Working Relationship

Sarah had been working as P.A for David, a junior partner at the legal firm, for over a year. She was happy in her work and they got on well together. From her first day Sarah had felt a 'connection' to him and this empathy seemed to show in the work that they were involved in. She could tell that he liked her, he was kind and considerate, and she seemed to almost be able to anticipate his needs before he voiced them.

Four months ago, their aging family car had required major repairs. Sarah had mentioned this, saying how they were concerned because it looked as if the car would be off the road for some time. David had suggested they would be better off spending what it would cost to fix on something newer. She said they knew that, because of its age and condition, it really wasn't worth spending that much on, but the cost of replacing it was more than they could manage just now. David told her his company car was about to be replaced, and in line with company policy, it had been offered to him. He could buy it from the company at a very good price. He suggested that he buy it and sell it on to her. She said it would be still be a bit more than she and her husband, John, could afford at the moment. David then said he didn't want to make anything from the deal, she could have it for the same price he paid. He would buy it and she could pay him back, interest free, with an agreed amount each month from her salary.

She talked it over with John that night. Knowing that the car was low mileage with a full service history and that David was a careful driver who looked after his car, they decided to take him up on his offer. The next day she told David that if the offer was still available, they would like to take advantage of it. The price was far below anything they could have bought a car like that from anywhere else. David arranged for his bank to collect the regular payments from Sarah's bank account each month, a few days after her salary was paid in.

One evening, as Sarah was checking everything was safely locked away before leaving, she noticed an expensive looking camera on the floor just under the desk in David's office. She picked it up, intending to put it in her desk and return it to him in the morning. Her natural curiosity took over and she switched it on to see what he had taken photos of. Scrolling through the pictures, she saw that they were mainly of one lady, and she was mostly in a state of undress. She wondered who she was, that he had been taking photos of. 'I didn't know you were such a naughty boy' she thought, "But it was careless of you to leave this lying about, if I hadn't just checked your office before I left, anyone could have found it and photos like this could have been embarrassing." Instead of locking it away in her desk, she slipped it into her bag, deciding to take the camera home for safekeeping, and then return it to David tomorrow.

It was her husband's evening out at the club he went to, so after dinner, he went out. Instead of settling down in front of the TV as she usually did, she decided to connect the camera to their computer where she would have a better view of the pictures than on the small screen on the camera. It was a simple matter of a USB connection and within a few minutes she had copied the pictures into a folder on the computer's hard drive. They didn't seem to be in any order and the first few she looked at she didn't really notice anything odd about them. They seemed to all be of the same young lady, in various states of dress, some more undressed than dressed, in some she was wearing only her underwear. "She must be his girlfriend," Sarah thought, and suppressed a little giggle at the thought of what she would say if John had left their camera, with her pictures on it, on the floor of his office where anyone could have found it.

She wasn't too shocked, because John had suggested she pose for him, when she had bought him a digital camera for his birthday the year before last. She had let him take a few one evening, when they had both had a little too much wine. Nothing too naughty, a couple of 'up skirt' shots showing her panties, a few with her blouse unbuttoned and one with her skirt around her hips showing her panties and her bra cups pulled down, showing her breasts. She made a mental note to check that John had deleted them.

Then she came across a picture that stopped her in her tracks. This was definitely no lady. She was wearing high heels and a bra, but that was all, she had no panties on. Not anything particularly shocking in that, Sarah had seen much worse, but what stopped her in her tracks was instead of a woman's vagina, this person had a penis. After the initial shock, Sarah was surprised to find herself fascinated by the picture. At first she thought it must have been edited on some photo editing program, but then she realised it couldn't have been. The photo was still in the camera. To have edited it, David would have had to download it to a computer, edit it, then upload it again. Why would he put it back onto the camera?

'Whoever it was,' she thought ' he has a very nice body, and I wish my legs were as good as his, she giggled, or is that as good as hers?'. She was rather glad that John was out, because looking at the picture was causing a response deep inside her, a response she was finding hard to ignore. Her pussy was beginning to moisten as she looked at his slim body and his very beautiful penis. "What a shame," she muttered "He must be gay, dressing up in womens clothes. If he was here now I wouldn't mind seeing if I could convert him back to being being straight."

Then the thought struck her, 'David must have taken these pictures himself, otherwise why would they be on his camera? On this picture it had been taken using a mirror, because she could see the camera he was holding. Checking back through the ones she had already seen, she realised that most of them had been taken in the same way. A few hadn't, and checking on the camera, she saw there was a 'time delay' feature, which had obviously allowed the subject to set the shutter and position himself to be in the shot.

If he took the picture himself ......? No it can't be.' She looked again at the picture, trying to ignore that he was naked apart from high heels and a bra, and tried to visualise what her boss might look like if he was naked. He always wore a suit to the office, but he was slim, like the man in the picture, but could it be him? 'It couldn't be ...... Could it?" Sarah wasn't sure. She found another picture of him, and on this one he was wearing a black bra, stockings, a suspender belt and panties, but it showed nothing new. In the red bra he looked as if he had breasts, very small but they looked to to be there, but in this one there was nothing to fill out the bra at all.

Suddenly it 'clicked' and she knew. She was certain it was David. She even knew where the picture had been taken. There in the background was a telescope and she knew David was an amateur astronomer. She remembered him telling her liked to look at the stars and had bought an astronomical telesope, which on clear nights he set up in his back garden, but he kept it in his room at home when he wasn't using it, for security. These photo's had been taken in his room and, because they were obviously self taken through a mirror, it seemed almost certain they were pictures he had taken of himself.

She had never thought of David being gay, in fact she was fairly sure he wasn't. He had mentioned a girlfriend a couple of times, although she knew he didn't have anyone he was serious about at the moment. Of course, a 'girlfriend' could just have been a cover. She knew there were lots of gay men who were married with a family. Maybe his 'girlfriend', who she had never met, was really another man. Her eyes kept returning to the first picture and with a start she realised that she was rubbing herself between her legs. She couldn't seem to stop thinking about his cock, and imagining holding it in her hand, kissing it, even ....... "STOP IT!" She told herself out loud. "You have never thought of him like that, he is just your boss. Yes, you like him, he is a very attractive young man, but he is still just your boss," she thought.

She clicked off the picture and back to the thumbnails, searching for something that would give the lie to this being David. Maybe it was a friend and they were messing about, while getting ready to go to a fancy dress party or something. There had to be a sensible explanation, but if it was a 'one of' for a party, why would he have all those different outfits, right down to the lingerie? The mouse pointer landed on another thumbnail and without even thinking she clicked it.The picture that opened was one she could have shown to her mother. Fully dressed, a modest looking young lady. Perhaps this was his girlfriend. He wasn't gay at all, this prove ........ O.M.G! She zoomed in on the face ....... Ignore the very fetching dress and feminine stance, take off the wig and the make-up and it was him, it was David. But unless she had seen this she never would have known. He could have walked past her in the street dressed like that and she wouldn't have known him.

She decided that she would go in a little bit earlier tomorrow and put the camera back where she had found it and he would never know that she knew his secret. She wouldn't say anything. She liked her job and she really liked David, he had always been good to her ....... Then she saw something which made her heart leap into her mouth. There in the thumb nails was something that looked completely out of place. It had been taken in different location, and was much darker than the rest.

She clicked on it and the picture opened on her screen as large as life. Her hand flew to her mouth, it was a picture of her, taken while she was reading something, in the office. "When did he take that?" She wondered. He must have been standing just behind her to have taken this over her shoulder, looking down her blouse. She was leaning slightly forward in the picture and her bra had fallen away from her breasts. The photo was rather dark, obviously he must have turned off the flash, but showed both of her breasts, and one of her nipples was completely exposed.

"Why would he take a photo of me like that?" She said aloud. "Surely he knew that if she had seen him taking it she would have demanded to know what he was doing. Taking that picture could have got him fired. Men had been sacked for far less. If, instead of handing the camera back to him, she took it to the 'Personel Dept' and showed them just that one picture, he would be gone before the end of the day, but, surely if he was gay, why would he want to look at her breasts? "Mind you," she thought with a giggle, "They don't look too bad, do they?"

The thought that he had wanted to look down her blouse at all, said something to Sarah. Did he find her that attractive? Did he wish he could make a pass at her, but knowing she was married, assume that doing so would just get him into trouble? Sexual harrassment was taken very seriously these days and men had been fired, just for saying things which could be construed as having a double meaning. Sarah clicked back to see the first picture again. Even with him wearing lingerie, the thought of his cock, semi erect as it was, sent a small shiver down her spine and moistened her pussy. Her hand slipped between her legs again.

That was when she saw the picture that took away all doubt. She only saw it by accident. The pointer wasn't properly on the picture she had intended to open and it opened the next one to it, which she hadn't noticed before. There was David, standing in that same room, with the telescope in the corner, but this time he was wearing a very pretty minidress and in this picture his face was in the shot. He was not wearing a wig or make-up, it was definitely him

A very naughty idea occurred to her. If he can take self pictures, so could I. As long as I hide my face only he would see them and even though he will know who it is, he won't be able say anything. He took a photo down my blouse and if, when he looks at his pictures, he finds another one of me, perhaps an up skirt one, which he knows he hasn't taken, he will know that I know his secret and about the picture of me.

There was a conference coming up where she was going to accompany David, and it was going to involve at least one, probably two nights staying over. "If he knows I know about him dressing up, maybe he will take some of his things with him and we can have a 'girls night out' together. If he looks like he does in that dress and wig, he would probably be better at pulling a man than me, because, after 10 years of marriage I am well out of practice." Suddenly the idea of going out with a handsome young man like David, who was not only completely dressed as a woman, but looked so convincing that he could pass almost anywhere as one, was very appealing. She was really becoming aroused, and the more she thought of David, in full make-up, dressed in ladies lingerie, with a pretty dress as he escorted her to a club, the hotter she got. "If that happened, never mind him pulling a man, he could pull me" she thought. "Kissing him would be like kissing another girl, but it wouldn't be a lesbian kiss, because he is really a man."

"Oooh Sarah" she said out loud, "You really are being very naughty tonight." She looked at the clock, John wouldn't be home for at least an hour. She thought for a moment about him. He was quite slim as well, like David in some ways, quiet, thoughtful and gentle. She wondered what he would look like if she dressed him in some of her clothes. She pushed the thought away, and returned to the picture of David, that she had at first thought was of his girlfriend. Completely unbidden, the thought of John wearing ladies undies came back.

"John has never said anything that might have suggested he likes wearing ladies clothes, you are being silly," she thought, "But he does seem to defer to me on most things, especially if I speak sternly to him. He is very quiet and easygoing. Sometimes," she thought, "He behaves as if he wants me to order him about. Perhaps I should take charge and dominate him more. He could be my submissive. I think I would like a pretty girl friend, and with careful make up, I think he could look almost as good as David does here. Then I could have the best of both worlds, a husband for outsiders to see, and a girlfriend, for when I am feeling more ...... in need of feminine company." As these thoughts were going through her mind, her hand had been very busy between her thighs. She had pulled her panties aside and had been rubbing her clitoris harder and harder. The thought of John, made up and dressed in her lingerie, together with the photo on the screen of David looking so beautiful, dressed as a woman was too much. Her fingers plunged into her pussy and found her G-Spot. The orgasm that had been building up inside burst on her and with a groan she collapsed over the computer keyboard, as wave after wave of pleasure shook her whole body.

As it subsided, Sarah realised that John would be home soon. She didn't want him to see either the camera or the downloaded pictures from it. Taking the folder which held the photos, she hid it inside another folder, containing the gardening sites she went to. She was sure John would not look in there, he didn't like gardening. Shutting down the computer, she put the camera back into her bag. She clicked the 'Air freshener' to send a blast of perfumed air into the room. She didn't want him noticing the odour of her arousal when he came in. She was glad she hadn't told him about finding the camera, because he would have wanted to see what pictures were on it too, and she didn't want him to seee David like that, let alone the picture of her breasts. Once she was sure that traces of her 'indescretion' were completely erased, she went upstairs to use the bathroom and to freshen up. It was just as well she had closed down the computer before she went upstairs because just as she finished in the bathroom, John came in through the front door. Sarah pressed the toilet flush, before running water into the basin to wash her hands, and coming downstairs.

The thought of John dressing in her undies wouldn't go away. The more she tried to put it out of her mind, the more it pushed into her thoughts. "This is silly" she thought, "Why should it be having such an effect on me? Even if he would do such a thing, he would think I had gone mad if I suggested it." Logic, however, didn't come into it as far as her pussy was concerned. It had been moist before, while she was looking at David's pictures. Then she had masturbated and orgasmed, but even though she had freshened up since, now she was positively wet. The more she thought about John in make-up, wearing ladies clothes, the wetter she got. She now found herself thinking about ways she could bring up the subject, without him dragging her off to the doctors to get her certified.

Little things which had never seemed important at the time, began to push to the front of her mind. He had always shown an interest when she was shoppping for clothes, particularly underwear, and he had a good eye for what would suit her. He usually bought her clothes for Christmas and Birthdays, some very pretty and quite sexy, but had never bought her the 'fluffy, completely useless' kind of undies that men usually went for. Everything he bought her was tasteful and expensive and even the very pretty undies were a pleasure to wear. Maybe he might like to wear something like that himself, privately, at home of course. From the look of those pictures, David has some very nice things too," she thought, "Maybe he could choose something for John as well. From the look of it, they have similar, very good taste. I wonder where he shops for his clothes? Those two dresses certainly weren't cheap, and on him they really look classy, but surely he can't just walk into a dress shop and try things on ......... "O.M.G! Stop it -- You silly woman!" She said to herself, "This is becoming ridiculous."

Sarah and John sat watching TV for a little while, but for some reason Sarah felt that something didn't feel right between them tonight. At first she thought it was her, because of all that had happened during the time John was out. Looking at those pictures on David's camera and fantasising, especially finding the one he had taken of her.

At first she had been shocked and angry that he would take such a photo of her. The more she thought about it, the more she wondered why he would risk his whole future to do that. He must have seen her bra was a little loose when he looked down her blouse and saw her breasts. OK, she should have been more careful, knowing her bra might fall away to expose her breasts, but for him to have risked everything to take that photo, must have meant he liked the view enough to want to be able to look at it again. The thought of him looking at that picture, and maybe fantasising about her, she found very exciting. She found herself wondering if he masturbated, looking at her breasts.

She forced herself to stop thinking about the photos, and bring her mind back to what was wrong with John. He was definitely 'on edge' tonight. There was an 'atmosphere' in the house and it was like a wall between them. "This isn't like us" she thought, "Something is bothering him."

"Is something the matter dear?" She asked, "Only you seem a bit 'out of sorts' tonight."

At first John didn't want to say anything, saying he was all right, but Sarah could tell something was wrong. After 10 years together, she could tell when he was hiding something from her. At first she let it pass, letting him 'stew' a little. He had never been good at keeping things from her and she knew that now she had brought it up, he wouldn't be able to rest until he had told her what was bothering him. "I'll give him a few minutes, then I will ask him again," Sarah thought, "Then if he doesn't tell me I will have to use the 'stern, bossy' tactic, that always works."