Samantha McCowan lay on the sheets of her bed, illuminated only by the glowing rectangle of her laptop screen. Though it was only early evening, her blinds had been drawn closed over the golden glare of the sunlight. A bit of light filtered in from beneath the closed door of her bedroom, but not enough to provide illumination to anything but the floorboards directly in front of it.
Her heart beat fast in her chest, arousal running through her from the curve of her neck straight down to the tips of her fingers; from her chest down to between her legs, where it hung as a slightly damp heat. She wasn’t touching herself. One hand lay in the cool spread of the sheets below her, the other resting comfortably against her chest. A pillow was caught between her knees, tilted up so that only the edge held her thighs open and touched the sensitive folds between her legs.
She had heard her boyfriend enter the apartment about twenty minutes earlier. She didn’t worry about him coming upstairs and finding her. She and Rory had been watching porn together since they started seeing one another three years earlier; it was a mutual hobby, and one that they shared. Despite that, there was one part of her sex life that she had never shared with Rory. For years, there was one genre that she only watched when she was alone. One category that she went to only when the lights were off. She didn’t know why this, out of everything that she and Rory had ever shared, was what embarrassed her.
Anal.
She had been trying to find the courage to discuss it with him for months. Almost a year, now. It had started as something small; a question she couldn’t quite put a shape to that hung in the back of her mind. Like the pattern of a raindrop of a window, tracing the shape of a question mark. Over time, it had grown steadily stronger–one line becoming two, and then a dozen, until finally rain ran down the window each moment of each day. Every time she touched herself, the question came back. Hanging–taunting. Causing small rivulets of moisture to run down the glass of her body and over the skin of her thighs. Each time she opened a porn site, her eyes stayed fixed on the ‘Anal’ category.
But each time she opened her mouth, as she lay in bed beside Rory, to ask him–she froze. Even in the middle of sex, when her mind was foggy with pleasure and her modesty was only something held in the back of her thoughts, something stopped her from asking. There were three occasions which remained with Samantha, long after they’d happened. Once when Rory had slapped her bum while she had been bent over and the tip of his finger had touched the tight ring of her behind; once when he had grabbed her during sex to roll her over and his middle finger had grazed her hole; and once, only once, when in the heat of the moment Rory had missed the hole of her pussy and touched the head of his cock against the other one instead. Just thinking about it was enough to send a shiver of pleasure through Samantha’s body.
She didn’t know why it was something that she craved. Something that drove her more wild than anything she’d experience in her life–more than the submission of bondage that she and Rory had experimented with, more than the idea of sleeping with other people, more than oral or roleplay or bondage. Maybe it was the wrongness of it. Maybe it was how dirty it made her feel, the obscenity of the gesture, the wrongness of the pleasure. It was a double-edged sword; the indecency of the act was what interested her so deeply, but it was also what stopped her from discussing it with Rory.
On the computer screen in front of her, she watched as a muscular bald-headed man held a young woman to the face of a wooden desk. Her hands clutched her thighs, just below the knee. Her legs were raised up, each of her ankles pressed to the man’s shoulders. Samantha watched, transfixed, as the man’s penis appeared through the zipper of a pair of dress pants. She didn’t know what the situation of the video was; except that the title said “ROUGH ANAL IN DETENTION FOR NAUGHTY STUDENT” and she felt pretty confident she didn’t want to know. Only one element mattered to her–only one moment. The moment that the head of the man’s cock pressed against the woman’s exposed asshole, the folds of a plaid skirt bunched up around her waist. With the hand that had been laying in the sheets, Samantha reached behind herself.
As the man’s penis pushed through the woman’s asshole, her finger followed the same path behind her. As the woman on the screen lay back and let out what Samantha was sure was a porn-worthy moan, her hole stretched around the man’s cock, Samantha felt the tip of her finger press against the opening of her own. Her heart raced in her chest. A bit of pressure brought it inside. She felt the muscles of her sphincter screw up, and then loosen as the finger pushed between them. Tightening and then relaxing automatically at the invasion. She squirmed at the feeling, her pulse racing in the side of her throat. A slight curling of her finger made her lips part.
Before she could take it any further, she drew the finger out of herself. The sudden emptiness of her back hole left it throbbing; a strange, dull pulse that she could feel in the cheeks of her bum and the bottom of her feet. Even touching herself there made her feel slightly lightheaded with pleasure–but it was the thought of somebody else doing it that really sent her over the edge. It was that thought, that idea, which had been the source of nearly every orgasm for the last year. It was for this reason that, below the first drawer of the clothes shelf in their walk-in closet that held a box full of their shared sex toys, Samantha had hidden a second box. It was a little smaller than a shoebox, just tall enough to fit beneath the legs of the dresser, and pushed against the back wall. Inside of it were butt plugs of ascending sizes, a small vibrator made specifically for anal, a bottle of lubricant and a box of condoms, a douche-set, and a short plastic string of anal beads. She had used the douche earlier that day, in the shower.
There was one final thing. Something that she had purchased the day before, and spent the last eight hours thinking about. It was a mask. She wasn’t sure what animal the mask was made to resemble–whether it was a cat, or a dog, or a rabbit. In truth, it could only be called a mask in the strictest sense of the word. What it really was was three pieces of leather, held together with small, flat-faced steel circles that kind of looked like the top of screws. It went around her head, with one of the black leather straps fitting snuggly just above her ears and beneath her hair. The rest of it covered the top of her nose, cheeks, and the bottom of her forehead. Large spaces were lefts around her eyes and the top of her hairline. Two flaps of leather stood up around the top; again–vaguely reminiscent of ears, but of an animal which she could not place.
This was the answer, Samantha thought. The answer to the question which had plagued her for the last year. The answer to her shame, and her indecision, and her inability to speak. It was the answer to the desperate need she had felt building ever since that day in bed. Today was the day.
Kicking away the pillow from between her legs, Samantha closed her laptop with a decisive click. Pressing a hand flat against the bed, Samantha swung her legs off the side and stood. As she did, she felt just how wet she had become. The moisture from between the folds of her labia threatened to overflow; she knew it wouldn’t, but it felt as if it should be running down the inside of her thighs in streams.
This was the answer. Anonymity.
Not true anonymity, obviously. Only the felt, lived-in anonymity of putting on a mask and becoming somebody else. Somebody more confident, more self-assured, more… Somebody who got what she wanted.
And she wanted Rory to fuck her ass. Even the thought of it was enough to make the low, subtle pounding from behind her clit match that of her heartbeat.
With the light shining from the desk-mounted lamp beside her bed, Samantha stood and moved to her dresser. Opening the bottom drawer, she pushed aside a small stack of underwear to reveal her folded lingerie. She already had an outfit in mind; a set by Journelle which had cost her a small fortune to order online, but which she thought was worth every cent she’d paid for it. The front of it was black, and sheer enough down the center to reveal the inside curve of her breasts and about half of each of her pert, pink nipples. A pair of straps hugged her shoulders, and opened low down her back. The matching panties were black fabric along the sides, with thick lace along the lower back and thinner–much thinner–lace threading that went between her legs. It was the lace along the back which had first caught her attention. Lace that, when she bent over, pulled apart enough between the carefully black-stitched roses that any observer from behind gained a pretty clear sight of both of her holes.
Pulling the lingerie up around her body and setting it carefully, Samantha moved to the mirror on her dresser. She did a quick half-turn in each direction, admiring the way that the fabric molded itself to her body.
She wasn’t the most shapely woman in the world; she knew that–hell, she wasn’t even the most shapely among her friends. Shapely, she thought, in that her body didn’t hold the classic hourglass shape. She was a bit too skinny for that to be true. It wasn’t really a matter of choice. She’d always been like that. Her breasts were small and firm-looking, with a pair of nipples that took up the majority of each face. Her bum was a bit small, but in proportion to her waist and the thighs beneath it. With a final glance, and a nod, she decided that she was ready.
Moving to the closet, she carefully brought her secret box out from beneath the dresser. From the box came her mask. She fit it around her face, lifting the lightly molded leather around the bridge of her nose and fastening it with the clip at the back. She worked her hair free with her fingers, letting it fall around her shoulders in a single, unbroken dark wave.
She had been right. The mask made her feel… powerful. Today was the day.
The next things to emerge from the box were condoms, two of them just to be safe, and the small bottle of lube. She’d bought the water-based stuff, to be sure it was safe to use with both her silicone sex toys and latex condoms. Holding both in her hand, she glanced at the box for a final time. This time, she left it on top of the dresser, in plain view for Rory to see. Walking out of the closet, she gave herself one last glance in the mirror.
The effect of the mask was startling. She recognized herself–obviously–but not completely. Not at first glance. Not how it really mattered. With the mask, she was somebody else.
Easing open the door of their bedroom, Samantha made her way down the small hallway. The wooden floorboards creaked gently under her bare feet. Reaching the top of the stairs, she began to descend them slowly. Somewhere in the room below her, she could hear Rory typing away at his computer. As he so often did, in the evenings after he got home.
They’d purchased this house with the help of Rory’s parents and a small loan from the bank, about two years ago. Rory worked as an investment banker for a firm called Francon & Siekes, while she taught second and third grade math, as well as filling in for the occasional history or home-ed classes. They both made decent money, him slightly more so than her, and they’d managed to pay back Rory’s parents by the end of the first year. The bank… Well, they were still working on that part. Another eight or nine years, by Rory’s estimate.
The house was a modern one. Slightly narrow, but three stories tall and cleanly furnished. The walls were white, the floors newly-installed hardwood beams, the furnishings alternating between a deep, suave blue and white-grey. They had their own bedroom, a guest bedroom, a spacious kitchen, a smaller living room, a balcony–and Rory’s office.
Samantha saw it as she took the final step off the stairs, turning around them to make her way through the living room. Rory sat behind a black wood, glass-faced desk. Small metal studs ran around each side of it. The desk, Samantha thought, faintly resembled her mask. Her first sight of Rory today, as was the case many days, was behind that desk. He was typing away on a laptop.
His eyes moved intently over the screen, chewing his bottom lip between his teeth as he worked. His hair was dark, nearly as dark as her own, and pushed back from a broad forehead. It had been shaved on the sides, which gave him a bit of an old-English gangster look; something which is family was. Old-English, that is–not gangsters. Not unless you went back far enough. A shadow of facial hair hung around the bottom of his chin and cheeks, but the top of them and his upper lip had been shaved clean. A grey polo shirt was buttoned up to the bottom of his neck. As he typed, she admired the way that the open arms of the shirt stretched ever so slightly around his biceps.
His office was the widest room in the house, which still only made it about twenty feet wide. Behind his chair stood a pair of white couches in an ‘L’ shape, used for seating clients. Above his head was a painting, red and grey paint on a white canvas, which Samantha thought was supposed to resembled close-up shots of poppies. There was a window in the right-side wall, and though a pair of heavier curtains hang to the sides, the slightly sheer white ones had been pulled closed as he worked. It lent the modern, white expanse of the office a subtle golden glow from the setting sun.
Samantha paused at the doorway, leaning against it with one arm in a way that hid what she was holding behind the wall of the office door. Rory glanced up, his eyes flashing the way that she liked–even before he saw what she was wearing.
“Hey, baby. I was just–whoa.” His words cut off in a small whoosh of released air. A pair of eyebrows, slightly thin for the blockiness of his face, rose an inch toward his slicked-back hair.
“Like it?” Samantha asked, pressing her teeth against her bottom lip as she smiled.
“Like it?” He echoed her words, their tone giving her his answer. “Baby, you look like… There’s nothing on earth you look like. Nothing’s that hot.”
“Mind if I come to daddy?” She walked forward, placing her hands on the front of the desk and rising up on her toes slightly, as if to climb on top of it.
In answer, Rory shut his laptop screen with a quick flick of his hand. As soon as it was flat, he pushed the entire thing off the desk. Normally, it would have made Samantha flinch–to see his two-thousand dollar computer hitting the very thinly carpeted floor like that. Today, she couldn’t have cared less. As her hands came down on the table, she saw Rory’s eyes flicker downward. To where the condoms and the bottle of lube were held in her fingers. Opening her hand, she tossed them across the table to him. They slid over the glass, and he had to catch them before they slid off.
Rory’s eyebrows rose once more, as he turned the as-of-yet unused bottle of lubricant over in his hands. He scanned it, and then glanced up at her. The question in his eyes was obvious. Instead of asking it, his voice took him in a different direction.
“What’s the play today, baby? Sexy kitten? Dominatrix?–Sexy kitten dominatrix?”
“Patience,” she smiled at him from beneath the leather strap of the mask, “You’ll see soon enough.”
Rory reached out and placed the bottle cap-down on the face of the table. The plastic made a quiet snap as it met the polished glass. Leaning back in his chair, he gave her an answering nod. Lead on, the nod said. Bracing her hands flat against the table, Samantha lifted herself onto it. Instead of walking, she crawled forward on all fours. She could feel the smooth, cool glass against the palms of her hands, the ends of her fingertips, the flats of her shins and the top of her feet. Beneath her, a matching reflection made the same movements that she did.
She didn’t stop until she was directly in front of Rory. Sitting up, she rose on her legs until she was supported only by her knees and the top of her toes. She turned her upper body slowly, raising her arms and letting them trail down her sides. Her mouth was open a fraction of an inch, her slightly parted lips loose and inviting.
But when Rory reached forward, she caught his pointer finger between two of hers and tweaked the tip. He grinned, his hand retreating back to his lap as he watched her.
She moved slowly, letting her hands play slowly over her chest and sides. Beneath her exploring fingers, the black lace of her lingerie felt slightly rigid. Sliding the middle finger of her right hand beneath it, just above her breast, she pulled it down and to the side a couple of inches. It was just enough to reveal half of her areola, the pink of it darkening in a circle against the pale beige of her skin. Her nipple appeared, and she played the tip of her finger against it until it hardened.
If she hadn’t had Rory’s complete attention before, she certainly did now. She could see the bulge in his beige dress pants where his erection pressed up against the crotch of them. His eyes were fixed between her hand and her breast, and only rose to meet hers when she brought her finger up from her nipple and slid it between her lips. She sucked it gently for a moment, before returning it to her breast.
“Do you know what I’ve been doing for the last hour, daddy?”
“What, baby?”
“I was watching porn.”
“Oh,” Rory’s smile came back–tilting a bit to the left as it opened to reveal a set of white teeth, “And you didn’t share it with me? How unlike you.”
“I wanted to share it with you, daddy–” she let the hand that had been tracing circles around her nipples slide lower, along the front of her lingerie as it followed the slightly bump of her stomach and then further downward, between her legs. Through the lace fabric, she began to massage herself with two fingers. “Like this.”
She inhaled a quiet breath as her fingers pressed slightly upward, bringing the thin lace of the lingerie between the folds of her labia. She continued to massage herself, fingers making small circles. “I’m still so wet. I haven’t cum yet, daddy.” Her breathing became slightly more erratic, the pitch of it moving upward as she touched herself. The sound might have been for show, but the arousal that inspired it certainly wasn’t. Samantha’s heart hammered against her chest, each beat sending a pulse of heat from the top of her arm straight down its length, to where it disappeared between her legs.
“And why haven’t you cum yet, baby? Have you been naughty? Are you being punished for something?”
The sound of his voice, a bit lower than usual, only made Samantha’s pulse race harder. He was feeling her out, she knew–searching her face, her words, the language of her body for some hint of what it was that she wanted this evening. What direction their foreplay was leading in. It was almost enough to make her laugh–he’d never guess what it was that she had in mind.
“I was waiting for you,” she stepped off the table as she spoke. Unfolding one leg at a time over the edge, she crawled into the man’s lap. Her legs straddled his, her hands wrapping around each of his shoulders. He tilted his head up, both of their lips slightly open, separated by the empty space of about two inches. Reaching down once more, Samantha let the back of her knuckles stroke the swelling length of Rory’s cock through the fabric of his pants as their tips stroked against her entrance. “Help me out of my clothes?” She lowered her mouth; not to kiss him, but only to stroke the curve of her bottom lip against the top of his, “Please?”
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.
“Are you going to cum for me, dirty girl? Are you going to cum with daddy’s cock inside your ass?”
FUCK, was she ever. Rocking her hips upward, she felt his penis press against the bottom of her passage as the angle changed. His thumb worked into the soft folds of her labia, pushing them aside to glide down against her clit with each stroke.
Samantha heard herself scream, a moment before registering that the sound would come. Her hips bucked, hands clawing uselessly as the smooth glass of the table as she came. Rory’s hand tightened slightly, causing her thoughts to spin completely out of control. From below, she was vaguely aware that he was coming as well. That inside of her ass, his cock was letting out slow, throbbing pulses. The scream became a high-throated groan as Samantha slowly came down from her second orgasm.
Between her legs, Rory was easing himself free. She drew a deep breath as she felt his final inch leaving her. The sudden emptiness left her feeling strangely weightless; her body floating alongside her thoughts. It wasn’t until he stepped backward, nearly collapsing into the chair behind him, that she realized that Rory was gasping for air nearly as hard as she was.
Pushing herself up, Samantha braced herself on flat hands as she watched Rory push the condom up his shaft. With deft fingers, he tied it closed and tossed it into a wastebasket in the corner of the room. Then he held out his hands, the gesture beckoning her into his lap. Sliding forward, Samantha half stepped and half tumbled onto his legs. She felt a strong hand go behind her back, lifting her upward. Laying her cheek against his shoulder, she blew a gentle breath out against the side of the man’s neck.
“So,” Rory’s deep voice held the edge of a chuckle, “that was something.”
“Something indeed.” Samantha nodded against his skin. She’d finally stopped trembling, but a slight soreness had set in between her legs. She winced, wiggling on the man’s lap and drawing herself slightly closer to him. Raising a hand, she drew two fingers slowly down his lightly haired cheek, “Just… something. Thank you.” Her eyes had been closed, but she opened them suddenly and glanced up at the man’s face. He tilted his own down slightly, feeling the movement against his chest.
“Yes?”
Samantha smiled; a slow-rising, slightly sheepish smile, “How was that… for you?”
“Uh,” he exhaled. This time, a bit of the chuckle did escape him, “fucking incredible.” He leaned down and pressed his lips against the top of her head, “What do you say? Shower?”
“As soon as I can stand,” Samantha nodded. Then she raised her head again, an idea coming to her. “Actually–there is a video I promised to show you.”
“Regular sex, this time?”
“Deal,” Samantha laughed, “As long as I’m allowed to wear the mask.”
This time, Rory’s laughter filled the room from the roof to the ceiling. Samantha felt it travelling through her own body, her shoulders shaking with the movement of his chest and stomach. He nodded a couple of times.
“Baby, after that, you can wear that mask anywhere.”
The smile spread slowly over her lips. “Anywhere?”
“Anywhere.”
Anonymity —- THE END.