The Good Old Days

This was a request, and is in progress, but its a beast of a work, so i am placing it here for now, it is M/F, and deals with a big age gap, taboo sex and workplace sex.

It involves a rather dirty old man of 65, and the main character of 40, office sex, Boss/secretary, power play and power imbalance to an extent, CNC near the end, and a woman happy to help a dirty old Boss relive his glory years.

Here's to the real Babs, and her glory years way back when, of happily bouncing on her bosses cock as the typewriters clacked away, enjoy xx

The Good Old Days

Babs was a beautiful, buxom, curvy blonde, her grandma said she had the kinda wide hips, and curves that would drive men wild in her time. But here and now she was considered a BBW, for want of a better word, Babs just considered herself average pretty and above average weight. She was whip smart, a little quiet, but her friends always sang her praises about how kind she was, and how she would always help anyone.

She was 40 now, and still as pretty most said, bemoaning the fact that the only sign of her age was a few well-hidden snow-white hairs in her pale golden mane. Her blue eyes still twinkled with mischief, and she rarely acted her age. Except when she was at work, then she was ever serious, and harsh on anyone stepping out of line. She had spoken up for bullied staff, and trained many a new staff member across the country.

But now she was being sent to a very rural branch of their company, a tiny office near a small mountainside village. There had been a grand total of four staff, now down to three, one having left to have her baby. One was the boss of the branch, and manager of that area, another was a male staff member who sorted mail and did security, and the third being an elderly lady who was an office clerk. Babs was to asses them and see how the office was running, and if they could be either producing better results, or if they could in fact be closed down.

She had already had the mail guy retired, he was an unnecessary expense, and the older office clerk had stated she would be leaving in two months' time to retire. So, it was up to her if it was past time to close it down, or if it was worth restaffing. It wasn't usually her decision to make, but she had been tasked with going when someone higher up the ladder than she declined, saying that the manager there was 'Old fashioned and unbearable'. So, Babs was not overjoyed at this journey.

She arrived at a tiny apartment, clearly rented as a holiday let usually, it had the usual mod cons and a pretty view of the rolling valley and mountains, even if the decor was a little dated, it was clean at least. The town was beyond sleepy and bordering on abandoned. A few farming families remained, mostly older, and most kept to themselves, she saw no sign of anyone under 50 except for herself and apparently the 30-year-old staff member out on maternity who lived the next town over.

Babs had read the notes, and noted that she wasn't there to try to train anyone, merely to let the manager know that sales needed to be raised more. She was NOT to say anything about the branch potentially being shut down. Though if the manager had any sense, he would have already guessed that his fate was pretty clear, especially as he was verging on 60 himself and likely to be pushed out on 'early retirement'.

This kind of job was her least favorite, as she had to observe and work alongside staff, and it felt a little too intrusive. But work was work and she hoped this month would go fast so she could get back to the city, and her far more active social life there. She had gone to visit the local pub that afternoon to find it closed down, and the lack of things to do boring, thank God for internet and Netflix, she could see a lot of series binging in her future.

She was to report to the office, about a twenty-minute walk on the border of town, at 9am tomorrow, so she spent her time walking, exploring, and grabbing some snacks at the tiny local shop. Finding a farm that sold fresh eggs was the highlight, and she sighed as she settled in for an early night, the early autumn nights drawing in fast and getting so dark it was unnerving. There were two streetlights here, further down the village, and the rest was in pitch dark, the lower floor doorway to her apartment, formerly a garage she thought, had a few fairy lights strung round it as a cute way of finding your way back.

She could hear the nearby river, and occasional birdsong, but other wise it was quiet.

The next morning dawned loud and early, a huge tractor rumbling past at 6am and waking her up as she grumbled and made tea. She dressed fairly formally, recalling the manager being known as old fashioned. She wore a knee length skirt, some black tights, and a smart pale blue button up shirt that may have strained at her heavy breasts, but was made slightly more decent by her smart suit jacket. Her hair was pulled back in a ponytail, light on the jewellery and she was ready with a spray of perfume. Her one concession to wearing formal wear was she always wore her favorite lacy white panties, a tiny bit of freedom in a boring outfit.

She walked down to the office in the cool morning air, carrying a pack of premade cakes she had bought from the city. The office building itself was on what was once an enterprising idea of a business park, now an empty lot with only one other dilapidated abandoned building. It was clearly a fifties or earlier style, blocky looking single floor office building, utilitarian and looking past its time. But the entrance was clean and tidy, the décor and many plants likely a sign that someone had at least tried to pretty up the dour old building.

She came face to face with the older woman, she guessed late sixties maybe, as she welcomed her and told her to take a seat by reception and the 'boss' would be with her soon. The scent of coffee and biscuits told her she was being kept waiting while the so-called boss had his morning nibbles. But she pasted on a pleasant smile, and Mable, the office lady told her she would be leaving in an hour as she only worked mornings as she would likely be gone by the time she was out of the boss's office.

Babs had been in similar offices before, relics that were soon knocked down and replaced, or just knocked down and gotten rid of. But there was an oddly warm sense of nostalgia in the few old typewriters on desks on one side of the room, the only two modern additions a laptop on one desk, and a huge PC on Mable's desk. The wooden desks were as old as the building, the chairs only slightly updated. An actual chalk notice board lay on one wall, unused, and an ancient looking scanner and printer. A fax machine nearby, and most desks still had an old-fashioned phone atop them, cords wrapped around them as they had long since been used.

She tried to imagine what it had been like in its heyday, desks full of paperwork, typewriters clacking and dinging. Phones ringing, likely people smoking as the ancient hint of old cigarette smoke lingered even over the scent of cleaning products. The boss walking past the desks, there were 20 in all, so it must have been a fair-sized place way back when, at least for this tiny area. She wondered at what it would have been like, a different time to hers. Far less kind to women she guessed, as there had been many a boss who would take liberties, it was seen as something normal and accepted sadly.

She was happy she was mostly now in a society that frowned upon sexual harassment. But there was a tiny part of her, deep inside and unspoken, that wanted to go back and see what it had been like. Just for the filthy, very wrong sexual thrill of being with a boss. She knew it was sick likely, and that she shouldn't desire such a thing, and certainly didn't long term, she enjoyed her sexual freedom. But she would love to spend a short time as a woman form back then, perhaps a clerk, who fancied her boss and enjoyed his naughty sneaky gropes and lewd comments.

She was broken from her reverie by a clearing throat, she looked up to see who she assumed was the 'Boss'. He was tall, about six feet, clearly had once been fit but now had a visible tummy that stretched at his trousers. He had bright green eyes, and salt and pepper dark hair, she could see he had once been handsome, but his lecherous look at her breasts and his thick tongue licking his lips instead bought to mind a dirty old man. He coughed, pulling himself together and yanking at his tight navy suit jacket, he led her into his huge office, the desk alone obscenely big.

A huge dark wood monstrosity that took up one side of the room, one of those old green glass lamps on it, along with an ash tray and cigars. He had a bookcase full of books that looked like they hadn't been touched for ages, and a crystal decanter of whiskey beside the books. Old fashioned indeed...she would have to approach this carefully.

An hour later she had told him why she was there partially, to observe sales, and he looked angry but understanding. Then she used her people skills to ask him about the history of this place, he had been manager here for some 45 years he said, since he was 20. He happily showed her photos through the years of the staff, yearly photos for every year he was there, the staff being a big group that soon dwindled after the first twenty years, and was near empty by 2019. It was a wonder they had survived up to now with so few staff. He seemed proud of all of them, and knew them all by name right from the start. It was clear he may be old fashioned and somewhat chauvinistic in his words and manners. But he loved this place, and the sadness in his eyes said he knew exactly why she was here. The photos showed a history of fun and laughter, but also hard work and industry, she saw a man who had started here so long ago, and well expected to end his working life here. He was 65 now, and had planned to work until he was 70, he said, then he would end his days in the very village he was born.

She felt there was a lot more history unspoken, but the bits she now knew made her feel a heavy sense of guilt and responsibility, could she drag this office along for another five years on dwindling business, just to appease an old man? She wasn't sure, but she had a lot to think over. She shadowed him, finding he did the majority of the work, and she was impressed at the end of the day by how much he had done.

As she made them tea and bought it to his desk his eyes looked her over and she shivered slightly, her earlier daydream first in her mind. He tutted at her skirt "You know young Babs, back in my time you would have had a written warning about that skirt, a few inches too short to be decent, such things tempt and incite men after all." Babs laughed at his inappropriateness and told him how it was, but he just shrugged and said he was a man of his time and there was no kind of training that would change that. She tutted back at him and pondered over how he was a potential HR nightmare, yet she had never heard of any complaints from here.

She ended the day with a walk after work, thinking over all that happened, and she bumped into a lady as she walked who struck up a conversation, saying her first job had been there. How she had been a more than eager 19-year-old wanting to work with the handsome Mr Smith. She tittered, her white hair blowing in the breeze as she said how he had been 'cheeky' and yet popular with all the ladies. How she had caused many a mischief just to end up in his office. The innuendo was clear that more than just a scolding had happened, and yet she did not seem angry or bitter about it, rather she seemed wistful. Saying how she had never had so much fun, and never did again once she was married.

Babs was baffled by the encounter, and more than a little turned on, even though she knew she shouldn't be. She went to bed early and nobody had to know if she dreamed of a busy office of time gone by, the sound of the typewriters loud and the smell of ink strong as the boss's hand spanked her bare ass on his desk, before fucking her hard enough she bit her lip, slapping her butt and pulling up her panties to tell her to go back to work. Sitting at the typewriter with her panties soaked and her pussy still throbbing, her cheeks pink as peaches.

The next week was more of the same, most of the time it was just the two of them, and although Boss, or Mr smith as others called him was very much a dirty old man at times, staring at her tits or ass as she worked, at others he was a kind old man with a wicked sense of humor and a smart mind. It was an odd mix that she was still trying to get used to. Then she met an older farmer, who tutted about 'That lecherous old man' in the office, and how he had apparently gotten a few girls pregnant back in the day, but always seemed to slip out of trouble as they were usually married. He reckoned the boss had 'a fair few illegitimate kids out there'. She didn't know what was hearsay, and what was real, but the farmers wife confirmed that way back when he was known as the man to go to secretly if your husband 'couldn't do the job and get you pregnant'. She said many a woman would go on pregnancy leave never to return.

Babs reckoned that although it probably wasn't morally right, as long as it was all consensual there was no real harm there, and she endeavored not to put too much stock in local gossip.

It was into her second week, and after several nights of filthy dreams, that she figured she would test the waters, no harm in having fun as long as she got her work done. She wore a slightly shorter skirt, and noticed Boss as she now called him, and how his eyes widened at the sight. Then as she was making tea, she picked up a biscuit, fellating it quite obviously and licking the melted chocolate from her lips and fingers. He visibly adjusted himself as he watched, then turned away as she stood, he had been very circumspect to be polite enough. But she didn't want that.

She strode over to stand before him, and looked at his crotch as obviously as she could, he froze when she asked if he wanted some help with that. Then moments later he flushed red and nodded, leading her to his office where he sat in his chair. She dropped to her knees and his jaw dropped open at the sight of her, a good 25 years his junior, on her knees and nuzzling at his cock beneath his trousers. His practiced ease with how he opened his trousers and pulled his own cock out said a lot about how this was perhaps a common thing before.

She stroked his thighs and hummed "I wonder how many office women have been in this position hmm? Did you use this as a treat or a punishment?"

His eyes widened, then a slow smirk crawled across his face as he realized, she was getting off on it.

"Maybe I'll tell you some of the things that happened here, or maybe you would like to recreate some hmm? Now be a good girl and suck my cock"

She smirked and nodded, kitten licking at his cock, teasing and light, taking the head into her mouth as he groaned appreciatively. Sucking cock wasn't something she did often, this being only the second time, so she was messy as he tutted at a brush of her teeth, tapping her cheek slightly and telling her to be good and no teeth. She did, and she soon was bobbing on his cock, he had a big cock for an old man, and she struggled to get most of it in her mouth, coughing now and then as he petted her head and grunted. He came down her throat and she tried to gag but he held deep and had a hand on the front of her throat, encouraging her to swallow. She did, and pulled off gasping, the taste was vile, but she had gotten hot over the scenario, her on her knees for an old boss, swallowing his cum as he very vocally enjoyed her mouth and throat.

She was needy when he stood, cock still out, and pulled her up, pushing her over his desk in a motion so practiced she figured it was once a common thing for him. He lifted her skirt, stroking kissing and licking up her thick thighs and ass, palming handfuls of her curves with an appreciative groan. His words were so filthy as he spanked her that she was already near cumming.

"I used to have many a girl like this, my morning cocksucking was usually from my secretary Anne, who always had an eager mouth waiting at 8:30am, sometimes she would already be masturbating herself under my desk waiting. She would make the whole office coffee after she had swallowed my load. But I was always insatiable you see, so by the time 11am came round I would likely have some eager young thing bent over my desk for a good fuck, a spanking, or another blowjob, fuck those were the days."

He had been delving his thick fingers inside her wet pussy in-between spanking her, her tights torn at the crotch and panties pushed aside. She came on his fingers with a groan and he was soon licking up her juices and muttering about how she was such a hot piece of ass, and how she would have been popular at office parties back in the day.

She was panting on his fingers, now on her back, breasts bouncing out of her unbuttoned blouse as he palmed them and suckled on her nipples. He was saying how they would have office parties that ended in group sex, several women sucking his cock, others getting fucked on their desks by other male management. It had been a free for all come Christmas, and he had always loved playing Santa Claus and having the hottest women on his lap.

She moaned and pushed him off and back to his chair, straddling the gigantic heavy chair and his thighs, grinding her soaking pussy against his hardening cock. She was surprised he could still get it up again, but he said he had always been highly sexed. He grasped her hips tight and with his thick fingers pushed his cock inside her, thrusting up and yanking her down. She moaned loud at the harsh stretch, he was thicker than he looked, and he felt fucking amazing deep inside her. She rode him slow and he yanked her down hard, fucking her deep as he could get. She imagined herself a worker, riding the bosses' cock while all the other typewriters tapped away just outside the door, the chance of someone walking in at any minute.

He saw her look at the door and laughed, saying he had staff walk in on him fucking someone before, and depending on his mood he would either send them out, or make them stay and watch. She knew she should find all this wrong, and sick maybe, she looked down at this red cheeked old man, not attractive to her at all really, and she knew she shouldn't be this turned on, yet she was. She had always found the idea of a dirty old man intriguing, but now she was riding ones cock she saw the allure, it was in both the way some would see it as wrong, and also in the way she felt good, making him feel good, helping him relive his glory days. It was likely quite some time since he had sex this wild, having the office mostly to himself, and she felt amazing that it was her giving him this. Though it was far from just for that, she was soaked at the idea of playacting an office girl from back then.

His praise of calling her a good girl just made her even hotter, as he whispered if he could maybe make her a little slut by the end of the month. She slammed her hips down as he groaned and she came hard, squirting all over him as he moaned and came inside her. She wasn't worried, he was old enough it was unlikely she could get pregnant after all. Instead, she shook, hands braced on his chest as she felt his slick wetness inside, a delicious sensation she had never before been brave enough to try. He stroked her hips, wet thick lips licking her neck and sucking a mark as her hips bucked. She pulled off and lay on his desk, panting as his cum dripped from her pussy and he fingered at it with a groan. She told him that was a first for her and he patted her hip, thanking her for such a gift.