Jane [FM] [ANAL]

Jane was a horny woman. She had been since she first noticed the nice feelings when she rubbed her privates against her pillow at a young age. Since that night, she had sought after that sensation with a passion. She fucked her first boyfriend at fifteen, loving every inch of his throbbing cock filling her up and satisfying her like nothing else. She tried anal when she was eighteen and was hooked instantly. The orgasms she experienced when simultaneously probing her tight asshole with a hairbrush and pounding her pussy with her dildo were cosmic. Since that day (she had cum seven times in an hour), she had sought something more.

Jane had had a long string of lovers, each more exciting than the last. There was Peter, who was mild mannered, but hung like a horse (gods, that had felt good sinking into her asshole). Then there was Justin, who took every opportunity he could to eat Jane’s pussy and ass like a five-course meal. Then there had been Thomas, who dominated her life in every way for six months when she was twenty-two. She had been forced to walk around the house naked, ready to be used at his desire. She enjoyed the sex, as she often did, but after a while found the submission to be tiresome, so she broke it off. After him had been Ben, who liked nothing more than to fuck her in the most daring and public places. He was a bartender by trade and had fucked her behind the bar in his pub not once, not twice, but eight times. It had been exhilarating, but there was still something she was searching for.

She decided what it was one night filling her ass with her favourite twelve-inch dildo. She decided that what she really wanted was to fuck someone is a position of power. That was hot. She had once left a pair of worn panties in a teacher’s draw in the last year of high school and had immediately gone and masturbated in the school toilets. She had moaned extra load as well, to make sure everyone could hear. That teacher never mentioned it, or acted as if anything was different, which was disappointing, but she still pursued her dream of fucking someone powerful.

Her opportunity came when she got her promotion. She was a receptionist at a big bank and took pride in her job. Her boss, unfortunately, had been a middle-aged woman called Polly. Jane wasn’t into girls; she had discovered that after fingering a high school friend on a sleepover. That friend had gone on to marry a woman chef, but Jane found that the experience didn’t turn her on at all. Her new job, a personal assistant to Harold Sterling, a big boss at the bank, presented a new opportunity, however.

Her first day told her all she needed to know about Harold. He was well built, with a beautiful crop of semi-long black hair down to his shoulders, and a ruggedly handsome face. He was certainly attractive, but Jane was wise enough to know that that wasn’t everything. Peter, who had a dick longer than Jane’s forearm, and who knew how to use it, had had a face like a rat. Harold smiled when she appeared, his eyes running up and down Jane’s body. “Miss Kellerman?”

“Yes, that’s me,” said Jane, shaking Mr Sterling’s hand. The handshake lingered, and Jane could sense the sexual tensions that she had created already. “Where shall I set up?”

“Your desk is there,” said Harold, pointing to a nice, oak desk just outside his office. Jane put her stuff down and began setting up, satisfied that she had planted the seeds of something interesting.

The first interesting event occurred two days into her new job. Mr. Sterling invited her into his office to talk about a meeting he was having later. As Jane was leaving, she ‘accidentally’ dropped her phone, and bent over to pick it up, thrusting her ass into the air as she did so. She knew it was cliché, but it worked. She heard Harold’s disbelieving exhale at the sight of her ass. She apologised, and left slowly, swinging her ass seductively as she walked.

When Mr. Sterling had his meeting, Jane snuck into his office, and sat in his chair. His laptop was open and signed in, so she had a look. There was a porn tab still open, a video of some teacher and a schoolgirl. She decided to make use of it, and masturbated to the video, plunging her other hand deep into her ass rhythmically as the video played on, a young schoolgirl getting fucked from behind by a burly teacher. She paused it and left when she was done, hoping that Harold would notice that the video had been watched recently.

Sadly, Mr. Sterling didn’t notice. Or if he did, he didn’t show it. Jane decided to start masturbating at her desk, since she wasn’t in a customer facing role anymore (not that that had stopped her before). She started discreetly, but her love of exhibitionism took over, and she started getting bolder and bolder with her sessions. Once she fucked herself in the ass on her desk, after checking that no-one was going to come in. She kept secretly hoping that Mr. Sterling would come out of his office to see her, and take his opportunity, but he didn’t.

Jane kept working him in other ways, though. A flirty laugh here, a touch of the arm there. She once accidentally brushed his cock, and was happy to see that it was hard, and big. Around a month into her job Mr. Sterling walked out as she was teasing a vibrator into her pussy. She managed to hide it under her dress, but it stayed in, set to the highest intensity. She nearly came as he was talking to her, but she managed to play it off. She did come when he was gone, though, and loudly. It was then that she started keeping her masturbations discreet again, but it didn’t take long for her to start moaning. She moaned softly at first at the feeling of her pussy being teased by the vibrator she now kept in her desk permanently, but soon increased in volume, until she was certain Harold could hear her. Then, one day, Mr. Sterling called her in.

“I think you know why you’re here, Jane,” he said, sitting behind his desk, his face stern. “I can hear a lot through these walls, you know.”

Jane felt a flush go through her, and a wetness appear downstairs. He could hear her.

“I just think you should know that this behaviour is inappropriate,” he said, and Jane was surprised to see him getting breathless. He stood up. “I’m not going to fire you, but you should consider this a warning.”

He moved out from behind the desk, and Jane saw that his fly was down. She could see a glimpse of black boxers with a white stain on them and realised why it had taken so long for him to confront her. “I’m sorry, sir,” she said, putting on her best baby-girl voice. She started slowly walking towards him. “Have I been bad?”

“Yes,” said Harold. “But I’ll let you off- “

“I’m really sorry, sir,” she said, putting emphasis on the word as she drew nearer. She was almost touching him they were so close now. She could feel his heat, his nervous trembling. “I didn’t mean to be so loud. Normally I can hide it.”

“Now, then,” said Harold, clearly uncomfortable, but only professionally. She could tell from the bulge growing behind his open fly that he was aroused.

“Oh, sir,” she said, pointing to his open trousers. “Your fly.”

He glanced down. “Oh,” he said, without moving. “Yes, I suppose it is.” Now his dick was almost poking out of his trousers. He looked back to Jane’s face, searching for reaction.

Jane simply nodded and grabbed his dick through his trousers. She enjoyed the heat and weight of it, rubbing it through the sticky boxer material. Harold moaned softly, sitting back on the desk, thrusting his hips and dick outward. Jane stroked and massaged the penis before carefully undoing the boxers, and letting it spring free. It was all she could do to keep herself from taking it in her mouth, eating and enjoying every last of inch of this man’s beautiful cock. She rubbed instead, stroking slowly and rubbing her thumb over the head.

She began to rub herself as well, feeling the wetness soak her panties through. Harold kept groaning at her actions, until she stopped. She stood in front of him, and stripped, first removing her panties and stuffing them, wet, into his mouth. He moaned again at this, and she could see his penis react. Next, she removed her dress in one fell swoop, exposing her pussy lips to his view. She took of her bra to let loose her perky breasts and skin-tone nipples. Harold took the panties out of his mouth and went over to her to suck her nipples.

They stood for a whole minute, Jane stroking his cock, Harold sucking her nipples. Then, Jane stood back, knelt down and began sucking his cock, taking his whole length down her throat, running her tongue over the head again and again. Then, she felt him tense up, and felt his sweet, warm load running into her mouth and down her throat. She swallowed, like a good girl, like Thomas had taught her. She even licked the remains off of his cock.

Harold had to sit down for a moment, breathing hard. His dick was still erect, but Jane had fucked enough to know that men had a cooldown period. Woman could have shotgun orgasms, but not men. She waited, adopted a seductive pose, and started gently fingering her asshole. She moaned deeply, watching Harold watch her, watching his dick get soft, then hard again. Before she knew it, Harold was back for round two.

This time, Harold was in charge. He grabbed her from the floor and pushed her onto the table. He spat on his hand, rubbed it on his now fully erect dick, and said, “Are you clean? Birth control?”

She nodded. She made a point to get checked every three weeks, the amount of dick she took. With that, Harold wasted no time in entering her. Like every other time it felt wonderful, but there was something more. An urgency in Harold’s thrusting, like he knew he could be caught at any time. That was what she was looking for. Fear. Scandal. She leaned into every panicked thrust, feeling his entire dick fill her up completely. She came, violently. She could feel that her face was flushed with blood. As soon as one orgasm had passed, another came, even better than the last. She was in a land of pure ecstasy.

Then it was over. Harold, she noticed, hadn’t come. Jane decided to flip herself over, and present her clean, tight, asshole to him. “Do it,” she said.

Harold came over and penetrated her again. This time he started moaning loader and fucking faster and harder. Jane was barely conscious with pleasure; as soon as he hit the g-spot, she was gone. She had never had it like this, never. She felt enough to feel Harold’s warm, thick spunk fill up her pretty little asshole, and spill out of it. That was only her third creampie, as well.

They kept going all night, taking occasional five-minute breaks for Harold to recharge. Jane came twelve times that night, which was a record. Harold came six, and all over Jane. Two in her pussy, one on her face, one in her mouth, one on her back, and another one in her ass. They both fucked until they couldn’t anymore and lay exhausted on the desk of Harold’s now destroyed office.

“Well,” said Harold, breathless. “I think it’s fair to say you’re settling in well here, Jane.”

“Oh yes,” said Jane, squeezing Harold’s cock affectionately. “I think I am.”

Source: reddit.com/r/eroticliterature/comments/cv7vka/jane_fm_anal