My New Life Ch. 01 - A New Beginning

Chapter One- A New Beginning.

I had been successful in keeping my little crossdressing fetish secret from my wife and stepson for nearly two years, during this time I became very proficient in getting dressed in stockings, corsets, tight skirts, walking in high heels and make up, along with using the perfume that I bought for my wife. During these sessions I would strut my stuff throughout the house, bending over whenever I passed a mirror, the micro leather mini skirt raising up and exposing my stocking tops and tight panted covered butt. I loved the black high heeled thigh high boots that I bought supposedly for my wife, that I just managed to fit in, they were a tight fit but squeezed my toes and thighs tight making me walk like a super model. The static sound the stockings made, and the click clack of the heels on the wooden floor all helped in programming my mind to accepting being a crossdresser.

I had also obtained several sexy outfits from various places, two were my favourites, a sexy maids outfit with lots of flouncy petticoats that when I bent over at my waist, they lifted the black outer skirt and apron bows, so that my black ruffled panties, stocking tops and garters were on full display. This uniform came with some very high heeled shoes of at least 150mm, this extra height straightened my legs and made it nigh on impossible to walk in at first, but I soon acquired the ability to walk around the house.

My other favourite outfit was a schoolgirl one, short above the knee tartan skirt in blue checks, white knee-high socks black flat shoes, white silk blouse with white cotton panties and bra all topped off with a black blazer with a head band and ponytail. To add insult to injury I became immediately hard and came without ever touching my cock when I wore either of these outfits, always making a mess in my panties.

What I did not realise was that these outfits I liked the most meant I was far more submissive than I realised, certainly the maid and schoolgirl ones, whilst the leather miniskirt and boots these three outfits just screamed "fuck me now". The other lingerie was just far too sexy to contemplate if I was a submissive guy who liked dressing up or a sissy waiting for a master or mistress to take her!

As mentioned I liked the most the micro leather mini skirt, black corset, stockings and ruffled burlesque pantie shorts, topped off with the thigh high boots and black tank top and choker. My fake tits really filled out the bust on the corset and made my chest look great in the low-cut tank top. The other outfits mainly included sexy lingerie from corsets to garters in several colours, Black, white, light, baby or sky blue and pink. My what would be considered day wear was mainly miniskirts, hobble skirts with blouses and tank tops, halter neck mini dress and high heeled shoes, some very high ones indeed. I had been amassing my collection of women's cloths now for over two years and felt confident in my abilities to pass convincingly as a burgeoning crossdresser.

It would lead to marathon wanking sessions lasting a few hours, each time I came hard and always finished up in eating my cum from either the floor, panties or the toes of shoes and boots. About this time, I was looking at shemale porn when I came across a shemale doing dildo practice and giving instructions on how to be a complete cock sucking sissy, she was using an ejaculating dildo and cum substitute. She had a collar on that said CUMSLUT and a full leather body harness, along with this she wore thigh high boots. This was not my first look at BDSM gear on a shemale, but somehow this time it resonated with my mind, and I grew a little harder as I followed her JOI instructions.

From this I looked a femdom sites and started to think about my wife being my Mistress, this soon turned into a Mistress and her shemale sub being fucked and sucking big strap-on dildos and of course the sub was begging for more. I just could not get enough of this type of porn, and I mentally put myself in the subs position. From here I took to looking at shemales getting fucked by men and women it all added to my sexual fantasies. I even started to find stories on the WWW. And bought many books online that featured crossdressing either voluntary or forced, some of the pictures really turned me on as did the stories.

All this, my secret life I managed to keep from my wife and stepson but that was soon to change!

My wife told us both over breakfast that day that she would be away for six to eight weeks working on a special commission for a very wealthy man. She would have access to a private jet, helicopter and small man-made private Island in the Mediterranean Sea, she would also be paid on completion two million pounds. I was sceptical and said that the offer was too good to be true, until she showed me the agreement all signed and duly certified. She also said that at the end of the commission we would all be invited to meet the man on his Island for a three-week holiday, all expenses paid!

She would be leaving at the end of the week and that she would be adding some extra security to the house for our absence later. It was one of the stipulations of the contract that had to be adhered to, the other was that she was not to have any contact with both of us for at least three weeks from date of arrival. She explained that the first few weeks were always the hardest in starting a new commission and she needed to be focused on the task in hand for it to succeed, and that two million was a lot of money to lose by starting off in a slipshod fashion.

Bradly our stepson immediately piped in and said he would be away for the first two weeks of her trip and when he comes back would stay mostly at a friend's house and go to the gym. He needed more body mass to complete his bouncers course, so he and his friend would work out together most days of the week. This got my mind to thinking perhaps I should book some leave as well, but I won't tell either of them then I can dress up for a few days at a time and really immerse myself in my crossdresser persona of "Kimberly".

I always wanted to try fake boobs and I had found a set on the www; this set had a mechanical implant in them which was connected to the wearers own nipples and pads that massage the flesh so it imitated what the wearer was feeling on the fake boobs it was expensive, they also had a very convincing gaff, but I could afford them, and I would order them the next day. I would also purchase a home waxing kit and make sure my body was smooth and hairless, yes my plans were all coming together and from the same place a make-up kit. This was something I desperately needed more practice with, I wanted it to look sexy and not to slutty so I secretly started to watch make-up tutorials on watch-it online, this also helped me with ideas for dressing up and for finding sex toys I could use.

One of these was titled a "big fuck machine" it came with two massive cocks one black and the other white, dimensions were big a whopping 300mm long and 75mm thick, and one more normal sized cock of 150mm long and 50mm thick. The machine was remote controlled came with a lockable belt that attached the user to the machine at either end and was released once the cycle chosen had finished the cycle was complete once it ejected the cum substitute either into your butt or mouth. It also came with a special ejaculating dildo and fake cum about 500mls. So, four dildo's total.

I clicked the link, and it took me to the web site "Sexual Pleasure" all desires and kinks catered for, from BDSM and back to BDSM we specialise in, toys, restraints, hoods, whips, clamps, chains, suspension gear, cages and machines. We also design and supply full fitted bespoke dungeons and play equipment from spanking benches to crosses. Catalogue available on request cost £25.00 or free if you spend over £500.00 on your first order. I ordered the catalogue and happily waited for it to arrive.

I was all set and eagerly awaited the end of the week all the items I had ordered would come on Saturday. So, both my wife and stepson would be out of the way, at work I could not concentrate which became worse towards Friday, so much so that I gave the staff a half day off so I could get home early, I had said my goodbyes that morning to both so I was confident that I would have the house to myself.

Saturday morning and I waited for the special deliveries and by midday I had my boobs, gaff and make up kit in my hands.

Now to start with a full week of being Kimberly.

To be continued.