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The Perils of Being Too Trusting

By: koala011860091



"Fuck! If this traffic goes any slower, I'll be going backwards!" Heather swore at no one in particular. She had just finished up her afternoon babysitting job, and the 45 minute drive home seemed to be taking forever. While stop and go traffic was making her antsy, it was just as likely that her persistent rubbing of her clit through her panties was the real culprit. While it felt fantastic, it was also driving her crazy; plus it was totally reckless. No one could have been more surprised than she was that she had her hand up under her skirt, rubbing her pussy through her damp panties, but that was just the beginning of how bizarre things were getting. In general, she had always been pretty tame and conservative when it came to sex, but it seemed her universe had exploded over the last few months. 

It had started about six months after she graduated from college, after she had moved in with a couple college friends and started out into the real world. While she was making ends meet waiting tables and babysitting, she couldn't find anything in her chosen field, and it left her unfulfilled. It also frequently left her feeling incredibly horny. Her most recent fuck buddy had moved away after the end of school, and she hadn't gotten laid since graduation. She could no longer count how many times she had masturbated to "50 Shades of Gray" and eventually the excitement was completely gone from that story. She moved on to looking online for other stories that could get her worked up the same way, and had eventually found sites on the web with stories that made E.L. James' stories seem tamer than Mother Goose. There was one author in particular who seemed to hit on all her favorite aspects of a dirty story. Female submission, the heroine put in difficult and humiliating situation, and forced to behave like a... well like a slut. The stories gave her butterflies, and made her pussy damp every time she thought about them.

She spent months reading all of the stories, but once she had read them all over and over again she had that empty feeling again, and she found nothing new to get her going the same way. On a whim, she decided to contact the author to see if he was writing anymore. She made up a new email address to keep her identity secret, but with an eye towards piquing his interest. So nawtyteezegirl89 contacted SpareRod2003 to let him know how much she enjoyed his stories, and wondering if more were in the works. He responded about a week later, asking some specific questions about what she liked best, what she wanted more of, and also what she didn't like so much. She wasn't very experienced in this area, but she answered honestly, and was glad when he wrote her back, engaging her more in the stories. After about a month of emailing back and forth they started using instant messaging to chat rather than wait for emails. The immediacy of chat had sucked her in, and she had shared more of her fantasies with him. Soon they were making up stories together on chat, stories about girls being coerced into humiliating situations, being spanked for being naughty, being blackmailed to act like a slut. Actually, he made up most of the stories, she just gave little plot elements along the way. It wasn't as much that she couldn't come up with ideas, as that it was hard to do while she was masturbating.

After a month or so, he started asking about what she was doing while they were making up these stories, and she admitted she was playing with herself. He pressed her for details, and before she knew it, he was guiding the way she masturbated. As she got closer to orgasm, he kept moderating her rubbing so she stayed at the edge without going over, and he urged her to divulge her fantasies to him. She blurted out something about being tied up naked in public, and he told her a story about her being tied up like that and discovered by a crowd that groped, spanked, and humiliated her. He kept the story going until she had an earthshattering orgasm.

The experience had rocked Heather's world way more that she could have imagined. She had never masturbated in front of anyone, and even though he couldn't see her, and didn't even know if she was really doing it, it still felt intensely personal. On top of that, the orgasm was monumental.  While she was a little bit embarrassed to have been sexting like some adolescent, she had to admit she couldn't wait to do it again.

It was only a matter of time before they reached the point where she and SpareRod would chat almost every day, and often more than once a day. Sometimes while she was on break from her waitressing job, sometimes after the kids had gone down when she was babysitting, and often from home. They would frequently fantasize about a fictional character they had made up named Elaine, and the travails they put her through. Other times he would ask Heather what she was doing, and he would command her do an escalating set of kinky tasks. Many she would actually do (strip naked in her bedroom, masturbate in her car, masturbate with a finger up her asshole), a few she fibbed and said she did when she actually didn't (get naked in her living room with the blinds open, step naked into her backyard), and a few that she had to say she just couldn't do (take her underwear off under her clothes in a public place, get totally naked in her car). Even though those things turned her on like crazy, she just knew there was no way she could ever do them in real life.

The one thing she never lied about was her orgasms. It seemed funny when she thought about it, since she was lying about a number of things (where she lived, what her name was, where she might get undressed) but the orgasms were too good, too meaningful to sully them. So she would always drop hints early in the conversation if she was looking to cum, and he had very quickly picked up that she was only going to cum when she was in the mood. She never even had to tell him, he figured it out on his own, and he never questioned it or badgered her. It was one of the things she liked about him, that he never pried too deep about her, and beyond an open offer that she could send him a picture of herself if she wanted, he never pestered her for anything. So it caught her a little off guard when about a week ago he had asked if she would be willing to do a video chat with him. Again, he made it clear there was no pressure, just that he thought it would be fun. Even more surprising to her was when she had answered "maybe" instead of "no." Part of it was she didn't want to disappoint him. While it wasn't like he was her boyfriend or anything, she had grown incredibly fond of him, and felt very close to him. It was crazy – she didn't know his name, he was way older than her, and he lived out in California. But chatting with him had kind of taken over her life, and she felt like she really connected with him. She trusted him.

Of course the other reason she hadn't ruled out a video chat was that the idea deeply excited her. What if he talked her into getting naked? Could she really do it? Could she show off like that? Maybe even masturbate with him watching? What else would he want her to do? She imagined watching his eyes on the screen as she followed his commands, stripping and playing with herself. The whole idea seemed deliciously wicked, and she found herself imagining it more and more as she masturbated.

But the idea of doing it in real life also terrified her horribly. Every time she chatted online with him her stomach did flip flops. Soon their chats ended up as a role play of what a video chat might be like. She loved thinking about how it would feel if she was really doing it, and not just a fantasy. After a while, he bumped up the pressure by having her spend most of the chats right on the edge of orgasm, but then stopping and forbidding her from cumming. To make it worse, he told her that she shouldn't cum between chats as well. While there was nothing to keep her from cheating, she was intrigued by the concept of how it would feel bringing herself to the edge of cumming but holding back several times over the course of days.

The answer was that it would feel like she was going totally fucking insane. It was now over 9 days since she had had an orgasm, even though she had been masturbating right to the edge while chatting with SpareRod at least once every day, and often two or three times.  It seemed like her pussy was tingling all the time.  She was almost always wet, and had to change her panties frequently, especially when he made her rub her clit through them. After about six days, she had started playing with her pussy almost spontaneously, like she was now in her car. She hadn't started rubbing herself in public like a total pervert, thank God. At least she hadn't yet, although doing it under her skirt behind the tinted windows of her car was coming very close. 

As she had become antsier and more distracted by her buzzing clit, the idea of the video chat seemed more and more reasonable. It was actually kind of scary that just a week and a half of no orgasms had her seriously considering doing something that she normally wouldn't. God knew where this kind of thing could lead in the future. 

Finally, she had asked him if they could really do it. It was the scariest thing Heather had ever done. Her stomach was turning flips while she was trying to work up the courage to ask, and then as soon as she had, she was terrified. How could she have done that? Would she be able to follow through? To her surprise he didn't say yes right away, and instead asked questions about what she imagined it would be like, and before she knew it he had her at the edge of orgasm again imagining him watching her as he commanded her. By that time she would have done most anything to get him on the video right then and there, but he was on his phone at an airport, so they decided to try the next day. He told her that she was to play with herself at every possible moment over the next 24 hours, but under no circumstances was she allowed to orgasm.

So here she was, rushing home to have online sex with some stranger, trying to subtly reach under her skirt and tease her clit while she drove. If she hadn't been so horny she could cry, the whole thing would be laughable. Finally, she got to the small rental bungalow she shared with her roommates. She prayed to God things hadn't gone off plan with Anna or Keely. This just wouldn't work if they were home. Thankfully, the house was empty and she rushed to her bedroom to get ready. She liked her outfit of a sheer teal blouse over a black camisole and a floral skirt that came to just above her knees. Underneath was a very pretty turquoise bra and panty set. It was a little dressed up for babysitting, but now she thought showed her off just right. Pretty and a little bit sexy, but not slutty. She pulled her hair out of its ponytail, allowing it to drape over her shoulders, almost to her breasts. She spent a few minutes touching up her makeup to go from her everyday mode to a hot date mode, and before she knew it, it was time.

She opened her laptop, started the video chat program, and waited for him to join. She felt that since he was the Dominant, it only seemed right that she be waiting for him. Thankfully he was on within a few minutes, since she wasn't sure how long she could sit there without chickening out. As soon as his face appeared, she felt like her brain completely froze and she was struck speechless. On the good side, he was more handsome than she had really expected. He was older, maybe early forties with close trimmed salt and pepper hair, but he looked trim and fit. And at least from what she could see of his button down shirt and reasonably stylish glasses, he appeared to have an acceptable fashion sense and had put some effort into dressing nice for their "date." The problem was the weirdness of what they were doing hit her like a ton of bricks as soon as he connected, and she felt awkward as hell.

Fortunately he jumped in and started talking right away, relieving her of the need to think for a minute or two. He complimented her on how nice she looked, and even made her step back so he could see her skirt.  Heather felt herself blushing, but was inwardly pleased by his wolf whistle as she pirouetted for him. They talked for a little while about how her nannying job had gone that day, about the traffic on the drive, about the weather in Colorado, about how they were both glad that the other one wasn't really a 300 pound high school kid living in his Mom's basement, and anything other than what they were about to do. Within minutes she found herself relaxing, even smiling and giggling as they talked. He was witty and kind, his smile was contagious, and she was relieved that this was going every bit as well as their IM chats had.

After a few minutes, he did start to steer the conversation towards sex. He asked how well she had done on her assignment to keep playing with herself, and she told him that she had been working at it, even doing it in her car.

"Well, I'd be more impressed if you had done it with your window open instead behind tinted glass," he winked, "but I suppose it does show you've come a long way."

Heather rolled her eyes and stuck her tongue out at him.

"So does that mean you don't have any panties on under that pretty skirt?"

"Oh God, no. That would have been too crazy. I kept them on and rubbed myself through them. And stop making those faces at me - I did the best I could. You said yourself I'm making progress!"

"Did I say that? I don't know what came over me," he teased. "So what kind of panties are they? How did they feel on your clit? It must be sensitive now with all that playing and no relief."

Holy fuck, Heather thought, it's really starting. If she was ever going to back out, this was the time. She thought briefly about just disconnecting and never communicating with him again, but she knew she wouldn't do that. She wanted this, and she knew she wanted to do it with him. She liked him and trusted him, and knew this was the right thing to do.

"They're satin. It feels really smooth when I rub it," she clenched her legs together just thinking about it.

"Don't you want to show them to me?"

Although it was phrased as a request, it was clear that it was anything but. This was his way of being polite, but she knew he was absolutely serious about this. Keeping her legs together, and unable to maintain eye contact with him, she looked down as she slowly pulled up her skirt.

"Good girl. I could see them a little better if you lifted the skirt up a bit higher" 

It was ridiculous how being called a good girl elated her. It shouldn't be that easy, she thought. No matter though, it pleased her so much that she pulled the skirt up so he could see her panties from waist to crotch..

"Very good. Why don't you tuck the skirt into its front, so you don't have to worry about holding it."

Like she was actually worried about that! But she liked doing what he wanted, so she tucked it in. Their conversation resumed, making ups some more stories of tribulations for Elaine, and they both acted like Heather wasn't sitting there with her panties on display for him. A while later he asked to see her camisole, and it wasn't long before she was taking off her blouse as well. He complimented her both on the camisole, and on what he referred to as her "rockin' body." The compliment made her smile. She had always been self-conscious about her body; she always felt she was too skinny at 93 lbs. She was only 4' 11", so that wasn't a ridiculously low weight for her, but she wasn't the curvy kind of girl that seemed to get guys attention. Seeing him so pleased to peek at her body was thrilling to her.

The story they were making up about Elaine, which involved her Master taking her to strip club, kept getting hotter and more explicit. Heather's thighs kept bouncing together as she got more excited, and a few times she stroked her exposed thighs.

"You seem pretty excited. Wouldn't it feel better if you rubbed your pussy through your panties?"

"Okay.  I guess. Mmmmm.... Shit that feels good. Now I'm just worried I'm gonna cum."

"No cumming," he was quite stern. "You are allowed to stop if you might cum, but I think you can gently stroke it and be safe enough."

Easy for him to say! Nonetheless, she began to trace her finger up and down her slit through the smooth material of the panties, occasionally swirling it around her little button. He made her keep her legs spread very wide as she did it, and it surprised her how humiliating it felt to be holding her thighs as wide as she could and rubbing the crotch of her panties. She wasn't showing any more that she would show in a bikini if she sat crisscross-applesauce, and she was barely grazing the gusset of her panties with a fingernail. What made it different was how he was watching her, and she was doing it because he told her to. That changed everything. She found herself staring into his blue eyes, her adrenaline rushing at the idea of being watched, and listening to his words. She imagined what it would be like to be Elaine, to be forced to join the strippers on stage, to pay for a lap-dance, or to have to service their pussies with her mouth. It was all a crazy fantasy, but it was all so erotic. Combined with him really watching her, it was getting her very hot and bothered.

"You're looking a little warm there," he interrupted. "Wouldn't you feel better if you took your bra off?"

She giggled at the way he made it sound like a question. She knew she couldn't refuse him; she didn't even want to. She made a sexy show of removing the bra from under the camisole, sliding off one shoulder strap and then the other, followed by turning her back to him as she shimmied it down under the cami and unclasped it. She continued to tease him by keeping her arm covering her breasts as she turned back to face him. He scowled at her, making her laugh out loud before lowering her arms. Her breasts were not large, (nothing about her was large) but she had often been told her B cups seemed big on her tiny frame. She was self-conscious about not wearing a bra, not because her breasts really needed support (they were definitely perky), but because her nipples were very prominent, and would show through most coverings. She was extremely excited right now, and the cami was light colored and almost sheer, so it really did nothing to hide the shape and color of her achingly hard nipples. He leered at them and complimented them profusely, which made Heather feel warm and squishy inside. 

After ogling her for a bit, he decided he wasn't sure her nipples were as hard and prominent as they could be, so he made her tease and tweak them to see if they would stand up any more. Heather was pretty positive that they looked exactly the same after a few minutes of pinching and teasing through the fabric, but the experience left her flushed and breathing hard.

The story of Elaine was getting very kinky now, and Heather was making a point to show off and tease him with her body as he elaborated the fantasy. He finally asked her to untuck her skirt, and remove her panties. This left her feeling exposed in just the camisole and the skirt, but she wasn't actually showing anything. They went on a little further in the story, and she started slipping her hand up under her skirt to play with herself. Finally the moment of truth arrived, and he had her take off her skirt.

"Ahhh... shaved... very sexy," he seemed pleased as she stepped out of the skirt.

"No, waxed," she smiled. She had kept herself totally bare almost since she started growing hair there. "It keeps it much smoother." She rubbed her hand along her pussy lips to illustrate the point. Just that gentle caress got her to bite her lower lip and rock her hips slightly.


The Perils of Being Too Trusting Ch. 02



It took almost an hour before Heather decided what she was going to do, and could log into the video chat. While she found the concept of being blackmailed arousing, the reality of it happening now was just too scary. She couldn't risk ignoring him either, so she decided to get on and beg him not to do this. She didn't get undressed, and she just sent a quick chat message: "We need to talk." He logged on a few seconds later, but he didn't turn his cam on. His voice made it very clear that he did not approve.

"You're testing me. You don't think I'm serious," was all he said.

She started to beg him, but he logged off before she could even say anything. A few seconds later he sent her an instant message.

"It will take about 15 minutes to upload this video to a popular porn website. If you comply with instructions before it's fully uploaded I might cancel the upload."

Heather was in a panic. He didn't even give her a chance! She didn't have any time to figure out her next plan, she had to stop that video upload. She almost ripped off all of her clothes, and it was less than a minute later when she sent him the message that she was ready to serve him. Her heart raced as she typed those words. Ready to serve him. What would that mean? She decided she would have to play along with him as long as he didn't try to make her do anything too wrong. And then use her charms to convince him to stop all this. It wasn't much of a plan, but it was the best she could do at this point. 

He was back on again quickly. She still couldn't see his face, but his voice seemed much less perturbed. 

"Much better," he said. "Put your hands on top of your head and stick out your chest. Good girl. Keep your legs spread. Okay, I guess I can cancel this upload for now. But it won't take much for me to restart it."

"Okay, I get it," Heather's frustration leaking out, "but please, we need to talk about this. This is crazy, this was all supposed to be fantasy, this doesn't happen in real life."

He was clearly not impressed.

"It seems like you're a bit confused here about what this really is. You may think this doesn't happen in real life, but it is going to be happening to you. In. Real. Life. And you'd better adjust your attitude, or this is going to be very tough on you. You've read enough of my stories to know how I like to be addressed. Do you want to try that again."

"Are you shittting me? Really?" Heather couldn't really get her head around what was happening. By his silence, she realized he was really serious. She knew what he wanted. She had read it in dozens of stories, of girls in this position, naked, hands on top of her head and legs apart, forced for the first time to say the words. It always seemed so minor in the stories, but it was shocking to her how hard it was to say, now that it was her, and it was really happening.

"Yes Sir," she said, shocking herself how quietly it came out.

"Much better. Now, are your roommates at home?"

"No Sir."

"Good," his voice brightened. "Bring your computer with you, and give me a full tour of where you live."

It felt very strange walking around her house naked, even with the house empty. She gave him a view of her room, including at his request a quick look in all her dresser drawers and closet. He gave her a promise there would be plenty more time to examine her wardrobe in detail, and they moved on to her bathroom. She explained that she had won the coin toss when they moved in, so she had the master bedroom with attached bath while her roommates shared a bath. He asked her if the window in her tub/ shower opened, but thankfully he didn't make her open it right away since it looked out at the bungalow less than 20 feet away. Not that it mattered, because he had her walk straight out to the kitchen. She thought about protesting, but she knew that wouldn't get her anywhere. He had made it very clear that she was already in trouble for her attitude before, so she just tried to be careful to stay away from the windows. She showed him her kitchen, the dining and living room at the front of the bungalow, and where her roommates' bedrooms were. She was getting ready to argue with him that she wasn't going to show him anything about them (she was in enough trouble without bringing them into it) but he showed no interest other than figuring out where their rooms were in relation to the rest of the house.

In the end he had her go back to the living room, setting her computer on the coffee table facing the front windows, and kneeling with her legs spread so he could see all of her. It made her really nervous to be so close to the windows and the front door, but at least the windows had sheers so it would be hard to see in and her roommates weren't due home for hours. But if anyone did walk in, she'd be sitting right there for them to see in all her glory. She was ashamed that just thinking about that turned her on a bit, but thankfully he didn't know that. 

"Okay, time for us to have some fun," he had a small smile on his face. Somehow she didn't think this was going to be much fun. 

"Let's begin with some ground rules. If you are home alone, I expect you to be naked all the time. You will log into the chat server and set your webcam to broadcast. I may or may not log into check on you, but you never know when I will, so you need to always be broadcasting."

"But what if someone else starts watching it?"

"You need a new login anyway. NawtyTeeze doesn't really fit you anymore. I've made you a new one as NawtySubSlut. Suits you better, don't you think? I am emailing you you're new log in. Since I should be your only friend, no one other than me should see your webcam. Unless you start giving your new nickname out to a bunch of strangers that is."

Heather was not at all convinced, but she didn't really see how she had any choice.

"Yes Sir."

"In a little bit we'll pick out some clothes for you to wear if someone comes to the door, or for when your roommates get home. If anyone shows up before then, you may get a towel. It might be a bit difficult to explain why you're in a towel while completely dry, but that's probably easier to explain than why you're naked in your living room."

Again, in spite of herself, Heather felt a warm surge at the thought of being trapped in just a towel if someone was at her door. 

"Next, I need to know a little more about you. What's your real name?"

"Heather."

"Heather....? I expect full answers my little slave, and don't forget to show me respect"

"Sorry Sir, Heather Eastman, Sir." She couldn't believe she was doing this, but it was all moving so fast.

"It's not that I don't trust you, but you're just starting out in your new role. I need to verify that. Do you Facebook?"

"Yes Sir."

"Give me your Facebook log in and password -- I want to look at your pictures."

"I can't do that," she protested. " You're crazy. You could post all kinds of stuff, saying it was me. I'd be worse off than if you just posted that video. Why would I do that? Just look me up in public, you don't need my password."

"Come on now," he was dismissive, "you know how this works. I know there's no way that I could get you to do something that would give me any more leverage than I have now. But think about it. If I did something like that now, all our games would be over. I just want to look through all your pictures, even the ones that you share only with your closest friends. I'll let you change your password to something new here in just a little bit. You're going to have to trust me."

"Trust you?!? Look at what you're doing to me! Why the fuck should I trust you?" she was almost screaming.

"Temper, temper there my new slave, you don't know what kind of trouble you might be getting into by being so mouthy. Obviously you can't trust me in the normal sense, but you know me and you know my stories. You know I wouldn't do anything that would end me playing with my new toy. Especially on the first day."

She stared at the floor, her mind in complete gridlock. She knew if she refused, he would put that awful video out on the web. But part of her kept thinking that giving him control of her Facebook, giving him the rights to post things in her name , that he might do something really terrible. But the more she thought about it, the more she thought he was right. He wouldn't ruin this opportunity as fast as he got it. He had her naked on camera, and it was clear that he wanted to do more. She decided to give him what he wanted, resolving to change her password this afternoon no matter what he said

"Good girl. Now let's take a look. Well hello Heather Eastman. Good to know it's really you. And you do actually live in Colorado Springs. Nice to know that was the truth. I'll look at your pictures more in a bit. First we have to deal with some of your disobedience. First off you weren't naked when I told you, and there have been several times when you knew better and you haven't called me Sir. You know what that means don't you?"

Heather was silent. She was terrified that after all this he would still post that video and ruin her.

"I asked you a question slut!" his voice rising.

"It means I need to be punished, Sir. B... Bu... But you said you couldn't post the video. That it would ruin your fun. Please, Sir," Heather felt like she was losing control.

"I'm glad you're showing the appropriate level of concern now. Keep that in mind when I tell you what to do from now on. But for now, your punishment will be very uncomfortable but nothing near that bad. First I want you to open all the blinds all of the way. We'll do your bedroom later, but for now get all of them open."

"But my neighbors, anyone in the street will see me! How is that any better than you just posting the video. I know those people. It's not like the internet."

"Hate to break this to you slut, but this is your new reality. Sooner or later your neighbors are going to see you naked. So will your roomies. At the very least you're going to be known as that girl who gets naked a lot. But that seems a lot better than that girl who works as a babysitter but is actually a pedophile, don't you think? Now it's time to face up to your new reality, and get those windows open. You keep arguing and you're just adding more time to your exposure, not to mention the next phase of your punishment."

Heather could see that he had her. It seemed crazy that she could be blackmailed into doing something humiliating for fear of being exposed as having done some other humiliating thing, but he was right. The video he had was way worse than being seen naked by the neighbors. She resolved to stay mindful of that, and make sure she never gave him anything worse than what he already had.

"Good girl, get them wide open. Don't use your hands to cover yourself. If anyone gets a view, it's just their good luck. So any families living nearby? Small kids?"

"No Sir," she replied. "It's mostly all students. Maybe a few recent grads like us. No families."

"Good. Now come close to the camera, show me a close up of your cunt."

Heather winced a little at the word cunt. Even though reading stories about women being forced to talk whorishly turned her on, she always found the word shocking when said out loud. Even more shocking was the view of her vagina up close on the screen. There was no denying that it was swollen, and it was clearly visible on her screen how her inner lips were opening up. It would be totally obvious to him that in spite of how upsetting this was, she was very aroused. 

What the fuck was wrong with her?

"Very good," she could hear the smirk in his voice. "I see at least a part of you finds this... uh.. stimulating."

"Please... please Sir," Heather wanted to beg him to stop, to not do this, to not humiliate her, but somehow she didn't know how to start. She had tried everything.

"Aww now, my little subslut. It's going to be okay. I know this is going to be hard for you, but I promise it will be bearable, and if you cut loose and trust me a bit, you might even have fun. Now I want you to go to your front windows and put your hands on the window sash. Stand there with your legs spread wide and tell me what you see out in front."

"Oh God... you can't be seri... oh Fuck," Heather's voice failed her.

Slowly Heather moved to stand at her window, covering her nakedness. It took more will than she ever could have imagined putting her arms up on the window sash. The feeling of exposure was so intense it made her shaky.

"Tell me what you see."

"Fuck, I don't know," Heather felt the panic setting in. "I can see up and down the street, there are cars parked on both sides. I can see all the houses across the street."

"Any people you can see?"

"Not right now. Oh SHIT!!! A car's going by!" 

It was all Heather could do to not scream and cower below her window.

"Stand still!" he commanded 

She refocused her mind and she was able to avoid attracting attention as the car drove by. It cruised by steadily, and there was no indication anyone even noticed her in the window. 

"Okay, I'm starting a ten minute timer," he explained. "You are going to stand there just like that no matter what. The only excuse you can have to move is if someone comes to your front door. Then you may go get your towel. But beyond that you stay as you are, even if your neighbors are staring at you and clapping. Am I clear?"

"Please Sir, I don't like this. I'm terrified." 

"This is a punishment slut, you are not supposed to enjoy it. And this is not even a very serious punishment; I promise you it will get far worse than this. But I told you that you could tolerate it, and you will. Now keep looking out there, let me know if you see anyone drive or walk by. And I'll go back to your pictures."

Heather tried to stay as still as possible to avoid attracting any attention. Several cars drove by, but thankfully no one seemed to be noticing her. At least the sun wasn't shining in her window so she was in the shadows and probably hard to see. She could barely pay attention as he commented on her photos. She had a couple of her in bikini that he seemed to like, but pretty soon he told her that he was satisfied and she could change her Facebook password.

"You might notice have a new friend," he let her know. "Mike Smith is now one of your most trusted friends. That way I'll be able see everything going on in your life. I will check from time to time, so I wouldn't change your privacy settings unless you like being punished."

Heather assured him that she understood.

"So while you're just standing there, let's discuss more of your rules. You told me you always wax your cunt?"

"Yes Sir. I have since I was a teenager. I've read your stories; I know I need to keep it perfectly hairless."

"Not so fast my little subslut. Actually I want you to stop. No waxing, no shaving, nothing. It'll be fun to see what you look like with a hairy pussy."

"Huh?" Heather was genuinely confused. "I thought you liked girls bald down there?"

Her comment elicited a genuine laugh. If it weren't for the fact that he was blackmailing her and humiliating her, she would have thought what a nice laugh it was.

"It isn't about the hair," he explained. "It's about doing something that you don't want to do. About submitting to my control. Plus it's something to keep you focused on your cunt. The girls in my stories had always had hairy bushes, so shaving helped them focus on their pussies. For you, it's the other way around, now the itching and stubble should keep reminding you that you can't make your own decisions."

"And speaking of making sure you stay focused on that lovely cunt of yours," he continued, "it's time to move on to the next phase of your punishment. Move your computer to the left side of you so I can see your whole body in profile." 

Heather was glad to have a brief reprieve from being totally exposed to her street, but within a minute she was back in position with her hands on the window sash and her legs spread wide. Only now her computer was on the floor, the camera looking up at her naked body from the side. 

"Okay, now I want you to take your right hand and use two fingers to finger-fuck yourself. C'mon, get a move on it. I know your pussy's soaking wet, so they should slide right in there. Good girl. Keep looking out that window. I want you to see anyone who is watching - anyone who sees you banging your cunt right out in the open like this. Use your other hand to play with your left tit. That's it, pull and pinch that nipple. Keep your eyes on the street. Just think how this looks, you standing where anyone could look in and see you. Just wait, maybe someone will walk by, see you fucking yourself, looking like a total slut."

Heather was awash with conflicting emotions. While she was horrified that she was being forced to act like a cheap whore, the sensation of her middle and ring fingers sliding in an out of her pussy combined with the exposure she felt was actually bringing her close to orgasm. As humiliating as this was, it would be way worse if he saw her cum from this, so she slowed down the motion of her fingers, plus she pinched her nipple even more cruelly. It was still sore from yesterday, so the pinch helped take some of the momentum off. 

"You're slowing down subslut -- what's up with that?"

"Please Sir, let me stop," she was actually panting a bit now. "This is so humiliating."

"This? Really? This is nothing. Imagine how you'll feel if you have to do this with your tits pressed up against the windows. Or may fucking a dildo stuck with a suction cup to the window. Now THAT would be humiliating."

"Ohhhh.... Gawd!" Heather panted. Her head rolled back and she fucked herself more vigorously as she imagined being forced to behave like a wanton nymphomaniac.

"Don't cum!" he commanded sharply. "You should know very well you are not allowed to cum without permission. Slow down as much as it takes, but keep going. I want to ask you some questions now. Do you have a boyfriend?"

"You know I don't, Sir."

"I know you told me you didn't, but I just wanted to give you a chance to change your story. Just so we're clear, if anything you told me before today was not true, there are no consequences provided you come clean with me now. Any lying from now on will be severely punished. Am I clear?"

"Yes Sir. I do need to confess something, Sir. I told you I got naked with my windows open here, and that I went outside naked. I never really did that before. It was too scary."

"And here you are doing it right now," he chuckled. "Kind of ironic, eh? See, it really wasn't that scary."

Heather decided staying silent and fingering her pussy was better than any reply to that remark. 

"So no boyfriend? Girlfriend?"

"No Sir, up until a year ago I had a fuck buddy, but he moved away."

"So you haven't had sex in a year?"

"No Sir, it's been weird since graduation."

"But you have had sex with a woman in your past?"

"Five or six times, also before graduation. They were pretty much all one night stands," she felt herself blushing as she answered.

"You've had anal sex?" he changed topics. "Were you telling the truth when you said you like it?"

"Sometimes I do like it, Sir. If it's done right and I'm in the mood."

"Hmmm, I'm not sure whether or not you are in the mood will matter going forward. Ever had sex in a public place?"

"No Sir, at least not before right now," she answered seriously, even though it elicited another chuckle from him.

"Do you have any sex toys? Vibrators? Dildos? Butt plugs?"

"No Sir."

"Really?" he seemed genuinely surprised. "You just don't like them, or don't masturbate that often?"

"I've always been too embarrassed to buy them. I do masturbate -- probably close to every day."




The Perils of Being Too Trusting Ch. 02



"Good girl. You'll be doing that even more from now on. Although you won't be getting the orgasm at the end of course. Have your roommates ever seen you naked?"

"Not at home, but Keely and I did go skinny dipping once."

"Have you seen them naked?

"Only Keely when we were skinny dipping."

"Is she hot?" he asked in an offhand tone that made her giggle in spite of herself.

"She's pretty Sir. I didn't make that up."

"Okay, I think that's enough from now. You're looking like your starting to get comfortable being such a perv, so I think we should move on."

Gratefully Heather stepped away from the window, put her laptop back on the coffee table and followed his instructions to kneel in front of the camera with her legs spread wide. It was still embarrassing to be spread so wide for him, especially now that her pussy was swollen and open from her fingering. She was no sooner in position than he gave a clue as to the rest of her punishment.

"Okay, now run to your kitchen and get a wooden cooking spoon, or if you don't have that, a spatula."

"We have a plastic cooking spoon, Sir."

"Go get that. Run." 

When she was back in front of the webcam, he had her turn around and kneel with her butt pointing at the camera. He told her she needed to give herself ten swats to each ass cheek, warning her he wanted to hear a loud smack with each spank, and he would be watching for her skin to redden. If he thought she was faking it, she would have to keep spanking herself until he was satisfied. In addition he expected her to count the spanks out loud and thank him for each one. 

Grabbing the spoon firmly, she raised her arm high, and brought the spoon down as hard as she could on her ass. She was shocked how much it stung. It was way more painful than she had expected, although she was in uncharted territory here so she didn't really know what to expect. She almost forgot to count it and say thank you, but she remembered to say it just before she was about to give herself the second blow. Unfortunately the second time her body rebelled and her arm came down much more gently than the first blow.

"Oh c'mon now Heather, you can do better than that. Let's do that one over," he chuckled. Heather didn't find anything funny about it as she struggled to spank herself hard enough to satisfy him. 

"Owwwweee... shit...," she grunted. "Two. Thank you, Sir."

She gritted her teeth, struggling through each blow. It wasn't until she started on her left cheek that she worked out that she should move around where she hit to keep from focusing on just one spot. In the end she ended up having to give about 5 extra spanks to satisfy him that she was doing it hard enough. Finished, she sat down gently on her tender ass.

"Now that is no way to sit my little subslut. You know how sluts are supposed to sit"

Heather quickly returned to kneeling with her legs spread wide, awaiting his next instruction. It didn't take long.

"I was going to let you off easy this afternoon, but as punishment for not sitting as told you'll need to give yourself ten swats from the spoon on each of your inner thighs. Same rules. Start now."

Heather wanted to argue, but she knew enough to know it would just end up with her getting more spankings. This time she only had to repeat two swats to satisfy him, and she could see her inner thighs were red from just above her knees all the way up to her crotch. 

"Good girl, you're getting the hang of this. In a minute we'll get back to the punishments for your earlier transgressions, but right now I want to see if you're still turned on. Are you still wet? Show me a close up of your lovely cunt."

Heather wasn't exactly sure what the effect of all the spankings would have on her arousal. She knew she was still very turned on, but even still she was surprised how easily she was able to insert first one, then two, and then even three fingers in her very wet pussy. Somehow all this was turning her on even more, and SpareRod's comments about what a wet and horny slut she was made her even hornier.

After a few minutes of finger fucking herself, she had to beg him to let her stop, just so she wouldn't cum. He agreed, and they moved back to her spankings. Having read his stories, Heather wasn't too surprised that his next target was her breasts. Even though she half expected it, the idea terrified her, especially with her nipples being so sensitive after yesterday's abuse.

"So you need to give 10 swats to each breast. Now, I will take it a bit easy on you, and I want the first 8 anywhere on your tits except your nipples. Do each tit completely first, I want to see both of them fully red before you do your nipples. Then you have to do the last two on each nipple. Remember, if you don't do a good job, we'll keep at it until I'm satisfied."

"Sir.... My nipples... I've never done this, and they're really tender from yesterday," she protested meekly. 

"That's why this is a punishment. Now get to it."

Putting her left hand on her head, Heather began swatting her left breast with the spoon. It definitely stung and was uncomfortable to feel her breasts wobble and sway as the spoon struck. It was even worse when he had her pull her nipple up so she could strike the underside of each tit, but at least it wasn't as intense as she knew it was going to be when she moved on to the nipples. She ended up having to repeat two swats on her right boob, since she wasn't very good with the spoon as a lefty, but in general he seemed pleased with the way her breasts were now a splotchy red. She started to panic about what would happen if Keely or Anna came home any time soon. This would be very hard to explain with her red butt, legs, and boobs. 

"Now for the last four on the nipples. Make them count."

Heather was shocked by the loud screech that came out of her mouth when the spoon smacked forcefully into her tender nipple.

"MOTHERFUCKER! Holy FUCK, that smarts!" Heather shrieked and caressed her abused nipple.

"Do you want to try that again? That's not the way a subbie slut should count."

Heather swore again as she braced herself to resume her punishment. It took her five tries to get two spanks on her left nipple, and actually seven tries to get the two on her right to his complete satisfaction. Her eyes were watering a bit, and her nipples were screaming and throbbing.

"Let me see your cunt again. Hmmm... Looks like your cunt didn't like that nearly as much."

"Fuck no... no, Sir," Heather was still turned on, but her pussy lips here notably less swollen. "That hurt like a motherfucker."

"Good to know we've found some true punishment for you. Something for you to remember next time you think of being disobedient."

"Yes, Sir," is what she said out loud, but inside her mind she was screaming profanities at him.

"I was going to have you swat your pussy too now, you know how much I like that, but I think we'll keep that in case you need to be punished again. Unless you want to try how it feels to be swatting that cute little cunt of yours?"

"No Sir, thank you Sir," she replied quickly. She was definitely glad to give that a pass.

"Okay, but if I see any disobedience, any hesitation, and we'll be right back here, using that spoon directly on your clit. Understood?"

"Yes Sir, thank you Sir."

He instructed her to head to her bedroom, where her first task was to raise her venetian blinds completely, totally exposing her to her neighbor's house. It was still light out, so she took some comfort that no one could see in that well. Plus, the only window that lined up to see in her window was in a back bedroom and had its blinds closed, so it was unlikely the college kid next door would see her.

"Good job my little subbie slut. Just so you know, I expect you will never close those blinds again. If your roomies aren't home, you'll be naked here, and if they are you'll likely be dressed like a trollop, so I guess you'll need to get used to being exposed."

Heather's stomach did flip flops at the thought.

They spend the next hour going through all of her clothes, modeling them for him to decide if she could keep them or not. Clothes that were acceptable went back into her dresser or back on hangers; clothes that were not went into giant trash bags. First they did T-shirts, and he checked each one to see how prominently her braless breasts and nipples showed through the fabric. He took the opportunity to make her pinch her tender nipples some more, just to be sure they were hard. Only the most scandalous shirts survived. Similarly blouses needed to be tight, or sheer, or button up the front, or all of the above. He had her get a pair of scissors and cut the buttons off of several blouses so they were open to below her breasts. She also modified a sweatshirt to be so far off the shoulder that it was almost impossible not to expose herself. 

Most of her dresses survived, although he had her cut out the lining from a couple, even though that made them totally obscene. She was sure she would never be able to wear them again. At least she hoped she would never wear them where anyone would see her. Next came the skirts, and she was able to keep most of the ones that ended above the knee. He asked her if she had a way to hem them any shorter, and she had to admit that she had a sewing machine that her mother had given her when she turned 16. She didn't use it very much anymore, but under his questioning she let him know that she could hem a skirt.

"Good to know. I see you wearing some shorter skirts in the future. But we'll leave that for now."

Next, all of her jeans went into the bags, except for a few super tight skinny ones, and one older, holey pair that he had her modify and model for him. She had to cut off the belt line so they would no longer button, plus she cut a patch out of the crotch so her pussy lips were completely exposed. If she stood with her legs closed very tightly it wasn't too obvious, but she couldn't even imagine wearing these around the house, much less where anyone could see her. He also had her cut the crotch out of a couple pairs of tights, but left the rest alone.

Finally they went through her underwear drawers. Most of her bras had some padding and he had her throw those in the bag. He only allowed her to keep two lacy and one sheer bra where he could see her nipples clearly through the cups, although he kept her pinching her poor nipples to help in his judgment. Her camisoles and slips all survived, although he commented that it was more likely she would be wearing them as her only clothing rather than as undergarments. All of her panties had to go except for three thongs, two very sheer lace panties, plus a pair of leopard print boy-shorts. He also had her model a couple sexy teddies an old boyfriend had bought her. SpareRod seemed to like those quite a bit since he made her put on a pair of heels and walk around in a teddy that wasn't much more than some strategically placed patches of lace combined with a string between her ass cheeks.

"Just imagine having to walk around in front of Keely and Anna dressed like this. What kind of slut will they think you are? Just think how humiliated you'll be."

"Please Sir, don't. I don't think I could bear it."

"Oh, I think it would be better they think you're a weird chick that likes to hang out naked or in lingerie and heels, than a deeply weird chick who wants them to piss all over you. Don't you think?"

Heather couldn't answer and just stared at the floor. She could feel her lip trembling a little.

"Well, we won't be doing that today. But keep that trade-off in mind. Sooner or later your roommates are going to see you in some pretty embarrassing situations. Not as bad as it would be if that video became public, but definitely embarrassing. You'd better think about how important it is to you to keep that video secret."

"I know Sir, but please one of them should be home soon, and I'm getting scared. I don't want to make you mad Sir, but I'm not sure I'm ready for her to catch me naked or worse. I'm scared I'll say something... please Sir," she started to tear up she was so upset. 

She hoped it was enough.

"Don't worry my little subslut. I know this is hard on you. Actually that's what I like about it. But I told you I am in this for the long haul, so we'll work our way up to some things. Don't get the idea that you can beg me for things and I will relent though. So as compensation for me letting you get dressed, you need to give each nipple two more hard swats with the spoon."

Heather groaned, but the possibility that she might get dressed soon motivated her. Even though it took 3 swats to her left nipple and 4 to her right to satisfy him, it was worth the stinging pain in her breasts since he started on getting her dressed as soon as she was done. He had her try on the leopard print boy shorts and a pale pink t-shirt that didn't actually meet her panties at her waist. Her ass cheeks hung out lewdly from the boy-shorts, and there was no way she could pull the shirt down to provide any modesty. And while it wasn't like she could see the color of her nipples through the shirt, it left no doubt she had nothing on under it.

"Perfect. I think that will be a good start to get your roommates used to your new dress code. If they ask about how you're dressed, I would make sure they know you'll be dressed like this or in less from now on. Now, are you going out anywhere tonight?"

The butterflies in Heather's stomach went on rampage thinking about how she would explain being dressed like this to Keely or Anna, but she pushed that thought aside for the moment.

"No. No plans tonight, Sir."

"And tomorrow?"

"I'm working at the restaurant from 6:30AM until 2:00, and then I'm babysitting from 5:00PM until late here in the Springs."

"Okay, we'll need to pick out some clothes for tomorrow then. Any dress code to be a waitress there?"

"We all have to wear white blouses... that's it. Oh, and my tits and pussy need to be covered. Sir," Heather couldn't avoid the sarcasm.

"Aww. That seems totally unreasonable," he didn't even miss a beat. "Nonetheless, we'll see what we can do. Let's try a jean skirt, that sea-green camisole, and the white blouse we cut the buttons off of. Let me see how that looks."

Once she was dressed as he asked, Heather was somewhat relieved. The blouse was heavy enough that even with just the cami under it her nipples were concealed. With the buttons cut off the blouse was more open than she'd like, but with the cami underneath it seemed modest enough. The jean skirt was actually one of her longer ones, just an inch or so above her knee, so even without panties it wasn't too crazy.

"That will work fine. Be sure to take the lace panty and bra set with you. When you get to your babysitting job you can put the underwear on, but only while you're babysitting. As soon you get back to the car you need to take them off. Now get back in the boy-shorts and the pink shirt."

"Yes Sir. Thank you for the underwear Sir," Heather said meekly. She was somewhat repulsed by her gratitude at simply being allowed to wear underwear, but it was genuine.

"Moving on, you must stay out of your room until 10:00PM tonight. The only excuse you have is if any guys come to the house, then you may go to your room. I don't care how you explain how you're dressed, but I wouldn't let anyone know about me if you want to keep all this secret."

"I understand Sir."

"Remember while you're home, I want your webcam broadcasting and focused on you. You are allowed do what it takes to keep your roomies off camera, but I want to watch you all night. Once you're in your bedroom at 10:00, I want you naked again, and I want your webcam on all night. I like the idea of watching you sleep naked with blinds and door open."

"My door open?!?"

"Another rule. You are not allowed to close your bedroom or bathroom door again without my permission. Get used to it. Just so you know, I will be adding rules that will require you to play with yourself at certain intervals. You'll need to play your cunt and your tits for the camera to prove to me you are complying. For tonight we'll just say you should do it as often as you can. If I don't think you've finger fucked yourself enough when I check in, you'll be punished tomorrow. Understand, slut?"

"Omigod, Sir! How can I do that with my roommates around? Please," she begged.

"Don't get caught. You'll figure out a way, just be sneaky. But I'd better see you edge several times tonight, or you will pay. The last bit for now is that tomorrow I want at least one pic sent to me every hour, never more than 90 minutes apart, showing me that you are dressed appropriately where ever you are. That means showing me clearly that you have nothing on other than what I told you, and that you are wearing it in public. So the pics need to be clearly in public, and it needs to be clear that you have no underwear on. Understood?"

"But Sir... at work?"

"Don't do it during babysitting, but yes, between waiting tables, I expect you to snap me some quick selfies that show off your cunt and your tits to prove you're not wearing anything you shouldn't be. It's okay if it takes two or three pictures, just so I can know you are following instructions. And it has to be obviously a public. No bathrooms, no cars. Clear?"

"Oh God Sir, I don't know how I can Sir," she begged.

"Are you really going to make me remind you of how you don't really have a choice?"

"No Sir, I'll do my best Sir," Heather felt overwhelmed. For a second she thought she might faint.

"Good girl. I'm going to go for a bit, but I may log in later. I may or may not say anything, so you need to be prepared. Make sure you are always on camera. Or there will be consequences."

And with that, he was gone.

* "Dumb fucking luck!" Brad pushed his chair back, running his fingers through his hair.

She would never know how close he had been to chickening out. Even before he had sent the email he was certain he wouldn't actually make the video public. If she refused to submit, then it meant she wasn't really a submissive, and he wouldn't have anything to gain, and if it went badly he could easily go to jail. It amazed him that he had stayed firm -- it was so unlike him.

In spite of his years of writing kinky stories, Brad had to admit that real life to date had been pretty vanilla. During his marriage, his sex life had been extremely traditional, which in retrospect was a big part of what ended it. He had been totally caught off guard when Carrie had announced she was leaving him, that she was sexually unsatisfied. Early in their marriage she had made it very clear that she did not share any of his kinky fantasies. She was strident that she never wanted even talk about things like public exhibitionism, bondage, or anything kinky, much less explore them. He had accepted that, since they were compatible on so many other levels, and they had settled into a traditional routine, always having sex in their bedroom, with the lights off, and always in the missionary position. He didn't find it hugely satisfying, but it was still sex, and he loved Carrie dearly. So the affair had cut him deeply, he had never even imagined that Carrie could do that. Worse than the affair were her reasons for it. She said that Jorge was passionate, that he had reawakened her lust, and that should just couldn't go back to the boring life she had had with Brad.

Luckily for him, things had really taken off at about that same time at the small start-up where he was working. Not only had that worked out well for him financially, it had also allowed him to throw himself into his work as a coping mechanism. It had taken a few years before his bitterness had declined to the point where he could contemplate dating again, and even at that he had never trusted enough to where it ever went anywhere. It had been easier to just retreat into the world of fantasy, along with the occasional online chat. A couple times he had considered exploring his kinks more directly, to go to a BDSM club, or to use a kink-specific singles site to meet someone he was more in tune with, but he had always ended up chickening out. So in the last ten years he had dated only sporadically, mostly from friends setting him up, but he never really made a strong connection. Mostly because he was never confident enough to even mention his interests, much less act on them.




The Perils of Being Too Trusting Ch. 02



That was probably part of the reason he had tried something as risky as blackmail. It was totally unlike him, and dangerously reckless. He had built his career and so much of his life by being careful, and planning for all possible contingencies and consequences. Here the consequences could include being convicted in Federal Court, and a couple times overnight he had woken up in a panic that the FBI would be banging on his hotel door. He had been sure that he would not be able to hold firm if Heather challenged him.

But she had caved, and from the wetness of her pussy he had reason to believe that at least part of her was enjoying this. That was going to be the trick in all of this. Be strong enough to convince her that he was the real deal, but not so hard that she would consider calling his bluff. He had been scared shitless a couple of times during their chat that he had blown it, that she was going to pull the plug, but somehow he had pulled it off. By the time he had her spanking her titties (a particular fetish of his) he knew he had her. Going through her wardrobe had been extra fun. He smiled at the thought of her almost never wearing underwear from now on, and the gradual increase in exposure he could orchestrate for her, building up the levels of embarrassment. Heather was still on his screen, moving back out to her living room, wearing only the pink T and the boy shorts. He smiled as he noticed her idly playing with her nipples and rubbing her crotch. Clearly she was more turned on than she wanted to admit.

He had a lot to do to take her to the next steps. The new wardrobe and the selfies would keep her on edge for a few days, but soon he would need to take her deeper. He had ideas, but they would take preparations. And there was one thing that he could really only do while he was travelling, so he checked the recording software to be sure it would continue to record Heather, and he prepared to head out. He locked his screen in case a cleaning lady came in -- it wouldn't do for the hotel housekeeper to find out he was blackmailing innocent girls. Once he was sure his room was tidied up and left no incriminating evidence, he headed out.

*

Heather was sitting at her sofa, one hand inside her panties pumping two fingers in and out of her pussy, the other holding her shirt up and pinching an exposed nipple, when she heard one of her roommates at the front door. She was barely able to pull her hand out of her shorts and the shirt down before Keely came into the living room. Her heart was pounding and no matter how hard she tried to act normal she was sure she looked guilty as fuck. Her voice actually cracked as she tried to say hi. 

Thankfully, Keely didn't really look at her, and went into a rant about how much her job sucked. Heather did her best to listen sympathetically, although it was tough to listen to someone who had a full time job with benefits complain. Not that Keely had it perfect, working as a cashier at a car dealer, but at least it was a steady job. 

"... and then Joel, that creep, all he ever does stare at my tits while he talks to me, and now he's pestering me all day to get a drink after work. Holy fuck, you think a guy could take a hint. And maybe a shower every now and again. It amazes me he can ever sell car. Can you..." Keely's voice trailed off, her tirade grinding to a halt as she looked at Heather in her T and panties, legs spread wide. If Heather hadn't been so terrified, she would have appreciated the irony of Keely staring at Heather's tits right after deriding Joel for staring at her own.

"You look comfy," Keely said with a smirk once she had recovered.

"Oh," Heather felt she was failing miserably at acting normally, but she tried her best to deliver the line she'd been practicing since she had finished with SpareRod. "I was figuring that it's almost always just us girls around here, so I thought I'd dress like I really want to." 

She stared at the floor, feeling her cheeks burn. The whole thing was so humiliating, and to make it worse, it felt like her nipples were getting harder and poking out even more.

"So THAT's the way you'd really like to dress," Keely gave a wry smile. "I guess I've seen you in less, so wear whatever you want. Just don't be trying to steal all the cute guys coming through here."

Heather rolled her eyes. Like it was likely that she could steal any guys from Keely. Keely one of those girls that caused guys heads to snap whenever she entered the room. She was probably over 5' 10" with an athletic build while still quite curvy. In most ways, she was essentially the complete opposite from Heather, not just in her build, but also because she was outgoing and bubbly where Heather was more quiet and introspective. Consequently Keely was way more popular with the boys than Heather or even Anna. It was going to take more than skimpy clothes to attract boys away from Keely. 

Keely plopped down in a chair, and kept ranting about her day at work. Not too much latter Anna came home, and started ranting about her work at the pot dispensary. They were quite the trio, all college educated, bright young women with fantastic futures in front of them, all totally unsatisfied with their lives, both in terms of money and their love-lives. At least it gave them plenty to talk about. Which was a good thing, because it kept them from talking about the fact that Heather was barely wearing anything.

Heather offered to heat up some soup she had made over the weekend, so they could eat dinner together. Bringing her computer to the kitchen allowed her to flash her boobs and crotch to the camera for a bit and finger herself to make sure SpareRod would know she was trying to comply. The meal was very strange, with Heather getting more and more turned on sitting in her skimpy clothes while her roommates were still dressed from work. Keely and Anna teased her a bit that she was going to become a nudist, and Heather did nothing to protest that she wouldn't. There was no telling what SpareRod would make her do, plus the truth was the longer this this went the hornier it was making her. She even started having fantasies of SpareRod forcing her to do this completely naked, and the thought made her shiver. She kept hoping that the leopard skin pattern on her panties would hide that her pussy was soaking wet.

After dinner they all ended up watching some TV together after dinner, with Heather acting like she was working on emails just to make it look as natural as possible to have her computer on her all the time. It meant she couldn't flash him, but she did tweak her nipples through the shirt when she could, and she felt she was following his demands as well as possible. As soon as it was 10:00, she raced to her room, brushed her teeth, and then turned off her life before stripping down and getting in bed. She figured she had to do what he said, but there was no way she was going to hang out naked in her room with her door open while her roommates were home. Better to have them only wonder why her door was open when she was sleeping, than to have them wonder why she was sitting there naked.

It took her several hours to get to sleep. Part of her was stressing out with anxiety and worry about what SpareRod would make her do. But another part of her was turned on and couldn't wait to see how far he might be able to push her. The feeling she had, doing these crazy things that turned her on, but doing them essentially against her will, in a way that was not her fault, it was exhilarating. It was crazy, he could ruin her with the click of a mouse, but her soaking pussy made it undeniable that a part of her relished this. It seemed like there was no other way but to hope that he enjoyed the games so much that he would never do anything to jeopardize them. She just had to trust him.



The Perils of Being Too Trusting Ch. 03



So, I'm honestly ashamed how long this chapter took to write. Some of it was I got distracted, some of it was that I hate proofreading, so I just kept writing instead of going back to proofread. Very bad habit.

There are two more chapters after this one, and I am already working on them. Hopefully I can get back to posting faster than one chapter per year. If anyone is interested in proofreading, please, please, please let me know. I'm doing this in Google Docs, and it's pretty easy to give folks editing rights. If you like the story, at least it would get you an advance peek. 

Also any encouraging feedback always helps.

K

*

Heather was glad the restaurant was busy this morning, it made it easier to keep her mind off her complete lack of underwear. Her skirt came down almost to her knees, and her blouse and camisole covered things fairly well as long as she was standing straight, but she still felt very exposed. Every time she rushed back to the kitchen she could feel the draft around her pussy. It hadn't been obvious when SpareRod had picked out her outfit how revealing her top would be every time she bent over. With several buttons cut off the blouse, it fell open and exposed the camisole almost completely. While the cami was tight enough that there was no risk of her boobs falling out, it was a little low cut so it didn't cover them as well as Heather would have liked. Plus it did nothing to hide her nipples poking through the fabric. She'd only been at work for about 20 minutes, but she had received several appreciative stares from guys as she bent over to set down plates. 

The other thing she was avoiding was thinking about how the hell she was going to get the selfies taken. She checked the time on her phone, and knew she really couldn't put this off any longer. After topping all the coffee mugs she headed back towards the restrooms. She would have much preferred to do this in a stall in the women's room, but he had specifically forbid that. So she went right past the bathrooms and out the back door. She quickly scooted between a dumpster and the building corner, hiding herself for the most part from the back door and from the alley. It was still very exposed, but at least she should hear someone coming either out the door or driving up the alley. Once her phone was ready, she pushed down the cami so both her breasts were out, opened her blouse to completely expose them, and held up her skirt in the front so she was showing everything. She tried to take photo quickly, but the enormity of what she was doing hit her as she attempted to hold the phone up and capture her exposed tits and pussy. Her hands trembled and it took several tries before she had a clear picture. She decided to take one as an upskirt by holding the phone low, giving a close up of her pussy. She was amazed how swollen and open her pussy lips looked, and she couldn't resist running her finger over her clit as she snapped another picture or two. It felt so good, it was difficult to stop and cover up, but she knew if she stayed too long she was sure to get caught. She rushed to one of the stalls in the women's room so she could send the pictures to him in relative safety. She also took the opportunity to finger herself for a bit while she was there. She hoped that she wasn't so wet her juices would start running down her legs.

It wasn't until she was washing her hands that she noticed that pushing down her camisole had stretched it a bit, and it didn't want to stay as high as it had before. Bending over her reflection was showing a scandalous amount of boob down her blouse. She would have to be careful how she bent over. 

Three more times over her shift she snuck out to the back to take some more pictures. She felt like she had to vary it a bit, so she got some of her squatting with her legs wide, and even a couple of her ass as well. Even though it scared the shit out of her, it also was strangely liberating to be so wild, so sexual. In a strange way it helped to know that she was still a good girl and that she was only doing this because she was being forced. 

She wasn't being forced to masturbate in the women's stalls, but she was doing that anyways, and after the second group of photos she shot a short video of her finger-fucking herself and sent that too. She figured it might help keep him in a good mood and make him nicer to her. It shocked her how difficult it was to stop though, and she found herself chewing on her lower lip as she went back to work she was so frustrated. 

It wasn't until the third time behind the dumpster that she got caught. She was squatting down, the cami pushed down, the shirt fully open to show off her tits, her legs spread wide so she could finger her wet pussy, and trying to take the picture when she heard a voice.

"Wha da FUUUCK!??!" 

The homeless guy had been walking up the alley, and she hadn't heard him coming. She snapped her thighs together, tried to pull up her camisole, and rushed into the restaurant. She heard the homeless guy yell for her to come back a couple times, but thankfully he shut up and moved on. Her heart was racing as she tried to rearrange her clothes as best she could with trembling hands. She didn't even dare go into the bathroom, so she rushed to send off one photo to SpareRod and got back to work. It wasn't until she set down a coffee mug in front of a customer and saw his eyes widen that she realized maybe her clothes weren't right. She looked down to find that she had not pulled up her cami far enough, and her nipple had slipped into plain view. She tried to fix it and be more careful, but she was sure several more customers got a nice peek at her tits that morning.

Heather was a complete wreck by the time her shift ended. She could feel the slickness on her thighs as she walked, and she was worried that it might run down her legs where customers might see. As soon as she clocked out, she raced to her car to get some privacy. After wiping her upper thighs and crotch with some tissues, she checked her phone and saw she had an email from SpareRod:

subslut

While I can tell you are trying, you need to know your performance has not been satisfactory. You spent several minutes in your room last night before you got naked. You also failed to stay naked this morning until you were ready to leave your room. Although the quality of your pictures were quite good during work today, you went more than 90 minutes between them on several occasions. These transgressions will need to be punished. Take your camisole off from under your blouse immediately. Go to a grocery store to do some shopping. Send me a picture of yourself inside the store, proving you've followed instructions, and I will send you a shopping list.

SpareRod

"Fuck!" Heather swore. 

She thought she had been so good. She was dismayed to think what punishment might entail. He had made it clear that it would be more severe than yesterday, and she wasn't sure she could take it. But there was no way she wanted that video to go public either, so she decided to go to the store and see what came next. She tried for at least a minute to get the shoulder straps of the cami down her blouse sleeves so she could get the camisole off without taking off her blouse, but the sleeves were too tight. She finally gave up, and pulled the whole thing off as quickly as she could. Unfortunately that tangled her blouse, and she ended up spending even more time sitting topless trying to straighten out her blouse to get it back on. Finally, she started to pull it back on and almost shrieked when she noticed there was a guy less than 30 feet away staring at her in shock. She had no idea how long he had been there, but he had certainly had a clear view of her bare breasts. She didn't even button the blouse, she just started her car and raced away. 

She did manage to button her blouse at the first stoplight, but since she had cut off all but three buttons, it really didn't help. She was horrified by how much of her chest was showing. Just trying to make the shirt stay still while driving proved impossible. She had no doubt that she flashed several people as she drove to a supermarket. She did opt to drive across town to minimize the chance of running into anyone she knew. 

Once in the store, it took a while for her to find a quiet aisle where she could snap a picture safely. She knew enough about what he expected to make sure her nipples were completely exposed for the picture. No reason to disappoint him and draw more punishment. Unfortunately that made getting the picture even more difficult. Not the exposing herself part, that happened pretty much all by itself, since when she held the camera at arm's length to take the picture, the blouse fell open all by itself. But finding a spot where she thought she could do that without being spotted by anyone or by the security cameras she could see on the ceiling was a real challenge. She finally ended up in the greeting card aisle, facing the shelves as close as she could to try and hide from the security cameras. As luck would have it, right as she took the picture, an elderly woman came into the aisle. Heather covered herself as fast as she could, and hurried away to another aisle. She did hear the woman say something, but her ears were ringing and her heart was pounding, so she had no idea what the woman was saying or if it was even about her.

She sent the picture to SpareRod and tried to stay inconspicuous while she wandered around the store. It seemed to take forever, but it was actually less than ten minutes later when his instructions came.

Subslut,

Here is your shopping list. You need two zucchini or yellow squash, one a comfortable size to fuck yourself with, the other to feel a bit large. The other items should be all together in the store, an enema kit, some KY jelly, and two packages of condoms. You are not allowed to buy anything else, part of the punishment is everyone will be thinking about what you are up to. Make sure to take a picture of your items for me right before you check out. Then head home and I'll see you when you're on video.

S

Heather was terrified at where this was leading, but she couldn't see a way out. She grabbed a small basket, and headed to the produce section. She was in a bit of a quandary about what to do about the zucchini. Since she was so petite she was not one of those girls looking for a guy to be huge. In fact guys who were big enough to make her be careful was more the norm. That said, she knew if she picked them too small that he would accuse her going too easy on herself. In the end she picked one just over five inches for the small one, and another that was about six and a half inches long for the second. She just had to hope it would be okay.

Holding the basket so it kept her blouse closed, she headed towards feminine products for the rest of her purchases. She found the lube and the condoms quickly, but it took quite a bit of time looking between the oils, douches, and suppositories to finally find the enema kit. That in itself was a bit embarrassing to be spending so long looking in this area, but it got worse when she found it on the bottom shelf. She started to bend over to set the basket on the ground, but her blouse spread wide open, showing a dramatic amount of cleavage. If she bent at the waist, her blouse would open, but if she squatted down her skirt would ride up and she worried she would flash her crotch. To make things worse, a couple guys were hanging out in the aisle, watching her out of the corners of their eyes. They clearly knew something was up.

Using one arm to hold her blouse closed, and the other to keep her skirt firmly against her legs, she squatted down with her thighs pressed tightly together. She was sure it looked awkward as hell, but with the two guys staring at her blatantly, she figured it was less awkward than flashing them. Once she was down so her calves were touching the backs of her thighs, that freed one hand to reach for the enema kit. Her heart was pounding because of the guys watching her, and it was more difficult to stay balanced than she thought it would be. As she leaned over to get the enema kit from the bottom shelf, she felt herself losing her balance. On instinct she shot one leg out as a counter-balance, and used the hand that had been holding her blouse closed to steady herself against the shelf.

"Holy shit!" she heard one of the guys swear. 

Heather gasped and looked at herself. The blouse had not opened completely, but her left nipple was within millimeters of being exposed. On top of that, with her with her leg out and skirt riding up she was showing way more leg than she meant to, and it was possible the guys could see right up her skirt. She tossed the enema kit in her basket and bolted upright as fast as she could. She was so flustered that she was pretty sure that both guys got a decent look down her blouse as she rushed out of the aisle. As she walked away she thought she heard one of them say something to the other that included the word "tits," but she didn't stick around to find out. 

Her shopping complete, she headed up front to pay and get out of there. Checking out with her current purchases, dressed in this outfit, the whole idea put a pit in her stomach. The humiliation of interacting with the clerk would be unbearable. While she stood there, too terrified to move, she suddenly remembered that she needed to take a picture of her basket. While using her phone to snap the picture, it occurred to her that this store had self-check-out. She almost jumped for joy with her plan to beat him! He hadn't told her that she needed to check-out with a cashier, so she could do it herself, and not interact with anyone. 

Unable to keep the grin from her face, she headed to the kiosks, and scanned everything in her basket. She worked quickly to get it all into a bag, glad that there was no one in front of her to peek down her blouse. It gave her the freedom to work faster without worrying about holding her blouse together. She got her credit card out, started to pay the bill, and saw something that almost made her scream in horror. There was a screen above the kiosk that she had not noticed before, and a video of her was on that screen for the world to see. Even worse, it was from an angle that was clearly looking down her blouse. The way she was leaning forward, people walking by could see on the screen that her right nipple peeking out . To top it off, the word "RECORDING" was blinking across the bottom of the screen. Heather was mortified. Not only had people walking by seen her exposed breasts, but the system was now capturing it, probably for eternity. She looked over her shoulders, and noticed a couple guys had positioned themselves to watch her on the screen. There really wasn't anything to do but cover up and leave as fast as she could.

The drive home was every bit as nerve wracking as the drive to the store had been. Her blouse just did not want to stay closed. She had no idea how many people might have seen her tits on the way home; she tried not to make eye contact. Once safely in her house, she went to her room and turned on her computer. At the last second she remembered she was supposed to be naked. She had just finished pulling off the skirt and blouse when his voice came over the speakers.

"Hey slut," he asked, "aren't you supposed to get naked as soon as you enter the house?"

"Yes Sir, sorry Sir," she apologized quickly.

"That will add to your punishment. You're certainly racking it up today. But we'll deal with the extra punishment in a bit, let's get started on what you need to do to make up for last night and this morning. Show me your pussy, is it wet?"

Heather was humiliated all over again to show him how slick and swollen her pussy lips were. It was bad enough to stand in front of her computer with her hips thrust forward to push her sex close to the camera, but to have it be so obvious that it was turning her on made it doubly degrading. She could feel herself blush from head to toe listening to him talk about how wet her hot little cunt was. She was glad when he told her that she could step back, but her stomach resumed its somersaults when he told her she needed to get the zucchinis and condoms and go to her living room window.

"Puh-please Suh-Sir," Heather stammered, "I... I don't want to do this."

"You should have thought about that before you disobeyed the rules, now get your ass out there."

Heather had to hold back tears as she set the computer on the floor next to the window, and stood with her hands on the window sash and her legs spread wide. This was way worse than yesterday, not because she was any more exposed than yesterday, but she knew what was coming next.

"Okay, now put a condom on the smaller zucchini, and let's see how it fits."

Heather was so terrified she was shaking. She knew what he was going to make her do, and the idea that her neighbors might be able to watch was inconceivable. It was one thing if they saw her masturbate with her fingers, but this was too much.

"Please Sir, I can't do this. Please don't, I just can't, it's too humiliating. With a zucchini?!?"

"Too humiliating? More than having that video be out on the web where anyone could find it? Okay, I'll admit that fucking yourself with some vegetables is humiliating by itself, and that doing it in front of your window is doubly so. But compared to having that video out on the web for anyone to find? With everything you did? With everything you said? About people you know? Come on, it's likely that no one will even see you, and even if they can, they probably won't even be sure if it's you or what you're really doing. Now I know your cunt is plenty wet, so get that condom on it, and start fucking yourself."

Heather thought about just shutting down the computer and running away, rather than continue this degradation. But she knew that would be even worse. She looked up and down the street, and decided there was probably never going to be a better time. She opened the condom package, rolled it onto the phallic vegetable, and slowly worked it in to her pussy. It wasn't very big, and she was so wet that it slid in easily. And Holy Fuck did it feel good! She hadn't had anything bigger than her fingers inside in so long, and just the feeling of it sliding in caused a moan to escape her lips. She was more humiliated than ever to have him know how much this turned her on.

He kept her going at in front of the window for over fifteen minutes, switching to the larger zucchini about halfway through. She was sweaty and trembling from standing with her knees flexed and gyrating her hips as she fucked herself right there where anyone walking by could see her. Her nipple was sore from pinching and pulling on it, and her pussy was buzzing from all the attention it was getting. The whole experience had been excruciatingly degrading. The worst part was that just when she had been right at the edge of orgasm, right as she could feel the beginnings of a climax washing over her, he had told her to stop. The frustration almost made her cry. 

"Okay, we should take a break from that," he chuckled, "you little slut, you're getting all hot and bothered. Besides, we need to do something about your clothes for tomorrow. I think you have a pink camisole and another white blouse right?"

"Yes Sir."

"Good, wear that, but that skirt was too long. I think you have a black one that is a little shorter, right? But I still don't think that's short enough. I think you can hem that up two more inches, okay?"

Heather couldn't believe it, he was going to have her spend the next couple hours naked at her sewing machine hemming up not just her black skirt, but also another grey one to be mid-thigh. They still wouldn't be her shortest skirts, but they would be the shortest ones she'd ever worn to work, and without panties they would feel very risky. She kept hoping for reprieve before tomorrow, but she agreed to work on the skirts.




The Perils of Being Too Trusting Ch. 03



He also left her instructions to spank herself again, twenty times on each cheek, and five times on each tit. He told her that he wouldn't watch it live, but he would watch the recording to make sure she did a good job. Heather didn't know how she felt about him not even staying to watch her do it. It's not like she liked him commenting on how she spanked herself, how her ass reddened or her breasts jiggled under the impact. But the fact that he wouldn't even watch seemed more demeaning, like she wasn't worth it. It was crazy that she was wishing that he'd watch her spank herself, but somehow doing it without him watching was even worse.

His final reminder was that while she was allowed to put on a bra, the camisole, and panties for the babysitting job, she must not put them on until she was in front of the family's house. He made it clear he expected pictures of her dressing in her car. With that he was gone.

The spanking seemed even more painful than the day before. Without him to guide her, she kept feeling like she wasn't hitting herself hard enough to satisfy him. In the end she gave herself close to 30 spanks on each ass cheek, and over ten on each tit because it was so difficult to actually hit herself there, especially the nipple. Once she finally finished, she set the sewing machine up at the dining room table and went to work. She had no idea how she would explain it to her roommates if they came home, so she just hoped they stayed at work all day and didn't stop by the house for some strange reason. 

She breathed a sigh of relief after she finished the skirts, and dressed to drive to her babysitting job. Again, she was not entirely successful in keeping her boobs covered while driving. The way the seatbelt pressed against the blouse had a tendency to hold it open exposing her to anyone looking in. She couldn't be sure if anyone saw her, but it was embarrassing all the same. She parked in front of the family's house, took several pictures of herself with her blouse open and her skirt pulled up, sending them to him to prove she had not put on any underwear . Putting on the bra and camisole under the shirt without exposing herself too much proved to be harder than she expected, but she managed eventually. After putting on her panties, she headed into the house to watch the children.

The afternoon and evening was welcome relief from her world of being blackmailed. Being fully dressed for the first time in 24 hours, and being too busy to think about her predicament was a blessing. All too soon, it was 9:30PM and she was back in her car checking her phone as she pulled off her panties. She knew this respite was too good to last, and she wasn't surprised to see a message. She was surprised how extreme it was, demanding that she find a quiet place to stop her car, and to take a picture of herself outside her car and completely naked. Just the thought of it was terrifying, especially since he made it clear that she needed to use her flash, which would almost certainly attract attention no matter where she did it. In the end she found a parking lot for a massive big box store that had closed, and pulled to the edge of the lot. She stripped naked in the car, hunching over to hide from any cars that might happen by. She quickly jumped out, crouching to keep the car between her and the rest of the lot. Squatting with her legs spread wide, knowing that he'd appreciate the clear view of her crotch, she snapped a quick picture. The flash from her phone was so bright it scared the crap out her, but she knew she'd better take another one since she really couldn't see where she was pointing, and she didn't want to waste time looking at it while she was completely exposed. 

Back in her car, she breathed a sigh of relief that the first picture was just fine. Once she had pulled her blouse back over her shoulders she sent him the picture along with the message confirming she would follow instructions to not put on her skirt or button her blouse until she got home. The drive was beyond terrifying. All she could think about was if she got pulled over she would not have time to get dressed. She was so nervous that she was probably running the risk of being cited for driving too slow. Even still, she couldn't stop herself from teasing her clit and pinching her nipples from time to time as she drove. She hated the fact that she was being forced to do this, and it felt completely different than she had fantasized about. She couldn't deny she was turned on now, but she was pretty sure that getting arrested for public indecency would not be a turn on. The fear she felt was very real, and it made her heart race. She parked in front her house, thanked God for getting home safe, and pulled on her skirt to go into the house. 

She felt so much better being covered, that it wasn't until she saw Keely's face staring at her that she realized how exposed she still was. Her blouse only buttoned to about halfway between her navel and her breasts, and it fit quite loose, so there was real risk of her boobs popping out as she walked. It took a lot of will to not cover herself with her arms, but she followed instructions and stood straight with her arms at her side. She knew she'd be on video soon enough, so there was no point in defying him.

"Holy fuck!" Keely exclaimed. "Did you wear that to babysit?"

"Fuck no," Heather was stuck how to explain why she had taken off her clothes on the way home, so she had to scramble. "I was thinking about how you and Anna were saying I should be a nudist, so I was feeling a little crazy and I drove home naked." Heather was even more shocked at the words coming out of her mouth than Keely was, but it was the best she could do.

"So I just put this on when I got here," she finished lamely.

"You're shitting me!" Keely was still trying to take it in. "Really? You drove home naked? What possessed you to do that? That's crazy. Too bad Anna's not here, she'd laugh her ass off. I know you like skinny dipping, but I didn't think you were really a nudist." 

Heather just shrugged, got her computer, and sat down in the chair across from the sofa where Keely was sitting. She opened the chat program and began broadcasting from her camera, hoping that Keely would change the topic before he would be able to hear it all. Those were quickly dashed.

"No," Keely continued, "you didn't really drive naked did you? You're crazy. Weren't you scared shitless?"

"Totally shitless," Heather confirmed, "but kinda exciting too. It was weird. My heart was pounding and I was literally shaking, but I never even thought about stopping." 

"Better you than me, girlfriend."

By this time Heather had the video chat running, muting her speakers in case he came on. It only took him a couple seconds to realize she couldn't hear him and to start the chat screen. His first question was to ask what was going on, and she was mortified to explain to him that she was trying to convince her roommate that she wanted to become a nudist. He urged her to continue the conversation.

"Oh you know how I am," Heather tried to keep it going, "I like the thrill. It's been kinda boring since we graduated, I'm just looking to make things a bit more exciting."

"You just need to get laid, that's what you need."

"No shit on that one, but pickings are pretty slim around here lately. So I have to adapt."

"Oh, that's what you're doing, ad-daaaapting," Keely rolled her eyes. "I'm not sure running around in your undies or driving naked is what I'd call adapting, but whatever suits you. Like I said last night, just don't be trying to steal all the guys on me."

The text on Heather's screen urged to push the issue.

"So," she stammered, "you're saying wouldn't mind if I were naked right now, as long as there were no guys around?"

"Shit, you know I don't mind. I'm the one who went skinny dipping with you. But there's no way you're getting naked right there with the front blinds open."

Heather knew even before she looked at her screen that she was going to be required to prove Keely wrong. Sure enough the instant message from him said she should strip to show Keely the new Heather. Heather rolled her eyes at the idea that this would be the "New Heather", but she knew what she had to do.

"Ha," she forced a chuckle, "is that a challenge? You know howI respond to challenges."

Before Keely could say anything, Heather stood up and unbuttoned the last buttons on her shirt. Her hands were trembling, not really because of the thought of being naked in front of Keely; that had happened before. It was more the reason she was stripping, knowing she didn't have a choice, not knowing what might come next. What other ways would he humiliate her? What would it do to her relationship with Keely? But she tried hard not to think about all that, and just stripped off the blouse and stepped out of the skirt.

"Holy fuck," Keely was never speechless for long, but she did take a long look up and down Heather's naked body before she started talking. "Well, suit yourself. But just because I went skinny dipping with you that one time, don't expect me to join your little nudist colony here. And I'm not sure you should do it in front of Anna either. I think hanging out in your undies was pushing her limits yesterday. You start going around full nakey and she'd probably freak the fuck out."

Heather's heart was pounding so hard she could barely hear Keely through the buzzing in her ears, and she had to sit back down before she fell over. She kept thinking how crazy it was what she was doing, that normal people didn't do stuff like this. Being continuously aroused wasn't helping anything either. Her nipples ached, and she was desperate to tweak or tug them, although it terrified her that she might start doing it subconsciously while Keely was watching her. Fortunately she was able to put her laptop strategically over her crotch to hide that her lips were swollen and wet. At least she was able to do that until SpareRod noticed.

SpareRod2003: u need to move ur laptop - no fair hiding ur cunt

nawtysubslut1989: Pleeeze Sir. Don't make me do too much - it would be worse than just letting her see that video

SpareRod2003: relax slut. I'm not going to make you beg for her to piss in your mouth or anything. I just figure that if you're going to be naked around her all the time you should make sure she can see you well

nawtysubslut1989: Naked all the time?!?!???

SpareRod2003: Lol. Well, maybe not all the time. It sounds like Anna wouldn't appreciate that. Will she be home soon?

nawtysubslut1989: Not for a few hours, she's out with friends.

SpareRod2003: Then no reason for u to not show off some. Now move that laptop and spread ur legs a bit so she gets a view of your lips.

Heather couldn't believe she was doing this, moving the computer up to the arm of the chair and spreading her legs to give Keely a full view. She had never felt so exposed in her life. She couldn't bear to make eye contact with Keely, she could see in her peripheral vision that her roommate was occasionally looking over and staring. It felt so weird to be naked and to be ogled by her fully clothed roommate. The whole experience was turning her on so much that she began to get worried her pussy would start leaking right in front of Keely.

Nawtysubslut1989: Please Sir, may I go to the bathroom to get a towel and wipe myself? I'm afraid I'm going to leave a stain on the chair.

SpareRod2003: I might let you do that slut. But I need for you to do something for me. Do you have any beers in the house?

Ns19: Yes Sir, I have a six-pack of Fat Tire that I bought a few days ago.

SpareRod2003: Great. In a minute you're going to ask Keely if you can get her a beer. Try to make sure she says yes, but either way you can go to the bathroom then. Leave your computer, it would be weird to take it with you. You may grab a towel to put on the chair. Go get the beers, and once they're open, use one to fuck yourself in your kitchen. I want you to fuck yourself hard for two straight minutes. I want your cunt swollen and gaping when you sit back down. 

Ns19: WTF! You're joking!?!? What if Keely sees?

SpareRod2003: Definitely not joking. Make sure Keely doesn't see. I'll be nice to u, u can keep that bottle for yourself. I'm not sure Keely's ready for the taste of ur pussy yet

Heather was terrified by the "yet" in that comment, but her mind was spinning too fast to even be able to think about what she might say.

SpareRod2003: You'll probably need to drink a bit first to keep it from foaming over, but you'll figure that out. When you're done, take the beer to Keely. Make sure you stand close to her with your legs spread when you hand over the beer. She should get a good view of your open, sopping cunt, and probably be able to smell it too. NOW GO GET GOING SLUT!

Heather didn't want to go. 

It was going to be too humiliating. Maybe it would be better if he just posted the video? She thought about how likely it was that anyone she knew would even see it. There was a lot of stuff on the internet, so maybe no one she knew would find out. And even if someone did, would they really tell Keely or the O'Donnell's? She tried to weigh the uncertain risk of someone seeing the video against the certain risk of fucking herself with a beer bottle in the kitchen. Then she saw something on her computer screen that changed her mind.

SpareRod sent her Keely's email address. 

Heather's stomach did flip-flops as she processed what she was seeing. He had obviously used his time on her Facebook account to collect contact information for her friends. That meant he had her roommates', the O'Donnel's, and even her parents' emails. He could send that video directly to the people that she was most worried about. Her trust in him had put her even more at his mercy, and all she could do now is go with it and hope it didn't get too bad. There was only one way forward.

She asked Keely if she would like a beer.

Heather had to work a little to convince Keely to not let Heather drink alone, but it was never too hard to convince Keely to celebrate a little. That settled, Heather managed to get to the bathroom. She used the opportunity to go pee, and grabbed a towel before heading to the kitchen. She got the beers, opened them, and as she drank about a third of a beer she thought about how to do this. First, she needed find a place in the kitchen that wasn't too visible to the neighbors. It was one thing to have them see her nude, she really wanted to avoid them watching her do something this perverted. She found if she stood in the corner near the microwave she was mostly out of view of the window, and even out of view of the hallway in case Keely decided to get up. The microwave gave her an idea on how to both explain two minutes of fucking herself with the bottle, and cover any noise she might make. She pulled out a package of popcorn, and set the microwave for two minutes.

What she hadn't counted on was that while the noise of the microwave would mean that Keely couldn't possibly hear that Heather was masturbating in the kitchen with a beer bottle, it also meant Heather wouldn't hear if Keely got up and came to the kitchen. Heather worked the beer bottle in and out of her pussy, gyrating her hips, and biting her lower lip to keep from moaning. She pushed hard on the bottle, getting the entire neck in as well as part of where the bottle flared out. She wanted to a good job for him, to make her pussy soaked and gaping. She didn't want to give him any excuses to make things any worse. 

Suddenly she heard some noise from the living room, and for a brief second she was terrified that Keely was headed towards the kitchen. She kept fucking herself, listening and looking for any clue that she was going to be found out. Thankfully there was nothing more, but to her surprise the fear of being caught pushed her right to the edge of orgasm. She actually had to stop and pull the bottle out for fear of cumming on the spot. Not only would that have broken his rules, but she would have screamed out so loud that Keely, the neighbors, and everyone on the block would have known what she was doing. After about ten seconds she went back to fucking herself, and counted herself lucky that she didn't orgasm before the microwave beeped and she could stop. Pulling the bottle out made her feel so empty and frustrated that she wanted to cry. She didn't even look at her crotch, knowing that seeing just how much she was about to show to Keely would make her cry for sure. 

She carried Keely's beer and the bowl of popcorn out, and stood close to her roommate to let her take the beer and some popcorn. Keely's eyes focused briefly on Heather's rock hard nipples, then went wide as she looked down at Heather's pussy. Heather's shame was beyond anything she could have imagined. She knew it must be totally obvious that her pussy looked freshly fucked, and to make it worse Keely just stared at it instead of taking the beer she was being offered, her lips slightly parted. It may have been Heather's imagination, but she thought Keely was about to lick her lips in anticipation.

"Uhhm...thanks," Keely finally spoke, "it's kind of wild having my own naked serving girl. It seems very sophisticated in a debauched kind of way." 

"Well that's what I'm going for," Heather giggled, "sophisticated debauchery." 

She couldn't believe she had said that, but there was no taking it back now. She went back to the kitchen to get her towel and beer. Keely gave a funny look as Heather spread her towel on the chair and sat down. Spreading her thighs to expose her pussy again was even harder than she expected. She could easily see her clit and her inner lips protruding as she sat, and she didn't even want to contemplate how it must have looked to Keely. Keely stared at Heather's crotch, but thankfully only talked about the towel.

"That's a good idea if you're going to be a nudist," Keely suggested, "I hear nudists keep towels with them at all times."

Heather laughed, and the two them chatted about more normal things as they drank their beers. Even so, Heather's state of arousal stayed on red alert, with both Keely openly staring, and the reminder Heather got with every sip of her beer. She couldn't actually taste herself on the bottle, but there was no denying the smell of sex each time she brought to her mouth. 

Even after the conversation moved away from Heather's nudity Keely would still occasionally make a crack about having a naked serving girl. SpareRod kept up the chat at the same time, urging Heather to play up the role, as well as making her continue to humiliate herself. Periodically he'd have her do things like lifting her foot onto the chair to spread herself wider, idly tweaking her nipple, or sucking on her beer bottle suggestively. Heather was pretty sure her sexual behavior was noticed, but Keely didn't say anything. 

After a bit, SpareRod upped the ante. He told her to offer to get Keely another beer, but not get one for herself. He thought that would better fit her role as a serving girl. On top of that, once she brought the beer, she had to offer Keely a foot massage. He made it clear that she was to persist until Keely agreed, or Heather would face more punishment. The image of kneeling naked in front of Keely and rubbing her feet was incredibly erotic to Heather, and she could feel her pussy pulsing as she typed about it. Unfortunately actually suggesting it to Keely, while standing naked in front of her, was so humiliating that her body rebelled and she found it almost impossible to stand. SpareRod was persistent though, and he made clear he was not going to let her escape. He also insisted she turn her laptop so he could watch the whole experience and be sure she didn't cheat. Realizing she was beaten, Heather dove in to her tasks.




The Perils of Being Too Trusting Ch. 03



Keely easily agreed to another beer, but said this had to be her last one since they both had to work the next day. Heather padded naked into the kitchen to fetch the beer. The only relief from her terror about what was coming next was that she didn't have to fuck herself on the bottle again. She brought the beer back to Keely, which elicited a puzzled look.

"Aren't you going to have another one?" Keely asked.

"No," Heather felt like such a dork, "I figured if I'm going to be your serving girl, I should play the part."

"Really?" Keely came back after an awkward pause while she looked up and down at her naked roommate. "Hmmm, I think I'm gonna enjoy this."

"Yeah," Heather tried to smile to cover how nervous she felt. "Well I guess if I'm in the role, I should go all the way. Anything else I can do for you? Maybe a foot massage?"

"Yeah right!" Keely retorted sarcastically. 

"C'mon. You know you like massages."

Wait, you're serious? You want to give me a foot massage now? Like that?"

"I'm just trying out the serving girl role. Indulge me. Besides your feet must be a little sore from being in heels all day "

"Well, fuck," Keely laughed, "it sounds more like you're indulging me, not the other way around. But who am I to argue? Girl... oh serving girl! Massage my feet for me now!"

Heather had to laugh at Keely's mock imperious mannerism. Keely put on a haughty look, kicked off her heels, and stuck her foot out for Heather to massage. Heather's heart skipped a beat and she gulped as she got down on her knees in front of Keely, resting her roommate's foot on top of her thigh and massaging it. Keely sighed loudly, took a sip of her beer, and rolled her head back on the sofa. Heather smiled watching Keely luxuriate in being served, and tried to focus on doing as good a job as she could. She felt so horny she could barely stand it. At one point she had this crazy urge to pull Keely's foot into her crotch and hump herself on it. She knew better than to try, but it was exciting to think about.

A few times while working on Keely's foot, massaging the arch, Heather's bare breast brushed against her roommate's foot. When she switched to the other foot, Keely's toe brushed against Heather's nipple, tweaking it slightly. A shiver ran through her body, and she thought she could see a slight smirk flash across Keely's face. After that, every time Heather's boob came in contact with Keely's toes, Keely would wiggle her toes, almost like she was trying to hit Heather's nipple again. Heather wondered if it were a game, trying to get her to jump. She felt her face flush as she wondered how much Keely was enjoying this.

Heather switched to one of her favorite techniques for foot massage, using her arm to trap the heel against her hip and stomach, and pulling on the toes to stretch out the foot. That put the toes very near her right nipple as she pulled, and Heather enjoyed the sensation as Keely's foot bumped her boob. Keely clearly enjoyed the sensation of having her toes pulled, letting out an audible moan as Heather pulled. Heather was so turned on she could barely stop from jumping Keely's bones, damned the consequences. 

But it was not to be. Keely sat up abruptly and pulled her foot back. She was flushed and breathing a little hard, and Heather suspected the situation had gotten to Keely as well. 

"Very nice foot-rub serving girl," Keely said using her mock imperious tone again. "Now I'm off to bed, it's an early morning tomorrow. You'll clean up here, won't you?"

Keely stood, and actually patted Heather on the head before heading off to her bedroom. Heather felt so humiliated. Not only had she been getting ready to make a pass at Keely, and now felt rejected, Keely was seriously treating her like a serving girl by telling her to pick up and patting her on the head like some kind of pet. Unfortunately the humiliation only added to her horniness, and she was now desperate to cum. She jumped back on the computer as soon as Keely's door was closed.

SpareRod2003: Well done slut. I wish I could have seen more of what you were doing to her feet, but watching her face was amusing. It looks like she enjoyed that very much.

NawtySubSlut1989: Thank you Sir. I wanted to do a go a good job.

SpareRod2003: Did you enjoy it?

NawtySubSlut1989: Fuck Sir, I'm so horny now!

SpareRod2003: Lol - I'll take that as a yes. We'll have to make sure you get plenty of chances to serve her on your knees from now on. Get things cleaned up like she told you and then go to your room. Be sure to bring your beer bottle, you're not done with it yet.

Heather washed the popcorn bowl, put it away and threw Keely's bottle in the recycling before racing to take her computer and her empty beer bottle to her room. Even though Keely's door was still shut it made her feel very exposed with her door wide open. All it would take would be Keely walking into the hall, or Anna coming home and she would be exposed. Since there wasn't anything she could do about it, she tried to put it out of her mind. 

His first command was for her to sit facing her wide open door, and resume fucking herself with the beer bottle. While she was a little grateful to be facing away from her window so that if the neighbor looked over it wouldn't be completely obvious what she was doing, but she did worry about the squishy noises as she worked the bottle in and out as deeply as she could. He let her go for almost five minutes, just as she was feeling an orgasm build up.

SpareRod2003: I have a few more tasks for you slut. Go to your bathroom now and use your enema kit on yourself. Be sure to follow instructions and flush yourself out well, do it at least two times. There will be severe punishments if any shit is visible when we are playing later. I'm not into that, I only want to play with your ass. There will come a time when you'll have to do this on camera, but for your first time, I'm really not interested. Keep your bathroom door open of course, but you can leave your computer here..

Whenever Heather thought her humiliation couldn't get any more unbearable, he somehow found a way to make it even worse. She had never had an enema, actually had never really even considered it. While it was a small relief that he wouldn't be watching her try to insert the nozzle up her butt, doing it with her doors open added more than enough terror and humiliation. What if Keely heard? What if Anna came home and walked into her room? She tried in vain to convince him to let her put it off or to close her doors, but he made it clear that he wouldn't budge. Reluctantly she headed to her bathroom. 

It took three tries before she was satisfied that she was flushing clear. Overall the process wasn't too unpleasant, the only bad part had been a few cramps while she was trying to hold it in. She had read a few stories where girls were forced to hold it in for extended periods, and she couldn't even imagine what would really be like. It certainly wouldn't be sexy, it was too uncomfortable to really be a turn on. 

The next layer of humiliation was to allow him to inspect her asshole. He had her stick her butt in the camera and spread her cheeks wide. This was followed by probing with her finger, first lubed only by spit, and then using the KY lube she'd bought. Soon she was laying on her back in bed, legs high in the air, working a well lubed beer bottle in and out of her ass while she flicked her clit with the other hand. When she got too close to cumming, he had her stop playing with clit, and squat with the bottle on the floor, using her weight to push the bottle deeper into her ass. After a couple tries she got the entire neck of the bottle in, but it was too uncomfortable to push it in any deeper so he made her just bounce there for a while until she could return to her previous position with her legs up and playing with her clit. She lost track of time going back and forth, going right up to the edge of orgasm followed by stretching her anus using her body weight against the bottle on the floor. 

When he finally let her stop it was almost midnight, and she was a wreck. She was hot, sweaty, her ass ached, and she was absolutely desperate to cum. She hated herself for it, but she was reduced to begging to be allowed to cum. 

NawtySubSlut1989: Pleeze Sir, may I cum? I'm so horny, may your horny sub slut please cum?

She knew enough from his stories to know he'd like her referring to herself in the third person, and she hoped it would be enough. Unfortunately he made it immensely clear that she was not to cum, and that he expected her to keep the camera on all night, and in fact all the way until she left for work. He warned her that he would send her an email before morning with additional instructions for the day, and with one last reminder that he would be watching her, he told her to go to bed.

*

Heather carefully set her computer by her bathroom sink while she waited for the shower to warm up. As weird as it had been yesterday to shower with her door open, it felt very strange to be arranging for it to be recorded. She knew that he didn't want the shower curtain to obstruct his view, which meant there would be lots of spray, and that could be bad for her computer. Satisfied it was positioned to stay dry, she climbed in the shower. He had sent an email overnight, giving her several new instructions, starting with what to do in the shower. Aside from getting clean, she was now required to masturbate for five minutes every morning while in the shower, and to make it even worse she was required to finger fuck her asshole the entire time she was doing it. He made it clear that she was not to cum, but he expected her to get very close. 

She used a little bit of conditioner to lube up her middle finger and her asshole, and gently slid it in. His instructions were to face away from the camera and bend over with her legs spread wide so he could clearly see her finger slide in and out as she diddled her clit. The position was a bit awkward, but the more turned on she got the less she thought about it. Actually she got so into it that she slid a second finger into her ass, and had to bite her lip to keep from moaning. She had to stop touching her clit for a bit after three minutes to make sure she wouldn't cum, but she was right back close to orgasm when the five minutes was up and she could stop altogether. 

The newly shortened skirt came to her mid thigh, and felt especially skimpy with nothing under it. The camisole and blouse set was similar to what she had worn the day before, only the blouse was a little bit thinner, and she could just see the bumps of her nipples even when she was fully covered. She was bound to get more stares today.

Friday mornings were always busy with regulars at the restaurant, and Heather felt rushed from the moment she got to work. She tried not to make eye contact too much with her customers, especially the men. She could sense their eyes wandering up and down her body, lingering on her thinly covered breasts or her bare legs. She could feel face warm as she blushed from being on display, and her nipples ached from being continuously hard. 

He had different instructions for sending him proof today, letting her use the ladies room instead of the alley. That was the good news, since she did not want to get caught by the busboys or by any homeless people today. But the bad news was he wanted her to send a couple short videos of herself every hour. One needed to be of her pinching and twisting her still sore nipples, and the other of her finger-fucking herself with two fingers. By the third time she had to sneak into the bathroom it was getting so embarrassing it was ridiculous. There was a customer in the stall next to her, and no matter how quiet she tried to be, she felt like the squishy noises from her fingers working in and out of her pussy was coming over a loudspeaker. 

She felt like her co-workers were looking at her and wondering what was up that she was going to the bathroom so often, and that her customers were staring at her ever more prominent nipples. The worst thing was when some of her juice actually leaked onto her thigh, and began creeping down as she walked. She was terrified that it would show below the hem of her skirt, but there was no way she could stop and wipe herself clean without attracting even more attention. She was completely mortified when some actually dropped on the floor, leaving a small glistening trail down her inner thigh. It was five more minutes before she could get enough privacy to wipe it with a napkin.

When she finally left work she was a jumble of nerves. Her nipples ached from all the twisting and pulling, and her pussy was leaking like a faucet under her short skirt. Even though she knew that she would be naked at home, and she was terrified at what he might make her do, she was just glad to be away from everyone ogling her. As soon as she got home she stripped down in her living room and turned on her computer, waiting for him to come on and give further instructions. She ended up kneeling naked in front of her computer with her hands on top of her head and legs spread wide for almost a half an hour before he came on. It was excruciating to wait like that, with nothing to do but worry that someone would come to the door, but she didn't dare do anything else. She was determined not to give him any reasons to punish her today. 

"Hello slut," his voice finally came out of her speakers, "I'm enjoying the videos you sent. Are you still as wet as you were at the restaurant?"

"Holy shit Sir," Heather complained, "I'm sure everyone knew what I was up to. I was in the bathroom so much, it was so hard to be quiet, and I'm sure I smell like sex."

"Show me."

Heather was reminded how humiliating it was to spread her lips and show how well lubricated her pussy was. She felt like she was blushing to her toes as she played with her pussy, spread her lips, pushed two fingers inside of herself to show him how much the lube coated her fingers, and other humiliating demonstrations. He made her smear her juices around her thighs, neck, and tits before he let her quit. 

"I've sent you a package," he finally changed the subject, "and it will need a signature, so we need to find something you can wear when you sign for it. Go find a bath towel we can modify to be more consistent with your new dress code."

"Package? What did you send me Sir?"

"Not your place to ask, slut. It's your job to prepare yourself for the delivery man."

"Please Sir, don't make me do something with him. I'm not really a slut Sir. I couldn't really do anything SIr, I'm just too scared."

"Oh stop your whining, you silly bimbo," he scolded her. "I won't push you any further than you're capable of, but we've talked about how you are going to have to get used to be naked in front of strangers. You won't have to touch him or let him touch you, but you are going to be a bit embarrassed. Now go get that towel."

She wasn't sure she trusted him, but she figured keeping him busy with the towel would at least distract him. She spent the next ten minutes cutting one of her large bath towels to be almost the size of a bath mat. She cut it so it was just barely long enough to wrap around her, with no option but to let her bare hip peek out the slit. Once she had it tenuously in place to cover her boobs, it came down just barely past her crotch. Even if she managed to keep it on when the package was delivered, the FedEx guy would be seeing a lot of skin. And SpareRod made it clear, that was not the way it was going to happen.

"Now practice by raising your left arm. Once you take your arm away from where you have it tucked in, I want the towel to fall."

It took Heather a couple tries to get the towel to cover most of her private parts but drop the instant she raised her left arm. He made it clear that she would be doing this in front of the delivery man, and made her practice several times to make sure the towel would drop every time. Once he was satisfied, he told her to get naked again, and to head to the bathroom. 

He let her know that he would expect her to give herself an enema every day when she got home from work, so that she would always be clean for any playing in the afternoon. She discovered it was even more humiliating to flush herself out with him watching as she did it. He made her put much more liquid up her ass, and then she had to hold it for five minutes or more while she played with her clit. The conflict between being right at the edge of orgasm and the pain and cramping from the enema shredded her equilibrium and left her feeling like she could focus on nothing other than her need to cum.

Unfortunately it was not to be. He made her take another shower to rinse off and get her hair wet so she'd have an excuse for only having a towel on. He didn't let her towel off, but made her walk around naked and dripping to grab one of her jeans skirts plus the shortest skirt she owned to take to the living room.

Her shortest skirt was a pleated floral print one that she liked to wear when she was getting a bit dressed up but keep a youthful look. It was definitely shorter than mid-thigh, but she had friends who wore shorter skirts. Unfortunately he wanted her to cut her jeans skirt to be an inch shorter than that. It took just few minutes to cut and model it for him. The skirt was now just thirteen inches from waist to hem, and while it covered everything, Heather knew she would have to be very careful in this skirt. Especially since it was unlikely he was going to let her wear one of her few pairs of panties. All she could do was hope she could stay standing up straight whenever he made her wear it.

But for now he made her take it right back off again, and sit nude in her living room, working the hem of her newly shortened skirt with a bristly hairbrush to try and fray it a little. He told her it was to make the cut denim look more used, but she suspected it was also to keep her mind occupied while she sat naked waiting for the doorbell to ring. Their conversation moved into slightly more normal territory while she worked the skirt, and although he occasionally made her twist and pull her nipples or tease her clit, it was otherwise like chatting with an ordinary friend. The whole thing seemed so surreal to Heather. She remembered how much she enjoyed chatting with him, and what had attracted her to him in the first place. It was difficult to reconcile that guy with the one who was about to parade her naked in front of some stranger.

Heather's heart started pounding when she noticed the delivery truck pull up in front of her house. She rushed to wrap the towel around her, and repositioned the camera to face the door before her doorbell rang. She was literally shaking as she undid the latch and opened the door. Time seem to slow down as she found herself face to face with a middle age guy in a FedEx uniform, who appeared to be in complete shock as he looked her up and down.

"I'm sorry, I just got out of the shower," Heather said meekly. "I'm expecting a delivery and didn't want to miss it."

"Uhh... uhm... I need a signature for this... ummm... ma'am," the driver managed to stutter out as he held out an electronic tablet for her to sign and his eyes wandered up and down her exposed flesh.

If Heather hadn't been so scared about what was coming next she would have thought how cute it was this guy was getting flustered. But she didn't have time to think about that, she had a job to do, and she knew SpareRod was watching. She reached to take the tablet in her left hand so she could sign with her right, and just like she had practiced, the skimpy towel dropped instantly to the ground.

"Oh FUCK!" Heather shouted uncontrollably. 

Even though she knew it was going to happen, suddenly standing stark naked at her front door almost put her body into shock. It was bad enough being ogled by the delivery man, but she hadn't counted on how exposed she would be to her entire street. She tried not to look but she noticed a car slowing down to a crawl as it drove by her house.




The Perils of Being Too Trusting Ch. 04



I want to say thanks for the offers to help edit, it all made this chapter go faster. A particular thanks to CuriousMG whose contributions are making the story much stronger. If anyone out there is good at reading copy or a very picky proof-reader, I could definitely still use help with that too. 

Hope everyone enjoys.

*****

Heather stuck her arm out her car window, trying to use her hand to force a breeze into her car. For the 100th time on the drive up to Denver, she cursed SpareRod and his stupid torments. This wasn't even sexy, being told she couldn't use the air conditioning in her car when it was almost 100 degrees. It helped that she was in a bikini, but she was still sweating profusely. He told her that he liked watching her shiny body as she drove, but mostly she just felt sticky and uncomfortable.

She was feeling even more uncomfortable about all the traffic on the highway. He had made her modify her bikini, removing all lining and leaving it ridiculously sheer. Her nipples and even her areolae could just be seen through the top, and the bottoms now showed a clear camel toe where the fabric pulled into her pussy. Her car was towered over by the trucks and SUVs on the highway, and more than a couple times it felt like they slowed down as they passed her to get a better view. 

He had made her wear the bikini for the drive, but allowed her to pack some different clothes in her trunk, presumably for when she got to Denver and actually started shopping. But until she got to the mall there was no telling what he'd make her do. Thinking about it, she realized there was no guarantee he wouldn't make her go into the mall in the bikini, but she was pretty sure that would get her arrested, or at least banned from the mall. But for now, all she could do was hope for the best.

Heather pulled into the immense mall parking lot, parked in the most remote spot she could find, and brought up the video chat on her phone. SpareRod connected almost immediately.

"Did you enjoy your ride up, slut?" he asked mischieviously. "You look all hot and bothered."

"Mostly just hot Sir," Heather whined. "It's hot as fuck here."

Actually, the truth was that she was more than a bit bothered too. The weekend had been unbelievably frustrating, being forced to dress like a slut, constantly edging, and the ban on orgasms was now stretching to almost a week. It seemed now like she was constantly turned on, and all of her thoughts were sexual in nature. She felt a deep and unrelenting need to get her brains fucked out.

It seemed like SpareRod had done everything he could over the weekend to keep her in that state. Even though there hadn't been any more opportunities for her to repeat her naked serving girl role for Keely, he had kept Heather dressed in a tiny t-shirt cut high on her midriff and the skimpy boyshorts whenever she was around her roommates. Saturday afternoon, he had even made her insert a small butt plug. She was pretty sure that neither of her roommates could see the shape of the plug through the panties, but it kept her embarrassed and turned on the whole afternoon. SpareRod's instructions had been to offer to do whatever her roommates wanted her to do, keeping her humiliation level high. They made her cook dinner, clean the kitchen, and vacuum the living room. Anna seemed a little shocked by it, but Keely seemed to be taking full advantage. She even gave her laundry to Heather to do on Sunday, while she and Anna went out, leaving Heather home alone. So she'd ended up doing Keely's laundry wearing nothing but a butt plug. When SpareRod found out, he upped the ante by making Heather pick out the sexiest panties that Keely had, and putting them in her mouth. He even had Heather fold the panties so the front of the gusset would go right on her tongue, so she could get a taste of Keely's pussy. It was so humiliating, it turned her on so much that she couldn't even come close to touching her pussy, even when SpareRod told her to edge. She had felt like she would cum from just one touch. 

She had eventually calmed down a little, especially once she was able to put the panties and midriff back on for her roommates' return, but the whole experience made her entire body buzz with sexual energy. Trying to deny that she was all worked up was pretty pointless. SpareRod clearly knew it, and proceeded to prove it to her.

"I think your engine is revving pretty close to redline slut," he responded. "Pull down those bikini bottoms and show me if your cunt is wet."

No surprise, Heather's pussy was not only wet, but puffy and open. At his urging she stuck two fingers inside herself, and the ease with which they went in betrayed how horny and wet she was. He made her finger bang herself until she was right on the edge of cumming, finally allowing her to stop and pull up the bikini. He was extra cruel though, and made her wedge the fabric up into her ass and pussy, exacerbating how sensitive her clit was. 

Holding the phone so he could watch, he had her walk to her trunk in the bikini, strip naked, and dress in the clothes he had picked out for her that morning. While part of her was getting used to being naked in risky situations, this was truly crazy. Her legs were wobbly as she tried to scurry around her car to the trunk, crouching a bit to try to be less conspicuous. It seemed to take forever to pull on her short jean skirt and a backless halter top. The top wasn't much more than a trapezoid of fabric across her chest that tied at her neck and the middle of her back. She had only worn it a couple times out clubbing; it really wasn't intended to be worn at a mall in the daytime. When she had modelled for him this morning, he made her tie the knots on her back tight, cinching its bottom around her torso about two inches above her navel. He also had her loosen the tie behind her neck. This made the halter hang down and away from her body a bit, showing quite a bit of side boob when she was standing. When she bent over, all the cloth hung away from her chest giving clear down-blouse and side-boob views of her nipples. The floral print fabric was thick enough that her nipples didn't really show through, but it hardly mattered with how easy it was for them to peek out. The skirt was the same one she had worn to buy the sex toys, and at only 13 inches long it pretty much only covered the bare necessities. Bending over, squatting, or even sitting was almost certain to make her expose herself. A pair of four inch wedge sandals, making her legs look longer, and her skirt even shorter, completed her outfit.

Once Heather composed herself, she grabbed her oversized purse and took the long walk across the parking lot, keeping her eyes down to avoid eye contact with anyone. The wind was blowing strongly, but he forbade her from holding her clothes in place. The jean skirt stayed mostly in place, but she was pretty sure her nipple was peeking in and out of view as her top fluttered in the wind. As she approached the doors, she watched her reflection, and while her nipple wasn't totally exposed from the front, her top was never covering very much of the rest of her boob.

As she walked through the mall towards the large department store SpareRod selected, she noticed a lot of people staring at her. The guys all seemed to stare in shock or lust, and the women in disapproval and disgust. Heather felt like her entire body was turning beet red, and she tried to just look at the floor in front her as she walked. SpareRod just added to her nervousness,chatting in her earbud about all the slutty clothes they would be buying. It seemed if it was short, tight, see-through, or easy opening, then she would be buying it today.

She wandered around the department store, holding things up to the camera for his approval. Not only was he picking out very revealing outfits, but he seemed to be deliberately picking the wrong size. She was sure this was all part of making the experience as embarrassing as possible. Soon she was headed to the changing rooms with an armful of clothing and was shown back to a dressing room.

Once her halter top was off, the first thing he had her try on was a sheer black long sleeve blouse that buttoned all the way up the front. He had made her get one that was clearly too large even though there had been plenty of all sizes on the rack. It was meant to be worn over another top, but once she had it on Heather realized it was well past sheer and on to completely see through. She could clearly see her breasts, nipples, areolae, belly button, everything through the fabric. 

"Call that girl who let you in back, she was kind of cute, I want to see her again. Tell her you got this blouse in a size too big, and ask her if there is a size smaller. Make sure not to cover up anything. I want her to get a nice view."

"Sir, I don't know her, she may get pissed off. It's really risky," Heather protested.

"She can't get that angry. I mean, at least I let you keep your skirt on, and you are actually covered for now. So call her back."

Heather felt an almost overwhelming urge to resist, but she could tell from his comment about only being covered for now that things were only going to get more intense from here. She tried not to think about all the butterflies in her stomach, set her phone so the camera would be looking out the booth door, and called for the girl. The sales clerk was probably a little younger than Heather, and SpareRod was right, she was kind of cute. Heather just hoped the girl had a good sense of humor. 

As the clerk walked towards Heather's booth, her eyes dropped down to Heather's breasts, and Heather could see the shock spread across the young woman's face. Heather asked if they had the blouse in a smaller size. Actually she had to ask twice, because the clerk seemed more focused on Heather's barely covered tits than what she was saying.

"Uh... uhm... sure," the clerk stammered, "I can go look. Uhhhm... you... uh... you do know that is supposed to be worn with something underneath?"

Heather was relieved the young woman seemed almost as nervous as Heather was. At least the clerk wasn't angry. Heather stood so SpareRod would be able to see her, making sure to stand straight, even thrusting her chest forward a bit to accentuate the view. It humiliated her to present herself like this, but then again, that was the point.

"Oh I know," Heather tried to sound casual, "but the top I had on would look totally wrong with it, and I didn't think anyone back here would care. You know?"

Heather ended on a question, and looked at the clerk expectantly, hoping that would draw out a response. The younger woman seemed to take a few seconds to come up with a response.

"Oh, it's okay with me," the clerk giggled nervously, "you wouldn't believe the half of what I've seen back here. But I can see why you're asking me to go get it for you, don't want people getting the wrong idea with you walking out there."

"See," SpareRod said to her as soon as the clerk was gone, "that wasn't too bad. So let's get ready for when she gets back. Make sure you're topless when she's back. Pretend to be looking at the other tops."

The wait for the clerk to come back was agonizing for Heather. She felt so exposed wearing just the skirt and sandals, knowing that at any time the woman would knock on her door. SpareRod commented that she looked antsy, so he had her alternate between tweaking her nipples and lifting her skirt to play with her pussy to take her mind off of how nervous she was. It didn't really help. 

Heather jumped when the knock on the door finally came. She rushed to push her skirt down, and grabbed a couple tops like she was deciding which one to try on next. There wasn't much she could do about her hard nipples or her fingers having a little of her juice on them. She opened the door, and made sure the clerk had a good chance to look at Heather before she took the new blouse and handed back the larger one. Heather thanked the girl, who could barely manage to mumble anything as she tried to look anywhere but at her topless customer.

He had Heather try on a couple other sheer tops, setting aside for purchase only the most transparent clothing she'd found. After that, he had her try on a button front shirt-dress that was several sizes too large. She knew he was going to find more ways to embarrass her, but even she didn't see what was coming next.

"Now slut," he commanded, "I want you to leave the dress completely unbuttoned and open, so she has a good view of your cunt and tits. You need to tell her that this is way too loose, and you need one or two sizes down. If she agrees to get it, and she doesn't say anything negative about your cunt being on display, then you need to tell her she can take this one back now, and strip naked to give her the dress back."

"Oh my God, Sir," Heather was breathless. "She'll freak out. She'll kick me out of here."

"We'll just have to take our shopping somewhere else then. You can do this slut. Don't disappoint me."

Heather unbuttoned the dress all the way, and let if fall open. Her crotch had just the barest hint of stubble now that it had been almost 10 days since she'd waxed. It seemed even more exposed to her to have that stubble to attract attention, but not enough to hide anything. She had to slide one side of the dress over to expose her breast, but she thought that would be good enough. This time she stepped out of the booth to call the girl back. She had a hard time keeping her voice steady as she asked for help. The girl's jaw actually dropped open when she came around the corner and saw Heather exposed like that. If anything the girl seemed more nervous than Heather.

"This dress is so loose it just doesn't look right," Heather flapped the dress open a few times to demonstrate how it flapped, exposing herself completely to the clerk. "Do you think you could find me a slightly smaller one? I want it to fit tight, you know?."

The girl was so embarrassed she couldn't even make eye contact with Heather, and barely managed to stammer out that she could probably bring Heather a couple different sizes. Heather had hoped that the girl might scold her, so she wouldn't have to go to the next level, but that wasn't in the cards. Before the girl could turn to leave, Heather told her that she could take this dress back, and striped naked to hand the dress back.

"Oh my God..." the girl was completely flustered. "Okay, yes ma'am, I'll take it, but you should go... uhm.. you need get back in the booth. Oh my God... please ma'am, you shouldn't be out here like that."

"It's okay, it's just us girls," Heather tried unsuccessfully to keep her voice from quaking. "I've never been much for modesty."

"Please ma'am, I don't want to get in trouble," the girl seemed genuinely worried. "It's not me, but if someone else came back here..."

The clerk didn't finish her sentence, but Heather was already heading back into her booth. Her calm facade broke as soon as she was back in the booth, and she started giggling hysterically. It took her several seconds before she could even talk to him.

"Holy Fuck!" she whispered. "That was crazy. My heart is like, exploding right now!"

"You did pretty well, slut," he complimented her. "Keep your door open a bit, I think you need a bit more exposure. Plus I'm not sure she knows how horny you are, so I want you to finger fuck yourself while you're waiting. I won't make you get out a toy right now, but you had better do a good job now or we'll move on to the toys."

Heather definitely did not want to get out the sex toys. She left her door slightly ajar, leaned against the wall behind the door so no one walking by could see her, and began playing with herself. Her pussy was soaking wet, and it did not take much preparation for her to start pumping her middle and ring finger in and out of her pussy. She was horrified by how loud the squishy noises were as she worked faster and faster. Fortunately, she heard the clerk coming and was able to stop and wipe her fingers off on her denim skirt before the girl knocked on the door. If the girl noticed anything odd, she didn't say anything. Even though she seemed very nervous, she did stay at the door longer than strictly necessary, asking Heather if she needed anything else. Maybe the woman was just making sure Heather didn't start wandering the store naked.

SpareRod guided her through trying on the other dresses. She kept a sheer one and also a crocheted one, both of which were intended as swimming cover-ups, not as something you'd wear with nothing underneath. She had to call back the clerk two more times, both times standing completely naked. SpareRod had her keep her door ajar too, although the clerk closed it on Heather the second time. SpareRod was disappointed that no one else came back into the changing area and saw Heather, but it was mid-morning on a Monday, so it wasn't too shocking. It didn't disappoint Heather in the slightest, since the experience was already embarrassing enough and she didn't see any reason it needed to be worse.

Finally she had selected the clothes he wanted her to buy, and redressed (if you could call it dressed) in the halter top and jeans skirt. Paying for the clothes was relatively uneventful, although the clerk seemed very nervous, and kept staring at Heather's outfit rather than looking Heather in the eye. At SpareRod's urging Heather tried to make some small talk with the clerk, but she seemed too flustered to respond, so a few minutes later Heather was walking out of the store.

"Well," SpareRod was a bit annoyed, "your pickup technique is a bit weak. We're going to have to work on that if you're going to get good at flirting with chicks."

"Well Sorrrrr-eee!" Heather huffed. "It's not like I've been spending all my time learning to pick up girls. Besides, what did you think would happen, that suddenly she'd be eating me out in the changing room like in some cheap porno?"

Heather noticed a couple heads turn towards her as she said that. She tried to be more discreet whispering into the microphone.

"Well, a guy can dream right? No, I just think you need to be a bit more flirty. You've started doing it with Keely, I want you doing it more often."

"You want me to get naked in front of random women and then flirt with them? And then jump their bones?" Heather phrased it intentionally to make it clear how ludicrous the idea was.

"Exactly," he came back without a trace of irony, "do you have any issues with that, slut? Seriously, I'm not talking about jumping their bones. Just if a woman does something that says she's a bit interested, you keep the conversation going, but work to play a little hard to get. Do things to keep her interest."

They chatted about their differing ideas about how to actually go about picking up girls, but it was clear that SpareRod had a much more scientific approach than Heather. The whole thing made her roll her eyes. It was so like him to take something fun like flirting and make it all clinical. 

Her next store was one that catered mostly to teens and young adults. She was a little bit older than girls who normally shopped there, but she dressed pretty young, so it didn't draw a second glance. The way she was dressed however, did cause a lot of people to stare. Heather did her best to ignore them while SpareRod helped her select some clothing. He had her pick out the 3 shortest miniskirts she could find in the store. Two were about 15 inches long and one was a bit longer but had a zipper up the front that unzipped from the bottom. She grabbed those and went to the changing room. There wasn't anyone to show her back, so she just went in.

"Okay," he said, "let's do something a bit different. Strip naked and get out that suction cup dildo. Good girl. I never get tired of seeing you naked with a dildo. Now let's see you do a couple minutes of blowjob practice."




The Perils of Being Too Trusting Ch. 04



Heather stuck the dildo to the mirror on the booth wall, and got down on her knees to suck the plastic cock. She had made a significant breakthrough yesterday after a few days of practice, and was able to hold open her throat a bit and slide all but about a half an inch of the dildo into her mouth. Every once and a while, it still made her gag, but she was able to slowly work the dildo in and out while he watched on camera. He was complimentary of her progress as she kept practicing. It felt weird to hear other customers walk by outside the flimsy booth while she was kneeling and sucking off a dildo. Hopefully no one looked under the door to see her on her knees. After a couple minutes he changed things up for her.

"You're making good progress slut," he was clearly enjoying this. "Stand up and turn to face away from the mirror, and then mount that dildo like I'm bending you over and fucking your brains out."

Heather couldn't believe where this was going. Granted, the booth door was closed and locked, but it was a pretty flimsy door, and had an 18 inch gap at the bottom. All someone would have to do is bend over a little bit and they'd see that Heather was up to something. She begged him not to do this, but he was unrelenting. She had to move the dildo down a bit on the mirror to get it in the right position. It took her a few tries, but once she had it in the right place, it slid easily into her swollen, wet pussy. Her feelings of dread at being caught, and embarrassment at what she was doing, receded as she rocked back and forth on the plastic cock. After days of teasing and edging herself, she was a bundle of pent up sexual energy, and the feeling of anything, even a dildo, fucking her pussy was amazing. She got herself into a good rhythm as she got more and more turned on. She bit her lower lip to keep quiet as she bounced her hips back and forth, bumping her bare ass against the mirror. She tried to stop a couple times when people walked by, but it felt so good she almost didn't care if they heard. She wanted so bad to just bang the shit out of the thing, but that would have caused a scene within minutes. She had no idea how long he kept her going, and her mind retreated into an erotic haze as she relished the sensations of the dildo pumping in and out of her. The haze was suddenly shattered by a knock on the booth door. Heather hadn't heard anyone coming, and almost shrieked with the rapping on the door.

"Is everything okay in there ma'am?" the woman sounded annoyed.

Heather assured her that everything was okay, hurriedly put the dildo away, and tried on the skirts. Thankfully SpareRod didn't make her open the door naked or anything, and a few minutes later she was buying the skirt that unzipped up the front. SpareRod felt the others weren't slutty enough. The older woman behind the counter gave Heather a dirty look, but she didn't say anything about what Heather had been doing, so Heather counted herself lucky to get out of the store unscathed.

Next he had her go to a smaller store that specialized in jeans and denim. There she was able to find some skirts much more to his liking. One was a very short 12 inch cut off jean skirt, and the other was a ridiculously scandalous 10" pleated denim skirt. She warned him that she'd' probably get arrested wearing the shorter one, but he insisted she take it.

The changing booths in this store were connected to the main room, and only had a curtain instead of a door. It made Heather feel much more exposed when he made her strip completely before she could try on the skirts. Standing there in just the 12 inch skirt was essentially like being naked. She could almost see the bottom of her ass cheeks peeking out the bottom of the skirt while she was standing, and when he made her bend over her pussy came into view. He had her sit with her knees apart, and again it was pretty much guaranteed that she'd be showing off her pussy.

As bad as that skirt was, the shorter, pleated skirt was unbelievable. She had to pull it low on her hips to just cover her pussy lips, to the point it felt like the stubble of her pubic hair might be exposed. When she sat on the bench in the booth, only her bare ass cheeks touched the seat. Turning her ass to the mirror and bending over at the waist not only exposed her pussy, but all the way up to her asshole. He kept posing her in different ways, clearly in love with how much of her body this skirt exposed, and he even said that he might have her alter more of her skirts at home to be this size. She was reduced to pleading with him to not make her wear something that would get her arrested. He just laughed and said that if she was going to get arrested, it would be for more than just a short skirt.

"In fact," he continued, "I think it's time to ramp up the risk a level. Let's get that dildo mounted on the mirror, and find the vibrating egg too."

"Oh my God, Sir," she hissed. "There's no door here, if a clerk comes there's nothing to stop them from just opening the curtain. I could get caught for sure."

"Naw," he didn't seem concerned, "they'd never just barge in, they'll say something first. You'll just need to be very quiet. Of course, that may be a bit harder this time - since the dildo will be in your ass."

"Holy fuck, I can't do that, Sir!" Heather couldn't believe what he was doing. "I'm not even sure that dildo will fit, and this is so public Sir. What if I get caught?"

"FIrst rule, slut," he said calmly, "is never panic. Now get that vibrating egg in and turn it to medium so you'll find the whole thing more enjoyable."

Never panic, it was easy for him to fucking say, Heather fumed. For the the thousandth time since this whole blackmailing disaster had started she considered telling him to stuff a giant dildo up his fucking ass and disconnecting from him entirely. She almost didn't care if he sent that video to all her friends and family and ruined her life. She was so mad at him that she couldn't think straight. But the more she thought about what would happen if he sent that video it became clearer that maybe getting caught masturbating in some mall 75 miles from her home would be bad, but not as bad as what he might do to her. She started looking through her bag for the vibrating egg, reversed course and closed the bag, then reversed again and found the egg. She realized that she looked like an idiot not knowing what to do next, but she was so torn inside.

"My," he chuckled, "you are an indecisive slut today..."

"Fuck you," she retorted automatically. "Sir."

"Oh I certainly hope to at some point, slut," he was still laughing, "but right now you'll be fucking that dildo and thinking of me. Now put the egg in your cunt before I get mad and decide to punish your insolence."

Heather's resistance was melting away, and she knew she had lost again. She slid the egg inside herself, and set the remote control to vibrate at medium. They had experimented with it over the weekend, and determined that medium could drive her crazy, but was unlikely to make her cum all on it's own. She wasn't sure that would hold true while fucking her ass with a dildo in a changing room, but he seemed determined to experiment. He did give her one more reminder not to cum before she placed the dildo on the mirror.

Heather tucked the back of the tiny skirt into the hem, put a cool dab of the lubricant on her rectum, pushed it into her ass with a finger, and also smeared lube on the dildo. Slowly she guided her asshole back onto the phallus. It stretched her uncomfortably, and it was incredibly difficult to keep quiet. She tried to control her breathing and focus on the pleasure as she inched her ass back, trying to get the entire cock up her ass. This was even more degrading than she had expected to be. Whenever she had had anal sex before, she had been mostly passive, and basically the guy did all the work. All she had ever needed to do was slow him down so nothing hurt too bad. Here she was doing all work by herself, including moving her phone around so he could get the best view of her ass being violated. 

"Good slut. Keep working that cock into your ass. Move me below so I can see your cunt too. Very good, now push harder. I want to see that thing balls deep in your ass."

Heather bore down on the dildo, grimacing a little at the burning sensation, but before too long she had her butt cheeks against the mirror and the dildo buried deep in her ass. She felt completely stuffed, and the vibrations from the egg in her pussy now spread into her ass, driving her crazy and eroding any will she had to resist what he was making her do to herself.

"Okay, now I want you to go all the way forward," he instructed, "pull yourself completely off the dildo." 

She felt so empty when the dildo fell out of her ass with an almost audible pop. He had her hold her phone over her asshole, just to watch it recover. She had to wait several seconds before he had her mount it again, again pushing herself until her ass was against the mirror. Not only did this slow pace make the process more uncomfortable, it also kept her from getting into a rhythm that would allow her to get anywhere close to an orgasm. 

Over and over he made her work herself down onto the dildo to the base, and then remove it entirely, waiting several seconds between each stroke. It was immensely frustrating to Heather, not being able to fuck herself properly. Beyond that, she had to listen to him go on and on about her asshole, and how it stayed open as she pulled it off the dildo. Finally, he let her go at it like she wanted to, sliding up and down on the well lubricated cock, bumping her ass hard against the mirror. She was so wrapped up in the pleasure that she almost forgot where she was. Suddenly, a noise nearby brought her back to reality, the footsteps of a sales woman approaching the booth. 

Panicked, Heather didn't know what to do. At the last second, she pulled the dildo off the mirror, leaving it buried deep in her ass. The tiny pleated skirt fell back down, although it barely went any lower than the dildo protruding from her rear end.

"Do you need any help, Miss?" a woman's voice came through the curtain.

Heather didn't even have to wait for his instructions, she knew what he'd make her do. She opened the curtain slightly, holding one hand behind her butt to hid the egg's remote control and to keep the dildo from slipping out of her ass. Holding the curtain open meant her bare breasts were visible to anyone in the store, although the clerk who had come to check on her was blocking most of that view. The woman was probably in her mid to late 30s, slightly plump with a pretty face. She seemed a bit perplexed by Heather, but at least she wasn't angry. Heather grabbed the 12 inch skirt off the bench and held it up.

"I really like this skirt," she improvised, "do you have one like it in a lighter color? I think I'd want that too."

Heather felt the dildo slipping out of her ass, and she pushed it back in deep, trying to hold it. The sliding sensation in her ass combined with jostling the vibrator deep in her pussy to make her legs wobble slightly. This was crazy, she was literally ass fucking herself while talking to the clerk, but she just couldn't stop herself. She slowly worked it in and out as held the skirt out for the woman to take with her free hand.

"Uhhm... sure," the woman looked up and down at Heather's naked torso, seeing how flushed it was, and her brow knitted. "You might want to be a bit more careful, it's a bit exposed right here."

The clerk was smiling as she said it, which relieved Heather a bit. At least she wasn't being all pissy like the clerk at the previous store. Once the woman walked away, SpareRod told her to keep the curtain a tiny bit open, and to really pump the dildo in and out of her ass. She felt like she was on autopilot, and dutifully kept reaming her ass. She couldn't do it too fast, both because she was worried if anyone peeked in, but also because with the riskiness of the situation she could feel an orgasm starting to build. Fortunately the clerk returned before too long and Heather could stop before she was at risk of having an orgasm without permission. Heather was feeling quite wanton now, and opened the curtain even wider to get the skirts the clerk had brought. The clerk laughed about how bold Heather was, but the older woman didn't really seem too concerned. Remembering his advice, Heather tried to engage her in a bit of conversation about which color she liked best. The woman didn't seem to know what to do, and just then another customer entered the store so she rushed off without really answering.

SpareRod allowed her to pull the toys out of herself and put them away. While part of Heather was grateful to ratchet back the risk level a bit, another part felt empty and unsatisfied at no longer being stuffed. She quickly tried on the other two skirts, selected one them, and got dressed again. Once out of the booth, she found the woman and went to complete her purchases.

"Wow," the clerk complimented her, "I can see why you wanted the skimpy skirts. You can definitely pull off that look. It's been years since I could do anything like that!"

The woman giggled and touched Heather's forearm as she said it. Heather demurred, saying she liked the skirts and that they were fun. Normally she might have been more self-deprecating, or said something to reassure the woman about how she wasn't that old. Instead she made up some stuff about how she couldn't wait to wear the clothes out to party. She wasn't sure if that's what he'd meant by playing a bit hard to get, but she was doing her best.

"You're young and you've got the looks to make it work, so I say live it up while the living is good," the clerk replied.

They laughed together, and kept chatting through the checkout process. Heather was a bit shocked when the clerk grabbed one of her business cards, wrote her mobile number on it, and told Heather to call if she ever wanted to see if they had any other clothes that would be fun. Heather was a bit flabbergasted, nothing like that had ever happened before. 

"That's awesome," she took the card with a smile, "I've never had my own private fashion consultant before."

Heather winked at the woman as she said that, and now it was the clerk's turn to be a little flabbergasted. She stammered a bit and said it was nothing. Heather opted not to say anything more, and sauntered out of the shop, hoping SpareRod would approve of her little bit of flirting.

"Well done, slut," he complimented her once she had her earpiece back in. "Got her phone number without even asking. You're a natural."

"Abso-fucking-lutely," Heather said with mock bravado. "Was she your kind of MILF, Sir. You looking to blackmail her once you're tired of me?"

"I would never get tired of you," he sounded genuinely wounded. "Why would you even say that?"

Heather was surprised that he was acting hurt, since he was the one blackmailing her, but she just moved on and asked if they were done shopping. He agreed they were, but he had one more thing he wanted her to do. She headed towards the exit nearest to where she parked, but before she could get there, he had her go into the ladies room. 

"You have to stay out in the public area," he was all business now, "and change into that crocheted mini-dress."

"Oh my fucking God," she muttered. "Sir, please. You know I can't wear that. I'll get arrested for sure."

"No you won't," he came back quickly, clearly getting angry. "You are right near the door and all you have to do is walk out of there and across the parking lot. No one will have time to say anything, much less call mall security. Now slut I'm telling you that you have to do this, so don't make me start punishing you on top of that."

Heather was truly scared by his tone of voice. He was definitely upset, and she knew that wouldn't go well for her. She went into the women's room, and checked under the stall doors to make sure she was alone. Once she was sure, she stripped off the sole two pieces of clothing she was wearing, and pulled the crocheted dress on. She had to smirk, because she was pretty sure that he thought she would be naked there for a while, and it had barely been 15 seconds. Definitely the upside of not wearing very much.

But this new dress took wearing very little to extremes. The crochet pattern formed small opaque diamonds, maybe three quarters of an inch vertically, and about a half inch across, separated by quarter inch gaps. The bottom line was the dress hid absolutely nothing. Even if she positioned a diamond over her nipple, it didn't cover it entirely so some part of her nipples would always be in view, as would her pussy slit, and the complete crack of her ass.

"Please Sir," she begged, "this is too much. Someone will call security."

"Only if you keep standing around like that. Remember who is in charge here, and get moving! No matter what happens, don't stop and go straight to your car."

Heather was really scared as she walked out into the mall. It took just a few seconds before people were gawking at her. She heard some people say loudly to look at that, and more than a few people laughing. She was pretty sure she heard one woman say something about getting dressed, but Heather walked away too quickly to hear for sure. She ended up just looking six feet in front of her, and walking as fast as she could out the door. The walk across the parking lot was terrifying, and she thought maybe a couple cars slowed down to get a better view of her. She zigged and zagged through the parked cars so no one could follow her easily. There was the sound of some screeching tires, followed by a crash and some breaking glass, but she didn't dare look to see if she had caused someone to bump into another car.

Thankfully she reached her car safely, and he did not make her strip before getting in. He had her jump behind the wheel and drive right away, just to make sure no one was following her. Once clear of the mall, he did have her pull into a strip mall about a mile away. Once the car stopped, the emotions suddenly washed over Heather, and she began laughing hysterically. Now that she realized that she wasn't going to be arrested or kidnapped or anything, the whole thing didn't seem nearly so bad.

"Fuuuuck me!" Heather finally got out between her giggles. "I can't believe I did that! It was so intense!! My nipples are so hard they hurt." 

She tugged on her nipples, earning an appreciative whistle from him.

"Did you hear the people yelling?!? The car crash?!? Holy fuck, I think I caused a car crash! I can stop traffic with this outfit." She lapsed back into uncontrollable giggling. 

Finally she calmed down, and he had her find her bikini top. The dress came off again, and for the drive home, only the bikini top went on. Heather wasn't too sure about driving all the way back home bottomless, but compared to what she'd already done it didn't seem so bad. Once the bikini top was tied snugly below her breasts, he had her untie it behind her neck, and re-tie it much more loosely. Just like with the halter, this made the cups fall away from her breasts, and made it quite easy for her nipples to pop into view. The truckers were going to get quite the show today. The final step to make things as extreme as possible was he had her put the butt plug in her ass, and the vibrating egg in her pussy. The vibrator was set on low this time, but it was still going to be a very distracting drive.

By now it was getting very hot in the car with her air conditioning turned off, so in spite of her humiliating situation, she was glad to be moving down the road and creating some kind of a breeze. By the time she was on the highway, the thrumming from deep in her womb, and the stuffed feelings in her asshole here getting to her, making her too turned on to worry if a trucker or two got a peek at her as she passed them. She tried to stay with the flow of traffic to keep too many people from getting a view. She definitely didn't want to cause an accident on the highway. The wind with her window open helped evaporate some of her sweat, but it was still a scorching day.




The Perils of Being Too Trusting Ch. 04



"Fuck," she sighed, "it's fucking hot, Sir. Can't I roll up the window and turn on the AC."

"I like seeing you glisten," he replied, "but I think I can do something to help you out. There's a Dairy Queen a few exits up, at least there is according to the internet, why don't you stop and get an ice cream cone."

Heather groaned to herself. She should have known he had something like that planned for her. She'd just have to hope that he didn't make her do something so extreme that she'd be arrested. It didn't take long to get to the Dairy Queen, but since it was now a very hot afternoon, there was a line of cars waiting at the drive through. All she could do was sit there and sweat while the cars crept forward. 

"I'm glad you like me glistening, Sir," she joked, "cuz I'm glistening like a horse right about now." 

"I do like it. Makes me think about how you'd look during a hot, sweaty fuck." 

In spite of her risky situation, that comment made Heather smile. She closed her eyes, leaned her head back and thought about how it would feel to get a long, hot drilling right about about now. She imagined a man on top of her, fucking her hard and long, bringing her to a that orgasm she'd been denied for days. Almost unbidden, SpareRod's face came into her minds eye, and she imagined him pounding away on top of her hot sweaty body. The image was so erotic she began fingering her pussy. She teased and rubbed her clit as she imagined all the ways SpareRod would fuck her.

"Easy there slut!" SpareRod teased her. "It looks like you're on a hair trigger."

Heather was definitely embarrassed that she'd been fingering herself while sitting in her car, but she was even more perturbed that he'd interrupted a really pleasant fantasy.

"Fuck, Sir, I'm just soooo worked up. This teasing is driving me crazy!"

"You can handle it, slut. I like you worked up. Besides cheer up, at least you'll have something cold to eat here soon. But let's make it more interesting. Put your purse in the back seat, and keep it there until you've pulled up to the cashier. When you get up to the cashier, I want you to kneel up on your seat and bend over to reach your purse in back. You need to do your best to moon them and make sure they see that plug in your ass."

"Really, Sir? You're really gonna make me do that? You're determined to get me arrested or raped, aren't you?" Heather whined. By this point she was more frustrated by all this than terrified. It just felt like he was going to keep going until she was caught.

"C'mon slut, give me some credit. Trust me, you'll be safe, and if anyone gets all upset, just drive away. But that isn't going to happen. No one gets upset at beautiful girls being naked. Just at old guys like me being naked. You'll be fine."

Heather smirked a little at the image of him trying to go through a drive-thru naked with a plug in his ass , but she had to bring herself back to reality quickly and try to steel herself for what was coming. She got to the board and ordered a cone, and waited to pull forward. Her heart was pounding and her stomach was doing flip flops. At this point the waiting was probably worse than the actual act was going to be. When there was only one car in front of her, he had her increase the vibrator speed to medium. It was almost too much for her, and she was squirming in her seat when she pulled up to the window.

"Oh!" she feigned surprise. "Now where is my purse?"

Heather turned to face away from the college age kid at the cash register, and climbed up to kneel on her seat so she could moon the kid as she reached to the back seat to get . She didn't hear anything from the kid, but she could hear SpareRod swear in her earpiece. She could only imagine the view the kid was getting of the plug in her ass and the wire coming out of her pussy to the vibrator's remote control. She had a brief, uncontrollable shiver as the thought of what she was doing got her even more turned on. She sat back down and paid for her cone. The guy at the window was basically stunned into silence. He handed her back her change, her cone, and mumbled something about having a nice day. Heather pulled the car over to a quiet spot, looked around to be sure no one could see her, and began massaging her pussy.

"Oh God, Sir... I'm so horny. Can I please cum now? It's crazy what you're doing, I'm so turned on."

"No, you gave me a lot of resistance today slut," he told her. "You'll need to be much better at following orders to earn an orgasm."

"Ahhhh, fuck!" that was not the answer Heather was hoping for. "Can I please take out the vibrator, Sir? I'm so worked up, I think I might cum with even on low."

"Well," he relented, "I'm not completely cruel all the time. You may take it out. You're probably going to lose signal driving back to Colorado Springs, so you'll need to record a video of your drive home. I'll allow you to put the bikini bottom on when you get home, and you can take the butt plug out once Keely or Anna gets home."

"Yes Sir. I understand Sir."

"Good girl. Remember to follow all your other rules. And enjoy the rest of your day off."

And with that, he was gone. Heather muttered to herself that it didn't feel very much like a fucking day off, but she set the phone up to record a video. It was crazy that she was still following his directions when he wasn't even around, but given everything else she had done for him, it seemed like driving bottomless on a quiet section of highway wasn't really the place to make a stand. Everything had actually worked out okay on this trip, and she just hoped it would keep working that way.

*

Brad startled awake, his heart pounding furiously in his chest. It took him several seconds to calm down and realize where he was. The dream had been so intense, and when the police had tackled him, all he could think of was that his life was ruined.

He had never had a bad dream about the police chasing him before. He still occasionally had the dream where he forgot to show up for a class all semester and it was now the final, or the dream where he was moving back into the house he grew up in, or the one where he could breathe under water, but never anything like this one. 

He knew that it was because of how hard he had pushed Heather this morning. He had realized as soon as he came down from the sexual high, that he had taken some huge risks. If she had been caught naked in public, and the police had gotten involved, not only would that have been the end of his adventures, she would have almost certainly told them she was being blackmailed. He couldn't believe he had gotten himself into this. He was committing a federal crime. He hadn't even had a parking ticket in years, and here he was risking being hunted down by the FBI; it was beyond insane.

While it was happening, and for several hours afterward while he watched the videos over and over while jacking off, he couldn't believe his good fortune. He was living out fantasies that he'd had for years, it was basically what he had been waiting for all his life. A girl with fantasies of being blackmailed unwittingly opened herself up to actually be blackmailed by him. This was not something that was ever likely to happen to him again. It was a temptation too strong to resist.

But after he'd burned up his sexual energy watching the videos and masturbating, the guilt and remorse would set in. When he had started this he mostly worried about what would happen if she had reported him. Now almost a week later he felt like that was less likely, although he had to be honest and recognize that it was always possible she eventually would. But he found himself in his quiet moments regretting what he was losing in his relationship with Heather. While it was clear that sometimes this really turned her on, and in some ways she was living out a fantasy, he also knew she hated it and was really angry with him. Try as he might to convince himself he was doing what she really wanted, he also knew it was a betrayal, and that wasn't the kind of guy he liked to think he was. 

He got out of bed, went to his computer, and spent several minutes looking at his "Heather" folder. For the hundredth time he highlighted all the files and hovered over the delete option. He could delete everything and send Heather a quick message that he would never bother her again. Delete all his accounts, remove all his stories from the web, and just disappear. Both he and Heather could just go back to their normal lives. 

But like every other time, he just couldn't do it. He didn't know where this was going, or how there was any chance that things would work out where Heather didn't just hate him forever. But he just couldn't get off this ride.

*

SPLAT!

Heather's legs snapped together involuntarily from the jolt of pain from her clit. She gently rubbed the cooking spoon up and down across her clit and pussy to disperse the sensation, feeling it replaced by a warm tingling. This was only the second time he had made her spank her pussy, and while it was definitely not her favorite thing to do, it did have some pleasant side effects. She was actually coating the spoon, her juices were flowing so freely.

"Sixteen," she panted. "Thank you Sir."

She had already spanked her ass fifty times, and each breast 25 times. The boobie spankings were definitely the hardest for her. The idea had seemed kind of sexy when she had only read about it, but the reality was that her nipples were too sensitive, and it hurt so much that it was hard to stay turned on. But the pussy spanks were definitely bringing it back. What was wrong with her that spanking herself like this on camera could leave her so horny?

SPLAT... SPLAT... SPLAT!

"Seventeen... Eighteen... OHHH... Nineteen," she couldn't control her moan. "Thank you sir."

"You're doing well slut," he encouraged her, "now make your last one really count."

Heather took several deep breaths to work herself up for it, and got a full swing in to bring the spoon down straight on her clit with as much force as she ever had. The explosion of sensation took her breath away. Her legs clamped together, and she rolled over on her side, her eyes screwed close as waves of pain and pleasure washed over her. It was unlike anything she'd ever felt, and it took her over a minute to sit back up.

"Twenty. Holy fuck Sir. Thank you Sir, that was crazy. I've never... that was fucked up, Sir."

"It looked like that last one really sent you for a loop. Very good slut. Now, let's try this again. Tell me all your rules, and we'll see if you can escape further punishment today."

Heather made sure her face was off camera before she rolled her eyes. SpareRod and his obsession with rules; it was kind of ridiculous. It wasn't like she had actually broken any of them. It was just when he put her on the spot, she hadn't been able to remember all of them. She hadn't actually said that she was required to be naked when she was home alone with Keely, but she hadn't been home alone with Keely since last Friday, what the fuck did it matter anyway? He had not seen it that way, and so the spankings had started. She took a few deep breaths, and started to recite the rules.

"Rule one is that I must call you Sir. Rule number two is that I am not allowed to cum without permission. Number three is that I am not allowed to wear any clothes when I am home alone, or just with Keely," she emphasized the part about Keely. "Rule number four is that I am only allowed to wear the clothes that you have previously approved for me or that you tell me to wear. Rule number five is that I must be on camera whenever I'm at home, and when possible even when I'm not home. Rule number six is that I must practice my blow job skills on my dildo four times a day, five minutes each time. I must always do that on camera so you can see my progress. Rule number seven is that I have to edge for five minutes in the shower while finger fucking my asshole, again on camera. Number eight is that when I get home from work, or at noon on my days off, I must give myself an enema so I'm ready for ass play. Rule number nine is that I am not allowed to sit on the furniture at home unless you specifically instruct me to do otherwise."

"Good girl," he complimented her, "you got them all this time. As a reward I think you should spend some time now with that new wand vibrator you got in the mail."

"Oh my god Sir. Thank you Sir. May I cum now Sir?" Heather was almost bouncing at the prospect of having an orgasm after all this time. 

"I told you slut, you will earn an orgasm when you show me you can be completely compliant. Now show me you're a good little slut, and use that toy to edge for me."

It was all Heather could do to keep herself from crying. She even felt tears well up in her eyes, but she wiped them away as she went to fetch the giant wand vibrator from her room. Why did he always have to be so mean to her? She had done so much for him. Okay, sometimes she tried to rebel and push back on him, but the things he wanted sometimes were so intense, so scary, it was only natural. She was only human, what did he really expect? Maybe this was all a game to him, but this was her life he was fucking with. 

Frustrated beyond what she had ever been, she plugged in the vibrator, positioned the computer so he could watch her sitting on the floor with her legs spread wide, and placed the ball of the wand on her slit. She knew he would see how she was pouting, but it was just the way she felt. Rather than say anything more, she just turned on the vibrator to get this over with.

"Holy shiiiit," she moaned, "that is... that is... wow, Sir - I don't think I'm going to last very long."

The vibrator felt unbelievably strong, and her hips started gyrating of their own accord. It quickly drove her annoyed mood away, it was hard to focus on anything other than what it was doing to her pussy. Her moans started getting louder, and she stuck her left hand in her mouth to bite it and stifle them. Her legs pushed hard, lifting her ass off the floor. Before she knew it, she was very close to the edge.

"Please Sir," she whined, "if you aren't going to let me cum, you'll have to let me stop. This thing is crazy, what it's doing to me."

"I think you can go a bit longer. I'm enjoying watching you squirm. Keep going until you can't hold off for even one more second."

Heather groaned, but she followed instructions. She thought she was going to explode any second, but he was right, she could hold out longer. After another minute she was begging again to let her stop, she was so close it was painful to hold back. He kept making her hold off, causing her to scream and curse at him, but she tried to keep going. Finally, when she thought she would cum or go completely insane he told her that she was allowed to stop.

"Ohhhhh fuck! Sir, that was so hard. Please... please let me cum!"

"I told you slut, that's not in the cards. You should just focus on showing me how you can comply. Demonstrating total compliance is the only way you'll be allowed to cum this week, so I'd work on that."

Only way she'd be allowed to cum this week? It had been a week already today, she didn't see how it could be even remotely possible to hold out for the rest of this week. Even holding out for the rest of the day was going to be close to impossible. She knew she just had to let go and immerse herself in being the total submissive.

"Yes Sir," she panted, "I'm yours. I'll do whatever you say."

"Very good slut," she could hear how he was smiling as he spoke. "I like hearing that from you. It reminds me, I think you need another rule, just to make it an even ten. So how about from now on, whether standing or sitting you must keep your legs spread. To be specific, let's say your knees should never have less than a ten inch gap between them. I won't make you stand like your bow legged, but it should give your pussy lots of air."

The way Heather was sitting now, she would have had to put her knees much closer together to only have ten inches between them. She knew that in most of the skirts she now owned, and without any panties that would mean a high risk that she'd be flashing people her bare pussy, but she was just too frazzled by the edging to put up any resistance.

"Yes Sir," she said, "I understand and I will do my best to never have my knees together."

"Very good slut. That was the way I like to see you comply. As a reward for that I think you should only have to edge three more times before we're done."

Heather groaned to herself at the thought of having to edge that many more times. But secretly she was also a bit pleased with herself that she'd shown him how submissive she could be. It seemed warped that she could feel that way in this situation, but she couldn't help but smile as she opened her legs even wider so she could give him a good show.

Slowly, she began to work herself to another edge.

*

Heather walked around the coffee shop a few times, trying to figure out the safest place to sit. It was almost certain that he was going to make her do something mind-bogglingly embarrassing, and probably illegal, so she knew she'd want her seat to be as out of sight as possible. She'd picked this smaller, locally owned place for a few reasons. It wasn't near campus and she'd only been here once before, so it was unlikely anyone would know her. Also, the staff were all in their 20s and seemed pretty laid back, which wasn't always the case in this town. Finally, the shop was kind of L-shaped, with the long part of the L being a corridor back to the restrooms with tables along one side. She decided to sit there, at the table closest to the bathroom, facing the rest of the shop. No one else was sitting in that part in the early afternoon, and she would be able to see anyone coming. She set up her computer, plugged it into the wall, and ran up quick to get an iced coffee with a brownie so no one would give her a hard time about hanging out.

Back at the table she sat down, keeping her knees apart according to her rules, opened the video chat with SpareRod, and inserted her earpiece. She sipped her coffee for just a few minutes before he came on. 

"Good to see you this afternoon slut, how are you doing today? I enjoyed the video of you edging at work this morning."

"Fuck, Sir," Heather's desperation poured out, "my pussy feels like it's buzzing all the time since you made me edge with that vibe yesterday. I've literally soaked my panties just since I put them on in the car."

"How does it feel to be out in public fully dressed? You haven't been this dressed other than during your babysitting for a while now."

"It feels good, Sir. Thank you for letting me dress like this for a change."

Heather had been a bit surprised when he had told her to change into this outfit after her midday shower and enema. Over the tiny g-string he had allowed her, she was wearing her longest remaining skirt that came to mid thigh. A sheer black bra, dark blue cami, and a very sheer black button-down blouse completed the outfit. It was a more sexy outfit than she would have worn a couple of weeks ago, particularly in the early afternoon, but it seemed like a lot of coverage compared to what he had made her wear this last week.

"Well, don't get too used to it," he warned. "I'm sure you're not surprised to hear that you won't get to keep all those clothes on all afternoon."

Heather started getting nervous, wondering how things would go from here. He did not clue her in right away, they just chatted for a while, talking about the cafe she was in, showing it to him on camera, and how her work day had gone. After a few minutes of stringing her along, he finally got to the point.

"I want you to take your bra off now. Do it right where you're sitting."




The Perils of Being Too Trusting



"Careful, it looks like you could go over the edge pretty easily there. I'd hate to have to punish you for cumming without permission."

His eager smile made it clear that he would actually enjoy every second of punishing her. Heather, on the other hand, was pretty sure she would not, so she pulled her hand away and sat back down. He had her sit with her legs spread wide again, now showing him everything. She even had to pull up her cami, ensuring a completely unobstructed view, plus showing off her firm belly. Only her breasts had any kind of cover, but her rock hard nipples made sure that they weren't really hidden either. He told her that she was to keep playing with her pussy while they talked, but she could stop whenever she was worried that she might cum. The only catch was that if she wasn't playing with her pussy then she needed to pinch, flick, and twist her nipples as cruelly as she could stand. That way not only should it drive her back from the edge of orgasm, but it should motivate her to get back to teasing her pussy more quickly as her nipples got sore. 

At least that was the idea, but the only flaw was that being forced to tweak and twist her nipples for him turned her on almost as much as rubbing her pussy, even if it did hurt a little. Actually it was more humiliating than painful. Humiliating first just in terms of punishing herself while he watched, but also because she was spending more time doing that than playing with her pussy, letting him know just how turned on she was. It let him know how far her buzzing, throbbing pussy could push her to go, what he could get her to do in this state.

She felt hot and flushed, and was squirming in her seat as they talked. She was getting to the point where she felt she would do almost anything to cum. The abuse to her nipples was no longer intense enough to really tamp down her pending orgasm. She was dying for him to make her rip off her camisole and be totally nude for him, but he just kept on talking through their fantasies. Finally, she told him that it wasn't working any more to have the fabric between her nipples and her fingers, and she asked if she might take off her last item of clothing. He smiled, commenting how he liked having her beg to get naked for him. She giggled and did an exaggerated performance of begging to take off her clothes since she was so hot. Suddenly she was struck with how sexy his smile was as he laughed out loud at her performance. When he regained composure he told her that she could certainly strip naked for him. 

Once she was naked, she probably made it another 30 seconds of stroking her clit before she was right back at the edge of orgasm. She had to twist her nipples even more cruelly, even digging her thumbnails into the tender buds. She knew they would likely be sore all week after this abuse, but she was beyond caring. He suddenly seemed sympathetic to her plight.

"Hmm... you poor girl," he said without a trace of irony, "you seem really on fire right now, like you can barely keep from cumming. Would you like to have an orgasm now?"

"Oh fuck yes! Please... I need to cum... Please let me cum," she begged, beyond caring how pathetic that made her seem.

"Good girl. You're getting close to where I'll let you. You just have one more thing you have to do for me. It will be hard for you. Almost unbearable, but I promise you can do it, and once you have, you can have as many orgasms as you want, or maybe can stand."

Almost unbearable? What could he be talking about? This state she was in now, that was fucking unbearable. How bad could it be? She had to find relief, she would do almost anything, so she told him she was ready. Ready for anything.

"I want you to tell me your secrets. Rub your pussy for me and tell me your deep dark secrets. Tell me your fantasies that you won't admit to anyone, ones you've never even admitted to yourself. I know it turns you on to think about humiliating yourself of being humiliated. Now I want you to do it, tell me your deepest, most shocking fantasies. Think about how humiliating it will be for you to even say them out loud. Tell me those hidden things about you that no one should know.

She was stunned for a second. She could barely speak. God, what could she say? It was so personal, so invasive, she wasn't even sure if she could say anything out loud. Finally she ended up just blurting out some stuff that she could remember from his stories.

"I fantasize about being humiliated, about being forced to be the bad girl. I imagine being blackmailed into acting like a slut, into being publicly exposed," she started.

"I know that, that's why you contacted me in the first place. Go deeper, tell me your really kinky secrets"

"Oh God... I want to cum so bad... please just let me cum."

"C'mon nawtyTeeze... more naughty and less tease... tell me your secret fantasies."

Her mind was spinning as she tried to think of all the ideas she had ever masturbated to, the kinkier, the better. She started blurting out ideas and they just kept flowing. About how she wanted to be tied up and spanked, to be caught naked or even masturbating by a bunch of her friends and teased mercilessly, to be locked outside of her house with no clothes on. He pressed her to be dirtier. She said about how she liked to be fucked, and not just in her pussy. She talked about being held by the hair and fucked in the mouth, having some stranger ram his cock down her throat before filling her stomach with cum. She had never even come close to deep throating before, and she had only swallowed a half dozen times or so in her life. She didn't mind giving head, but the idea of swallowing a guy's bodily fluids was not enjoyable to her. But here she was talking about it and it was turning her on beyond measure.

This was followed with fantasies about being used in her ass, of being fucked long and hard in her rear hole. She actually liked anal better than she did giving blowjobs. At least there was no swallowing involved, and as long as the guy used lots of lube, did lots of prep work on her, and went very slowly, it almost always made for a hot night of sex. But her fantasies were not like that. She told him about being used roughly in her ass, about having guys fuck her lubed only by her spit and her pussy juice. About being tied face down on a coffee table at a party and having random strangers stop by and violate her ass with their cocks and other objects.

She started talking out having multiple guys fuck her, or girls joining in. While she had had a few one night stands with girls, and she had dated two guys simultaneously a couple times, she had definitely never been in a threesome. But the words kept tumbling out of her mouth, describing all combinations of three, four, five or even more people, men and women, using her in every orifice, and in every possible way. 

Even though these fantasies were things she would never do in real life, talking about them as if they were real was driving her wild, making her thighs twitch. It was taking all her self-control not to cum. It wasn't so much that the situations she was describing were a turn-on in and of themselves, but more the liberating feeling she had of actually expressing these dark thoughts out loud. The feeling of losing all of her boundaries, of being forced to say these wicked and kinky things, it was all driving her to wilder and wilder extremes. 

"C'mon nawty," he urged, "think about how much you want to cum. Tell me some things that are really nasty, your deeper secrets. Who do you really want to do those things to you?"

Heather's first response was famous people, like Ryan Gosling or Kristen Bell, but his laugh let he know that wasn't what he was looking for. She imagined ex-boyfriends, or friends from school, which he seemed to like better. She had no idea why she mentioned Keely, but he really seemed to like the idea of her being forced to lick her roommate's pussy. Soon she was telling him stories of her roommates blackmailing her, forcing her to be her slave. Of course she didn't give him their full names, but she was too rattled to make anything up so she just used first names. By this point she was so worked up that she couldn't touch her pussy at all, she just flicked her nipples as she talked, more turned on than she had ever been in her life.

That's probably why things took an even darker turn.

She began adding kinky detail after kinky detail, about how Keely and Anna would blackmail her into being their little sex slave. They would keep her naked all the time, make her sleep in a cage, have her wake them every morning by licking their pussies. She made a big perverted leap imagining that they wouldn't let her use the toilet, making her go pee in the backyard. She definitely did not have a pee fetish, and honestly had never even really thought about it, but at this point she was throwing up every crazy, kinky, perverted idea should could, hoping he would let her cum. This one seemed to get his interest, and he asked her how it would feel, to be totally exposed in the backyard, to be forced to urinate in front of her roommates or maybe even her neighbors. While the peeing part didn't really turn her on, imagining how humiliated she would be made her ache with arousal. 

The next step in her descent into complete depravity was adding that her roommates would pee on her, eventually progressing to where they would pee directly in her mouth after she finished servicing them with her tongue every morning. This was totally crazy. She could barely stand to swallow a guy's jism, there was no way she would ever swallow urine! But it was so humiliating, and she just felt a deep need to explore ways she could be humiliated. He asked her more questions about this for a while, helping her revel in the erotic humiliation of the fantasy. He began prodding her to think of others who could humiliate her, real people in her life. He pushed her to think about what it would really feel like, if these people she knew treated her this way. The only thing she could think of was if it was someone she worked with, either from the restaurant where she waited tables, or maybe one of the dads of the kids she babysat. She opted for one of the dads, since she did work for one family, the O'Donnells, where the dad was quite handsome. She imagined him catching her masturbating in the basement after putting the kids down, and him disciplining and humiliating her for being such a horny slut. She imagined how he would strip her, spank her, use her in the ass and mouth, and then kick her out of the house totally naked. 

To ratchet it up, Heather brought the mom into the story, describing how after Mrs O'Donnell finding out what happened, she would be jealous of Heather and torture her mercilessly. The story was getting kinkier and crueler, and Heather's head was swimming. She felt totally out of control, looking into his eyes and saying the most perverted, depraved things she had ever thought of in her life. But the experience was so heady, so wild, she never wanted it to stop. So she took one more step into degeneracy. She added their adolescent daughter into the story, describing even more cruel and outrageous things that would befall Heather at the girl's hands. Heather couldn't believe she was saying these things. It was sick, wrong, and immoral to even contemplate these kinds of illegal acts. She wasn't a pedophile, and things like this had never entered her mind before. And again it wasn't the actual scenarios that turned her on, it was the simple fact of how wrong it felt to be saying it out loud. How she was humiliating herself in front of her online master, that was the real turn on. He kept his eyes on her and prodded her to keep describing this depraved fantasy. Fortunately he sensed this had gone as far along its twisted course as it could, and he brought her back to the here and now.

"You look like you are in agony waiting to cum my pet. Would you like to cum now?"

"Oh God. More than anything, Sir. Please may I cum?"

"Begin to rub your pussy again, maybe I will let you."

"Please Sir, I can't even touch it right now. If I do, I will cum right away for sure. Please don't make me do anything if I can't cum right away."

"You can do it. Trust me. Start playing with her pussy."

Slowly, tentatively she began stroking her swollen lips and just barely teased her tender clit. Her body convulsed involuntarily the sensations were so intense, but she managed not to orgasm. Barely.

"Please Sir, please let me cum," she whimpered.

"You have been a very good girl nawtyteeze. You may cum for me now. Cum hard for me."

Just hearing the words come out of his mouth, the orgasm ripped her body. Her legs jerked and convulsed uncontrollably. Her back arched, and all the muscles in her body seemed to clench all at once. The orgasm hit her so hard and so fast that she was seared with pain. She knew she must look ridiculous as she flopped around in front of the camera, but she was so far gone, all she could focus on was the release that she desperately needed. Through the buzzing in her ears she could vaguely hear him urging her on, telling her to make it last as long as she could. She couldn't rub her clit anymore, it was too sensitive, but she alternated between squeezing her crotch and lightly slapping it, sending echoing jolts of pleasure through her body. She wasn't really sure if she had multiple orgasms, or just one very long one, but the experience was unlike anything she had ever had before. By the time it subsided, she was as relaxed and limp as a ragdoll. She finally looked up at him smiling at her.

"Well that looked like fun," he chuckled.

"Oh... my... fucking...God... Un-fucking-believable... I've never done... I've never had... that was fucking crazy... I can't believe how that felt so FUCKING GOOD!"

On one hand she was totally humiliated by all the things she had said to him, by the perverted kinky things that had come out of her mouth, but on the other hand she couldn't shake the earth shattering intensity the orgasm. They talked for a bit about how wild all this had been, and they agreed they should do it again. She tried to protest that she didn't think she could delve to the same depths of depravity, but he wouldn't commit that she would get what she wanted. After a few more minutes, they signed off. She thought briefly about asking whether or not he had gotten off, but he didn't volunteer anything, and she felt awkward asking so she let it go. She just barely managed to get dressed again before her roommates got home, and tried to act as normal as possible for the rest of the evening.

*

Brad pushed away from the desk in his hotel room, closing down the recording app that had stored the entirety of his and nawtyteeze's chat to the hard drive. His dick was so hard it was almost in pain. That had to have been one of the hottest experiences of his life. He had started off the day with truly low expectations, and now his mind was pretty much blown. Not only had that been crazily hot, and not only would it give him hours of spank material re-watching it over and over again, but it had also opened up all kinds of new possibilities. 

He had been writing dirty stories and putting them on the internet for over five years now, but this was something totally new and different. When he started posting things online, he had immediately had several people email him, wanting to talk about his stories, or stories they would like, and all kinds of interesting propositions. Many came with pictures of naked women the authors claimed were of themselves. He was obviously very skeptical, just because it stretched credulity that women would send naked pictures of themselves to complete strangers as an opening email. He did always try to correspond with everyone who emailed him, just to see what else would come of it. Plus, whether the pictures were real or not, they were always very sexy and he enjoyed them no matter what. He would usually ask for some additional photos, suggesting certain poses which would lend more credibility to the idea that the author was the same as the girl in the pictures, but invariably that had never worked out. Somehow their camera was broken, there boyfriend had taken it, or some other story, but he never got any pictures, videos, or anything that led him to believe the photos were authentic. 

In the few cases where the correspondence went back forth over longer periods of time, he had usually ended up using instant messaging too. Admittedly, every once in a while he would get an unsettling feeling that the woman he was chatting with was really some guy messing with his head, Brad usually exiled those thoughts quickly. Since this was all about exploring fantasy, he usually worked on suspending his disbelief, and enjoying the ride. That didn't stop him from asking for pictures, or to try video chat, it just never seemed to lead to anything beyond the occasional random image in his inbox. Not that he minded, since every once in a while the exchanges blossomed into very erotic dialogs that led to new story ideas, even if he had no idea what the other person looked like.

When nawtyteeze had first contacted him, he had figured it would play out about the same way as it always did. He had been pleasantly surprised how quickly she had engaged in conversation, and he enjoyed her creativity and enthusiasm for smut. His sense of things was that she was being honest about most things, but he knew it was not likely she was actually a 24 year old girl out exploring her fantasies of being a submissive. What were the odds that a girl like that would really want that with some 49 year old divorced guy?

Consequently, he had been completely surprised when nawtyteeze had agreed to a video chat, and had been very skeptical that it would really happen. The initial surprise of her actually showing up on the video chat had been quickly overtaken by the utter shock that she was not only really female, and really in her 20s, but she was really cute too. Maybe not supermodel hot or anything, but very cute, and with an awesome sexy body. Even if this was a one-time thing, he figured that this might be the crowning achievement of his adventures in writing erotica. 

Now looking back at the session, his mind could barely take it all in. She had been so creative, so inventive in her perversion, he had felt like he barely had a role in the chat. All he had to do was give her some minor prodding every now and again, and she had exposed a kinky mind that was awe inspiring. Listening to her fantasies of her roommates abusing her had turned him on so much he had almost lost it right on the spot. The fantasies about the family where she babysat were not his cup of tea in terms of fantasy, but he had let her run with it. And watching her orgasm at the end, what a mind-blower! He had taken a risk by telling her to cum like that. If she had not cum right away it would have ruined his hold over her. But the speed and intensity of her orgasm was unlike anything he had ever seen.

And the more he thought about it, he realized the things she had said in this chat might lead him to a whole new level with nawtyteeze. He wasn't sure if he could do it, and if it went wrong the consequences would be very serious for him. But if he stayed strong, and played his cards right, the possibilities were beyond anything he could have ever hoped for.

He had a lot of preparation to do, and he could see that he had a lot of work ahead of him. But first he was going to replay that video and enjoy every minute of it.

*

Heather woke up the next morning feeing more satisfied than she had in a long time. The killer orgasm from the chat, plus several more overnight had put a perpetual smile on her face. Even the protests of pain from her nipples when she scraped them along her sheets rolling over were not enough to mute her smile. She did regret being quite so rough on her boobs, but it seemed an acceptable price to pay. A couple times she had had pangs of shame about the things she had said during the chat. It had felt a little awkward to hang out with Anna and Keely last night after having created fantasies of them dominating her, and she had no idea of how she could ever be normal around the O'Donnells again after her truly degenerate fantasy about them, but thankfully those thoughts faded quickly and she had enjoyed the evening reliving the experience in her mind, and masturbating frequently.




The Perils of Being Too Trusting



She hustled herself out of bed, moving quickly to get ready for work waiting tables at the restaurant. It was a good job, especially since she got along great with everyone there. Since they only did breakfast and lunch, it also worked well for her babysitting gigs in the afternoons and evenings when she could get them. Not exactly what she had planned for when she had graduated with her Environmental Policy degree almost exactly a year ago, but it seemed like more than a few of her fellow graduates were not doing what they had intended when they got their degrees.

The restaurant was busy, and she didn't get a chance to log her phone into her nawtyteeze chat until she had finished her shift. She was a little disappointed not to see him online, they usually chatted every day. When she got home she used her computer to check for him. She wasn't sure she was up for another video chat, but she craved talking to him again. There was no sign of him online, so she finally checked her email. Her joy at finding a message from him quickly switched to horror as she read the message.

nawty,

your life as you know it is about to change. you say you fantasize about being blackmailed, about being forced to do things that you would never do otherwise. I am going to grace you with that experience in real life. As soon as you read this, you will strip naked and open your video chat. Ping me that you are ready to serve me. Failure to comply will force me to post the attached video to a very public website. I don't think I need to explain to you the reaction that your friends, family, or employers would have to this video. I expect complete compliance.

SpareRod

Heather felt light headed, and she almost fell over as she slumped into her chair. Numbly she clicked on the attachment to the email. It was even worse than she could have imagined. He had edited down their chat, showing her undressing and masturbating for the camera. The video was crystal clear, and she could see every detail of her face and body. Anyone seeing this would know it was her. Even worse, the sound was flawless as well, and he had clearly edited the most incriminating tidbits together. She was horrified. There was this mindless slut, naked and unable to stop playing with heself, talking about being dominated and abused by her two roommates. She even used their real names. Then it was ten times worse talking about the O'Donnells, who she also had described with their real names, even for the daughter. Heather was almost hyperventilating that the thought of Mr. O'Donnell seeing this, listening to her perverted fantasies for him and his wife, and then for his precious oldest daughter. At the very best Heather would be banned from babysitting. He might even call the police. Heather's head was swimming with panic and fear.

How could this have happened to her?

How could she have trusted him?