by Golden Angel
*****
By the time Allison left her Aunt Linda’s house, with Diana’s number in her cell phone and a promise that they would get together to hang out soon, she was feeling much better. Talking to other people about what was going on had been a relief. Having Diana’s enthusiastic support of the fulfillment of her fantasies, rather than horrified condemnation, made Allison feel less like she was deranged or completely perverted. And Chad’s desire to protect her from Todd’s blackmailing had been rather cute, and in turn made her feel protective of her experiences with Todd.
It had also made her face the fact that she was truly enjoying the games and hoops that Todd was putting her through. She didn’t want him to stop. In fact, she wasn’t sure that she ever wanted him to stop. Friday nights were becoming more about pleasing him and pushing her boundaries than they were about getting the tapes back. Destroying the video evidence had originally felt rather satisfying, now it just seemed like a silly tag end to her getting what she wanted.
But could there ever really be anything between them? Pulling into the gated driveway of her parent’s house – more like a mansion – with its exquisitely cared-for front lawn and sculptured gardens and comparing it to Todd’s apartment was disheartening in the way it drove home the differences between how they lived. At one point she would have looked down on his apartment, now it was starting to feel more comfortable and cozy than the foreboding structure of her own childhood home.
********
On Monday Allison thought about calling Todd, but what would she say to him? ‘Hey what’s up?’
She would feel like a complete idiot. No, no, she couldn’t do that.
By Tuesday she had actually gotten her phone out and sat staring at his name in her contact list for about ten minutes before she put it in her purse and went out the door to the sex store she’d found when she was getting her thigh highs. It didn’t take her long to find exactly what she wanted; a toy that she’d spotted the last time she’d been there but hadn’t been brave enough to get. Tucking the box into her purse after paying for it she hurried home and up to her room, feeling incredibly naughty.
She was so excited she immediately locked the door and stripped down. Just thinking about the things Todd had done with her, wondering what would come next, had her worked up. He had consumed her fantasy life and now all she thought about was what it would be like to truly be his. She’d come to realize that she liked the fight with him, liked resisting a little and having him leverage her into more hedonism. Although she wanted it, it was hard for her to admit that and she was only really able to let loose and enjoy herself once Todd exerted his dominance over her and had taken away her choices.
How odd that not having any choices made her feel so free.
Slipping her vibe into her pussy, set on low, she moaned a little as the teasing sensation of it flowed through her. Quickly she stripped off the packaging from her new toy, a 5” long and 1” in diameter anal probe that was heavily ribbed. Smearing lubricant over its ridged surface, she wondered out it would feel to have it moving in and out of her tight hole while her vibrator buzzed inside of her pussy. Would it be as incredible erotic as having two men inside of her? Probably not, but this would be the closest she could get at home.
Planting her feet on the mattress, she thrust her hips upwards, sliding her feet farther apart and bending her knees even more to get the perfect angle to push the head of the probe into her asshole as she pushed the vibrator deep into her pussy. Oh… fuck… the bumps in the probe passing through the tight ring of her anus was incredible… indescribable…
Although it was very hard to push both toys in and out of herself, she persevered. Wistfully Allison thought about Todd’s mastery over her body, his dark commanding eyes, the way his skin rasped against hers, his wide cock stretching her open. With a grunt of frustration for her inability to fuck herself satisfyingly in both holes, she pulled the length of the probe out of her ass and almost screamed as the sensation jolted her straight into a fantastic orgasm. Her pussy clenched and spasmed around the vibrator as she writhed in ecstasy, her ass clenching at its sudden emptiness and the rippling sensation the removal of the probe had caused.
Her climax was incredibly fulfilling physically, but she still found her thoughts turning to Todd despite the satisfaction she’d just given herself. For the first time in her life she felt insecure about a guy. Did he have any feelings for her? Or was this just an exciting fuck for him? Did he enjoy her as herself or just his power over her?
Or, like her, was it both?
******
On Wednesday a new email from Todd had finally arrived. Allison’s anticipation at seeing it in her inbox was almost disturbing.
Princess,
I am tired of having to reiterate that I am in charge on our dates and that you are getting nothing more than you asked for. You seemed to enjoy the spanking you got last week, I hope you stay in that frame of mind. This Friday I will have a friend drop off a package after your parents leave for work. In the package will be several items, there will be instructions for the use of each one. All of those instructions must be followed exactly. Other than what’s in the box, all you will wear is the coat from last week. Keep stretching out your ass. Be at my house at 5pm exactly. Do not be late.
Your Lord and Master
Allison bit her lip. Looking at his signature for this week’s email gave her the shivers and her nipples hardened. It was like he knew that she pushed him in order to get a response. The spanking he’d given her had been shockingly arousing, as much as being pushed up against the wall and held there had been.
Either Todd was very good at reading her body language and knowing exactly what she wanted, or their desires were very similar.
*******
Although Allison spent almost her entire Thursday afternoon hanging around the library, until she absolutely had to go home or be late for family dinner, there was no sign of Todd. She’d hoped that he might show up and give her an excuse to see him before Friday, but he was nowhere to be seen. In fact, he hadn’t been outside the gym when she’d walked by earlier either.
It was rather disheartening to think that he might be avoiding her. But, she reassured herself, she was probably over thinking things. Assuming that he wasn’t outside the gym because he was staying away from her seemed incredibly self-centered. The fundraiser that 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 that he had set was probably keeping him really busy. Especially since he wasn’t free on Friday nights.
And it was ridiculous to feel so disappointed about not seeing him.
Dinner with her parents that night dragged. They were obsessing over a backyard pool party that 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 that she didn’t feel comfortable swimming.
The upside was that, stuck in full planning mode, her parents were basically ignoring 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 was able to eat 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 or not they should cancel their usual string quartet and update to a DJ.
Allison wasn’t in the mood to focus on these discussions, although usually they were what she enjoyed most about the event. Normally she would sit with her parents and banger, 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.
And she didn’t want to be thinking about a stupid party that was never going to alter. Her focus was all on the next date and 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. Quickly she picked it up and carried it inside, heading straight for her room where she opened it. It was full of Ziploc bags, each one had something inside along with a piece of paper that had written instructions.
There were three things that 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 that was attached to a small plastic ring. When she picked the balls up they felt and sounded like there were more balls rolling inside of them. The pair of handcuffs made her insides twist in anticipation of being completely helpless for Todd.
Two items left. She picked up the small one since it was mostly on top of the other one anyway. It was some kind of gag, with a small phallus shaped pacifier looking thing. She made a face and 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 that she was exactly right. Looking at the black monster with a sinking feeling in her stomach, she decided that she’d best start trying to stretch her ass out a lot more than she had been if she was going to fit that thing into it. Thank goodness she’d gotten that 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. Carefully she fitted one finger into her ass. It slid in easily after all the practice she’d had in the past week of anal plundering. She slid a second finger in and moved them in and out of her ass in unison the slickness of her feelings made the sensation rather 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 of her tiny hole made her wince. At least it wasn’t a sharp pain, just that burning discomfort that 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, slowly beginning to enjoy the feeling of fullness, she started using her other hand to play with her clit, letting her face rest on the soft carpet.
Grimacing a little, she began trying to work her pinky in alongside the other 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 she was feeling a definite corresponding buzz in her pussy as she mimicked the anal sex act. She continued to work 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 lunch and then came back quickly, not wanting her muscles to close up too much after all that effort of getting them to 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 the lube over the entire bulb, making sure it was coated with the stuff. Then 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, it felt like before it started stretching her too wide and the burning discomfort became too much for her to force herself further.
Groaning with frustration and the uncomfortable ache in her over taxed 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 that she could work herself up to stretching over the largest portion of the bulb. Slowly she managed to get a little bit more inside of her, but it still felt like her asshole 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 the resistance, and screamed in pain as her burning hole felt like it was going to split open completely.
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 a little, 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 pain, she sighed and looked at her watch again. Dammit. 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 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 nudging into her entrance, the pretty brunette began lowering her body onto the plug, letting herself give 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 some 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 up 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 just needed to finish adjusting to the plug and then she’d have to 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 start walking back to her room. Every step jostled the position of the plug, making it jump and dance inside of her body, the aching burn not receding very 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 and 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 really be in trouble. Moving painfully, she pushed herself up and grabbed a bag randomly. It was the baggie with the two balls on a string in it. The instructions told her to just push both of them inside of her pussy, with the part of the string that had the ring hanging out so they could be removed easily. Looking over the toy speculatively, she realized that they’d need to be lodged fairly deep inside of 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, 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 inside of her, the sensation almost like a vibration but different. Turning back to the bed caused them to almost jingle against her clenching walls. It felt incredible. She was stuff full of toy, but the balls helped to dissipate some of the pain of the plug, and the plug actually 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. It gave her plenty of erotic images about 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 that 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 upwards, tightening the clamp as much as she could. The obvious threat in the instructions implied that if he didn’t think she’d tightened them enough, he’d tighten them as much as possible. The pinching pain was extremely 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. Both of her nipples were red and swollen looking between the rubber tips. Just touching them lightly with her finger tips sent jolts of pleasurable pain shooting through her and she decided to hope that he’d deem this tight enough.
