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."