Working Late

Ben Davis worked in the IT department for a huge multinational firm. They had offices all around the world and every one of them was a spectacle. The particular office that he worked out of was in the downtown Seattle area and was an imposing building, one of the tallest in the area, almost 60 floors high. The company owned all the floors and Ben's department managed the IT for all of it.

Due to the company's employment policies, everyone worked pretty strict hours. 9am to 5pm. Even the management. By 6:00pm every floor was a ghost town. Almost everyone was packed up and out of the door as soon as the clock ticked past 5.

Contrary to the rest of the company, however, Ben's hours (along with most of his team) were very flexible. Due to the nature of IT support, it was necessary that a lot of the work they performed had to be done when it would not impact the day to day operations of the company. Today was no exception.

Ben was sitting at his desk in his office on the western corner of the 55th floor. He had been with the company for over a decade so he had climbed the corporate ladder to a point where, even in his mid 30s, his position afforded him some luxuries. In this case a reasonably sized, and fairly private, corner office with a good view across the Seattle Bay to Bainbridge island. On a clear day he could see all the way to the mountains at Olympic national park. The office also had a little conference table and TV screen for running small meetings and presentations, a comfortable sofa which he had used as a temporary bed on more than one occasion, and a well stocked drinks cabinet for entertaining corporate guests. He didn't get very much opportunity to do the latter in IT, but it was a standard office layout for senior staff and middle management at the firm and he was happy to take advantage of any perk he was offered.

He was admiring the view across the bay as the last few rays of light started to disappear from the sky. The IT department, along with the datacenter, was all based on the same high floor to keep it secure from physical attacks, but also close enough to management on the top few floors should they want to "drop in". God, that drove Ben crazy when management would just idly wander by and make sweeping suggestions on how things should work. Thankfully, Graham Johnson, the head of IT for the firm, was quite adept at fending off these kinds of spurious suggestions so most of Ben's life was pretty straight forward... most of the time.

Today, however, was not one of those times. That evening he had planned to roll out some new software to the company. It shouldn't have been a complicated task, so there was no need for the rest of the team to be on site, but it was not going as well as he had hoped so he was working late to try to get to the bottom of the issues. It was almost 10pm, and the fantastic views across the bay from his office had almost faded into blackness as the sun had set a few hours ago. The light in his office was the only one still illuminated in the whole building, aside from a few security lights ensuring the main walkways were visible for safety reasons.

Ben was the only person in the building above the lobby on the ground floor. There were a few security guards down there, and they always sweep the building at around 6:30pm to make sure everyone has gone home and all the secure doors are locked. Ben had already spoken to Ricardo, the guard with that night's inspection shift, when he made his rounds and let him know he wouldn't be leaving for a good while.

--ooOOoo--

"That's fine Mr Davis" Ricardo said. "We only patrol the doors on the ground floor unless there is an alarm, so you shouldn't see anyone else tonight, but just press 9 on your phone if you have any problems and we can send someone up."

"Thanks Ricardo" said Ben "Hopefully I should be gone before midnight, but I will make sure to let you guys know when I leave".

"Ok sir, try not to work too late" Ricardo shouted as he walked back towards the lifts.

--ooOOoo--

That was a few hours ago though, and the entire building was now silent and essentially abandoned.

Ben shifted uncomfortably in his seat as he glared back at the screen, and the problem before him. "Why isn't this working? The stupid guide made it look so straight forward!" Ben cursed to himself "I need to take a break and try and get a new perspective on this".

He stood up and stretched, hearing a number of cracks coming from his joints. While he did work-out occasionally, he wasn't as fit as he wanted to be. "Ugh, I should probably get back to the gym soon" he sighed. Wandering around his office, to try and get some circulation going in his legs, he glanced out of his window. His view was above almost all of the nearby buildings. All he could see for miles in any direction were rooftops of buildings below him. No one could see him unless he stood right next to the glass, and even then they would need a telescope.

The privacy this afforded him reminded him of his secret hobby. In his private life Ben enjoyed cross dressing. Specifically he liked wearing all types of lingerie, and occasionally enjoyed doing so in public under his clothes. Lately he had started to experiment and push his boundaries with very minor exhibitionism by wearing just the underwear in public-ish places where he might be seen, but secluded enough that the chances of that happening were slim. He realized that with the office in its current state it would be a great place to do this.

Luckily he had some clothing with him that he had purchased during his lunch hour. Ben wandered back to his desk, reaching underneath for his backpack. Inside was a discrete fine material bag from a high quality lingerie store he shopped at occasionally. He particularly liked that store because it was a bit off the beaten track, so he was less likely to see anyone he knew there. Today he had picked out several matching items that comprised a full outfit that was going to update his secret wardrobe.

He laid out the items on his desk to make sure it was all in order. A pair of barely black lace topped stockings, a black and red suspender belt, a matching black and red pair of lacy panties, and a similar matching longline bra to complete the set. He had also picked up a full length black satin and lace slip too.

Ben considered if he should do this. Getting caught in womens underwear might not be a sackable offense, but it would ruin his reputation at the firm. Ben hesitated, but then he looked at it logically. The office was completely empty, and if anyone came on to the 55th floor they would turn on the lights at the lift end first giving him time to quickly dress. He was about as safe here as he could be.

"Fuck it" exclaimed Ben, and started to disrobe.

First he put on the bra. It was a 46B. While Ben was a larger guy, he didn't have anything to fill the cups besides some small man-boobs. He would normally choose A cup, but B was the smallest cup size they had in the design he had chosen. This was an issue with a lot of the really pretty bras available in his band size. There wasn't a lot of spare material though so it was fine as far as he was concerned. He had considered getting a pair of breast forms to fill out the cups, but that seemed a little too close to transitioning. In his mind, Ben rationalized that he wasn't trans, or even gay. He was definitely a man who enjoyed the touch of a woman. He just also really enjoyed the feel of lingerie on his skin, although he thought that the forms could be fun to play with.

Next he put on the suspender belt, adjusting it into place so the clips hung down to about the right length. Fastening the hooks from behind was always a struggle, but he found if he put it on backwards, fastened the hooks in the front and spun it around that he could manage it with a lot more ease.

He followed the belt by reaching for the stockings. He had recently realized that nylon had to have been the catalyst for his lingerie obsession. He loved the feeling of it on his skin, be it stockings, or pantyhose, or other nylon lingerie. He wondered if it had been because his mother used to wear pantyhose all the time, but he hadn't really analyzed himself that closely.

He slowly slid each stocking up his legs, revelling in the feeling as the nylon slipped over his skin. He then clipped them into the suspender belt, and adjusted the tightness of each strap to ensure it was a perfect fit.

Next he pulled on the panties. As far as Ben was concerned panties were always to be worn on TOP of the stockings and suspenders. Too many times he had seen porn where the women would wear the panties underneath the suspender belt and that meant before the sex started they had to remove the belt and stockings in order to be able to remove the panties, leaving them completely naked. This frustrated Ben endlessly and he much preferred when women kept the stockings and suspender belt on during sex.

Lastly he stepped into the slip and pulled it up to his waist. He had initially thought the idea of the slip was edging a little too close to wearing an actual skirt, or dress, but the feeling of the silky smooth satin material slipping over his nylon covered legs was already starting to make him feel a little tingly.

Ben stood up and swished his slip around a bit, then glanced at his reflection in the glass in the window. As the night had rolled in outside the glass now acted like an almost perfect mirror and he could see himself clearly.

There was no chance he would ever pass as a woman, and he wasn't really trying to do that, but he still thought he looked quite good. The bra fit his body well, and the slip gave him a smooth and almost sexy outline.

Ben walked around his office some more then decided to be a little adventurous and risky by wandering out onto the main office floor where the more junior members of his team usually sat. It was still mostly dark but he got a thrill from wandering around "normal" office space dressed only in women's underwear.

Every step he took, the satin would swish back and forth against the nylon arousing him a little more each time. The distraction had helped clear his brain fog a little, but it was time he got back to work.

Working in lingerie wasn't something new to Ben. He often did it while working from home when he needed to give his brain a rest, but doing so in the office was a first. He sat down with a new sense of vigour and cracked on reading through documentation and config files to try to get to the bottom of the issue at hand.

Ben was concentrating hard reading through and memorizing a ton of technical details when his thoughts were suddenly interrupted by a voice...

"Well that's certainly something you don't see every day!" the voice said "Very pretty, Ben."

Startled, Ben's head whipped around to look towards the voice and there, standing in the dark just outside the doorway to his office, was Laura Jones, the regional director for the whole Seattle office.

"I just dropped in to put a stack of purchase approvals on Graham's desk, as I wont be in town for a few weeks, and I noticed your light was the only one still turned on." she said "I thought I would come and say 'hi' but I never thought I would find you dressed like this!"

Ben was speechless and just stared at her, eyes wide like a deer stuck in a car's headlights.

"Oh relax Ben!" she said in a reassuring tone "I have to admit I quite like a man in lingerie. There's something to be said for someone with the confidence to embrace his feminine side, especially out in the open like this."

Ben was still visibly shaking and wasn't sure how to respond. This could end his career, if not completely, then certainly at this firm.

Laura walked over to Ben and put her hand on his shoulder, stroking her finger along one of his bra straps. "Honestly Ben, it's fine, I will keep this just between us girls." she said, half jokingly. "There's no reason for anyone else to know... well except Casey I guess"

Ben looked at Laura with a puzzled expression on his face.

"I'll explain in a bit, why don't you come over and sit on the sofa and we can talk." Laura walked over to the sofa and started to sit down. Ben had calmed down a little at this point, so he got up to follow her. It was only now that he realized how sexy she looked.

Ben had always been attracted to Laura. Even though she was about 20 years older than him, she exuded an air of authority that was very alluring, and the fact she looked amazing just sealed the deal in his eyes. Laura was dressed in a silky red full length maxi dress, and patent black 3 inch heels. He could just make out a hint of black nylon under the hem of the dress which instantly piqued his interest further.

Laura noticed Ben looking at her dress. "It is a bit overkill for office wear isn't it?" she chuckled, "I was heading downtown to get a few late night drinks with friends before going on leave tomorrow, but I just popped in on the way to drop off the paperwork." Laura reached into her handbag and pulled out her cell phone "Let me just send them a message to say I won't be coming. I have a feeling we are going to be here for a while." She tapped a quick message and then put the phone away.

Ben sat down next to Laura, and began to speak "I... I can explain... I was..." Laura raised her finger to his lips. "Save your 'explanations' for later, Ben. I understand the attraction to good quality lingerie. I also enjoy just wearing it for my own enjoyment, but it's always better when you can share your passions isn't it?"

Ben nodded slowly, still unsure of the situation he was in.

"I tell you what, Ben, how about we level the playing field a little to make you feel more comfortable" Laura said, as she stood up.

Ben was confused, but mumbled "oh-kay?"

To Ben's astonishment, Laura bent down and started to lift her dress up. As she slowly raised the hem he noticed that she did have barely black nylons on, as he suspected, and her legs were perfectly formed.

She continued to raise the dress, and to Ben's continued amazement she also had a black satin and lace slip on underneath. As with his own, it fit her form perfectly and gave her an amazingly sexy outline.

Laura pulled the dress up the rest of the way, over her head, and draped it over the back of the chair beside them. Ben's eyes followed it up but he stopped dead, surprised again by what he saw on her chest. Laura's fantastically voluptuous breasts were encased in a red and black lace bra in exactly the same style as his own. Ben's mind raced and his confusion was off the scale. What was happening here?

Laura could see the puzzled, and aroused, expression on Ben's face and smiled. "I guess you are wondering how our underwear is matching so well?" she asked. Ben nodded his head, still unable to form reasonable sentences.

"Well..." Laura started "...as I was saying earlier, the only other person who has any idea about your secret is my friend Casey, but I don't think she realizes how deep that rabbit hole goes. She works as a sales manager at Glamour Belle, the lingerie store where you bought everything today. She mentioned a few weeks ago that a man she recognised from our building was buying things on a fairly regular basis. That, in itself, isn't all that unusual, but she loves to give me all the gossip."

Ben raised an eyebrow.

"Don't worry hun," Laura assured him "she keeps her clients confidentiality with anyone else. We have just been friends since high school so we tell each other everything."

Ben relaxed a little.

Laura continued "Anyway when she described the person to me and, despite the size of the company, I was sure it was you because of some of the details. I knew you weren't currently seeing anyone so I had my suspicions it might have been for yourself, especially given the sizes you had purchased."

"I never thought that the sizes might give me away." Ben said, a little angry at himself for overlooking that "Damn, I should be more careful."

"Don't worry sweetie, the sales team in those shops see it all the time." Laura assured him "Just maybe be careful shopping if people you know are around."

"Yeah, that's why I go to that store, it's a bit out of the way so most people don't know about it and it's usually pretty safe."

"Indeed, although shopping online might be a safer bet if you really don't want to get caught again." Laura pointed out.

"True, but shopping is part of the experience." Ben pointed out "There's something about being able to feel the satin, silk, and lace before you buy it. There's also the added thrill of being a man in the ladies underwear department."

"I can understand that." agreed Laura "Anyway... as it happens, I was in the market for a new set of underwear anyway so I asked Casey to ring up a set identical to yours, but in my sizes, just for the fun of it. You have exquisite taste in lingerie by the way, but I had no idea I would ever see you wearing it. I have to say it suits you really well."

"Erm, thanks?" said Ben, with a hint of embarrassment.

"I decided that I would wear the new set under my dress to go out with the girls this evening. What do you think of it on my body?" Said Laura as she stood up and did a little twirl in front of him. The slip swished against her legs in the same way his had done earlier and he looked her up and down to take it all in.

She was incredibly well toned despite being in her 50s. She was around 5' 5", probably around 145 lbs, but appeared to carry the weight well. All of those numbers seemed reasonable in Ben's head, but it didn't really matter as the end result was perfect in his eyes.

"By the way, Ben, I did say I got the whole set. Would you like to see the rest?" She asked him.

Ben was a little confused, but nodded anyway, and she began to lift up the black satin slip. Ben's eyes fixated on her perfectly toned legs as the hem of the slip slid over the nylon of her stockings. As the slip reached the upper thigh he saw the lace tops come into view, followed by the suspender straps and then the panties.

It was true, she was wearing the exact same set he was wearing, and not only that, the panties were on the outside of the suspenders. This really was a woman after his own heart. Ben didn't think things could get any better.

"You look amazing" said Ben "never thought I would ever get to see you like this either."

"Well..." said Laura as she dropped the slip back into place, and sat down "...there is always a price to pay for everything"

Ben's face dropped. He had a feeling there was going to be something, but he had gotten so carried away with things he hadn't prepared himself.

"Don't worry sweetie, it's nothing bad." Laura assured him "I would just like a story. Tell me, how did you get into wearing lingerie?"

Ben sighed a little with relief, and got up. "Ok, but before we start I need a drink" He walked over to the drinks cabinet and poured himself a large glass of whisky. "Would you like one?"

"Certainly. That would be great" Laura replied.

Ben poured another glass and passed it to Laura as he sat back down on the sofa. He then took a big swig from his own glass.

"Ok" Ben said with a big sigh "Where would you like me to start?"

"Well how about when was your first experience with women's underwear?"

"Right, okay, I've never really thought about it much, so give me a moment." replied Ben, gazing into space for a moment as a memory suddenly jumped out at him "Huh, yeah, ok... I guess the first time that I can recall was when I was pretty young, probably just before puberty..."

--ooOOoo--

"The first time I ever consciously noticed lingerie was with my mothers pantyhose." Ben recalled "She used to wear them all the time as part of her work outfit. She was an office worker so the standard dress code for women at the time was a blouse, knee length skirt, pantyhose, and low heels of some kind. I think that because she wore them so often they became lodged as a symbol of femininity in my mind, but being "underwear" I guess they held a certain taboo for a young boy. Anyway, this particular incident took place one winter, and I had come home from school earlier than usual. I don't recall why but we had an unexpected half day. I think it might have been a water leak, or something, that closed a lot of the building down. Anyway I let myself into the house with the spare key, and then called mom at work to let her know what had happened and that I was home safe. She told me she wouldn't be home for a few hours, so I wasn't going to get into any mischief."