Tease Toy Orientation 05: Saturday

She was staring down with a sly smile at Roger, who was attached to a bondage bench at her feet, and looking up at her on all fours. He didn't seem to have much choice in the position: his hands and forearms were completely encased in tight latex sleeves that held them flat against the front of the bench, and his calves and ankles were similarly encased in the back.

This made it so that all he could do by way of movement was sway about a foot forward, lifting his face up to see her as his cock pushed against the bench, or a foot backward so that his face fell against the bench and his ass stuck in the air. He was also wearing a very silly pair of headband cow ears, large and floppy with white and black spots, and a ball gag that was strapped securely to his mouth. He wore nothing else, and despite the fact that he was a slightly older man, his cock was already fully erect. None of her clients ever knew exactly what they were walking into for a session with her, so he still had no idea what was coming (or not, she chuckled to herself). All she had told him before getting him into bondage was that they were going to try a new role-play game she had come up with called "Green Acres".

"Are you comfortable, Roger?" she giggled, pleased at the look on his face, and suddenly very excited to tell him about today's games. "Do you want to know how today's session is going to work?" There was the slightest chance he would tap out immediately, she knew...but he also knew that if he did that (if he immediately safe worded his way out of his "punishment session"), as she had explained it in their opening interview, that she would remove him as a client immediately and cut off all contact. And poor Roger was SO PROUD that he had been accepted by the best, that she knew he would endure everything she had in store for him. She reached over to the small tray of tools she kept handy, and plucked a piece of paper from it. Then she cleared her throat theatrically before beginning to read out loud from it.

"My 'Punishment' Fantasy: by Roger," she began, smiling widely in amusement at the instant look of horror that came across his face, "If the requirement for my "Punishment Fantasy" is something I'll endure, but not enjoy, my answer, as much as I hate to admit it, would be extended tease and denial. I dated a very dominant woman in my younger years who enjoyed teasing and edging men in bondage quite a lot, but it always made me feel so crazy that I could barely handle it, and she got this look in her eye that really terrified me. After a while, I tried to find excuses to do it less and less but she was always so insistent."

"Eventually, I made her agree that she wouldn't ever do it for more than an hour. I always got sort of scared that she wouldn't untie me when it was over, that she'd just want to keep going, maybe NEVER freeing me. After a while I only let her do it on special occasions. One Friday night, we had had a smoked a little weed, which always made me feel very sexual, and she convinced me again to let her tie me to the bed, promising that she only wanted to tease me for a little while. It took a bit of convincing, but I finally let her tie me up and strap a ball gag in my mouth."

"The problem was, I was so buzzed that I had forgotten to discuss a safeword/gesture, and she was so high and enjoying herself so much that she forgot to keep track of the time. She kept me tied up for over four hours, licking and kissing, and rubbing, and bouncing on me, and I was screaming into my ball gag, but she just kept lighting up, toking, and continuing to torture me, like she couldn't hear me at all. I thought I was actually going to go insane after a while, and I still shudder when I think about it."

"I understand the appeal for some submissive men, but it always has absolutely made me want to crawl out of my skin. Wanting something, needing it that badly, and having it dangled just out of reach, over and over, it just made me feel insane, like my brain was short circuiting. While I would endure it for you (and even after that, I endured it for this woman I loved from time to time), but as your worksheet said, I really, REALLY don't want to..."

She stopped reading, and smiled down at him, as he began to desperately shake in fear. Then he started to grunt desperately, trying and obviously failing to say something through the ball gag, and he began to struggle slightly in his bonds, making the floppy cow ears on his hear bounce about ridiculously.

She stood up from her stool, and then walked around to the back of the bench, sitting comfortably between his latex encased calves, and she reached forward, beginning to slowly stroke at the underside of his erection with one finger, which in this position was hanging straight down between his legs, directly beneath his splayed and helpless anus. He moaned again into his ball gag in a sound of utter helplessness, and tried to press further back to increase her contact against him, and she pulled her finger away completely.

"You know Roger...I've been feeling for a little while like you've been taking me for granted. Like you forgot this little scenario was a real possibility if you pissed me off too much. And I thought it might be time for a reminder of exactly why you should be worshiping at my feet, if you would like the continued pleasure of my company. You know, at ALL times." She extended a fingertip and began to glide it lightly up and down the crack of his ass, her nail playfully tickle at his sphincter, making him jump and squeal, and she pressed the fingers of her other hand softly against his scrotum, where she stroked against him slowly.

She leaned forward as she played with him and whistled like one would at a dog, and he turned his head (resting awkwardly on the bench as he stuck his ass out desperately for her) back to make eye contact with her. "But, I thought since you've been such a loyal and well paying client all year, that maybe I should give you a chance to apologize for the way you've been treating me, and if you do a good enough job, maybe we could just skip this whole punishment thing."

She began to slide both of her hands away from his cock now, and instead began to drag her long, white manicured nails down the back of his thighs, causing him to giggle slightly into the ball gag as she asked, "What do you think? Is that a good idea Roger?" He nodded in desperately relief, but Lexie just sat there, acting like she was waiting for something. God she loved this part. "Well?" she said expectantly, "I'm waiting for you to start apologizing Roger. It better be good if you want to stop playing."

Roger stared at her, confused for a moment, and then horrified realization spread slowly across his face that she had no intention of removing his ball gag, and that there was no escape from this punishment. Lexie slid her probing fingertips back to his hanging, needy cock, and began lightly stroking again. "Well go ahead then Roger..." she cooed sweetly as she played with his vulnerable, helpless member, "Start apologizing to me. If I hear something I really like, maybe I'll show you mercy. You better be very eloquent and articulate though. You have a lot of specific things you need to say sorry for if you want the torture to end..."

Roger's eyes got even wider as he screamed muffled apologies and pleas for mercy into his ball gag, completely unintelligible with his tongue and lips stopped by the rubber sphere bulging out of him. Lexie sped up her fingers against his cock, milking her trapped, helpless little cow to the first of what would be many, many edges during his session, and as the sensation against his needy throbbing erection increased, his muffled apologies faded, and he started instead to moan wildly. Lexie let go of his cock with one hand and suddenly spanked him, hard across his bare ass.

"Hey!" she exclaimed in a stern voice, as she slid her fingertips down to his cock head and began to tickle playfully at it, making him drip with precum, "I didn't tell you to stop apologizing Roger. Just because I haven't heard anything to make me stop punishing you yet, doesn't mean you're allowed to stop saying sorry. Now keep going or I'll just have to punish you even more..."

As Roger began desperately trying to scream through his gag again, clearly begging wildly for mercy, Lexie smiled approvingly, and she returned her hands to his cock, coaxing him again to the maddening edge of climax before letting go of him once more. The session quickly fell into a pattern, and Lexie let her mind drift a little as she made him scream and squirm, thinking about what a wonderful weekend she had had with Krista, her one time nemesis, after Dan had so sweetly helped them bury the hatchet on Thursday.

"After almost three days straight of mind-blowing sex with Krista, I should probably find some way to thank Dan tonight", she thought as she began to lightly squeeze Roger's cock head between her thumb and forefinger, causing him to renew both his muffled begging and his useless physical struggles. She was starting to grow quite fond of their new full time Tease Toy. Being a professional dominatrix could be wonderful at times, but moments like this with clients like Roger were few and far between. With Dan she was going to be able to do whatever she wanted, whenever she wanted...

She could not believe some of the wonderful toys that Trixie had made for poor little Dan. God that girl was talented. And if that lunchtime lifestream had been any indication yesterday, Destiny was quite a force to be reckoned with as well. Lexie had always had the highest respect for Sarah's cock teasing abilities, and with these others on the crew, she was quickly starting to realize that she was no longer the only talented woman in the room. Which suited her quite fine, actually. Lexie did always enjoy being surrounded with the best.

She had always thought of Krista as a bit rough around the edges, and had mildly resented her inclusion in the group at first, but while she certainly WAS a bit rough around the edges, her appeal was also becoming more and more clear to Lexie. She had honestly been impressed with the variety of ways that she and Trixie had managed to dominant Dan's mind and cock from afar and up close on Wednesday, and even though Lexie had been steering the ship a bit on Thursday, the veteran dancer had held her own quite well there too. And of course there were the other benefits, the ones that they had been exploring all weekend...

As she lost herself in memories of lapping away at Krista's gorgeous clitoris, palming her hands deliciously around the gorgeous Puerto Rican beauty's impressive ass cheeks, she toyed and played with Roger for another 30 minutes, until he was literally screaming into his gag as loudly as he could. She smiled widely, feeling moisture begin to blossom between her thighs. She thought about removing Roger's ball gag for a while, and making him lick her to orgasm, but then she decided to save her own pleasure for later. "Besides..." she giggled to herself, " I want to keep up my strength for tonight..."

She stood up, and walked back around to the front of him, smiling down at him sweetly as he stared up at her with screaming, desperate eyes. There was a large puddle of precum lying against the surface of the bench where he was leaking non-stop. As he stared up at her, shaking with need, she slowly began to spin around for him, and simultaneously began to slide out of her slinky black evening gown, rolling it sensuously down her pale, freckled, hourglass figure, until she was standing before him wearing only her heels, her pearls, and her arm length white satin gloves.

As he stared at her, she began to pose and stretch in front of him, her hairdo, earrings, gloves, pearls and heels maintaining her "rich bitch" aesthetic completely despite her utter nakedness, and she purred, "I don't know if you remember this Roger, but when you first came to me, I asked if there was anyone in your life who you thought might be interested in helping with your kinky games. Do you remember that Roger?"

Roger nodded, suddenly very confused, "And do you remember that you gave me the names of, among others, your hot young secretary Tandy? I imagine because you were fucking her at the time, and saying that you were going to leave your wife for her, and probably thought she would be up for some sex games? Well ever since you STOPPED fucking her, and went back to your wife, she and I have been having a little email exchange, and we've been talking about you A LOT. See I was thinking, in your wonderful writing you said that the longest you'd spend in tease and denial was 4 hours, with that VERY interesting ex girlfriend of yours. And that naughty naughty jilted secretary of yours thought that that was a very interesting point to bring up."

She continued, relishing in the dawning horror on Roger's face, usually so entitled and smug, as he realized the magnitude of what he was actually in for, "Well Tandy and I decided that we should try to break that record today! I know you had a tee time over at the driving range after our hour long session that you just HAD to have right away, but Tandy wanted me to let you know that she went ahead and rescheduled that for you! Wasn't that sweet of her? She also wanted me to let you know that the reason you've had an erection since you left the office an hour ago, was that she put a viagra in your coffee to make sure you really enjoyed our session today. Man, you lucked out with her, didn't you Roger. Good help is so hard to find..."

She stepped closer and closer to him as she turned and spun, and stroked lightly at his upturned face as she continued, "And since I don't have anywhere to be until 6pm tonight, I was thinking we go for five hours today, Roger, what do you say?" He shook his head in terror and she suddenly stopped and looked at him sternly. "Oh? You're tapping out? You don't want to be my client anymore? Is that what you're saying? Do you want to stop?"

Panting, he thought for a moment, and then shook his head "no" in answer to her question. She smiled again, and let go of his face, "Well if you're not tapping out, you must think you've already apologized to me enough then. Is that it? Do you think you've apologized enough and earned my forgiveness?" He looked up at her hopefully for a moment, but that hope faded the instant he saw the cruel glint in her eye.

"Do you want to fuck me now? Now that you're hoping I've forgiven you? Maybe I have. Maybe you're forgiven now Roger. Do you think so? Is that what you want?" she cooed, leaning forward and pulling her gorgeous red hair around the back of her neck, and down across her freckled, swaying tits. He began to nod quickly, desperately, moaning with desire, and she giggled as she slid herself down onto the bench beneath him, wriggling down between his trapped forearms and calves with serpentine sensuality. She stopped when her tits were just about level with his face, and she moaned performatively as she spread her thighs, wrapping her heels and ankles firmly around his bare buttocks and pulling him down towards her.

"Go ahead then Roger. Go ahead, fuck me. Fuck my juicy pussy Roger, it's so wet for you..." she moaned in a cartoonish and performative gasp of lust, and she pulled his face forward into her tits, mashing them into him, as he began to desperately pump forward towards her waiting, moist slit. But he soon realized that this was not mercy either: Lexie had positioned himself so that, even at his deepest thrust, the tip of his desperate cock barely brushed against her wetness, and after five or six unsuccessful thrusts that succeeded only in teasing the tip of his cock further, he stopped in frustration.

Lexie took his face in her hands, pulling it way from her incredible, bouncing freckled tits, and smiled at him hungrily, her eyelids drooping in exaggerated arousal, and her mouth looking incredibly wet and inviting as she began to loudly and pornographically moan, in a needy, horny voice, "Why aren't you fucking me Roger? Please, oh god, please I need you...I need your hard, throbbing, massive cock in my warm tight pussy, Roger. Don't stop trying now. Please Roger...please I need you to fuck me. You can reach, I know you can...Please Roger I just want to feel you DEEP inside of me, please, I want to feel the HILT of you as you thrust and thrust into my wet, aching hole...Keep trying, okay? Don't stop Roger, please."

Knowing that it was a physical impossibility and still helpless to stop himself, Roger began humping wildly forward again, tears beginning to pour down his face as he felt the very tip of him brush lightly against her even as he strained every muscle in his body, and he started screaming his desperate muffled pleas and apologies into the ball gag again, wildly hoping for some end to this. Lexie tightened her ankles against his buttocks, holding him closer and making him take faster, smaller thrusts of his hips in his attempts to reach her. Then she slid one arm around his neck to hold him close and maintain her balance, and slid the other down between her thighs, brushing lightly against his bare chest as she wiggled her fingers down to her engorged mound.

"Mmmm I believe in you Roger," she whispered dreamily, as she began to finger herself while staring deeply into his desperate wide eyes with her shining emerald irises, "Keep trying ok? Don't stop. Don't stop. If you fuck me I'll let you go ok? I won't punish you for five hours like I promised I would. But only if you fuck me, okay? So don't stop trying. I'm just going to help myself out a little until you can reach. Keep going...Keep going...that's a goooooood boy."

She really did love her job and her life sometimes. Days like this made all of the headaches worth it. The desperation on Roger's face as he grazed maddeningly against her lips with his screaming cock...the smell and taste of Krista's hair and thighs still pleasantly fresh in her memory...and soon...Well, if things went as well as they were all hoping tonight, soon she would be able to take her work home with her any time she wanted. She had SO many fun ideas planned for Dan. She was already thinking of her favorite dungeon games to show him during their first weekend together. She couldn't wait.

She fingered herself and arched her back, pressing her breasts more deeply into Roger's gagged face, muffling his screams even further, and closed her eyes, feeling the pleasure and overwhelming power of dominating this entitled asshole so completely envelop her. It was almost time. Dan's final, total, and willing steps into absolute enslavement at their feet was almost here...

She couldn't wait...

Chapter 5: Destiny

It was Sunday morning...and that meant it was finally the day of Dan's first Hearing. It was already almost 11am, and Destiny was lying in bed, watching her helpless, trussed up tease toy sleep. She was wearing a red, incredibly sheer teddy that draped over her massive tits like gossamer, and she was smiling at the adorable, peaceful look on Dan's face. It made him look almost as cute as he did when he was bug eyed and screaming for mercy. She would be putting that look back on his face soon enough of course... but for now, she didn't want to wake him: the poor guy had had a long Saturday, and needed to rest up a little before they put him through this evening's festivities.

"Wow" she thought, smiling widely as she watched him snore, still completely naked and handcuffed by his wrists to the headboard, "he must be having a very happy dream!" His cock was rigid and twitching slightly, and Dan let out a slight moan in his sleep, twisting his hips slightly before settling back into a steady deep breathing. "Well, now I definitely don't want to wake him up yet," she thought, with a quiet giggle. She felt so happy watching him squirm and snore in the morning sun, lying trussed up in his bed like this.