Real Life Transgender Stories
I was living at home with my parents, and sister Paula who is two years older than myself; tall, slim, dark haired and beautiful. With her being that little bit older, her body having filled out with womanly curves, we appeared to be about the same physical size, apart from the bumps that is.
I had always admired Paula, both as a sister and more lately as a woman, and for quite some time I had harboured ideas that I wanted to look like her, be like her, and horror of horrors, dress like her. In those days of the mid 1960’s cross dressing was virtually unheard of and one never saw a man dressed as a woman as we do nowadays.
We were not a particularly shy family and our parents were quite liberal in their attitudes towards sex, nudity, and life in general. When we had problems they were always available to talk them through, as was Paula, but still I dared not approach any of them with the sort of problem that had manifested itself in my mind, and which was growing daily.
Paula used to do her make up sat at the dressing table in her bedroom, usually clad just in her undies which varied as to what she was doing that day or evening. I used to sit on her bed and we’d chat like brother and sister do, but all the time I was watching what she wore and how she wore it, noting which type of make up she used and how she applied it, and wishing I could do the same. She nearly always wore stockings and suspenders, or hold up stockings as this was the time before the era of practical but non-sexy tights. That evening her outfit was all silky pink. She looked stunning, and she must have noticed me ogling her as I saw a smile on her face reflected in the dressing table mirror.
Trying to be nonchalant about the whole scene I tried to prise my eyes away and look elsewhere, but they always returned to Paula’s suspenders and panties, and her knowing smile in the mirror. I knew then that I could no longer resist the urge to try on some of her underwear and was determined that this would be the night, as Paula was seeing a new boyfriend and our parents were going to the theatre. I was to be alone for the whole evening.
An hour later they had all gone, leaving me with a “take care now” from our parents and a kiss on the cheek from Paula with the words, “Be a good boy Andy, won’t you ?”
Did she know then what I was planning ? The female sex were supposed to be perceptive I thought, but quickly dismissed the idea as the excitement in me grew. A whole evening alone with the chance to try on all my sister’s outfits was an opportunity not to be missed at any price!
I rushed upstairs into Paula’s room and stripped naked before the dressing table mirror, looking at my manliness and wondering why nature had chosen me to be male when I knew different, feeling sad just then as there was absolutely nothing I could do about it.
It seemed that Paula spent most of her money on undies as there were three draws full of panties, bras,stockings and suspender belts of different colours and materials, and a basque. All were neatly folded and I wondered if she knew precisely where they should all be. Probably not I thought, pulling out a nice white pair of silky French knickers and sliding them on.
Mmmm, this felt wonderful, the silky feel on my body just like the touch of feminine fingers caressing my loins. Next was a choice of suspenders, but I’d forgotten whether they went over or under the knickers, finally deciding on underneath them. Now for a bra. Picking one out to match was easy, but getting the thing hooked up was quite difficult and took some time and it looked somewhat silly, so I padded it out with some of Paula’s Pop socks.
Sitting there at her dressing table I began to make myself up with Paula’s kit. Starting at the top I applied mascara to the eyebrows and eyelashes, then a light blue to my eyelids, and some very deep red lipstick on my lips. Looking at the vision in the mirror it became apparent that there was an art to making up ones face which I sadly lacked, but the overall effect of wearing make up and sexy underwear was beginning to stir my senses and I noticed a growing bulge in an area where girls do not have bulges.
Not knowing when the opportunity to dress like this would present itself again I stripped off those undies and tried on some more. That wonderful evening passed on in this manner until I had tried on virtually every piece of little silky things that Paula possessed, the excitement mounting more and more with everything I took off and replaced with some other girlie garments, until I donned the last pair of panties, which seemed a little tighter than the rest, their tightness seeming to hold me like no others when I moved.
I decided further movement would end in disaster and so I stood still, arms across my breasts, looking deep into the mirror. Well, the inevitable happened as I knew it would and I had an “accident” in Paula’s favourite panties! When that was over I had to wash them clean, dry and iron them and replace them before Paula or our parents returned, and it was getting late by that time. Trouble was brewing.
How I managed to achieve all this, and replace Paula’s undie drawers in some semblance of the order they had been in previously I have no idea. Checking everything looked as it should be I exited her bedroom and switched off the light.
Nothing further happened next day, so Paula couldn’t have noticed my “raid” last night, and from there on I used to dress up quite often whenever possible without anyone else being the wiser.
About six months later, just when I had got the hang of cross dressing and all the feminine bits and pieces, was able now to fasten and unfasten a bra blindfold, clipping stockings to suspenders being easy now, Paula announced that she was to move out and have her own flat. She loved us all she said, but really needed to have a place of her own, and was to move the following weekend.
This was ghastly news, partly because I loved her as a sister, and partly because I would no longer be able to dress in her clothes.
The fateful day arrived and we all helped Paula to move out of our home and into her new flat about a mile away. I must have blushed as she handed me a draw full of her undies and asked me to carry them inside.
When she was finally installed and we others were about to depart Paula hugged me and said, “Thanks for your help Andy, and I’d like you to have this so you can visit me at any time.” She handed me an envelope which contained her door key. Perhaps there would be a chance for me to dress up sometime when she was out I thought, and then she said,”Why not come round next Friday night and stay the weekend, then we can chat like old times ?”
I replied this was fine, and our parents thought it was great that we were so close and not going to lose touch now she had moved out.
The next Friday evening I bathed, changed and walked down to Paula’s place with an overnight bag, letting myself in with her key.
“Hello Paula,” I shouted.
“I’m in the bedroom getting ready,” she shouted back, “come on in Andy.”
As per usual my beautiful sister was sat at her dressing table putting the finishing touches to her make up, and turning to me she said, “Andy love, I’m not daft you know. I know what you have been doing for these last six months. Want to talk about it?”
And all this time I had been under the impression she had not found me out, but she had known and kept quiet.
“Sorry Paula, but there was no other way. I couldn’t go out and buy clothes like yours, and even if I had been able to where would I keep them ? How did you find out?” I asked.
“Oh, about six months ago, just after we all went out that evening leaving you in the house alone,” she replied. Next day I was hunting for my favourite panties and found them at the bottom of the draw when they should have been near the top. And they were damp too. I never put my panties away damp. Did you have an accident or something?”
I explained quietly what had happened, and that at every chance I had been wearing her things. Paula was giving me one of those knowing smiles again and didn’t seem in the least bit angry or surprised. I told her that for some time I had had these feelings of being a woman trapped in a male body, and just wanted to be like her, lucky girl.
“Mmm, I suspected as much,” said Paula, “you’d make a lovely girl Andy. You’re so pretty as well. OK, l,ve been giving this situation some thought. You can come here and use the flat to dress up where no one else will know, and I’ll help you with make up and things. This is one of the reasons I wanted to move from home, though I wish you had asked me before raiding my clothes, it was a bit naughty you know. Take your clothes off Andy and let’s see what we can do.”
Though we had seen each other naked and semi naked many times before, here was my own sister telling me to take my clothes off in front of her! The very thought of Paula helping me in my quest made my heart jump for joy.
“Don’t be embarrassed Andy, we’ve both seen it all before,” said Paula.
Seconds later I had stripped, my clothes strewn on the floor and Paula was looking me up and down. The usual excitement was stirring in my loins.
“Just as I thought,” she said, “we’ll have to start with those hairy legs. I’ve got some hair removal cream. Looks like we’ll need a whole pot, but before we start can you please do something with that erection of yours. Remember I am your sister after all! Go into the bathroom and splash some cold water on it, that should do the trick.”
I tried to explain that it was caused not by lust for her, although she was very beautiful, but by the expectancy of her helping to make me into a woman like her, but I did as she said, returning soon in a more suitable state to stand before my sister.
She lay me down and depilated my legs up to the groin, scraping off the cream and hairs minutes later, leaving them smooth as her silky undies.
“I’ve been shopping for you,” she said, “come and look what we have here.”
Opening the wardrobe door Paula showed me a whole array of girlie clothes and a draw full of silky underwear. My mind was in a spin!
“Some of these are new, and some are my own, which you’ll no doubt recognise, but you may as well have them now Andy. But first, don’t you think we should call you by a more feminine name, even though you’ll always be my little brother Andy?” she went on.
“Anne. I’ve always thought of myself as Anne!” I replied, and from that moment on ‘Anne’ was born.
Paula passed me a new pink suspender belt just like her own and told me to put it on, then some fine mesh stockings on my new-look silky legs – no more hairs poking through the mesh from now on!
“You’d better put these on as well,” she continued, “you certainly seem to have put them to good use these last months,” and passed me those beautiful, sexy, silky French knickers of hers. “And now a bra Anne,” she went on, “use this one of mine till we know the right size.”
This was seventh heaven as Paula took my hand and led me to the dressing table chair, sitting me down, skillfully making up my face as I had watched her do to herself all those times.
“I used to watch you watching me do this,” she said, “It amused me at first, and puzzled me a little as I thought you might be turning into some sort of pervert just wanting to see his sister semi naked, then the penny dropped when you left my make up box in a mess one night and I suspected you were using it on yourself. This was long before I discovered you had been wearing my undies. It was quite a relief to find out that was all there was to it”
So she had know all this time! It was a huge relief to me as well!
Though I say it myself, I was quite a stunner when Paula finished the make up, probably due to her skill and the fact that we looked similar as well. All that was lacking in those days were proper breasts and a “dong” removal kit and I would have been a proper girl just like Paula.
Paula had great dress sense and insisted that first time in experimenting with the clothes she was dressing me in to see what suited best. First I was a lady in a long skirt, then a figure hugging evening gown, but my hips were the wrong shape to carry this off. Next I was a tart, wearing a creamy blouse with one of her own very short skirts which showed my suspenders if I so much as bent a little.
Soon it was late and time for bed. “I have a special present for you now Anne,” said Paula as she passed me a nicely wrapped parcel, which I soon undid and found to be a Baby Doll nightie and a pair of frilly panties!
I was in tears as I went into the spare bedroom that night with Paula’s last words of the evening ringing in my ears, “And no more accidents with those panties Anne, remember you don’t have to pretend any more.”
Eventually I moved in with Paula and with the use of wigs we were able to go out and about as two great looking girls out together, shopping, clubbing, being ogled and whistled at by the lads wherever we went. It was wonderful and lasted for just over two years, though I reverted to being a man for work and going out on my own.
But not every story has a happy ending, and this one is no exception to that rule, for I discovered that most girls in those days did not and would not accept a man who dressed in women’s clothes. As Paula was getting married soon I had to find somewhere else to live and there was also the matter of my adoration for another girl, Jean, whom I eventually married.
Thirty years later and still married to Jean I have had to supress these inner urges to dress as a woman, although they are as strong now as they ever were. Jean was and still is the light of my life and we have two wonderful grown up children, but she never accepted me dressed as a woman, though she lets me wear some silky undies now and then, and has even purchased them for me on occasion, but only in the house and only when no one else is there.
Paula still keeps some things for me locked away so that I may nip over to her place when the urges get too much to bear and she is on her own. We are still as close as ever, and our secret has been kept that way, a secret, even when Jean talked to her about my problem she never told her about the help she had given me in the past and which she continues to give me, though she did try to explain to Jean that there was no harm in a man dressing up.