Poker Loser Ch. 09

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I’m glad you seemed to enjoy yourself so much on our last date, you’re awfully hot when you’re being fucked every which way and enjoying it so much. This Friday you’re going to be all mine though. We’re going out again, I’ll mail you a package of what I want you to wear, along with a few items. 5pm on Friday Princess. Last date.

Your King of Hearts


The package came on Wednesday, opening it, Allison pulled out a gorgeous silk dark red dress. It was fantastically low cut in the front, a string across her cleavage would be all that would keep it from gaping wide over her breasts. The back was scandalously low, and a long slit up the back only left about 8″ of material between the bottom of the back and the top of the slit; in the slit was chiffon which would sweep out behind her like a train when she walked. She was going to look like sex in heels. Underneath the dress were a few Ziploc bags holding a butt plug that looked like it would be much more comfortable than the one she’d previously worn, some kind of smooth metal bullet object, and a chain that had two little rope loops on the ends. Looking over the instructions in the bag, she found that the bullet object was for her pussy, and the little loops were meant to tighten around her nipples. At the very bottom of the box was, shockingly, a pair of panties. Maybe he just didn’t want to bullet to fall out of her; but when she picked the panties up, she could feel something smooth and hard in the crotch of them. Confused, she found there were no instructions with it… well, only two days till she found out. She found herself unreasonable excited – and a little sad that this was going to be the last date. Ridiculous, she was probably just not used to having her Friday’s open, she’d just have to find something else to fill them with. Maybe dates with other guys, sweet romantic guys who wanted her for more than a fucktoy. Sweet, romantic, wonderful guys who wouldn’t call her “Princess” and turn her into some kind of slut.

Allison wanted to kick herself when the pictures of these guys she was conjuring up did nothing to excite her. Putting the silky dress in the back of her closet, she shoved the package under the bed and went to meet a friend for shopping. Maybe she’d look for a new guy to take her out on Friday nights.


Friday evening found Allison feeling unaccountably nervous as she looked at herself in the mirror. She didn’t know why she would be getting an attack of nerves, it wasn’t as if she liked Todd after all, she just had to deal with him for one more date. Still, she definitely looked better than she had for any other date barring her high school senior prom. The dress fit her perfectly, clinging seductively to her curves. Her cleavage was daringly bared by the V-neck that went almost to her belly button, and the back of her dress hugged her ass and gave a great view of her legs through the chiffon in the slit. The dark red color brought a natural flush to her cheeks, and made her skin look golden tan; red highlights stood out in her hair – which she’d deliberately put up in a French knot, knowing that Todd liked it down. With the high heels and her make-up, she looked like the highest priced hooker one could buy. Smoothing her hands over the silky dress, she got a certain amount of pleasure as the smooth material caressed her skin.

The little gold chain connecting the two hoops around her breast was clearly visible in the V-neck of the dress, and it was pretty obvious where the ends of it went as her nipples were held at attention by the little nooses. It didn’t hurt at all, it was more like something firmly gripping her nipples teasingly. When she walked the hardened nubs rubbed against the silky material covering them, which just teased her even more. The bullet was firmly in her pussy, it was cool when it first smoothly slipped in but was now warm as it was engulfed by her body. As she had thought, the plug had barely hurt at all when she’d pushed it in; barely half as wide as Todd it had only been a little bit of stretching pain as her ass opened around the widest part of the plug. Really not uncomfortable at all.

The doorbell rang, and she rushed from her room, butterflies filling her stomach. Scolding herself, she told herself to stop being so stupid; after all, this was a guy that had monopolized her body for his own depraved uses for the past 5 weeks. Maybe she was just happy that it was all finally going to be over. Opening the door, she found Todd standing there, looking incredible hot in an actual tux and holding one long stemmed red rose. She actually blushed as he looked her over with open admiration in his eyes.

“You look incredible,” he said, and stepped up to kiss her. For a moment, it was everything she’d always dreamed of in a date, until he slipped one hand down and caressed the silky material covering her ass. That brought her back to reality.

Still, he acted like a gentleman for the most eryaman arkadan veren escortlar part, graciously handing her the rose and escorting her to the car. He even opened the door for her to get in. The car ride was surprisingly pleasant as they talked and he made stupid jokes that made her giggle at his dorkiness. It was surprisingly normal.

They went back to the same restaurant as their first “date”, only this time Allison found she didn’t mind the stares that she got as she walked by the other tables to the same booth they’d sat in before. Then she jumped a little, as they were about halfway to her table… the little bullet in her pussy had started vibrating. Out of the corner of her eye, she could see Todd grinning slyly at her with one hand in his jacket pocket, and she realized that he must have some kind of remote that set it off. A few more steps and the smooth hard thing in her panties began to vibrate… right over her clit. It made it much harder for her to concentrate on walking, when they finally got to the table he turned both off.

It was funny how the gestures he was making were almost romantic (other than setting off remote vibrators); sending her a gorgeous dress to wear, the single rose, taking her back to their first restaurant and even getting sat in the original booth (although that might have been nothing more but wanting to keep her in the back where he could play with her more). Still, Allison was strangely touched by it all; he didn’t have rich parents the way she did, he must have used his own money to pay for it all. And even though he worked almost full time, he still had lots of other things to pay for. Not to mention that it wasn’t as if he had to do this, he could have just as easily just had her come over to his house naked under a coat again and had just as good a time for himself. Instead, he’d opted to make the last date… well, kinda special. She smiled at him as they settled into the booth.

Those feelings lasted about as long as it took for the waiter to get to their table, her to recognize him as being the same one as the last time, and for Todd to make the plug in her ass start to vibrate as the waiter took their drink orders. Back to business as usual.

But the date was pleasant for the most part, although he kept setting the vibrators off at odd times during the meal; sometimes just one, sometimes more than one and always at different speeds. A couple times he set off all three at once, at a very high speed and her eyes almost glazed over as she completely lost track of the conversation while incredible sensations spread through her lower region. She was completely hyped up, and actually rather eager to get back to his place by the time the waiter took his credit card for the check. After all, this was the last date, she’d get one last incredible fuck out of him and then she’d be on her way with life and she’d never have to do anything like this again. Lesson learned, it wasn’t going to be one that she repeated. Besides, she did feel some kind of closeness to him, he was the guy who’d taken her virginity after all, and last week she hadn’t really been able to pay much attention to him as everything was going on all at once. One last time could actually be… quite nice. And then she’d get closure too.

Allison realized that she was making up reasons for why she should cooperate and enjoy herself that night, but she didn’t really care. After all, she couldn’t think of any reason not to. There wasn’t one really.

When the waiter brought the credit card back to Todd, he again paused and looked at Allison, “Could I… again?”

Todd grinned at him and the three vibrators began to buzz away at a low vibration; he slipped the straps of Allison’s dress off so that her breasts were completely out in the open, nipples firmly gripped in the little loops. The waiter tugged at the chain connecting her nipples, apparently unsure as to how to get it off, and Allison gasped as the little nooses tightened on her nipples and Todd turned up the intensity of the vibrators. After a moment of squeezing her nipples tightly, the little loops popped off of her nipples, sending little jolts of pleasurable pain through her breasts. The waiter gripped her breast flesh firmly in both hands, squeezing as his mouth descended on her right nipple.

With the warm mouth suckling and nibbling on her tender bud, Allison moaned softly and Todd turned the vibrators up another notch. When the waiter moved his mouth to her other nipple, Todd turned up the vibrators all the way and leaned down towards her breast.

“Bite it,” he told the waiter, and taking her right nipple into his own mouth he followed suit.

Allison came as the two mouths bit her nipples, the vibrators going at high-speed in her ass and pussy and pressing into her clit. Trying to keep her moans down, she clenched her fists and arched her back as her orgasm flowed through her entire body. Finally, her heart stopped racing and her pulse slowed, her body relaxed back into the etimesgut escort bayan booth and the men lifted their heads from her swollen, wet nipples.

“Thanks,” the waiter looked at both of them appreciatively before walking off. Todd reattached the little nooses around her nipples, making her moan again slightly, and then she pulled the straps of her dress back up over her shoulders.

“Come on Princess,” he helped her out of the booth, and they walked out of the restaurant, his arm around her slender waist, fingers slowly stroking her silky hip.


Back in the apartment, Allison surprised Todd when he turned from closing his bedroom door. She stepped forward, and put her arms around his neck, lifting her face up for a kiss. Surprised and extremely pleased, he lowered his mouth onto her pert red lips and they kissed passionately as he ran his hands up and down the smooth material covering her body. Step by step they moved back towards the bed, her hands pushing the jacket off of his broad shoulders and nimbly unbuttoning his shift, without ever pulling her mouth from his. His job was much easier, the silky dress slid easily from her body as he rolled it over her hips, and she gasped into his mouth as he pulled the nipple loops from her body.

Finally he had to let her mouth go as he stepped out of his pants, and pulled her panties down her thighs. Admiring the smoothness of her legs, he also pulled the egg from her dripping pussy, and removed the plug from her ass. Then he pulled her back up into his arms and they began kissing again, her tongue moving as ardently in his mouth as his did in hers. She actually sucked on his tongue as he probed her mouth with it, and he groaned low in his throat.

Pulling away for air, he lowered his hungry mouth to her breasts, sucking hard on the unblemished flesh. Like the first time he’d had her in his bed, he wanted to leave his mark, this time because it was the last of their “dates”. He left mark after mark on her boobs, kneading the heavy flesh with his fingers and his mouth, pinching her nipples and stretching them away from her body before releasing them to bounce back. Sucking the nipple into his mouth, he bit down as she moaned his name. Damn that was hot. He liked the way his name sounded in her mouth, especially when she said it like that. Rolling the nipple with his tongue, he let his fingers slide into her pussy, they were immediately drenched in wetness. Pushing two fingers up her slick hole, he pumped them in and out of her, coating them with her juices before bringing them up to her mouth.

Allison willingly licked her juices off of his fingers, sucking and nibbling on the tips as she cleaned them. It was like she was an entirely different person. Todd couldn’t take it anymore and he spread her thighs wide and pushed his needy cock into her waiting pussy.

When he slid home, Allison looked up at him, “Did you know that I was a virgin the first time?” she giggled as he looked completely dumbfounded for the first time of their entire acquaintance.

After a moment’s pause he answered her, “No… but that definitely explains why you were so tight.”

“Would it have made a difference?” she asked

“Well,” he smiled down at her, “I might’ve gone for your pussy first and kept your ass for later.” He began sliding his dick back out for the first thurst, “Does it bother you that I was your first?”

Allison couldn’t even begin to put her feelings into words, so she just shook her head.

Todd leaned forward and kissed her mouth, pushing his tongue between her lips as his dick thrust deep into her pussy again. As her pussy stretched around the thick meat, she arched her back and moaned again, trying to push more of it into her.

They fucked decadently, hands running up and down each other’s bodies, and moving together in rhythm. Allison was passionate in her responses to him, always molding her body to get the best possible impact out of his thrusts. Her slender body writhed and heaved beneath his, her pussy convulsed around his penis, tightening and loosening as their pleasure mounted. Todd was ecstatic at her involvement, although he knew that she’d respond once she’d worked her body, he hadn’t been expecting her to be so involved and definitely not from the beginning! He knew that with this unexpected situation, he wasn’t going to last long, at least not for the first round.

Wrapping his arms tightly around her body, he held her close, pressing her breasts flat against his chest. Biting the skin between her shoulder and her neck, he began thrusting in and out of her powerfully. Allison wrapped her legs around his body as he pummeled her pussy, pulling him in closer as her arms did the same. Todd lost it and slammed her body hard, jets of his cum shooting out of his cock into her wetness. The last thrust and his dick’s increased hardness and the pulsing of his cum flowing through it was enough to set Allison off. Crying out his name, sincan escort bayan her legs tightened around him as her pussy convulsed around his dick, her nails digging hard into his back; they passed the finish line together.

After a few moments of laying there panting, Allison wriggled a little beneath him and he rolled off of her.

“I hope you don’t think tonight’s over,” he smiled hazily at her.

“No,” surprisingly she giggled a little, and then pushed him so that he was laying on his back. Looking him over, she inspected his entire naked body. It was strong and lean, with toned muscles; a small patch of hair on his chest and then a happy trail leading down to the shaved area of his groin. Which right now was covered in their cum. Getting onto all fours, Allison leaned over his crotch and began licking the juices off of him, cleaning him with her mouth. It was sex on her tongue as she made sure to include his balls, licking juices out of every wrinkle in it. By the time she was done, his dick was a little bit firmer, but not nearly hard.

Allison began to explore the rest of his body, with fingers and tongue, finding what places made him tick. Trailing her fingers along his sides and the insides of his thighs made him shiver, touching and massaging a spot just behind his balls made him moan and his dick jump a little. Remembering the sensitivity of her own nipples, she abandoned his lower body and teased his much smaller nipples with her fingers. They hardened and he shivered a little, so she lowered her mouth to them, testing. She was rewarded with a moan and his back arched slightly as it sent exquisite sensations straight to his balls. Giggling a little, she moved her mouth to the other nipple, giving it similar attentions. Returning her caresses, Todd reached one hand over and pinched one of her own hanging nipples, after all they looked so tempting, like hanging fruit. He cupped the breast in his hand, feeling the weight of it in his palm. Abandoning his nipples, Allison moved her lips higher, kissing up his shoulder blades and neck; when she got to his ear she licked it and he tensed and tightened his hand on her breast. Sucking it into her mouth, she bit down gently and he groaned as the gentle nibbles sent a message straight to his reviving dick. She sucked and nibbled some more, and then moved her mouth to the other earlobe, repeating the attentions. By now Todd’s hands were filled with both of her breasts, stroking gently and tugging on the nipples like he was milking a cow.

Sighing happily, she glanced down and saw that he was completely hard again. Repositioning herself, she straddled his hips, surprising him again. Using her hands to position the thick meat, she slowly lowered her body down onto it. It took a little longer to work his dick all the way than when he was on top, in this position she had to hold herself up and that made her inadvertently tighten her pussy muscles. With a thick shaft like Todd’s that meant that it felt like she was stretching more than usual as his dick penetrated her wet hole. Finally she was completely impaled on his dick, it felt like it was filling her even more than usual and she moaned as she began to lift herself off it before sliding down again. For his part, Todd was delighted at her initiative, and even more delighted with the change of position. For the first time he was getting to watch Allison’s body bounce on top of his, her breasts jiggling sexily as she rode him. Watching for a moment, he realized what was missing and used her hips to pull himself up.

Allison stopped her movements, slightly startled, and then understanding as Todd’s hands released her hair from it’s confinements. Then, as he lay back to watch her again, putting his hands on her hips as she moved on top of him, her hair swayed about her shoulders and head as she rode him. Grinding her body on top of his, Allison enjoyed the sensation of being in control of the action for the first time with Todd. She plunged his dick in and out of her tight pussy, hands in front of her on his stomach for balance, she rubbed her clit against his groin every time she hit home. Her breasts pushed prettily between her arms, she began grinding her clit more and more often as she fucked, using his dick like a sex toy of her own. Reaching up to pinch her nipples, Todd enjoyed the look on her face as she began creaming herself all over his dick. Since he’d cum so recently he wasn’t ready to again, and he got a real treat watching her moan and cry out while her body ground itself onto his. With her head back, panting his name, hair flowing like a waterfall down her back, breasts bouncing with nipples jutting forth proudly, she made an incredible sight.

As she continued to convulse around his hard cock, he couldn’t take the view anymore. Not without doing something about it. Using her hips to pull himself up again, he wrapped his arms around her waist and locked his mouth onto one jutting nipple, sucking and chewing on it, and he began moving his body beneath hers while she came. Allison was just starting to come down from her orgasm when Todd shifted positions beneath her. With him sucking on her nipple and the way his body now pressed firmly against her clit while his dick bounced off her g-spot with every thrust, her body immediately began climbing to a higher, much more intense orgasm.

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