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Destiny had been receiving the attentions of boys for as long as she could remember, but she had never felt comfortable with the way men seemed to want to treat her in the bedroom. She liked being in charge, she learned quickly, and the more she was able to talk boys into letting her tie them up, the more she learned how much she loved cock teasing, and the quivering, shuddering, squirming things she could make a trussed up boy do with even just the tip of her finger.
Unfortunately she had also realized quickly that most guys don't care for that sort of treatment, and despite her beauty, she had spent much of her young life scaring off the many men who came after her with her quickly escalating kinky female domination tease games. Most didn't last more than a week or two, and the ones who stuck around for a few months (one college boyfriend suffered through her torments for a whole year) always hurt a bit more when they left her. New boys were always waiting next in line, of course, but really, Destiny was a romantic at heart, and she often found herself longing for a boy who would not only stick around, but would love her MORE for being a cocktease. Someone who would really love her for her. A yummy little boyfriend that she could play with as much as she wanted.
She was starting more and more to think that Dan might be the guy that she had been looking for her whole life. The way his cock responded to his treatment of her was proof enough of how much he enjoyed what was happening to him, but after she had so bluntly laid everything out on the table for him during their date on Friday (making observations that anyone not already half insane with arousal probably would have realized in a second), she had seen the growing realization in his eyes that he was with them much more willingly than he wanted to admit.
Even though they didn't talk about it openly again after that night, Destiny had seen an immediate change in Dan's behavior after their dinner at La Bella. With his grueling morning workout, putting him through his paces with both breakfast and lunch, and three (god she was proud of herself, she giggled) different, hour long trips back to her wonderful shower together, she had really pushed his limits to see what he would accept this weekend. By 1:30pm, around the time they were finished with their post PB&J shower, Dan was an absolute wreck, but he didn't actually fight her (not really) ONCE the entire morning, and she was so impressed that she really did keep her word and let him take a nap.
He had slept on the couch, completely still for almost 4 hours, and he was so quiet and motionless that more than once she leaned in a bit to make sure he was still breathing. While he did that, Destiny finished up a few quick work emails, texted a few friends, checked her social media, and started getting dinner ready. She was a pretty decent chef herself, and she had thrown together some rosemary chicken and potatoes that ended up turning out pretty well. As dinner simmered, she puttered around a little, enjoying the quiet as Dan slept like the dead, finishing up and getting ready for the evening.
She started by pulling her hair back into the same large bouncing afro pigtails that she had been wearing when she first met him in the club. Then she had put on a pair of thigh high white socks, a pair of red booty shorts with white piping that disappeared up her incredible ass, and a thin white tank top that pulled so tightly against her massive tits that her dark areoles were almost fully visible for through the fabric. She had decided she wanted a quiet night in with Dan, and it felt like a good night for snuggling clothes.
Dan had woken up, looking like he wasn't sure where he was, just as she was plating up dinner and lighting the candles on her dinning room table. She giggled at his face when she told him to relax while she finished up. Destiny hadn't shied away from flirting with Dan and showing off for him physically as they ate dinner, but unlike the rest of the time they had spent together, she was no longer constantly verbally teasing him or stroking his cock.
For the first 20 minutes of dinner, while she asked him mundane questions about his life like they were in the middle of a normal Saturday evening, she could tell (with a little amusement) that he didn't want to let his guard down. Eventually, however, his nervousness started to fade, and they ended up having a wonderful evening.
They had similar senses of humor, and she had instantly been able to tell that he found her sweet, soft demeanor absolutely intoxicating. In fact, now that he was a little more used to the idea that he might actually be enjoying this time with her, she could tell that he was starting to develop a bit of a little crush on her. Which suited her just fine, of course. If things went the way she expected tonight, she would be taking advantage of it very pleasantly. After dinner, she snuggled up with him on the couch and they took turns picking old sitcoms to watch, arguing about which were better.
Eventually, Destiny had gotten up to make some popcorn, grabbed a blanket, and popped on a movie, cuddling up close to him. He had absolutely tensed up the second she had pressed against him, clearly ready again for some insane new torture to start, but instead she started When Harry Met Sally, and he soon realized with relief that he was still (for whatever reason) "safe". As they watched the movie, they talked about favorite bits and scenes ("As rom coms go" Dan had said sheepishly, "this one isn't bad") and the evening had turned into quite a relaxing and romantic intimate experience.
They made out a few times, but Destiny never tortured him the way she had that morning, and he slowly, slowly began to let his guard down more and more. While the sudden, unexplained change in behavior clearly made him quite nervous waiting for the other shoe to drop, she had been quite proud that she had turned her little "cool down" period into a quite romantic evening in. By the time the movie was finishing up, he was almost completely relaxed, laughing and cuddling with her, and already looking at her with something close to love in his eyes.
It was around 9pm by this point, and Destiny had suggested that they go to bed early, giggling that he needed to "rest up for tomorrow". But poor Dan had been about to learn that he wasn't going to be sleeping anytime soon. After making him follow her slowly up the stairs, taking performative, swaying steps that showed off her luscious ass inches from his face in those teeny weeny booty shorts, she had led him back to her bedroom, and immediately ordered him to get naked once more.
Then, just like the night before, she had laid him on the bed, and using a pair of pink fuzz lined leather cuffs, attached his wrists to her headboard. As she had explained to him after their date on Friday, this was her preferred means of sleeping with boys...it was very simple, but it made her feel so much more in control. As soon as she had clicked his cuffs into place, she had looked down at him and smiled.
"You did so so good today, Daniel." she had cooed at him, as she began to slide her fingers lightly against his chest, "I had so much fun with you tonight too...It felt so romantic, you know, like we were a real boyfriend and girlfriend, or something. I really liked feeling like I was your girlfriend Dan...In fact, I was thinking of giving you a treat. And this time I mean a REAL treat. The kind of treat a real boyfriend would get. Would you like that Daniel? Do you want to be my boyfriend tonight?"
Her voice had lilted into the slightly higher, more playful tone she always used as she had shifted back into cocktease mode, and as always, the effect on Dan was instantaneous: his relaxed face suddenly tightened, a wild hunger suddenly appeared in his eyes, and his cock immediately began to bounce fully back to life. He had nodded with nervous excitement, and Destiny remembered with pride the emotional look of puppy love that had returned to his face once more. She remembered being struck again by how fully trained he already was: he was saying yes so BLINDLY now, ready to do anything to make her happy.
"Good Daniel," she had begun to purr, as she slid her other arm forward against him, and began to lightly circle each of his rapidly hardening nipples, causing her gorgeous massive melons to be put even further on display for him. They were almost falling completely out of the sides and the front of her tight, white tank top, and he stared hungrily as she whispered and breathed her words, "Because I want to play a little game with you, and if you play it right, you'll get to cum for me at the end."
She had giggled at the way his eyes widened and his breath caught in his throat at that, and continued, "Oh would you like that Dan? You're paying so much attention all of a sudden. Do you want to spurt all of that icky sticky goo all over me? Is that what you want?" She bit her lip and made her eyes as wide and soulful as she could as she cooed at him, absolutely adoring his nodding, desperate affirmation, "You do? You want to cum for me? To explode all that roiling, churning cum trapped in your balls? So you'll play my game? Ya?"
She had stopped playing with his nipples then, and lay down on the bed herself, on her stomach, holding her gorgeous soft face in her fists, and holding her calves up at a ninety degree angle as she softly and slowly rubbed her feet against each other for his benefit. "Ok Dan," she had explained with a smile, "here are the rules. We're going to play a game called 'Rate my Outfits'. I'm going to try on a few different fun little outfits in my closet for you, and once we decide which one is your favorite, we'll end the game, and I'll dress in it when I make you spurt! Doesn't that sound fun?"
Dan again had nodded as if under hypnosis, but the smile on his face, one of genuine excitement had almost broken her heart a little bit. Poor little guy...although he should probably know better than to believe something like this the night before the Sunday Hearing, she had thought to herself with a giggle. That was when she explained the rest of the rules.
"For each outfit, you're going to give me a score of 1-10. I'll wear it for you for a little while, we'll talk about what we think, and then you'll give it a final score. Of course..." she giggled, "if I think the score is TOO low, I might try to convince you for a few minutes to bring it up a little. But that's basically it. And then the highest score wins."
"Oh!" She had added, as if suddenly remembering something, and had worked to suppress a smile, "There's one more rule: it's up to you to keep track of your score for each outfit while I show off for you. I don't want to have to keep track of all that. And I don't want any ties, okay? If we end with any ties, I'll edge you with my mouth for 10 minutes to punish you and remind you of the rules, and then we'll start over with a tiebreaker round, until we have a definitive winner. So make sure you don't give two outfits the same score, Danny! Then, when we have a winner, you can spurt that big load all over me."
"Are you excited Dan? Ya?" she had asked with a sweet smile, as he continued to nod wildly in growing excitement that this was really happening, and she decided to push it one step further, making the trap as enticing as possible by adding, "I'm probably not going to let you cum inside my mouth or pussy tonight when you decide, since we have the Hearing tomorrow to look forward to, but I'll let you cum anywhere else you want: on my face, on my tits, on my ass, my thighs, my toes, even in my hands. So think about what you want while we play, and I'll let you pick when we have a winning outfit, okay?"
As he had nodded excitedly again ("God," she suddenly giggled to herself nowise she watched him sleep, "I bet he wakes up with a sore neck today from all that panicky nodding..."), she had rolled off the bed and strutted away, into her vast walk in closet and out of sight. She made Dan wait a few minutes longer than necessary as she readied herself for one of her all time favorite cock teasing games (she had come up with it with that year long college boyfriend, who had become so terrified of playing it with her that he had started sweating whenever they went clothes shopping together).
First she had come back in wearing the American flag bikini that Dan had first seen her in on Tuesday at the club. She loved this one: the white lining was surprisingly sturdy, and though the fabric barely covered more than her nipples, it never fell loose, even though it constantly looked like it was going to. As she crawled onto the bed, she purred, "Do you remember this, Danny? This is the first outfit you ever saw me in. If you want to be my boyfriend, you have to remember stuff like that. That sort of stuff's so romantic don't you think?"
Dan's eyes had immediately started crawling hungrily over every inch of her, and she could see in his eyes that he was already thinking about where he wanted to (as she had so enticingly put it) "spurt that big load". Poor guy. He watched her crawl around on the bed for a minute or so, a wild grin on his face. Now that he really thought he was going to cum, the kinkiness of all this was nothing but exciting to him. "So what do you think Dan? 1-10?"
Dan had started lightly grinding his hips against the air as he watched her pose and stretch (a habit that Lexie would probably say was bad slave behavior, but which Destiny found sort of cute: she loved how obviously out of control he was in her presence) and grunted, "A...Oh, god, I don't know...a Nine, Destiny." He was panting a little, and already had that wild look back in his eye, that look that she was growing so fond of, and found herself wanting to bring out in him more and more. It was obvious how much he loved this, and loved her for it.
While she was smiling internally at his adorable squirming, she put on a look of theatrical, shocked disappointment, and exclaimed an immature, hurt tone, "A nine! Dan this is the first thing you ever saw me in! And what do you mean 'I don't know', don't you think it's special?" As she said this, she dropped a hand between his legs, and began to lightly circle one finger against the underside of his cock head, and her other hand slid up her body, dragging her massive, barely contained breast up against her forearm as she bit sexily against her fingernail.
She threw the puppy dog eyes back in for good measure and whispered, "Don't you think it should be a ten Dan? I think so. I think it's really special, and nothing but a ten will do, what do you think?" She never stopped the slow circling motion of her finger pad against his cock, keeping her contact so slight that it must have felt like a feather, and after about 15 seconds of this, he had sputtered out, "Ten, you're right Destiny, it's a ten, that's the outfit I choose, ten is my answer."
Destiny had immediately hopped off of him, looking pleased, and walked back towards the closet. As she did, Dan called out in a cracked and desperate voice, "Destiny, please I...since I already gave this one a ten, can we just skip to the end? I'm so excited to.." he blushed furiously then, suddenly aware of how honest he was being, "to cum on y-you, like you said, and today was really, really frustrating..." She had looked back at him, putting on another expression of deep hurt and said, "You don't want to play with me anymore Dan? You don't want to be my boyfriend tonight? After what I just offered you?"
Dan immediately had backed off, and she could tell that despite his utter and total sexual frustration, he sincerely felt guilty for asking, for having possibly hurt her feelings, and he exclaimed, "O-oh god, no Destiny, that's not what I meant. You're right, I'm sorry I didn't mean to be impatient. Please, we can play for as long as you want." She smiled, pleased, and walked back into the closet, feeling very determined to make him regret those words.
The second outfit was a classic, sexy schoolgirl look, with thigh high white socks, a plaid skit (although it was more of a frill than a skirt, reaching only about half way down her ass, and leaving a pair of cotton white thong panties very visible against her dark skin), and a white collared dress shirt tied in a crop top around her massive tits. As she crawled on the bed, he saw that the only 3 buttons that were fastened strained violently against the weight of her chest as her tits swayed and jiggled gloriously.
"What about this one Dan?" She had asked coyly, as she began to lean forward and press her cleavage into his upturned, helpless face, "What score would you give this one?" She watched him navigate the rules in his head, and despite the obvious degree of excitement he was feeling, he sputtered out, "N-nine! I give it a nine! It's really wonderful and I would love to cum on you in it another day if you'd let me, but I still choose the other one."
She had pulled her tits away from him at this, looking frustrated, and had scolded him, "Daniel! I told you, I don't want to keep track of your scores, I don't care about what you gave the other one, we're talking about this outfit right now. You're only giving it a nine? You're telling me that this isn't the hottest thing you've ever seen? That you haven't had a schoolgirl fetish since you were a kid? C'mon, all boys love school girls Dan!"
Her face had brightened then, and she had looked at him with a theatrical gasp, squealing, "I know! I'll show you how good my ass looks in this skirt for a while, I bet that will change your opinion!" She spun around and straddled his chest with her soft, warm thighs, scooting her ass back against his face, and as she lightly bounced her luscious mocha cheeks against him, she leaned forward to lightly fondle his cock between her thumb and index finger, rolling it back and forth slightly.
"D-Destiny, can I ask a question?" Dan had asked in a voice hilariously muffled by her round bottom, and she smiled, responding, "Yes Dan, you may." His response was timid, terrified. "Can I change an earlier score now? So I can avoid a tie? I just really don't want to be punished..." Even muffled like this, she could already hear the crack of desperation in his voice, and she giggled at the question, "No Dan, you may not. Now be quiet and kiss my bottom for a while while I show you how great this outfit is, alright? I'll ask you if you've changed your opinion again in a few minutes."
He had done as instructed, and by the time she was finished, his cock was leaking profusely, and he was trying to wildly hump her fingers. Rather than admonish him for this, Destiny had allowed her fingers to expertly follow his thrusts, not giving him an iota more pleasure than she intended. By the time she asked him again what score he thought it should have, his cock had overtaken his mind as the primary decision making center in his body, and he immediately moaned out "Ten...ten, Destiny, please, ten...ten..." in a babbling voice.
Happy with her second conquest, she had climbed off of him, leaving him to lay there in agony, slowly realizing that he was in for a much longer night than he had initially thought, and the implications of her warnings about ties, edging punishments, and tiebreaker rounds finally starting to dawn on him. When she came out in the completely sheer red teddy that she had eventually ended the night in, he started to cry and shake against the bed, panting, "Oh Destiny, that's really wonderful, but I want that to be a nine, please, please don't try to convince me, I'm really sure I want that to be a nine...Destiny please I need to cum so badly..."
She had strutted towards him and slid back onto the bed, this time snuggling up against his side so that her tits pressed against his chest, sliding an arm around his back and pulling him close to press her mouth against his earlobe. "Oh, but Danny..." she had moaned wildly, directly into his ear canal, "this is my favorite one...Do you want to know why?" She had pressed further against him at this, wrapping her thighs around his hip, and he had suddenly realized that she wasn't wearing panties, that her bare warm slit was rubbing against his upper thing.
