Freedom? What to do with a large lottery win.

So, I returned to the world of being a single man. A liberation of sorts, a return to uncertainty at a certain age. It is a scary place to be, ejected from the family home and to set up again.

Sure I have the comforts. Sure, I have all my books, the CD’s, plenty of DVDs. Ok, the furniture in the new place isn’t that good yet and I could do with a new mattress, but hey, a few weeks and that will be put right. I can get on and decorate the new place enjoy the anonymity of being in a new area and able to start afresh.

It is good that I have a great deal of money and can set up a snug new place back in the style I had so often wanted during the years before marriage and put it all on ice. My nice country farm would become the home for me and my alter ego. I was going to start ‘dressing’ again, enjoying my private world again and loving the feel of feminine clothing be it of woven cloth or nicely formed bespoke rubber wear - in fairness the rubber was by far the preferable.

My main question at first was whether I could shift my middle-aged weight? Could I lose my extra chin? Would I be able to once more get the hang of makeup and heels? No doubt; my thinning hair would not look good any longer, I’d have to look into wigs and all that laborious ‘extra’ care women take for granted but men find to be a pain in the posterior! Thank God I’m not hairy anyway.

So I brought some weights, some good trainers and miles of country lanes to run myself ragged over. I always enjoyed running well into my middle age. I delighted when lycra running tights became fashionable for the general fitness freak. I wasn’t ever a fitness freak, by the way, I just liked the tight figure-hugging lycra.

The intent was then to lose a lot of weight steadily, not wishing to make myself poorly by taking a bull in a china shop approach. If I was going to get a good male figure back and then develop a semblance of a female shape, I needed to shrug off thirty years of being a married man and all the male role model baggage one has to endure when really you crave to wear your wife’s heels and party gear. I knew it was all going to go wrong when she started wearing heels again to work. She never wore them to please me.

This new-found freedom was my downfall, whilst at work that glamorous woman allowed herself to stray, leading now to my singleness. At a late stage in life, she’d re-discovered a libido, denied to me for twenty years. She wanted him though, not me. So we became amicably parted, she moved in with him, alienated our son. I moved away. She wanted another man's dick and evidently was getting it. I wasn’t included in her desire any longer and that was pretty final. She still looked stunning, only the show wasn’t for me.

So rather than be a cuck and a snivelling weakling to boot, I decided it was best to re-start and just retire as a kind of ‘widower.’ Sure I’ve got millions and that is a comfort. As we just saw though, the freedom that cash gave my wife, gave her the freedom to say goodbye. She stayed in town with him.

I moved seventy miles back to the country and a beautiful farm and elected to live out my new life how I wanted to live it. I’ve written a book, it’s not about me, its a novel about the lead up to World War Two. Any proceeds to go to my son’s account. He doesn’t like what I do in my private life so I don’t shove it in his face, hence not wishing to be anything other than an occasional Tranny as and when I feel like it. In fairness that is much of the time.

Would I seek another partner then? Would it be a man or a woman? Perhaps it would be one of each, perhaps they would bring friends? The options are endless in a fantasy world. So I’ve joined kinky web groups and made contact with others in a similar position. The internet is a fantastic way to meet people and throw ideas about. After many years of not dating or being involved in seduction it seems weird to be tramping over old ground, and being ultra-cautious about people let into my new life. I do not want to be taken for a ride and I don’t want pity.

Having money, of course, helps. It means I can go shopping at the specialised retail shops, I can get nice heels made which fit properly, I can buy latex again, I can start to dabble in makeup and grow my nails , maybe I could have a quiet word with some makeup artists and get them to become my beautician and skincare experts. Do I look into surgery to remove my lower ribs, do I want to form that female form badly enough? Do I have liposuction, get rid of the unwanted stuff quickly - would that make me poorly? Do I really think I'll look anything else than a late-middle-aged bad drag act?

The sky is the limit with vanity to does go against the grain after a life of watching someone else steal the limelight and physical appreciation. I was just the dowdy bloke married to the glamorous Joan. I’d love some high heeled clogs, some high heels mules, thigh boots, court shoes, wedge espadrilles. I don’t really want drag artist tarty. If I’m going to be ‘dressed’ I'm going to be stylish even if I have a face which betrays my very real maleness. When I'm pleasing myself, I don’t care. If I acquire a kindred spirit, be they male or female, all the better.

I'm going to instal a steam room and sauna, a small multi-gym, and have taken advice on diet, cut down the drinking and looked into way and means of ‘feminising’ myself in a subtle way. In no way do I wish to trans. I don’t want boobs, I don’t want to lose my cock, I don’t want to lose my sex drive. I wish to enjoy having an open mind on matters sexual once again and indulge myself. I wish to dress as I please. I do not wish to have a miserable lonely life into old age.

Now times have changed so, being a wee bit “on the wild side” is no longer so strange or dangerous. Indeed it has become a fashion. I feel free to enjoy myself and I Intend to indulge it. I don’t wish particularly to be involved with the standard gay scene and will quite happily visit the capital to re-immerse myself on the fetish scene. However, I do not wish to be the lonely single man so oft seen at such events and royally fleeced for the privilege of being allowed to attend such events. Thankfully I have the budget to ‘hire’ a glamorous escort, all being well if ‘she’ was a convincing “shemale.” All the better. If a genuine companion can not be found; hired help to gain a happy entré would be good.

So am I to re-awaken old contacts and fellow kinksters? Are they where they used to be, are they still alive? If so how active are they? Can I break into a much younger and beautiful set? Would even the men look at me with anything other contemptuous pity whilst spending as much of my sugar daddy money? Would any genuine woman look at me, would I fancy them would they tolerate my crossdressing and total ‘unconvincing’ appearance as I gradually organise my return to being slim? I can’t say slim and lovely, as we all know age takes its toll. It was nice to get rid of my body hair. The next thing is to sort out my nails, both feet and hands and get back into taking care of my grooming. Something I hadn’t really done a great lot of in all those years of having close-cropped partially shaven head  When you haven’t got anything to brush... You don’t need a lot of grooming. 

I do laugh at myself, sitting in the lounge watching the Rugby Six Nations, a glass of beer, latex catsuit, anal bung firmly lodged, towering heels crap makeup… How incongruous loving watching and playing all my life one of the most “butch” games on the planet. Whilst really being a bit of a sissy under the veneer. The ability to laugh at my own foibles and desires ranks very highly. I’d never pass as a woman in a million years, I’m not sure I really want to.

More to follow as my adventure develops.

Ifonlyitwereme  - well maybe it will be!