The Perils of Being Too Trusting

"Careful, it looks like you could go over the edge pretty easily there. I'd hate to have to punish you for cumming without permission."

His eager smile made it clear that he would actually enjoy every second of punishing her. Heather, on the other hand, was pretty sure she would not, so she pulled her hand away and sat back down. He had her sit with her legs spread wide again, now showing him everything. She even had to pull up her cami, ensuring a completely unobstructed view, plus showing off her firm belly. Only her breasts had any kind of cover, but her rock hard nipples made sure that they weren't really hidden either. He told her that she was to keep playing with her pussy while they talked, but she could stop whenever she was worried that she might cum. The only catch was that if she wasn't playing with her pussy then she needed to pinch, flick, and twist her nipples as cruelly as she could stand. That way not only should it drive her back from the edge of orgasm, but it should motivate her to get back to teasing her pussy more quickly as her nipples got sore.

At least that was the idea, but the only flaw was that being forced to tweak and twist her nipples for him turned her on almost as much as rubbing her pussy, even if it did hurt a little. Actually it was more humiliating than painful. Humiliating first just in terms of punishing herself while he watched, but also because she was spending more time doing that than playing with her pussy, letting him know just how turned on she was. It let him know how far her buzzing, throbbing pussy could push her to go, what he could get her to do in this state.

She felt hot and flushed, and was squirming in her seat as they talked. She was getting to the point where she felt she would do almost anything to cum. The abuse to her nipples was no longer intense enough to really tamp down her pending orgasm. She was dying for him to make her rip off her camisole and be totally nude for him, but he just kept on talking through their fantasies. Finally, she told him that it wasn't working any more to have the fabric between her nipples and her fingers, and she asked if she might take off her last item of clothing. He smiled, commenting how he liked having her beg to get naked for him. She giggled and did an exaggerated performance of begging to take off her clothes since she was so hot. Suddenly she was struck with how sexy his smile was as he laughed out loud at her performance. When he regained composure he told her that she could certainly strip naked for him.

Once she was naked, she probably made it another 30 seconds of stroking her clit before she was right back at the edge of orgasm. She had to twist her nipples even more cruelly, even digging her thumbnails into the tender buds. She knew they would likely be sore all week after this abuse, but she was beyond caring. He suddenly seemed sympathetic to her plight.

"Hmm... you poor girl," he said without a trace of irony, "you seem really on fire right now, like you can barely keep from cumming. Would you like to have an orgasm now?"

"Oh fuck yes! Please... I need to cum... Please let me cum," she begged, beyond caring how pathetic that made her seem.

"Good girl. You're getting close to where I'll let you. You just have one more thing you have to do for me. It will be hard for you. Almost unbearable, but I promise you can do it, and once you have, you can have as many orgasms as you want, or maybe can stand."

Almost unbearable? What could he be talking about? This state she was in now, that was fucking unbearable. How bad could it be? She had to find relief, she would do almost anything, so she told him she was ready. Ready for anything.

"I want you to tell me your secrets. Rub your pussy for me and tell me your deep dark secrets. Tell me your fantasies that you won't admit to anyone, ones you've never even admitted to yourself. I know it turns you on to think about humiliating yourself of being humiliated. Now I want you to do it, tell me your deepest, most shocking fantasies. Think about how humiliating it will be for you to even say them out loud. Tell me those hidden things about you that no one should know.

She was stunned for a second. She could barely speak. God, what could she say? It was so personal, so invasive, she wasn't even sure if she could say anything out loud. Finally she ended up just blurting out some stuff that she could remember from his stories.

"I fantasize about being humiliated, about being forced to be the bad girl. I imagine being blackmailed into acting like a slut, into being publicly exposed," she started.

"I know that, that's why you contacted me in the first place. Go deeper, tell me your really kinky secrets"

"Oh God... I want to cum so bad... please just let me cum."

"C'mon nawtyTeeze... more naughty and less tease... tell me your secret fantasies."

Her mind was spinning as she tried to think of all the ideas she had ever masturbated to, the kinkier, the better. She started blurting out ideas and they just kept flowing. About how she wanted to be tied up and spanked, to be caught naked or even masturbating by a bunch of her friends and teased mercilessly, to be locked outside of her house with no clothes on. He pressed her to be dirtier. She said about how she liked to be fucked, and not just in her pussy. She talked about being held by the hair and fucked in the mouth, having some stranger ram his cock down her throat before filling her stomach with cum. She had never even come close to deep throating before, and she had only swallowed a half dozen times or so in her life. She didn't mind giving head, but the idea of swallowing a guy's bodily fluids was not enjoyable to her. But here she was talking about it and it was turning her on beyond measure.

This was followed with fantasies about being used in her ass, of being fucked long and hard in her rear hole. She actually liked anal better than she did giving blowjobs. At least there was no swallowing involved, and as long as the guy used lots of lube, did lots of prep work on her, and went very slowly, it almost always made for a hot night of sex. But her fantasies were not like that. She told him about being used roughly in her ass, about having guys fuck her lubed only by her spit and her pussy juice. About being tied face down on a coffee table at a party and having random strangers stop by and violate her ass with their cocks and other objects.

She started talking out having multiple guys fuck her, or girls joining in. While she had had a few one night stands with girls, and she had dated two guys simultaneously a couple times, she had definitely never been in a threesome. But the words kept tumbling out of her mouth, describing all combinations of three, four, five or even more people, men and women, using her in every orifice, and in every possible way.

Even though these fantasies were things she would never do in real life, talking about them as if they were real was driving her wild, making her thighs twitch. It was taking all her self-control not to cum. It wasn't so much that the situations she was describing were a turn-on in and of themselves, but more the liberating feeling she had of actually expressing these dark thoughts out loud. The feeling of losing all of her boundaries, of being forced to say these wicked and kinky things, it was all driving her to wilder and wilder extremes.

"C'mon nawty," he urged, "think about how much you want to cum. Tell me some things that are really nasty, your deeper secrets. Who do you really want to do those things to you?"

Heather's first response was famous people, like Ryan Gosling or Kristen Bell, but his laugh let he know that wasn't what he was looking for. She imagined ex-boyfriends, or friends from school, which he seemed to like better. She had no idea why she mentioned Keely, but he really seemed to like the idea of her being forced to lick her roommate's pussy. Soon she was telling him stories of her roommates blackmailing her, forcing her to be her slave. Of course she didn't give him their full names, but she was too rattled to make anything up so she just used first names. By this point she was so worked up that she couldn't touch her pussy at all, she just flicked her nipples as she talked, more turned on than she had ever been in her life.

That's probably why things took an even darker turn.

She began adding kinky detail after kinky detail, about how Keely and Anna would blackmail her into being their little sex slave. They would keep her naked all the time, make her sleep in a cage, have her wake them every morning by licking their pussies. She made a big perverted leap imagining that they wouldn't let her use the toilet, making her go pee in the backyard. She definitely did not have a pee fetish, and honestly had never even really thought about it, but at this point she was throwing up every crazy, kinky, perverted idea should could, hoping he would let her cum. This one seemed to get his interest, and he asked her how it would feel, to be totally exposed in the backyard, to be forced to urinate in front of her roommates or maybe even her neighbors. While the peeing part didn't really turn her on, imagining how humiliated she would be made her ache with arousal.

The next step in her descent into complete depravity was adding that her roommates would pee on her, eventually progressing to where they would pee directly in her mouth after she finished servicing them with her tongue every morning. This was totally crazy. She could barely stand to swallow a guy's jism, there was no way she would ever swallow urine! But it was so humiliating, and she just felt a deep need to explore ways she could be humiliated. He asked her more questions about this for a while, helping her revel in the erotic humiliation of the fantasy. He began prodding her to think of others who could humiliate her, real people in her life. He pushed her to think about what it would really feel like, if these people she knew treated her this way. The only thing she could think of was if it was someone she worked with, either from the restaurant where she waited tables, or maybe one of the dads of the kids she babysat. She opted for one of the dads, since she did work for one family, the O'Donnells, where the dad was quite handsome. She imagined him catching her masturbating in the basement after putting the kids down, and him disciplining and humiliating her for being such a horny slut. She imagined how he would strip her, spank her, use her in the ass and mouth, and then kick her out of the house totally naked.

To ratchet it up, Heather brought the mom into the story, describing how after Mrs O'Donnell finding out what happened, she would be jealous of Heather and torture her mercilessly. The story was getting kinkier and crueler, and Heather's head was swimming. She felt totally out of control, looking into his eyes and saying the most perverted, depraved things she had ever thought of in her life. But the experience was so heady, so wild, she never wanted it to stop. So she took one more step into degeneracy. She added their adolescent daughter into the story, describing even more cruel and outrageous things that would befall Heather at the girl's hands. Heather couldn't believe she was saying these things. It was sick, wrong, and immoral to even contemplate these kinds of illegal acts. She wasn't a pedophile, and things like this had never entered her mind before. And again it wasn't the actual scenarios that turned her on, it was the simple fact of how wrong it felt to be saying it out loud. How she was humiliating herself in front of her online master, that was the real turn on. He kept his eyes on her and prodded her to keep describing this depraved fantasy. Fortunately he sensed this had gone as far along its twisted course as it could, and he brought her back to the here and now.

"You look like you are in agony waiting to cum my pet. Would you like to cum now?"

"Oh God. More than anything, Sir. Please may I cum?"

"Begin to rub your pussy again, maybe I will let you."

"Please Sir, I can't even touch it right now. If I do, I will cum right away for sure. Please don't make me do anything if I can't cum right away."

"You can do it. Trust me. Start playing with her pussy."

Slowly, tentatively she began stroking her swollen lips and just barely teased her tender clit. Her body convulsed involuntarily the sensations were so intense, but she managed not to orgasm. Barely.

"Please Sir, please let me cum," she whimpered.

"You have been a very good girl nawtyteeze. You may cum for me now. Cum hard for me."

Just hearing the words come out of his mouth, the orgasm ripped her body. Her legs jerked and convulsed uncontrollably. Her back arched, and all the muscles in her body seemed to clench all at once. The orgasm hit her so hard and so fast that she was seared with pain. She knew she must look ridiculous as she flopped around in front of the camera, but she was so far gone, all she could focus on was the release that she desperately needed. Through the buzzing in her ears she could vaguely hear him urging her on, telling her to make it last as long as she could. She couldn't rub her clit anymore, it was too sensitive, but she alternated between squeezing her crotch and lightly slapping it, sending echoing jolts of pleasure through her body. She wasn't really sure if she had multiple orgasms, or just one very long one, but the experience was unlike anything she had ever had before. By the time it subsided, she was as relaxed and limp as a ragdoll. She finally looked up at him smiling at her.

"Well that looked like fun," he chuckled.

"Oh... my... fucking...God... Un-fucking-believable... I've never done... I've never had... that was fucking crazy... I can't believe how that felt so FUCKING GOOD!"

On one hand she was totally humiliated by all the things she had said to him, by the perverted kinky things that had come out of her mouth, but on the other hand she couldn't shake the earth shattering intensity the orgasm. They talked for a bit about how wild all this had been, and they agreed they should do it again. She tried to protest that she didn't think she could delve to the same depths of depravity, but he wouldn't commit that she would get what she wanted. After a few more minutes, they signed off. She thought briefly about asking whether or not he had gotten off, but he didn't volunteer anything, and she felt awkward asking so she let it go. She just barely managed to get dressed again before her roommates got home, and tried to act as normal as possible for the rest of the evening.

*

Brad pushed away from the desk in his hotel room, closing down the recording app that had stored the entirety of his and nawtyteeze's chat to the hard drive. His dick was so hard it was almost in pain. That had to have been one of the hottest experiences of his life. He had started off the day with truly low expectations, and now his mind was pretty much blown. Not only had that been crazily hot, and not only would it give him hours of spank material re-watching it over and over again, but it had also opened up all kinds of new possibilities.

He had been writing dirty stories and putting them on the internet for over five years now, but this was something totally new and different. When he started posting things online, he had immediately had several people email him, wanting to talk about his stories, or stories they would like, and all kinds of interesting propositions. Many came with pictures of naked women the authors claimed were of themselves. He was obviously very skeptical, just because it stretched credulity that women would send naked pictures of themselves to complete strangers as an opening email. He did always try to correspond with everyone who emailed him, just to see what else would come of it. Plus, whether the pictures were real or not, they were always very sexy and he enjoyed them no matter what. He would usually ask for some additional photos, suggesting certain poses which would lend more credibility to the idea that the author was the same as the girl in the pictures, but invariably that had never worked out. Somehow their camera was broken, there boyfriend had taken it, or some other story, but he never got any pictures, videos, or anything that led him to believe the photos were authentic.

In the few cases where the correspondence went back forth over longer periods of time, he had usually ended up using instant messaging too. Admittedly, every once in a while he would get an unsettling feeling that the woman he was chatting with was really some guy messing with his head, Brad usually exiled those thoughts quickly. Since this was all about exploring fantasy, he usually worked on suspending his disbelief, and enjoying the ride. That didn't stop him from asking for pictures, or to try video chat, it just never seemed to lead to anything beyond the occasional random image in his inbox. Not that he minded, since every once in a while the exchanges blossomed into very erotic dialogs that led to new story ideas, even if he had no idea what the other person looked like.

When nawtyteeze had first contacted him, he had figured it would play out about the same way as it always did. He had been pleasantly surprised how quickly she had engaged in conversation, and he enjoyed her creativity and enthusiasm for smut. His sense of things was that she was being honest about most things, but he knew it was not likely she was actually a 24 year old girl out exploring her fantasies of being a submissive. What were the odds that a girl like that would really want that with some 49 year old divorced guy?

Consequently, he had been completely surprised when nawtyteeze had agreed to a video chat, and had been very skeptical that it would really happen. The initial surprise of her actually showing up on the video chat had been quickly overtaken by the utter shock that she was not only really female, and really in her 20s, but she was really cute too. Maybe not supermodel hot or anything, but very cute, and with an awesome sexy body. Even if this was a one-time thing, he figured that this might be the crowning achievement of his adventures in writing erotica.

Now looking back at the session, his mind could barely take it all in. She had been so creative, so inventive in her perversion, he had felt like he barely had a role in the chat. All he had to do was give her some minor prodding every now and again, and she had exposed a kinky mind that was awe inspiring. Listening to her fantasies of her roommates abusing her had turned him on so much he had almost lost it right on the spot. The fantasies about the family where she babysat were not his cup of tea in terms of fantasy, but he had let her run with it. And watching her orgasm at the end, what a mind-blower! He had taken a risk by telling her to cum like that. If she had not cum right away it would have ruined his hold over her. But the speed and intensity of her orgasm was unlike anything he had ever seen.

And the more he thought about it, he realized the things she had said in this chat might lead him to a whole new level with nawtyteeze. He wasn't sure if he could do it, and if it went wrong the consequences would be very serious for him. But if he stayed strong, and played his cards right, the possibilities were beyond anything he could have ever hoped for.

He had a lot of preparation to do, and he could see that he had a lot of work ahead of him. But first he was going to replay that video and enjoy every minute of it.

*

Heather woke up the next morning feeing more satisfied than she had in a long time. The killer orgasm from the chat, plus several more overnight had put a perpetual smile on her face. Even the protests of pain from her nipples when she scraped them along her sheets rolling over were not enough to mute her smile. She did regret being quite so rough on her boobs, but it seemed an acceptable price to pay. A couple times she had had pangs of shame about the things she had said during the chat. It had felt a little awkward to hang out with Anna and Keely last night after having created fantasies of them dominating her, and she had no idea of how she could ever be normal around the O'Donnells again after her truly degenerate fantasy about them, but thankfully those thoughts faded quickly and she had enjoyed the evening reliving the experience in her mind, and masturbating frequently.