A Woman on the Hunt


An exercise in AI writing

By Christopher Leeson

Detective Rick Watson had been working on the same case for months. He had been put on the trail of Jason Morretti, a criminal mastermind operating out of New York City, but he had been continually frustrated in turning up the evidence needed to put the man away. Alas, a minor raid that he had been unexpectedly called in on had brought disaster. The raid had aimed at shutting down an illegal bio-lab operating in upper New York state and had been very hush-hush because of its suspected ties to traitors in the US government. The operators triggered a self-demolition rather than have it captured.

The explosion had caused Rick Watson to be washed over by a biological soup. This random concoctions of cultures had sent the detective to a hospital where he lay semi-conscious for weeks. To say it bluntly, whatever it was that drenched Rick, it had progressively transformed him into a woman.

This was all new to the doctors who treated him. When he finally came full awake, Rick was astonished. The department was willing to pay for his restorative sex-change surgery, but they also explained that such would put him out of action for a year. The more Rick thought about that, the less he liked it. He -- now a she -- was determined to solve the case that she was working on. The department couldn't afford the disruptions that a public disclosure of the accident would have brought on.To prepare Rick to return to work, the department provided her with the paperwork for a new identity. Rick chose the name of Rita Holmes -- a joke in reference to her real name of Watson.

With the aid of senior officers, Rita evolved a new plan. The woman she had become was very fine looking. She would present herself to the Morretti gang as a spoiled trust-fund brat and start working undercover on the edge of Morretti's criminal underworld, seeking every day to get closer to it.

Despite her hard work, Rita, was finding this case his/her toughest yet. It really bothered her that she hadn't been able to deliver the goods as a man, and it only seemed harder to do now that she was a woman. Shaking off her doubts, she set upon her goal with steely determination. She had already spent months studying the criminal’s past, his contacts, and his habits. What she needed to do at this point was to learn how to impersonate a natural woman.

First, she met with a voice coach who helped her change the way she talked. She learned to speak more softly and use words and tones that evoked the feminine. As a rich kid, she had to dress like one, and that meant learning a lot about women's hair, makeup, and clothing. Finally, Rita felt ready to start attending the events and affairs that Morretti normally frequented.

At first, Rita kept her distance from the man himself, easing herself into her role by observing gang members from the sidelines. Little by little, the infiltrator started to make connections with some of the people who regularly attended the events. With them she established her identity as Rita Holmes. These efforts allowed her to get invitations to gatherings from people whom Morretti knew. At the affairs, she manipulated her contacts into introducing her to the powerful Syndicate man.

For a crook, Morretti was genial. Nonetheless, he proved out a distrustful man who kept any new acquaintances at arm's length. Becoming frustrated, Rita decided to see if by acting more boldly she might establish an actual social relationship with her target. Up to now, she had been conducting herself like a proper young lady. That was getting her nowhere. She came to believe that she had to make some drastic changes in both her manners and her appearance if she was going to make an impression on a man like him -- a man who already had on call all the women that any man could possibly use.

With the help of advisors called in the NYPD, Rita modified her style. Hardest of all was acting convincingly like a young woman on the make. She had her coaches teach her what to do so as to seem more outgoing and adventurous. The detective wanted to show the criminal that she was someone who was willing to pursue risks and was not afraid to take chances.

Even though the new Rita was very different from the old, Morretti warmed very slowly toward her, but after a few weeks he began to take more and more notice. He approached her with increasing frequency, asking questions about her life, her likes and interests. He gradually began to display a personal interest in her.

Eventually, the criminal kingpin began to open up to Rita. The big moment was when he invited her to a garden party where, she knew, many of his cronies would be gathered.

Unfortunately, the event proved uneventful. Morretti remained superficial in his attentions. He clearly was not trusting her to any great degree. Still finding herself blocked, Rita decided to take a drastic step. If she encouraged the gangster to make sexual advances, that could lead to intimacy -- which might provide new ways to manipulate him. She mainly wanted to make him comfortable enough to start unloading his worries and troubles upon her.

So Rita put her plan into action, she crafted a third metamorphosis. She asked her advisors to provide her with more dresses that fairly screemed "sex." Rita surprised herself with what she ended up agreeing to be seen in. She was acting on a hunch. Having been a man herself, she had a good idea what a tuxedoed thug like Morretti might enjoy seeing a woman wearing. He pumped her acting coach for ideas how to show off a wilder side and worked with an acting coach to learn the methodology of flirtation while using subtle body language which was calculated to rivet the attention of a randy male.

The next time she got close to Morretti's orbit, Rita was sporting the most provocative sort of clothing. It pleased her that Morretti responded very positively. She talked to him in a coquettish manner and her eyes didn't chasten him when he he very obviously admired her cleavage. She was embarrassed, of coure, but somehow managed not to allow it to show.

Her tone and her movements encouraged him to boldness and eventually the gang boss made his move. He touched Rita's arm in a way he had never done before and asked her out for dinner.

Rita realize that such was a big step forward. Though the intensity of his new interest incited her anxiety, she had been working toward this and had no option other than to agree to go out with him.

The next day, Rita and the criminal went to the Blue Lagoon Dinner Club. Rita was provocatively dressed to the max and still nervous, but she managed to keep her cool. She talked to him in a friendly manner and convincingly laughed at his jokes. In fact, the change she had brought about in Morretti was such a significant one that she started to wonder whether she didn't have the potential to become a good actress.

At the end of the night, the criminal was talking in a general way about how his illicit operations and how high his very lucrative federal connections ran. Rita was relieved at having won a degree of the man's trust and now she could finally start digging the ground close-in to him to find the evidence she needed.

Eventually, Morretti starting asking Rita to travel with him. She accepted every invitation, although she absolutely didn't like his company. She had no doubt that if he ever guessed what she was actually up to, she would disappear without a trace.

Rita was now actually arriving at social gatherings escorted by Morretti. As time went on, she was invited to more and more private events. Most of the guests at these affairs were criminals whose mug shots she had seen before. Others were politicians whose criminal activities, many people knew, were being continually covered up by the FBI and Justice Department.

Finally, after months of hard work and preparation, Rita was able to congratulate herself on infiltrating the criminal’s inner circle. Yet she was still somewhat on the outside looking in. She was always kept away and watched when Morretti met with his major lieutenants. She needed more access than this. She had to go in all the way into his confidence or else she would ultimately fail. Now it was time to step up the heat of their supposed affair.

It almost surprised her that he had not already been asking for sex from her. She began to wonder if Morretti wasn't one of those types who went everywhere with beautiful women as a ruse to cover up the fact that they were impotent. Part of her hoped that Morretti was one of the weak tribe, considering her situation, but if he were, she might never get past his final guard.

While she was still wondering about how things really really stood, there came an evening when Morretti called up to invite her to his penthouse, which he had never done before. When he picked her up in is limousine, the look in his eyes made Rita very worried about what was going to happen next.

By the time they arrived at the criminal's lavish digs, Rita's stomach had tied itself up into tight knots. She had been subtly offering her body to this man for weeks. Was he finally going to accept the offer? Did she really want this? Rita nearly leapt from her skin when the man reached out and touched her breasts. Whatever had restrained him before, that restraint was gone now. The fact was, there was the very real possibility that she was going to be asked for sex. The whole idea was repulsive but, also, oddly exciting. Up to now Rita had thought of herself as a male who only looked like a woman. Something was warning her that she shouldn't be here, but because of the importance of her job she couldn't run away.

Suddenly he scooped her up and carried her to his bedroom. The sensation of being treated like a cave woman ran through her bloodstream and almost made her cry out. To do or say the wrong thing could destroy everything that she had been working to achieve. Rita steeled herself for surrender. She knew that whatever Morretti wanted to do, she had to encourage him in it and then let it happen.

Morretti laid her on her back and, a single piece at a time, he took off her particles of clotheing, touching and stroking her far more than was necessary. Rita, though shivering, let him be the boss, be the primitive man, and do what he wanted her to. Rita had been rendered entirely nude before the gangster started taking off his own expensive duds. She waited with her fists knotted, absolutely determined to accept any kind of indignity in order to make her mission succeed.

Suddenly he entered her with the help of his fingers. Desperately, she fought to remember what she had been taught about faking an orgasm.

That night, Rita found out more about being a woman than she had so far learned from reading or from her advisors' briefings. Rick had been with women intimately, mostly short-term girlfriends and call girls. For all his sophistication, he had never suspected the gulf of difference that existed between entering and being entered.

When morning came and Rita was driven home, she realized that the night's adventure had come and gone without her having gathered any new evidence. But yet she hoped that what had happened might yet lead to new opportunities. As her trembling hand unlocked the hotel room door, she was determined to cultivate this relationship for all it was worth. Although the department hadn't actually told her to do it this way, she thought they would approve of it without actually saying so. Politicians were always looking over their shoulders and they wouldn't have dared to authorized a female agent to have sex with a gangster. Rita couldn't disguise from herself the fact that her experience, if it would be for good or ill, was all of her own making.

She was encouraged that she had, after all, done the right thing when a call from Morretti had come in with an invitation to go with him to a nightclub that same evening. She answered with all the enthusiasm that she could counterfeit. She didn't like Morretti. Most of the illegalities he was involved in were disgusting. Despite that, she wasn't in a panic about possibly having more sex with him.

After dinner that evening, they went back to his place where he poured out two glasses of wine. Rita was nervous but concealed it well; she was mentally prepared to give the man anything he wanted. She was the trap and he was the rat.

Astonishingly, when she was spread-legged and being treated like a piece of asphalt being pile-driven, something happened. It was like she was a pistol and he had cocked her and pulled the trigger. She was unable to hold back and she came! It was not a fake, but a real come. The more he did, the more she came, repeatedly. She suddenly felt like she had become a different person.

Despite the confusion of the moment, Rita disguised her distaste for the man by pretending that he was someone else. To get away from the reality, she forced herself into a fantasy -- a fantasy that he was only a man she didn't know, one whom she had picked up in a bar. It helped. Now she could better appreciate the mighty tool that had made her into an ex-virgin just the night before. Concentrating on the simple physical pleasure of all, she made no fuss and she made no mistakes.

In the morning Morretti's houseboy served them breakfast. Rita again wondered again if she were not an excellent actress, seeing as how she could look at the man's face across the small table without cringing in shame. "You're one hard bitch, baby," she told herself.

Morretti's chauffeur dropped her off at her hotel and she hurried inside, no long able to hold back her shaking. It bothered Rita on some level that she hadn't been more greatly disgusted with either of her sexual encounters. What kind of person was she on the inside? It frightened her to think about it.

Detective Holmes typed her report to headquarters into the high security address she used and then did nothing special for the rest of the day. Before this, Rita had gone to bed when she was alone wearing a set of pj's fit for a middle aged housewife. But tonight, on impulse, she put on a little nightie that the department had provided. She stood gazing into a mirror, wondering at the girl that the glass reflected, pondering who and what that person was and where her life was going.

Rick had always thought that he looked pretty damned good as a man. Yet, more and more, the idea of ruining this of hers body with an operation was grotesque. The "sex-change" offered her was only cosmetic. Hormones might make her face hairy and let her put on a little more muscle, but it wouldn't restore the virile man she had been. Of what good was a lifeless dick made of rubber? On the other hand, she still knew so little about being a woman.

While following the case she was on, she had not been living as most women lived. She wondered if she would be less reluctant about having a rubber dick if it turned out that she hated being a female. Regardless, she would have to stay a woman for a while. She had already been told that she would be a valuable courtroom witness against Morretti. To avoid the press going crazy, she had to stick to the story that she was a police officer who was a natural woman. A case that was as large as Morretti's might take more than a year to bring to trial. That period of time would at least give her a some latitude to find out what womanhood really meant.

Rita spent a good deal of time in Morretti's company over the next several weeks. He learned about some of his kinks. He never asked her for oral sex for some reason and in place of that he often wheedled her into dressing up in various costumes, some of them being actual Halloween costumes from Leg Avenue. The ones he liked best very short and very tight. There had been a bimbo Cinderella, a bimbo saloon girl, a bimbo Steampunk bitch, a bimbo super heroine, and many another. In the end, whatever she was wearing, it usually came off as soon as he dragged her to bed in the heat of excitement.

But while Morretti was having fun with his fantasies, Rita was gathering in evidence, mostly from filling his penthouse with surveillance devices. Finally, the day came when the department decided they had the criminal kingpin dead to rights and arrested him at his downtown office.

Rita felt depressed and ambivalent. Though Morretti was bad, he hadn't treated her badly. Nonetheless, he was an evil man working with bad people and he certainly deserved whatever he got.

Just as anticipated, Morretti's actual trial would be held off until the next year. Rita's captain got around to asking her whether she could use a rest following her long and unnerving experience. She said that she would be glad to take a leave of absence from the police force.

"I suppose your nerves are worn to a frazzle," the captain said. She agreed without going into detail. "You already had a psychoanalyst," the officer said. "Maybe you should spend your time getting your head back on straight." Rita hadn't really replied to that suggestion.

She left New York soon after and took an apartment in Richmond. Rick had liked Richmond and had gone to college there. Rita had made no real plans so far and simply wanted to rest and think. She hadn't had sex since before Morretti had been taken into custody. It was strange thinking back to when she had been his pretend girl friend. It hadn't been traumatizing to have been treated like a woman being frequently banged by a man. It was only the fact that her lover had been detestable that made those memories unpleasant.

With nothing special in mind, Rita had brought to Richmond the whole set wild outfits that she had worn for Morretti's enjoyment. This faithful night in Richmond, she found herself putting on a very short, very tight red dress that was set off by very high heels and lots of makeup. She was all dressed up before she realized that she actually felt like going out. But where would a woman alone go? Well, a singles' bar was the obvious answer. She wasn't sure if she was going to be looking to meet up with a man or a woman. She hadn't tried being a lesbian yet. That kind of switch might be interesting, she thought.

So it was a hot chick dressed to the nines who stepped into the bar. Its interior was a little tacky and shadowy, except where there were plenty of colored lights to set the mood. As soon as Rita stepped over the threshold, she felt her bare skin tingle -- and she was showing plenty of bare skin. It was something like what Rick used to feel when stepping into a dangerous place. She looked about and saw that every man in the room was staring at her, while pretending not to.

Wimps! Rita was glad that Rick had never been a wimp. Morretti, also, hadn't been a wimp.

And maybe that was the only quality he had that she could honestly say that she liked.

Rita went to the bar and ordered a sangria. She ignored the men who were blatantly staring at her legs. If they were so interested, why didn't they just step up and say hello? she wondered. Hell, did they suppose that a woman who walked into a bar wearing a dress as short as hers didn't want her legs to be looked at? But yet she couldn't forget that Rick had been told by several women that it was sexist for a man to stare at a woman, no matter how she chose to dress.

"Women are crazy," Rita muttered to herself. She hoped that nuttiness wasn't hard-wired into a woman's genes. For as long as she had to be one of the opposite sex, whether that should be a year or for the rest of her life, Rita Holmes now vowed to fight hard against the possibility that she might become as crazy as the run-of-the-mill, bar-crawling femme seemed to be.

Suddenly, a man took the stool beside her and asked if he could buy her a drink. He introduced himself as Bob. Rita looked him up and down. This guy Bob filled a clean suit very well and came off as sexy in a mannish sort of way. After several drinks, the stranger suggested that they go to come to his motel room and she said yes.

Only then did she realize that this particular bar trip wasn't going to end with her spending a night with a girl.

When the two of them arrived at his motel room, Rita's heart was racing. This was the first time she had ever gone with a man as a woman just because she wanted to have some company. She was suddenly worried that because she didn't have a role to play, she wouldn't know what to say or do as part of a normal man-woman couple and would make a fool of herself. One good thing about it, though, was that a mistake probably wouldn't end up with her being killed, as always had been possible with Morretti.

Bob's kisses came on hard and fast. They were electric and Rita felt herself melting into him. Strong, masterful hands began undressing her. He he got her nude very quickly, leaving her with just a thong panty. Already Rita had come to realized she very much liked wearing thongs under very short dresses. It made her feel naughty, and she very much enjoyed the naughty feeling.

Her body came alive as Bob's fingers explored her curves. He led her to the bed and began a process of touching every part of her body with every part of his own. After he drew off her thong, they made love with slow deliberation. Rita was enjoying touching the man as much as she had ever enjoyed touching a girl as Rick. When Bob took full command and delivered the real McCoy, she was surprised by the power and depth of his penetration. She was suddenly jealous of the woman who would finally marry this guy.

Or maybe he was married already.

If so, that didn't matter to her. After tonight they would never meet again.

When they lay back on their respective pillows, Rita made a mistake in her dazed state of mind. Bob had taken her by surprise by asking for oral sex and she responded "No," without thinking. Worse, she followed the negation with an eye expression that delivered the message that she meant it.

All this had been done reflexively and without a pre-planned thought. But she quickly remembered how Rick had felt as a man whenever a woman had had the audacity to turn him down over such a little thing -- not that Rick had been small, or course. Rick had been irritated; would Bob be angry with her now? She might have saved things by changing her mind and apologizing, but the manhood still inside her kept her from saying a word. It became so very clear that her refusal had taken the air out of the evening. After some awkward chitchat, Bob asked if he should call her a cab. Rita, realizing that their tryst had gone up in smoke, said yes. Before they parted, she was hoping that he would speak up and suggest they have another meeting.

He didn't.

Then Rita went home. Except for the less-than-sweet ending to the night, she could not help feeling a sense of accomplishment and satisfaction. She had gone out, moved by the impulse to find a new lover, and had found one.

Nonetheless, the incident had left her staring up at the ceiling long and hard, thinking about oral sex.

Given Bob’s reaction, would she ever again dare refuse the next bed partner she found? If he was a bum, it didn't matter. The unfortnate risk was that she might encounter a guy as attractive as Bob had been. Rita suggested to herself that being a little more cooperative with a bed partner's needs might make a enjoyable tryst last a little longer. Longer was better, but she remained very conflicted about where to draw the line wit a man on the make.

A part of her was tempted to not be such a prude and do the deed once as an experiment, just to learn what it felt like a real naughty girl feels. A fair number of women had gone French on Rick and the memory of those experiences was nagging at her, making her curious about what it felt like to be a bad girl with a man.

Even if she did the deed once, she wouldn't have to do it twice, she told herself.

Not unless it turned out that that going down on a man wasn't as bad as she thought it might be.


Rita still had more than a year to wait for Morretti's trial. She hoped that that span of time would be long enough to help her decide if she would want to fit herself out with a rubber dick back in New York or not. She wasn't drawing full pay on while leave and Rick hadn't saved very much. It was starkly clear to Rita that if she didn't get an sustaining income, she'd have to move into some kind of cramped one-room place and she didn't want to do that. She had to get a job.

That forced her to think about what jobs women were filling these days.

Actually, she already knew. The barriers were down. If a female could find a boss willing to hire her, she could do almost anything. But this wasn't just about finding work. It was a chance to find out about herself. She wanted to live this next year exactly like a life like a real woman and maybe it would be best if she explored that lifestyle by taking a woman-type job. Teaching? Nursing? Running a cash register? Not her style! What she needed to do was to think about what she most liked about being a woman, and then see how she could turn her liking. That way she could gain a real understanding about the realities of womanhood.

Then again, modeling was a popular career and few women seemed to be able to enter it. If for some she didn't get to walk the runway, what other woman-type jobs might be tolerable?

Acting? She had already been wondering whether she had acting talent.

But everyone knows that girls hustling for acting jobs usually had to survive for a long while by taking waitress jobs -- and most of them stayed waitresses for the rest of their lives.

Then again, Rita knew that cocktail waitresses got to wear some fantastically sexy outfits right under the eyes of hundreds. And they were the center of attention in any club room.

Honestly, cocktail waitresses was something to think about.

The big question besetting Rita was whether she wanted to stay with the NYPD -- with any PD -- after the big trial was over. The more time she spent away from the department, the more doubts she had about going back. She already knew that she liked sleeping with men, but she was darn sure that she didn't want to sleep with any more gangsters!

She couldn't shrug off the feeling that some instinct was warning her that her old job had become like a pair of pants that had gotten too small, a garment that was never going to fit her properly anymore?

Rita had no objection to tight clothes, but crime detecting was one tight garment that she didn't feel so eager to get back into.

The end

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