Anonymity

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A young woman and her boyfriend explore her anal fantasy.
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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?"