The Perils of Being Too Trusting Ch. 03

"I'm sorry," she mumbled as she tried to grab the towel off the ground. "Damn towel is too small."

"It's okay, ma'am," the driver was trying to be polite, "these things happen I guess."

Heather briefly struggled to try and pick up the towel and figure out how to put it back on while holding the tablet, but decided that would take longer than just signing for the package. She laughed, tucked the towel under her arm, and signed for him. She made a point of staying out in the open so SpareRod would know she was exposed to the street, and even stood with her legs slightly apart. Her crotch hairs had not grown in at all yet, so her engorged lips were clearly on display.

"I guess since you've already seen it all," she laughed, "we might as well get this over with."

He didn't seem to know what to say to that, so he kept quiet. She handed him back the tablet, he gave her the envelope, and as soon as her door was closed she found herself laughing hysterically.

"That was so fucking crazy!" she shouted at her computer between bursts of laughter. "I'm literally shaking. I thought my heart was going to explode!"

"You did that quite well, slut," he congratulated her. "It would have been better if you had managed to turn around and bend over so he could see your ass, but we'll save that for next..."

Heather cut him off with a loud scream. After checking the return address on the envelope, and deciding that trying to track down a Mr Rod Spare from Kansas City wasn't going to lead her any closer to knowing who SpareRod really was, she opened the envelope. The scream escaped her lips as three fat bundles of twenty dollar bills fell onto her coffee table.

"Holy fuck!" Heather shouted. "This must be like $3,000! What are you, like a drug dealer or something?!?"

"No," he replied dryly, "I'm a blackmailer, remember? I wanted you to have the money, but given what I'm doing I didn't think it would be smart to make it easy to trace it back to me. Getting cash and sending it to you from some random place seemed to be safest thing."

"But you are the one blackmailing me. I'm not complaining, but doesn't this usually work the other way around?"

"Good point that," he laughed, "but trust me, my interests in you have absolutely nothing to do with what you have, and everything to do with who you are. I want you focused on what I want you to do, and not stressing about how you're going to pay for the things you'll need to to do that."

"What the fuck do you want me to do that's gonna cost me $3,000??!?!?"

"Well, not that much right away," he chuckled, "but I wanted to be sure it was more than enough so we wouldn't have to talk about how much money things cost. I hate that kind of thing."

"Well," Heather rolled her eyes, "thank God we won't have to do that. I mean, I'd hate for money to get in the way of you blackmailing me into parading around naked in front of strangers."

"Exactly," he deadpanned. "Besides you're barely making ends meet now. Money is definitely something I can bring to make this a lot more exciting."

"Even more exciting, oh yay," Heather came back sarcastically, "I can hardly wait. So what, are you some kind of a gazillionaire?"

"I told you, I got very lucky at getting in on the ground floor at a tech company and made out well when they were acquired. I'm not 'never have to work again' rich, but I can do this pretty easily, and it is SO worth it to me."

"Okay, so I'm scared to ask, but what will I be doing with my new loot?"

"FIrst off, we're getting the video chat set up on your phone so I can watch you even when you're not at home. Your phone bill will go up a bit, but you can afford it now. Next you need some sex toys. I've been doing a little research, and surprisingly even in a conservative place like Colorado Springs there are several place you can buy a dildo."

"Oh fuck," Heather swore, "you're going to make me go to a sex shop, aren't you? Please Sir, I've never done anything like that, can't we just order it online?"

"Now where would the fun be in that? Let's get you dressed so you can go buy some paddles and nipple clamps."

Those words drove spike of terror into Heather's heart. Go buy bondage toys in person!?!? Have to look someone in the eye as she pays for them? It was all insane; she knew she needed to argue with him.

"It's funny slut," he interrupted her thoughts, "I've been editing some videos of you, particularly with you talking about what you want to do that sweet young O'Donnell girl. It's very convenient I have both your parents' and her parents' emails addresses right here, so I can be sure they get to see and hear your dirty little fantasies."

Heather could hear the smirk in his voice. She was pretty sure he wouldn't actually do it since it would take away all of his fun, but just the slightest chance that those closest to her would see that video made her stomach do flip-flops. There would be no way to explain to her parents, to the O'Donells, why she had said those horrible, twisted fantasies. It was too scary to contemplate; she knew she would do what he wanted.

He told her to put on the camisole she'd worn under her blouse, her newly shortened jean skirt, and the highest heels she owned. She looked at herself on the screen as she modelled for him, and all she saw was a total slut. Her nipples were clearly visible through the clingy fabric of the cami, and the high heels made the tiny skirt seem even shorter. She looked like an absolute whore. She hoped to God that she didn't run into anyone who knew her.

They spent a few minutes more setting up her phone to do video chat. She brought the phone with her, and did her best to keep him entertained while she drove. Having him live was even worse than sending him pictures, mostly because he kept up a running commentary, including instructions on how to adjust her clothing. He make her hike her skirt up so she wasn't sitting on it, and then tuck the front in so her pussy was completely exposed. He let her keep her breasts covered when she stopped at traffic lights, but while she was driving he made her lower her top down to her waist, basically making the cami and skirt no more than a belt around her waist. It was even more humiliating that she couldn't stop playing with her nipples while she drove.

He gave her an address on the east side of town, and she was surprised when she arrived that it seemed like any ordinary store in a strip mall. She had expected something really run down and seedy, not something that looked so respectable. Inside the store looked a cross between lingerie and a t-shirt shop, and it actually took her a moment to find the section in back behind the tall shelves where the adult items were. She'd read about places like these, but had never been in anything like it in real life. The back of the store looked a little more seedy, but still looked safe enough to her. It seemed to be mostly a bunch of sex toys, kinky lingerie, lotions and lubes, with some small racks of magazines and movies. She wondered who would buy those anymore with so much porn on the internet, but there were a few men looking through them, so she guessed there was still a market for it.

She used the earbuds on her phone and was able to keep up a bit of a conversation with SpareRod while she browsed per his instructions. He seemed very disappointed when he saw the woman behind the counter was over 50 and probably over 200 pounds. He joked that it was too bad that real life didn't work like a porn movie where the girl behind the counter would be super hot, horny, and who would force Heather to submit in all kinds of kinky ways. Heather had to giggle at the idea, but was glad that he wasn't going to make her do anything gross with the woman. On top of that, there were a few couples there shopping together, and the girls were giving Heather dirty looks already. They didn't look like they would appreciate Heather putting on some kind of sex show. Actually, one of them looked like she would probably gouge Heather's eyes out if Heather gave her the slightest reason.

She did notice a few men seemed to be spending more time watching her than really browsing the store. She guessed they didn't see single women in here very often, at least not dressed like Heather was. When she commented on that to SpareRod, he came up with a challenge for her. In between shopping for dildos, nipple clamps, and vibrators she also needed to flash her pussy to one person and her tits to a different guy.

"But Sir," she whispered into the mike of her earbuds, "I can't. They might attack me!"

"As much as they might think about it," he chided her, "no one is going to attack you. Don't lead anyone on, don't make eye contact, and just make it look totally accidental. They probably won't even dare talk to you, but if they do you can just go straight to the counter to make your purchases."

Heather could feel her heart pounding at the idea that she would flash more strangers today.

"Sir, I'm not sure I can."

"Oh come on now, slut," he sounded annoyed. "Don't make me threaten you again. You just stood stark naked in front of the delivery man, you can certainly arrange a nipple slip or an upskirt right now. Get one done now, and then we'll shop for a while. Let's GO!"

Heather jumped from his sudden tone. She knew he was right, that she just needed to move fast and not think about it. She looked around and found an older guy browsing the bargain movies that looked safe enough. She walked one aisle over so she was facing him with a rack of movies between them. Trying to appear nonchalant, she scratched her shoulder and moved the spaghetti strap on the camisole over so it would slide down her arm. Heather had to work to keep a straight face as she tried to let the strap slide low enough for her nipple to come into view. Unfortunately, she was too turned on and her nipple was too hard to let the top slip by. SpareRod's laughter made her blush even more as she had to twist and shimmie a bit before her nipple popped into view. She let it stay in view for at least a full second before she gasped and pulled the cami back into place. She couldn't even make eye contact with the guy as she shuffled her way back towards the bondage section to finish her shopping list. It took her another ten minutes with SpareRod giving her pointers on spanking paddles and all kinds of kinky things before he was satisfied with her selections.

Flashing her pussy proved to be easier. She just dropped the box of three different sizes of butt-plugs onto the floor, making a loud bang that caused everyone to look her way. All she had to do was squat down without keeping her legs together, and her short skirt ensured that several guys got a good show. She could tell she had accomplished her mission by the way they craned their necks to get a better view. She tried to manipulate her phone so SpareRod got a view up her skirt too, and as soon as she heard his appreciative whistle she stood up and scurried to the checkout. After five humiliating minutes of the woman behind the counter inspecting all of her kinky purchases, laying them on the counter for everyone to see, Heather raced out of the store. The experience had humiliated her to the core. Just the smirk on the woman's face made Heather want a giant hole to open up in the floor and swallow her. Even though she knew SpareRod would continue to humiliate her in the car and at home, she couldn't wait to get out of there and into the relative safety of her car.

She was of course right that he would keep the pressure up, and as soon as she stopped at the first stoplight, he told her to remove her skirt. While she had been telling him all afternoon that this skirt was useless for protecting her modesty, that didn't mean she thought it would be okay to take it off. As short as the skirt was, the camisole barely met the skirt at her waist, so she would have no coverage at all for her ass and pussy. Instinctively she wanted to argue with him, but she caught herself before he could demand that she drive nude instead. Even though driving naked in broad daylight would probably get her arrested, she knew that he might make her do it if she pushed it, so she unbuttoned the waist of her skirt and slid it off before the light turned green. She knew that anyone in a taller vehicle would be able to look down and see her bottomless, and she instinctively covered her crotch with her left hand while driving with her right. Unfortunately, he did not approve and he made her spread her legs and finger herself as she drove, keeping herself on edge the entire time. She drove very carefully, sticking to the right lane hoping no one would get a good view, and was amazed that she got home without incident.

She didn't know why she thought he would let her put the skirt back on to walk from her car to her house, but it still surprised her when he told her to remain bottomless and walk slowly, slinging the bag of sex toys over her shoulder. Not only would she be unable to hide her pussy or her ass, but this position would also force her to thrust out her tits so people could clearly see her nipples through the camisole. She kept her eyes locked on her front door for the entire time, so she didn't know if any of her neighbors were watching her as she walked to the front door. Even though she thought she would be getting used to this by now, she still wanted to die of shame.

If any neighbors saw her bare ass, none of them shouted at her before she got inside. It was good he reminded her to get naked once across the threshold of her door, rather than be cruel and wait for her to forget so he could punish her. She knew that normally that would be his style, so she figured he must be in a good mood after her showing off at the store.

"Okay slut, let's try out a few of your new purchases."

Or maybe he just wanted to get right to playing with the toys.

"Let's start with that six inch dildo you bought, the one with suction cup. Find a chair it can mount to."

Heather's dining room chairs had flat wooden seats, and she found that with a bit of saliva the dildo attached solidly, the phallus thrusting upward obscenely.

"How wet are you?" he asked, "I'm wondering if you can climb on that thing with out any prep? Why don't you try that for me?"

She could tell from his tone that this wasn't actually a really a request, and she really didn't want to spank her nipples today, so she worked quickly to fit the fake cock into her pussy. To her utter humiliation, not only did the dildo enter her easily, but she slid quickly down until her ass touched the chair. She knew she was turned on, but it was a shock to see how wet and open she really was.

"Oh my, " his voice was almost a gasp, "I knew you liked doing this stuff slut, but I had no idea. But don't stop, I want you working that in and and out of your sweet little cunt. Good little slut. Just like that. Not too fast! Definitely no cumming allowed, but keep moving at all times."

Heather was thoroughly humiliated to have him know once again how turned on she was by what he was doing, but it got even worse when an involuntary moan escaped her lips. He chuckled and guided her through another minute of slow, teasing strokes, building her up even closer to orgasm. Finally he let her stop, instead instructing her to set up her sewing machine so she could do some work while bobbing up and down on the dildo. It took her a few minutes, but soon she was back on the dildo, trying to measure a work skirt to trim it to be 15 inches. While that was longer than the skirt she had just been wearing, it was definitely going to attract attention at work. She tried to put that out of her mind and focus on just getting the skirt done. Not that it was easy to focus while he was chatting with her and keeping her bouncing on the dildo.

"How much longer until you have to leave for your babysitting job tonight?"

"About an hour from now. It only takes me 10 minutes to get there. But they're going out a bit late since it's Friday, so I won't be home until after 11:00."

"Okay. I want you to wear what you wore to the sex shop to drive over there, but once you're there, change into what you wore to work, except of course you'll need to put on underwear. I'll send you a message for instructions on the way home."

"I understand, Sir."

"Good slut. Until then, I want you to keep fucking that cunt on that dildo. Of course I imagine your legs will get very tired, maybe even cramp up, so you can take a rest whenever you want."

"Thank you, Sir," Heather answered , even though she knew there was a catch coming.

"Of course, you'll need to keep occupied while you're resting, so whenever you're resting I want you to use the dildo to practice your deepthroat technique. I seem to remember you saying you didn't like blowjobs, so I'm figuring you need the practice."

"Oh my God," she protested. "But the dildo, it's covered in my schnizz. That's so gross!"

His peals of laughter did not make her feel any better.

"Wait," he asked once his laughter was under control, "you told me that you've gone down on another girl before?"

"Well," she stammered sheepishly, "yeah, I did. Well I did the one time. I finger banged girls the other times. Plus I was drunk. And I've given a lot of blowjobs, but never after having it in my pussy first. It's bad enough that I might have to have guys' cum in my mouth, there's no way I want my juices too. I kinda have issues with bodily fluids."

"Well, I guess you'll have to get over that," he was still laughing. "I'm sure in time you'll learn to love the taste of your own juices. Why don't you show me your deep throat technique before I log off?"

"My technique? I told you I don't have any fucking technique!"

"All the more reason for you to practice now. Don't get me upset slut!"

Heather sighed, lifted herself off of the dildo, pried it from the chair, and brought it up to her mouth. The bright pink phallus was shiny with her lube, but she decided she had to just go for it. She plunged it into her mouth and managed to get almost two thirds of it in before it tickled her gag reflex. While she wouldn't call the taste pleasant, it wasn't anywhere near as bad as she had been afraid it would be. She started to use her best blowjob skills, looking at the camera and trying to be as sexy as she knew how, hoping to get back on his good side. She even started to really get into it.

"You're kidding right?" his question disrupted her performance. "That looks like you only got what, four inches into your mouth? Is that really as deep as you can take it?"

Heather tried to protest that she had taken more, but he made her do it again, trying several times and letting him view from several angles. It was clear that she couldn't even take four inches into her mouth. He had her slowly work it in until she just started to gag, and hold it there for several seconds.

"Don't move it much, just hold it there for a bit. Good little slut. Now move it very slightly for the next 10 seconds."

Heather almost gagged a couple times, but by moving the dildo out just slightly and then back again, she found herself getting just slightly more comfortable with a penis starting to enter her throat.

"Getting there slut. Until you leave for babysitting, you'll either be bouncing on that cock on the chair, or when you're tired or think you might cum, then you will be practicing your deepthroat, holding that dildo as deep in your throat as you can. Understood?"

"I understand, Sir."

"I'll be recording you the rest of the afternoon, so I'll be able to check later if you followed instructions. Now, get to it slut. And try to do a good job on that skirt," he smirked.

Heather rolled her eyes at the comment about the skirt, but was at least glad to have him sign off without assigning any spankings. She reattached the dildo to her seat, and slid herself into position. She pondered how amazing it was that you could get used to something so quickly. Just a few days ago she wouldn't even think of sitting around naked in her own bedroom, and now she was naked in her dining room, fucking herself with her newly acquired sex toys, and in plain view of the windows at the front of the house. And as icing on the cake, she was trying to sew. She just hoped she didn't sew her finger or anything.