A Strange Romance

I spent the next twenty four hours unable to think about anything other that what I should do? I did not dress or even touch my PC as I sat there reading and then re-reading the letter and forms. In the end it was the realisation that I needed the money and really had no choice. Sure I knew that if I was lucky and lived very frugally I might be able to get a something that covered my mortgage and living expenses but the chances of finding something that paid anything even close to what I had been earning was unlikely and getting another job offer like the package the letter was offering, well that was just a pipe dream! The question I was asking myself was could I actually go through with it especially after I read through the contract, which laid out in black and white that to meet the Master Scott's employment conditions I would have live 24/7 as a woman at home. It also stipulated that I would only be permitted to possess only one set of male clothing which if I wished I could wear in public until they either wore out or I ceased to be able to pass convincingly as a male.

Before I made up my mind I looked up WS&T Developments and found that it they were listed venture capitalists who specialised in financing technology start ups, which was reassuring that there was something real about the offer. In the end I signed the forms and walked down to the post office to post them feeling more than a little freaked out by the enormity of what I was letting myself in for. I spent the rest of the afternoon wandering round Bedford feeling a little dazed. I did wonder what on earth the neighbours were going to say, until it occurred to me that they probably would not even notice. If I had said ten words to both of them since I moved in last year I would have been surprised. Like me they kept themselves to themselves, and as the three flats all had separate entrances I only saw them once in a blue moon.

I heard nothing back for over a week and I was beginning to think that it had all been a sick joke when I got a second letter containing a return train ticket to London and a pair of appointment cards. The first one for 10.30 in a morning was to see someone called Linda Scott, and the second at 2.00 in the afternoon was more worryingly for a consultation with a Harley Street doctor. Strangely even though I knew he was back off his holidays after he sent me an I'm back email and a request not to mention the D&S games we had played on line, Master Scott had not been on-line, but having looked up WS&T I assumed he was just busy getting caught up with work.

A week and later and suffering from a gut wrenching bout of apprehension I caught the train into London, wondering what was going to happen. In the end it turned out to be a waste of good worrying as Linda turned out to gender psychologist who after ninety minutes of chatting actually put my mind somewhat at ease about why I had always felt isolated and found it hard to make friends when she explained that it was a very common issue for people who suffered from gender identity issues like mine.

"I see you been self medicating hormones for two months?" She asked, glancing at one of the forms she had on me, "That was very foolish you know?"

I blushed shocked that Master Scott had been making me take hormones for weeks with out telling me even though a little voice in my head was telling me I told you so but thankfully she did not pry and I assumed she read my blush as embarrassment.

"But I can see no reason why you should not be on such medication and since you are going to take them anyway I would rather you were taking ones I knew about," and handed me a script for hormones. "I will see you three weeks and I'll expect you to attend dressed in roll, okay Jane?"

I nodded, swallowing dryly.

Linda smiled, "Good your appointment is for 10.30 again, and after a little chat we'll go for a walk round and may be a coffee if you feel up to it?"

I was not sure I was ready to actually do that with her, but it was clear that I was going to have to, and I was still worrying about that when I arrived at Harley Street.

Seeing the doctor was a little nerve racking mainly because he did not say very much as he gave me complete examination commenting as he glanced through the forms (which I recognised as the releases I had signed the previous week) that he would fit me in next week for my first treatment. Annoyingly he did not tell me what the treatment was for but I could guess as he spent rather a lot of time examining my chest and in particular my nipples commenting that I was already showing signs of development. With a half smile he handed me an appointment card for the following week at Charring Cross Hospital as he informed me in that brusque way doctors have to make arrangements to be away from home for up to 72 hours and ended the consultation.

Since I had two hours to kill before my train back to Bedford I left the doctors debating whether or not to do some damage to my credit card with a little retail therapy when a tall raven haired woman waiting outside said, "You must be Jane?"

I blushed and nodded.

"Good! I am Miss Evans and your Master has hired me to insure that you keep to the conditions he has discussed with you. Now come along girl we have a lot to do and discuss and we don't have much time before your train home."

The do consisted of shopping with a card that Miss Evans had, and the discussing was her telling me that she would be making at least one personal visit to my home a week. These visits would be at random times and with out warning, as well as checking on me via my web cam to insure that I was always in compliance with Master Scott's condition that I lived 24/7 as a girl. It was all a little overwhelming as the enormity of what I had agreed to began to sink in when she explained that I had to inform her of my every absence from my home regardless of if it was for say a hairdressers appointment or even if I was just going shopping. I was to email and inform her of the times I would be out and where I was going as well as carrying with me at all times a pink 'Barbie' mobile phone with a camera so that if she needed to check on me she could contact me at any time.

When I asked why she said firmly. "For the next twelve months you are no longer a free person sissy! You are property, owned by your Master, and don't you forget it! As I am your Master's appointed agent it is my responsibility to make sure that his property is kept safe."

"Oh!" I blushed at her words, asking myself what was to become my favourite question over the next few weeks. "What the hell had I got myself into?"

"Now I believe you are booked in at Charring Cross next week?" She asked during the 'supermarket sweep' she took me of around a half dozen shops and boutiques that left me laden down with bags full of lingerie, make up, shoes, along with 'business' and casual wear.

"Um yes Miss." I said, "Next, Tuesday, Wednesday, and Thursday."

"Any problems with that?"

"Not really Miss," I said adding, "Other than getting hold of the cattery and booking Sog in with them, but that is about it."

"Sog?" She laughed, "Strange name for a cat?"

"Short for Soggy, which is what he was when I found him soaked to the skin last winter on my doorstep."

"Well a cat is a very acceptable pet, but don't worry about the cattery I will look after him for you since I will be there while you are in Charring Cross."

She must have seen the question in my face because she added before I could ask.

"Your Master has instructed me to install a web-cam network so he can observe your development as well as asking me to oversee any alterations I see fit to your home so that his property resides in a fittingly feminine environment."

Time was getting on and with out any more ado Miss Evans got my keys copied, and put me back on the train to Bedford telling me that I was to dispose of all my male clothes and accessories except for one pair of pants, one shirt, one pair of shoes and a jacket that had to be of a unisex design. Oddly although Miss Evans scared the crap out of me when we met, I quickly came to like her, and before my contract was done saw her more as a friend than my keeper.

I was just through the door of the house when my new mobile trilled with the tune of Donna Summers I feel Love.

"Hello?" I said sheepishly.

"Hello Sissy Jane." Master Scott said into my ear, "Its your Master here?"

"Hello Master." I felt myself blushing.

"Did you have a good day today my pet?"

"Oh yes Master, it was a little strange but fun." I said, feeling rather shaky with the relief at hearing his voice.

"Good girl I want you to have fun." He chuckled. "Have you tried any of your new outfits yet?"

"Um no not yet Master I'm only just home as the train was delayed at Luton for 40 minutes."

"Well I am just calling to say I will be a little busy with work over the next few months and wont be on line to chat as often as I would like, but I will be keeping tabs on your progress and will call when I have the time. Now I believe Miss Sandy has explained how things will proceed over the next few weeks?"

"Yes Master." I said feeling a mixture of emotions.

"Good then I have a few instructions for you," he chuckled, "I would like you to turn on your web cam and keep it on when ever you are home from now on so I can watch you when ever I require. I have set my computer to record your stream and will decide what outfits I would like you to wear each day and email or message you with the instruction for the following day each evening is that understood?"

"Yes Master." I answered. In the background behind him I heard a voice calling, "Mr Temple your car is here sir?"

"Good girl, now I am very busy just now, so I must leave you. Now I expect you to obey Miss Sandy as she speaks for me, good bye my lovely sissy."

"Good bye Master?" I whispered, to the sound of him laughing.

The following week I was suffering from every kind of anxiety under the sun as I signed into Charring Cross, and was shown to my room. After confirming that as requested I had not eaten or drank anything in the last six hours I was examined by the surgeon performing my augmentation. After a quick examination he left me to change into a surgical gown, and a little later I was taken down to the theatre and told to get on to a waiting hospital trolley. Moments later a pretty nurse walked in and injected me with something that put me in la-la land. As I started to drift off I could not believe I was going through with this, and was about to be wheeled into an operating theatre for a breast augmentation operation. Hell only a month ago the concept of something like this was just an on line fantasy and yet here I was about to turn that fantasy a reality!

When I came round four hours later I felt like I had been repeatedly punched in the chest by Mike Tyson. When I looked down at my chest I thought I was going to faint because it looked huge! Most of what I was seeing was actually supports to shape my new breasts and bandages but I did not know that at the time and felt sickened by what I had let them do to me. Thankfully not long after I came round another nurse arrived and gave me a little something for the pain, which must have made me doze off for a while because when I came round again Miss Evans was sat beside me with a tender smile on her face, telling me to relax and take it easy.

"Well you will be pleased to know that both your procedures went to perfectly Jane," she told me with a smile, "You have a perfect pair of jugs under all that bandaging and a very kissable looking pout to your lips?"

I wanted to ask how big they were, but all came out with was, "Both?" In a very croaky tone as she held the water bottle straw to my now tender feeling lips.

"Yes Jane," she smiled, "While you were under I got them to sculpt you a nice pair of proper cocksuckers lips with a pretty cupids bow. Want to see? They are a little swollen just now but when they calm down you'll see that you have a the lips of a born cocksucker."

Oh god! I could not believe what I was seeing when she held up a small compact mirror and showed me my swollen lips.

"I think," she said smiling broadly, "That your Master will be rather pleased with what he's just bought! You have a mouth ringed by big cock pleasing lips and with your bulging 'D' cup knockers, hell girl at this rate you're going to be every guys shemale wet dream!"

After thirty six hours my bandages were removed and my new boobs were given a check over by my surgeon. As he replaced the supports and re-bandaged my chest he cleared me for discharge the following morning and gave me another injection. The jab was a pretty potent painkiller because as I started to fade out I distantly heard him talking to 'my' nurse that I should be healed enough not to need the the support and bandages from tomorrow, and that he would send down a prescription for a course of painkillers for me to take after I was discharged.

What ever was in the injection was enough to knock me out until around 7am the following morning, and after a surprisingly good breakfast for hospital food, my nurse was back to unwrap me for good. It was not until after she had gone that I finally got a chance to see for the first time my new boobs in all their glory, and Miss Sandy arrived just in time to see my reaction.

Oh my god they were huge there was no way I was going to be able to hide them! How on earth was I going to be able to wear my one set of male clothing with these monsters in my chest?

As Miss Sandy helped me to my feet I immediately felt the change in my centre of gravity and the strain the added weight in my chest was putting on my back! As I sat on the edge of my hospital bed stunned, Miss Sandy whipped out my phone to record my blushes before she got me to pose for a couple of topless photograph for Master Scott. My breasts were incredibly tender and when she showed me the images she had shot I could see the bruising the surgery had caused on the sides of my body. However that was all secondary to the relief I felt to have them contained in the new black satin bra she had brought in for me. Cupping them into a twin satin bra cups that first time felt really, really weird but to be honest even with the bra they still hurt like hell! The pain was just about bearable and nothing like the agony I had been in for the few moments they were freely bobbing around!

Even so they were still extremely painful and just dressing had me biting my tongue as I slipped a soft rose pink blouse over my bra and fastened the buttons. The pain was enough that it did not occur to me that instead of the jeans and sweatshirt I had arrived in I was leaving wearing a blouse and a ¾ length 'studentish' peasant skirt with my lowest heels! Since I could not lift my arms with any degree of ease Miss Sandy quickly made up my face and fixed my blonde wig on my head before she judged me fit to leave the hospital.

I was that shell shocked from finding out that instead of the B cups I expected I had been give D's combined with the agony my chest was in when I walked I did not even notice that I was in public dressed as Jane until we in her car. It might only have been a short distance my room to the car park but it felt to me like a marathon and I was exhausted by the time I was sat in the passenger seat. Every single step had sent sharp stabbing bolts of pain through my hypersensitive boobs.

The drive home was equally painful because even though my new boobs were contained in a very supportive bra every ripple on the road caused them to painfully jiggle about. Thankfully Miss Sandy kept up a steady stream of friendly chatter that went some way towards distracting me from the twin mounds of agony thrusting from my chest.

"Oh my god!" I whispered when I walked into my completely changed home.

God knows how she did it but in the two and a half days I was away, my once Spartan single blokes flat had been transformed into a completely feminine place decorated in pastel shades with vases of flowers and numerous photographs of Master Scott on the walls, one or two of which had been digitally manipulated to place me as Jane in them beside him!

All my old second hand furniture had been replaced with matching fixtures and my bedroom was like something from little girls story, with its huge double canopied bed, a matching dressing table with a large make up mirror, fitted wardrobe and chest of draws containing more clothing than I had ever owned in my life. Along with Soggy who looked very comfortable sleeping in the middle of the pink bedspread, my bed was decorated with teddy bears and soft toys. On the shelves where once a pile of technology books and computer games had resided there were a couple of Barbie dolls and a small selection of romantic novels along a few my old books that Sandy felt were acceptable in my new life! Although I did not notice them at first every room including the bathroom had at least one web cam, a microphone and a speaker so Master Scott or Miss Sandy could watch and talk to me as I went about my daily chores.

I guess if anyone had been able to look into my flat they probably would have thought I was crazy woman who talked to herself constantly at times except I was not talking to myself. Although Master Scott was (to my knowledge) in California most of the time his disembodied voice often filled my flat as he commented on my physical 'improvements' or involved me in long conversations about everything from the state of the world to some of the most weirdly kinky subjects imaginable. His physical presence might have been miles away but his personality filled my life and I was constantly aware that he could be observing my every moment.

It took me about ten days before my boobs to stopped hurting and get over the operation, and another couple of weeks before all the residual bruising faded. Having dreamed of having real breasts on and off for years the reality of actually having a pair of 'fun bags' was a startling experience for me. At first I found that they got in the way all the time but as I got used to their constant presence I found that to compensate for their presence I was starting to unconsciously alter how I went about things, because regardless of what I was doing I was intensely aware that they were now physically a part of me. Even the slightest movement like picking up a cup a turning a page in my book caused them bob and sway on my chest constantly reminding me that to feel comfortable I now needed to be wearing well fitted bra to support and control them!

To help me settle into my new lifestyle Miss Sandy regimented my days with a detailed timetable that laid out what I should be doing when. She timetabled everything from things like doing my housework to when I should be studying feminine deportment and lifestyle training DVD's or exercising and improving my flexibility with erotic dancer tutorial disks. After the mind numbing monotony of my old job I suddenly found I was always busy and yet oddly there were times when I felt that it was in many ways my life had hardly changed. This was probably because the biggest difference in my life was the requirement to act feminine which was something I had already spent much of the last few months doing. After all even before I met and contracted myself to Master Scott I had already spent much of my time at home crossdressed! One thing that did however change now I was contractually obliged to be live as Jane was it somehow actually freed me from the life long feeling of shame that my pleasure in dressing and acting feminine once generated.

Encouraged by Master Scott, Miss Sandy and Linda to explore and experiment with different clothes and make ups I found that the emotional isolation I had felt since puberty was staring to fade. I guess now I felt free to indulged myself in the fun of being a girl which erased one of the main causes of why I felt so isolated. Eventually I fell into a routine, of a morning I would do my housework, and if needed get in to 'man drag' and go shopping. Given the choice I would have ordered my weekly shop over the internet from Tesco's direct but Miss Sandy forbade that, which meant I had to put up with the hassle of having to painfully bind up my boobs before I could hide them under a baggy jumper and regardless of the weather outside I always had to wear an oversized jacket.