The Perils of Being Too Trusting Ch. 05

Heather was a little taken aback by her own words. SpareRod her boyfriend? It was crazy, but it was strange how her feelings had evolved over the past couple weeks. From being terrified and angry, to the liberated, sexual energy she was feeling tonight, it all made her head swim.

"Lucky guy," Keely twirled Heather's hair in her fingers. "Now I just fucking need a guy for me to come riding up. Oh well, till then I guess I'll just have my little serving girl keep me satisfied."

Heather felt relieved as they both laughed. She had worried a bit about her friendship with Keely, and didn't want what was going on with SpareRod to fuck that up. Heather was a bit nervous about how she might be used as Keely's serving girl, but so far it had all been astoundingly sexy, so she was just going to roll with it.

"Lights are out," Keely was looking at their house, "so Anna should be asleep. Let's see if we can sneak you in naked."

Heather thought it was funny that Keely was more concerned about their roommate seeing Heather naked inside the house than all the neighbors seeing her naked outside the house, but decided not to point that out. She did her best to walk casually next to Keely, and thankfully they were soon in Keely's bedroom. Once they were there, Keely flopped back on her bed.

"Oh serving girl, undress me for bed!" Keely used her mock imperious tone.

Heather knelt on the bed between Keely's legs and unfastened her shorts. Figuring if she was going to do this, she should do it right, she grabbed the waistband of the shorts between her teeth to pull them down. Keely lifted her ass off the bed, and Heather got them off. She kissed all around Keely's panties, on the upper thighs and along her flat belly, intentionally avoiding any contact with her pussy. Keely whimpered in frustration, but murmured her encouragement for Heather to keep going. Heather slowly unbuttoned Keely's blouse, kissing her skin as it was exposed. Heather trailed her lips up Keeley's smooth stomach, and around her voluptuous breasts along the cups of her bra. Heather licked and sucked as Keely quietly urged her on, saying how sexy all this was. Heather had to briefly pull her up into a sitting position to remove Keely's top and bra. Once Keely laid back down, Heather leaned over, sucking and kissing Keely's large breasts. She kissed them all over, intentionally avoiding the nipples, which given how big Keely's boobs were, took quite a while. Keely let out a moan of relief when Heather finally began sucking and nibbling on her engorged nipples.

Heather's hand slipped between Keely's thighs, and explored her wet slit while sucking hard on Keely's nipple and pulling her head away, stretching Keely's tit into a cone. Keely put a hand in her mouth to hold in any moan to make sure they didn't wake Anna. Heather slipped one finger, and then a second into Keely's pussy, pumping it in and out and using her thumb to bump Keely's clit.

"Oh fuck yeah," Keely whispered, "you kinky little serving girl. Bite my nipple more... yeah ... fuck me harder... oh yeah, keep fucking me like that... oh my fucking God that's so good."

Heather straddled Keely's muscular thigh, and grinding her own pussy against Keely's leg to get some stimulation while she focused most of her energy on pleasuring Keely. Keely kept her stream of quiet, whispered suggestions and encouragement running, which Heather found hot as fuck, knowing that she was getting Keely so worked up. Suddenly, Heather had an idea.

Hold on," Heather panted, "I'll be right back."

Heather ignored Keely's whines and ran to her room. A few seconds later she was back, plugging the wand vibrator into the wall. She had a giant grin on her face as she climbed back up onto Keely's bed.

"I'm gonna rock your world with this," Heather taunted, "but you'd better be sure to keep quiet."

Heather turned on the vibrator, and began teasing and playing with Keely. Heather just barely let it buzz one nipple while she sucked and nibbled on the other. Slowly she traced the vibrator down, around Keely's navel, and then circling her pussy. Heather straddled Keely's leg again, both to hold her legs apart, but also to let Heather grind her pussy against it. She used a couple fingers to spread Keely's nether lips and leaned down to kiss her clit. Heather licked up and down her labia, and thrust her tongue deep into Keely's pussy before going back to flicking her tongue across her clit. Keely continued to moan and used her hand in Heather's hair to keep her licking.

Finally Heather brought the head of the wand against Keely's pussy. Keely gasped in shock and flinched at the sensation, and this was just on a low setting. Heather smiled at the thought of what she was going to do to Keely. Heather moved the vibrator up and down Keely's slit while she leaned forward and whispered in Keely's ear how she was about to get fucked so hard, and how Heather was going to make her cum and cum. Keely was barely able to speak, and she just said yes and begged Heather to get on with it.

Heather moved back down to Keely's crotch, positioned the vibrator against her clit, and inserted first one, then two fingers into her sex. Keely wriggled in a sexy way as Heather kept the pressure from the vibrator right on Keely's clit. Heather pumped her fingers in and out of Keely's slippery pussy, whispering how she was going to love this, and how hard she was going to cum. Keely's back arched, and her legs stiffened, and Heather tried to judge how close her roommate was to orgasm. When Heather thought it was very close, she pulled the vibrator away and stopped moving her fingers inside of Keely's vagina. Keely whined and tried to grab the vibrator and pull Heather's hand deeper inside her, but Heather just giggled and moved her fingers very slowly until Keely visibly cooled off. Then she turned the vibrator up to medium, and repeated the process of getting Keely very close to orgasm.

This time when Heather pulled the vibrator away, Keely actually growled at her and grabbed Heather's hand. Heather was not to be rushed though, and she swatted Keely's hand away. Gradually Heather worked a third, and then all four fingers into Keely's well lubricated sex. She brought Keely to the edge again three more times, which she knew was probably pressing her luck. But she also knew how great orgasms were after a lot of edging. There was no way she could duplicate in one night the sensations she had after a week or more of edging, but she wanted to do a good job as a serving girl, and she wanted to rock Keely's world.

Finally, Heather decided it was time. She had never done anything like this before, but she knew she had small hands, and Keely's pussy was flowing like crazy, so she decided that she should try to fist her. She had read about it, and seen a video or two, but it would be her first time. She tucked her thumb against her fingers and slowly pressed into Keely's pussy. Heather turned the vibrator up one more notch, and gently coaxed her hand into her roommate. Keely writhed in pleasure, with a fist in her mouth to help her stay quiet. When Heather's hand finally slipped in past the knuckles, Keely gasped and clutched Heather's hand.

"Holy fuck," Keely whispered. "Gentle..."

Keely gyrated her hips against Heather's hand and the vibrator, holding Heather's wrist with both hands. Keely made just tiny motions, thrusting herself on Heather's hand and making guttural animal noises. Keely rocked back and forward, and Heather could see her eyes cross slightly. A loud squeal escaped Keely's mouth as a giant orgasm overwhelmed her. She quivered and trembled on Heather's hand while Heather continued to press the vibrator against Keely's clit. Keely pulled Heather's arm up so her hand pressed hard on the front wall of Keely's vagina, squeezing it against her clit and the vibrator. Another orgasm washed over her almost immediately, eliciting an even louder cry. Keely flopped and jerked for the better part of a minute until she pushed the vibrator away, saying it was too sensitive now. Heather gently eased her hand out of her friend.

"Oh... my... fucking... God... " Keely panted softly. "I had no idea you were that fucking talented. Shit, if I'd only known, I wouldn't have waited so long. Plus that thing! Fucking-A is it strong."

"Shhhh," Heather shushed, "Anna's a heavy sleeper, but you were pretty loud. I had no idea you were a screamer. She might be awake now."

"I couldn't help it. Look what you made me do, you're a naughty serving girl."

"Well," Heather teased, "you'll just have to spank me. But not now, that would definitely wake up Anna."

"You tease. Are you sure you don't wanna cheat and cum tonight. I feel a bit bad hogging all the fun to myself, and I'd love to see you wiggle on that thing."

Heather hesitated, but had to reluctantly decline. She had been through so much with SpareRod, and he would be able to tell if she was lying, so she had to stick with the plan.

"That's really tempting, but I can't. It's really fine, it's enough for me to have seen your face just now. You're cute when you're eyes are crossed."

"Fuuuuck!!," Keely sighed, "That was un-fucking-believable. Hope I really didn't wake Anna. She would definitely freak out a bit over this."

"Just in case," Heather whispered, "I should be getting back to my room. Unless you need something else before I go Miss?"

"No," Keely whispered in her imperious tone, "that will be all serving girl. Off to your quarters with you."

Heather gave her a light kiss, and padded back naked to her room. She set up her laptop to broadcast her sleeping naked, but SpareRod wasn't on and she was too tired to type an update. He'd probably be upset with her, but for now she just wanted to savor the experience of the evening. Whatever she needed to do to make him happy, she could deal with that tomorrow.

*

Brad looked at his clock and groaned silently. He didn't need to get up for another hour, but there was no way he was going to get any sleep. All he could think about was finding out how Heather had done at the party. Had he pushed her too far making her ask Keely for permission? Had Keely freaked out and rejected her? Had Keely gone too far, taking too much advantage? The scenarios kept bouncing around in his head. He cursed himself for being so conflicted, and got up to get dressed. A few minutes later he was jogging on his treadmill and trying to clear his head.

He knew his behavior was completely ridiculous. Pushing Heather to do wilder and wilder things, but then freaking out over it. But events always seemed to be overtaking him. The whole point in blackmailing Heather was to control her, to make her do perverted things at his bidding. But there were limits to what could be done just online without involving other people, so he kept bringing Keely into it. Heather's roommate seemed open minded and to be having fun with it, but Brad knew to keep doing this was incredibly risky. It could either slide into Keely convincing Heather she didn't need to do this and to call the FBI, or go the other direction with Heather and Keely taking off, and cutting Brad out of the picture. Either way, Brad was fucked. He kept thinking if there was a way to be there in person he'd have more options. He thought about just flying to Colorado and watching Heather from a distance, but it seemed really lame. Plus Heather knew what he looked like, and would probably notice him. He returned briefly to his fantasy of being with Heather in person, but that was way too risky, and he couldn't even entertain the idea.

He knew the the day was coming soon when something would have to give, and this whole adventure would fall apart. The only question was, would he have the guts to take it to the next level before it did?

*

Heather checked to make sure she had grabbed everything she needed out of the bag on her bicycle, and walked over to the small roadside building where the public restrooms were. Her stomach was churning from the adrenalin; this was the craziest thing she had done for him yet. And that was saying something after the stunt of a couple days ago. He had made her go out to a cafe, and then play blackjack with him over the video chat. That in itself wasn't that hard, it was how he made her dress and what he made her do that had made it difficult. She had been wearing a button-front dress with seven buttons, and had a set of seven anal beads up her ass. For each hand they played, if she won she was allowed to remove one bead from her rectum, if he won then she undid a button. The game was over when either the dress was all unbuttoned, or the beads completely out of her butt. Heather didn't know if he was a card shark or what, but he had seemed pretty confident, and it was no surprise the game ended with her dress completely undone and five beads hanging from her ass. Walking to the car with her dress fluttering open and the beads clearly visible swaying below her hem had been excruciatingly humiliating.

This afternoon's shenanigans promised to be even more extreme. She went into the bathroom and stripped in front of the sink, shivering momentarily at being naked, even though it was over 90 degrees out. She started with the black paint, and began painting her upper thighs. This was going to be very tough to explain if anyone came in, so she tried to move quickly. She wrapped a piece of masking tape around each thigh, almost halfway to her knees, and one around her hips. She smeared the heavy latex paint around, covering her thighs, her ass, and all of her crotch except for just on her pussy lips and asshole. Next she wrapped some tape around her waist above her navel, and around her biceps. She applied a bright yellow paint all over her chest and back, using a long handled applicator to get her back. A quick stripe of green around her biceps where the tape had been, and around her neck to look like a collar, and it was about as good as it was going to get. She stepped back to look in the mirror, and felt like she was going to faint. The idea was that from a distance it would look like she was wearing spandex cycling shorts and tank top, but looking at it now she felt that would only work at a distance of half a mile or more. She should have experimented more before doing this, it was guaranteed that no one would actually be fooled by this. The shape of her nipples were clear, even if the paint hid their color. Plus her boobs swayed and jiggled, showing that she had nothing covering them. Even with black paint covering her neatly trimmed tuft of pubic hair, it was still obviously pubic hair, and her slit was clearly visible below. She felt lightheaded from the fear, and was starting to panic when his voice from her phone brought her back to reality. He apparently had not been able to watch her apply the paint, and he wanted to see how she looked.

"Hold up your phone so I can see, slut. I can't wait to see how this goes."

"Holy fuck, Sir. This is the most fucking insane thing I've done. No one will be fooled by this."

Heather held up the phone and moved it around so he could see her from all angles.

"Well, it's pretty basic, but I think it should be sufficient. You'll just have to keep moving so no one gets too good a look."

"But Sir, if someone passes me they will have plenty of time to look, they'll know I'm naked for sure."

"So be sure to tell those people 'you're welcome.' Now get with it slut, get back on your bike and begin riding!"

Heather felt wobbly as she walked back to her bike, even with all the exposure she had had over the last few weeks, this felt extreme. If a State Trooper came along she would be stuck naked with no way to cover up. SpareRod had her pack her clothes in the bottom of her paniers, so there would be no quick way to get dressed again.

"Okay, you're almost ready," his glee from her suffering came through loud and clear. "Get out the vibrating egg and black butt plug and put those in before you start riding. Keep the egg on medium please."

"Fuck, Sir. Really???"

"If you're challenging me, maybe we should use some of the other toys I had you bring? The nipple clamps? The bright red butt plug?"

"Oh fuck, Sir, not that, I'm doing it." The idea of having a bright red plug in her ass visible to anyone passing her was more than Heather thought she could bear.

Fortunately he didn't insist, and instead made perverted comments while she lubed up the plug and slid it into her anus. A few weeks of regularly sticking things up her ass was making it a bit easier, but it still took effort to get it in, and she felt stretched and full once it was all the way in. At least this black plug wasn't too big, and it blended in with the black body paint. The vibrating egg went in easily, since her pussy had been gushing all morning. The low level vibrations from it made her horniness even more intense, but she doubted it would be enough to get her to orgasm. It had been so long since she had been allowed to climax, she would have thought any stimulation would make her cum, but sadly it wasn't to be.

She affixed her phone to the holder on her handlebars that would let him watch her as she rode, mounted her bike, and began riding on the small, twisty mountain road. It was mid-morning on a Tuesday, and thankfully she had seen very few other cyclists. On weekends this road was packed, and there were probably some people who rode it early before work, but it was blissfully quiet as she rode. She had to admit that the sun and wind felt great on her bare skin, and without thinking she thanked him for making her experience this, it was incredibly liberating to be naked out in nature. She had actually done this a couple times recently, expressed gratitude for what he was doing to her. She didn't know if she was experiencing some kind of Stockholm Syndrome or what, but she knew that without him she wouldn't have her regular naked serving girl episodes with Keely, or feel the wild exhilaration of riding her bike naked through the hills. He laughed when she thanked him, and he encouraged her to keep going.

Of course it wasn't all freedom and bliss. Soon she saw a group of riders coming down the hill towards her. He told her it would be fine, to just keep riding and not pay them any attention. Fortunately they were going fast coming down the hill, and they zipped by her without saying anything. She was pretty sure a couple of them did a double take, but she kept her eyes on her phone and kept pedalling.

Between the exertion climbing the hill and her increasing arousal from the vibrator and the movement of the butt plug as she rode, she was beginning to perspire. The paint was supposed to be waterproof, but if she got sweaty it might peel off her skin. Just one more thing to worry about. She took a sip from her water bottle and tried to think more of the sensations coming from her pussy and ass than about her paint coming off.

Soon she had something else to worry about; she heard a group of guys coming up the hill behind her. They were all in their racing outfits, and were gaining on her quickly. She started to panic, and babble to SpareRod, not knowing what to do. He told her to stay calm, and when they got close to her to pull over and slow down a bit so they would pass her quickly. She tried to follow the suggestion, but of course as they guys got up behind her they slowed down. Fortunately they only rode behind her for a few hundred yards, then they began to pass her, each guy taking an extended look at her clearly naked body as they passed her.

"Like your outfit," one said with only a trace of a leer.

"It's a dare from my boyfriend who's stationed overseas," Heather blurted out and pointed at her phone. She prayed that would keep them from overreacting.

"Lucky guy," another one of them laughed before speeding up and riding away from her.