First time…..

Musings from WannabeGinger

My first (and only) steady girlfriend hit me in my mid-teens. 17, I was, 15, she was!! This was the Sixties….. But everything wasn’t THAT relaxed! (…not where I was living at least). So I wasn’t yet ready to go out en femme as they call it. Girlfriend time was weekend time, so weekdays were the only possibilities for dressing…..

Chapter 16

I had been to M&S and bought that blouse — my first — and was sitting on my bed after Mum’s arrival, dreaming of going out en femme, but knowing I wouldn’t dare… not yet… perhaps when I went to Uni.

No, I had my stash of clothes that was getting bigger…. There was the blouse had helped create a look that was “me”, used with a pleated skirt that was my Mum’s — it was the only one that fitted me around the waist and was the right length. All the rest of her clothes were beyond my use.

I couldn’t risk dressing while she was in the house…. Personal space had meaning in those days but was regularly invaded — especially by Brothers but also, occasionally, by Mothers.

So the new blouse was added to my stash, unworn, but cherished..

I needed some nightwear. That would be ok; nobody would come in my room at night……

Another week’s wages would soon be invested. I lay awake at nights, dreaming of going in and selecting the most wonderful silky, satiny, full-length nightdress that was ever designed. It could be a present for someone…….. It would have been wonderful…. To come home and wait for dark… and to slip into it for the whole of a night… and to wake with its silken folds caressing my arms and legs, and yes, maybe my chest. I wished I had tits. Fully-functional, erectile tits…. One’s that stood up and took notice if they were tweaked, or nibbled, or scratched, or caressed by the folds of a …… There I go, dreaming again. Round in circles……

So, yes, I did go out and buy that nightdress. It was easy. Too many to choose from, that was the enjoyable part, but all affordable (if you didn’t spend too much on beer like most teenaged boys)

I was approaching my 18th birthday when — for the very first time — I slept that way. And nobody knew. Nobody at all. It was easy……. I dreamed that I was Marilyn Monroe, or some other movie star…. Julie Christie was a favourite. Doctor Zhivago was a stunning film. I took my girlfriend to see that one……. Fabulous!

My weekends were spent with friends, and this one girl in particular. Not a stunner, but very attractive to me at the age I was…. It seemed easy; we made good friends and enjoyed eachother’s company.

We weren’t good enough friends for me to confide my secret though. But we soon became good enough friends for sex in the back of the car. Yes — there…. Well, nowhere else to go!

Parents were not THAT understanding — certainly hers were not!

Of course, I never wore a shred of anything from my feminine stash of clothes at the weekends.

Opportunities for dressing were becoming fewer and further between. Examination preparations, socializing and family intrigues, all conspired to cut my dressing off nearly totally. For the next year, until I went to Uni, I was confined to dressing in nightwear before going to bed. I laughed out loud some nights… imagining what would happen if the house caught fire and I was forced to evacuate the building…… in my nightie!

Thankfully, that never happened. But I did come perilously close to being discovered because I left my bedroom curtains open one night and stupidly undressed in the full light of the bedroom window. Whether I was seen, I never knew and, to this day, can’t speculate what would have happened if I had been.

I dressed less and less. Was I ashamed? Well, to tell the truth, I may well have become so. Not consciously, but remarkably. Like any crossdresser, the last thing imaginable was to have my parents to discover me dressed. Nor would I have been able to explain myself to my girlfriend of, now, several months’ standing.

University beckoned. I looked forward to greater freedom. Meanwhile, normality took over. “Things” took their natural course and we found ways for sex to be enjoyed in less extreme situations. As might be expected for someone with a “remote” Father, there had been little sex education in my life. Thus, those first experiences were fumblings that led to quite inadequate conclusions. I would cum too soon. She might not cum at all. And yet, she couldn’t say what she wanted me to do to make it all much better for her. Or so I could tell. I wanted so much to please her that I tried too hard… and so lost it at critical moments. All of which made me feel quite inadequate.

Then something really curious happened. It led to my becoming much more of a “successful performer” which is a term I literally hate…….. Sex shouldn’t be a performance. It should be shared joy. But, having “performed” so poorly in our early love-making, I found I was able to “perform” much more energetically, and reliably, if I used my imagination. Not to imagine I was making love to Marilyn, as many of my mates would have been doing. No Siree! I performed better if I imagined I WAS Marilyn….. Marilyn making love to another woman.

It was then that I discovered the joys that have sustained me through forty years of love-making; oral sex became the mainstay of my pleasure, and my pleasure giving. Recollections of the first "going down" on my girlfriend are very hazy. I know I wasn't forced. I know I felt I wanted to do this. I know it was a natural way to give greater pleasure to a girl. I imagined a girl "going down" on me so many times, it was second nature when I finally did so. To great effect. She surprised herself, finding an intensity of orgasm that neither of us admitted later we thought possible. She couldn't wait for more.... and I, for my own satisfaction, couldn't wait to give her more!

And there began one of my continuing fantasies that, in many variations, have lasted for forty years. And so, back to my theme of First times ….for everything.

--oo00oo–

Aged 18, with a girlfriend aged 16, ready that summer to go off to Uni., my life was about to change for ever. I would no longer be living at home. I would be in student culture, subject to student temptations, just like any other guy. (Except I had my own special temptations to face).

I had to plan how I would keep my stash of clothes a secret — either if I took it all to student halls of residence, or if I left it at home where it might be found in one of Mum’s “clear-outs2 that she did from time to time. After all, if I were not living there, she might decide to clear my room of much of the stuff I had accumulated as a teenager. What a surprise she might have if she did.

My clothing store was buried deep in the back of the closet where the sun never shone! I had everything by now. From underwear, to night wear, to blouses, but as yet, no skirts or dresses. The nearest I cam to a flowing skirt was a pair of flowing flared trousers that Mum had discarded as being very passé… the wrong style, the wrong colours….. What the hell, they were feminine and they fitted! Well, with the adjustable waist they did.

With them I could make a passable female from head to toe!

Except for shoes…… increasingly, I wanted a selection (yeah!) of shoes to choose from when I could dress……. So infrequently did I do so, the cost of shoes was prohibitive (and remember, this is in the days before charity stores had plenty to offer from the discards of beautiful ladies!)

Shoes were a problem; I was now larger in my feet than Mum ever was or would be. A size 7 (UK) was already on the large size for any women’s selection and that’s what I needed. Mum was a size 5 so, when aged 14, they were great fun.

So, reluctantly… oh, so reluctantly, I took the decision to leave my stash of clothes… stashed away in my room at home; sans a skirt and sans shoes. I would put my crossdressing on a shelf in the back of the closet where it belonged. I would risk discovery in one of Mm’s ‘clear-outs’ and I would be “normal”.

For the first time in my life, I had a purge! Not to the extent of throwing everything away, but at least in terms of denying myself access to the clothes I loved so much. I even decided to leave the nightwear and the panties and bras behind. My crossdressing migrated into my psyche; into my dreams and fantasies, always when alone. When having sex, I would be “normal”; I would concentrate on my girlfriend — or the occasional one-nighter at college dance nights.

I couldn’t resist taking a couple of my favourite lipsticks away to college with me. For security and comfort only, you understand — not for wearing ‘out’. The rest of my make-up went with the clothing. Into the closet you go!

That left my hair.

My alter ego had wonderful hair that I could only imagine emulating….. But it had grown. Beautifully. To beyond the length I ever imagined. By the time I went to college in the September of that year, it lay on my shoulders. What passed for a style was much as before — a central parting with a fringe and bangs to the sides, a crown that could be back-combed and ends that could be flipped at the toss of a curler! Poorly cut, I had to admit. But it had potential. Poor condition, maybe, but that’s easily fixed….. I needed to get it cut before going away. It needed to be male enough for everyday, but female enough for solo self-indulgence sometimes.

Luckily, this was a time for experimentation. With colour. Loads of guys and girls were now turning up with their hair coloured differently. I hadn’t dared, but felt increasingly left behind. It could be done with ease. But I lacked the courage to have it done in a salon, which I should have adored to do. No, for me, it was a trip to the multiple chemists, Boots, in the High Street near home.

Their hair colouring display had always been magnetic; drawing me in and urging me to buy. At last, for the first time, I gave in and made my purchase.

Nothing too drastic. Nothing permanent. Nothing to go lighter. No bleach!

A temporary rinse in Burgundy! I took my time, studying the alternatives. Caring not who looked

Chapter 17 follows.