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.