Anal Sex Story 1
The secretary was bent over the desk with her skirt bunched up over her back and her panties pooled by her feet. Her breathing was strained and she tried to look at the wall clock by her left side, praying that her lateness wouldn’t be noticed. Her cheap rayon H&M blouse was pushed carelessly up her chest, exposing her breasts, which had been pulled out and over the top of her beige bra.
Binder clips were cruelly pinching her nipples.
“Keep facing forward,” she heard from behind her, and then the soft whoosh of the rolling chair’s wheels on the industrial carpet. She flinched in blind preparation; she knew something painful was going to happen, but she wasn’t sure what.
There was the clank and rustle of something to the right and behind her. The metal cup and rack that held her office tools. She knew the sound well.
The scratch of the open stapler. The bite of the staple remover. The relentless nip of the binder clips. The smack of the ruler. The poke and scrape of the letter opener. The smooth hardness of the “Received” stamp in her asshole. She knew them all, knew them well, wore the memory of the perverted use of these quotidian implements on her flesh like shameful, naughty undergarments.
“Lift your ass toward me,” said the voice behind her. Not angry, not passionate. Not anything. Its tone could be requesting her to pass the salt.
Swack! She jumped involuntary when the ruler hit the back of her thigh. A purple stripe of pain illuminated her head for a moment and faded, though her right thigh still rang with the hurt.
“What do you say.” The voice intoned.
“Yes, Sir.” She intoned and felt her face flush a bit pink. She had forgotten the complex linguistic rules. When she heard “ass,” she had to respond “Sir.” When she heard “pussy,” she had to respond “Master.” When she heard “you,” she had to respond “Boss.” When she heard “whore” or “slut,” she had to respond “Daddy.” And when she heard none of these words, she had to keep quiet.
It was hard to remember, sometimes. It was meant to be hard. It was made to trick her and trick her it did. It had been created to make her err, and err she did. She often needed correction.
The secretary lifted her ass, tilted it up and back, just a little bit, for that was all she could move. Her pantyhose had been cut from stem to stern; they now hung in tatters around her thighs. Her ankles had been bound to the legs of the desk with packing tape and her long legs spread a wide V on the acrylic desk mat, her hands leaned far forward on the desk’s laminate surface. She had been placed such that she could only move a little bit.
She felt the desk’s center drawer open against her thighs, a cool sliver of metal. She wished she could turn and press her burning thigh against its smooth, chilly surface. She knew she couldn’t, and froze her body, uncomfortably spread and tilted, and felt warm breath on her thigh and the metallic rustle of hands rifling through the drawer’s contents.
“You know,” the voice said, hot breath on her thigh, “your pussy is very wet.”
“Yes, Master,” she said, gulping a bit on “master” as she felt cold air blowing on her slit. The breath continued, a sibilant stream up and down the length of her pussy, and its coldness illuminating exactly how excited she was. The blood in her nipples beat a slow tattoo of pain that seemed to pool, collect, and transform to pleasure in her clit.
“Such a dirty little whore.” The drawer clanged shut underneath her.
“Yes, Daddy.” She said, her voice faltering just a tiny bit. She felt something hard pressed against her pudendum, just at the crux of her slit. Something hard and cool pressing there, waiting. She didn’t recognize it, exactly.
It could be the letter opener, she thought, but then she remembered that she hadn’t put it back in the desk after opening the day’s mail—she remembered seeing it on the desk’s surface as she was getting ready to leave, packing her magazine and her empty lunch containers in her totebag, preparing to switch in to her drive-home sneakers, looking forward to an evening of television and take-out with the boyfriend, a date for which, if her internal clock was at all correct, she was now horribly late.
She felt the metal implement slowly inch its way down her pussy, pressing with an excruciating pleasurable precision. Slowly down her slit it moved, down down down the center of her cunt, pausing deliciously over her clit, passing it, descending to her cunt’s opening, slipping in for a moment, drifting out, sliding with her wetness across her perineum, to her asshole, and back up again. Over and over. The gliding smoothness of the unknown instrument told her how wet she was. The secretary could feel her pleasure burgeon and swell, she could almost smell her orgasm.
Which she knew, from experience, would be delayed, possibly denied, depending on the capricious malice of her Dominator. Almost without her awareness, the secretary arched yet a bit more to meet the touch of the metal, now grown warm with her body heat; she willed it to linger on her clit just a moment more, just a moment, just there, just now.
“You’re not going to come.” The voice said low and casual.
“No, Boss,” she responded with just a hint of sadness. She knew that she wouldn’t be allowed to come, she knew it with every memory of these little experiences, and yet she had hoped, perhaps, that this time it would be different. They had been meeting like this for several months now. It had started when, as a punishment for the secretary’s habitual lateness, she had been summoned into her boss’s office and told that she would be kept late, two minutes for every minute that she had been tardy, and that perhaps this lesson would teach her the meaning and the value of time.
It had begun with her sitting at her desk, not working, just sitting, under the Boss’s watchful eye. A week later, she was late again, and again the punishment and again the sitting, this time with the Boss behind her, standing, and this time the Boss made her sit especially upright. When the secretary’s head dipped, a ruler rang thwack! loud on the laminate beside her hand.
The next time, she had to stand, bent over on the desk. After serving her twenty-four minutes exactly, she went to the ladies’ room to relieve her self; to her surprise, her panties were delicately glossed with her own eggwhite wetness, the soft sea pungency of her desire wafting up to her from between her parted thighs.
And so it had progressed, slowly. From sitting to standing, from standing bent over to this same bent position, ever more exposed, ever more open, supplicant and willing, a slow and slippery slope of submission that inexorably led her to this moment, the close of a day when she had been not-quite-but-almost willfully late, and her present position: kowtowing on the desk, nipples exposed and tortured, panties down, hose rent, her pussy drippy wet from the touch of an unknown office tool, and riding the knife’s edge between fear and desire for what would happen next.
“Put your face on the desk, and turn your eyes to the window.” She did as she was told, feeling the cool laminate under her flushed cheek and seeing that outside the large plate glass windows that it was dark and that the city was lit up like a starlet’s mirror.
“Stay there, slut,” said the voice, behind her and farther away, moving perhaps into the office, perhaps down the corridor of the reception area for her boss and into the open area of the lesser, general office assistants.
“Yes, Daddy,” she said.
She heard footsteps approaching her, coming around her side to the front of the desk; she felt a hand slide through her hair. Soft breath on her ear and the whispered words, “So lovely,” and the feel of lips on her ear. A hand snaked under her chest, pulling gently on the painful clip and then removing it, first one and then the other.
“Your nipples are sore, aren’t they?”
“Yes, Boss.”
“You’d like me to kiss them, wouldn’t you?”
“Yes, Boss.” She gulped. Fingers tenderly rubbed her nipples, and exquisite mix of pain and relief coursed through them, down her solar plexus and directly into her clit.
“I’m not going to.” Her nipples were dropped. Footsteps again, stopping with the Boss behind her. She heard it before she felt it: a swooping cut through the air that ended in a flash of pain on her ass. Then a relentlessly gentle tapping of blows covering her behind with the dull brutal kisses. A punctuation of a thwaking blow, a pause and a delicious scrape of the letter opener’s blade. The ruler rained down on her ass, her thighs, and she could feel them glow and heat, the blows causing her to inhale sharply. And then stopping.
“Take your hands and spread your ass cheeks,” she heard.
“Yes, Sir,” she said, slightly unsure how to respond and fearing retribution, and she did as she was told, taking her round ass in her manicured fingers and spreading it wide, aware that she was exposing the dusky rose of her anus and both shamed and excited that she was doing so.
“Very nice,” she could hear her boss say and then heard footsteps that came closer, then stopping to obscure her view of the window. Before her was her Boss’s waist, a belt, an expensive shirt tucked into even more expensive slacks. Broad hands holding a golf club. A driver.
“You can imagine what this is for.”
“Yes, Boss.”
On hand balanced the club against the desk, directly in front of the secretary’s eyes. Another dipped into the slack’s pocket and withdrew a condom. The Boss unwrapped the condom and slid it down over the handle of the club, retrieved a rubber band from the caddy on the desk and rubberbanded the condom in place. Picked up the club and walked back to the rear of the secretary.
The secretary felt frozen. She did not want the club in her. It looked long and menacing. Her mind raced with what the Boss could do to her insides with it. She may be a tall woman, the Secretary thought, but she had a rather small pussy. And her ass…she willed herself to keep her ass cheeks spread apart with her hands, but she felt herself tense up, nearly to the point of shaking on the table.
A hand smoothed her lower back, rubbing gently over the cleft where her lower back swelled into her butt, tenderly cupping her ass cheeks, soothing her flesh as a trainer would a trembling mare. The hand dipped between her thighs, slipped between the wet-slick folds of her labia, and knowingly rubbed her clit for a few moments.
The secretary felt her body start to relax a bit and to surrender to the pleasure. The voice behind her was whispering sweet nothing, and while the secretary listened for words that she had to respond to, she heard none, and let them wash over her, causing her to relax.
“I’m going to fuck your pussy with this club.”
“Yes, Master.” She responded.
“You want me to, don’t you, whore?”
The secretary paused. “Yes, Daddy,” she admitted as much to her Boss as to herself.
The club entered her pussy, shocking and cold and hard, the boss’s fingers still on her pussy. Her face on the desk, her hands spreading her ass cheeks, her weight on her chest, she had a hard time pressing into the hand, but she pressed nonetheless. Despite the ungainliness of her position—or perhaps because of it—despite the fact that anyone from any office tower could see her illuminated in this position—or perhaps because of it—she felt intense pleasure rush through her, the club so hard that she clenched her pussy muscles around it. Once more, she could nearly smell her cum, her orgasm shimmering before her, a pulsating pleasurecloud, fulsome and ready to release.
The hand stopped, the club withdrew.
“I’m going to fuck your ass now.”
“No, Sir,” she said, starting up, almost before she realized it. “Please. Don’t.”
She felt a hand on her head, she felt her hair yanked and her neck snap back. She felt the warm breath of her boss on her cheek, she heard the voice menacing, no longer dispassionate in her ear.
“You will get fucked in your ass.” The voice said. “You want it. Tell me you want it, slut.”
A pause. The secretary’s breath ragged. “No,” she gasped.
The hand pulled further back on her hair, craning her head uncomfortably. Another hand grasped a nipple between a cruel forefinger and thumb and pinched.
“You will get fucked,” the voice repeated. “You want it. Tell me you want it, you dirty whore.”
Another pause. A lifetime of pauses and the infinite eternal moment that stretches through the barest flicker of time. The sound of two humans breathing ragged and taut. A palpable susurration of wills.
Her body slumped slightly. “Yes, Daddy,” the secretary’s voice small and acquiescent, “I want you to fuck my ass.”
She heard herself being called a good girl, she felt herself being pushed into her previous position, she felt her hands being placed onto her ass, her own fingers pressing into her butt cheeks and spreading them.
She felt something cold splatter on her ass. She felt the slow pressure of the golfclub handle entering her ass, pushing slowly, inexorably, blindly past her sphincter. She felt it glide in, in, in her ass. She felt the pain.
And then she felt the glimmer of pleasure.
“So beautiful,” her boss said from well behind her, standing, the secretary guessed, far enough away to watch the club penetrate her ass, watch her asshole slowly and, almost against her will, open up for it.
A hand crept between her thighs, slipping onto her clit and began rubbing. Rubbing and rubbing as the club entered her ass, paused at its apex and then again as it was almost all the way out of her. The secretary felt the club’s flanged tip brush past her g-spot in each movement, the pleasure-laden pain of fullness and the pleasurable near-absence.
She felt herself very close to coming. She had to hold on not to come. The hand on her cunt was rubbing so well and so effectively. She felt her body wanting to drop down down down into orgasm, to collapse upon itself shuddering and inexplicable there on the desk, but she dare not.
“Would you like to cum?” The Boss asked, the Boss knew—the Boss always knew when she wanted to come.
“Yes, Master,” she moaned, nearly inarticulate, pleasure-pushed almost pre-verbal.
“Push down,” said the Boss, “push against my finger, push against the club, push down as hard as you can, whore.”
“Yes, Daddy,” she moaned, pushing, willing her pussy to reject the orgasm, to expel it out of her, and as she did, she felt it swell, and grow, this tremendous wall and swell, like a tsunami, and she gushed, a slick of girl cum spurting out of her, drenching the hand of her boss, and pooling on the acrylic carpet protector beneath her.
She collapsed on the desk and felt the club being gently removed from her ass. She felt the cool blade of a pair of scissors slicing off her stockings and the packing tape binding her legs to the desk. She felt hands grasping her and pulling her up off the desk, holding her and she felt her boss’s lips on her own.
“That was a good orgasm, wasn’t it?” Her Boss asked. The secretary nodded weakly, more vulnerable now than she had been before, splayed and impaled on the desk.
“Very good,” the Boss said and kissed her tenderly. “Now get on your knees and thank me properly,” The secretary dropped to her knees, pushed the thought of her undoubtedly pissed-off waiting boyfriend out of her mind, unzipped her boss’s pants, pulled them down, her panties too, and happily buried her tongue in her boss’s wet, aching, and swollen pussy.
“Very good,” the Boss said, “very good work…”

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