A Special Underwear Fitting

Billy had been working in the local department store for 5 years after leaving school. He started at the bottom, sweeping floors, but his pleasant, easy manner with the public soon got him noticed by management. Soon he was promoted to junior manager of the footwear department. He soon found that women love shoes, and developed a good rapport with many of his female clients, selling a lot of expensive high end shoes to wealthy women. His 6"1' lean muscular frame and boyish good looks certainly helped and also meant his job was a good way to meet women from a romantic point of view. However, he quickly learned that mixing business and pleasure was a bad idea, as the end of a private relationship with a customer could quickly turn into a loss of sales with both that particular woman and all her friends.

In the end Billy decided to keep his interactions with the ladies down to innocent flirting, enough to keep the woman happy and coming back for more shoes, but not enough to lead them on in any way. Unfortunately this led to a rapid downturn in his social life, as the long hours he worked meant he had difficulty meeting women outside of work.

However, things were about to change. One fateful Monday morning Billy was called in to the general manager's office.

"Billy, I have called you in here to congratulate you on the good work you are doing in footwear," the manager said. "Sales have doubled since you have taken over, and we have received many glowing recommendations from happy customers, in particular the female ones."

"Thank you sir, I aim to please," Billy replied cheerfully.

"However I think we have another challenge for you to take on now," the manager continued. "We would like you to move on to the underwear department and see if you can work your magic there. Sales are down quite a lot recently, and we need to make more of that area of the business."

"I don't really know much about underwear sir," Billy said nervously. "Perhaps a woman would be better in that job, I don't think our female customers would be very happy with a man giving them advice on underwear."

"Nonsense son," the manager replied. "Out lady customers seem happier with you than any of our female staff, and you will be the manager of the department. It is not as if you will be measuring their bra sizes, you will have female staff for that."

"Well if you think it will work sir," Billy replied, still not completely comfortable with the idea.

"Excellent, you can start today," the manager said.

So began Billy's career in the underwear department. It turned out the manager was correct, Billy quickly found his feet and the department sales began to rise rapidly. The main problem Billy noted was the previous range of underwear was very plain and unattractive. While there was always a place for that type of thing, Billy discovered that most women liked at least some sexy underwear for "special occasions" as well as their everyday garments. He began to stock sexier, more revealing ranges of both underwear and swimwear, while at the same time publicising these more exotic garments heavily. Soon the sales of normal everyday underwear had doubled, and the sexier ranges were selling out regularly. He also started promoting men's underwear in the same way, as he found many of the women bought sexy boxers even thongs for their boyfriends and husbands while choosing their own underwear.

Billy soon found his new job even more enjoyable. As a manager, his direct contact with the customers was reduced. However he was still on the shop floor for several hours a day, and on most days his opinion was sought on how a particular undergarment looked, from a man's point of view. While on these occasions he enjoyed looking at some very lovely ladies in skimpy underwear, he always maintained his rule of not dating customers, and made sure a female member of staff was with him in the changing rooms with customers.

One Thursday morning however, things were going to change. Billy arrived to find out that both his female staff members were off ill and he was alone in the department. "OK," he thought. "Thursdays are not normally too busy, I can serve the customers myself, and if any fitting is required I will just have to ask the customer to come back another day."

Most of the day went smoothly, right up until 5.30 when the shop was about to shut. Billy was alone at the till when a young woman walked into the department. She approached the till and smiled shyly.

"I was wondering if you could help me choose some underwear," She said, obviously nervous about speaking to a man about this.

"Certainly," Billy said, "I hope you don't mind but I have no female staff today so I will have to help you myself. Are you OK with that?"

"I suppose so," she said, again very nervously. "My name is Laura."

Billy looked her over quickly to get an idea on what would be best for her figure. It was quite difficult as she wore a heavy coat, wool sweater and trousers. She was quite petite at around 5 foot with medium length dark hair, which was tied up. She wore fashionable rimless glassed and very little make up, however her face had a fresh-faced innocence that Billy found very appealing. He was sure he had seen her before.

"Have I served you before?" he asked.

"No, but I was in with Alison a few times."

Now he remembered. Alison was the local beauty queen, currently at college studying law. She was smart, rich and had every local boy lusting after her. She also spent huge amounts of money in the underwear store on sexy underwear. Several times she had indicated to Billy that she would welcome a sexual advance on his part, but he was honestly not interested. He found her beautiful, but shallow, vain and too high maintenance for his tastes. He also had his rule about never dating customers.

Laura was the proverbial "plain friend" that Alison kept around to make herself look even better. Laura worked at the local library and always wore very sensible plain clothes with little make up, as today. If he were being honest Billy would have had to say he had never really noticed her before, Alison always grabbed all the attention. However looking at her now, there was something in her shy smile that he found attractive, and he was surprised he had not noticed her before.

"Is there anything you were looking for in particular?" Billy asked.

Laura smiled nervously again. She had never done anything like this before and it had taken her weeks to work up the courage. She was used to living in Alison's shadow, buying the same unadventurous bras and pants every few months. However recently she had been getting tired of being the plain friend and after turning 21 had decided to do something for herself for once. Now she was standing in front of this gorgeous guy that even Alison had not been able to hook. He looked as if he really wanted to help her as well. She had fancied Billy from afar for as long as she had been coming to the store with Alison. She loved his tall athletic body and infectious smile, as well as his easy way with woman. He was dressed causally in black trousers and an open necked shirt, which made him look less intimidating than if he had been in a suit. Despite herself, Laura felt herself getting more relaxed in his presence, even though there were no female staff present. She decided to press on anyway before she lost her nerve.

"Well... I was thinking about something a bit more adventurous than I would normally wear. I have seen some of the beautiful underwear Alison has, and I think I might like something a bit like that. I don't know if it will really suit me though. I am not anywhere near as pretty as she is."

"That has nothing to do with it," Billy replied. "Sexy underwear is there to make you feel good about yourself, no matter what you look like. I am sure your boyfriend will appreciate it as well."

Laura laughed. "I am afraid I don't have a boyfriend. Alison gets all the boys; I am too plain next to her. Still I think I would feel better about myself if I had something pretty on underneath my clothes."

"Excellent," Billy said. "Let's look at some styles. I am afraid, as there is no female staff we can't take any measurements today. Do you know your size?"

"Yes, I think so. It has been a year or two since I was measured though," She replied.

They both walked over to the changing rooms. Billy beckoned for Laura to go inside.

"It might be useful if I could see what you are wearing just now, to give me an idea on what we are starting with," Billy said. He knew he was on dangerous ground, as he usually never went anywhere near the women in their underwear without female supervision, but something about this girl was drawing him onwards. He knew it had taken tremendous courage for her to come in today and he felt sure that if he made her come back later she would not return.

"OK then," Laura said nervously. The thought of stripping to her underwear in front of a man gave her goosebumps, but she also felt a shiver of excitement. With trembling fingers she slowly slipped off her jacket and kicked off her shoes. Then she reached down and slowly pulled her sweater over her head. Finally she unbuttoned her trousers, letting them fall to the floor. Now she was standing in front of a man in only her underwear. She felt her face flush and tried to avoid eye contact. "What do you think?" She said in a quiet voice. She quickly turned around to give him a view of her back and sides.

Billy just stood there speechless. He was staggered at how good a body this demure girl had been hiding under her baggy unflattering clothes. Though she was no super model, she was much slimmer than he had anticipated. Her legs were long and well toned with a nice swell to the calves and thighs. Her pants were very unflattering, high waisted and low cut, but even through them her buttocks looked soft and round, just how he liked them. She had a lovely stomach, not perfectly flat, but with a nice swell to it like a real woman rather than the stick insects he was used to seeing in the store. However what really caught his attention was her chest. Even though she was wearing a very unflattering full cup bra with thick straps, it was obvious she was very busty. The bra looked too small for her as well, which made Billy doubt the accuracy of the size. Despite his surprise, Billy's professionalism did not desert him.

"I think we can definitely improve this," He said. "I have to say your bra does nothing for you at all. I don't even think it is the correct size. Most girls want to make themselves look bigger in that department, all you need to do is emphasise what you already have."

Laura blushed. "Thanks you," she said, "but I really don't think I want to show off my chest too much. Alison says that doing that makes men think you are cheap and I don't want that."

'That explains a lot,' Billy thought. Alison was nothing special in the boob department, and was forced to wear push up and padded bras to make the most of what she had. The last thing she would want was her Plain-Jane friend to out shine her in that area.

"Definitely not," Billy said. "You just trust me, I know my job. If you try a few on I am sure we can get something you are happy with. As I said we can't take any measurements today, but I am sure that bra is too small for you. I think even an educated guess will be better than what you have."

"Well, if you think so," She said, her face going even redder. "This has been my bra size for a while now, but I suppose I might have got a bit bigger."

Laura felt a bit uncomfortable talking to a man about her bra, as she been self conscious about her chest for a long time. Still the tremors of excitement were there also and she knew she had gone too far to back out now.

"Yes, I am sure we can improve the fit considerably," Billy said. He walked over to a rack and picked out a black lacy bra and matching panty set. "Here try this, I reckon this size will be much better for you. It will be more comfortable and sexier as well."

"I don't know about black," Laura replied. "They look a bit skimpy as well."

"Nonsense," Billy said, eager to see this lovely young woman in the more flattering underwear. "This is just an ordinary every day underwear set, nothing too risky. Just give it a try."

She took the bra and panties as with a final nervous smile ducked into the changing room. Billy stood outside sweating a bit himself. He had never felt this way over a woman at work before. The combination of Laura's body and demure manner was something he found intensely exciting. He knew he would need to get a hold of himself or there was likely to be trouble.

"I am ready, coming out now," He heard from the changing room. The curtain opened and Laura stepped out. "What do you think?"

Billy was stunned. The lacy black French style knickers contrasted perfectly with her pale white skin and emphasised the length and tone of her legs and buttocks. The bra fitted almost perfectly and supported her large bosom much better, causing her breasts to stand out proudly for all to see. The bra was a quite conservative full cup design, but much better than what she had worn earlier. He looked her in the eye and saw she had noticed his appreciative glances.

Laura felt surprisingly comfortable. The bra did not dig in like her normal one, and she was sure from the look on his face that Billy found her attractive wearing it. She had never felt desired before, and loved the feeling of power. "Do you like it?" She asked.

"Very much, you look great," Billy stammered out. He felt the beginnings of a twitch in his groin and knew he was loosing control. Still he could not stop himself from pressing on. "That is an everyday underwear package, but I know you came here looking for something a bit special. Are you game to try something a bit more daring?"

"Why not," Laura said, enjoying the moment. She was gaining more confidence by the second from his responses towards her.

Billy walked over to the shelves and looked through the stock. He had intended on picking out a mildly revealing teddy, but his cock was getting the better of him and he found himself picking out the most revealing sheer white push up bra and thong set that the store stocked in her size.

"Do you mind trying a thong?" He asked tentatively, as if testing the water.

"OK, I will try anything you want," Laura said simply. All thought of Alison had gone out of her mind. She would do whatever this man asked of her.

Billy handed her the underwear and Laura retreated into the changing room. Once away from his gaze she sat down and let out a long breath. She quickly stripped out of the underwear she was wearing and pulled up the thong. She gasped as she looked at the brief garment, which barely covered her pussy. Luckily she had shaved down there the night before just in case, but her neatly trimmed bush could still be seen through the sheer fabric. The thong felt funny between her buttocks, as she had never worn one before, but at the same time was intensely arousing. She slipped the bra over her shoulders, did the clasp behind her back, and tried to get her breasts into the underwired padded cups. However she soon realised that the brief cups barely covered her nipples and there was no way she would be able to fit in fully. The bra forced her large melons into a shockingly revealing cleavage like she had seen in the wonderbra advents. She gazed at herself in the mirror turning from side to side, examining her swollen mounds of flesh forced up and out of the push up bra. Part of her felt very self conscious and did not want to leave the changing room, but another part was aching to see what Billy's response would be to seeing her in such sexy underwear. She turned face on again and gasped quietly as she noticed that her dark nipples were poking through the cups of the bra, obviously erect. She felt a slight moistness between her legs and for a second had an almost overwhelming desire to reach down and rub her clit, but quickly shook herself out of that daydream. She wanted to see what Billy though of her new look. She reached up and pulled the clasp out of her hair, letting it drop down to her shoulders. Then turned to the curtain of the changing room.

Outside Billy waited impatiently for her to emerge. His mind was conjuring up images of what she would look like in the skimpy underwear, and he was struggling to control his body even thinking about her. He was wearing tight boxer shorts under his trousers and felt his cock swelling slightly against the thin material. He was so turned on by this demure goddess that his rule of never dating customers was close to going out the window. He decided to just go with the flow and see where it took them. Then he heard a rustle of the curtain and looked over to see Laura emerge.

This time he was truly blown away. Her legs looked even longer now she only wore the brief high cut thong which barely covered her pussy, and through which her dark pubic hair was clearly visible. His gaze rose over the delicious curve of her belly, up to the skimpy white push up bra that was doing its best to contain her magnificent breasts. Her creamy white boob meat spilled out of the top and over the sides of the bra, while her nipples were barely covered by the cups at the front. Even then he could see the dark outline of her areolas through the thin material. Finally he looked up and saw a wide grin on her face. Then he realised her gaze was at the front of his trousers. The sight of her in such revealing attire had made him loose control of his cock, which had reared up inside its tight cotton prison and was now making a noticeable bulge in the front of his trousers

Laura had never felt sexier than at that moment. She had expected Billy to be appreciative of her, that was after all part of his job, but the obvious erection she had given him was even better. Then she saw he had noticed her staring at his groin, and they both looked away embarrassed.

"What so you think," Laura whispered quietly.

"I think you look wonderful," Billy replied. All pretence at professionalism was over. He didn't even care about his job anymore, or that she had seen his obvious arousal. All he wanted was to touch this woman.

Laura bent forward slightly causing her huge melons to fall forward against the bra. The tight padded cups pressed them together into a wonderfully tight cleavage that seemed to go on forever. Then she turned around slowly, giving Billy a good view of the sides of her boobs bursting out the bra, and then her full luscious buttocks completely exposed apart from the brief thong, which ran between them. When she turned back round Billy had taken another few steps closer and was now within touching distance. Part of her felt scared, she had never been this close to a man wearing so little, but another part was enjoying it thoroughly.

"Do you like my breasts in this bra?" She asked playfully, as she reached up to her magnificent melons and cupped them, pushing even more of the voluptuous flesh out over the cups. "Alison would think I looked like a cheap tart dressed like this, but I don't feel like one. I feel sexy."

"You look it too," Billy responded. "But I am still not sure if the bra is fitting you properly. I hope you don't mind if I just take a small measurement with you wearing it." He was still not sure exactly how far to take this. Laura did not seem very experienced, and he did not want to upset her. Still he felt an overwhelming desire to touch those luscious tits, and thought the pretence of measuring her would give him the excuse.

He got his measuring tape from his pocket and walked round behind her. She tried to follow him, but he reached out and clasped her head between his hands, turning it forward so she was looking at herself in the mirror, and he could see her reflection over her shoulder.