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.