The Perils of Being Too Trusting Ch. 03

It took just over five minutes for her legs to start cramping, so she had to switch to deep throat practice again. This time she barely noticed the taste of her own fluids. She could only take the dildo in her throat for about a minute or two, so she switched back again. Back and forth she went, for about 50 minutes. She never managed to get far on hemming the skirt, but otherwise she was sure she had followed instructions. But now she was covered in a sheen of sweat from the exertion, plus her legs were slick from her own juices, so she desperately needed a shower. She took her computer into her bathroom, and let him watch her shower. She knew he was recording all this, and she really didn't want to give him any reason to punish her, so she made the shower as sexy as she could. She wiggled her ass at the camera, spent extra time soaping her breasts, and even fingered her pussy and asshole for a while. She actually started to enjoy the show, although she had to stop for fear of cumming after riding a cock for the better part of an hour. Her body felt like it was vibrating with sexual energy, and she had no idea how she was going settle down once she had to babysit. Walking out to her car dressed like a slut didn't help. Surprisingly, even getting fully dressed for work, complete with underwear, didn't calm her down any. Although that was probably because she had to get naked in her car in broad daylight to do it. She found herself essentially permanently turned on by the time she texted a photo to him to prove she wasn't getting dressed too early. So turned on that before she knew it, she was sending him a video of herself fingering her pussy while she sat in the car. She knew it was more than he had asked for, but she just couldn't stop herself.

What was she turning into?

*

Brad popped open his beer, and started his computer as he unpacked the takeout boxes for his dinner. He had often thought that after years as a bachelor he should probably learn to cook, but the truth was it had never become a priority. It's not like take-out was that bad, and he certainly could afford it. While he was eating, he pulled up the recording of Heather bouncing on her new pink dildo, which made the meal seem even more special. He still couldn't believe his luck as he watched her lithe body work up and down on the fake cock. All he could think was how he would never get tired of watching this. The way her taut body tensed and rippled as the cock slid in and out of her; the way her perky tits bounced as she moved; the little moans and funny faces she made as she got herself more and more worked up. He was in heaven just watching her, and he had to undo his fly to relieve the pressure from his hardening cock.

Her efforts to improve her blowjob technique were more amusing than sexy, but he still enjoyed watching them. He thought she might have made about a quarter inch of progress, but it was hard to tell. He'd have to keep her working on this daily. He wasn't sure when he might take the risk to meet her face to face, but when the time came he wanted to make sure her blowjob skills were up to par. While he still would get the occasional blowjob, it had been a several years since he'd been lucky enough to be with a woman who could really deep throat. His penis strained even more as he imagined Heather giving him an enthusiastic blowjob.

If her activities in the dining room got him hard, the show she gave in the shower almost had him blowing his load. He swore softly as he watch her soap and tweak her nipples, shake her ass at him, even clean her asshole, getting three fingers into her ass at one point. He hadn't expected her to shower, and even if he had, he certainly didn't expect this little sex show. He couldn't tell for sure if she was doing it for him, or just because it made her hot, but he suspected it was a bit of both. He was amazed that just a few days after he started blackmailing her that she was back again to improvising and improving on his ideas. He had been afraid that she would hate him so much for blackmailing her that she would shut down and only do what he forced her to do. He wasn't sure exactly what it all meant, but he was loving it.

It wasn't until after he had cleaned up his dishes that he checked his messages. He didn't think that he could get any more turned on, but Heather's little video of masturbating in her car in broad daylight had him stroking fiercely. She looked so out of control horny, and it was completely beyond anything he had told her to do. It was an unbelievable turn on to think of her being so into being treated like this that she would keep looking for more and more intense experiences. He watched the video over and over as he jacked off.

Once he'd finally recovered, he thought more about how her new enthusiasm could work for him. He'd been terrified when he'd gone to the bank while in Kansas City and gotten all that cash. Even though he'd been careful, he knew that if she had brought in law enforcement they could track down him down some way, and he'd had a sleepless night after sending the cash. Now not only had she not called the police, but she had flashed the delivery man, bought some sex toys, and was sending him video snippets on her own initiative. He never would have thought things could go so well. His only worry was that now he would need to ratchet things up to stay in front of her. Originally he had worried he would push her too far too fast, but he had to trust that this was turning her on more than he could have ever guessed, and that she could handle more. He was pretty sure he could keep her amused tonight, but he needed to think of some bigger things for the coming days.

*

Heather felt like she had ants in her pants the entire time she was babysitting. Even though part of her was glad to be wearing panties and a bra again, the sensations from them were exacerbating her tingling pussy and her throbbing nipples. She would have guessed that edging for a couple days plus riding in a dildo for the better part of an hour would make her really horny, but knowing that in her head didn't prepare her for living it. She felt like her crotch was running a river of lube, and even with going to the bathroom frequently to dry herself, her panties were soaked. Fortunately the kids she was watching were wrapped up in some fantasy card trading game, so she could keep to herself and sneak in a few rubs here and there. But she didn't dare do any more than that for fear of cumming by accident. After the kids were down it was even more difficult to stay focused on normal activities, but somehow she managed to do dishes and read her book without playing with herself too much. It wouldn't do to get caught by the parents if they came home early. For the same reason she didn't dare log into her chat program to see if SpareRod had sent anything.

Finally the parents came home, and she raced back to her car. She could feel her heart starting to pound as she opened the messaging app on her phone. She wasn't sure it was with dread or anticipation, but either way there was a message and she had to focus on whatever came next.

SpareRod2003: First off slut, I want you to know that I appreciated your extra efforts this afternoon. You definitely have the right idea, it is always a good idea to try to exceed my expectations. As a reward you will only need to remove your bra and and panties for the drive home. You will need to play with your pussy as much as you can on the drive, but I'll allow you to enjoy some time covered up for your drive home. Text me when you're home

"Oh," Heather rolled her eyes, "you're going to let me stayed dressed now that it's dark and no one could see me anyways. Big deal!"

She had to take off her blouse briefly to remove her bra from under the camisole, but she put it right back on. She shucked her panties, and was on her way home.

Keely and Anna were in her living room when she home, and it appeared they were getting pretty drunk.

"Heaaaatherrrrrr," Anna slurred, "we've mished you so much."

"Wow," Heather was caught in a somewhat sloppy hug as she walked by the couch Anna was lounging on, "you two are having fun."

"We probably drank more wine at Rico's than we should have," admitted Keely. "Some guys started buying us drinks. The wine was okay, but they weren't really our types. So we had to get the fuck out after we drank up all their wine. Couldn't stop partying though, so we opened up another here. C'mon and join us."

"Uhm," Heather knew that she had to text SpareRod, so she needed to stall a bit. "Let me go change first."

"Yeah," Keely had a mischievous smile, "you do seem over-dressed, don't you?"

Heather blushed deeply, but didn't respond as she scurried back to her room. She almost closed the door behind her, but remembered her rules just in time and left it open. She did her best to step out of the view and strip naked while she brought up the video chat program on her computer. She didn't want to stay here naked with her door open too long, but she knew better than to get dressed without his permission. The idea of having to spank herself or leave the room naked while Anna and Keely were close was terrifying. Thankfully, he was already on so she didn't need to wait. She updated him on what her roommates were up to.

SpareRod2003: Well, since Keely asked you to join with them, I guess you'd better get back out there.

NawtySubSlut1989: Anna's there too, Sir. I can't go out there naked, she'll freak.

SpareRod2003: Don't worry slut, I'm understand your roommates' limits. We need to work them up slowly to your new subbie slut status. I think we let you keep a sleeveless top, right? Kind of a wife-beater?

Heather's heart started to pound at the thought of wearing that shirt. The armholes would almost continuously show a side-boob no matter how careful she was. She was going to be more exposed to Anna than she had ever been before, but she didn't want to protest for fear of what else he might make her do. She rushed to pull the top on, and found her boyshort panties from the other night. She was about put the underwear on when she heard her computer ping.

SpareRod2003: What are you doing, slut? you weren't about to get dressed without permission were you? I don't remember telling you that you could wear underwear.

"Please Sir," Heather hissed at the microphone on her computer, "I can't go out there bottomless."

SpareRod2003: Hmmm. Let me see. Stand back with your hands at your sides. Good girl - now turn around. I can't actually see your cunt, and only a bit of your ass cheeks, so it looks like you're acceptably covered. Get out there! And for not obeying immediately, I have a new rule. No more sitting on the furniture when you're at home. You may either stand, or sit on the floor, but no sitting on the furniture unless I specifically tell you to. And I'm only likely to tell you to do that when I want you to mount your dildo on it.

That definitely did not make her feel any better. She opened her mouth to beg him to change his mind, but she knew better by now. She grabbed her computer and headed into the living room.

"Holy shhhiiiit!" Anna shouted when she saw Heather. "You're not wearing much, are you."

"I guess you are getting closer to being a nudist aren't you," Keely winked at Heather as she poured her a glass of wine. "Who knows where this could lead?"

"Jussht don't be gettin' all naked an' shit right now," Anna slurred. "Don't want evrywun sshheeeing and thinking we're all sshluts."

"Ohhh, I think most folks already know what they think about you," Keely teased, "let Heather have her fun."

Heather laughed out loud as Anna flipped Keely the finger and yelled obscenities. Keely blew a kiss, and Anna stick out her tongue. They kept up their banter and Heather tried to decide what to do about sitting. At first she thought it would be safer to sit on the floor in front of the Keely's couch, since she was a more tolerant of her state of dress. But that would guarantee Anna a view up her skirt/shirt, so she decided it was better to sit next to Anna so only Keely might see Heather's private parts.

The girls gave her a funny look as she slid down and sat on the floor next to Anna. The shirt was so short and open on the sides that it was essentially impossible to be modest as she sunk to the floor. She was pretty sure Keely got a good view of her vaj and Anna saw her boob from the side as she positioned herself. She finally came to rest on the carpet with her thighs together, her feet tucked under her, and her computer off to the side. She felt her cheeks burning in embarrassment as the girls laughed at her and rolled their eyes. But at least they didn't say anything too catty. She positioned the computer so SpareRod could see her, she could see his chat, and (hopefully) Anna could see nothing. She just prayed they believed Heather was checking her social media and things like that, rather than doing something crazy like chatting with her online blackmailer. Heather kept up with the girls' discussions while sporadically answering his chat messages.

SpareRod2003: So are they enjoying the view?

NawtySubSlut1989: Pretty sure Keely got the whole show. Anna probably only saw my boob. My heart is pounding!

SpareRod2003: I love watching you be nervous. Slug down that glass of wine now, and ask for a refill.

NawtySubSlut1989: Getting me drunk, Sir?

SpareRod2003: Just calming your nerves, slut.

Keely had a sly smirk on her face when she told Heather to bring her glass over for more wine. Heather tried to stand as as modestly as she could, using one hand to hold down her hem so she didn't moon Anna. Keely didn't make it any easier, taking the glass to fill it, but then pulling it away when Heather tried to take the full glass back. Keely giggled watching Heather's breasts sway and jiggle as she tried to get the glass back, doing her best to hold her shirt hem down. Finally, Keely let Heather get her glass and she repeated the awkward process of sitting on the floor. Keely's big grin let her know that she had flashed her pussy again. At least this time she kept her boob inside her shirt.

SpareRod2003: That's so funny that she made you walk over there. Did Anna get a nice view of your ass?

NawtySubSlut1989: I don't think so, Sir, I held my hem down. I think Keely got a view of my boobs, though. She kept moving the glass so I couldn't get it back.

SpareRod2003: Oh well, that's too bad for Anna. I like Keely's sense of humor though. I think we should make sure she sees a bit more. I want you to drink half of that glass of wine right away. Then I want you to pinch each nipple through your shirt for a full five second count.

Heather almost choked on her wine. She manage to drink half the glass before she responded.

NawtySubSlut1989: I can't, Sir. They're right here! It'll be too obvious.

SpareRod2003: You worry too much. I'm sure you can do it subtly. You are allowed to cross your arms to cover what your fingers are doing, but make sure to pinch them hard. I want them to show clearly through that top.

NawtySubSlut1989: Please Sir. They already show so much. I'm scared.

SpareRod2003: Hmmm. Let me look here, I think I have Keely's and Anna's email addresses handy. I wonder how quickly they would get that video of you fantasizing about everything you would like them to do to you.

NawtySubSlut1989: Okay, I understand Sir. Please just give me some time. I'm very scared, particularly what Anna might do. Please don't push me too hard.

SpareRod2003: You have some time, slut, but don't test me too long.

Heather looked down at her breasts and pondered how she would do this. Her nipples were showing pretty clearly now, she thought, especially when they could slip right out through the arm holes. She set down her half full wine glass and engaged in the conversation with her roommates. She could feel her heart pounding as she crossed her arms in front of her boobs, trying to keep her attention on Keely's eyes as she position her right hand behind her left bicep, and pinched her nipple. She kept her eyes locked with Keely's and did her best to keep chatting as she bore down hard on her nipple and counted slowly in her head. One Mississippi, two Mississippi, three Mississippi... Keely's eyes darted down a couple times, clearly suspecting something was up. Her eyes widened slightly when Heather dropped her hand, and it was all Heather could do to not look down at her nipple. She was sure from Keely's reaction that it had to be more prominent through the thin fabric than ever. Heather knew for sure that if she looked down Keely would figure out Heather had done it on purpose.

She waited for almost five more minutes, talking and sipping her wine as casually as possible, before she had worked up enough courage to do her second nipple. Keely seemed to be paying even closer attention this time, and Heather was pretty sure she could see a smirk form once her rock hard right nipple was back in view Heather's face felt hot and flushed, and she was sure was going to start leaking profusely from her pussy.

SpareRod2003: That was acceptable. It seems like you need more wine to calm yourself down. Finish your glass and go get some more. But this time I want you to walk over and back on your knees. As an extra challenge, hold your glass in both hands at all times. You'll just have to hold it out for Keely to pour. That will keep you from adjusting your shirt in any way. You are not to touch your shirt under any circumstances, even when you sit back down.

Heather didn't think it was possible for her heart to beat any harder, but the image of kneeling in front of Keely, holding the glass out with both hands asking her to fill it, it almost made her chest explode. It was so submissive, there was no way Keely wouldn't pick up on it. Plus not holding the hem of her shirt down meant she would probably show most of her butt to Anna. Part of her wanted to plead and beg with him not to make her do it, but deep down part of her was getting incredibly turned on by the thought. This was what she had fantasized about wasn't it? To be able to do these kinky, dirty things while not having to take responsibility for it? This way she would be able to tell herself that she didn't have a choice, that he forced her to do it, and then just ride with the sensations. Suddenly, she knew she was going to go through with it, and anything else he told her to do tonight.

She swallowed the rest of the wine, got up onto her knees, and holding the glass in both hands in front of her, walked on her knees over to Keely. Her voice came out even softer and more submissive than she expected when she asked for some more wine. Keely had a quick burst of laughter, but quickly recovered and grabbed the wine bottle. Heather didn't dare turn around to see Anna's reaction, but she was pretty sure it was stunned silence.

Keely held up the wine bottle, and cocked an eyebrow at Heather expectantly. It was clear that Keely wanted to hold her glass out at arms length to get her wine. Heather's face turned yet a deeper shade of red as she held her arms out straight, holding the glass in both hands. Not satisfied, Keely moved the bottle a few inches back. Heather remembered her plan to go through this no matter what, and she bent at the waist, leaning forward to get the glass next the wine bottle. Her shirt fell away from her breasts as she bent forward, giving Keely an even better view of her nipples. Heather wasn't sure how much the hem of the shirt rose in back, but she imagined that about half her ass was in plain view. She kept her thighs pressed tight together to make sure she wasn't showing Anna her vagina or anus.

Keely filled Heather's wine glass very full, emptying the bottle. Heather had to focus on the glass as she walked on her knees back to her place next to Anna, just to be sure it didn't spill. The good news was focusing on that helped Heather not worry what was on show. When she finally was seated she took a chance and looked down at herself. It was even worse than she had feared. Her shirt had shifted and her left nipple was peeking out from the large arm hole. On top of that, the shirt had ridden up so her slit was clearly visible as she sat. It took every shred of willpower she had to not readjust the shirt to cover herself. Instead she just kept her thighs pressed together as tightly as she could, placed her left bicep where it hid her nipple from Anna, and tried to engage in the conversation as if everything were normal. Keely grabbed another bottle of wine, filling her own and Anna's. It wasn't lost on Heather that Keely had walked over to fill Anna's glass, but had made Heather come to get hers.