The Perils of Being Too Trusting

Author's Note: I'm not sure if I'd known three years ago how long it would take to get this story out if I would have started it at all. I have enjoyed my time with these characters though, and I hope you do too.

There is some rougher sex than what has happened up until now, plus more water sports. If you don't like those things, I advise you not to read.

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Brad and Heather Take Manhattan

Heather woke up to the quiet tune coming from her phone. She quickly silenced it, not wanting to wake Keely. She nuzzled her nose back into Keely's neck, and kissed her roommate's shoulders and back. Keely made a happy mewling sound and rolled onto her back, keeping her eyes closed, probably at least half asleep. Heather smiled to herself as Keely's voluptuous breast came into view; she had an idea how to wake her roommate. This was only the second time she had spent the night in Keely's bed, and it really only happened this time because Anna had spent the night at her boyfriend's, plus Heather was pushy about it. Part of why Heather had been so pushy is because after today Heather was pretty sure everything would be different, so she wanted to make this time special for Keely. Even though Heather still wouldn't let herself climax, she had done her best to make her roommate squeal and thrash through at least four loud orgasms the night before. Heather smiled at the thought that it was a night Keely would not soon forget. Heather slid her naked body down her roommate's, getting her mouth closer to that delicious nipple. When Heather had fallen asleep last night she honestly didn't know what she was going to do today, but now she was sure. And knowing what she was about to do, it only seemed right to wake Keely the best way she knew how, and make this morning as good for her as she could.

Heather latched her mouth onto Keely's perky left nipple, and sucked and nibbled on it until Keely let out a soft moan. Heather traced her hand over to caress Keely's right breast, massaging it and lightly teasing the nipple. Heather sucked harder on the left one, pulling more of Keely's ample breast into her mouth, and moved her hand down between Keely's thighs. Keely spread her legs to give Heather better access, and she slowly traced her fingers up and down Keely's sex. Soon Keely's labia began to spread, and Heather opened them wider, rubbing the lubricant all around. She diddled Keely's clit with her slick fingertips, and then pushed her middle finger inside. Keely let out a louder moan, and grabbed Heather's hair to pull Heather into her tit. Heather responded by gently biting Keely's nipple, and switching to two fingers in her roommate's pussy. Soon Keely was writhing in the bed, gyrating her hips.

Heather released Keely's nipple from her mouth, and slowly traced kisses down Keely's smooth belly, spending extra time licking her navel. Heather left lingering kisses all around her roommate's sex, spending some time running her tongue along her upper thighs before finally licking the wet, open vagina in front of her. Keely grabbed Heather's head and directed her licking, trying to get more stimulation to her clitoris. Heather did her best to draw it out, teasing and nipping at Keely's labia, licking all around to keep Keely from cumming too quickly. Eventually she could tell Keely could hold out no longer, and Heather began licking her friend's clit with everything she had. Keely began to flail about, and grunt fiercely. Suddenly, she pulled Heather's face hard against her crotch, and bucked spasmodically. Keely let out a high pitched moan as she came, the thrusts in her hips continuing uncontrollably for thirty seconds or more.

"Wow," Keely grinned when she regained her composure. "You have such a talented tongue, serving girl."

Heather giggled at the reference to being Keely's naked serving girl. It had started as a joke, but lately it seemed like sex slave might be a bit more accurate.

"So have you decided what you're going to do?" Keely suddenly turned serious. "Are you really going to see him? I'm not sure it's smart, I worry about you with some guy you've never met."

"I thought about it a bunch, and I'm going to go," Heather replied. "I have to try. I know it's hard to understand, but I have to go."

"If you didn't, if you told him to fuck off and just stayed here, then you know, then I might have to give you orgasms from time to time. It wouldn't be so bad."

"That's sweet," Heather giggled, "but I've made up my mind."

"Don't get me wrong," Keely had a wry smile, "I like it when you give me orgasms and I don't have to do jack shit. I just know things don't usually work that way. Well if I can't change your mind, you will at least do everything we talked about to stay safe, right?"

Heather could tell Keely was genuinely concerned. And honestly Heather was worried too. Meeting SpareRod in person had all kinds of risks. It seemed weird to be thinking somehow it was better to be blackmailed online than in person, but in a lot of ways she had become accustomed to their online relationship. She wasn't sure how it would work with him right in front of her. Not that Keely had any idea that Heather was being blackmailed, she just had the normal worries about Heather meeting someone that she had only ever talked to online.

"I'm sure. I have to know. The stuff we've done, it's been eye-opening to me. It's shown me a whole new world. I have no idea if it will actually work in person. But if I don't try, I'll be stuck always wondering. I'm only young once, I gotta give it a go."

"I get it. You go get him, and have a wild time. But you'll protect yourself, right? And no matter what, you know I'm here for you, right?"

"I will. And I know. I really appreciate it, you're the best friend ever. I don't know what I'd do without you."

Heather leaned in and gave Keely a peck on the lips, which turned into a lingering kiss, which turned into some serious making out, with hair grabbing, ass groping, and Keely tweaking Heather's nipple. Finally, Heather broke it off, saying she had to get ready.

"Well, if all my good friends kissed like that," Keely giggled, "I'd never get out of bed."

Heather showered, did her usual edging while finger fucking her ass before giving herself her enema, and put on the clothing she had picked out. She chose a tight fitting sleeveless undershirt cut to expose her taut belly, and the 10" pleated mini-skirt that he had made her buy but she had never worn. Her sandals with 3" heels completed her total slut look. The outfit was pretty much obscene, with her nipples clearly visible, her bare torso, and just a scrap of denim that didn't really cover her ass, but she wanted to make the right impression, to let him know that she was committed to doing this. She packed up her toiletries and the sex toys he wanted into a small rolling suitcase, tossed in a few pairs of high heeled shoes and sandals, and was ready to go.

"Holy fuck," Keely was still naked in bed when Heather came to say good-bye. "You look like a total slut."

"Good. Cuz that actually is the look I'm going for," Heather said dryly..

"Well then come here and kiss me goodbye, slut."

Heather was a bit taken aback by Keely using the same pet name as SpareRod did, and her pussy throbbed as Keely said it. She leaned over and gave Keely a kiss, caressing her cheek and stroking her shoulder. Heather's hand slipped down to Keely's breast, groping as much of it as she could fit in her small hand. Keely's hand wandered up Heather's thigh, squeezing her ass and tickling her freshly cleaned anus.

"Ahhh...," Heather panted when they broke, "I'd better go before I crawl back in bed."

"I'd be okay with that," Keely winked and squeezed Heather's bare ass.

"Mmmm.. tempting," Heather gave her roommate one last kiss, "but I gotta go. I'll stay safe and I'll be in touch."

Grabbing a lightweight black jacket to give her a microscopic bit of modesty, she got in her car and started the drive up to Denver. Her nerves were a jangle the whole drive. She knew this was completely crazy and risky, and that her roommate thought she was insane, but she stiffened her resolve to press on. She just had to do this, to see how far she could take it. And deep in her heart she knew that she could trust SpareRod. Even with all the blackmail and the ways he had tormented her, he had also helped her see what she really needed, and she just hoped that spending time with him in real life would take that to an even more amazing place.

She got to the airport before his plane landed, and was already standing where people came up from the train when he sent her a message that he was off the plane. She was getting lots of stares from people, mostly leers from men and mostly scowls from women, but she was so nervous that she ignored all that. It seemed like an eternity, but it only took about fifteen minutes for him to come up the escalator and walk towards her. Her heart was pounding so loud she could hear it throbbing in her ears, and her hands were trembling as she smiled at him. He looked good, even better in person. He was trim and well dressed in a blazer, pressed shirt, and slacks. His salt and pepper hair was close cropped, and he was tanner than she remembered, indicating he spent time outside during the summer.

"Hello slut," he said quietly as he stepped close to her.

He reached out and grabbed the back of her head, tilting it up and pulling her tight into him. He kissed her forcefully, pulling her hair a bit as he nibbled her lip and probed her mouth. She closed her eyes and took in the sensations. His strong grip, his musky smell, the coarse feeling of his starched shirt and wool trousers against her bare skin, it all swirled in her head. She kissed him back passionately. His other hand openly grabbed her breast, pinching the nipple firmly, pulling and twisting it through her thin shirt. Heather was overwhelmed at this point. She had been kissing Keely a lot lately and Keely was a really good kisser, but this was a completely different level. He was so strong, so forceful, it hit all of Heather's submissive buttons. She moaned into his mouth, and felt like her body was melting into his.

*

Brad knew that if this had the slightest chance of working that he had to establish control right away. He couldn't be his normal tentative self, always checking to be sure that she was still with him, always hesitating to see if she was happy with where things were going. The fact that Heather was here at all told him that on some level she wanted to be dominated. Even though he had fantasized about that often, he didn't have much experience in it, so he was going to have to stay focused to remain in charge.

Her soft moaning and the way she was grinding her pelvis against him told him that he was successful so far.

"Oh my God Sir," she panted when their kiss broke. "Holy fuck that is so good. I want so much to beg you, Sir, to pinch my nipple harder, but if you keep doing it here, I'm afraid I might actually cum right here."

He grabbed her other nipple through the thin undershirt, and pulled both of them up so she was on her tip-toes. She was still close enough to him and her jacket lapels hid a bit of what he was doing, but there was no denying that he was pulling her up by her nipples in the middle of an airport.

"No cumming... slut," he said softly with one last twist before he let her drop back down.

"Holy shit," Heather exhaled, "wow. That was... oh my God... that was... oh fuck, Sir. Thank you, Sir. May I ask what we do next?"

"First, let's walk from here," Brad said gently guiding her by the elbow away from the crowds and all the folks staring at them.

He looked over her outfit with approval. The skirt was fantastic, but he knew it was probably too scanty for his upcoming plans. He liked the top, and although part of him wanted to make her lose the jacket, he didn't want her to get arrested before they even started. They took an escalator up to the departure level, and he stood one step below her, both so it was easier to kiss her, and so he could grope her ass as they went. His hand slipped between her legs as they explored each other's mouths, and he was delighted to find she was soaking wet. He ran his finger back and forth a couple times to smear her lube back, and then pushed just one knuckle into her anus before they reached the top. He broke off the kiss and removed his finger right as they got off the escalator. She smiled at him, clearly embarrassed, and she seemed shocked into speechlessness. He reminded himself to stay in charge.

"I have a little surprise for you, pet. We're going on a trip," Brad held up his phone. "I have two first class tickets to New York that leave in just over two hours. I thought living it up in Manhattan would be a good way for us to get to know each other a little better."

Brad hoped his nervousness didn't show. He tried to play this cool, but it was all so risky. She could scream and call a cop. She could just say no and walk away. There were a thousand bad outcomes that could happen here, and only one good one. He felt very vulnerable, but he knew he needed to keep that hidden.

He could see the indecision play on Heather's face, and he got more worried the longer it went on. What was she going to do? He couldn't really guess, but he could tell she was conflicted as she thought about this.

"Okay," she finally said, "I am going to do this, to go with you and be your slutty sex slave and follow all your rules. I will do it all, no questions asked, but I have a few conditions right now before we can start."

Conditions? That was a surprise. Part of him wanted to scoff and remind her that she was the one being blackmailed here, but he could sense a steely resolve in her. Also, it wasn't like his hand was all that strong here, so he decided to give her some leeway.

"Okay slut," he emphasized the word slut which was probably a bit childish, "what are your conditions. I'm not agreeing mind you, I'm just intrigued."

"Before I can go anywhere with you, I need to take your picture, and a picture of your ID and send it to Keely. That way if anything happens to me, they'll know where to come find you. And, um, that's it. Once we've done that, I'm yours."

Brad pondered her demand. On the face of it, it terrified him since it would tip the power balance even more in her direction. She would know his full name, where he lived, she could do a lot of damage to his life. On more reflection though, he realized it probably didn't make that much difference. She could ruin his life right here by screaming for the police, and actually the longer this went on, the less believable it would be that he was really forcing her. So if this stretched the experience out, it was probably a good thing. But he still felt like he needed to regain the initiative.

"Well," he smiled, "let's start with the picture. Give me your jacket, and then find someone to take our picture together. I think Keely would like to have a picture of us as a couple."

Heather sighed, but gave him her jacket and her purse, and walked over to a trio of young men to ask if they could take their picture. The guys' eyes almost popped out of their head as they took in this petite woman with a barely there skirt and a cropped top sleeveless shirt that was just this side of see through. One of them managed to stammer that he would take the picture and followed her back. Brad set her jacket on her suitcase but handed her back her purse. He put his arm around her, resting his hand on her bare waist. As the guy got ready to take the picture, Brad brought his hand up, lifting her shirt until his hand was brushing the bare skin on the underside of her breast. Brad didn't think the guy's eyes could get any wider as he took a few pictures.

"Nice work," Brad whispered in her ear. "Now after you get your phone back, turn around and drop your purse. Be sure to bend at the waist when you pick it up."

Heather didn't say anything, but he heard a high pitched whine come from her before she walked to get her phone. She thanked the guy, turned around and took two steps before dropping her purse. She made a small exclamation, and bent over at the waist, literally mooning the three guys as she got her purse. The guy who had taken the picture literally let his jaw drop as he stared, while the other two started cracking up. Heather was obviously nervous, since she dropped her purse a second time. He could see that she was about to start laughing out loud by the time she got back to him, so he took her arm, helped her grab her stuff, and he thanked the guys as they walked away.

"That was soooo crazy Sir," Heather whispered to him. "We are so going to get busted. I hope you can handle whatever trouble we get into"

"Trouble is what we are going to be all about for the next few days," Brad said with more confidence than he felt. "Let's go over by those seats where it's quiet, and we'll finish up."

Brad decided to hand her both his passport and his driver's license. Hopefully that would help her trust him more, and it didn't really change things in terms of her leverage over him. She set them on the seat and took a couple pictures. While she sent the pictures to Keely, he emailed her the boarding pass for her flight to New York, telling her that she should send a copy of that to Keely as well. Just to be safe.

"Here you go Mr. Clark, Sir," Heather teased him as she handed back his things. "I have to say I'm kind of disappointed your name isn't really Rod. I told Keely that was your name."

"Well I still plan on using a rod on you, so it isn't 100% inaccurate," he teased back.

"I look forward to it," she gave him a wink.

It took a while, but Brad felt himself starting to relax. It was crazy, but this might actually work.

*

Heather's heart finally seemed to be slowing down. It was such a relief to have Brad (it was going to take her a while for her to get used to that name) take charge and run with her suggestion. She had thought that he might make a stink about letting her photograph his ID, but he hadn't just let her, but taken charge and made her send even more to Keely. Not only did it help her trust him more, but she also liked that he was asserting his control. That was what this was all about, after all.

"Okay slut," he said, "You need to know that I really like that outfit, it totally fits your slutty demeanor. But women have been kicked off of flights while wearing more than that, so I'm afraid you're going to have to change."

He pulled a piece of teal fabric out of his suitcase, and handed it to her. She fought back the temptation to inspect it - she knew she'd wear it no matter what it was. She started to tuck it in her purse.

"Okay, let me run to the restroom," Heather began, but he cut her off.

"Don't be ridiculous, slut. Just go behind those phones and do it. And be sure you get completely naked. No fair doing the skirt and then the top."

Heather didn't know why she thought he might take it easy on her. But the idea of being totally naked in public at an airport was crazy, even by their standards.

"Sir, I can't. Even if no one in here sees me, it's all windows back there, everyone driving by will see me, and there's gotta be security cameras."

"Naw," he replied lazily. "Those windows are tinted, they can't see in. And if you go quick no one in here will see. And don't worry about cameras, none of those guys are going to complain about seeing you naked. Now get going, or you might have to do it right here, and then you WILL be seen."

Heather puffed out her cheeks, but she knew where this was going. Just to make things easier, she kicked off her sandals before strutting back between the bank of phone booths and the window looking out on passengers being dropped off. She hoped he was right about them not being able to see in, and she hoped there were no cameras here no matter what he said. She took three deep breaths, and peeled off her shirt. It took less than a second more to remove the tiny skirt, and she was naked. Holy fuck, she was completely naked at the airport! It took a few seconds to figure out the teal piece of fabric was a tube dress. She looked up at him and he was grinning at her total exposure. Fortunately, pulling the dress over her head and adjusting it to cover her only took a little bit longer, and that quickly, it was over. She walked to him, and pretending to be much calmer than she felt, she handed over her skirt and top. The dress did actually cover quite a bit more than her prior outfit. The top part of the dress mostly lined up with the remnant of her tan lines, exposing only a bit of the pale tops of her boobs, and the sheath of fabric extended from there to her upper thigh. Weeks ago this would have felt scandalously short, but not anymore, since the hemline was almost an inch below her fingertips when she stood straight. Not quite as long as her work skirt, but still much more modest than what he frequently let her wear. The dress wasn't lined, but the fabric was heavy enough that people would have to look hard to notice the bumps of her nipples. She started to calm down as she got her sandals on and started walking with him.