Page 21 of Calling Her Bluff

It was disheartening to think he might be avoiding her, but she reassured herself, she was probably overthinking things. Assuming he wasn’t outside the gym because he was staying away from her was incredibly self-centered. The fundraiser he was working on was coming up in a few weeks, right before the end of the school year. So, promoting it and trying to meet the new goals he had set was probably keeping him really busy, especially since he wasn’t free on Friday nights.

It was ridiculous to feel so disappointed not seeing him.

Dinner with her parents that night dragged. They were obsessing over a backyard pool party her dad was having for his clients on Saturday afternoon. Allison hated the yearly event, although she was required to attend and be a good hostess. Her father’s lecherous old clients always enjoyed a good gawk at her in a bikini. It was the only day of the year she didn’t feel comfortable swimming.

The upside was, stuck in full planning mode, her parents basically ignored her. There weren’t a lot of details to be planned since the same basic format for the party was followed every year, but a few days before the party, her parents would always go into a frenzy as if something major had changed last minute. Allison ate as quickly as possible, occasionally adding a meaningless comment or opinion when her parents would ask about the appetizers they were planning on serving, the arrangement of the dessert table, or whether they should cancel their usual string quartet and update to a DJ.

Allison wasn’t in the mood to focus, although usually, they were what she enjoyed most about the event. Normally, she would sit with her parents and banter, arguing back and forth about the pros and cons of changing things before everyone agreed it was best to keep things as they were.

She didn’t want things as they were anymore. She wanted change.

She didn’t want to be thinking about a stupid party that was never going to change. Her focus was on her upcoming date with her Lord and Master.

* * *

As soon as she woke up, a couple hours after her parents had left, Allison peeked out the front door. On the front steps was a brown box with her name on it. Fortunately, none of the staff had seen it. Picking it up, she carried it inside, heading straight for her room. It was full of Ziploc bags, each one with something inside, along with a piece of paper with written instructions.

Three things looked like tweezers with a thin band around their bases, connected by a chain shaped like a “Y.” Two balls, connected by a string, and one ball had another string hanging from it attached to a small plastic ring. When she picked up the balls, they felt and sounded like there were more balls rolling inside them. The pair of handcuffs made her insides twist in anticipation of being completely helpless to Todd.

Two items left. The first was some kind of gag with a small phallus-shaped pacifier thing. She made a face, then pulled out the last item, and gasped in horror. Easily the largest thing in the box, the plug’s thickest point looked even wider than Todd’s cock, and it was very heavy. The black color made it look even more frightening.

Pulling out the instructions, hoping she was wrong, her heart sank as she read and found she was right. Looking at the black monster with a sinking feeling in her stomach, she decided she’d best stretch her ass out a lot more than she had been if she was going to fit that thing into it. Thank goodness, she had lube and had been masturbating with a probe in her ass, although it wasn’t even half as thick as the plug.

Greasing her fingers, she got on her hands and knees on the bathroom carpet, the blue shag keeping her from the coolness of the tiles. She fit one finger into her ass, sliding it in easily after the practice she had the past week of anal plundering. She slid a second finger in and moved them in and out of her ass, the slickness of her fingers making the sensation pleasant. Being aroused couldn’t hurt, she thought. After a few minutes of enjoying the naughty feeling of fingering her own ass, she pulled them out and began to push in three.

The increased width into her tiny hole made her wince. It wasn’t a sharp pain, just the burning discomfort she was starting to associate with anal endeavors. The sensation eased as her slick hole adjusted. Panting, she worked her three fingers in and out, trying to prepare herself for what came next. Giving herself plenty of time to adjust to three fingers, beginning to enjoy the fullness, she used her other hand to play with her clit, letting her face rest on the soft carpet.

Grimacing, she tried to work her pinky in alongside the other three fingers. It was starting to hurt again, so she squeezed her clit to help take her mind off the pain. With four fingers buried in her ass, there was a definite corresponding buzz in her pussy as she mimicked the anal sex act. She worked her clit until she had a small climax, her body spasming tightly.

Picking herself up from the bathroom floor, she glanced at her watch, one o’clock. She ran downstairs to eat a quick lunch, then came back, not wanting her muscles to close up too much after all the effort of getting them to open. Grabbing the big black plug, she brought it into the bathroom and eyeing dubiously. It looked an awful lot bigger than her fingers—no way to know without trying.

Liberally spreading the lube over the entire bulb, she made sure it was coated. Getting into her position on the floor again, she used her fingers to re-grease her hole—which suddenly felt even smaller than usual. After her entrance was coated in lube and readjusted to the width of her fingers, she took the plug and began easing it in. She managed to get a good portion in before it started stretching her too wide, and the burning discomfort became too much. Groaning with frustration and the uncomfortable ache in her overtaxed bottom, she had to let it slide out, so her body could relax.

After giving herself a minute, she determinedly began to work the plug back and forth, trying to stretch herself out a little more with every entrance of the toy into her body, hoping she could work herself up to stretching over the largest portion of the bulb. She managed to get a little more inside, but it still felt like her asshole was never going to gape wide enough to get the whole thing in. A little desperate, she tried to just shove it in, despite the resistance and screamed in pain as her burning hole felt like it was going to split open. Whimpering, she let the plug slide out again, and a few tears fell onto the soft carpet beneath her face as she moaned and recovered.

Sniffling, she picked herself up off of the carpet. Maybe a new position would help. She inspected the plug. From the way the lube looked on it, she’d almost gotten herself over the widest part. Just a little bit more and she would have done it. Wincing at the memory of the pain, she sighed and looked at her watch again—damnit, three o’clock. In an hour and a half, she had to head to Todd’s, 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 the other items. 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 the tip of the plug was nudging into her entrance, the pretty brunette began lowering her body onto the plug, giving in to the earth’s pull on her body. As her hole started to stretch again, she rubbed her breasts and clit, trying to give herself pleasure to combat the growing discomfort and 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 at almost 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 bulb and popped over it, closing tightly around the intended part between the bulb and the base. Tears in her eyes, Allison stayed perfectly still, breasts heaving prettily, looking at the ceiling as she adjusted to the new proportions of her poor, abused back door.

The plug was definitely wider than Todd—damn him. She wished she had time to play with herself and bring herself to another orgasm, but right now, she needed to finish adjusting to the plug, then finish the rest of his instructions.

Thinking about what worse he could have in store for her if she was late, Allison began to move again, slowly rising to her feet. She spent another few minutes adjusting to a standing position before she could walk back to her bedroom. Every step jostled the position of the plug, making it jump and dance inside of her body, the aching burn not receding much. Gritting her teeth, she made it into her room before collapsing belly first onto her bed. Panting, she waited until the discomfort eased again, then opened her eyes to look over the other items on the bed. The debasement was turning her on even more.

Groaning, wondering if perhaps she did have time to play with herself, she lifted herself up to look at the clock.

Damn, a quarter to four.

If any of these other toys took nearly as long as this one, she’d be in trouble. Moving painfully, she pushed herself up and grabbed a bag randomly, the baggie with the two balls on a string. The instructions told her to push both of them inside of her pussy, with the part of the string with the ring hanging out, so they could be removed easily. Looking over the toy speculatively, she realized they’d need to be lodged fairly deep, so 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, followed by the second, shoving them as deeply as she could with her fingers, the ring dangling obscenely between her legs.

Straightening, she decided to walk a little to make sure the balls wouldn’t fall out. Her first two steps caused her to gasp and quickly halt. When she moved, the balls moved, the sensation like a vibration but different. Turning back to the bed caused them to jingle against her clenching walls. It felt incredible. She was stuffed full of toys, but the balls helped to dissipate some of the pain of the plug, and the plug was probably helping to hold the balls in by making her tunnel tighter. Of course, it also made her want to cum even more.

By the time she made it down to her car, she’d be leaking juices 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 cuffs on with her hands behind her back. She had plenty of erotic images of what the evening was going to be like, and as delightfully distracting as that was, she really needed to focus.

Picking up the gag, she saw that it had similar instructions, except she was to put it in her mouth before handcuffing herself. That just left the Y shaped chain.

Holding each tweezer around a hardened nipple, she slid the band at the base upward, tightening the clamp as much as she could. The obvious threat in the instructions implied if he didn’t think she’d tightened them enough, he’d tighten them as much as possible. The pinching pain was erotic, although the unrelenting pressure was much more intense than the kind of stimulation she was used to. Adding the second clamp balanced the pain between her breasts, arousing her even more. Her nipples were red and swollen between the rubber tips. Just touching them lightly with her fingertips sent jolts of pleasurable pain shooting through her, and she decided to hope he’d deem this tight enough.

Carefully, she teased her clit, so it became even harder and more prominent than it already was before placing the last clamp on that even more tender bundle of nerves. Tears sprang into her eyes as the pain flared, followed by a rush of wet heat. Very slowly, taking care to jostle the various toys as little as possible, Allison went to her closet to get her coat.

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