Robert looked at the beautiful young girl in the mirror. She was wearing a sleek red silk dress with Asian emblems on it, held on her slender form by spaghetti straps. Her modest breasts barely registered to the casual eye but the vivid red lipstick enhanced her mouth and the smoky eye makeup she had expertly applied gave her face a striking beauty and her long black hair that descended over her shoulders framed her beautifully, The dress ended mid thigh and then her slim legs showed down to the bright red 4 inch heeled shoes she balanced casually on. She knew that most Asian girls wouldn’t wear such a heel but she wasn’t Asian, despite the dress, and she knew that when she walked in the heels she felt elegant and attractive and interesting – a creature that would turn heads and attract every available male that saw her.

Robert’s gaze turned to the alarm clock at his bedside. He had work in the morning and would need to rise early to avoid being late. His superior was a real ball-breaker and she seemed to be targeting him – picking on him for any minor misdemeanour and humiliating him in front of his fellow workers, As the only male in the Administration Department he wondered if his only fault was being a man and at that thought he had to give a wry smile because in many ways he felt there may be some common ground there.

Robert sighed to the girl in the mirror. “Thank you for another lovely evening, but I need to call a halt to things. Maybe I could see you again tomorrow – I’ll be free all weekend and we could spend the whole two days any way you wanted?” He blew her a kiss which she returned in a perfect synchronised response and gave a little smile. “I’d really enjoy that” she said in her soft voice.

Robert sighed once more and stepped away so he could no longer see her reflection. Sitting on his bed he took off his high heels and then pulled down the zip of the dress that was between his shoulders, taking care to remove the outfit without it touching his face. He hung it up on a hanger to keep it crease free and then walked into the bathroom to wash off the make up, remove the nail varnish on his hands and then ease off the breast forms he had applied earlier that evening. Glancing at his reflection he realised he had missed one more item and he removed the wig he had been wearing and took it through and placed it on the head form that would reduce the risk of tangles.

The girl in the mirror was no more. Now as Robert looked in the bathroom mirror he saw the 30 year old virgin he despised and was embarrassed by. Robert Mitchell. Only child of Arthur and Millicent Mitchell, both deceased. His father was, by all reports, a jovial and well regarded man who had died when struck by a drunk driver when his son was only 6 years old. The impact of that loss was felt deeply by Robert’s mother who had lost her one true love and withdrew back into herself, shunning social contact. Robert’s father had worked in Insurance and had a life insurance policy that paid out sufficient funds to keep bread on the table after his death but young Robert was soon doing paper deliveries and other odd jobs to supplement this income and was doing chores sweeping garages and stores while his schoolmates were out playing or meeting in social groups.

Robert was a bit of a loner, “the man of the house” from far too young an age and therefore subservient to his mother who dominated who he was and what he did. It was she who eventually took him to the doctors when his voice hadn’t broken and his facial hair hadn’t emerged like all the other boys his age and the shame of being 15 and having your mother report you were lacking testosterone production at that age was just another embarrassment that Robert had to bear. After several tests the Doctors concluded that young Robert’s body was not capable of producing the male hormone without external stimulus and so he was prescribed tablets to take each day.

It was humiliating for Robert to have to swallow a pill each morning and evening to tell his body he was male and should have muscles, hair and a penis that would react to the sight of a pretty young girl. It made him feel less masculine than all the others in school and although his voice did drop in pitch a little, his limbs and face were still largely hair free and his appendage was only fit for passing urine. Not that he felt that really mattered. Robert had no attention from the girls in school and actually felt no sexual attraction whatsoever at the low hormonal levels he was at. When after 9 months of use, the tablets had achieved next to no noticeable improvement in his appearance, Robert gradually stopped taking them, accepting that he was never going to be the sports jock or hunk that the girls went for.

On leaving school Robert took the first job he could find. He now needed to be the breadwinner for his mother and himself and he needed a reliable regular income to support the household. Therefore he took an administrative post within the local government organisation. His upbringing had ensured he was organised and methodical which were ideal values in local government and his mother had drummed in the importance of values and responsibility, having seen the havoc one drunken driver could do to a family.

Robert’s work was mundane and unimaginative but he knew it was a means to an end. It was a way to heat the house and keep its occupants fed and clothed and so just as he had done with the pocket money chores of his youth, he got his head down and worked to his best abilities. His department was composed of 8 females of varying ages so when there was a social event he never joined them, knowing their conversation would be of no interest to him nor his to them. At 5ft 6 inches with size 6 feet and a slim 140lbs in weight he was no target for female attention, so the workplace was just where he spent five days a week and had no other impact on his life.

At home he took his share of the chores although his slender frame meant he wasn’t much use on the heavy tasks around the home or garden. His mother was increasingly less able to take on those tasks either as her mental state deteriorated and she fell into a depression that saw her retiring to her bedroom earlier and earlier each year.

Millicent had been a fashionable young lady when she married Robert’s father and they had enjoyed 15 years of happy marriage travelling together and enjoying each other’s company before they decided to start a family when Millicent was in her mid 30s. Robert’s had been a difficult birth and that made the decision simple – he would be an only child. When tragedy struck and Arthur was taken from her, Millicent boxed up all of the bright, party clothes she had enjoyed wearing and placed them in the loft, unable to throw away their link with the life she shared with her beloved husband but at the same time knowing she would never wear them again as they evoked memories that only brought pain to her mind. The drunk driver had effectively taken her life along with her husbands,

It was when Robert had just turned 30 and his mother 66 that Millicent Mitchell was diagnosed with stage 4 breast cancer. She had found a lump many months before and had done nothing about it, adding it to the list of woes she accepted as being her fate and not telling anyone about until her general health had been affected and Robert had found her crying in pain from a swollen and discoloured breast, He had called a doctor who had arranged for an immediate double mastectomy as traces of the cancer were in both sides. Then the spread was detected and further treatments began. Robert bought his mother prosthetic breasts to try to raise her spirits but the spread of the disease was accelerating and nothing could be done to save her.

The loss of his mother was a great sadness for Robert, although he knew they had never been particularly close due to his mother’s depression and his own diminished sense of worth. He went on cleaning the house and doing the chores as before, only now there was only one mouth to feed. Cleaning out his mother’s bedroom reminded him that there were boxes of her clothes in the loft and he went and brought them back down so that he could prepare the lot for disposal. Perhaps the charity shops would find some of her clothes suitable to sell.

He burst open the first of the boxes and found party frocks that looked as though they had been worn only once. They were still vivid in colour and still had a slight whiff of perfume about them despite being bagged and boxed 24 years before. One dress in particular caught his eye, It looked as if it were made of silk – a simple yet beautiful red oriental dress. He held it in his hands and gasped as it slid through his fingers as though made of liquid. What would something this soft feel like against your skin if you wore it, he asked himself. He felt he needed to find out. He closed the curtains in the room and began to undress.

He knew his mother was relatively close to his own height but he wondered if he was wasting his time contemplating trying it on. One glance at the outfit though made his mind up. He had never seen anything so pretty and soft to the touch and he knew he needed to feel it on his body. Down to his underpants, he reached out and slowly lowered the zip on the back of the dress. Even touching this little area of it sent a tingle down Robert’s spine. His mouth felt dry and beads of sweat were appearing on his brow. He was getting excited by this little red dress, although his appendage remained as flaccid as always.

Robert took a deep breath and slid his head and arms into the dress and pulled it down over his shoulders. He gasped as he felt it ripple down his torso like a waterfall. The dress seemed weightless with barely a pull on the spaghetti straps and although snug to his body, it felt extremely comfortable and didn’t seem to snag anywhere. He managed to get a hand over his shoulder to pull up the back zip and secure the dress in place.

He took a few moments to simply enjoy the feeling of the dress before moving over to the wall mirror in the room. He threw his hand over his mouth when he saw his reflection. The dress looked absolutely gorgeous on him. It was quite short – reaching above the knee – but not in a slutty way. This was an elegant dress that would be set off by a beautiful clutch handbag and a pair of red shoes. As soon as he thought that he turned to the box. Perhaps she has stowed just such accessories in the box!

20 minutes of emptying the boxes later, Robert had found shoes and a handbag that were clearly to be worn with this dress. His mother and him had shared slippers around the house on occasions so he knew his shoe size was much like hers. Of course his foot was slightly broader but all the same, he managed to squeeze them into the red heels. He stood up and chuckled as he wobbled uncertainly on the tall heel before clutching the handbag and stepping once more in front of the mirror. He bit his lip. He looked incredible!

Then he amended that thought. He looked incredible below the neck. Clearly the face and hair was that of a man, and come to think of it, the hands were too. Perhaps a little make up would change that, he thought and turned to where his mother had her make up bag and opened it up to reveal a confusing array of pallets and cylinders, applicators and brushes, potions and lotions that he had no idea how to use and where. He went for the basics and applied some dark red lipstick. Then remembering some TV show where a Drag Queen had talked about disguising cheek bones he added some colour to his cheeks and blended it in to try and disguise his facial structure, before adding a little mascara to his eyelashes and some colour on the brows to raise them a touch and make them look a little thinner.

At every adjustment, Robert had seen his face transform and he began to see that, with practice, he would make himself look more feminine so that he could show off the dress more convincingly. Finding some nail varnish, he slowly applied it to his rounded nails. They were the nails of a working man and he knew they would look far better shaped and extended but at least with the deep pink varnish on, his fingers were already looking more dainty.

Robert then sucked in a deep breath. His mother had a wig. She had been given it by the health board when her own fell out during a bout of chemotherapy but she had refused to wear it, choosing instead to wear a summer hat. Robert found it in its original box at the back of his mother’s wardrobe and was soon placing it on his head and adjusting it so that it looked reasonably realistic. The style was for the older lady and there were flecks of grey in a brunette bob which Robert knew didn’t really go with his face or the dress but even at that, the addition to his make up meant he now no longer saw Robert Mitchell in a dress but a rather attractive female who had the broadest smile on her face and an expression that indicated she had finally found something to like about herself.

Robert caught sight of the clock in the room. It was 1am. He had somehow spent the past 4 hours making himself look like a woman and he needed to stop and get to bed. One thing was for certain though, he would not be taking any boxes to the charity shop, or indeed anything from his mother’s bedroom, until he had sorted them out and decided which outfits he would like to keep because he could see himself spending more time displaying as an attractive young woman rather than the miserable male he had been.

It was 2.30pm before he had carefully removed his mother’s dress and hung it in her closet, along with some others from the boxes, then washed off the make up he had applied and removed the varnish that had spent barely an hour on his nails. It was deflating to see his former self reflecting in the bathroom mirror but at the same time he was excited by the knowledge that this was merely a version of himself and he could transform into something prettier, more desirable and much happier. He went to his bed feeling more positive than he could ever remember feeling.

Over the next two evenings Robert set about categorising his mother’s clothes. Underwear went mainly to the bin but there were some still packed and unworn that he kept, including a couple of bras that were purchased before the mastectomy. The prosthetic breasts were still in their box – a subtle B cup size since his mother was never the busty type – and there were unworn stockings and camisoles too.

Robert had gone on-line and ordered a long black wig which he felt would be more “Asian” in appearance and match the dress better. He marvelled at the websites that offered clothing in all shapes, sizes and colours and realised that he had access to whatever he wanted so long as he could afford it. The make up and perfume options were limitless and daunting but he found an on-line tutorial for transgender male to female make up suggestions and made notes on what tricks would help him look more feminine. All the time he realised that he was feeling an affiliation with the other sex far more than he had done so as a male. He saw that some websites would sell him oestrogen tablets so that he could boost that hormone level within him since his body wasn’t creating testosterone but decided he might discuss the matter with his doctor first. He couldn’t wait for the coming weekend when he could spend time en-femme and embrace his new projection of himself.

- - - - - - - - - - -

Robert rose early that first Saturday morning and breakfasted while planning out his day. He was going to get dressed and made up and if he felt confident enough, go out and take a bus into town and shop for a pair of denims to wear. He wanted some casual feminine clothes that his mother clearly lacked and was confident the body hugging cut of a female jean would still fit him. A nice floral trim would be pretty, and perhaps some joggers wouldn’t go amiss. He would go visit the very charity stores he would have donated to and see if they had some outfits that would suit him. He knew from overhearing the girls at work that these stores were an excellent way to get fashion for a bargain price.

He sat at the vanity in his mother’s old bedroom which he now considered his changing room and began his transformation. He did his make up first because he knew that this was the most important element and would take the longest time. Once he had that element complete, putting on the clothes was a2 minute job. Slowly and carefully he put on foundation and blusher, having learned from the internet how to hide facial hair – although he knew he really had minimal issues in that regard anyway. Then he lined the lips before applying lipstick to fill and a glaze to make it permanent and make it shine. Instantly his mouth became fuller and more sensuous in appearance and he smiled at his reflection.

He worked on his eyes, thankful that he had fair hair on his brows that could be easily disguised with a line of dark make up drawn across the top. His eyes became more prominent, appearing larger and giving his face a far softer appearance. He had spent some time the evening before shaping his nails with an emery board and had applied varnish last night so this morning he simply refreshed the nails that looked like they needed it. His feet looked fine with their own nails varnished now and he paused for a few moments while the nails dried, reminding himself of what remained to be done.

With his nails dry Robert took hold of the prosthetic breasts and the adhesive he needed to use to attach them to his chest. He was excited by the prospect of having breasts for the weekend and was particularly careful to have them correctly aligned. He then slipped on a bra and gasped as his prosthetics balanced in the cups and immediately looked like a part of him. He giggled slightly as the sight of his reflection. This was rapidly becoming someone else and that made Robert feel very happy.

From the closet, he pulled out the beautiful red silk dress and slid it on, noticing immediately how it hung over his new breasts. He shimmied a little as he pulled the dress over his hips and made sure it fitted correctly before pulling the zip on to secure it in place. Slipping his feet into the red shoes felt wonderful and left him with just one final enhancement – his new black wig which he had bought with next day delivery to ensure he had it for the weekend. He had brushed it when he first saw it and left it on the foam head that he bought with it and thought it looked fabulous. Carefully he placed it on his head and pulled it into place. There was a little fringe at the front and then long tresses that fell down below his shoulders which he brushed gently. As he did so he marvelled at the new person who now reflected in the mirror. This was a girl – a beautiful girl – whose eyes sparkled and whose smile shone and was a polar opposite of the drab and mundane male she had been before.

Robert got to his feet and walked over to the full length mirror and giggled. “Hi. I’m kind of new around here” he said from his reflection “My name’s Roberta but all my friends know me as Bobbi. I just love this dress, don’t you? Its so sweet and it feels so soft against my skin!” He pouted and held his head at an angle as he added “Um, could we maybe go out together sometime? Maybe take in a movie or a concert somewhere?” He was speaking in a higher pitch in a voice that sounded like the girls in his office when they chatted together, He chuckled at the thought of blending in with them and becoming part of their social group as Bobbi and finally “fitting in.”

Feeling excited at his transformation Robert walked through the house, getting accustomed to balancing on the high heels and shortening his stride in order to create the correct sway that made his walk more feminine. He switched on the radio and began to sing along with a Taylor Swift song, immersing himself in his new persona and wondering why he hadn’t cross dressed like this before. This felt right, this felt like the way he was meant to be. This felt wonderful!

The doorbell ringing came as a major shock. Robert had all the deliveries he was expecting and rarely received visitors at the door. He decided he would ignore this caller and let them go away. When the bell rang a second time he grew nervous so he went to the peep hole to see if it was one of the neighbours or someone from work. He gave a sigh of relief when he saw it was a total stranger - someone who wouldn’t know him and so in a moment of bravery he decided he would simply open the door and send the stranger on his way.

“Morning, can I help you?” he asked as he stood in the doorway gazing at the smart man in a business suit who was standing outside.

“Good morning! I was looking to speak with Robert Mitchell if he is at home?” the man asked.

“I’m afraid he’s not here at the moment. Can I get him to call you?” Robert said as he tried to send the caller on his way.

“Its regarding his late mother’s estate and I wouldn’t normally call on a weekend but it’s something we need to clear up in order to progress matters.” The man suddenly looked embarrassed and said “Sorry, I should have introduced myself, I’m Scott Parker. From Graeme Parker and Son Solicitors.” He thrust out a hand and added “and you are?”

Robert automatically took the hand offered to him but managed to keep his handshake limp and feminine in nature. “I’m . . . I’m Bobbi, Robert’s . . uh . . .cousin. . . .and I’m just visiting at the moment. He.. .um. . . had to go out to some work related thing this morning and I’m not sure when he’ll be back.”

Damn! This wasn’t any door to door salesman he could shut the door on and Robert knew he wanted his mothers affairs wrapped up as soon as possible so he would be the registered owner of the home he lived in and would have the contents of his mother’s savings accounts deposited into his own to ease his financial worries for a while.

Scott gave a little smile and said “Bobbi it would really take only a couple of minutes if I could come in and show you what’s needed and perhaps Robert could return the forms when he gets back. I’d really appreciate your help?”

There was something in the man’s smile and demeanour that made Robert pause for a split second. Scott used that to seal the deal. “I really appreciate your help, Bobbi” he said and smiled broadly and before he really thought the answer through he opened the door further and said “Well, I guess if it helps Robert and everything . . “

Scott stepped into the house. “Thanks Bobbi, this won’t take long.”

“Please” Robert said as he indicated a seat for Scott to sit on. He chose the sofa and as he thanked his hostess for the invitation, he opened up a satchel he was carrying containing the paperwork that was the reason for his call.

Robert sat in the armchair next to the sofa, careful to sweep his skirt under his backside and to sit with his legs to the side in order to appear as natural and demure as possible. He was nervous presenting as Bobbi for the first time to another person but at the same time he was excited to see how well he could carry the charade and especially when the visitor was so cute.

He caught himself. Did I just call my visitor cute, he thought and then smiled to himself. I guess he is kind of dishy! He took in the man who was searching inside his satchel. Five foot 10 or 11 probably, probably goes to a gym because he has a well toned body, kind of mousy brown hair that’s a little ruffled but in a nice way and a pair of brown come to bed eyes. . .wait did I just call those come to bed eyes? Focus on his shoes – ok, smart black shoes with not too much polish, grey socks, that’s better, and a nice grey suit with a bed tie on a white shirt . . .”

“Bobbi?”

“Em sorry?”

“I said do you live locally?”

“Em, well not so far. Maybe 10 miles or so away.”

Scott smiled. “You must be pretty close with your cousin then?”

“Oh yea” Robert replied. “We’re kind of the same age and grew up together and whatnot.”

“And both still single!” Scott said with a smile.

Robert’s face registered the shock at the statement and Scott quickly added “Only I notice you’re not wearing any rings. Sorry, I shouldn’t be so personal – I hope you’re not offended?

Robert allowed himself a smile as he replied “Oh no, its OK, I guess I just haven’t met Mr Right just yet. Scott’s eyes looked into Robert’s at that remark and the two looked at each other for a moment in silence before Robert glanced down at his hands which were folded together oh his lap,

“It’s a lovely house” Scott said, to change the subject.

“Thanks” Robert replied before realising his mistake. “I mean, Robert looks after it pretty well, he’s got a good eye for décor, always has!

Scott gave a little smile once more as he pulled out some forms. “Here we are, now it’s this section here that we need Robert to review and sign off.” His finger pointed to the bottom third of the form in front of him but he didn’t move it closer to where Robert could see it and instead he looked across and with his eyes seemed to draw Robert across to the sofa.

Robert was drawn by those eyes – those damned cute hazel brown eyes – and moved over to sit next to his visitor on the sofa. Scott smiled a little and took in the fragrance of the person next to him. Her delicate limbs and pretty face were so beguiling he was kind of glad it wasn’t Robert. Bobbi was far more charming company.

“I need Robert to confirm that his mother had no further savings accounts other than those already submitted and that there are no other shareholdings or pensions. He needs to read this section here and then sign off here and date here” Scott said as he slid a little closer to Robert in order to show the section in question. “Now there’s another form here” he added as he brought out a second document. “In this one we need Robert’s approval to close the existing bank accounts and savings accounts in his mother’s name so he needs to sign and date here and here.” He leaned forward pointing to the relevant section making Robert mirror the move until they were both just inches apart leaning over the piece of paper.

Scott turned and looked at Robert and their eyes met once more. “If you could possibly have Robert sign these for me I’d really appreciate it, Bobbi.” They held that position for a few seconds and Robert smiled as he replied “I’ll ask him as soon as he gets back. I’m sure he’ll drop them in to your office on Monday on his way to work” he said and then berated himself for saying something that a cousin wouldn’t know but when Scott didn’t react he decided he had gotten away with the faux pas.

“I‘m sorry, I forget my manners! Can I get you something to drink? Tea or coffee or something?” Robert asked, wanting to appear at ease with the situation. Scott smiled and said “Coffee would be great – no milk, two sweeteners if you have them?” Robert smiled “Yea, we have them. That’s what I take. Hang on I’ll just fix us a mug.”

Scott took stock of his surroundings. The house was neat and well looked after and retained a woman’s taste in décor despite Robert’s mother having passed several weeks before. He smiled as he saw a TV guide beside the television . His own mother bought that religiously week in week out.

Robert returned with the the mugs of coffee and a plate with a few biscuits to accompany. “Thanks!” said Scott. “ Are you by chance watching Dancing With The Stars this season?” He saw his hostess’s face light up. “Yea I am – did you see last Saturday’s show? Wasn’t Jamie Lynn Spears awesome? I mean I know she’s a celeb and has to have danced before but I thought she was just awesome!” gushed Robert.

Scott smiled. “Have you danced yourself, Bobbi?” Robert shook his head sadly. “What, not even at school dances and stuff?” Robert chuckled. “Well, I kind of got pulled around the floor by some dumb guys with two left feet but that doesn’t count. I kind of wish I had done ballet when I was little but you need your mom to put you down for that when you’re only 4 or 5 and I guess she could see my future didn’t lie in tutu’s and tights!”

Scott laughed. “Yea my folks were the same. Kept putting me down for Little League when I couldn’t hit a bull’s ass with a broom!” The pair laughed together, enjoying each other’s company. The continued making small talk as they finished their coffees. This coming together was rapidly having nothing to do with the official paperwork.

A couple of times Robert had snuck some extra looks at his visitor and was liking what he saw. He was a confident, attractive, professional young man that he could talk to easily and he found that he shared a similar taste in music – they had discussed the forthcoming music festival in town which featured acts Robert was also a great fan of.

“You know, Green Day isn’t usually the taste for young girls like you!” Scott had said and Robert had appeared mildly insulted at the comment. “My dad had a copy of American Idiot he wouldn’t stop playing and I guess it became the sound of my childhood and I kind of stuck with the band after that!” Scott smiled and nodded. “Favourite track?” Robert had smiled and said “I kind of like Whatsername and I know it’s the last track on the album and stuff but it kind of wraps up everything before it and leaves you wanting more and everything?”

Scott smiled. “Yea, I get you. I must have all their albums on CD somewhere” and Robert smiled and said “Oh, I’ve got them on vinyl in my room and started to point down the hallway. He immediately realised his mistake and added “back home” but was sure Scott had noticed.

Robert quickly decided he needed to end things before he made any further blunders, and saw that his guest had finished his coffee.. “Is that everything Mr Parker?” he asked.

“Call me Scott, please! Mr Parker is my father!” Scott said with a smile that made Robert feel strangely wonderful in a way he had never done before. “Yes, thanks Bobbi, you’ve been a great help” Scott said getting to his feet.

“It’s been nice meeting you, Scott” Robert said as he walked him to the door. Scott turned and faced him and replied “and you, Bobbi. You’ve been a great help this morning and I hope to see you again perhaps under less sad circumstances.”

They stood in the doorway looking at each other. Robert felt tingles throughout his body as his brain sent him messages he could barely suppress while Scott found himself taking in the complete woman before him that he felt drawn to in a most unprofessional manner.

“I’ll . . . I’ll have Robert phone you” Robert said as he opened the front door and Scott reached into his top pocket and produced a business card. “Here’s my number if he doesn’t already have it. My personal mobile phone is listed so I can be reached anytime” he added with a smile. He took one more look at his host and said “It’s been really lovely meeting you. Thanks again, Bobbi” and walked down the path to his car.

Robert closed the door and let out the deepest sigh he had ever made. So many emotions were racing through him at that moment. There was also the confidence that came from having entertained another man who thought he was a woman and so he decided while he felt that buzz it would be a good time to go shopping for those extra items he wanted to add to his wardrobe. It was time to go downtown.

(to be continued . . .)