Poer Loser

Hey Princess,

Our date is going to be Friday, I'll pick you up after I get off of work at 5pm. Wear your hair down, I like the curls, and wear a button up shirt and a skirt. The skirt shouldn't be a tight one, but it should be short. And heels, I want to see those legs. No underwear at all. Don't worry about anything else, I'll have it all arranged.

Your Prince Charming

P.S. Make sure you keep it clean and shaved down there, I was very disappointed in the library to find that you hadn't kept up with the grooming I gave you.

Allison snorted as she read the email. Prince Charming... that asshole. There was nothing to do about it though, just hope that Friday came really really slowly.

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When Todd arrived to pick Allison up on Friday she looked almost perfect. A loose, white button-up shirt (which was buttoned all the way to the top) with a grey, short, pleated skirt and black 2" heels. It was almost exactly as he had pictured it.

"Unbutton the top two buttons." Allison stared at him defiantly for a moment, and then shrugged and undid them, the shirt didn't open to expose more than above her chest. With a bra there might've been some cleavage showing, but without one no one's tits were that naturally perky. Insolently, Todd leaned forward and used a finger to pull her shirt away from her chest, making sure she had no bra (And, not so incidentally, enjoying the site of her bare breasts, just as he remembered them.). She gritted her teeth as he smiled and nodded his approval, "Now lift the skirt." Turning her head away, she lifted the hem of the skirt so that he could see her bare and shaved pussy. No underwear. With him demanding a skirt she'd had the feeling that she'd just have to take them off before they even left the house. It would've been a useless defiance.

Walking to his car, he chatted amiably at her, while she remained in stony silence. Deciding to get a reaction out of her, he slid one hand up her thigh and under her skirt, cupping her bare cheek, and almost exposing it to the neighborhood. Getting the hint, Allison began responding to his small talk. One of things he asked her was if she was on the pill, she almost hesitated - thinking that maybe she could avoid sex she said no (although she had been since she was 15 to regulate her period) - but he dissuaded that notion by mentioning that he had condoms, and that she'd better get on something soon. Six dates, she told herself, just six dates, just six times. Sure I won't have my virginity anymore, but no one else needs to know that... but I can't let anyone see that tape... I'll lose everything. Sighing, she admitted that she'd been on the pill for years.

The restaurant he took her to was 45 minutes away, across the state line, "Don't want anyone Daddy knows to see you with a low class guy like me," He'd said, winking at her in the car, "He might ask uncomfortable questions." She'd just blushed and turned away. A couple times on the car ride, he'd reached over into her shirt, toying with her breasts while they talked; it'd been an effort for her to keep up the conversation. Her breasts were almost abnormally sensitive, and it hadn't helped that several cars had passed by each time, it's occupants staring at the activities going on in theirs. Grimacing, she realized that she'd left a slight wet spot on the seat when she got out of the car, probably from the times he'd spent playing with her tits. It was humiliating to have her body responding to him in this way, but she didn't seem to be able to help it.

Todd obviously knew the people at the restaurant, including the owner, and quickly had secured them a table in the back corner of the restaurant, a half-circle booth where he pulled her in close next to him. The waiter was also obviously an old friend, and was just as obviously eyeing the gorgeous girl sitting next to Todd. Allison looked around the restaurant as Todd and the waiter chatted, noticing that their booth was practically invisible to the rest of the patrons, no one else was remotely near them. She winced internally as she realized that Todd had probably planned this too, and that she might not escape humiliation in public, as well as later in private.

Eventually the waiter left, Todd had ordered for both of them, and she was left alone and vulnerable again.

Trying to head off any possible public sex acts, she immediately began questioning him, on his life, his childhood, his interests. Anything and everything she could think of. To her surprise, it turned out to be more interesting than she'd thought, and she managed to keep him occupied until their food arrived, even telling him some things about herself. The realization that they could almost be out on a real date made her feel very strange, she wasn't exactly here by choice after all. Everything was pretty normal until they'd ordered dessert, and were sitting without food to occupy them again. Todd observed her with one of those burning looks that told her when a guy wanted her body, she'd used to like seeing that look in a guy's eyes, seeing it and flaunting herself to taunt him with what he couldn't have. Seeing it in Todd's eyes made her want to shrink into herself. There wasn't really anything he couldn't have at this point. The deal she'd made with him had really sunk into her over the past week, she hadn't really established any limits before making it, other than denying him overnights. It had been a stupid thing to do, and now there wasn't really any going back on it. There was no way he'd be willing to re-negotiate now. All she could do was deal with whatever came.

He let his arm casually drop around her, pulling her in for a kiss. Sickened at the thought of having to passionately kiss this creep, she still let her mouth open under his lips, accepting the deepened kiss without really kissing back. It didn't seem to bother him. The kiss continued, his tongue probing her mouth aggressively, as she tried not to finch away from him, then his other hand unbuttoned the third and fourth button on her shirt, and slid in, cupping her breast and squeezing it. She struggled for a moment, against him, but his firm hold on her breast and mouth convinced her that he wasn't going to be denied this, at least he wasn't exposing her breast to the restaurant, so she stopped fighting him. After a few moments of him squeezing and kneading her flesh, he began using his thumb against her nipple, gently rotating the little nub and rubbing it enticingly, it sent little shudders of pleasure up and down her body. The hand on her breast became more forceful, and his tongue pushed deeper, as he moved his fingers over her nipple, pinching it firmly and twisting it back and forth. She moaned into his mouth, and as she did so she realized that not only was she half in his lap, but she was kissing him back just as passionately as he was kissing her!

Horrified, she pulled back, pulling her body out of his grasp - just as the waiter came to the table with their desserts. Shirt half open, her curves were clearly visible - although thank God she wasn't completely exposed - but before she could even move to recover herself, the voice of doom toned, "Leave it." Todd was looking at her firmly, and the waiter's eyebrows shot up as she slowly lowered her hands at his order. Both men's eyes roamed over the visible curves, and she was aware that her chest was heaving as she breathed deeply, trying to calm herself. Closing her eyes to the waiter's surprised and speculative look, she finally heard him walk away.

"Very good Princess."

She glared at Todd, "Stop calling me that."

"I'll call you whatever I want, Princess," His smile hadn't diminished in the slightest, "Now come here and enjoy dessert." It was a brownie fudge Sunday, but with a strawberry rather than a cherry on top. Todd removed the strawberry and held it while she got a couples mouthfuls of the admittedly very good dessert. Watching her expression, he smiled as she either forgot, or became used to the air flowing through her opened shirt. He sucked all the chocolate syrup and whipped cream off the strawberry.

"Spread your legs Princess." Caught with a mouth full of ice cream and brownie she stared at him as he grinned maliciously at her. Composing herself, she swallowed, held her chin high, and obediently spread her legs. Todd chuckled at her snobbish expression as he slid the strawberry under her skirt and along her slit, wetting the red fruit with the juices collected there. The cold fruit made Allison shiver as its rough edges pushed along her lips, and she prayed that he wouldn't actually push it into her. He didn't, he did much worse. Holding it to her lips, "Eat it Princess." Hazel eyes pleaded with him, but when he continued to hold the sopping fruit in front of her lips, she reluctantly opened her mouth and let him put the strawberry into it. Biting down she could taste the sweetness of her favorite fruit intermingling with the musky sweetness of her pussy juices. It really didn't taste bad, mixed with the strawberry, it just disgusted her to know that her own juices were in her mouth, she could even really say why except that there was something very wrong about it in her head. Todd seemed to get a lot of pleasure out of seeing her eat a strawberry covered in her pussy though, he watched avidly as she ate the entire thing, and then he had her clean his fingers of the wet residue.

After they finished their dessert the waiter came back with the check, Todd payed with a credit card, and when the waiter returned he hesitated for a moment before leaving their table completely.

"Would you mind..." his voice trailed off, but his eyes were riveted to the almost exposed curves of Allison's chest. She glared at him, wishing she could shoot daggers from her eyes at his temerity.

"Sure!" Todd's acceptance made her freeze. Before she could even begin to form a protest, Todd was pulling the sides of her shirt back, and as cool air brushed her nipples, teasing them to hardness, her face was slowly heating to fiery red. "Here, have a taste." The only thing that kept Allison from screaming was the knowledge that if everyone came back to see what was going on, she'd be totally exposed to all of them as well.

Instead she just closed her eyes as the waiter slid into the seat next to her and lowered his mouth to one of her nipples, squeezing and rolling the other breast in his hand. Closing her eyes was a mistake, it allowed her to concentrate only on the warm soft mouth that was sucking oh so gently on her nipple; she clenched her teeth to keep herself from moaning as he rolled the nipple between his teeth and tongue. A moment and he transferred his mouth to the other nipple, pinching the wet one with his fingers as he gave its partner the same treatment he'd given the first.

The waiter straightened up and nodded to Todd, "Thanks man, you guys made my day. She's a hottie. Where'd you get a slut like this anyway?" Allison flinched, not only at their casual treatment of her, but at the waiter's assumption that she was there because she was a cock-hungry slut. Dammit, she was still a virgin, although not exactly innocent anymore, and even if she wouldn't be a virgin after tonight (which she highly doubted she'd get out of this situation with that intact) she still was at the moment!

"Oh, I have my ways." Todd winked at the waiter who nodded and left them. With slight tears in her eyes at her total embarrassment, Allison pulled her shirt back over her breasts, and started to button them, until Todd's hand over hers stopped her. "I think it looks good like that, leave it. And come on, time to go home." He grinned at her totally forlorn expression, as his inflection left no doubt that it was to his home they would be going, and that she would have to walk out of the restaurant with her shirt half open. If anyone in the restaurant didn't already suspect there was hanky-panky going on in the corner, after she walked out like that they'd all be sure of it.

Defiantly, she got to her feet and walked firmly but quickly, head held high, ignoring the shocked (and appreciative) stares and muttering of other guests. The owner of the restaurant looked her over insolently as she walked out, a few steps ahead of Todd, wishing them a "Nice night." in a rather suggestive voice. Her face burned, but she didn't stop walking until she'd reached his car.

Once inside he started it up and then turned to her, "I think you need to be a bit more sharing with that bod you've got Princess, let's just open it up a little bit right now." And the bastard reached over and pulled her shirt flaps apart, completely exposing her breasts again, before starting up the car and leaving the parking lot.

The ride home was hell, not everyone noticed that her large, round boobs were hanging out of the front of her shirt, but the ones that did notice made enough noise and catcalls to make up for the ones that were oblivious. It felt like her face was never going to stop burning with humiliation, by the time they pulled up to Todd's apartment complex it was a relief, especially since he allowed her to at least close her shirt (although still not button it) before leaving the car. To her utter disgust she realized that she was actually feeling grateful to the jerk for allowing her that small decency. She vowed to keep an eye out for more manipulations like that in the future, she'd be damned if she was caught falling for that one again! His amused gaze informed her that he knew exactly what was running through her mind, and that he didn't mind she'd figured out that particular ploy. Haughtily, she turned her nose up away from him until they got into his apartment.

Once there, he shocked her, immediately stepping forward and pulling her into his arms, kissing her harshly and deeply; instinctively she responded to his passionate kiss before her mind caught up with her body, reminding her not to react to him. Not that there was much room for her to react, he pushed her up against her wall, grinding his hips into hers; one hand reached into her shirt and latched onto her breast like a suction cup. His almost violent advance startled her, until she realized that he'd been toying with her all evening without much stimulation for himself. The obvious for her that he showed, and the skill and passion in his kisses, made it hard for her not to get swept away in the moment; it was a fight to keep herself from responding ardently to him, especially because she was aware of the juices wetting her inner thighs. She was aroused, there was no denying that, she could be anything but with the pressure of his dick on her groin, his hand kneading her boob, and his mouth possessing hers so completely. But that didn't mean that she had to give into that arousal.

From moment to moment she would respond to his kiss, push back his groin with her own, arch her back to press her breast even more firmly into his suction-like grip... and then she would recall herself and pull away, still the impulse, and desperately try to get back control of her body. When he finally released her mouth, her knees were weak and her lips felt swollen and bruised. He swept her up in his arms, walking quickly towards the bedroom, they were barely inside before he set her down again and his mouth found hers again. The occasional responses that he got from her were thrilling for him, knowing that she wanted him but was fighting those feelings just made him all the more determined to overwhelm her into giving in. His tongue practically raped her mouth, as he tore his clothes off with one hand, the other arm securely around her slender waist, holding her body pressed to his as much as possible. Once his clothes were scattered on the floor, and the thick cock that she was fast becoming familiar with was free of its confines, he practically ripped her shirt off and pushed her back onto the bed.

With one quick movement her skirt was on the floor, and he practically pounced on top of her; she raised her hands, trying to ward him off, to hold onto her virginity for another moment... but that wasn't his goal yet anyway. Mouth latching onto her nipple, he sucked at it ferociously, nibbling with his teeth. It had become pretty obvious just how sensitive her large breasts were, and he wanted her wet and wanting when he finally entered her. He began moving his mouth over the large globe, sucking to leave hickeys, lots of them, marking her as his own. There was no way she'd be going on a date with anyone else with his lovebites on her skin. Hickeys were left all over her breasts, her collarbone, and then he began moving onto her stomach, leaving his hands on her tits, rolling her nipples between his fingers. Allison was barely aware of the marks he was leaving, she was becoming caught up more and more in his animalistic passion, and the heavy attentions her boobs were receiving left her panting and whimpering, sending urgent and needy signals straight to her pussy and clit.

After leaving a trail of hickeys from the base of her neck, all over her breasts, and down her stomach, Todd began nibbling on her inner thighs... she spread her legs without even realizing what she was doing. His mouth dove onto her pussy, devouring her juices, and one of her hands clutched his wavy hair, pulling him closer into her. Licking, nibbling and sucking, he attacked her pussy with the same focus that he had her chest, all the while continuing to pinch and twist her nipples. Allison was completely out of control now, totally intent on reaching a much needed orgasm, so lost was she in her body's pleasures, that she didn't even notice when Todd's face left her pussy and was replaced with his dick. If he had been more slender, if his dick hadn't been so wide, she might not have noticed, she was so lost in the pleasure, but the thickness of his meat caused her pussy to stretch ridiculously wide, and it hurt as he slid home. Arching her hips up in pain, she actually helped his entry more than anything else. Tears sprang to her eyes, partially the sharp pain of being stretched so quickly and so wide, partially for the loss of her dreams of a romantic wedding night where she'd lose her virginity to a caring, gentle, loving man who worshiped her.

Todd didn't even notice the tears, he was totally lost in his own little haven of pleasure at the moment. Allison was tighter than any girl he'd ever been in... she'd lost her hymen at an early age, it hadn't been that thick, so he had no idea that she was still a virgin, just that she was the tightest fuck he'd ever had. Most girls were pretty tight on his cock anyway, just because it was so thick and most of them had never been stretched wide like that, but Allison beat them all. It felt like his cock was being crushed in the warmest, wettest, most wonderful place ever; the moments he took just holding his cock in that incredible tightness allowed Allison's body to adjust somewhat to its new proportions.

Then he began to move, slowly, sawing his cock in and out of her body. Her mouth opened in an O shape, although no sound emerged yet. It hurt in the most delightful way, her sopping pussy was still wet and needy, and the pain almost added to the pleasure; friction and heat built between her legs as he began moving faster and more roughly, she could hear him moaning in her ear about how tight and wet she was. The long teasing buildup of the evening had had it's effect on her, when he was eating her out he'd gotten her so close to orgasm that she realized it hadn't really gone away when he'd entered her... rather, she was very soon going to be cumming all over her first cock.

The thought should have disgusted her, it should have horrified and humiliated her, and logically she knew that, but right now her emotions and body were a lot more concerned with getting off.