There is Dee-finitely Something Wrong with the "Former" Secretaries Computer!

Thank goodness IT can work miracles with technology! Come inside for a JAM-PACKED post!

Nothing like a good old-fashioned male boss to 'female' secretary caption, amirite? I wrote this caption up and ended up holding on to it for over a month, as I had other distractions. In that meantime, I've been playing around with the AI program I talked about a few weeks ago .. August 3rd .. so if you'd like to check it out again, just click on the date.

So I think I might highlight a bit of the "fun" I had every few weeks, where I'll post a caption that I wrote, and then show a prompt I created to make a variation of it. And see how well it does in making something unique. To be honest, it is quite the crapshoot, but I have found a few twists that make it intriguing to me. It makes me wonder if the websites they aggregate include Fictionmania or some other sites we've visited in the past.

Yes, it's a bit of a read if you scroll down to the bottom first .. but it's also fun to see the different variations that were conjured up, along with how sometimes they just regurgitate some of the prompts right into the story.

So here's the prompt I used .. and perhaps I added a few things in later, like a son named Damien that was also changed .. but here's the basics:

PROMPT: Martin slowly loses power in the office to his secretary Kaylee, as she starts taking over his clients and gradually transforms him into a female secretary named Marsha in her early 40's, made to sit at her old desk and paint her nails, wearing only dresses, hosiery and high heels, while Kaylee takes over his office and makes him do trivial work that everyone else in the office takes notice, making him embarrassed, yet someone it arouses him in ways he didn't expect. In the end, most of the other secretaries decide to do the same thing, and Marsha has many more female co-workers who used to be male bosses, but are now just administrative assistants dressed up sexily.

Here's some of the "stories" generated .. and I skipped the first few because they really didn't do anything with the story. I'll cut and paste some of the more creative ones.

Martin had been the top executive at the office for years and had put in a lot of hard work to make it there. He was respected and well-liked for his competent work and the way he ran things. Little did he know that he was about to be taken down a peg or two.

Kaylee, Martin's secretary, had ambitions of her own. After noticing his successful running of the office, she decided it was time to try and take Martin’s place. She had plans to make Martin her secretary.

At first, Martin shrugged it off and thought it was just a joke. Little did he know Kaylee was planning something much bigger. She started taking over more and more of Martin’s clients, slowly eating away at his power until she eventually had taken control of his job.

It wasn’t long until Kaylee had transformed Martin physically as well. She began buying him lingerie, bras, hosiery, and high heels and forced him to start wearing them to the office. Those around him noticed the change, but he was so embarrassed he couldn’t bring himself to tell anyone what was going on.

Kaylee also seemed to have somehow taken away his intelligence. Martin was now barely able to do the simple jobs that Kaylee used to do. In an ironic twist, she was now competing with him.

Finally, Kaylee had the ultimate power move - she got Martin to take hormones that enabled him to grow actual breasts. Suddenly, his bras were filled and his coworkers stopped respecting him.

In the end, all of the other secretaries in the office had noticed what happened to Martin and decided to do the same thing to their own bosses, turning them all into sexy secretaries. Martin found it both embarrassing and strangely arousing.

It seemed as though Kaylee had won, as Martin had transformed completely into Marsha, but little did she know that her own ambition was about to bring her crashing down. With all of the new secrets that Marsha had learnt over the months, it wasn’t long until he was in a position of power once again. Kaylee eventually had to leave the company and since then, the office has become a much better place.

Martin is now running the office better than before - and while he still wears lingerie and high heels to work, it’s a reminder of his journey and the lessons he learnt.

That one was interesting because it's one of the few that actually had Martha "winning" in the end. The AI seems to be programmed to be positive and uplifting, as quite of few of the summed things up with, "but with a newfound understanding, the former Martin now understands the challenges of being a woman, and that knowledge made him a much better person going forward."

Martin had been top dog at the office for years. As the oldest and most experienced of all the employees, he enjoyed a position of respect and authority. The other employees looked to him for leadership, and whenever a problem arose, there was always Martin ready to take charge.

That all started to change when a new secretary, Kaylee, was hired. At first, she was just a dutiful assistant, taking orders from Martin and keeping things running smoothly. But gradually, Martin started to notice that Kaylee was taking over more and more of his responsibilities. She slowly started taking on more clients, taking charge of meetings, and independently making decisions in his absence.

And then, one day, Kaylee forced Martin into her office and started laying down the law. He was going to be the new secretary, and there was no room for negotiations. Martin was no longer the boss, he was instead her little submissive. She had control over him, and the only way he'd be accepted in the office was if he followed her orders.

Martin had a choice to make. He could either resist the changes and risk being fired, or he could surrender and comply with Kaylee's demands. Unfortunately, Martin chose the latter, nothing he did seemed to make a difference in Kaylee's mind.

Martin was transformed into Marsha, a forty-year-old woman with long hair, painted nails, and a wardrobe consisting of only dresses, hosiery, and high heels. He was made to sit at Kaylee's old desk, taking orders and doing trivial tasks that the other secretaries noticed and made fun of in hushed tones. Martin's voice had even changed to a higher pitch, and his overall speech pattern had been altered, making him sound like a b!mbo. It seemed as if Kaylee was sucking all of Martin's intelligence out of him.

But at the same time, something inside him had changed, too. Even as he was degrading himself in front of everyone, he couldn't deny that he was strangely aroused by this new arrangement. In some ways, he liked being Kaylee's little subservient secretary.

Other secretaries in the office started to notice the changes in Martin, and before long, they had all started doing the same thing to their male bosses. Soon the office was filled with nothing but secretaries dressed up sexily, while the male bosses were relegated into lowly administrative assistants.

Martin, however, wasn't surprised at all. After all, he had been the first to be demoted and transformed into the office b!mbo.

At this point, I added a few things, like Martin turning into a b!mbo, and that he secretly liked it, even if it was subconscious. This is where I started thinking that the AI has been secretly mining fetish sites as well.

Martin was the envy of his workplace – a young, ambitious executive in the prime of his career. He had worked his way up from a typical desk job, and was now managing a small team of secretaries. He took particular pride in his secretary Kaylee, praising her efficiency and recommending her for promotions.

Little did Martin know that Kaylee had other ideas. She was determined to take his place – and she had a plan.

Kaylee embarked on a systematic campaign to undermine Martin’s power. She started by slowly taking over his clients, eventually taking on clients of her own and calling them directly if they had any problems. As time went on, she crept into more and more of the roles that Martin had once held, until eventually she had taken over the whole of his office.

But Kaylee was not satisfied with simply replacing Martin as head of the office. She wanted to do something more dramatic, and to humiliate him in the process. Her plan was to transform him into her very own secretary – someone whom she could shape to her will.

At first, Martin resisted. He was appalled at the thought of being reduced to such an inferior role. But Kaylee was insistent, and she made it increasingly clear that she would settle for nothing less than total submission.

Martin grudgingly agreed, submitting himself to a drastic transformation. Kaylee used her connections in the fashion industry to transform Martin into “Marsha”, a female secretary in her early 40s. He was made to sit at Kaylee’s old desk, wearing only dresses, hosiery, and high heels – while Kaylee sat at his own desk, taking on his old tasks. His voice became higher pitched, and he spoke in a distinctively b!mbo-like manner, as if his IQ had suddenly dropped drastically.

Martin’s demotion caused a stir in the office. Everyone noticed the transformation, and pointed and snickered when Marsha – formerly Martin – shuffled around the office in her embarrassing costume. However, bizarrely, the humiliation seemed to arouse Martin sexually.

In time, the other male bosses in the office noticed what Kaylee had done to Martin – and they liked it. Each one in turn sought out Kaylee’s help to transform their own male secretaries into subservient female versions, until all the secretaries in the office were in dresses and high heels, relegated to doing trivial tasks while their female bosses took care of the “real work”.

And so Kaylee got her wish, having successfully taken over Martin’s job. But she didn’t do it out of malice – she did it because she admired his ambition, and she wanted to prove that she could do it herself. She had taken Martin’s place, but also won his respect in the process.

That positivity comes back into play with the last paragraph. I do find that so fascinating. do you?

Martin had always prided himself on his success in the office. He was a name that was connected with excellence and expertise and his opinion was highly respected. So when Kaylee, his newly appointed secretary came in one day and started taking over his clients, it both irritated and surprised him. Little did Martin know, a strange transformation was soon to come over him that would changed his life forever.

Martin noticed Kaylee was slowly pushing him out of his own office and giving more and more of his clients to her. Eventually she was handling the entire office, but done so while letting Martin stay put. Little by little he started to become more of the office secretary and less of the office leader, eventually becoming just like Kaylee in appearance.

He was slowly dressed in dresses, hosiery and high heels and was made to sit at his old desk and doing increasingly trivial work. His voice raised in pitch and he spoke in a much softer and girlish tone, giving him the b!mbo effect. It was quite noticeable to his colleagues, who looked at him with pity and scorn.

Putting Martin through this transformation wasn't enough for Kaylee however, who already had a plan to make his metamorphosis complete. She had the scientists who worked for the company use a strange combination of hormones and drugs to change Martin in ways he would have never imagined.

In a matter of days, his manly frame changed into one of a woman in her 40s. His height shrank until he was barely 5 feet tall, his muscular bulk was reduced to slender curves, and even his manhood shrunk to two inches, with Kaylee locking him in a tiny pink chastity cage, to ensure he would stay keep as a female for eternity. She renamed him Marsha and Martin had no choice but to comply to her orders.

Although Martin was embarrassed and ashamed, there was something inside him that was strangely aroused by his new situation, making him ashamed of his own feelings.

Word of Kaylee's mesmerizing work on Martin spread around the office and soon all the female secretaries followed her example and changed their male bosses into females, all dressed up in hosiery and dresses and all just lowly administrative assistants.

Martin, now known as Marsha, accepted the reality of his situation and embraced his new identity, letting go of his past and beginning to enjoy his new life. He had no idea that the transformation Kaylee had unleashed in him would be so liberating.

Life was never the same for Martin, or Marsha, ever again.

By this one, I had put more physical changes into the prompt, and chastity too. I love the verbiage that the AI created, and it's probably about as close to a Dee caption as we will see here. That ending is SUCH a zinger!

Martin had climbed the corporate ladder over the course of a decade, working hard and honing his skills to get to the top. He had finally landed the coveted position as CEO of a large technology company. After settling into the office, he hired Kaylee as his secretary, feeling comfortable with her friendly and efficient demeanor.

Little did he know that Kaylee was far more than she appeared.

Once she was established in the office, she began slowly taking over his clients and leading them in directions he had not intended. Martin felt powerless against her strong, imposing will and he found his confidence waning while she quickly took control of the company.

Soon, Martin found himself in a position he could never have imagined - dressing up as Kaylee's female alter-ego, Marsha. She made him wear only dresses, hosiery and high heels as he sat at Kaylee's desk, doing trivial tasks meant to humiliate him in front of his staff.

With each passing day, Kaylee seemed to absorb Martin's intelligence and gain more power over him. Marsha's IQ dropped, barely able to do the job that Kaylee used to do. It was like Martin was slowly losing himself to Marsha.

Eventually, Kaylee began using her power to tamper with Marsha's body. With the help of the company's scientists, she caused Martin's breasts and hips to grow larger, his height to diminish, and his manhood to shrink and be encased in a chastity cage.

Before long, word spread about Martin's transformation and the other executives began to feel the same fear Martin had, for it seemed that Kaylee had set a newfound trend. The secretaries started conspiring against their male bosses, turning them all into feminized subordinates in no time.

Devastated, Martin realized that the absolute power he felt when he was CEO was gone, replaced by the realization of how vulnerable he was in this new world.

But when he learned that Kaylee had infiltrated his son Damien's high school and taken control of his life too, Martin felt even more helpless. His son was no longer the large, ruggedly handsome varsity quarterback, but a petite, perky cheerleader named Dee Dee who was dating Kaylee's daughter.

No matter how much he wanted to, Martin knew he could no longer protect the ones he loved. He was condemned to a life of submission.

It was then that Martin truly felt what it meant to be powerless.

That's another great closing line! Now we are getting to the fun stuff. the AI is getting downright evil .. gotta love that! We'll leave you with a few more so that you can hopefully enjoy the subtle differences of each short story.

Martin had been a successful, high-powered man. He was the president of his company, his employees admired him, and no one could put a foot wrong in his presence. He was a powerhouse in the office, respected and feared. But all of that changed when Kaylee was hired.

Kaylee was beautiful, intelligent, and had a knack for manipulation. She made sure that Martin was aware of her presence and eventually attacked him through his weaknesses. She slowly took over Martin’s clients and poached them away, one by one, until he was pushed into a corner with no one to turn to.

Martin’s power began to diminish, as he soon became relegated to his old secretary desk, where his only job seemed to be painting his nails, wearing provocative dresses, hosiery and high heels. His co-workers took notice of the change, and it greatly embarrassed him. Yet surprisingly, he found himself aroused in ways he had never felt before. His voice started to sound more feminine, his speech had a distinct b!mbo-ish quality to it, and his IQ seemed to drop significantly.

Kaylee had absolute control now, and she was determined to transform Martin even further. She used her newfound influence to have Martin’s body physically altered, enlarging his breasts, hips and butt and shrinking his height until he was unable to reach 5 feet tall. To add insult to injury, his masculinity also diminished, leaving him with only 2 inches erect.

Martin felt humiliated and powerless as Kaylee revealed her plans to other secretaries, convincing them to do the same to the male bosses in their departments. Pretty soon, both men and women were relegated to administrative roles, with only the former men wearing colored hosiery and suggestive outfits.

The final nail in the coffin happened a few weeks later when Martin found out that Kaylee had infiltrated his son, Damien’s high school. The large, athletic jock was now a 5’1” petite cheerleader going by the name of Dee Dee. To add more insult, Dee Dee was dating Kaylee’s teenager daughter. Martin felt as though he had been replaced. His son, in a way, had become Martin himself.

He had been completely powerless, crushed by the force of one woman. But the humiliation hadn’t ended there. He learned one cold, hard truth that day: Kaylee had not only taken over his life, but his mind, too. She had removed all of his manliness and created a b!mbo out of a once successful man.

and one more for the road:

Martin had always been ambitious and driven, and as such, he had become CEO of his own company. He had worked hard to become the successful man he was, and he was not about to let his throne be taken away from him.

But when a new secretary, Kaylee, was hired, things began to change. Martin soon found himself slipping from the top and losing power to Kaylee. To his dismay, Kaylee began to take over more and more of his clients and duties, slowly pulling the rug from beneath his feet.

One day, Kaylee called Martin into her office and informed him that for the good of the company, she had decided to apply a new policy - Martin was to become the new female secretary, named Marsha, and take Kaylee's place.

At first, Martin protested, but soon realized that it was in the best interest of the company. But he hadn't expected that Kaylee also expected him to dress up in only dresses, hosiery and high heels and take his old seat at Kaylee's desk.

Soon enough, the other employees noticed Marsha's transition and Martin found himself being looked upon in an embarrassing way. Strangely though, amidst all the humiliation and embarrassment, Martin found himself somewhat aroused by the changes happening to him.

Little did Martin know that the changes would not stop there. Kaylee gradually started to absorb Martin's intelligence and she was slowly making him dumber and dumber. As Marsha, his manhood shrank and eventually disappeared, replaced by a tiny pink chastity cage. His stature also began to dwindle, until he was barely 5 feet tall. The icing on the cake was the fact that Marsha's body was now modelled with large breasts, hips and buttocks.

And if all of this wasn't enough, a few weeks later Martin found out from his son that, due to Kaylee's influence, his son Damien was no longer a large football player, but a petite and perky cheerleader named Dee Dee. To make matters worse, Dee Dee was dating none other than Kaylee's wild and dominate daughter.

Martin was ashamed that he had let this transformation happen and that he had let his son, whom he had once groomed to be a strong figure like himself, succumb to such banality.

Sadly enough, Martin's story set an example and many other secretaries soon followed in Kaylee's footsteps, turning their male bosses into the lowly sexy secretaries that Martin had become.