the wet branches smack against her. She struggles each time one catches her dress, tearing a little more from the rear of the dress, soon her bottom is as bare as her sore feet. Struggling to find shelter in the dark, she gropes around the side of a hill until an opening seems to appear out of nowhere.


The opening is very low, but large enough for her to be able to enter if she crawls, so dropping to her knees, she slowly, painfully makes her way in. After crawling for what seems like hours, but is really just a couple of minutes, she reaches an area where she can stand. Carefully, she pushes herself up as she tries to let her eyesight adjust to the dark. There seems to be a pale gleam in the distance. She makes her way towards the distant light, not paying attention to her surroundings. Suddenly what appeared to be a gleam in the distance, now starts to look more like eyes, two clusters of eyes surprisingly bigger than her own head.


Startled, she starts to move back towards the opening, still facing the two clusters. As she takes her fourth step back she feels something preventing her from retreating any further. Her hands and legs seem glued to what ever is behind her, the only thing that seems to not be tethered to one spot is her bare bottom.


He moves closer, as torches on the wall slowly come to life. One after another fill the room with their heated glow. Without even moving his head he takes in her appearance. She seems to be a young adult, perhaps just out of her teens. She’s shaking with fear as he approaches. Curly auburn hair trails down to cover her heaving breast, hiding them where the thin fabric can’t. Her large crystal eyes widen as she takes his form in. He seems to be a large spider with a human torso, two sets of arms and hands, and a strong appearance. His dark wistful hair grazes his shoulders as he moves looking her fully in the eyes. She can feel herself being hypnotized but cannot fight the desire she feels building in her. Her naturally submissive spirit and deep desire to be desired and loved come to the surface as his gaze fills her heart and soul.


“My name is Brian Longlegs, but you, my child, may call me Daddy Longlegs or Sir”. He barely spoke the words, but she felt as if he were speaking directly into her mind. “What is your name child?”


She gasps as she feels a cold leathery touch on her backside but is unable to turn to see what it is. “M… my name is Joseline… Sir…” she gasps as the leathery touch starts running up and down her cold bottom. “S… sir,” She stutters as the distracting sensations behind her are both odd and arousing. With one strong, firm, but kind hand, he reaches up and caresses her cheek.


“Are you cold baby?” He whispers in her ear. She nods as the leathery feeling starts lightly patting her bottom. “I can warm you up in several ways, young one. Some you will enjoy, even love. Others you will hate and despise with all your heart. For now, let’s start with a gentle and careful warming” He waves a hand and suddenly she is no longer bound to what ever was holding her. As she turns around to see what had held her trapped like that, the gleam of a sturdy spiderweb seems to dissolve faster than sugar in water.


Taking her hand, he leads her through an alcove into another area of the cave. “This my child is my home. If you choose, you may live here with me, but you must choose of your own accord, and only if you are willing to accept all the rules and consequences for breaking any rules. First, let me show you my home. The kitchen and living area is here. While I am naturally a carnivore, I fully believe in well rounded meals, so you can bet fruit and vegetables will be included with meals. I may be strict, but I am also reasonable. So, if you have a good reason to not eat something, we can compromise and find something that won’t be problematic but will offer the same nutrition.” She looks around, but it’s obvious she isn’t paying complete attention to what he is saying. “Young Lady!” he says sharply, catching her by the upper arm. He turns her to face him.


Unable to look up, due to fear, Joseline stands there shaking. A finger lifts her chin and makes her look him in the eyes. “Joseline, you need to listen to Daddy, so you can make an educated decision. If you are to live here, you need to know what is expected of you and what will happen if you break a rule. The first rule: always listen with respect when I speak to you. You don’t have to agree, but you must listen. The consequence for not listening, is a spanking on the bottom. Repeat offenses will require harder spankings, some of which may include implements. Other punishments may become a factor if needed. Do you Understand?” He eyes her, watching her take in the words. Slowly she nods. He turns her to one side and smacks her bottom, firmly, but not overly hard, twice then turns her back to face him. “What was that my dear?”


“Y… yes Sir, I understand Sir.” She reaches back and rubs her bottom. He takes her hand gently and leads her through another alcove into what appears to be a hallway. There are four openings. The first one on the right leads to a bathroom with a large antique style claw foot tub, a toilet that looked like it came from the 19th century, a pedestal sink, and a changing table with a hook high above the table holding an empty enema bag waiting to be filled and used. In a corner is a child’s potty only large enough for an adult. The potty looks like a teddy bear and the arms look like they would come around to hug the child/adult to keep them safe as they go.


She turns to look Daddy Longlegs in the eye only to see he’s watching her. “This is obviously the bathroom, but when you’ve been naughty, it is also a punishment room. Here I will bathe you daily, diaper you frequently, and when necessary, give you an enema. If you receive an enema for punishment, you will be spanked at some point during, after, or before the enema. Do you understand?”


Again, she nods, but she also whispers, “Yes Sir… Sir, what is an enema?”


Smiling, he pulls her gently to the changing table, then reaches up and pulls the hose and nozzle down to show her. He squeezes two different bulbs showing her how they inflate, which makes it nearly impossible for any water to leak. “When you receive an enema, and you will weekly, unless you are being punished, then you might receive a few within a week. An enema is when water, or some fluid, is inserted into your bottom to clean you out. Sometimes it is done for health and medical reasons, sometimes for punishment.” He grins mischievously, “There are some who actually enjoy receiving enemas too. Especially when other play is introduced during the enema.”


She looks at him confused. Her innocence shines through as he explains the enema, but when he explains enjoying it, she feels completely lost. “Little one, enemas can be considered foreplay or even part of a sexual experience.” Her eyes widen as he explains the concept. Her nose wrinkles like a bunny’s when he explains how the nozzle is pushed into the recipient’s bottom, the balloons expand, and water fills the bottom in question. She purposely turns to look at the tub, trying to distance herself from the enema and the changing table, but he turns her to face him instead. “If you receive a punishment enema, you will be diapered after you are finished expelling the enema and a final spanking is given. How long you are required to wear the diaper will depend on your behavior. Do you understand?”


Unable to look up at him, she nods quietly, then, almost as an afterthought, quietly says. “Yes Daddy”. He grins as he recognizes her acceptance of the rules so far. He lets go of her hand, so she can explore the room more. She moves to the tub and notices a small table next to the tub with a few children’s bath toys. She glances over at the potty and then the changing table, before looking back at the rubber ducky, toy boat, and some small water rings. She turns quickly to look at Sir Longlegs with a shy but intrigued smile. “Does this mean you expect to treat me as your little girl sometimes?” A grin appears on his face and a soft chuckle slips out as he sees she’s coming to understand what her role will be.


He approaches her slowly, so as not to startle her. “Yes, my dear, you will be my little girl, always, if you accept, but you will also be my big girl when we want a different kind of play.” She looks up into his eyes for the first time since being freed from the web. She looks both scared, but also full of desire for what he is describing.


He takes her hand and gently leads her to the room across from the bathroom. There is odd furniture here. There is what looks like a saw horse, but the padding on top, the straps on the legs and the one that obviously straps over the padded part of it intrigues her… She moves closer, reaches out a hand and lightly touches the soft fur padding of the horse. “That is a spanking horse little one.” He says just behind her, making her jump. He gently puts a hand on each of her shoulders and pulls her into him, back first. He lovingly wraps an arm about her waist and hugs her to him as he starts pointing at other contraptions explaining how they work. A spanking/fucking bench where several areas will be exposed when bound on it. A wall of different paddles, canes, straps, and floggers. A shelving unit displaying all manner of dildoes, vibrators, butt plugs, and other sex toys. All locked in “display” with glass doors and a gentle light highlighting them.


“I… is this for play or punishment?” She asks softly, still looking around the room. Her hands rise up to hug back the arms that so tenderly hold her.


“It depends on how you are behaving, it can be either reward or punishment.” As an after thought he adds, “it can even be both. Let me show you the last rooms.” He lifts her into his arms, carrying her as a small child and moves to the next room down the hall. As the light slowly flickers on, she notices a nursery for a small young girl, complete with a crib sized as if she were no more than 2. There is another changing table a few feet from the crib. In one corner is a tall stool with a weird look to the top of it. He sets her down, so she can explore, and she immediately moves to the stool. The top looks odd at first until he approaches and shows her the center is removeable. On the wall next to the stool is a selection of stool tops. The one currently on the stool looks like your average flat top, while the ones on the wall vary from having a small protrusion that would certainly push into one’s bottom, to large flanges that would definitely not just push into but force its way deep into a naughty bottom. Some of them are smooth but some have small bumps which would make having them inside one’s bottom even more uncomfortable. Then she notices that there are two identical stool tops for each type of protrusion. One has a flat surface surrounding the flange, the other has what looks like a jagged, meat tenderizing surface, random sizes and textures for each point. It’s obvious this would be uncomfortable if not painful to sit on, especially on a well spanked bottom. She turns again to look up at him, noticing that he seems taller, or bigger, than in the other rooms. She pushes her head back further, so she can really look up at him. “There’s a special spell in here little girl. In here you are no bigger than you would be if you were two years old. While technically, you would still be an adult, here you are no more than two. You will be treated as a child for the most part when in here. These stool tops are for corner time. If you’ve been only slightly naughty, you will get a top mild top that doesn’t have any protrusions or tenderizing abilities. The naughtier you are, the more severe the top. When being punished here, you will spend some time in the corner before and after a spanking. You may also ask for some corner time, if you feel a need for some time to think. Those times will only have a spanking included if asked for. You may always ask for a spanking, even when not earned. When asking, you may ask for a hard spanking or an erotic spanking. Depending on the kind you ask for, you will either receive sexual play during and after or not.” Joseline looks away blushing and biting her lip. He can tell she wants to ask a question but is afraid to. “No, young one, an erotic spanking will never take place in here. Though the corner time stool is also in our bedroom for both discipline and fun, the seats get much more severe and extreme than they do in the nursery. In the bedroom, the flanges are doubled one for your bottom hole and one for your vaginal hole.” She blushes again and covers her face with her hands, both embarrassed and deeply aroused. He kindly pulls her hands off her face and picks her up into his arms. She can feel the love pulsing in them, even as she wraps her arms around his neck like a young child would. He turns around and shows her a wall that has an odd all white look to it. He moves her closer to it, so she can touch. When she does, she realizes it feels like construction paper.


“Here, and only here, may you color, draw, paint or what ever you choose to do on the wall. When it is full, or you feel it is finished, let me know and I will replace it. I will hang your artwork where I can see it all the time in another room attached to the master bedroom. Now, would you like to see the bedroom my darling girl?” Some how her thumb had made its way into her mouth as he was describing what she could do on that wall of paper. She nodded when he asked about seeing the bedroom, but quickly removed her thumb to speak what she was trying to say with her head.


“Yesh pwease Daddy” slipped out. She looked in horror when she realized what she’d said. She tried again. “Yesh pwease Sew”. She looked at him with terror. He hugged her close, hiding a chuckle.


“It’s ok Babygirl, when you are in here, you can only talk in baby talk. It won’t take affect immediately, but quite quickly. In here, only little baby girl talk is ok. If you say or try to say something that a little girl shouldn’t say, it will come out as gibberish. If you cuss or swear, that will be punished no matter where you are. Never is it allowed, even if you are being a big girl, except during sexual play. Is that clear?” He watches her as she takes in both what has happened with her speech and what he’s just said.


Nodding as she thinks, Joseline contemplates her normal vocabulary to what will be expected of her here. “Yesh Sew, I tinks I understands.” After a moment she nearly whispers, “My bum bum is gonna bes bewwy sores.” Subconsciously, she reaches back and rubs her bare bottom as it still peeks out from her torn and tattered dress. He turns with her in his arms and together they move out into the hall again. Joseline feels a weird sensation seem to slip off her. Quietly, thinking he can’t hear, she whispers, “Holy Shit, it really does change me going in there.” She feels an arm around her tighten. She quickly glances up and sees a firm, flame of disappointment flash in his eyes, without another word he turns and moves quickly to the master bedroom. Before she has a chance to look around or say anything, she finds herself over one of his spider legs. What remains of her dress is quickly pulled off her as it seems to fall away in pieces.


“Cussing is not allowed in this home. While you have not agreed to be mine, and to the rules and consequences here, I will show you a small amount of what to expect if I ever hear words like that from you again.” Suddenly her bottom explodes with pain as hand after hand lands directly on her sit spot. She turns her head to look back to see what is causing such intense pain. Looking over her shoulder, she sees that his two right hands and spanking, more quickly than an average man with only one right hand would. She can feel the hard form of his hand from working with tools. After a few more swats, her hand flies back to try to protect her bottom, one of his left hands grabs her wrist and pins it in the small of her back while the other turns her to look at his face. “This time you will only receive 20 swats. In the future, you can be assured any cussing will receive a spanking with a paddle, time on the stool and a good mouth soaping. Do you understand little girl?” His eyes blaze as the swats keep falling. Suddenly as quickly as they began, the spanking is over, and she is turned over to be cuddled. She snuggles into him, though she hadn’t cried during the spanking, being cuddled, forgiven, and loved afterwards was completely new to her. This broke the wall and she clung to him crying her little heart out. She knew, she just knew this was not only where she wanted to be, but where she truly belonged.


When her sobs finally slowed, and her breathing was again under control, she pulled back just enough to look up into his eyes. “Please Sir, please Daddy. I want to be your little girl, now and forever. Please love me and let me love you. Let me be yours. I don’t know how I got here, but I don’t ever want to leave.” He pulled her back into his check and hugged her tight. He kissed the top of her head before standing her in front of him.


“Do you mean that little girl? Do you accept the consequences and the rules? Do you understand that I will be the one in control at all times?” Wordlessly, unable to speak at the moment, she simply nods and falls into his arms again. He hugs her once more, then pushes her back a small amount. “Then we need to finish your punishment, don’t we little girl?” Joseline’s eyes widen, but she nods, unsure if he means another spanking, a mouth soaping, or the stool. He leads her to the corner where the stool waits. He removes the plain top and puts a slightly more severe one with two phalluses both about an inch around and half an inch long, onto the stool, reaching under to lock it on. Then Daddy picks his big little girl up and puts her onto the stool seat, the two phalluses push firmly as though to enter her bottom and vagina. She gasps as she feels them push, fearful they will deflower her, but as if he’s reading her mind, he leans down. “No Babygirl, I want that for myself. This will just remind you of who you belong to and why you are here.” Then he pulls a strap up and over her lap. Buckling it on the other side, she is effectively locked into place. Then he turns back to the shelves and picks up an hourglass. Showing it to her he speaks quietly. “This will tell you when your time is up, this is the shortest one in this room. You will sit here for five minutes then I will help you off the stool. I don’t want you to try to get up before then. Is that clear?” Joseline wimpers but nods, not sure what to say. The look in her eyes is clear that she doesn’t want to be alone. “I’m not going far little one, just far enough that you can think about why you are here.” With that he sets the hourglass down where she can see but not touch it and moves to a comfortable velvet covered chair to watch over her incase she gets into distress. He makes sure that if she turns her head to look, he will be the first thing she sees.


Joseline covers her face and quietly cries, feeling sorry for being naughty, but also feeling scared that she won’t be able to be good. She shivers in the cold but doesn’t move, except her shoulders shaking from her quiet sobs. Gently a warm blanket seems to wrap its-self around her, she glances up to see Daddy there, wrapping his Babygirl in a warm blanket and his arms around her, hushing her softly. He glances at the glass, “just a little bit longer baby. Can you hold on, or do you need your Daddy?”


Joseline bites her lip. She wants to make him proud, but she wants her daddy so much. She looks up, “I can wait Daddy. I’m sorry I was naughty, I didn’t even realize I’d spoken until it was already out.”


At that, he grabs the glass and lays it on it’s side back up with the other glasses. Quickly he unbuckles the strap and carefully pulls her up and off the phalanges. Hugging her tightly to him, he carries her to the bed and lays her on it bottoms up. He then opens a drawer in the nightstand and pulls a jar of healing and cooling salve out and opens it. Carefully and gently he applies it to her already cooling bottom. Then, after putting the salve away, he climbs into the bed on the other side and pulls her into his arms. He cuddles her to him. “How innocent are you baby?” He asks in her hair as he inhales her scent. She looks at him confused. “Have you ever experienced a man inside you, either vaginally or anally?” She shakes her head. “Have you ever experienced a toy inside you in either place, beside being on the stool just now?” She again shakes her head. A large, slightly naughty smile pulls at his cheeks. “Then I shall teach you all the joys I can, if you will allow me. If you don’t like or don’t want to do something, all you must do is say ‘No thank you Daddy’ and I will respect your request. The only time that won’t work is if you are being punished.”


Joseline’s eyes widen, but she nods in acceptance, suddenly a firm hand smacks down hard twice on her already sore bottom. She gasps then wimpers and says, “I’m sorry Sir, I mean I accept your rules and your guidance.”


Slowly Daddy Longlegs moves in and softly kisses her on the lips, slowly he deepens the kiss, letting her get used to the feel, and the sensation. As the kiss deepens a light almost feather like touch moves over her chest and down to her left nipple. She feels his finger start to lightly pinch and twist it. She feels as the intensity starts to build. The pinching and twisting slowly gets more extreme. Her back arches pushing towards his hand, silently begging for more. She moans softly around the kisses she is now placing all over his face and neck. He slowly and gently drags the tips of his fingers down her body and gently cups her sex. “This, my pet, is mine. You may not touch without direction and permission, except when cleaning yourself.” His other hand moves to between the cheeks of her bottom. He lets his finger lightly tease the rim of her opening. “This too is mine, sweetheart, if it needs cleaning, you must ask me to do it. I do not want you touching it at all.” He gently pushes his finger as though to enter. “Do you understand me?” Her gasp and low moan is all that escapes her mouth. Slowly his finger pushes a little more firmly and slips just a little into her bottom. She squirms and moans again. “Answer me baby or I’ll spank you instead of play with you.”


“I… I understand Sir,” she gasps out and squirms again. “Oh… please Daddy… oh…” His finger pushes in a little further as his other hand cupping her moves to slip a finger into her soft tender opening. His finger searches for her hymen and soon he feels the resistance. He pushes gently but firmly, trying to let her adjust and to keep any pain to a minimum. A tear slips down her cheek as she moans. She can feel his finger twisting and moving in and out of her bottom, which feels oddly good. But she can also feel him pushing inside her tender sex and feels an almost pain there. She doesn’t know why but suddenly she arches her back forcing his finger deep inside, breaking the hymen quickly. The pain is overridden by the joy and pleasure she feels as his finger starts moving in and out of her. A second finger seems to slip in next to the first, his other finger still entering and withdrawing only a couple of inches in her bottom. Suddenly she feels a sharp but pleasant jolt of pain. Looking down, she sees he’s latched onto one of her pert nipples with his teeth and is gently but firmly gnawing on it. He adds a little more pressure to her nipple as he pushes a second finger into her bottom, pushing them both all the way in quickly and forcefully. She cries out with a deep pleasure. Never has she felt such joy. His fingers seem to bend into a hook in her pussy. Finding that sweet spot she new nothing about. She elicits a low growl of pleasure and desire. She knows she wants more but doesn’t know what more. Oh lord, she is too new to this, she thinks. As she opens her mouth he stops his teasing play and moves between her legs as his fingers in her pussy withdraw.


“It is time for me to claim you my little one, are you ready?” Without waiting for a response as her body tells him everything. He quickly and firmly thrusts his member deep into her. Her gasp and wide eyes quickly fill with lust and desire and as he moves, she moves too. It’s likes a special, private dance for just the two of them. With each thrust he makes into her, his fingers in the back make the same movement. As his hips move faster, his fingers move faster, he can feel her gaining momentum towards her first orgasm. He feels her pulsing around his member and his fingers. Suddenly he withdraws, a sigh and moan slipping out of her as he stops. He kisses the tip of her nose, then gently turns her over onto her tummy. His hands start to gently rub and massage her shoulders, back and bottom. As two hands reach under her and start teasing her tiny pleasure button, his other two hands spread her bottom open. Using her juices as lubrication he pushes the tip of his member against her rosebud opening. “I’ll take this slowly sweetheart, but it may still hurt.” Slowly he pushes in, whispering to her, telling her to relax her bottom, enjoy the sensations, and just let it happen. She almost doesn’t notice him entering her at first as his other fingers work magic on her little clitoris. He pushes further and further into her, increasing the intensity on her clit as he goes. He hopes to remove most of the pain this way. He feels her stiffen as he pushes into her completely, at first, he thinks she’s in pain, but then realizes the howl she’s making is from her first orgasm, an explosive orgasm at that.


“More…” she whispers, unable to say anything else. Taking the hint, he starts slowly withdrawing and re-entering her bottom a little at a time. The speed and depth slowly increase. Her bottom rising up to meet each thrust. As one hand continues to work on her little nub, the other pushes now three fingers into her tender love maker. The hover at the opening for just a moment before quickly forcing deep inside, the movements of his fingers inside her mimicking his throbbing manhood in her bottom. Soon he is pounding both into her as he starts to allow himself to relax. His orgasm starts to build as another builds within her. Soon the waves of pleasure over run them. She feels him pulse inside her, filling her. He feels her muscles pumping him, pulling him in deeper. They both cry out in immense pleasure as he collapses on top of her. He starts to withdraw, but she begs “Please, don’t leave, don’t stop… stay in me… please Sir, please Daddy.” His heart melts and wrapping his free arms around her turns them both onto their side, his manhood and fingers still inside her. He kisses the back of her neck gently.


“Did you like that pet? Was that a good first experience?” He waits for a response, then realizes as he listens to her soft breathing, that she has fallen asleep. He chuckles softly, draws her closer and slips off to sleep with dreams of her in his mind.

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