Dan's New Life 01: Mistakes

Another message came through. "Why would I do that? Krista's licking my wet pussy right now, and we want you to help us play. So I'm going to see how far I can push you. Just like we did this weekend. Start touching yourself, but keep it very slow." Dan looked at the tiny black iris of his phone's camera with pleading eyes, but quickly realized there was no point in resisting, and began to lightly play with his cock, the image of Lexie, dangling her creamy, pale thighs over Krista's bronze shoulders as Lexie watched and texted him, plaguing his thoughts.

Within a minute, Dan felt himself begin to approach the edge of orgasm: despite the very slightest of touches that he was giving himself, the pulsing against his anus was driving him wild. As this feeling grew and grew in intensity, he suddenly became very aware again of where he was, and what could happen if he lost control. He dropped his hands away from his cock, trying to calm down, and was instantly brought to his knees by another sudden increase in power from the toy inside of him, forcing him to clench his lower belly desperately to hold back an impending orgasm.

"I didn't tell you to stop touching yourself, did I Daniel?" read the message that came through as Dan struggled back to his feet, and the instant his hands returned to his cock, the vibrations lessened to a survivable level once more. "Please Lexie..." he hissed at the camera in a hushed, terrified voice, "Please, I'm going to explode...Either let me stop or turn off the Control Ring email, PLEASE Lexie...I can't do this much longer..."

The next response almost made him faint. "Oh no no no, that's not how it works boytoy. You hold it back, or every single person in your office is going to get a highlight reel of all of our games together. That was the agreement remember? I might even include a link to the live feed if i'm feeling really naughty..."

As he stared at the camera, desperately mouthing the word "please" as he attempted to quiet his panting, another message came through. "They're all out there right now, don't forget. You're so close to being caught, just one locked door away... And the only thing protecting you is your willpower. So no cumming Daniel. Just keep stroking and stay calm while Krista makes me cum with her strap on again, it's SUCH a turn on watching you sweat and shake, darling..."

Dan whimpered and gasped as he struggled not to explode, and quickly learned several ridiculous looking but helpful ways to survive this onslaught he was being forced to put himself through. Spreading his legs as widely as possible while arching his spine seemed to lessen the pressure against his prostate, as did spreading his ass cheeks between the thumb and forefinger of his left hand. As long as he kept two fingers or more fingers moving slowly against the shaft of his cock, Lexie seemed satisfied, and so he spent the next 45 minutes drooling, bent face down over the desk his desk, as he lightly stroked the underside of his cock with the fingers of his right hand, and bend forward with splayed legs to spread his ass cheeks with his left.

His cock felt like it was electrified, like heat was actually emanating from it as he stroked and teased himself for Lexie's benefit, but all he could think about was how close he was to peers and colleagues that had NO IDEA what he was being put through. Everything about his agreement was becoming even more real now. He HAD to keep himself from cumming. There was no other choice. He clenched his muscles in an effort to keep his hips as still as possible. Every sexual instinct in his body was telling him to thrust forward, but any movement would only pull this rubber jackhammer deeper inside of him.

Every 5 minutes or so, Lexie would send him another update on what they were doing now, and Krista even messaged him herself once or twice. Every message was laden with just enough detail to send his mind racing, as he pictured Krista's luscious round ass and full thighs, and Lexie's gorgeous fiery red hair. He struggled to think about the History Channel, politics, anything other than sex, but it was like trying to hold back a flood with an umbrella: he was completely overwhelmed almost immediately, and sucked away into insane, dirty fantasies about what they were doing to each other. But somehow he made it through, shaking and sweating as Lexie, after almost an hour and a half of this, began to slowly lower the intensity buzzing against him.

When the vibrations finally turned completely off, Dan received one last message from Lexie, which read, "You may turn off the live stream and get dressed now Daniel. I look forward to seeing you for your shift tonight...don't forget, you have your next Monday Test tonight, so rest up. Ciao."

With that, Daniel was left to quietly gather up his clothing and get dressed, stopping only to mop up the leaking mess that was the tip of his cock. He didn't know how much longer he could survive like this. He had to work harder: to do better at their tests, to not make any mistakes. He cringed as he again thought about the slight twitch of his fingers that cost him his orgasm yesterday. Such a stupid, insignificant thing, and such incredible consequences. "No more", he thought to himself grimly. "I need to be careful now."

"No more mistakes."

Chapter 7: Dan's Second Mistake

The rest of Dan's work day was uneventful, but almost the instant he got on the road, driving towards the club, the plug began vibrating again. It was only slightly, just enough of a tickle to remind him that it was there, but that was plenty to keep his mind focused on the evening ahead of him. He never knew exactly what he was walking into, but the girls LOVED to keep him apprised of who was working what shift, and that was usually enough to keep his imagination swirling.

Sarah and Lexie were in charge of him today, which was as terrifying a combination as any other. Lexie's lethal, casual cruelty was enough on its own, but with Sarah you always had to watch five steps ahead. She seemed to love using Dan's words against him, and whenever she was in the room with him she was always almost on top of him. He could barely handle her gorgeous blue eyes, her beautiful smile, or her drop dead gorgeous curves on a normal day, and now steam was pouring out of his ears before he even walked in the door. He had no idea what to expect from the two of them working together.

As he had done ever week night for weeks now, Daniel parked downtown, nervously sneaked around to the back alley behind the club, and came in through the staff entrance. Then, as he had also done every night for weeks, he quickly undressed, folded his clothes in a neat pile by the door, and hurried down the hallway towards the break room. No matter how many times he did this, he never stopped feeling exposed during the terrifying seconds of nudity before he reached the break room. But of course, things never got any easier once he entered.

When he walked in today, Dan saw Lexie sitting on the couch looking bored, wearing a long sheer robe lined in a fluffy black fringe. The fabric of the robe was so sheer it was like she was wearing slightly tinted gossamer, and underneath she wore a skimpy, very expensive looking black lace lingerie set, complete with stockings and a garter belt. The moment she saw him, her demeanor changed, and she smiled, uncrossing her legs daintily and adjusting the soft, billowy fabric of the robe as she stood.

"Welcome Daniel." she said, her eyes moving cooly up and down his naked body, and she sauntered deliberately over to him, her shiny black heels clicking loudly, "Sarah's running a little behind, but I don't mind spending a little time alone with you. We do have business to take care of, after all...don't we Daniel?" She reached out and took his arm in the crook of hers, forcefully leading him over to Trixie's "Chair" in the back of the break room. Then she turned to him, and crooked one copper eyebrow expectantly.

Immediately, and without another word, Dan began climbing into the custom made bondage rack, settling into the contoured plastic and letting his wrists and ankles fall between the thick buckles that decorated the edges of the contraption. He knew exactly what was happening: after all, he had already done it twice. It was Monday, Lexie was here, and that meant it was time for the Monday test. The test to determine whether the girls kept him chaste for another week with the threat of exposure...or whether they had to resort to...harsher means.

"Another hour of endless edging," he thought with a whimper, as he settled the weight of his torso down and watched Lexie begin to buckle his wrists and ankles securely in place. This time, however, the seat of "The Chair", which was molded perfectly to the shape of his buttocks, pressed pleasantly up against the plug still inside of him, causing him to gasp. "Lexie..." he stammered in a panic as he watched her strut slowly around him, that billowy, see through robe flowing behind her like a perfumed cloud, and her fiery hair flouncing around her shoulders. "Can we take the plug out first? Please? I wore it all day for you all, and it's been driving me crazy..."

Lexie smiled almost sweetly at that, and reaching up to pat his cheek condescendingly as she secured the final straps in place. "Oh...No no no, Daniel. Not until your shift is done. Now..." She reached behind her, grabbing a stool, and sat down, crossing her knees primly. Then, she hit a button on her phone, lowering the Chair so that his body was horizontal, and just above her knee level. She looked at him with those cool, emerald eyes, and the briefest of smiles flashed across her full, soft lips before she said, "I trust you remember how this all works?"

Dan nodded up at her, a bit more eagerly than he had intended, and Lexie snorted. He flushed with embarrassment...he knew how pathetic it must seem to be so eager for torture if it meant torture at her hands. But...he couldn't deny how he felt. His cock was already rock hard and standing to attention, before she had even touched more than his arm. He knew that in 15 minutes he would be wishing more than anything for the edging to end. And he knew that there would be no way out, no way to make it stop. But right now, all he wanted, more than anything in the world, was for her to start touching his cock.

Instead, she turned around to look at the clock on the wall, and watch as the second hand ticked slowly back around to the top. His gaze followed hers, and he watched, taking note of the time himself. He hadn't decided whether he thought paying attention to the time during these shifts made him feel better or worse, but he couldn't seem to stop doing it. "It's just for an hour," he told himself shakily as he prepared for the constant edging of the Monday Test to begin, "After that, they'll probably make you eat them out for a while or something, just make it through the hour...Remember: No more mistakes. You can do this."

Lexie slowly slid her fingertips along Dan's thigh and up towards his throbbing cock, smiling calmly as she did so. He moaned and strained against his bonds the instant he felt her soft, delicate finger pads stroking against the base of him, and he let out a wavering moan as she slid a finger slowly up the underside of his cock. He suddenly realized that the last time he had done this with her, he had just cum the night before. This time, not only had he not orgasmed in over a week, but he had spent the last 24 hours in exquisite sexual torture. He had no idea how he was going to make it through this.

Lexie barely said a word as she rested her head lightly on his thigh, and stared up at him. Her gorgeous green eyes were wide with false, liquid innocence, but he could see the predatory, laughing glint hiding behind that look. He watched the white shimmer of her curved fingernails slowly encircling his cock, and began to immediately gasp as she placed the pad of her thumb against his frenulum, and began to slowly...SLOWLY...trace light circles against it.

She slowly batted her eyes at him as he watched her, silent and trembling. She was always so clearly in love with this part: starting SO slowly that he was practically struggling not to beg before she was even really touching him. Normally, while watching her like this was torture, this didn't feel like the hard part yet. But now that he was in this extreme sexual overdrive, he actually had to bite the corner of his mouth to keep himself from breaking out into sobbing pleas. There was nothing else he could do: he knew that his only hope was making it through the rest of the week, trying to be as "good" for them as he could, and somehow convincing them to grant him mercy next Sunday.

But the idea of waiting another week brought tears to his eyes as Lexie began to gently part her lips, and slide her face farther forward against his thigh, so that he could feel her hot, moist breath panting against his scrotum. He strained his hips as far as he could, moving himself perhaps half an inch closer towards her, as she laughed merrily at his useless writhing and straining. The only time Dan ever saw Lexie's genuine smile was when she was amused by his squirming body, and despite the humiliating reason for its appearance, he couldn't help but marvel at how beautiful that smile made her. Her perfect, dazzling, straight white teeth framed by those soft, juicy lips...he stifled another moan as he struggled to keep his mouth shut.

Just as had happened the week before, Lexie sped up slowly, always gently increasing her speed and pressure, so that Dan knew: no matter what she was doing to him currently, this would only keep getting worse. After breathing softly on his dripping cock for almost five minutes, Lexie began to gently lick at him, almost playfully, like she was licking a lollypop. The wet dragging movements of her tongue each sent a moan through him, but they were so brief that he was constantly desperate for more. After almost five minutes of this, Lexie began softly cupping and massaging his balls as well, while she continued her soft, playful tongue bath.

For the first 15 minutes, she toyed with him like this, all while slowly rubbing her thumb against the underside of his cockhead in tiny circles while she stared at him, never breaking eye contact, and the act of teasing was so powerful that she managed to edge him twice with that stimulation alone. She giggled as he gasped and strained against the thick buckles holding him in place each time. Soon however, she grew tired of doing this as she watched his struggling, bug eyed expression, and she leaned forward, opening her mouth wide, and letting it hover over his cock as she stared up at him.

He was so constantly focused on making sure that he did nothing that could be interpreted as breaking the rules, that he even tried to stifle his whimpers and moans. During the Monday Test, the only thing he REALLY wasn't allowed to do was to beg. But at this point, he didn't know if he trusted Lexie not to try to say that some warbling moan that came out of him was actually a "please." He wasn't going to do ANYTHING that she could use against him. "No more mistakes," he thought to himself on repeat, like a mantra, as he watched her wet mouth slowly descend over his throbbing erection, "No more mistakes..."

As Lexie's soft tongue began to swirl and curl around his cockhead, he writhed and humped. Then she slid her hands slowly up his chest, beginning to tickle playfully at his nipples while she slurped at him, and he began to wriggle and squirm. Every time he moved, the contoured ass of the chair drove against the rubber toy inside of him, reminding him of it's presence. He repressed a moan as Lexie's lips squeezed hungrily against the base of him before slowly sliding back to the tip, only a squeaky wheezing coming out of him.

She licked, and slurped at him slowly for one agonizing minute after another. And every time he reached the electrifying, flooding sensation of orgasms edge, she let his cock slide wetly out of his mouth, before she began whispering sweet temptations to him as she let him fall back away from the edge. "Oh Daniel...Krista's cock filled me up so nicely on Sunday, but I must confess I had hoped it would be you...I was going to be your prize if you had passed, you see my darling..."

He grunted and shook, trying and failing to look away from her as she continued, lightly stroking his cock as it dripped with saliva. "I'm so wet for you right now Daniel...do you want to fuck my tight pussy?" Her voice was throaty, almost as if she was as turned on as he was, "If you say yes, maybe I'll let you...Do you want to feel me wrapped around your throbbing cock Daniel? Do you want to feel me sneezing against you, and my ass bouncing against your thighs as I move up and down and up and down?"

He bit down hard on his tongue again, trying to ignore what she was saying. He knew by now that she would say anything during the Monday Test to try to break him. He couldn't believe any of it. But he thought back to his first evening with Lexie, as she had slowly ridden his cock while he sat frozen in place, and remembered how tight she was, and how deliciously she rolled her hips against him. And in spite of himself, he began to drool.

Every time Lexie released him, giving him a precious few seconds to recover before attacking his cock once more, she would purr and promise, tease and cajole, in an attempt to get him to say anything to her. "Oh Daniel...maybe if you beg me, I'll let you shoot all that hot, roiling cum down the back of my wet throat...Or maybe you want to feel your cock between my toes as you spurt your naughty boy juices? Just tell me Daniel, all I want is to give you want you missed out on yesterday. Don't you want me? Don't you want more?"

Dan quickly found that the presence of the plug rubbing deliciously against his rectum caused him to reach the edge of climax much more quickly than normal, and soon she was bringing him to the edge ever 5 minutes or so. Every time Dan felt his balls pull tightly against his body, and that coppery, warm sense of pleasure flooding throughout his body from his groin, Lexie pulled away at the last instant. Leaving his cock bobbing and twitching desperately, covered in crimson lipstick kisses and dripping with saliva. And each time her sweet, tempting promises filled his ears again.

He kept a close eye on the clock on the wall, counting down the minutes in what felt like slow motion. By the 45 minute mark, Lexie had brought Daniel to the edge over eight times, and he was mewling like an injured kitten as he contorted his body at bizarre and sudden angles in one unsuccessful attempt after another to escape his bondage. "No more mistakes. No more mistakes. No more mistakes..." he thought sternly to himself, repeating his mantra to himself over and over as he bit his lip again, desperately trying to make it to the end.

Dan struggled and gasped, humped and panted, sobbed and shook. But he didn't say a word. As the clock passed the 50 minute mark in his hour long journey, he began feeling confident that he could actually do this, and celebrated the relief he felt that it was almost over. It was around the 55 minute mark, however, when the evening got much much harder for poor Daniel, and he realized just how much more he would have to endure for the evening.

Almost at the exact instant the second hand reached the top of its arc of travel, the door to the break room swung open, and Sarah sauntered in, wearing a tight, tiny electric blue string bikini and a pair of clear, stiletto heels. His head swiveled the instant he heard the door, turning to see her bounce and jiggle towards him with a very happy smile on her face. "Hi Danny!" she squealed with excitement, as she saw him shaking and trying not to drool. Her short, rocker girl hair was styled in a spiky, jagged bob that bounced around her soft, round freckled face, still in her signature two tone blonde and electric blue.