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My dream is to spend the rest of my life in feminine attire...glamorous dresses of all kinds from luxurious silky smooth satins to sweet shiny PVC/Latex. But I must point out to you that I'm very inexperienced in more ways than one. I've been cross-dressing privately for some time but, for varying reasons over the years, have not taken many steps beyond this. One of these reasons is my complete lack of relationships. I've made many mistakes throughout my life, with a lack of understanding and confidence in social situations always hampering me. I've often thought that there were more important things to be doing, or that I'd rather be on my own and not have to always compromise. Despite often feeling lonely, there are still many social occasions where I'd rather be at home on my own. Don't get me wrong, I'm quite a self-assured person, at least on the outside...it's just on the inside where I'm more vulnerable.
I've long fantasised about living in a woman's shoes; since a very early age, I've envied a woman's entitlement to wear a wonderful array of clothes. Whilst at University, I started dressing more than ever and masturbating every day thinking about how good it would be to live as a pre-op or post-op transsexual. There were times when I could go without dressing, but it's never gone away. Since then, pretty much all I've had the courage to do is ogle at the internet and dream. I have however discovered more and more layers to my desires, in particular those that might facilitate or seem to go hand in hand with my feminisation. Perhaps I've been duped into the stereotypical objectification of the female form in all types of media, but I can't help what turns me on.
There's perhaps nothing more I've ever wanted to experience than life as a mellifluous and resourceful sissy for all occasions. But it's partially the belief I'll have to submit my will to another, in return for this opportunity, that's lead me to a fantasy such as this. I've come to desire this submission almost as much, as it's perhaps the opposite side of the same coin, and because I'm well aware that there may be times at which I'll be reluctant to continue. I fear I may not be strong enough to do this on my own...
My sissy fantasy is to be "permanently chaste to ensure the control of my own desires, and my obedience to my firm (but fair) Superior(s), release only coming via prostate milking incorporating Pavlovian conditioning. I'd always be ready to provide pleasure to my Dominant(s) through my mouth and anus and would humbly accept being cuckolded should my Dominant(s) require a proper Man, or Woman, to service them sexually.
"Although not keen on pain, I'd willingly accept that its threat and infliction is of vital importance to any training regime. My punishments would be vital in reinforcing my position in the household to exist simply for the comfort and pleasure of my Dominant(s), ensuring that I'm suitably moulded to meet Their exacting requirements. They would not spare me any necessary discipline or humiliation, whilst still ensuring that I felt loved, a part of Them, and needed."
Although I've never had a girlfriend, I'd say that I'm definitely not gay. What I am, most definitely, is bi-curious. I've always been attracted to women, but over time have come to desire the male sexual organs. Perhaps I'm again succumbing to the Internet's stereotype of a sissy, but the thought of servicing a man orally and/or anally just feels like the right thing for a sissy to do. But I'm not a sissy yet...and I may not be ready for any relationship in the near future, let alone one with a man.
To be honest, I don't know where to go from here. All I can say is that I have a very strong desire to become as feminine as I can, whether this simply be a part-time 'hobby' for the rest of my life, or the first step on a radical journey that will leave my time as a man as nothing but a distant and long forgotten memory. It's the driving force behind everything I say here and is probably the pre-requisite for anything else to happen. Beyond this though, it's mere conjecture. I've yet to experience any meaningful type of relationship; so what I think now, may not be what I think in two years time - I may completely change my mind on what it is I most desire...
+Perhaps I'll end up in a 'normal' vanilla relationship with an understanding woman who allows me to cross-dress on occasions?
+Perhaps I'll become the pre-op girlfriend/wife of a loving boyfriend/husband where there may be elements of a master/slave relationship, but not necessarily?
+Perhaps I'll go through a sex-change operation, become a women and live a 'normal' female life?
+Or perhaps I'll become the 24/7 live-in sissy maid to a firm, but fair, Master and Mistress??
As much as I'd like to be able to click my fingers and be in my ideal relationship, whatever that may turn out to be, I'm prepared to be patient. Living with my parents, currently being out of work and being very hairy, I'm going to have to be! I may well have to wait until I'm working and living on my own in order to properly fund my development.
In time I hope to meet, socialise and learn from people in and around Surrey/South London, and go on to experiment to discover what I really like, and what I really don't. I'd certainly like to be friends with someone in the real world before anything serious happens and only start my journey of feminisation when I think I'll be ready to do myself justice and hopefully become convincing...
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