A Strange Romance

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was 14 to move back to their home town of Newcastle from Bedfordshire I had wanted to go back there, and the job was an opportunity to do just that and one I was not going to turn down.

I have often wondered if the move up north at a vulnerable age triggered my crossdressing or if the latent desire was there all along? Anyway I was like a duck out of water in Newcastle my accent did not fit, I did not understand football or any of their cultural references which left me feeling isolated and lonely. One day during the school holidays when I was bored I found my self dressing in my sisters old school uniform and it really turned me on. The discovery that I got a sexually buzz from looking like a girl just compounded the isolation I already felt and that sense of being different stayed with me even through university. Although there were cross dressers and the like at the university I was to ashamed to admit my linking and having lost access to my sisters things when I left home there was no longer the opportunity to dress up. I guess a part of me thought I that had left my crossdressing behind as the hedonistic environment of the college forced me to become a little more outward going but I was never going to be the most gregarious of people.

Moving back to Bedfordshire felt to me like I was able to wipe out the six unhappy years I spent in Newcastle and I even starting to build something approaching a social life through work when the company I worked for merged with another retailers. After a merger the company restructured and centralised their IT operations to Glasgow and for a few weeks it looked like I would have to move again, which to my mind was not an option! Thankfully as all my job required was a fast internet connection and a phone line my new boss gave me the option of either moving, which would cost me a bomb in penalties on my flats mortgage, or working from home. Since I had finally got back to Bedfordshire I really did not want to move again so I said yes to the home working offer and rather foolishly expected that working from home would be great but in truth it it was awful. I was used to working with people face to face and now my human contact was cut down to emails, IM's, the old lady in the corner shop and the supermarket check out!

I think I could have gone a little crazy if I had not found a kitten, or rather had one adopt me last winter. I had been shopping and when I got home I found a little kitten sheltering from the biting winter wind shivering on my doorstep. When I bent down to pick him up intending to take him to the RSPCA he meowed at me and my fate was sealed I was now a cat owner!

Even with Soggy (as I came to call the cat) to keep me company it was not long before the lack of human contact wakened my old crossdressing habits and as I no longer had the expense of travelling I suddenly had a sizeable disposable income I had the money to indulge myself. Although the freedom to dress for work was fun the distraction did not solve the underlying problem which was the lack of human contact in my life. I still found it really hard to make friends and started to using some of the chat pages on the websites I frequented. At first it was just the news and technology places but one day out of curiosity I drifted into a transvestite room and had a whole new world opened to me.

Before I knew it I was frequently chatting with strangers as Jane. I was to shy at first to post a profile image but when someone asked what I looked like around Christmas I plucked up the courage to add one of me dressed to my profile and I got a real kick from the compliments that came back about my appearance. On the same day, I began to attract a significant number of private messages off men. I had got messaged by men in the past and I usually ignored them until I got one that evening which caught my attention off someone called 'Sissy Trainer'. This was unusual for me as I normally chatted with other CD's and my new Internet friend made no secret about being dominant and male. It was around 10pm on a Friday night and having needed a couple of glasses of 'Dutch courage' wine to take my profile photos, my inhibitions had been artificially relaxed before he hit on me with a private message.

Sissy Trainer >Hi Sissy! You look cute!

Jane-CD > Why thank you, its nice to know my efforts have been appreciated.

Sissy Trainer > Oh they are.

I had seen him in the room before but never chatted to him directly either by IM or in the open room but his comments about general topics were usually entertaining if a little naughty so I added my ASL (age, sex location).

Jane-CD> 23, m-cd, uk

Sissy Trainer> Nice!

We type chatted for may be twenty minutes about nothing much more than him addressing me as 'Sissy' as he quizzing me about my dressing habits. It was kind of embarrassing and exciting to be called that and I felt a flicker of regret as his chat had been entertaining when he told me he had to log for an hour or two.

Jane-CD > OK, I'll see you over the weekend?

Sissy Trainer> Oh sooner than that I hope Sissy! I'll be back on once I'm home.

Jane-CD> Oh, well I'm not going out so I'll likely still be on line but may be not in here?

Sissy Trainer> You got Yahoo messenger then Sissy?

Jane-CD > I don't have yahoo IM sorry.

Sissy Trainer > So its free? Download it now girl! I expect to find when I get home that you have it set up an account under the name Sissy Jane and sent me (Sissy Trainer) an invite to join you, understood Sissy?

Jane-CD> Yes.

Sissy Trainer> Yes what you dumb bitch?

Jane-CD> Yes Sir.

Sissy Trainer> Close enough for now!

With out any ado he logged out leaving me sat in front of my PC feeling shocked, and shamefully strangely turned on. I guess like many deeply closeted crossdressers I have something of a submissive side, and Sissy Trainer was clearly familiar enough with closeted psychology to know how push the right buttons to get the likes of me to comply, because I did as he wanted.

As promised he was back on line about ninety minutes later and I got an erotic shock when my IM dinged for the first time.

Sissy Trainer> Good! Already on line and waiting! I like a sissy who does as she is told.

Sissy Jane> Er Thank you sir

Sissy Trainer> Which makes me ask the question just how submissive are you Sissy, because I think you could be just the kind of submissive sissy bitch I'm looking for?

Now normally I would have ended a conversation after a message like that from a bloke with a handle like his but he had been very persistent in his questions earlier and I'd be lying if I said I was not thrilled that he had got back to me so soon and I answered him.

Sissy Jane> And what kind is that?

Sissy Trainer> One who knows her place is to please her owner, Sissy

Sissy Jane> Oh?

Sissy Trainer> Would you like to please your owner Sissy Jane? To surrender your pathetic attempts at pretending to be a man and become the sissy of a Master's dreams?

Could I? I felt a strange shiver that mixed humiliation with a darkly erotic thrill which made my cock twitch in my panties as I typed.

Sissy Jane> Perhaps

Sissy Trainer > Don't you mean, "Perhaps" Master?

I guess it was the booze that made me reply.

Sissy Jane > That is a title that needs to be earned sir.

Sissy Trainer > (Grins) Does it now you pretty little tease? Then I'll just have to see about earning it off you sissy Jane!

Since I was usually on-line from about 9am until midnight we were able to chat when ever he was on which was usually from around 2 or 3pm so I assumed he was in the States. He had a decidedly dominant edge to his messages but that edge was tempered by a teasing sense of humour which I warmed too and when ever we were on line together he would message me and over subsequent chats he manoeuvred the conversation from vanilla dressing into one about sexual fantasies. Although it took him a while to break down my reticence I started to tell him about my kinky desires and at some point along the way I started to call him Master!

Perhaps it was the way he took my kinky ideas and fantasies and then put his own spin on them which kept me chatting with him, and with out realising it was happening his words were slowly altering the way I perceived my darker fantasies. It was a real turn on for me as Sissy Trainer taunted and teased me with promises that if we ever met in real life he would make me wear a polished steel collar with Sissy Jane Property of Master ST engraved on it. He also took a comment of mine about a fantasy I had about being forced to get vivid bikini lines suntanned onto my body and twisted it into how he would make make me take hormones and transition into his full time feminised slave. Permanently bonded to him by making me get his initials and slave mark indelibly tattooed on my body. Only a few weeks earlier topics like this would never have turned me on, but after talking about such things with him I was now more than willing to roll play being this man's sissy sex-toy!

I was hooked and when he started to ask me to send him photographs of me posed to his taste to show him my small wardrobe of feminine clothing I tried to avoid it. I'll be honest I was not keen on doing it but he took the first step by sending me a some of him, a head shot, one of him wearing a minuscule swimming costume, in a business suit and finally leaning against a huge motorcycle wearing leather biker gear. Even though I felt I was straight I see he was a real 'hunk' of a man! He was in his mid to late thirties with a gym honed body, commanding slate grey eyes dominating his handsome face under a head of dark cropped hair. On his chest was a thick mass of wiry dark hair and his right upper arm was tattooed with one of those American Greek university fraternity symbols.

Sissy Trainer> I bet just looking at your Masters virile manly body has your useless sissy clitty aching in your lacy panties? I am sure you cannot wait to get them framed and hanging all over your boudoir so you can look at me from your bed and dream of serving me like the slut slave you desire!

Sissy Jane> Mm. Yes Master!

What I did not realise was now he knew what I had in my feminine wardrobe it allowed him to dictate to me how he wanted me to dress when we chatted and he did. With out realising what was happening I was starting to become obedient, and some two months after we started talking on-line he asked.

Sissy Trainer> Have you a web cam Sissy Jane?

Sissy Jane> No master, I don't own a web cam.

Sissy Trainer > Go and buy one today bitch. I have decided that if I am at home with you I wish to see what my property is doing!

Sissy Jane > Yes Master, what sort shall I get?

Sissy Trainer > Any will do so long as it's got good resolution and a microphone.

I was that into out little game that I went out and bought myself a wireless one first thing the following morning. Thankfully I had enough sense to change into something feminine before I set up the software and plugged it in because he was already waiting on-line for me as I logged in.

Sissy Trainer > Did you get it slut?

Sissy Jane > Yes Master.

Sissy Trainer > Good, turn it on now slut, and activate the microphone I want to be able to talk to my sissy bitch!

Now he had me on his screen, and could speak rather than type Sissy Trainer upped the anti little by little. First he got me to show him my undies, then he got me to kneel before my web-cam when he was speaking to me. He began to insist that I curtseyed to him when ever he came on or went off line. I'll admit tarting dressed as a girl in front of my web cam for him and learning to give him a virtual lap dance was a lot of fun.

We used the web cam a lot or rather I did, as Master only turned his on when he was at home and could use his microphone. Sometimes when he was busy at work he would ask me to leave my cam on so he could 'keep an eye on me' even when I was not dressed for him. I never knew when he would be watching but I willingly played along not seeing that what he was doing was extending his control over me into my 'real' life. With almost telepathic timing just as the thrill of using the web cam started to fade Master showed me a pair of slutty chandelier earrings and a belly button ring with a heart shaped pendent engraved with ST hanging from it.

Sissy Trainer > I would like to see you wearing these my Sissy.

I was that caught up in our on line fantasy that I gave him my address with out thinking about it!

May be a week later the postman delivered me a large box containing the ear and belly button rings along with a set of very sexy looking lingerie and a pair of fully fashioned seemed stockings. To complete the look the box also included a seriously spiky pair of five inch heels with locking ankle straps. Much to my surprise the label included the real name of my internet friend, Scott Temple which explained the ST but instead of an address all I got was a return code.

Obviously I could not wait to showed off the outfit he had sent me and I waited feeling like I was about to explode with excitement until he logged in from work mid afternoon with the comment.

Sissy Trainer > Have you got your new rings in?

Sissy Jane> Not yet Master.

My ears were not pierced at this point, and before I could continue tell him, he typed.

Sissy Trainer > Do not to contact me again until you have the photographic evidence that you have been a good sissy slut and got holes pierced for your Masters presents!

Then he promptly logged off!

The idea of losing my on-line Master was enough to scare me into going out almost immediately and getting both my ears and belly button pierced for him! Considering that until I started hanging in TG chat rooms I never would have done anything like this my behaviour astounded me! I like to think he was waiting for them because with in minutes of sending him the photographs that evening Master Scott logged in and we chatted for an hour or so before I began to fall asleep!

The rings, lingerie and heels were just the start of his presents. Although I did not see it at the time all the outfits and items had one thing in common they reinforced my submission to him as he sent me a very sluttish secretary's outfit which he teasingly told me to wear during his work hours so I could get used to wearing sexy office wear before he made me come to work for him. He also sent me submissive girl fetish club outfits and best of all a very sexy maids uniform which he told me to always wear when I did my housework, so I was properly outfitted if he decided to look in on my web cam while I was (as he put it) training for my future as a slave wife!

He knew I got off on surrendering control and kept reminding me about how he was going to have me transformed me into his idea of the perfect trophy sissy to decorate his arm. Reiterating how I would one day be forced to take hormones, get breast implants and tattooed eye-liner to reinforce my place in his life as his feminised bitch! One rather worrying development was alongside one of his little presents, a butt plug that he cast in front of me over his web cam from the top three inches of his cock was a blister pack of tablets! Although he called them vitamins I had a sneaking suspicion they might have been hormones as he insisted on me taking them when he was watching over the web-cam link. I kept meaning to ask him but worried that he might 'dump' me I obeyed his command that I took them in his presence!

The butt plug was a scarily exciting looking thing, and at first I had no intention of ever using, but as ever Master Scott got his way and when I finally plucked up the courage to use it for him my cock had never ever been as hard!

I guess it was the total break Master Scott's demands made from the repetitive reality of my life that made our long daily chats the highlight of my life, because by now we had gone past just chatting about our kinks but our real lives. I learned he managed his own business, was 36 years old and although he had been in the States since his teens his family was British. The relationship might have been over a pc link but it had become for me a quite real for me and when the credit crunch started to bite I could not stop myself telling him my worries about the security of my job when it became apparent that my employers were getting into difficulties.

Sissy Trainer > Well if the worst comes to pass that offer still stands for you to contract to me for a year?

Sissy Jane> How you are there and I am here?

Sissy Trainer> It depends on what you are doing, after all you work from home just now and I can use you in the same way.

Sissy Jane> Doing what updating website's?

Sissy Trainer> Something like that, and I am sure you would enjoy the bonuses (lewd wink) Let me think things through and I'll put something together just in case.

I did not think anything would come of it and started sending out my CV to anyone and everyone I could think of because having seen the news I felt sure from the sudden drop in business I was seeing in the on-line operation which had been the one part of the business making a profit that my employers were going to go bust! My fears were proved right when a week later when the company went in to liquidation and was made redundant. I was at my wits end my savings and what was left of my inheritance after buying my flat would just about meet my mortgage payment and bills for this month and with my redundancy payment may be next month but after that I was in the shit! Making things worse was Master Scott was away on business for a couple of weeks so I could not even talk to anyone about my fears and I was in a rare old state when the a day or two later the postman delivered me a large official looking letter. Preying that it was an interview offer, I tore it open and saw it was from a solicitors with an a London address.

Dear Mr Lane

In reference to your application for the advertised post of private personal UK assistant to Mr Temple of WS&T Development at the salary ($120,000 US) agreed at interview. We are pleased to inform you that your application was successful. As per Mr Temple's request appointment to this post is for a minimum of one year and is subject to your agreement to undertake to his satisfaction certain conditions during a three month probationary period.

As a PPA to Mr Temple, WS&T undertakes to maintain your mortgage payments, the properties running costs and associated expenses. However after the payment of a signing bonus of $10,000 US, you will only receive a weekly allowance for personal expenses while the balance of your salary is to be paid into a trust account that you will gain access, assuming you have met Mr Temples criteria, on completion of the contract. Should you wish to accept this position please complete the attached forms with the signed contract of employment and return them along with all the listed personal identification in the provided envelope as soon as possible.

Yours Truly.

J Howard.

Satchel and Butler Solicitors.

I could not believe what I what I had in front of me. A quick bit of rough maths in my head told me that the job was offering nearly four times what I was on at present! Over a cup of tea I re-read the part about conditions and was able to take a guess at what some of them would be.

"Oh my god!" I whispered to myself, aware that when Master Scott had said I could work for him I thought he was joking but as I read through the letter a second time and looked through the forms I saw that that his offer was very real. So real that the there were forms for the Inland Revenue for resident UK nationals receiving annual salary in foreign currency, along with the usual National Insurance pay as you earn and health forms. Health forms which also included rather scarily a couple of releases for breast augmentation and associated treatments. Obviously the enormity of the letters contents caught me off guard and left me feeling a mixture of relief, excitement and the somewhat embarrassing realisation that if I accepted the position then the feminine roll Master Scott envisaged for me would step from fantasy into the realm of cold hard reality.