The Perils of Being Too Trusting Ch. 04

It took less than a few minutes he felt the compulsion to look at some pictures or video of Heather again. He knew this was a bad sign, and he wondered at what was happening to him. He was about twice her age, but he was acting like a love struck teenager. He was distracted all the time, both thinking about new games they could play, but more and more what it would be like to meet in person. For the first time since the end of his marriage, he felt he had found a person with whom he could be himself. Really for the first time ever, becuase he sure hadn't been able to do that with his ex-wife. For the thousandth time he wondered what would have happened if instead of trying to blackmail the poor girl, he had just kept up video chatting and exploring their fantasies together. He daydreamed about how they would have developed a real relationship, still exploring all the kinky submission activities that clearly aroused them both.

Brad mentally kicked himself, and resolved to stop thinking about what might have happened. It was all in the past now, and there was no way to change it. It wasn't like this was going badly, he was having a ton of fun with Heather, and his time would be better spent thinking up new things he could make her do, rather than moping about what might have been. He pulled his phone back out and started writing notes on new stunts he could make her do, and punishments he should dole out. She had forgotten to strip in front of Keely last night, so he would have to be sure to deal with that. Given that he had taken on the role of blackmailer, it wouldn't do to let her think that he was going soft on her.

But he couldn't stop from wondering how it would be if things were different.

*

Heather marveled at how much better she had gotten at spanking herself. The swats she was giving herself hurt like a motherfucker, and if her mouth hadn't been stuffed with Keely's panties she would have been screaming like crazy.

"Okay," SpareRod said, "that's good for round one. You are doing much better, I like how pink your tits have turned, and it looked like you really walloped your cunt with those last few."

Heather grunted in agreement on that. She wanted to do a good job, plus part of her was curious to see how much she could really dish out to herself. She had definitely put her arm into smacking her pussy with the cooking spoon with full force. She had played with herself between each swat too, doing her best to open her pussy so her clit would be fully exposed. The feeling on her clit was indescribable. It hurt for sure, but there was more than that. It was almost like a direct electrical shock to her brain, making her body convulse for just a second. The thing was, the pain receded quickly, and it left behind the most wonderful tingly, squishy feeling, and playing with her now super-sensitive clit was really getting her going.

"I think that's enough of rubbing yourself, you little slut," he chided her. "You still have two more rounds of spanking to do. Same as this last round, 50 swats to your ass, 20 to each tit, five to each nipple, and then 20 on your clit."

Heather nodded, and grunted through the panties in her mouth. She got up to kneel facing away from her computer so he could watch her thrash her own ass, when he added a new challenge.

"Before you get started, let's ramp things up a bit. Go get the medium one from the pack of butt plugs you bought."

Heather was not looking forward to that plug. She had used the smallest one a few times now, and it wasn't too uncomfortable. Actually it gave her an arousingly full sensation when he had made her use it. But the next one up was quite a bit bigger, and she worried that it would almost certainly hurt a bit.

She was right, even with plenty of lube, and going slow the plug still burned her ass as she pushed it into her rectum. Thankfully the pain faded quickly once the widest part was fully inside her, and the butt plug was securely lodged in her ass. She resumed her kneeling position, sticking her ass in the camera, her knees spread wide so her vagina and the red base of the butt plug were clearly visible. She began walloping her ass with the cooking spoon, whining and squealing after every hit. Her ass was still quite sore from her first round, but she did her best to not flinch, and really hit her ass. She was so focused on being good for him, she didn't hear the lock on the door, and didn't notice the front door opening until Keely was standing in the living room. She just stood there for several seconds with her jaw dropped wide open, staring in turn at Heather's red butt, the plug up her ass, and the computer. Heather could only imagine what was running through Keely's mind.

"Oh wow," Keely was clearly very embarrassed. "Heather I didn't mean to... holy shit... I'm really sorry... I forgot my phone... I'll just grab it and get the fuck out... aaahhh fuck!"

Heather closed the laptop, and spit out the panties, and tried to explain herself.

"Keely, I'm so sorry. I thought I'd be all alone today. Please don't be mad, I didn't know..."

"Ohhh," Keely seemed genuinely concerned, "Don't worry, we're all adults, you're allowed to have your...uhhhh... your fun.. or whatever... wait... is that MY underwear?"

'Uhhhm... yes?" Heather answered uncertainly.

"Oh... oh my God," Keely sighed. "But well, I think they're yours now."

Keely giggled at that, and she didn't really seem upset, but she made it clear she did have to get back to work. She rushed to her bedroom to grab her phone

"Nice buttplug, by the way," Keely laughed as she came back out and opened the front door. "You are one kinky biyotch. And we are so going to need to talk tonight. But I really gotta run. I'd say have a fun afternoon, but it looks like you got that covered."

With a final chuckle, Keely walked out the door, leaving Heather, naked, stuffed, and very embarrassed on her living room floor. She sat back on the floor, totally humiliated, and unsure what to do next. Suddenly, she remembered SpareRod, and the fact that she had shut him down unexpectedly.

"Holy shit!" SpareRod almost shouted when she got him back on. "Keely caught you? Are you alright? What did you do? What did you say?"

It took Heather several minutes to calm down to where she could even talk, but finally she walked him through the last few humiliating minutes. She embarrassed herself all over again by having to repeat everything, even Keely's teasing about the panties and the buttplug.

"So she didn't seem upset?" he seemed surprised. "That's interesting. So what are you going to tell her when she comes back."

"Oh my God, Sir," Heather was near panic, "I don't know. I'm really nervous about this. She saw everything Sir."

"Okay, calm down Heather, it's going to be okay. Remember my rule, never panic. Just stay calm and I'll take care of you. Good girl, just keep breathing. I have an idea, and it won't be so bad."

*

Heather looked over at Keely as the two of them walked around the park near their house. Heather thought back to SpareRod's assurances and cursed him. Easy for him to say it wouldn't be too bad, he wasn't here being grilled by a friend over acting like a pervert. To be fair, Keely wasn't really grilling her, she seemed genuinely concerned. She wasn't upset or anything, but she did seem very intent on getting some answers. Heather looked over at her roommate, who glanced at Heather expectantly as they walked. Heather guessed the one bright spot was that Keely had suggested the walk, so they didn't have to have this conversation in front of Anna.

"Well," Keely repeated her question, "are you going to tell me what's up with you?"

"Okay," Heather screwed up her courage, and began to tell Keely the tale she and SpareRod had constructed this afternoon. "I... uhm... I met this guy online... and we've kinda started a relationship. Uhhm... kind of a different relationship."

She and SpareRod had worked out that Heather should present to Keely that she had an online boyfriend, and they were exploring a BDSM lifestyle. It woudn't do to tell the truth of how and why SpareRod was blackmailing her, so an online S&M relationship with "Rod" seemed like the most believable story they could come up with.

"You're shitting me! You were doing that with some random guy online?"

"No! No fucking way. Not some random guy," Heather was genuinely offended that Keely would think that. "He's really... he's really great. We've been chatting for months before this. We just took it to the... uhm... the next level a week or so ago."

"And the next level involves him having you beat yourself and steal my underwear?"

Heather couldn't see Keely's face in the dusk, but she could tell from her tone that while she sounded like she was being flip, she was also concerned about Heather.

"Well honestly," Heather replied sheepishly, "while gagging myself with your panties was his idea, the spanking part was what I wanted to do."

"You wanted to spank yourself on camera for some guy you never met? A guy who could be a complete psycho? For a bit I thought maybe you had become some kind of a cam whore and were getting paid for it, but you're doing it for this sleazebag all for free?"

"He's not a sleazebag! He's a decent guy, and probably more important, he's the first person that I ever opened up to about this side of me... that I kind of get off on..."

"Spanking yourself?" Keely asked wryly.

"More than that," Heather felt like she needed to come clean. "I get off on being... uhm... being a bit submissive."

Heather felt like she was going to die of shame. But she was too far in now, and Keely was one of her best friends. She felt like she needed to talk about it.

"This is so hard to say Keely. I get a rush from doing things that are a bit humiliating or embarrassing. I know how this looks, and I understand why you're saying what you're saying, but he's not a sleazebag. He's made me feel good, like I'm not a freak. Actually he makes me feel like I'm really special."

Heather trailed off, it seemed weird defending the guy who was blackmailing her. Even weirder, everything she had just said was true. She was totally off-script now from what they had planned, but it felt good to say that out loud. She was not glad about being blackmailed, but she couldn't deny that things he was making her do were things she had dreamed about but had never dared to do.

"Oh Heather," Keely smiled, "I don't think you're a freak. A little reckless maybe. And definitely very sexy. And well maybe a bit freaky, but I mean that in the best possible way."

Heather laughed, relieved that Keely was being cool about this.

"So," Keely asked a bit tentatively, "who's idea was the naked serving girl?"

"That," Heather giggled, "was probably joint effort. I guess it was his idea, but it was kind of fun. I gotta say though that making me do your laundry was NOT that sexy. At least not until he told me to do it naked with your panties in my mouth."

"Seriously," Keely laughed out loud, "you did that?!? Just because he told you to?"

"Uhhhm... yeah," Heather answered a bit sheepishly, "I told you, I kinda like being told to do stuff like that."

"Sooooo," Keely seemed a bit nervous, "if I... uhm... if I told you to walk the rest of the way home bottomless, what would you do?"

Heather acted before she could think too much about the consequences, unzipping her skirt and stepping out of it right there in the middle of the park. It was the skirt she'd worn on her babysitting job, one of her longest ones left at 16", but SpareRod had made her get rid of her underwear, so she was left in only a tight t-shirt that ended just above her navel.

"Hoooooly fuck," Keely said softly, "I don't know why I thought you might chicken out. Aren't you scared?"

"Terrified," Heather answered honestly. "Can we go home now? I really don't want to get caught again today."

"In a second," Keely got a mysterious smile on her face. "I have one more addition."

Keely looked around to to make sure the park was still empty, unbuttoned her shorts, and peeled both them and her panties off. Heather was absolutely shocked, she hadn't expected Keely to get bottomless with her, it didn't seem like Keely's thing. It turned out it wasn't, since Keely quickly pulled the shorts back on, and then stood in front of Heather.

"Open your mouth serving girl," Keely commanded.

Heather's heart was pounding, and her pussy throbbed as she realized what Keely was going to do. Submissively she opened her mouth and let Keely stuff her panties into Heather's mouth. Heather felt so dirty and kinky just standing there as her roommate slowly poked her panties in with one finger. It was all Heather could do to not diddle herself on the spot.

"Mmmm..." Keely sighed as she pulled her finger out of Heather's mouth and traced it down Heather's chin and neck, "that's very good. I kinda like that too. Okay, now we can go home. I don't know how we'll get around Anna with you dressed like that, but I'm sure we'll come up with something. Cuz there's no way I'm giving you this skirt back tonight. In fact, I'm pretty sure you'll end up wearing less, so I can have my naked serving girl again. So let's get going."

Keely accentuated the command with a firm swat to Heather's bare ass. Heather's knees wobbled at the sensation, her nerves a jumbled mess. Part of her was in total bliss in this situation, but part of her couldn't stop worrying what she was getting herself into.

*

Brad checked his phone for the 20th time in the last five minutes. Still no word from Heather. The last message he had from her was when she'd returned home from her babysitting job and was about to go into the house. He had been pretty confident that the story they'd put together would satisfy Keely and keep Heather from revealing too much about what was going on. Brad didn't think Heather would say any more than that, since it would lead to Keely finding out about what Heather had said in the video.

But now it had been three hours, and Brad was getting a bit agitated. Had Heather come clean, and Keely talked her into calling the police? Or had it gone the other way, and Heather was now doing something with Keely and he was frozen out? The idea of Heather having to service Keely turned him on to no end, but he'd always planned that he would be in control if that ever happened. Now it seemed like things were moving out of his control. He'd have to think of a way to get back in charge of the situation, but with Keely being an independent actor, that was easier said than done.

He checked his phone again, cursing at it when there was no update. He decided to shut it off and go for a late evening run to clear his head. There really wasn't anything else he could do. He just had to trust that he would find a way to get back on top of things.