Poer Loser

Princess,

You were very bad on our last date. It's time you learned who's in charge while we're together. This Friday I will have a friend drop off a package after your parents leave for work. In that package will be several items, there will be instructions for the use of each one. All of those instructions must be followed implicitly or you will be very sorry. Other than what's in that box, all you will have on is your coat from last week. Stretch out your ass more than you did last week, that's just a suggestion, but I'm sure you'll regret it if you don't. Be at my house at 5pm exactly. Do not be late.

Your Lord and Master

Allison bit her lip. That did not look good... she went to the bathroom and masturbated, forcing herself to fit two fingers into her ass as she did so. Her orgasm was better than any since the past Friday.

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In the morning, Allison woke up to find her parents gone. Outside the front door was a large brown box with her name on it. Quickly she picked it up and carried in inside, heading straight for her room where she opened it. It was full of ziploc bags, each one had something inside it along with a piece of paper that had written instructions.

Three clamps that looked like tweezers with a thin band around each one, they were connected by a chain shaped like a 'Y'. Two balls, connected by a string, one ball had another string hanging from it that was attached to a small plastic ring. When she picked the balls up, it felt and sounded like there were more balls rolling inside of them. The pair of handcuffs made her insides shrink in dread of what those could mean. Two items left, she picked up the smaller one since it was mostly on top of the other one anyway; it was some kind of gag, with a small penis looking pacifier type thing. She made a face and then pulled out the last item, and gasped in horror. It was obviously some kind of plug, and she had a horrible idea of where it was supposed to go. Easily the largest thing in the box, it looked it's thickest point looked even wider than Todd's dick, and it was very heavy and round. The black color made it look even more frightening.

Pulling out the instructions, hoping she was wrong, it became pretty obvious that she wasn't. Looking at the black monster with a sinking feeling in her stomach, she decided that she'd best start trying to stretch out her ass if she was going to fit that thing into it. Going into her bathroom, she rummaged around until she found a large tub of vaseline; she usually kept it to rub on her feet when they became dry and cracked in winter. Now it was going to have a new, much less innocent use. Greasing her fingers, she got on her hands and knees on the bathroom carpet, the blue shag keeping her from the coolness of the tile. Carefully she fitted one finger into her ass, it slid easily after all the practice she'd had the past week of two fingers. Slightly encourage she slid the second finger in, and moved them in and out of her ass in unison, the slickness of her fingers made the sensation rather pleasant. After a few moments of enjoying the naughty feeling of fingering her own ass (she still couldn't quite get it out of her head that putting anything in her asshole was dirty and wrong), she pulled them out and began to push three fingers into her ass.

Wincing a little as the tiny hole stretched open, at least it wasn't a sharp pain, just a little bit of burning which quickly started to ease as her slick hole adjusted. Panting a little, she worked her three fingers in and out, trying to spread them a little to prepare herself for what came next. Giving herself plenty of time to adjust to three fingers, and even begin to enjoy the feeling of fulness a little, she began using her other hand to play with her clit, letting her face rest on the soft carpet. Blushing a little, she thought about what she must look like with her ass high in the air, three of her fingers shoved in it while she played with her little clit. Grimacing a little, she began working her pinky in alongside the other fingers; it was starting to hurt again, so she squeezed her little clit to take her mind off the pain. With four fingers buried in her ass, she was starting to feel a buzz in her pussy as she mimicked the anal sex act. She continued to work her clit until she had a small climax, her ass totally adjusted to the invasion of her hand.

Picking herself up from the bathroom floor, she glanced at her watch. 1 o'clock. She ran downstairs to eat lunch, and then came back quickly, she didn't want her ass to close up too much after all that effort of trying to keep it open. Grabbing the big black plug, she brought it into the bathroom with her and looked dubiously at it. It looked an awful lot bigger than her fingers. No way to know without trying though. Liberally, she spread Vaseline over the entire bulb, making sure it was coated with the stuff. Then, getting into her position on the floor again, she used her four fingers to grease her asshole, stretching it out again before trying for the real deal. After her ass was coated in Vaseline and had adjusted to the width of her fingers, she took the plug and began easing it into her asshole. She managed to get a good portion of it in before it started stretching her asshole too wide, it burned with the effort to accommodate the plug; panting, she had to let it slide out a little bit. Determinedly, she began to work the plug back and forth in her ass, trying to get her asshole to work up to stretching out over the large part of the bulb. Slowly, she managed to get a little bit more into her ass, but it still felt like her ass was just never going to gape wide enough to get the whole thing in. A little desperate, she tried to just shove it in, despite resistance, and screamed in pain as her burning ass felt like it was going to split open completely. Sobbing, she let the plug slide out again, and her tears fell onto the soft carpet as she recovered.

Sniffling a little, she picked herself up off the carpet. Maybe a new position would help. Rubbing the Vaseline into her sore ass gingerly, she inspected the large plug. From the way the Vaseline on it looked, she'd almost gotten her asshole over the widest part... just a little more and she would have had it in. Wincing at the memory of the pain, she sighed and looked at her watch again. Dammit. 3 o'clock. In an hour and a half she had to leave to get to Todd's house, and she hadn't done anything more than try to get this stupid plug up her ass; she didn't even know what to do with all of the other items because she hadn't taken the time to read the instructions yet! Frustrated, her hazel eyes sparking, Allison put the plug point upward on the toilet seat. She'd just let gravity do the work for her.

Sitting so that the tip of the plug was at her asshole, the pretty brunette began lowering her body onto the plug, letting herself give into gravity. As her asshole starting to stretch again, she rubbed her breasts and clit, trying to give herself some pleasure to combat the pain. The burning in her ass increased the farther she went down, and as she got to the widest point, all of her weight was on her ass as her knees were almost at a 90 degree angle. Pinching her nipples and frantically rubbing her clit, she screamed again as her ass finally stretched around the base of the plug and popped over it, closing tightly around the indented part between the plug and the stand. Tears in her eyes, Allison just sat, breasts heaving prettily, looking up at the ceiling as she adjusted to the new proportions of her asshole. The plug was definitely wider than Todd.

Eventually, she began to move again, slowly rising to her feet. Then it was another few minutes adjusting to a standing position with the plug in her ass, before she could start walking back to her room. Each step jostled the position of the plug, making it jump and dance painfully inside her body. Gritting her teeth, she made it into her room before collapsing belly first onto her bed. Panting, she waited until the pain of the plug eased, and then opened her eyes to look over the other items on the bed. Groaning, she lifted herself up to look at the clock through tearful eyes.

Shit. 4 o'clock. If any of these other toys took nearly as long as this one she'd really be in trouble. Moving painfully, she pushed herself up and grabbed a bag randomly. It was the baggie with the two balls in it, the instructions told her to just push both of them inside her pussy, with the part of the string that had the ring hanging out so that they could be pulled out at need. Looking over the toy speculatively, she realized that they'd need to be fairly deep in her so that they didn't come out on their own while she was walking, since she wouldn't have any underwear on to hold them in. She pushed the first one in, and then the second, pushing them as far as she could with her fingers; the ring dangled obscenely between her legs.

Straightening, she started to walk, to make sure that the balls wouldn't fall out. Her first two steps caused her to gasp and quickly halt; when she moved, the balls moved inside of her, vibrating in her pussy. Turning back to the bed caused them to jingle merrily inside her as well... and it felt incredible, it almost distracted her completely from the pain in her ass. By the time she made it down to her car she'd be leaking juices down to her ankles with that kind of stimulation. Biting her lip, she tried to move as little as possible as she picked up the handcuffs, wondering if she would have to drive over to his house with them on. Thankfully, the instructions told her to wait until she got to his apartment, enter, then take off her jacket and put the handcuffs on with her hands behind her back. It gave her plenty of thoughts for what that evening was going to be like, but for now she didn't need to do anything with them. Picking up the gag, she saw that it had similar instructions except that she was to put it in before handcuffing herself. That just left the Y shaped chain.

Holding each tweezer around a hardened nipple, she tightened it as much as she could. The obvious threat on the instructions implied that if he didn't think that she'd tighten them enough, he'd tighten them as much as possible. It hurt horribly as the tender nub was squeezed tight by the rubber tips on the clamp. At least when she put the other clamp on it made a kind of balance of pain between her breasts, both of her nipples were red and swollen looking between the rubber tips; just touching them lightly with her fingertips sent jolts of pain shooting through her breasts, and she decided to hope that he'd deem them tight enough. Carefully she teased her clit so that it became it's own hardened little nub, and then she placed the clamp on that even more tender bud of nerves. Tears sprang to her eyes as pain flared in her pussy. Very slowly, taking care not to jostle the chain or either of her breasts, Allison went to get her coat.

The walk to the car was pure torture as the coat rubbed against her swollen nipples, her breasts bounced as she walked which made the chain jerk painfully on her clit and her nipples; the plug in her ass jostled her insides and the balls in her pussy added a confusing mix of intense pleasure to the cacophony of pain. Driving wasn't much fun either, most of her weight bored down on the plug, pressing it even more firmly into her tight ass, and every bump in the road increased her agony as her heavy breasts bounced and pulled on the chain. She couldn't even wear a seatbelt because it pressed her coat too tightly against her nipples. When nothing was touching her nipples, they were fine, but the lightest touch or brush against them caused sharp pain to radiate through her body.

By the time she was in front of Todd's door she was practically on the brink of an orgasm, despite all the pain and discomfort. The balls in her pussy had added just enough pleasure that her body was even leeching some pleasure out of the torture of her other delicate sex organs. In the hall of his apartment, she quickly shed the coat and took the gag and handcuffs from its pocket. Shoving the gag in her mouth, she fastened the elastic band around her head, making the little penis secure between her teeth. Hands cuffed behind her back, her insides quailed as she realized the way her breasts jutted out with the position of her arms.

Walking quickly, she entered his room to find him waiting, already naked. On his night stand there were several toys, one looked like a ping pong paddle, the other was obviously a whip, and the last looked like a black riding crop. Seeing the objects there, her eyes widened and she started making frantic sounds around the gag.

Frowning, Todd walked up to her, "I thought you understood that there would be no arguing with me on our dates."

Nodding frantically at his words, she continued to try to talk through the gag, trying to make him understand. Sighing, he popped the gag out of her mouth, and the words spilled forth quickly, as though she was afraid he wouldn't let her finish, "My parents are having a pool party tomorrow, I have to be there, and if I don't go swimming they're going to think that something's weird, and all I have are bikinis and they can't see any marks, they just can't, I don't have any way of explaining them..." Todd popped the gag back into her mouth as tears began leaking from her eyes. Thoughtfully, he examined the trembling and anxious girl in front of him, reveling a little in his power over her. He'd been cruising bdsm sights all week long, wanting to make sure that he didn't actually do any lasting damage to her. They had two more dates after all, but he wanted to impress on her quite firmly who was boss. Still, if her parents found out what she was doing every Friday night then his hold over her would definitely be gone.

With a shrug of his shoulders, he knew that what he wanted was still possible, but it was going to make it harder on her, "Well, we can do this without leaving marks where your parents will see them, but it's going to be a lot worse for you, is that what you want to agree to?"

Allison nodded her head frantically, anything rather than having to explain strange and painful marks to her upper class parents, especially in front of all their friends and co-workers. Todd smiled cruelly, "So be it." Roughly, he pushed her over to the bed, and with her hands behind her back Allison was forced to fall over it, her legs still on the ground. As her clamped nipples hit the fabric, she screamed behind the gag, pain flared through her nipples and breasts. Without much ado, Todd picked up the paddle and brought it down on the squirming girl's ass.

THWAK!

Her body jerked, making the chain pull both on her nipples and clit, which made her scream again. The paddle landed on her ass over and over again, making her struggle and squirm, which in turn fed more pain through her nipples and clit via the clamps. Dripping juices from her pussy came as the balls danced inside of her while she writhed on the bed. The worst slaps were the ones that he landed squarely on the base of the plug, they would give the plug a short sharp shove inward that made her the inside of her ass burn as much as her cheeks were starting to.

Over the sounds of the paddle hitting her ass and her muffled screams and cries of pain, Allison could hear Todd telling her over and over again what a bad girl she'd been, and that if she'd just been good last week and done as he'd told her to that this wouldn't be happening. It became like a mantra running through her head in his voice, she was bad, if she'd just listened and obeyed she wouldn't be in pain like this now. The beating went on until her ass was red and raw. When he finally stopped, Allison just slumped on the bed, panting and sobbing as her ass continued to burn; Todd could feel the heat emanating off the red flesh. Smiling, he pulled her up by her bound hands.

She continued to sniffle and weep as he undid the handcuffs and redid them in front of her body, bringing her to the other side of the bed, he lifted them up above her head and attached them to a rope that was hanging from a ring in the ceiling. Standing there, her body was stretched out with her arms and wrists high above her head, breasts thrust slightly forward. Todd smiled at her tear-streaked face, and then he went to get the rubber whip. It had 20 strands that were each 16" long; it could caress or it could bite depending on how hard he swung it and the angle it impacted at. If he was careful, he could whip her entire body with it and there would be no marks in the morning - except where he chose to leave them of course.

Allison was slumped, a good portion of her weight on her wrists as her legs felt wobbly. Her ass was still burning and she just hoped that whatever was coming next he'd leave her ass alone for a little bit. She was about to get her wish granted, but probably not in the way she wanted. The ends of the whip flicked along her breasts, a couple strands actually smacking into her nipples. Very quickly, Allison's body was dancing and squirming again, trying to get her breasts out of reach of the whip - which didn't actually help with avoiding pain since her movements caused the chain to stretch both her nipples and her clit as she danced. Todd had quite an amusing show to watch as her body jumped and heaved, heavy breasts bouncing delightfully, squeals emerging around her gag at the pain. He concentrated most of his hits on the undersides of her breasts and across the nipples, the areas guaranteed to be covered by a bikini.

Again, as he administered the punishment, his voice went on, this time telling her that she was being punished for not being accommodating enough towards her step-cousin, and for teasing guys that she wouldn't let touch her. If she had just accepted that her step-cousin was going to be part of the date, then her breasts wouldn't be taking the beating they were right now. Allison danced and sobbed, immensely sorry that she had questioned anything Todd wanted to do on a date, remembering how she'd teased her cousin (and numerous other guys, which did include Todd as well) she was sorry for that too. More than anything she was sorry for not having just accepted losing that poker game gracefully, because if she had been willing to follow through instead of still being a tease, then none of this would be happening. Finally, the whipping stopped, her nipples felt like ripe berries about to burst off her chest, they were so swollen and sore.

Her body hung completely slumped, all of her weight now on her wrists as her legs were too shaky to hold her up. Feeling some small pity, Todd decided not to pull on the chain connecting the clamps as he had planned to, instead he just stepped forward and released each one on her nipple. Still, Allison's head fell back and she panted behind the gag, tears continuing to fall freely as blood rushed back into the tortured nubs, and then he released her clit and more tears streamed. Gently, Todd tongue each of her nipples, making her shudder as even the soft wet touch brought pain. Smiling smugly, he released her wrists from the rope holding them above her head, although he kept them handcuffed together. Her sore and tired body fell against his chest, and he picked her up carefully, placing her on the bed.

Tying her handcuffs to the headboard, he repeated the position he'd put her in the first night he'd had her, with each leg tied to a bedpost on the headboard so that her body was nearly inside out. From this position her pussy was stretched wide open, it gave him the best access to her vulnerable pussy as well as her ass. Deciding to play a little, he began pulling the plug in her ass, bringing it to the point where it was almost going to pop over the widest edge before pushing it back in. Her eyes popped and she squirmed as much as possible in her position and gasped and moaned behind the gag; compared to everything else it wasn't quite painful, but it was definitely uncomfortable. After pumping the plug in her ass a few times, he decided he'd given her enough rest time and grabbed the whip again.