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Anne's Story
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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!

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.



 

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