Loss Prevention                        by: Alyssa Davis

 

The Help Wanted ad said, "Retail security position open at Macy’s Department Store. Experience necessary." Tommy was ready for a change and this job interested him, so he proceeded to the personnel department, now referred to as Human Resources, at Macy’s where he filled out an application and was immediately scheduled for an interview with Louise Clark, the manager of the Loss Prevention Department.

"Hello Ms. Clark, I’m Tommy Andrews. I’m interested in the position you advertised for store security."

"Hi Tommy...please call me Louise. Have a seat."

She was an attractive woman, mid-thirties, tall, slender, well dressed, long dark hair perfectly groomed. Tommy studied her appearance, a habit he had acquired by his training of closely observing people.

"I see that you have experience in retail security at several of our competitors. May I ask why you’ve moved around?"

"I wanted diverse experience, and also, I wanted more money. I felt it was the quickest way to get both." Tommy tried to be honest without sounding flippant. He wanted, after all, to make a good impression.

"Hmm...I appreciate your candor," she said, smiling. "Do you know anything about the position you’re applying for?"

"Well, I assume it’s a typical retail loss prevention job…isn’t it?"

Now Tommy was a bit curious. From the look on her face and her tone of voice, he sensed that something was different about this job or else why would she ask that question? She knew he was experienced so why was this to be any different than the others?

"Not exactly, Tommy. We’re trying something rather unique. We’re having a problem with skilled and very aggressive shoplifters getting out of the store before our security can apprehend them. Most of our security people are female, especially those nearest the entrances where the women’s wear departments are located. Obviously, we use them so as not to be obtrusive to women shoppers in those areas, but they haven’t been very successful in stopping the lifters. Our strategy is to try using men disguised as women in those positions to be more effective. We need people capable of handling this new generation of thieves. Unless we can find females skilled in martial arts, we’re going to try female impersonators. Now, are you still interested?"

Tommy was hesitant but curious. This was not at all what he’d expected and he could see that Louise was dead serious about this. He delayed his answer to reflect on what he had just heard..

"I don’t know, it certainly is different, and it does sound like a reasonable concept under the circumstances. Two questions: do you think I’m the right person, I mean, given the right clothing, could I be passable as a woman, and, what’s the compensation?"

"Two very good questions indeed," Louise replied, studying Tommy’s appearance, "well, you’re not very tall, you’re slender and have rather petite features. You don’t have a deep voice, so you could learn to sound like a woman. Yes, I think you could make a very passable woman."

Tommy was of Eurasian decent, his mother being Korean and his father, American. He does have delicate characteristics for a man, especially an almost beardless face, a completely hairless body, high cheekbones, almond shape brown eyes, and long, silky black hair which he wears in a pony tail or a bun depending upon his mood. He is, in fact, almost too pretty to be a male.

"By the way, Tommy, do you have any martial arts training?" Louise asked.

"Yes, I have a black belt in Karate and I teach Judo as a part-time job."

"Oh excellent! As to the compensation, of course, we will provide you with the necessary woman’s wardrobe with a clothing allowance to maintain it. You will receive six weeks of full time training, including how to act like a lady, sort of a finishing school for girls, so to speak, along with how we handle our in-store security problems at full pay. Oh, and the salary is $20 per hour plus full benefits, with a variable schedule. This whole program is an experiment so we’re going a little above and beyond the market salary due to the unusual "circumstances" we’re asking for.. In return, we’ll expect a one year commitment from our new hires. Are you still interested?"

Tommy was instantly impressed with the salary which was double what his last job paid, without benefits. It sounded great except for the cross-dressing. He was disturbed at having to wear women’s clothes. But the money was very attractive, too attractive.

"Yes, I guess I am. I’m willing to give it a try, " he said with some trepidation.

"Wonderful. We’ll have you fill out the final paperwork including a one year employment contract, and set you up for the training as soon as we fill the class. We expect to hire four males for the positions. Hopefully within a week."

Louise was more than thrilled that he had accepted the offer, knowing that this wasn’t going to be an easy position to fill and he was an excellent candidate.

Tommy completed the paperwork, the usual entry employment forms plus a contract for one year, and went home with mixed feelings about the new job. He needed a job since he was ready to quit the previous one after a minor dispute with his supervisor, and the ubiquitous rent and utility bills were still coming in. But, he was still uncertain about having to work in the guise of a woman. He had not planned on this. He had never dressed as a girl before. What concerned him most was being in public and able to pass as a woman so as not to be embarrassed.

The week passed quickly, and Tommy was called to commence his training.

Monday morning, he met his fellow new-hires and his instructors. The morning was an orientation session describing Macy’s corporate policies and store procedures, along with the details of their new job, since this was new to everyone including management. Macy’s had never tried anything so radical before. Very likely, neither had anyone else in the industry. Tommy noticed that the other men were all also of small to medium build and height, with soft features. In his opinion, all would make attractive women. He was to find proof of that later. For the afternoon session, they continued with details of the job and methods of apprehension of shoplifters. Though the new-hires were all experienced with retail security, Macy’s had their own procedures of surveillance and enforcement which had to be learned.

Tuesday morning, before the store opened, the class did their shopping for their lady’s wardrobe with the assistance of Mindy, their instructor, at company expense. The early start was so that they could select and be fitted before the public filled the store. Beginning with lingerie and ending with shoes, each man assembled his new "work uniform" with a lot of moaning and joking. Mindy assisted them with what they would need, color coordination, proper fit, accessories, and store dress code, which meant no shorts or slacks...skirts and hosiery only. She selected clothing that would help them blend in with the crowds, nothing unusual or extreme. Tommy was a little disturbed with all the lingerie, as were the others, but he reserved comment. He wanted to appear professional and mature about the whole thing, especially being new on the job, but he wondered why they had to wear panties and slips and things that obviously wouldn’t be seen. He wasn’t going to be the first one to ask. Probably the others felt the same way. All obeyed Mindy without protest, but they looked uneasy. She seemed to be the only person enjoying herself, selecting padded bras, breast forms, panties, slips, hosiery, and garter belts with reckless abandon...it was all charged to the company...for her male students.

Tommy was the only man in the group who did not need a wig. It was planned that each "woman" would have several wigs to change often to avoid detection, especially by other store employees, as they were also to keep an eye on sales assistants for internal theft. An exception was made for Tommy because of his naturally long hair. They compromised with his agreement to change the style frequently. He could wear it long, braided, or up in a bun or a French roll. He would change anything but the color.

Starting the next day, Wednesday, they were instructed to start attending classes dressed in their new outfits to begin training as women. So, Tuesday night, Tommy planned to try the new things as a rehearsal for the next day. He hadn’t mentioned anything to his roommate/fiancee, Sue, about the details of his new job, only that he had been hired and the salary. He could no longer keep it a secret when she caught sight of the woman’s clothing. He had unwrapped everything and left them in full view all over the apartment. Tommy looked at the stuff in dismay and wondered if he had done the right thing by taking the job. He explained the reason for all the feminine attire to Sue who was immediately eager to see Tommy dressed as a woman and willingly helped him change. She was always teasing him about being too "pretty" to be a guy. She guided him in selecting an outfit to wear, how to put on hosiery, hooked his bra for him and zipped him into a dress, things he would eventually learn to do for himself.

"I can understand the need for a bra to simulate breasts, but why must I wear panties and a slip?" Tommy asked Sue, mildly protesting. This was the question he didn’t want to ask Mindy.

"You’ve got to feel like a woman if you’re going to look convincing. That means pretty undies. If a girl feels pretty under her clothes, she then feels pretty all over. It’s a matter of self esteem. The slip makes the dress hang better, especially on your legs when you walk. And,it will help you keep your legs together when you sit...you’ll see."

Tommy seemed satisfied with her answers although still not convinced of the necessity. The soft, delicate underwear did feel nice against his skin. Even the pantyhose, though awkward to put on, felt good on his legs, and made them look very shapely.

She showed him how to apply makeup, of which he need very little. A dab of powder, a little eyeshadow, and a touch of lipstick, and he was immediately transformed into appearing as a very pretty girl, although he felt a little foolish. Louise had been correct, Tommy was indeed a very passable woman. With his short, slender body, he looked very natural in a dress wearing a bra filled with silicon breast form inserts, hose, and low heeled shoes. Sue was thrilled with the results, and excited to learn more specifics about Tommy’s new job. He told her after her promise of secrecy. She suggested that he remain dressed as a girl until he feels perfectly comfortable with his new look, the same thing that Mindy had told the class. Since she didn’t ridicule him but rather was very encouraging, Tommy confided to Sue that he already thought the clothes were surprisingly comfortable, and he conceded that maybe it wasn’t so bad after all, and that he was going to enjoy his new job. But he was concerned that Sue would lose respect for him after seeing him in the role of a woman.

"Not at all, Tommy, my love. Remember, I know what’s underneath those clothes and you’re still my man. As long as I don’t lose you to another man," she said, laughing and giving him a big kiss.

Sue arranged Tommy’s long, silky, black hair into a single braid and twisted the braid into a bun. She always enjoyed playing with his hair, but now she had good cause to style it with more variation. He was going to be her "Barbie Doll" and she would have fun dressing and grooming him. After much persuasion, and some instructions on how to walk and sit in a dress, they then went out for coffee as a test, Sue encouraging Tommy and giving him the confidence he needed to go to class the next day en femme.

Wednesday morning, all four new-hires showed up for class dressed as women...very passable women. Louise had made good selections. They all must have spent the previous night working hard on their appearance. None had ever been out in public as a woman. Although they looked feminine, their actions were something else. They were all nervous and uneasy. That was soon to change.

The two weeks in class were spent grooming the men on feminine movements, demeanor, conduct, and cosmetic tips, as well as learning their way around the store where nobody assumed they were anything but the young ladies they presented. Sue continued to mentor Tommy at night in the fine points of being a lady, including hand and eye movements, voice training, etc. It was not entirely necessary for his job, but Sue was enjoying the transformation, especially since Tommy was so pretty, and if he was to be seen in public, she wanted him to be the perfect woman. She even had him walking in 3" heels, something he wouldn’t be doing in the store, but she enjoyed seeing. With the balance skills and agility developed from Karate, he had no problem with the high heels. Tommy had begun to consider the transformation to a new identity a challenge and took to it very well. In the evenings, to practice his new "womanly skills", they went out as two girls and drew a lot of looks and whistles, especially when he wore a short skirt and the high heels and with his hair down, cascading upon his shoulders. After two weeks of total immersion as a woman, both on the job and at home, Tommy became sufficiently confident and comfortable with his new identity to perform his duties. His fellow new-hires all took girl’s names to be used on the job, especially for their radio communications within the store. Tommy became Tammy, given to him by Sue, who continued to call him that.

School was over, and Tommy was assigned to start in an area by the store’s mall entrance. It was in the lingerie and woman’s sleepwear departments. He was to pose as a typical woman shopper and watch for shoplifters while being in radio contact with the other security people. He wore a small, concealed 2-way radio with the mike pinned to his bra strap and a miniature earphone disguised to look like an earring.

Tommy spent the first day ostensibly browsing at girdles, bras, and nightgowns, an otherwise uneventful day. He recalled, in the past, feeling strange even walking through this department, but now, looking and feeling like a woman, it didn’t affect him at all. In fact, he now had a slight interest in some of the articles. He felt so comfortable, he actually considered purchasing some of the bras and gowns for himself. He did learn a lot just reading all the labels and examining the items. Anything to pass the hours.

At lunch, he met with his classmates and compared the day’s activities. They all were enjoying their first day on the job as women. None had been read as males as much as they could tell. They all admitted to temporarily forgetting they were males, especially when using the lady’s restroom. All had adjusted very well.

That evening, Tommy went home and changed clothes, putting on jeans and a T-shirt. He was comfortable remaining in women’s underclothes…it wasn’t worth the bother to change out of them. Even the bra felt natural...he forgot he was wearing it. Sue noticed but said nothing until bedtime when she presented him with a gift for his first day on the job as a woman. She gave him a woman’s long nylon nightgown, trimmed with lace which he appreciatively put on. It was to be the first of many. Since starting his transformation, their sex life had improved radically. Sue enjoyed seeing Tommy as a woman. She became very aggressive in their lovemaking while Tommy assumed the passive position. They both liked their new roles.

Tommy enjoyed the challenge of his new job, and he especially, the money. And his bosses were treating him very well. He was adjusting to his new gender identity easily.

Even on the weekends, Tommy remained as a woman since it was less trouble than to switch genders. He would keep his hair styled and not have to scrub all traces of makeup off, especially his lipstick, which always seemed to leave his lips with hints of red. Sue had shaped his eyebrows into arched, thin, feminine lines and she pierced his ears so he could wear post earrings since the clip earrings hurt after a day’s wear. If he tried to go out dressed as a man, he was recognized as a woman anyway so he decided to just stay that way.

As a Judo instructor, now a "lady" instructor, he started to teach a class in self defense tactics for women. It was more successful than when he was teaching men. His classes soon had a waiting list for attendance.

Things were uneventful on the job until one afternoon when he received a radio call.

"Tammy, a man and woman have pocketed some Fine Jewelry and are heading your way. Stop them and we’ll be there to back you," the radio crackled.

The pair were rapidly headed toward the street entrance. Tommy spotted them approaching at a fast walk and followed them outside where he stopped them, without waiting for help, and asked them in a ladylike manner to please return to the store. The male was large and intimidating and his female companion appeared to be able to defend herself quite well. According to procedure, Tommy had to wait for them to exit as proof that they had no intention to pay for the merchandise, then ask them to return to the store for questioning. They indicated they would not comply by the man attempting to attack Tommy, who appeared to be a defenseless female. In a flash, Tommy had them both in a Judo handlock bringing both suspects to the point of tears and pleading for release, and led them back into the store into the hands of other security people. With the aid of witnesses, the pair were found with the stolen expensive jewelry in possession and were arrested for felony theft. It was quite a scene, a small young woman leading an aggressive pair of thieves back into the store with them crying for mercy.

Tommy received a commendation from the store management for his quick and effective action. The store had recovered some very valuable merchandise and it proved their experiment was working. A female LP person would certainly have been ineffective and probably injured in the attempt to apprehend.

Tommy was asked to teach Judo to all the other security people, including the new "girls". He was paid overtime salary for his effort and used the money to buy prosthetic silicone breast forms which glued on and were much more comfortable than the original pair of inserts. With these breast forms attached and blended in with cosmetics, he could wear outfits which revealed a little cleavage. It was Sue’s idea and Tommy was pleased with the results. They were extremely realistic and even jiggled when he walked, making him feel even more feminine.

Tommy was called to perform special tasks, such as watching suspected employees for theft, where he made several arrests. He was very good at looking like either a young girl in a short skirt and flats or a business woman in a mid-length skirt, blazer, and heels, whatever the assignment called for, but he could handle himself under any circumstance. Even in the men’s department, Tommy could resemble a young wife ostensibly buying for her husband. And the male sales assistants constantly tried to hit on "her." They never suspected he was anything but a pretty young woman. He looked, sounded, and carried himself like a lady.

Tommy had indeed been transformed into a beautiful woman and he enjoyed it. Their circle of friends had eventually been told about Tommy’s job. They were in on the transformation and were very supportive. Because he was so effeminate in appearance, they agreed it was a logical position for him. When he and Sue planned their wedding, they had to decide which one was to be the bride because it would take some work for Tommy to appear masculine again. So, as a compromise, they decided to get married with both dressed as brides. He was so content and committed to living as a woman now, he desired to experience being a bride. Sue agreed it would be a fun idea and they went ahead with the events.

Tammy continued in her position at Macy’s and was eventually promoted into the Loss Prevention management where she supervised a team of female security people. Tammy’s transition to femininity had become so complete that everyone forgot she ever was a male and she was content to remain that way with a very supportive wife.

 

© 1999
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