Anonymity

He obliged. Samantha felt Rory's strong hands go around her body, shifting the straps of her top down from her shoulders before bringing the entirety of it smoothly down around her waist. This time, she did kiss him. Their mouths met, tongues tangling together as she lifted one leg and then the other to allow him to take off her carefully-chosen lingerie. It had served its purpose, she decided.

Now naked except for the mask, she kissed the man slightly more forcefully for a moment. She felt his hands grip her in response; fingers and palms closing around the cheeks of her bum. The touch was almost enough to make her weak in the legs--so close, yet so far from what she needed. The throbbing in her body had reached a fever pitch.

"I want you to do to me exactly what the man in the video did to her," Samantha whispered against his lips, "Will you do that for me, daddy?"

"Of course, baby." He hesitated a moment, "But I might have to actually see this video, first."

"I'll show you." She leaned forward and kiss him once more, briefly but fiercely.

Breaking the kiss, Samantha turned in the man's lap. Straddling him backward, she raised herself slightly and bent forward so that her head and arms were supported by the table. It brought her ass almost perfectly level with the man's face, giving him a close view of both the tight ring of her asshole and the glistening folds of her labia beneath it. She felt his hands trail down the sides of her thighs before coming back up, taking hold of her cheeks and pulling them gently wider. A moment later, he leaned forward slightly and brought his tongue against the opening of her pussy.

The touch was enough to make Samantha gasp; a slightly shuddering, sustained inhale of air. He licked deeper, parting her folds around the sides of his tongue as he searched for the position that he knew--from experience--drove her wild. The pressure of it, Samantha thought, was perfect. Normally, it would have been exactly what she wanted, in this moment. It was only today that the position was wrong.

"Higher," she breathed, watching as her breath fogged the glass of the table beneath in front of her mouth and cheek. His tongue shifted positions slightly, now closer to the opening of her pussy. She could feel it gathering the wetness from inside of her. "Higher," she breathed again.

His tongue strayed a bit closer to the edge of her pussy, where it met the perinium. He sucked gently at her labia as his tongue moved inside of her. Samantha took a final breath to steel her nerves. When she spoke, her voice came surprisingly easily. It was slightly breathless, but clear and obvious.

"Higher."

She felt a bit of surprise; in his hands, in the movements of his mouth. But he didn't argue. Instead, he drew his tongue away from her pussy and over the smooth skin between her legs. Samantha shuddered, arms stretching out over her head and the flats of her fingers pressing against the glass.

"Fuck! Oh, fuck!--Higher!"

Finally, he seemed to understand. This time, there was no hesitation. She knew that she loved Rory, for that lack of hesitation. He didn't just preach sexual openness; he believed it, truly believed in it, and lived it. Without a word, he touched the wet circle of his mouth against the cheeks of her bum and prodded the hole with the tip of his tongue.

That touch, the smooth wetness of his tongue against the tense, slightly puckered dryness of her asshole, was enough to make Samantha wriggle. She knew they wouldn't, couldn't, but she thought that her fingers should shatter the glass of the table with how hard she pressed them against it.

"Oh--" a breath of air left her lungs explosively, "Yes! Yes--right there. Thank you, daddy!"

He replied with his tongue. Instead of words, he pushed it inside of her. Samantha gasped, as the tip of his tongue pushed through the tight ring of her asshole and into the space beyond. Again, without a second of hesitation. Closing her eyes, she let the first seconds of the sensation wash over her.

It was everything that she imagined it would be. The wrongness of it was enough to make her want to writhe; to twist against the glass of the table, to pull herself away from the man's searching, grasping mouth and slowly probing tongue. To pull herself away--and at the same time, to push herself back against him and grind against the man's face. Shame burned inside of her, but beside her arousal it was a candle beside a bonfire.

Instead of remaining as he was, she felt Rory lift himself slightly in the seat behind her. With his tongue still buried inside her asshole, rolling slightly, he reached a hand between her legs. Samantha's hips lifted instinctively as two of his fingers began to rub between her legs, brushing her clit with each pass. For a full minute he did this. And then, as his fingers came back, she felt them tense slightly and push inside of her. His fingers worked in her pussy, his tongue played inside her ass.

For Samantha, it was a breaking point. She felt a deeper warmth rush through her body, arms reaching out and fingers curling around either side of the desk; and then she came. She felt the passage of her pussy flood around the man's fingers. She didn't make a noise--she never did, when she came. It was a silent breaking, but a break nonetheless. As the final shudders wracked her body, Samantha loosened her fingers around the metal studs on the side of the desk and gasped for air against the glass.

"Fuck me, daddy." She breathed.

Reaching out, Rory grabbed her by the hips. Samantha felt herself pushed fully onto the table, turning over to face Rory as she was. Her legs rose as he stood. Without thinking, she brought them up around his neck--the same position that the man and woman had taken in the video, earlier.

He looked down at her, his brown eyes burning. Samantha brought her arms over her head, twisting her hands together as she heard the zipper of Rory's pants pull down.

"Should I ask about the condoms, baby?" He asked, stroking the head of his cock through her labia. She couldn't see it, but she could picture his hand wrapped around the base of it, helping its movement. "Something I should know?"

"Definitely," she breathed, blinking at him through the black leather of the mask straps, and from between the length of her legs, "Put one on."

"Is there something..."

"Put one on," she repeated, "Please, daddy. I want you so fucking badly. I need you inside of me."

She understood his confusion. She and Rory had been talking about having children for the last year; and if truth be told, they'd been mostly 'forgetful' about using condoms long before that. For somebody who didn't know where this evening was headed, or perhaps had only the slightest inkling, the change was confusing. He wouldn't believe they were necessary, unless she told him so.

"Okay, baby." Bless him. Without asking for an explanation, Rory reached out and grabbed a condom from the face of the desk. Tearing the gold wrapping open with his teeth, he took out the condom and reached down. She still couldn't see it, but she could feel it as the condom-covered length of his penis touched her once more. It rested against her pussy, pushing down slightly against her sensitive folds.

"You're close," she breathed.

He looked at her for a long moment. Their eyes met, over her body. Very slowly, Rory pulled his bottom lip backward and ran his tongue over it in a way that revealed his top teeth for a brief moment. He stared at her, obviously thinking fast and hard, considering and reconsidering.

"Baby, what was the name of that video?"

"What video?" She asked, coyly. Her voice mustered as much innocence as it could manage.

"The one you were watching earlier. Sam--what was the video called?"

She tilted her head, feeling the hair at the back of her head pull slightly against the glass. Pressing her lips together, she mimicked his motion from a moment ago; pretending to think before she replied. When she did, her voice was almost off-hand.

"Rough anal in detention for naughty student."

The sound that left Rory's body sounded almost like a sigh--if a sigh were magnified through a speaker. She watched the dim light from the partially-covered windows play through the brown circles of his eyes as he studied her carefully. Reading her expression, the discrete shifting of her body in barely-restrained excitement, the begging assurance in the lighter brown eyes that stared back at him.

"No." Rory's voice, the flat tone of it, made a knot catch in Samantha's throat. "Breakdown. Scenario over."

Breakdown-- it was their safe word. The knot tightened as she heard it. A bit of disbelief clouded her thoughts, and she fought to keep the desperate confusion from her face. Tried to smooth its features, controlling her breathing as she brought her legs down from his shoulders.

"You don't..." she began, but stopped when she heard the dismay in her voice. Her arousal, now with nowhere to go, writhed in confusion inside of her. She swallowed slowly before trying again. "This isn't something you want... to try?"

"No," Rory shook his head. As Samantha went to push herself up from the table, he raised a hand. He didn't touch her, only holding it flat over her body, thumb pointed toward the window, fingers reaching toward the ceiling, "No--wait. Let me explain. Sam, I love every part of you. I'll do anything you want, any time you want. If you want me to fuck your ass, I'll fuck your ass. No question, if anal's what you want then I'm perfectly happy to add that to our sex life--"

Samantha stared at Rory. Her body felt weak; but whether it was at the powerful rush of love she felt for him, or at the complete obscenity of the words that he spoke so easily--words she'd been desperate to hear for nearly a year--she didn't know. Before she had a chance to decide, he continued.

"But it's not going to be like this. If we're going to do anal for the first time, it's going to be our way. The way we've always done things. By asking, discussing, and agreeing. If you want this--" he leaned forward and let the head of his penis brush against the opening of her asshole, "Take off that mask and ask me for it."

This time, it was her turn to act without hesitating. Reaching up, Samantha lifted her head from the table. Her fingers found the small buckle at the back of the mask easily enough, and the button clicked as she opened it. Pulling the leather straps out of her hair, she dropped them over the side of the table. As she did, she looked up to meet Rory's grinning face. Her own smile came almost shyly.

"Hi."

"Hey baby," he echoed his words from earlier. His lips tilted, pressing the curve of a dimple into the skin of his left cheek. "Something you wanted to ask me?"

"Would you please..." She froze, the words unwilling to leave her throat. Her mouth remained open, and then closed slowly. For a moment, she only looked into Rory's eyes. In the brown circles of them, she found nothing but confidence--confidence in her, a patient kind of confidence that radiated from the man like heat from sunlight. He didn't say a word. He only stared back at her, the edges of his smile softening slightly.

"Would you please fuck me in the ass?"

The words didn't come out of her in a rush, as she might have expected. Instead, she pronounced each one individually--feeling the weight of each one as it left her lips. For a moment, she and Rory only stared at one another. Then he nodded. A series of small, repeating gestures. Samantha felt an invisible weight drop through her body; falling from her shoulders and rolling through her spine. It came to rest between her legs. There it began to burn. A deep, wet, expectant kind of excitement.

"It would be my pleasure." He stepped forward and took hold of her legs, lifting them back to against his chest. Her feet stuck out just above either shoulder. "How would you like it? Like this?"

"Just like that," she nodded, "That's perfect."

"You said rough earlier," Rory's voice held no reprimand, calm and explanatory, "but this isn't going to be rough. It's going to be slow. Maybe a bit too slow, but slow enough that I feel comfortable." He grinned down at her, "Give me once or twice, and then I'll thrash your ass until you scream." His words made the words slightly joking, but Samantha intended to hold him to exactly that. She felt her excitement rising further at the words; at the explicit improperness of them. "Sound good?"

"Sounds perfect. Now would you please...?"

Instead of answering, he reached out and grabbed the bottle of lube from the face of the table beside her. Cracking the cap open, he went to squirt some into his palm. It ended up being covered by a thin layer of silver paper. He had to unscrew the top and tear it away before repeating the motion. Reaching down, he began to stroke himself slowly--partially to return his slightly lessened erection, and partially to apply an extra layer of lubrication to the condom.

Then, without warning, he reached out and touched a finger against the outside of her asshole. It was his pointer finger. The sudden contact made Samantha gasp--more sharply than she had before. At her sides, her hands clenched. The nails of her fingers pushed against the bottom of her palms.

"Yes!"

"Explain something to me," Rory looked at her as he spoke. But instead of pausing the movement of his hand, he pressed his finger forward. It was still slick with lube, and Samantha gasped more loudly as it easily pushed inside the tight ring of her asshole. He went inside to about the bottom of his first joint before drawing it back and then pressing slowly forward again. The sensation was enough to make Samantha lightheaded, nearly delirious with pleasure, "This is obviously something you've wanted for awhile. Am I right about that?"

"Yes--" she answered his question breathlessly, in the same tone she'd used to pronounce the word earlier. It didn't seem to confuse him.

"Okay," the finger inched forward and backward, "Good girl." She drew a breath through her nose as she felt the tip of a second finger touch the outside of her sphincter; the first one not having withdrawn as the second did so, "So tell me, why haven't you mentioned it before? I mean... Not so much as a please put a finger in my bum?"

"I was..." Samantha felt a slight tightness in her chest, "embarrassed."

Rory seemed to consider this for a moment, and then he nodded. "Okay. Thanks for answering that."

And there it was. No you don't need to be embarrassed. No questions; no pointless speech about trust; no useless assurances or guilt or wounded pride; no confusion that they'd done technically kinkier things in the past. Just a simple: Okay. Thanks.

His second finger pushed inside of her, joining the first. Samantha felt herself stretched slightly as his fingers worked, in and out in an almost achingly slowly rhythm. With his second hand, he reached down and placed his open palm against her pelvis. His thumb stroked downward, nearly reaching the small bump of her clit before drawing back. He looked at her, either for a reaction or for permission.

"Is this okay?" He asked, "Or if we're doing anal is it only anal that day?"

"No," she felt her thoughts spin as the edge of the man's thumb grazed her clit--it was slick, but whether that was from her own wetness or the lube, she wasn't sure, "That's... fuck, that's incredible. You're incredible." A sudden thought struck her, and she opened her eyes, "Wait--you can't... if something's been in my ass, you can't--"

"I know." He chuckled, the sound coming from deep in his chest. Inside of her, his fingers pushed slightly further. Down to the second joint, "I actually have done research, you know. Nothing in your pussy that's been in your ass."

The vulgarity of the language was enough to make Samantha's eyes want to roll back. She let her neck relax, closing them and opening her mouth loosely.

"Third question--is it just the sensation that you enjoy, or is there a bit of a shame-kink I'm sensing here?"

"Fuck," Samantha breathed the word out, wanting to smile but unable to with how loose the muscles of her mouth had gone, "It's... that too."

"So if I were to say, for example... How do my fingers feel in your asshole, you nasty baby? Do you want daddy to finger-fuck you from behind, dirty girl? That would be..."

Samantha groaned. Mostly at the man's words, pronounced loudly and confidently in a way that both made her cringe and sent a flush of heat rushing through her body. But also partially at the way his fingers had begun to move, as he spoke. No longer stretching slowly forwards and back, but with the palm of his hand braced against her entrance and the lengths of them almost flicking forward and backward. Finger-fucking, he had said--and that was exactly what it felt like.

"Oh, yeah." Even with her eyes closed, Samantha could hear the grin in Rory's voice, "This is going to be fun." He paused for a moment, letting the expectant pause stretch between them. His next two words made her body clench. "Beg me."

"Please--"

"No, no, dirty girl. If you want it, beg me for it."

Taking a couple of deep breaths, in time with the thrusting of the man's fingers, Samantha hesitated. Her mouth opened and closed a couple of times. When she spoke, her words were nearly inaudible.

"Would you please put your cock in my ass, daddy?"

"What's that, baby?"

It was his hands that finally brought the words out of her. The slight stretching of her bottom hole around two of his fingers, his thumb brushing over the rise of her clit and down over her labia. The heat of her arousal brought with it small sparks of courage. Grasping at them, she cried out.

"Fuck my ass! I want your big cock deep in my asshole! Please--fuck me!"

"Good girl."

His fingers drew back. Before she had a chance to register how it happened, she felt the head of the man's penis meet the opening of her ass. The muscles hadn't had a chance to close as the head pushed inside of them. Only the first inch, but enough to hold her open. Rory let out a quiet groan as they did begin to tighten, squeezing him with a snug, slightly turning motion. Samantha tried desperately not to roll her hips and dislodge the man, but it was a losing battle.

"Deeper--" she gasped. Once more, he obliged. She felt him slide in smoothly; his length and width filling her to an almost unbelievable degree. Between her legs, his hand continued to stroke over her labia, brushing her clit at the peak of each stroke.

And then, despite his earlier words, he fucked her. Not roughly. Smoothly and powerfully. Samantha's thoughts scattered as the man's cock pushed fully inside of her and then drew back with each motion of his hips. She could feel the tension building inside of her--in her stomach, at the base of her tailbone, in her throat. When she finally collected her thoughts, which had gone running at the first deep thrusts, she realized that she's crying out with every following one. Her voice seems to ignore her mouth, going straight from her open throat and into the room around them.

Leaning forward, Rory reaches forward and wraps a hand around her throat. Not hard enough to be choking, but only the slightly tight grip that he knows she loves. As she feels two fingers press into the soft skin at the side of her throat, she realizes suddenly that they're the same two fingers that had been inside of her a moment earlier. Inside of her ass, and now wrapped around her throat. It should be repulsive. Instead, she feels the tension in her body quickly moving toward a second breaking point. For a moment, she's not sure what will break first--the bones of her fingers that press against the top of the table, or the pressure of her oncoming orgasm.