Chapter 2

Shit!How could I have been so stupid? She was sitting in nothing but her g-string, across from Todd, and there was nothing in her poker hand—absolutely nothing. What made it worse was he was down to his boxers. Whoever lost this hand was the loser of the whole game. All she could do was hope he didn't have anything better than a Queen high.

After the bar, Todd had asked her if she'd ever played strip poker—of course, she hadn't—then he invited her over. The alcohol and the daring expression in his eyes after her confession had provoked her into saying yes. Talking with him, admitting there were experiences out there she craved and had never had, made her feel even more rebellious. His apparent approval of this side of her let her feel free to indulge a little. Plus, strip poker sounded like fun—especially with a smoking hot guy like Todd. It also sounded dangerous, and Allison wanted a little of both. She'd texted her mother and told her she was having a study session with a friend and would eat dinner out.

Now, she realized she'd gotten in way over her head.

The pretty brunette didn't even realize her face showed everything that was going on in her head, not that Todd was spending all that much time looking at her face. Her pert, 34C breasts with their puckered pink nipples were finally on display. He could see her face any time he wanted—this was something special. Todd subdued his impulse to grin at her discomfort, enjoying that she was exploring her wild side with him. A few of the guys from his frat had dated her, and he knew none of them had seen this much of her. True, she'd probably never date someone from his background, but he was thoroughly enjoying himself. Under her prissy and overly mannered exterior, there was a wild child just waiting to burst free, and he found himself fascinated by the small glimpse he was getting. Not to mention the spectacular glimpse of her body.

When Allison put down her Queen high, Todd almost groaned. The three Jacks in his hand seemed wasted when hers was so completely lousy. Still, it's not like he could truly be upset since he was finally going to see all of her gorgeous body.

Allison glared at him, hazel eyes sparking with anger and pride. The smug jackass was grinning, waiting for his victory. She couldn't take it. It wasn't a sore loser thing, but she was angry at the world right now. Something had to go her way in her life. Somehow, she felt sure humiliating Todd, making up for her embarrassment last semester when he'd turned her down, would do that. The plan to leave him at the bar wanting hadn't worked out. She'd wanted to see him naked and preferably hard, so she could set him down and withhold the view of her own body.

"One last hand, all or nothing," she demanded.

"We just had the last hand, and I already get to see all." Todd leaned back, raising his eyebrows, and waved his hand, telling her to get on with the show.

Allison felt reckless, and her nerves hummed with energy. For the first time in her life, she really felt fully alive.

"Really all or nothing. If you win, I'll be yours completely, to do whatever you want with for tonight. If I win, I get the same. And I mean anything."

Taken aback, Todd thought quickly, no emotion showing on his closed face. Who knew what embarrassing things she might have him do? Allison could have a mean streak, and he was sure if he lost, she'd be the only one getting satisfaction tonight. On the other hand, if she lost…

"Alright." He gave her a stern look. "But you need to take off your last item now. I have to lose twice in order for you to win the night." She looked at him aghast. "It makes sense. If you hadn't proposed this, then I'd be seeing what's under that delightful thong right now, and you'd have just lost the game."

Grimly Allison agreed. She wasn't sure what had spurred her to make the wager, a desperate need inside of her, perhaps. Her best-kept secret was she was still a virgin. Her mouth wasn't, but she'd been very good about not letting anyone into her pants. Todd was exactly the wrong kind of guy to lose her virginity to, yet right now, it seemed like it might not be that bad of an idea. He certainly gave off the impression that he knew what he was doing, but only if she lost.

If she won… She wondered what the wavy black hair on his head would look like between her legs.

Fate must be against her, she thought glumly. It was her worst hand of the night. Discarding three cards, she perked up a bit when she ended up with a pair of Jacks. Maybe it wasn't the best hand in the world, but it might not be the worst either. She could still pull this off.

No such luck.

Todd had managed another trio, three tens this time. As she looked up at him, she realized his eyes had changed from vaguely interested to something much more intense.

Her earlier conviction that losing her virginity tonight was swept away in sudden fear. Quickly standing, she tried to babble out some reason why she had to leave. As she turned to make a run for it, reaching down to scoop up her clothes, Todd jumped up from behind the table. Her nerveless fingers dropped the clothing, and she found herself pressed up against the wall, her cry of protest cut off as he covered her mouth with one broad hand. Heart pounding, she froze, like a deer in the headlights, unsure of what to do or where to run.

Hard hips trapped her from behind, pressing his erection into the softness of her ass cheeks. Allison's breasts were flattened against the wall, her nipples hard against the cool, smooth surface. Oh God, why was this so hot? She realized being trapped was turning her on. She had to get out of here before she listened to her body and did something she'd regret later.

SMACK!

She jumped and screamed as his hand came down on her ass. It didn't really hurt, but it frightened her, yet the stinging pain it left behind in its wake felt kind of good. Oh, what was wrong with her?

"You weren't thinking about going anywhere, were you?" Hot breath wafted across the back of her neck, and the low, growling whisper in her ear made her shiver. "Not after we made a deal. You lost the bet, princess. Time to pay up." He turned her to face him, dark eyes burning into hers as he pressed his hips forward, and his erection dug into her stomach.

Trapped in his gaze, she stared up at him, licking her suddenly dry lips. "I wasn't… I didn't…" She was stammering again. Confusion reigned, fear and arousal fighting a heavy battle for dominance within her body.

Lips came down on hers, not hard as she'd expected, but passionately and almost sweetly. It had been a long time since someone had kissed her like that… if anyone ever had. Her body began to relax into the kiss, and her mouth opened to his probing tongue. When his hand began to run down her naked body, she recalled herself and tried to pull away, banging into the wall behind her. As she tried to turn her head away, the kiss became rougher, deeper, commanding her submission. The worst part was she wanted to melt and give it to him.

Grasping her wrists, Todd pushed them above her head, folding them into one of his hands, so his other was free to being roaming her body. Lips left hers and began moving against her neck and upper arms, leaving her panting and gasping for breath.

"Oh, Todd… what are you doing to me?" She didn't mean what his hands were doing.

Allison had no idea what to do with the rising tide of lust in her body. She'd never felt anything like this before as if she was losing her grip on reality. Having her hands high above her head, body open to him, was nothing like any of the men she'd ever dated with their respectful close-mouthed kisses and their immediate capitulation when she removed their hands to a less sexual part of her body. This was raw carnality, taking control of her senses and burying her well-bred sense of decorum, making her quiver with need, and sweeping away the urge to protest.

Todd gripped her heavy breast in his palm, kneading it firmly with his fingers. Pleasure at his rough touch made her feel so weak in the knees, it felt like she was falling into a well of formerly hidden desires. His hard dick was pressing against her groin and upper thighs as he began to move against her, a parody of sex as he pressed her hips against the wall. Heat suffused her body, tingling between her legs and making her wriggle against him.

"Is this what you really want, sweetheart?"

Allison moaned as his teeth nipped at her collarbone.

"Yes… I mean no… I don't know!" Her last words were a cry for guidance. She was on the edge of tears, torn between what her body and rebellious side wanted versus the strictures of her upbringing and her parents' rules.

He tweaked her nipple as his tongue pushed deep into her mouth. She'd never been in such a conflicted sexual state. She'd always been the one in control, but now it seemed like she had no control, and he wasn't taking "no" for an answer. At least not the confused "no," which was all she had to give him. It was exactly what she'd said she wanted, exactly what she'd craved.

Finally, he pulled away, leaving her gasping for air, lips swollen from his kisses. Tossing her over his shoulder as if she weighed nothing, he carried her into his bedroom, ignoring her pleas to slow down and talk about things. He tossed her onto the bed, then grabbed a couple of scarves from his nightstand. Her eyes rounded as he tied her wrists together, put them over her head, and tied them to the bed.

"Please," she whispered. "Todd, please… not like this…"

"Not like what, Princess?" He raised an eyebrow, his hands hovering in front of her face with another scarf, obviously meant to be a gag. "Not like you said you wanted? Not the way I want since you promised to give yourself to me, however I wanted? Don't worry. I captured you." He grinned wickedly. "There's no reason for Daddy to be disappointed. We're going to go wild, and it's not going to be your fault at all. Now, open your mouth."

For one long moment, Allison stared at him, knowing this was her last chance to turn back and end the night. Todd waited patiently. She opened her mouth, and he pushed the scarf between her lips, securing it around her head. Being gagged made her want to resist again, so she kicked as he ran his hand up her inner thigh. With a laugh, he grabbed her ankles and soon had them spread apart and tied to each side of the bed.

Getting up, he stood at the foot of the bed and took stock of this new arrangement. Her pouty lips were spread around the scarf in her mouth, her perfect breasts heaving on top of her chest, nipples at attention, and the newest sight of the night—her pretty pink pussy with its neatly trimmed bush, slightly spread and glistening with her juices.

"You really do like it wild, don't you?" he asked as he moved around to the side of the bed, so he could reach her body. Running one finger between her pussy lips, he coated it in her wetness, making her convulse with a spasm of pleasure. Allison moaned, not sure if she was protesting or asking him to touch her more.

"Wait right here," he whispered, his mouth giving an amused little quirk before he turned and left the room.

Allison struggled against the scarves instinctually, the ones on her ankles especially uncomfortable. She was pissed as all hell he'd left her here! This wasn't how things were supposed to go. Somehow, she'd lost all control of her body and the situation, and without him standing there staring at her, she wanted the control back. Captured and tied up was not how she'd ever imagined losing her virginity. Well, at least not in her realistic fantasies. Granted, there had been a few, but Todd was not a pirate—even if he looked like one—and she wasn't a captured princess.

These thoughts stopped cold when he re-entered with a video camera and tripod and started setting it up. "NO!" she screamed behind her gag. Sound emitted from her, and it was obvious she was protesting, but Todd just smiled as if she'd said yes and finished setting it up. Pressing record, he turned and left the room again.

Tears sparked in her eyes as pulling against the scarves only made them tighten further around her wrists and ankles. What kind of knots had he tied, anyway? She stared at the lens of the video camera and the little blinking red light underneath. What was he doing? It occurred to her that her breasts were heaving and bouncing on her chest as she struggled, and she was probably making the video more enjoyable for him to watch later. Clenching her teeth around her gag, she resolved not to make a great scene for him to watch.

Todd came back into the room, his arms filled with items. He set down two bowls on the table next to her—one with water and one with ice, some kind of massage oil, a razor, shaving cream, a small washcloth, and a large purple vibrator, long and at least seven inches thick with small bumps covering its length. Where the hell had he gotten it?

Seeing her looking at the vibrator, he grinned.

"That was my ex-girlfriend's. Her favorite. She left it behind when we broke up. I figured I might as well keep it for future company."

Allison was disgusted. Another girl's vibrator in her pussy? The thought made her want to gag. He laughed at her expression.

"Don't worry, it's been cleaned."

Like that mattered. Guys just didn't get it. It's not like she'd never had a vibrator inside of her—that's how she'd broken her hymen—but that didn't mean she wanted some random stranger's toy inside her. The flash of jealousy, thinking about Todd with another woman, was something else to add to the ridiculousness of her emotions. Obviously, she wasn't thinking clearly anymore.

Todd knelt between her legs with the bowl of warm water, shaving cream, and the razor. Allison started to struggle. She kept herself nicely trimmed down there—a shaved bush was for perverts who wanted little girls, not women. Todd ignored her mewls of protest and lathered her hair—not hard considering her bound position, even with her wriggling and struggling. Picking up the razor, he smiled at her, a wicked glint in his eye. He was thoroughly enjoying this.

"Better be careful, you definitely wouldn't want me to accidentally cut anything down here."

Eyes big, indignation written across her features, all she could do was watch as he shaved her pussy clean. When all the hair was gone, he wiped her down with the washcloth and sat back to admire her newly bald pussy. Perfectly pink, her clit was poking out from between her little pussy lips.

"Even more beautiful than before."

He smiled at the furious expression on her face. Half of her anger was at herself for feeling happy he'd called her beautiful.

Putting aside the instruments of her humiliation, he opened the massage oil and squirted some into his palms. Deftly, he massaged her breasts, kneading them between his fingers, enjoying having the heavy globes in his hands and making them gleam slickly in the lamplight. Allison arched her back. Todd's hands felt incredible on her body—she liked this part. He was plucking her nipples, making her gasp and grind her hips into the bed. Her nipples had always been one of the most sensitive parts of her body. The massage oil was starting to heat up with the friction and giving off the distinct smell of strawberries. Her suspicion it was flavored was confirmed when he lowered his head to her nipple, licking and sucking it.

Oooh, that felt even better. His tongue flicked the tip of her nipple as he sucked it into his mouth, his free hand still playing with her other breast, pinching the tender nubbin. Her chest was starting to feel hot and even more sensitive as the massage oil really began to work its magic. When he lowered his hand to her pussy, she realized she was dripping, wetter than she'd ever been before in her life.

His fingers rubbed massage oil around her pussy lips, making them tingle warmly. She groaned and pushed against his finger as it slowly began to move into her. It felt slick and thick, and he added another finger, stretching her out. Then he lifted his head from her nipple, and she moaned and wriggled, wanting his mouth back on her.

Smiling smugly, he slipped off the bed and disrobed. Allison couldn't do anything but stare. He was huge, about seven inches long, which wasn't the longest she'd ever seen, but he was definitely the thickest. The massively wide dick bobbed its pinkish head at her, a fat stick hanging off his body, pulled down by its own weight. This was going to hurt. Allison found herself struggling uselessly again.

Laughing at her reaction, Todd fisted his cock and got onto the bed, straddling her stomach. She let out a huge breath of air in relief, he wasn't going to stick it inside of her yet. Maybe he would take the gag out and be content with a blow job.

He pushed her breasts together, creating a deep cleavage with the large globes and began pushing his dick back and forth between her breasts, aided by the massage oil. Allison had heard of "titty-fucking," but she'd never thought anyone would actually do it or enjoy it as much as Todd seemed to be.

Todd was enjoying his power over her more than anything else, along with the slick glide of his cock against her skin, the softness of her breasts in his hands, and the quickly changing expressions on her face. Looking down at her face, he could see the conflicted desire there. Allison was just as wild as she'd said, she just needed someone to help release that side of herself.

Releasing her breasts, he enjoyed watching them bounce back into place as he grabbed the vibrator. It was pretty obvious she was completely disgusted by the idea that it had been another girl's, and her humiliated disgust was a turn on in some way. Knowing she was his to do with as he pleased, knowing he was going to ensure she enjoyed this and broaden her horizons was incredibly arousing. Turning the toy on low, he began running it up and down her pussy lips, pressing it firmly against her clit, then pulling it away.

He had an idea. Turning the vibrator off, he put it aside for the moment. Untying both of her feet—tucking one under each arm so she couldn't kick—he tied each leg to opposite bedposts on the headboard, so they were higher than her arms, and she was bent nearly double. Now, there was complete access to her pussy and ass, and the camera would get a much better view.

Allison's new position wasn't the most comfortable, but she couldn't deny being restrained was just flat out doing it for her. She was incredibly horny and almost didn't care anymore that the vibrator had been someone else's first. This had to be the kinkiest way to lose her virginity. Now that she'd really accepted it, she found freedom in her bondage and lack of choices. Todd's tongue came down to lick around her pussy lips, sucking on her clit and teasing, kissing her inner thighs. She tried to push back, wanting more of the lovely sensation of his mouth on her most sensitive areas, but the new position he'd put her in made it almost impossible for her to move.

The heat between her legs was getting too heavy for her to ignore. She was panting and trying to move with the vibrator now, enjoying the moments when he licked and sucked her clit. There was nothing going on in her head except the thought of her own orgasm.

There was pressure on a place she had never been touched before, and she immediately tried to scream through her gag.

Noooo!

That was dirty! Dirty and wrong and gross… but the finger pushed relentlessly forward. Squeezing her muscles together did nothing except make him chuckle as the invading digit burrowed deeper. She winced as he wiggled his finger around in her asshole, causing her to clench spasmodically at the sensations. Thoughts of orgasm were dismissed—she wanted out now! Her ass was not part of a deal with ANY man! She'd been excited about losing her virginity to Todd, but this was too much!

She relaxed as he seemed to get her drift and pulled the finger from her ass. The bastard grinned at her as he began to push two fingers into her tight hole, causing her to wave her hips frantically—as much as she could, anyway. Straining, breath heaving in her chest, she screamed her frustration into the gag. It hurt, although not as much as she'd expected. His fingers spread her open in a way she'd never experienced, her tight hole aching with discomfort. Bearing down on them only made it hurt more as her sphincter muscles stretched and clenched.

Finally, his fingers were all the way inside. She mewled as her body slowly adjusted to its new dimensions. Todd watched her face as he began moving his fingers back and forth, mimicking sex in her asshole and causing her to wriggle at the strange new sensations. Slowly, it began to stop hurting, stop feeling quite so uncomfortable—at least physically. Mentally she was going crazy. Anal sex had never been on her menu. Good girls didn't do that. It was perverted, wrong—forbidden.

So, why was it starting to feel so good?

Fear returned when Todd pulled his fingers out and positioned himself between her legs. The buzzing pleasure of the vibrator did nothing to lessen her anxiety, although it seemed to heighten her anticipation. The wide head of his cock pressed against her crinkled hole, spreading open her virgin anus much wider than his fingers had. The discomfort was just shy of painful, and the actual spreading sensation was intense. She could feel herself stretching around the tip of the head, stretching and stretching and stretching… There was no way he was going to get that monster in her ass. He was going to tear her apart. As she began to panic and scream behind the gag in fear and pain, she inadvertently relaxed her ass muscles, and the head of his dick finally managed to pop past the tight ring of muscle that had been fighting it. Allison's eyes bulged.

Todd stopped for a moment, running his hands up and down her smooth legs as he let her adjust to the proportions of his cock, to savor the expression on her face. Thoughtfully, he also turned up the vibrator another notch, which would give her more pleasure to help with this discomfort. She was so wonderfully, exquisitely tight. Her body wriggled, trying to adjust rather than protest, now that he was inside, which was incredibly hot.

Leaning forward a bit, he slid himself a little deeper into her ass, causing her to grimace. Reaching forward, he began to play with her nipples. As the vibrator in her pussy and his nimble fingers on her nipples and breasts began to have their effect, she began moving her hips again. He pulled his dick back a bit before pushing more in. With her grimacing and groaning, he slowly worked his dick in and out of her ass, pushing a little more with every stroke. The vibrator moved inside of her, bumped by his body with every thrust.

Allison was beginning to work her way back to an orgasm. The sensations in her ass hurt, but the pain was lessening, and even seemed to be adding to the experience. She'd never felt so full in her life as if every crevice was stretched and overflowing with cock, both real and plastic. With the buzzing vibration in her pussy and the erotic stretch of her ass, the slick glide of Todd's cock moving back and forth over newly awakened nerves, her body was taking over again and pushing her mental and emotional objections aside.

As Todd hit bottom, he turned up the vibrator another notch and moved in and out of her stretched, deflowered, perfect ass. He could feel the vibrations through the thin membrane between her pussy and anal tract. Her ass was so incredibly tight, he was having a hard time not cumming, but he wanted to draw this out, but most of all, he wanted her cumming on camera while he plundered her virgin ass. As he moved in and out of her tight grip, he made sure his groin hit the bottom of the vibrator every time he filled her, causing it to move within her as well. Noticing the effect playing with her breasts had, he began pulling on her nipples, twisting them slightly with every stroke.

The combination of pain and pleasure was new to Allison, but her body reveled in it. She felt full, completed as if everything was finally right where it should be with her body. The biggest orgasm of her life was building up inside of her. Eyes half-closed, she was moaning and rocking her body, completely oblivious when Todd unwound the scarf from around her head, removing the gag. All of her focus was on the incredible sensations sweeping through her. He was moving harder and faster in her ass, giving her a ride, pulling harshly on her nipples. She could feel herself climbing higher and higher, getting ready for the great fall.

When Todd felt like he couldn't hold off his own orgasm any longer, he turned the vibrator up to full blast, grabbed her nipples and pinched down hard, pulling them away from her body and using the leverage to slam his dick into her ass.

Allison arched her back and let out a wildly sensual scream, not even realizing she could be heard.

"Oh, Todd!"

Her ass clenched hard around him, spasming as her body began to shake.

"Oh, Todd! Oh, God, I'm CUMMING! You're in my ass, and I'm cumming… oh, FUCK TODD! Fuck me, FUCK ME, FUCK MY ASS!"

Having those words come out of the spoiled, pampered mouth did it for Todd. He slammed his dick one last time into her convulsing ass and groaned her name as he spewed his load into her dark hole, completing the defloration of her most intimate crevice.

The pulsing rod in her ass caused Allison's orgasm to soar even higher, and she thrashed, crying out his name over and over again as her body rippled and pulsed. By the time Todd had finished spilling his load into her ass, Allison's nerves had reached overkill. She was sobbing and begging Todd to take the vibrator out of her pussy. Everything was so oversensitive, when he finally pulled it from her, her muscles went limp, and she fainted. The sensations had been too much.

When she came to, Todd had untied the ropes and was rubbing her wrists and ankles, putting soothing lotion on them. The red marks were already fading. Allison couldn't help blushing. In fact, now that she was no longer tied up, an unaccustomed shyness seemed to have overtaken her. Mumbling something incomprehensible, she fled to the bathroom and wedged toilet paper into her crack to catch the cum slowly seeping from her anus. The girl in the mirror was flushed, satisfied—terrified at what she'd allowed herself to do, to enjoy.

"I have to go," she muttered when she finally came out of the bathroom, fully clothed. Allison couldn't even look him in the eye.

"All right," he said, his voice surprisingly gentle. He walked her to the door and gave her a kiss on the top of her head since she wouldn't raise her eyes to look at him. "Take care, Princess."

She mumbled something and retreated to the safety of her car. Concentrating was difficult, but she managed. Fortunately, it was only about a twenty-five-minute drive without traffic from his apartment near campus to the gated neighborhood she lived in with her parents. Numbly, she walked inside, avoiding her family by heading straight for her bedroom.

The tissue in her backside was soaked with his cum, and her anus felt sore and used, which it had been. Allison got into bed naked.

She was still a virgin—sort of.

Fingers crept down to her pussy, stroking the soft folds as she thought about Todd's dark eyes, his commanding presence, the feeling of being completely under his control, the way his cock had felt gliding in and out of her protesting anus. It didn't take long for another small orgasm to rock her body.

Thoughts swirled around her head, but exhaustion overtook her, and she fell asleep, still wondering.