The Perils of Being Too Trusting

"Fuck! If this traffic goes any slower, I'll be going backwards!" Heather swore at no one in particular. She had just finished up her afternoon babysitting job, and the 45 minute drive home seemed to be taking forever. While stop and go traffic was making her antsy, it was just as likely that her persistent rubbing of her clit through her panties was the real culprit. While it felt fantastic, it was also driving her crazy; plus it was totally reckless. No one could have been more surprised than she was that she had her hand up under her skirt, rubbing her pussy through her damp panties, but that was just the beginning of how bizarre things were getting. In general, she had always been pretty tame and conservative when it came to sex, but it seemed her universe had exploded over the last few months.

It had started about six months after she graduated from college, after she had moved in with a couple college friends and started out into the real world. While she was making ends meet waiting tables and babysitting, she couldn't find anything in her chosen field, and it left her unfulfilled. It also frequently left her feeling incredibly horny. Her most recent fuck buddy had moved away after the end of school, and she hadn't gotten laid since graduation. She could no longer count how many times she had masturbated to "50 Shades of Gray" and eventually the excitement was completely gone from that story. She moved on to looking online for other stories that could get her worked up the same way, and had eventually found sites on the web with stories that made E.L. James' stories seem tamer than Mother Goose. There was one author in particular who seemed to hit on all her favorite aspects of a dirty story. Female submission, the heroine put in difficult and humiliating situation, and forced to behave like a... well like a slut. The stories gave her butterflies, and made her pussy damp every time she thought about them.

She spent months reading all of the stories, but once she had read them all over and over again she had that empty feeling again, and she found nothing new to get her going the same way. On a whim, she decided to contact the author to see if he was writing anymore. She made up a new email address to keep her identity secret, but with an eye towards piquing his interest. So nawtyteezegirl89 contacted SpareRod2003 to let him know how much she enjoyed his stories, and wondering if more were in the works. He responded about a week later, asking some specific questions about what she liked best, what she wanted more of, and also what she didn't like so much. She wasn't very experienced in this area, but she answered honestly, and was glad when he wrote her back, engaging her more in the stories. After about a month of emailing back and forth they started using instant messaging to chat rather than wait for emails. The immediacy of chat had sucked her in, and she had shared more of her fantasies with him. Soon they were making up stories together on chat, stories about girls being coerced into humiliating situations, being spanked for being naughty, being blackmailed to act like a slut. Actually, he made up most of the stories, she just gave little plot elements along the way. It wasn't as much that she couldn't come up with ideas, as that it was hard to do while she was masturbating.

After a month or so, he started asking about what she was doing while they were making up these stories, and she admitted she was playing with herself. He pressed her for details, and before she knew it, he was guiding the way she masturbated. As she got closer to orgasm, he kept moderating her rubbing so she stayed at the edge without going over, and he urged her to divulge her fantasies to him. She blurted out something about being tied up naked in public, and he told her a story about her being tied up like that and discovered by a crowd that groped, spanked, and humiliated her. He kept the story going until she had an earthshattering orgasm.

The experience had rocked Heather's world way more that she could have imagined. She had never masturbated in front of anyone, and even though he couldn't see her, and didn't even know if she was really doing it, it still felt intensely personal. On top of that, the orgasm was monumental. While she was a little bit embarrassed to have been sexting like some adolescent, she had to admit she couldn't wait to do it again.

It was only a matter of time before they reached the point where she and SpareRod would chat almost every day, and often more than once a day. Sometimes while she was on break from her waitressing job, sometimes after the kids had gone down when she was babysitting, and often from home. They would frequently fantasize about a fictional character they had made up named Elaine, and the travails they put her through. Other times he would ask Heather what she was doing, and he would command her do an escalating set of kinky tasks. Many she would actually do (strip naked in her bedroom, masturbate in her car, masturbate with a finger up her asshole), a few she fibbed and said she did when she actually didn't (get naked in her living room with the blinds open, step naked into her backyard), and a few that she had to say she just couldn't do (take her underwear off under her clothes in a public place, get totally naked in her car). Even though those things turned her on like crazy, she just knew there was no way she could ever do them in real life.

The one thing she never lied about was her orgasms. It seemed funny when she thought about it, since she was lying about a number of things (where she lived, what her name was, where she might get undressed) but the orgasms were too good, too meaningful to sully them. So she would always drop hints early in the conversation if she was looking to cum, and he had very quickly picked up that she was only going to cum when she was in the mood. She never even had to tell him, he figured it out on his own, and he never questioned it or badgered her. It was one of the things she liked about him, that he never pried too deep about her, and beyond an open offer that she could send him a picture of herself if she wanted, he never pestered her for anything. So it caught her a little off guard when about a week ago he had asked if she would be willing to do a video chat with him. Again, he made it clear there was no pressure, just that he thought it would be fun. Even more surprising to her was when she had answered "maybe" instead of "no." Part of it was she didn't want to disappoint him. While it wasn't like he was her boyfriend or anything, she had grown incredibly fond of him, and felt very close to him. It was crazy – she didn't know his name, he was way older than her, and he lived out in California. But chatting with him had kind of taken over her life, and she felt like she really connected with him. She trusted him.

Of course the other reason she hadn't ruled out a video chat was that the idea deeply excited her. What if he talked her into getting naked? Could she really do it? Could she show off like that? Maybe even masturbate with him watching? What else would he want her to do? She imagined watching his eyes on the screen as she followed his commands, stripping and playing with herself. The whole idea seemed deliciously wicked, and she found herself imagining it more and more as she masturbated.

But the idea of doing it in real life also terrified her horribly. Every time she chatted online with him her stomach did flip flops. Soon their chats ended up as a role play of what a video chat might be like. She loved thinking about how it would feel if she was really doing it, and not just a fantasy. After a while, he bumped up the pressure by having her spend most of the chats right on the edge of orgasm, but then stopping and forbidding her from cumming. To make it worse, he told her that she shouldn't cum between chats as well. While there was nothing to keep her from cheating, she was intrigued by the concept of how it would feel bringing herself to the edge of cumming but holding back several times over the course of days.

The answer was that it would feel like she was going totally fucking insane. It was now over 9 days since she had had an orgasm, even though she had been masturbating right to the edge while chatting with SpareRod at least once every day, and often two or three times. It seemed like her pussy was tingling all the time. She was almost always wet, and had to change her panties frequently, especially when he made her rub her clit through them. After about six days, she had started playing with her pussy almost spontaneously, like she was now in her car. She hadn't started rubbing herself in public like a total pervert, thank God. At least she hadn't yet, although doing it under her skirt behind the tinted windows of her car was coming very close.

As she had become antsier and more distracted by her buzzing clit, the idea of the video chat seemed more and more reasonable. It was actually kind of scary that just a week and a half of no orgasms had her seriously considering doing something that she normally wouldn't. God knew where this kind of thing could lead in the future.

Finally, she had asked him if they could really do it. It was the scariest thing Heather had ever done. Her stomach was turning flips while she was trying to work up the courage to ask, and then as soon as she had, she was terrified. How could she have done that? Would she be able to follow through? To her surprise he didn't say yes right away, and instead asked questions about what she imagined it would be like, and before she knew it he had her at the edge of orgasm again imagining him watching her as he commanded her. By that time she would have done most anything to get him on the video right then and there, but he was on his phone at an airport, so they decided to try the next day. He told her that she was to play with herself at every possible moment over the next 24 hours, but under no circumstances was she allowed to orgasm.

So here she was, rushing home to have online sex with some stranger, trying to subtly reach under her skirt and tease her clit while she drove. If she hadn't been so horny she could cry, the whole thing would be laughable. Finally, she got to the small rental bungalow she shared with her roommates. She prayed to God things hadn't gone off plan with Anna or Keely. This just wouldn't work if they were home. Thankfully, the house was empty and she rushed to her bedroom to get ready. She liked her outfit of a sheer teal blouse over a black camisole and a floral skirt that came to just above her knees. Underneath was a very pretty turquoise bra and panty set. It was a little dressed up for babysitting, but now she thought showed her off just right. Pretty and a little bit sexy, but not slutty. She pulled her hair out of its ponytail, allowing it to drape over her shoulders, almost to her breasts. She spent a few minutes touching up her makeup to go from her everyday mode to a hot date mode, and before she knew it, it was time.

She opened her laptop, started the video chat program, and waited for him to join. She felt that since he was the Dominant, it only seemed right that she be waiting for him. Thankfully he was on within a few minutes, since she wasn't sure how long she could sit there without chickening out. As soon as his face appeared, she felt like her brain completely froze and she was struck speechless. On the good side, he was more handsome than she had really expected. He was older, maybe early forties with close trimmed salt and pepper hair, but he looked trim and fit. And at least from what she could see of his button down shirt and reasonably stylish glasses, he appeared to have an acceptable fashion sense and had put some effort into dressing nice for their "date." The problem was the weirdness of what they were doing hit her like a ton of bricks as soon as he connected, and she felt awkward as hell.

Fortunately he jumped in and started talking right away, relieving her of the need to think for a minute or two. He complimented her on how nice she looked, and even made her step back so he could see her skirt. Heather felt herself blushing, but was inwardly pleased by his wolf whistle as she pirouetted for him. They talked for a little while about how her nannying job had gone that day, about the traffic on the drive, about the weather in Colorado, about how they were both glad that the other one wasn't really a 300 pound high school kid living in his Mom's basement, and anything other than what they were about to do. Within minutes she found herself relaxing, even smiling and giggling as they talked. He was witty and kind, his smile was contagious, and she was relieved that this was going every bit as well as their IM chats had.

After a few minutes, he did start to steer the conversation towards sex. He asked how well she had done on her assignment to keep playing with herself, and she told him that she had been working at it, even doing it in her car.

"Well, I'd be more impressed if you had done it with your window open instead behind tinted glass," he winked, "but I suppose it does show you've come a long way."

Heather rolled her eyes and stuck her tongue out at him.

"So does that mean you don't have any panties on under that pretty skirt?"

"Oh God, no. That would have been too crazy. I kept them on and rubbed myself through them. And stop making those faces at me - I did the best I could. You said yourself I'm making progress!"

"Did I say that? I don't know what came over me," he teased. "So what kind of panties are they? How did they feel on your clit? It must be sensitive now with all that playing and no relief."

Holy fuck, Heather thought, it's really starting. If she was ever going to back out, this was the time. She thought briefly about just disconnecting and never communicating with him again, but she knew she wouldn't do that. She wanted this, and she knew she wanted to do it with him. She liked him and trusted him, and knew this was the right thing to do.

"They're satin. It feels really smooth when I rub it," she clenched her legs together just thinking about it.

"Don't you want to show them to me?"

Although it was phrased as a request, it was clear that it was anything but. This was his way of being polite, but she knew he was absolutely serious about this. Keeping her legs together, and unable to maintain eye contact with him, she looked down as she slowly pulled up her skirt.

"Good girl. I could see them a little better if you lifted the skirt up a bit higher"

It was ridiculous how being called a good girl elated her. It shouldn't be that easy, she thought. No matter though, it pleased her so much that she pulled the skirt up so he could see her panties from waist to crotch..

"Very good. Why don't you tuck the skirt into its front, so you don't have to worry about holding it."

Like she was actually worried about that! But she liked doing what he wanted, so she tucked it in. Their conversation resumed, making ups some more stories of tribulations for Elaine, and they both acted like Heather wasn't sitting there with her panties on display for him. A while later he asked to see her camisole, and it wasn't long before she was taking off her blouse as well. He complimented her both on the camisole, and on what he referred to as her "rockin' body." The compliment made her smile. She had always been self-conscious about her body; she always felt she was too skinny at 93 lbs. She was only 4' 11", so that wasn't a ridiculously low weight for her, but she wasn't the curvy kind of girl that seemed to get guys attention. Seeing him so pleased to peek at her body was thrilling to her.

The story they were making up about Elaine, which involved her Master taking her to strip club, kept getting hotter and more explicit. Heather's thighs kept bouncing together as she got more excited, and a few times she stroked her exposed thighs.

"You seem pretty excited. Wouldn't it feel better if you rubbed your pussy through your panties?"

"Okay. I guess. Mmmmm.... Shit that feels good. Now I'm just worried I'm gonna cum."

"No cumming," he was quite stern. "You are allowed to stop if you might cum, but I think you can gently stroke it and be safe enough."

Easy for him to say! Nonetheless, she began to trace her finger up and down her slit through the smooth material of the panties, occasionally swirling it around her little button. He made her keep her legs spread very wide as she did it, and it surprised her how humiliating it felt to be holding her thighs as wide as she could and rubbing the crotch of her panties. She wasn't showing any more that she would show in a bikini if she sat crisscross-applesauce, and she was barely grazing the gusset of her panties with a fingernail. What made it different was how he was watching her, and she was doing it because he told her to. That changed everything. She found herself staring into his blue eyes, her adrenaline rushing at the idea of being watched, and listening to his words. She imagined what it would be like to be Elaine, to be forced to join the strippers on stage, to pay for a lap-dance, or to have to service their pussies with her mouth. It was all a crazy fantasy, but it was all so erotic. Combined with him really watching her, it was getting her very hot and bothered.

"You're looking a little warm there," he interrupted. "Wouldn't you feel better if you took your bra off?"

She giggled at the way he made it sound like a question. She knew she couldn't refuse him; she didn't even want to. She made a sexy show of removing the bra from under the camisole, sliding off one shoulder strap and then the other, followed by turning her back to him as she shimmied it down under the cami and unclasped it. She continued to tease him by keeping her arm covering her breasts as she turned back to face him. He scowled at her, making her laugh out loud before lowering her arms. Her breasts were not large, (nothing about her was large) but she had often been told her B cups seemed big on her tiny frame. She was self-conscious about not wearing a bra, not because her breasts really needed support (they were definitely perky), but because her nipples were very prominent, and would show through most coverings. She was extremely excited right now, and the cami was light colored and almost sheer, so it really did nothing to hide the shape and color of her achingly hard nipples. He leered at them and complimented them profusely, which made Heather feel warm and squishy inside.

After ogling her for a bit, he decided he wasn't sure her nipples were as hard and prominent as they could be, so he made her tease and tweak them to see if they would stand up any more. Heather was pretty positive that they looked exactly the same after a few minutes of pinching and teasing through the fabric, but the experience left her flushed and breathing hard.

The story of Elaine was getting very kinky now, and Heather was making a point to show off and tease him with her body as he elaborated the fantasy. He finally asked her to untuck her skirt, and remove her panties. This left her feeling exposed in just the camisole and the skirt, but she wasn't actually showing anything. They went on a little further in the story, and she started slipping her hand up under her skirt to play with herself. Finally the moment of truth arrived, and he had her take off her skirt.

"Ahhh... shaved... very sexy," he seemed pleased as she stepped out of the skirt.

"No, waxed," she smiled. She had kept herself totally bare almost since she started growing hair there. "It keeps it much smoother." She rubbed her hand along her pussy lips to illustrate the point. Just that gentle caress got her to bite her lower lip and rock her hips slightly.