First time 20.......


First(and last!)time…..



Musings from WannabeGinger


Sadly, dear Readers, my writings have lost their interest for many people and the number of hits received for my recent chapters have fallen and fallen. I must be boring everybody, which lowers the satisfaction I get from writing. So, reluctantly, I’m making this my Last Time of writing on the subject of First Times. Here are the firsts I would have written more about……..
Chapter 20

My first times……………

(not in chronological order…. Try to guess which came first, second, third…..

Wearing lipstick and freshening it up in the street, caring not who saw.

Having false eyelashes fitted.

Having my own eyelashes dyed.

Crying when I threw that wig away.

Having a fully-dressed “Awayday” at a Transformation store in Manchester, wearing my own underwear and staying over keeping the make-up until morning.

Buying a pair of black sling-back stiletto Heels (and hiding them carefully in the garage).

Buying a pair of silicone false tits (and having nowhere to hide them).

Being told by my wife that I would have to leave home if I was a Transvestite because she knew I would abuse our children if I was.

Wearing a nightdress in the bedroom.

Shaving my nipples and underarms.

Buying a full length corset with buttoned gusset that would allow me to have sex while wearing it.

Having highlights put into my hair in a salon where I might have been recognized.

Wearing lacy panties with my Wife’s ok.

Writing my first CD story and publishing it on Crystal’s Storysite.

Having a “Make-up and Change day”; Wearing full Transformation make-up, my own sky blue skirt and jacket, wig (the burgundy, bobbed-styled one), slingbacks, stockings, suspenders, bra and waist cincher.

Going out fully dressed after a “Make-up and Change day” returning to a budget hotel fully dressed.

Being stopped by a policeman for standing too long on a shop corner in Oxford Street while having a wank through my trousers.

Finding Big Closet/Top Shelf after Crystal’s Storysite “went technical”.

Talking with a Lesbian about making love to a woman.

Having girl-on-girl sex with a really beautiful so-called/self-styled “lipstick Lesbian”..

Finding my wrists in handcuffs that my Wife had bought as a surprise.

Having my hair pinned back and a half-head “fall” gripped into the back and dressed high with petal-like curls for a glam “turnabout” party.

Hiring a full length evening gown for the turnabout party.

Buying a leather collar, in case she wanted to tie me some more… which she did.

Buying a dildo and using it to give my wife pleasure she would learn to love and anticipate.

Having the dildo used on me by my Wife, for a one and only time.

Buying a strap-on dildo when my libido was at lowest ebb, but never using it.

Getting a prescription for Cialis.

Buying estrogen cream and rubbing it into my tits.

Removing my body hair with Nair.

Panicking when dressed on hearing my wife’s car arrive back earlier than expected.

Running to the shower to remove make-up and other evidence of my dressing when nearly discovered.

Remembering that I had not put away the wig where it belonged after using it.

Buying my own “barely enough” lipstick to wear all day.

Renting a corseted gown and high-piled curl wig for a (once only) Hallow’een Party.

Every time (is a first time) when I have purged my stash of clothes and cosmetics.

Renting a flat where I could hide all my dressing clothes, fetish wear and cosmetics, and decorating it in ultra-feminine colours and furnishings.

Refusing, for the first of not-so-many times, when a guy came on strong to me.

Dreaming of actually changing my gender, and then realizing that’s not what I want out of life.

Being thankful that, if my Wife accepts that I have given up my dressing compulsion, I can continue to live my dreams through my writings.

There you are, my darling readers. You may not believe these, but they all fit into a life after marriage of forty years.

No, no regrets!

Here is a story I published on Big Closet some time ago…. Which I hope you’ll read again…


Regrets, I've Had A Few


by WannabeGinger

But then again, too few to mention……… I don't think so!
Indeed, many crossdressers have lives filled with regrets. They/we have to console ourselves with the high spots, the wonderful interludes in which we indulge ourselves. Before we feel guilty, or before we hastily hide away things that will betray our desires.
We can't summon the courage to disclose our feelings to someone we love — wives, girlfriends, whoever…. Could they ever react positively? Not on your life! Worse still, we may throw the "baby out with the bathwater" at times, believing that we can do without indulgence of our feminine instincts.

We throw away the clothes we have kept hidden. We ditch the cosmetics that we struggle to learn how to apply with care. We even put a beautiful wig into the trash; the wig that finally transformed the image in our mirror and made us feel whole, or wholly female.
I've been there and done all of these things. More than once. And yet…… the impulse is still strong.

In the street, I admire women I see, usually for their striking and beautiful hair at first; then the facial features and how make-up highlights the best aspects for them. I admire their clothes, it's true, but only as part of the whole picture…. the illusion that I would hope to adopt, if they're "my type" of girl.

So what do I do? I buy more clothes, or at least underwear, of my own. I can wear my wife's clothes when she's not around (I'm lucky) and can buy her things I might fancy for myself. Then, what do I do, I chicken out and throw my things away again.

I read and write CD stories, living through them the fantasy that I can't bring into reality………….. The Big Closet is the best of them all, because Readers like you give feedback and comments happily, but it can't be logged onto my "favourites" for fear of discovery. I do enjoy a visit to a Transformation salon occasionally, when business travel permits or gives an excuse.

I call myself Karen when I'm dreaming, in memory of a client who was a wonderful (GG female) businesswoman with striking green eyes. She was tall but made the most of it; no fear of heights, she wore high heels that accentuated her shapely legs….. as I should do. She had a wonderful fall of highlighted blonde hair which I continuously dreamed of copying, if only my own hair would grow fast! We could have made music together.

Regrets, there's another. I read loads of stories that deal with TG and surgery, S&M and dominance, forced feminizations……… these aren't for me (though with my wife we have played such games for fun)……. I just wish… I just wish…. for gentle, understanding of the desire for a boy to be more like a girl, just now and again.

So, I keep my secrets "back in the box"… Pandora's not a lady I could live with. I tried to disclose all of this to my wife one time, but she hit the panic button! The limit I'm left with is to wear lipstick from time to time……… if it makes me feel better…….. Oh, so much more could be beautiful.

How can a wife be involved willingly?

………….But, through it all, when there were doubts, I wish I'd done it "my way".

... And most times, I did!

Be happy,
Love Ginger. xx



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