Chapter 7

Allison checkedher phone as she drove home from Todd's, sore and confused. She'd never expected to spend the night at his place—ever. Fortunately, she had a change of clothes in the trunk of her car, but what was she going to tell her parents? They had to be going out of their minds with worry. There were several missed calls and a text message from her mom. At a red light, she checked the text message and frowned.

Hey, sweetie. Chad told us about the late night. We're so glad you're finally getting along. We'll see you tomorrow.

She called Chad, who picked up in the phone with a voice roughened by sleep.

"Hello?"

"Chad? What did you tell my parents?" Allison's heart was racing, and her voice came out demanding and shrill. He groaned, sounding as if he wasn't awake yet. She tried to soften her voice while keeping the urgency. "Chad! I need to know what you told my parents."

"I… uh… I heard your phone going off last night when I was leaving, so I answered it. Ummm... told them I'd run into you when you were leaving study group, and you introduced me to a nice girl who's a friend of yours, and the three of us went out, and it got very late, and you didn't want to drive after drinking, so you spent the night here, and you were already asleep. Your mom was glad to hear you were getting your beauty sleep." He snorted.

"You told them I was spending the night with you?" Allison was completely aghast. Her parents were okay with that? Chad lived in the frat house. There was no way her parents would ever approve, no matter what they said to Chad. She was in so much trouble!

"No," he said, yawning. She wanted to reach through the phone and strangle him. "I'm house-sitting for Dad and Linda. I told them you were staying in a guest room."

Relief blew through Allison like a gust of wind. That's right, she remembered Aunt Linda saying they were taking a weekend away.

"So, who's the friend I introduced you to?" Allison asked dryly.

"You can come over if you want to meet her. Name's Diana."

"You met up with another girl last night?" She couldn't keep the surprise out of her voice.

Chad just laughed. "I was only with you and Todd until about eleven. After you passed out, I took a shower and hit the road. He didn't seem to want me to stick around after that."

"Oh." Questions flew through her mind, but she didn't know which one to ask.

"What's going on with you two, anyway?" Chad sounded more alert by the minute, and Allison wasn't sure she approved, considering he was asking questions she didn't know how to answer.

"Nothing," she said, keeping her voice short and her tone unwelcoming to further questions.

He laughed again, not at all put off by her iciness. It was an unusual reaction for him, and she blushed as she realized the reason. Being prudish with a guy who had his dick up your ass less than twelve hours ago wasn't exactly convincing.

"Who are you talking to?"

Allison heard the question as though it was from far away; obviously, the girl Chad had managed to pick up last night, even after being with Allison and Todd. To her surprise, she found she didn't care, even though part of her thought bed-hopping wasn't exactly… well… polite. She didn't care in a jealous or possessive sense, not like she would have with Todd. If it had been Todd who had picked up another girl… She suddenly found herself wondering what he did on nights other than Friday, not that it was really any of her business. They couldn't date, and when the summer came, her parents wouldn't accept she was in a study group every Friday.

"Allison."

For a moment, she thought Chad was speaking to her, then she realized he was answering the girl's—Diana—question.

"Oh, yes! Tell her to come over, I want to meet her. Here, give me the phone."

The demanding tone in her voice made Allison giggle. Chad was getting pushed around a bit, but as the soft crackling noise of a phone changing hands came over the receiver, she also found herself confused and a feeling a little trepidation. What did Diana know?

"Allison? Hi, I'm Diana."

"Um, hi… Nice to meet you." Although talking on the phone couldn't really be considered that, Allison's good manners were automatic.

"Why don't you come over, so I can really meet you? From what Chad tells me, you had a wild night last night! I'd love to hear more about it from a girl's point of view." Surprised at the honest interest in Diana's voice, Allison found herself tempted. Chad must have told Diana quite a bit, and she didn't sound judgmental at all. Allison had been dying to have a girlfriend she could talk to for weeks now, and after her last phone conversation with Chrissy, it was obvious her best friend wasn't going to be a viable candidate for her secret life. She was too afraid to tell Chrissy since she knew her parents. The lack of any kind of judgment was what really decided Allison. More than anything, she wanted acceptance… and a good gossip session.

"Sure, I'll be there in about ten minutes," Allison said as she turned her wheel, making an unexpected sharp right turn, heading toward Aunt Linda's.

"Great! Have you eaten yet?"

"No."

"Us either. Chad, go make breakfast. See you soon, Allison!"

Allison had to laugh at Diana's peremptory orders. She seemed like a girl who was used to getting her way. If nothing else, it would probably be a fun morning.

She'd better call her parents and keep them updated.

"Allison?"

"Hi, Mom, I'm so sorry I didn't call last night. I had a little too much to drink, and I just forgot before I fell asleep."

"That's fine, sweetheart. We're just happy you weren't driving after drinking. That's so adult of you." Funny how hearing her mother say that made her feel like she was still five years old. "If you're going to drink, being safe is the right thing to do. We're just glad Chad was there to get you back to Linda's."

The compliment grated on Allison's nerves for some reason. Maybe because she knew she was lying to her mother, but mostly, it was just another example of her mother not bothering to dig deeper into what was going on with her daughter. Did her parents really think she'd gone out with Chad? Had they never noticed the antagonism and rivalry between the two of them? Or was that just something to brush under the rug as soon as possible?

"Yeah, he was really great about it. I'm just lucky Aunt Linda has so many guest bedrooms."

"What about the girl you introduced him to? Is she a good girl? Will Linda approve?"

"Umm..." Allison swallowed as she thought quickly. "I don't really know her well, she's a part of the study group and very smart. I don't know if Chad's really interested in her. He just wanted to get to know her better."

"I see. Well, see what you can find out about her family, so we can decide whether to tell Linda. Hopefully, she won't need to intervene."

Allison's sudden blinding headache was worse than the residual soreness in her pussy and ass from last night. Her parents would be appalled if she even mentioned Todd or anyone like him. Why did they have to be so close-minded? Not she even knew if Todd was interested in her for anything other than sex, although he seemed to enjoy that thoroughly and liked having her in his bed, even if she wasn't doing anything other than sleeping. It had been rather nice to wake up with him wrapped rather around her.

Ack, she was getting distracted again.

"Sure, Mom. I'm going to have something to eat. I'll be home this afternoon."

"Okay, dear, we'll see you later," her mother replied airily.

Allison hung up the phone, wilted and dirty.

* * *

Diana turnedout to be a sweet-faced Asian girl, rather short at only five foot three with a slim body and small perky breasts. Her almond-shaped brown eyes were warm and friendly, and she had an easy smile. The long locks of her straight black hair fell almost to her waist and were obviously well cared for. Looks-wise, Allison's mother and Aunt Linda would surely approve. Dressed in an orange sundress that showed off the tan glow of her skin and white sandals strapped prettily around her slim ankles, Diana looked eminently appropriate. After some conversation, she found out Diana's father was a contract engineer for the government and traveled constantly, and her mother was a retired event planner who lived wherever her husband was at the moment, often leaving Diana at loose ends at home.

Due to her father's success, Diana joked she thought he was part of the CIA because he wasn't allowed to talk about what he actually did for his job. Her family's social and financial standing was more than high enough to please the Bradfords, which made Allison relax. She couldn't be accused of introducing Chad to someone "inappropriate," and she and Diana could become friends. Her parents would happily include Diana and her family in invitations. Part of her hated she had to consider that, but at least it was a positive.

It was almost too easy to talk to the girl. She was excitable and enthusiastic about everything and had grown up without a lot of supervision. The rebelliousness against the dictates of their place in society she wore on her sleeve, matched the desire to revolt in Allison's heart. She admired Diana, even though she knew it was obviously easier for the other girl. She had to play the good daughter when her parents were home, but now that she'd graduated from high school, they weren't often home anymore. A self-confessed "player," Diana announced—in front of Chad—while she had enjoyed him last night, she wasn't looking for a relationship. Predictably, this just made Chad even more entranced with her.

Diana was more fascinated by everything Allison had to say. The lonely brunette found herself pouring her heart out to Diana and Chad—her newfound frustration with her parents, the strictures on her life. She told them about her desire to do things she wanted without worrying about how it would reflect on her family—unlike some people, her family would be appalled and probably disown her if she leaked a sex tape, not go on a tv show with her—and finally, the confession she'd made to Todd and his subsequent blackmailing.

At that point, Chad got upset and had to be talked out of having a serious "conversation" with Todd. Fortunately, Diana was on Allison's side that it was her choice whether to do anything. She also understood the erotic appeal of being blackmailed, especially since it was something Allison had confessed to Todd.

"He's always pushing me and making me do things I secretly enjoy but would be too scared to do otherwise," Allison said. "Last night was…" She blushed and looked away from Chad. "It was incredibly hot to be with two men. Even if you might not have been who I would have chosen if he'd asked, that just makes it even more exciting in a lot of ways."

Chad looked unconvinced but willing to take her word for it. Diana looked frankly envious about the two men part.

"If he ever makes you do anything you really don't want to do, you'll tell me, right?" he asked. Chad so concerned with her well-being actually touched, Allison even if it wasn't necessary.

"Yes, of course," she reassured him, bemused. "But I don't think he will. It's… it's a game we're playing. If I told him no and stuck to it, I think he'd hand over the tapes immediately, no problem. But I always cave because ultimately, that's what I really want." She blushed, knowing how true her words were and a little ashamed at admitting them, but it also felt really good to verbalize it. Explaining it to Diana and Chad was making it easier for her to face it herself.

"But he's blackmailing you, so how do you know he'd give in?" Chad asked, rolling his eyes at her naivety.

Allison blushed again. "Well, he asked me about the things I wanted him to make me do." Once she admitted that, nothing would satisfy Diana until she told them about Todd finding her in the library and fingering her while he asked about her fantasies.

Although Chad had noticed Todd hadn't seemed particularly eager to share Allison, he didn't tell her that. After all, he might not have been reading his frat brother's emotions correctly, and just in case, he didn't want Allison to get hurt. It didn't even occur to him how sleeping with her had so obviously changed their relationship. His fantasy fulfilled, he found himself protective of her.

* * *

By the timeAllison left her Aunt Linda's house, with Diana's number in her cell phone and a promise 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. Diana's enthusiastic support for the fulfillment of her fantasies, rather than horrified condemnation, made Allison feel less like she was deranged or perverted. 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 she was truly enjoying the games and hoops Todd was putting her through. She didn't want him to stop. In fact, she wasn't sure 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 was satisfying, but now it seemed like a silly tag end to her getting what she wanted.

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, driving 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? ‘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 back in her purse and went out the door to the sex store she'd found when she was bought her thigh-highs.

It didn't take long to find exactly what she wanted, a toy 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 consumed her fantasy life, and all she thought about was what it would be like to truly be his. She'd come to realize 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. She was only able to really let loose and enjoy herself once Todd exerted his dominance 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 as the teasing sensation flowed through her. She stripped off the packaging from her new toy, a five-inches long and one-inch in diameter anal probe that was heavily ribbed. Smearing lubricant over its ridged surface, she wondered how it would feel to have it moving in and out of her tight hole while her vibrator buzzed inside her pussy. Would it be as 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 upward, 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 on the probe, passing through the tight ring of her anus was incredible… indescribable…

Although it was hard to push both toys in and out of, she persevered. 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 satisfyingly fuck herself in both holes, she pulled the length of the probe out of her ass and almost screamed as the sensation jolted her straight into 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 fulfilling physically, but she still found her thoughts turning to Todd. 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? Did he enjoy her or his power over her… or both?

* * *

On Wednesday,a new email from Todd finally arrived. Allison's anticipation seeing it in her inbox was almost disturbing.

Princess,

I am tired of having to reiterate that I am in charge of our dates, and 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, a friend will drop off a package after your parents leave for work. Several items will be in the package, with instructions for the use of each one. The 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. 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 as if he knew she pushed him 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.

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 almosther entire Thursday afternoon hanging around the library until she had to go home or be late for a family dinner, there was no sign of Todd. She'd hoped 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 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 asshe 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.

The walk to the car was pure torture—the coat rubbed against her swollen nipples, her breasts bounced as she walked, making the chain jerk and pull on her clit and 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 sensations fighting for dominance inside of her. Driving was worse. Most of her weight bore down on the plug, pressing it 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. The seatbelt pressed against her coat, making her nipples and clit throb as the chain tugged at them.

By the time she was in front of Todd's door, she was on the brink of an orgasm. The balls in her pussy had added just enough ecstasy, her body was leeching confused pleased from the torture of her other delicate sex organs, and her thighs were slick with her juices. In the hall of his apartment, she quickly shed the coat and took the gag and handcuffs from the pocket. Shoving the gag in her mouth, she fastened the band around her head, securing the little fake penis between her teeth. Hands cuffed behind her back, her insides quailed as she realized how her breasts jutted out in front of her due to the positioning of her arms, offering them up for whatever Todd had in mind for tonight.

Following his final instruction, she walked to his room, feeling more vulnerable and hornier with every step. He was waiting, naked and erect, his face blank. Only his eyes showed his eagerness as they swept over her body, drinking in the sight of her submission. On the nightstand beside him were several… implements. One looked like a ping-pong paddle, another a riding crop, and the last was obviously a whip. Seeing them, her eyes widened, and she started making frantic sounds behind the gag, shaking her head and pleading with her eyes.

Frowning, Todd stalked toward her, the pleasure in his eyes fading quickly.

"I thought you understood there would be no more arguing with me." He seemed more confused than angry as if he was pondering whether he'd gone too far.

Nodding frantically at his words, she continued to try to talk through the gag, jiggling with frustration, which made her moan as the clamps tugged again. Frowning, he reached behind her head to undo the gag, popping it out of her mouth, and the words spilled forth as she hastened to make herself understood.

"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 wrong, and all I have are bikinis, and they can't see marks on me, they just can't, I don't have any way of explaining them?—"

Todd popped the gag back in her mouth. She made a mewling noise, eyes pleading with him to understand. Thoughtfully, he examined the trembling and anxious girl in front of him, feeling relieved now that he understood she didn't want to end their evening. He'd been cruising BDSM websites all week, practicing with the three implements he'd chosen, wanting to make sure he didn't do anything to harm her. What he wanted was still possible, but it was going to be harder on her than he'd intended.

"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 that way. Is that what you want to agree to?" The tone in his voice was sincere, offering her an out if she wanted it, confirming her suspicions that if she ever truly wanted this blackmail to stop, all she had to do was state that and stick to it.

That wasn't what she wanted.

Allison nodded, eyes shining as she looked up at him. She needed to cum so badly. She needed this.

Todd smiled cruelly. "So be it."

Roughly he pushed her over to the bed. With her hands cuffed behind her back, Allison fell face forward, her feet still on the ground. As her clamped nipples hit the fabric, she screamed behind the gag, pain flaring through her breasts and sending jagged heat to her roiling core. Without much ado, Todd picked up the paddle and brought it down on the center of her squirming ass.

THWACK!

Her body jerked, making the chain pull on her nipples and clit, so she was burning on the front and the back. She yelped into the gag. The paddle hit again, then again in the center over her butt crack, where her bikini bottoms would be sure to cover. Despite her resolve to keep still and spare her breasts and clit as much as possible, she began to dance as the steady blows to her reddening bottom continued. Juices dripped from her pussy as the balls danced inside her as she writhed on the bed, unable to escape the raining blows. The worst slaps were the ones he landed squarely on the base of the plug, giving the plug a short sharp shove inward that made the inside of her ass burn, just as her cheeks were starting to.

Over the sound of the paddle hitting her ass and her muffled screams and cries of pain, Allison could hear Todd telling her over and over what a bad girl she'd been, and if she'd just been good last week and done as he'd told her, this wouldn't be happening. It became a mantra running through her head, in his deep voice. The spanking went on until that spot on her ass was dark cherry red, and she was sobbing, her hands twitching in the cuffs.

When he finally stopped, she slumped on the bed, wishing with all her heart she'd been more accepting of his plans last week, which had turned out to be entirely enjoyable, and she and Chad were getting along better than ever. By the end, nothing Todd had done to her hadn't been enjoyable. She should have trusted him.

Stepping up behind her, Todd put his hand over the dark red center of her bottom. It looked like a target, imprinted onto her creamy flesh, and he could feel the heat emanating from it. It would have been easier on her if he'd been able to spread the spanking over her entire butt, but he hadn't given her as many spanks as he would have to make it tolerable.

She continued to sniffle and weep, although she didn't protest as he undid the handcuffs and reattached them with her wrists in front of her body. Bringing her to the other side of the bed, he lifted her hands above her head and attached them to a rope hanging from a ring in the ceiling, he'd put there especially for her.

Her body was stretched out with her arms and wrists high above her head and breasts thrust forward. Todd smiled at her tear-streaked face, then got the rubber whip. It had twenty strands, each a foot long, and could caress or bite, depending on how hard he swung it and the angle of impact. He'd tested it on himself.

If he was careful, he could whip her entire body, and there would be no marks in the morning.

Allison was slightly slumped, a good portion of her weight on her wrists as she wobbled. Her ass was still burning, and she just hoped whatever was coming next, he'd leave her ass alone for a while.

She was about to get her wish. The ends of the whip flicked along her breasts, a couple strands smacking her tortured nipples. Squealing, her head lifted, and she stared at Todd as he smiled sincerely at her, then flicked his wrist again.

Very quickly, Allison's body was dancing and squirming, trying to get her breasts out of reach of the whip—which didn't actually help to avoid pain since her movements caused the chain to stretch her nipples and clit as she twisted and turned. Todd had quite an amusing show as she danced for him, heavy breasts bouncing delightfully, squeals emerging around the gag. He concentrated most of his hits on the undersides of her breasts and across her swollen nipples, areas guaranteed to be covered by a bikini.

Tears leaked down her face again as the pain in her nipples became almost unbearable, making them feel as if they were going to pop right off of her chest. Todd continued his diatribe about how she needed to accept his dominance on Friday nights and stop arguing with him for the sake of arguing. Finally, the whipping stopped, and Allison slumped, all of her weight on her wrists.

Todd moved to support her, not wanting her to damage her wrists. Holding her firmly around the waist with one arm, he took pity on her and decided not to pull on the chain connecting the clamps as he'd planned. Instead, he reached down and released her nipples from their torment. Allison's head fell back, and she moaned unhappily as he rubbed the tender buds. They tingled and flared as blood circulation in them again. She cried out when he released her clit and rubbed it as well, caught somewhere between extreme pleasure and exquisite pain.

Todd leaned down to suck each of her nipples gently, his tongue swirling around them. He suckled each of them, soothing the sore flesh with his mouth before dropping to his knees and repeating the process with her clit. It wasn't long before Allison was thrusting her hips, enjoying the lingering ache the clamps had left and the sensual heat now rising.

Smiling smugly, he ignored her groan of disappointment when he stood and released her wrists from the rope holding them above her head, although he kept them handcuffed together. Her sore and tired body falling against his chest, he picked her up and laid her down on the bed.

Tying her handcuffs to the headboard, he repeated the position he'd put her in the first night, with each leg tied to a bedpost on the headboard, so her body was nearly inside out. From this position, her pussy was stretched wide open and completely accessible, as was her ass.

Wanting to play a little, wondering how the effect of such a large toy had on her, he began pulling on the base of the plug, bringing it to the point where it almost popped over the widest edge before pushing it back in. Allison thrashed as much as possible in her position, gasping and moaning protests behind the gag. Compared to everything else, it wasn't as painful, but it was definitely uncomfortable. After pumping the plug a few times, he decided he'd given her enough rest and grabbed the whip again.

Raising his arm, he brought it down without too much force, grinning as her eyes widened, her back arching as the ends slapped against the inner and outer lips of her pussy. She whined as he began to repeat the slaps, bringing the whip down with a little more force each time.

"See? Nothing where your parents will be able to see," he said, grinning.

Her face reflected her resignation as she realized she'd put herself in this position. The rising force of the whip made her moan, especially when the rubber snapped against her tender clit, which felt like it was currently twice its normal size thanks to the clamp and Todd's mouth.

Once the noise level behind her gag started growing, Todd stopped, then lowered his lips to her pussy, licking gently along the sides and pushing his finger in her hole to rock the balls inside of her. Very quickly, the pain was overridden by the pleasure. Allison began a different kind of moaning, trying to move her hips with the strokes of his tongue. As soon as she did, Todd pulled back, a wicked gleam in his eyes.

Allison's heart sank as he began whipping her splayed pussy again, which hurt twice as much as when the whip encountered her aroused flesh. She squirmed and whined, trying to get back some of the pleasure his tongue had brought her as the stinging bites of the rubber assailed her. Twice more, Todd stopped and licked her, each time bringing her to the brink of orgasm before resuming the whipping of her vulnerable pussy.

It took less and less time for her to cry from the bite of the whip and less and less time for her to enjoy his tongue. Her pussy was burning with need even as he whipped it and quivering with pain even as he licked it. Finally, he brought her to the very brink of orgasm with his tongue and grabbing the riding crop, he slammed the flat of it onto her clit several times in quick succession. She screamed her climax as the pain flared through her clit, sending her body on an intense wave of mingled ecstasy and torment that was almost too much to bear. He continued to crop her sensitive folds, much more lightly, as she rocked with the waves of pleasure until her orgasm slowed, and she was boneless in her restraints.

Her eyes opened, tears clinging to her long lashes as he spoke.

"Did you enjoy that, Princess?"

Allison nodded, her body drained and satisfied despite the aches and discomfort. She had enjoyed it far more than she'd have thought possible. Being tied up flat out did it for her. Inflicting sexual torture just made her orgasm even better. There was something wrong with her, but right now, she didn't care.

Todd pulled the balls from her sopping pussy and untied her legs. He wanted to feel her body moving underneath him, but he left her arms tied to the bedpost. They both enjoyed her helpless position when she couldn't use her arms. At the last moment, he undid her gag, so if she really needed him to stop, she could tell him.

Spreading her legs with his knees, he pushed his thick dick into her swollen, abused flesh, which was made all the more painful as her pussy was tighter than usual because of the plug in her ass. As she yelped and whimpered, he could feel her slender body wriggling beneath his. He worked himself in, burying himself in her wetness. The press of his hard body against her abused parts made her feel raw, the wiry hairs on his chest abrasive against her nipples and breasts.

Slowly he began to pump in and out, letting each agonizing inch of his dick pull and push at her sore and bruised pussy flesh. As he moved within her, he lowered his mouth to her swollen nipple, gently rolling it with his tongue. Despite the jagged peaks of pain his mouth on her nipple caused, it also ignited little fires of pleasure that trickled through her. He began moving more forcefully as the slight sounds she made indicated she was starting to enjoy herself again. He transferred his mouth to the other nipple, giving it the same tender, soothing treatment. Her sore body began to respond and move beneath his.

He worked her, moving gently to allow her rising pleasure to override the ordeal he'd put her through. Her overworked clit began to respond positively to his movements, and even the plug in her ass added to the sensations that began coursing through her. The gentle and soothing lovemaking was a calming balm, making her feel like the princess he called her. For the first time, he was treating her as she had always imagined her lover would—other than the handcuffs and the plug, of course. She felt more vulnerable than ever, yet she trusted him not to hurt her anymore. Now that she had taken her punishment, she wouldn't have to pay it ever again.

Her body responded to him, and a feeling of triumph rushed through him that this girl, who probably would have never dated him, was now in his arms and willingly moving in rhythm with him. Her eyes were closed, and her face was full of her pleasure. Moving more strongly, he skillfully built her climax, allowing her to override every part of her that felt pain as the pleasure in her pussy built higher and higher. Finally, as her body arched beneath him and she cried out her pleasure behind the gag, he swept her legs over his shoulders, pumping his dick in and out of her as she rode out the climax, then pulled the plug from her ass. Despite the slight pain from having her ass stretched out over the monster again, the sensation only added to the climax as another part of her body was finally able to relax. Allison drifted down from her orgasm with Todd still pumping steadily into her pussy.

He pulled his dick from her pussy and pushed it into her widely stretched ass. It wasn't as tight since the plug had been in it all evening, but neither did it cause her any pain. Moving quickly, he pummeled her ass hard, finally letting himself go. Allison was lost in her haze of pleasure, barely noticing her legs were spread over her shoulders or that Todd was burying himself balls deep in her ass. It just felt pleasantly sinful, a slick sliding fullness, even though some of the discomfort was returning to her pussy and her breasts.

Todd groaned as he fucked her ass. The time spent tormenting her, then holding onto his control while in her pussy had taken its toll, and his balls were bursting with need. Thrusting hard one last time, he buried himself deep in her ass as jet after jet of his boiling cum shot into the darkness. It felt like he came forever, the biggest load of his life planted deep in her ass. His hips jerked as the sensation slowed, and he relaxed on top of her sore body, completely spent.

Uncuffing her, he kept his dick buried in her ass, liking it there, and she hadn't. When her arms were released, to his surprise, they settled around his shoulders. He realized it was probably the most comfortable position for her as he was still lying on top of her.

"Good girl," he whispered into her ear and felt her sigh happily beneath him. Lowering his lips to hers, he gave her a gentle kiss, which she returned. He could feel the exhaustion in her muscles. Groaning, he let his dick fall from her ass with a pop.

Allison's lips pursed, almost in disappointment, but it really wouldn't do to spend another night here. Moving gingerly, she gathered herself up off the bed and got her coat. He smiled as he watched. She was walking funny again.

Decently covered, although it obviously hurt where her coat brushed against her chest, she walked to the door and turned to look at him. For a moment, it looked as if she was going to say something, then she just nodded in a kind of farewell and left.

When Allison got home, she didn't even want to think about masturbating, her body was far too sore. She felt dreamy. Even though it was only ten p.m., it felt as if she'd been at his apartment forever. She fell into bed and went straight to sleep, still wrapped in her coat. As she slept, Todd's cum slowly leaked from her ass.