Trapped in a Box

by Peg Thebois

 

Amy recognized this customer by the time he was halfway through his story. As a face he was pretty forgettable, short and slender, with a slightly scruffy head of light brown hair. His face was completely free of stubble and his fine eyebrows perched just above his glasses, they were fine enough to have been an overzealous tweezing job but were too uneven and disorderly, just one of those people with fine eyebrows. He was wearing a button up black and white track shirt tastelessly mated with a pair of navy slacks that looked like they believed laundry was a mythological place. He wore a brown leather jacket that was a few years out of date. But it wasn't so much this customer, who looked to be in his early twenties, that Amy recognized it was the story he was telling.

The story revolved around a trip to a private retreat in neighboring British Columbia with his girlfriend, and a rather extravagant Christmas present. His bisexual girlfriend had fantasized about "being with" a guy in a dress, so he was here to get what he needed to fulfill that fantasy. Amy was familiar with this story, her best friend Gloria had just told it to her on her lunch break forty minutes before. Gloria worked at another clothing store in the other end of the mall, and Amy finished work, just half an hour before Amy started.

Amy smiled as she set about getting him on track, first sizing him up; recalling Gloria complain that this guy, this male, was the same size as she was, Amy recommended a size 10. After the customer assured Amy there was no price range, spouting a line about getting paid back a two year debt from a friend, Amy started showing him around the store, gathering items for him to try on. She selected a few items of widely different styles, short and revealing, long and revealing, demure, and glamorous. And then once she had a handful of frilly, lacy garments she escorted the customer to the dressing room and set him up inside. As she walked away Amy finally allowed herself to smile the way she wanted, for unbeknownst to the customer Amy knew the ending to this story. The bank card with which he would try to pay would be declined, presumably because this large deposit took five banking days to verify.

Amy tried to appear calm as she moved quickly to the counter and picked up the phone. When the person on the other end picked up she said, "Hi Gloria, are you still in the mall? You'll never guess who just walked in."

******

Sandy heard the door shut behind him and finally let the half faked look of embarrassment slip from his face. He eyed the first of many garments that the helpful sales girl had helped him select, all very pretty but none particularly that inspired that need to own it as he had been struck with on more than one occasion. Fortunately those items were few, far between, and usually affordable as it was often the price that attracted him.

Sandy unbuttoned his shirt, and dropped it, admiring his lean, smoothly shaven chest in the mirror. This was one of his favorite ways to spend a day, going place to place, trying on various outfits, the embarrassment of the social stigma associated with what he was doing was part of the thrill, but he would gladly do without it for the freedom that women enjoyed. The freedom to go shopping for skirts and dresses and not purchase anything without suspicion, the right to be honest in what he wanted, and not have to make up these outrageous scenarios. Ah well, society needed somewhere to point their righteous finger, and with the passing of homosexuality into mainstream that left fringe elements, many of which were harmless but unusual.

Finally he took off his pants and picked up the first dress, a red polyester sheath dress with a second layer of black lace over it that would reach his mid thigh and a neckline that would show cleavage if he had it.

******

Shirley Rogers hated her job. She had been working here three months and in that time she hadn't had one serious security issue to deal with. All the shoplifters here were thin with the current trend, and most of the came up to her shoulders or shorter. The cameras monitoring the change rooms were almost infallible in catching them as well so for the most part her job was pretty boring. Today was different though, those same cameras replaced diligence on the part of the security staff for the store would provide her with a very entertaining sight.

At first she wasn't sure if what she saw was accurate, a man was going into the change rooms and was taking with him a stack of dresses. Shirley smiled when she saw this, it would certainly be good for a chuckle. As the salesgirl closed the door the man turned to the mirror and smiled widely. As he stripped off his clothes his underwear came to her view, they were obviously women's panties, bikini style with a transparent mesh back.

Shirley laughed at this guy a little, however for an unknown reason she didn't find it as funny as she thought she would. She found herself watching with fascination as the man grabbed the first dress off it's hanger and slipped it over his head. It clung to his body, highlighting just how small he was, the skirt was short on him and the sleeves made of pure lace were just so markedly feminine. Everything combined to make the man look vulnerable somehow. He just looked so weak and ready for someone to take him and break him. Shirley realized that she was getting turned on watching this man belittle himself with these soft womanly things. She slumped forward in her chair, dropping her hand between her legs to rub through her pants teasing herself a little as she watched with rapt fascination as the man turned himself and examined himself in the mirror unaware of his audience, and just what he was doing to her.

******

Amy quickly filled Gloria in on the situation and her plan, she watched Gloria's face take on a malicious joy. This male had wasted half an hour of her time and now she was going to get hers.

******

Sandy was modeling the fourth dress that she had recommended, having found all the others fitting well, as he knew they would. This dress was pure black cotton with see-through puffy sleeves and a frill around the hem, very cute. While he examined himself in the dress he heard the salesgirl returning to the back with another customer. He paid them little mind as he continued his self critique, this dress was not as revealing as the other, and it was cuter, but not as sexy, the combination of red with black lace always did something to him.

Best of all there was still one more dress to try on, it had spaghetti straps that criss-crossed in the low cut back, and a cowl neck. That dress was red and just a little bit of a black shimmer in the fabric. The skirt of the dress was ankle length and A-line. He had a suspicion that it was going to be his favorite.

Sandy just stood there a minute, mentally comparing the two dresses, the sooner he put on that last dress the sooner his fun at this store would end, and that was not something Sandy was looking forward to. However as he stood, examining the next dress Sandy caught a hint of movement reflected in the mirror. He turned around just in time to see his pants disappear under the divider separating his change room from the neighboring one where the salesgirl had placed the other girl.

Sandy bent down to try and grab the leg of his pants but already they were gone and the girl was on her way out the door of her changeroom. Reflexively Sandy moved as though to chase her but then realized where he was and more importantly how he was dressed.

"Hey!" He called out after the girl. "Those are my pants, stop!" He waited a moment, no response, not from the customer, not from the employee's of the store, nothing. He called again, his heart racing now. What was he going to do, if he had money he could buy a pair of pants, even if they were girls pants they had to be better than what he had on right now. However he made a point to do these "shopping trips" when he had no money so that he could be sure that his bank card would not work, leaving him stuck buying something he may not actually want. He was going to have to reveal the whole game to the store and then who knows how he would get back home with his dignity intact.

Finally the sales girl responded to his cries. "What's wrong?" she asked through the door.

Sandy told her about the girl in the next stall reaching under the divider and stealing his pants.

The girl gave a drawn out thoughtful hum as Sandy sweated bullets inside the changeroom. Then the girl said the words that Sandy was most hoping not to hear her say. "That girl just left the store. I think I saw one of our store security people chasing her though." Sandy was starting to panic, what was he going to do? If security didn't get his pants back he was dead.

"Why don't you pick out what you want to buy for your weekend with your girlfriend, and we can wait in the managers office to see what our security turns up." From someone who didn't know the full situation it was a reasonable suggestion, however Sandy knew better, he knew that when he went to pay for whatever dress he wanted then the jig would be up, and he had also dug himself into a hole earlier by insisting on a dress, even if he could afford a dress, getting it as well as a pair of pants would be impossible.

Still, if security recovered his pants then all would be good, he would be able to conclude this game as all the others he had played in all the other stores he had been to. It was a double or nothing bet, the longer he waited for a way out of this situation the deeper in he would be. Waiting seemed for now to be the best of his options though, and although he would rather not go where anyone could see him Sandy was getting uncomfortable standing in the rather cramped little changing cubical.

If he was going to have to bargain his way out of this situation the less he had to pay the better. Looking over the selection of dresses he had taken in he found one that was cheaper than the others, it was off the clearance rack. He had liked it but dismissed it as too slutty. It was a red mini-dress with glittery sparkles, the back was low cut and so was the chest. It had a halter style neckline, leaving him very much exposed on all fronts. His legs, and back barely covered in any way, his arms were completely revealed, and the plunging neckline even showed his smooth, hairless chest. On the good side the dress was only $20. That unfortunately was the deciding factor, not that the price of the dress solved his problem of clothing but it would satisfy the sales girl's request that he chose an item, it would keep the charade just a little longer. And besides this dress would at least get him from his change room to the back, where the manager's office would no doubt be.

"So have you picked something?" The girl asked.

"Yes, I think I've got it."

"So let's go wait in the manager's office."

He opened the door and she stared at him in mild surprise, "Oh. I, uh, I thought you would just wear your underwear, it's only a quick walk through the back."

Sandy went red with shame at the suggestion, he couldn't go anywhere, not with the underwear he was wearing, it probably wasn't legal even if he had the courage, not with the backside being entirely see-through. "I can't do that," he muttered letting his head sag in embarrassment. "I've already gone shopping for the panties to go under my dress, and that is what I'm wearing." He congratulated himself on a quick lie but immediately countered by chastising himself for being so foolhardy as to wear his panties in the first place.

And so Sandy stepped out of the protection of the changing room into a larger room, filled with chairs and many more changing rooms, it was also occupied by several women, and even a couple men, however unlike Sandy these men were sitting in the chairs, waiting for their girlfriends. As Sandy walked past them all towards a door marked private his only solace was that the main body of the store, and the mall itself would only get a passing glimpse of him as he walked past the opening into the store proper. However this relief was tempered by the gauntlet of comments he had to run as he walked to that door. The girls were gasping and giggling at him, and worse than that.

"Nice legs, sweetheart." One said.

"Disgusting,"

"Sissy,"

"Faggot."

"Ewwwww."

Finally Sandy considered himself safe, as he walked past the last person, from here it was just a clear five foot walk to the door. Then he felt that last person he had walked by, a rather brutish looking man, grab his skirt. Suddenly it was around his waist, not only that but his panties were on full display, his ass was on a pedestal for these people! And they roared, the laughter in that back area was deafening, Sandy ran the distance to that door, trying to outrun the view of the other customers. As the salesgirl fumbled with her keys Sandy tugged the skirt back down around his thighs feeling a gross pain in his stomach from the humiliation of his situation, and his inability to flee the mocking crowd. They were all staring at him, pointing, laughing, this wasn't what he had wanted when he started this game. The door finally opened and Sandy wasted no time pushing past the girl to seek refuge away from prying eyes.

There was a big girl dressed in a blue shirt with "security" written in white on it waiting for him. She led Sandy through the large room, cluttered with boxes, to another door, but this one was not locked. The room was very sparse, nothing but a desk and a couple chairs. There was a moderately expensive phone sat on one side of the desk, beside a stack of inventory sheets and invoices. The woman behind the desk did not look at all pleased at this interruption, but her expression became bewilderment when she saw Sandy. They were both indicated to sit down, and they did, Sandy pressed his naked thighs tightly together as the skirt of his dress rode up just a little higher as he sat. The salesgirl told her manager, Mrs. Broadworth by the placard on her desk, about Sandy's need for a dress and about the other customer inexplicably stealing his pants.

"Thank you Amy." Mrs. Broadworth said. "You may go back to your work."

Amy left the room, leaving only the security woman, Sandy and Mrs. Broadworth. "So, what is your name?"

"Sandy,"

"Well Sandy, we are going to have to wait for mall security to see if they can recover your pants. In the meantime why don't you tell me all about what happened, what brings you here today?"

Sandy swallowed, hoping that he could find some way to carry this lie off. He then proceed to spill the same line he had used on Amy the salesgirl, his girlfriend wanted to be with a guy in a dress so he was going to fulfill that fantasy for her.

Mrs. Broadworth looked at him questioningly. He had to wonder did she know, could she tell he was really just a pathetic transvestite out for thrills? What would she do if she could, obviously the store wouldn't take kindly to a man wasting their time looking at dresses that he couldn't afford.

"Well Sandy, I will make you an offer, we do not want an incident made of this and I see the dress you selected was from our clearance rack. We will give you that dress you are wearing, free of charge if you will not tell anyone about the problem you had here today."

Sandy felt a sinking feeling in the pit of his stomach, on the good side getting a free dress was never a bad thing, on the other hand, he had a bad feeling, and the last thing he wanted was to have to walk back through the mall, the worlds largest mall for crying out loud, wearing this tiny little scrap of a dress. Still if his pants weren't recovered he would have to make that trip in his see through assed panties, and he had no doubt that he would be escorted by security before long, if that were the case. Sandy nodded to Mrs. Broadworth, "Thank you."

Mrs. Broadworth looked up to the security woman, "Why don't you go see Nancy has come back with Sandy's pants?" The woman left the room.

******

Sandy hung his head as he heard the people around him gasp, or laugh. Unfortunately security had not returned with his pants and so here he was walking through the mall, crowds all around him in the dress he had been given. He was able to avoid much of the crowd by staying on the upper level of the mall, however this was no ordinary mall, there were always people around, everywhere. And most of them were staring at him. Off to one side Sandy saw a flash of light, and he cringed, another tourist, another camera. Another humiliating picture of him floating around out there, being shown at the family dinner table, being seen by who knows how many people. "Oh look, here's that freak we saw at the West Edmonton Mall." And he still had the bus ride home to deal with, fortunately his roommate was at work this time of day, he wasn't sure how he would explain things if the situation were otherwise.

******

Shirley felt her breath quicken nervously as she pressed the button, and watched the security tape slide out of the machine. She quickly tucked it into the inside of her jacket, she would catch flak from the boss for forgetting to set the machine but it would be worth it. Her pulse was already racing, and she was getting wet just thinking about when she got home, and could sit and enjoy this video properly.

******

Mrs. Broadworth smiled at the girl standing in her office. She was glad that Amy had come to her with her idea. She didn't think she could have kept a straight face otherwise, when that stupid looking man in a dress had walked into her office. And he had even played into their hands by choosing an outfit from the clearance rack, as opposed to making her send Amy to find him a dress from that area.

Amy's plan to take the sissy down a peg or two had worked out beautifully, he would be sure to think twice before trying to pull a fast one on another store. They had certainly seen today who the weaker sex really was.

THE END

  

 

 

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© 2003 by Peg Thebois. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.