Chapter One. The beginning.
The front door opened, in response to my mother’s insistent bell ringing, and she greeted her friend saying ‘Hello Mary. I’m so sorry to trouble you but this young lady was lost and late for her date with Brian, so I brought her around.’ ‘Thanks Jo’ a puzzled Mary replied, whilst looking me up and down, ‘Brian’s having his tea at the moment but who shall I say wants him?’ ‘Emma’ I quietly responded.
Mary departed to return shortly with Brian, at which stage my nerve broke! Turning quickly I departed as fast as I could, with the sound of clicking heels and a rustle of silk around my legs, not daring to look back however much they called out. I needed to get home but couldn’t run without attracting even more attention; besides, high heels and a tight skirt are not ideal for running in!
‘So what?’ you might say. Well at fourteen I was dressed as a woman for the first time, and out tripping around the village to see my best friend who certainly had no a date with me! I’ll explain how this all occurred.
As the eldest son in the family I would join in make believe games that my sister and brothers played to while away the hours. One game we called ‘happy families’, which entailed wearing clothing (over our underwear), retrieved from the wardrobe mum used to store clothes awaiting repair or cascading to a growing generation. This particular evening my sister and I dressed as ‘mother and son’, she in my old school uniform whilst I wore one of mum’s old dresses and a pair of high-heeled shoes. Parading as usual for parental reaction and the customary howls of laughter, the sight produced a twinkle to mum’s eyes.
Later, when alone with mum talking about the earlier fun, she suggested I surprised my best friend Brian by playing a similar joke on him. Whilst not sure what she had in mind, I agreed not realising that she was quite serious.
‘Good’ she said ‘but we need suitable fitting clothes if we are to do this properly. I’ll see what I can find and then come up to my room when I call you’.
The call finally came and I was amazed at the variety of clothing items spread about her bed. Her clothing! She explained that the plan was for me to trick Brian into thinking I was a woman. Naturally I objected, but gently the challenge, thrill and potential risk of exposure persuaded me to change my mind.
Fortunately clothing selection was made easier as mum and I were of similar height. A green and cream checked skirt with long sleeved creamy silk blouse was first selected. A pair of white panties, girdle, long line bra and a full-length underskirt followed, together with seamed nylons and brown high-heeled shoes to complete the attire.
‘Right, time for a quick bath before changing’ mum instructed ‘I have added some scented bath salts to the water, so give yourself a good scrub including under your fingernails and come back here with a towel around you so we can start your transformation’.
Returning, task completed, mum shaped my eyebrows and manicured my fingernails before supervising my getting dressed. Sliding into the tight panties to hide my manhood, the girdle followed and its laces were gradually drawn tightly to bring a feminine shape to my body. The bra completed the outline after each cup had been filled with cotton wool to give me a pair of small but pert breasts. The underskirt followed, with Mum then demonstrating how to carefully roll nylons to avoid snags or ladders before I undertook the task. Finally managing to clip each onto the suspenders, I enjoyed the new elegance and pleasurable sensation the material brought to my legs as I walked.
The metamorphis continued with a light skin lotion and powder make up being applied to my face. Carefully applied soft brown shadow tint, eyeliner and mascara then accentuated my eyes. A dab of cheek blusher and two coats of pale brown lipstick completed the picture, whereupon my hair was brushed and elegantly restyled and a pair of pearl earrings fitted. Finally putting on the blouse and skirt, the latter encasing my body as its buttons fastened up the back, I stepped into the high-heeled shoes- almost falling over in the process.
‘Hmm. Some deportment practice is required before we go out’ mum said ‘meanwhile have a good look at yourself in the mirror!’ The sight of the younger version of my mother staring back at me from the full-length mirror was most electrifying. ‘Turn around and see how you look from each angle’ she said ‘and stop slouching. Stand tall, with your head up and chest out’.
Spending many minutes admiring my new look I couldn’t help thanking mum. ‘Its brilliant. I just can’t believe the change’ I said, not adding how much I enjoyed the growing feelings from within. ‘My new daughter does look better than I could have imagined’ she replied ‘but you really must practice your deportment and walking in heels. You don’t want a broken leg do you?’ Whilst helping tidy up, she instructed and I practised until I gained sufficient confidence for her to decide that it was time to depart before it got too late.
Donning a short coat and scarf we left for Brian’s house, walking arms linked until my confidence increased in my new female role. Just before arriving at Brian’s I realised that I didn’t know what to say or do, but Mum told me to relax as she had everything planned. So we arrived and —-well you know what happened next.
Chapter Two. Developments.
Waiting back at home for mum’s return, I feared what Brian and his mum might have said or done. How could I ever face them again, but apparently neither had recognised me, mum having feigning surprise at the incident, but disappointed that the jape hadn’t gone further.
‘Never mind, there is time to develop your female role’ she said. ‘Some serious training will reduce risk of recognition and expand your skills so that the jape will then ensure its victim doesn’t realise what happened’ ‘But I thought we had finished?’ ‘Not buy a long chalk’ she replied ‘I want one hundred percent effort from now on, otherwise I shall let Brian and your friends know what you have been up to’. Trapped, you bet – but enjoying every minute of being dressed as I was.
So the next few weeks started, albeit with a few ups and downs. Other family members didn’t realise what was happening, but I nearly got caught one night dad arrived home earlier than expected, and my sister almost caught me changing one evening because I had forgotten to lock the bedroom door.
Evenings spent baby-sitting saw me exploring mum’s wardrobe, trying on different skirts, dresses, blouses and underwear. I remember wearing a black strapless bra and matching cami-knickers under a soft cotton skirt and stiff petticoat, failing to create the convincing illusion of full breasts peaking from a gypsy style blouse. Day’s later mum produced the same clothing for me to wear, with an extra petticoat to correct my deportment, saying that she ‘might as well see how my choice was going, as I had so obviously enjoyed wearing them the other evening’. So much me thinking I had carefully put everything away, but she accepted that I needed to experiment to develop my female side.
The following Friday mum advised that as ‘it was the usual evening young people dressed to go out and I should therefore enter into the spirit of the day. She had bought me some new things to wear that were on my bed and I couldn’t wait to get changed into the new lingerie and a long sleeved floral dress. Mum helped me pull the dress fabric close around my waist and fastening the buttons up the back, trapping me in the dress in the process, before producing the ‘piece de resistance’. A shoulder length blond wig, which she combed and arranged on my head to change my appearance yet again before fitting a dangling gold earring to each ear. Nails suitably varnished to match lip colour I stepped into the pair of black high-heeled shoes to complete the picture.
After checking my appearance we returned to the lounge, reading and talking together in front of the fire until 15 minutes later mum rose to answer the doorbell. Before I knew what was happening, she had brought our visitor into the room-Brian! Fortunately I recovered sufficiently to stand up and welcome him.
‘Brian let me introduce my niece Emma. She has been visiting us for a couple of days’ mum said. ‘Emma, look after Brian for a few minutes whilst I go and find Mike?
How could I refuse, as she had left the room before I could answer? After an awkward moment I invited him to sit opposite, noticing that he was smartly dressed. It emerged mum had asked him earlier if he wanted to go with Mike to see the new film at the cinema, as she had got some tickets. He had now come to pick him up, little realising that Mike would not make it, as he was now Emma!
Mum returned saying that Mike couldn’t be found. It would be a pity to miss the film, so why not take me instead! Before I knew what was happening, Brian had agreed and I was being bundled out of the house. ‘Don’t be late dear.’ mum said triumphantly ‘Be back for 10 o’clock. Remember you have to be up early in the morning and need your sleep!’ Give me a light kiss on the cheek she whispered quietly, ‘Good luck, be careful and remember what you have learnt.’ So the jape was on!
The walk to the cinema was uneventful, the film well attended and Brian’s friends chose to sit away from us with their respective girl friends. During the film I felt a hand resting on my knee, but having moved it once or twice I let it rest until a scary scene when Brian’s ‘comforting arm’ slid around my shoulder- remaining there for the rest of the film. Whilst returning home we talked over the film until I put the key in the front door lock. Turning to thank Brian for the evening, he confidently grabbed me around the waist, pressed me against the wall and started to kiss me. I could feel his excitement and pressure of aroused manhood through my dress, but rescue was at hand when the hall lights went on and mum called out ‘Is that you Emma?’ Brian let go and whilst running away he quickly turned to give a cheery ‘Thanks and goodnight’ before disappearing-albeit leaving me slightly dishevelled.
Mum outlined her plans, including care of my new clothes and the need to wash underwear each night ready for the new day. I would wear my new underwear daily under my normal clothes, but when alone I would be fully dressed and made up, so that she could assess my progress. Daily training included deportment, manners, use of voice etc., as I assisted her in practical tasks around the house, including cooking, cleaning and babysitting. Overnight I would abandon pyjamas for a nightdress, matching briefs and padded bra, ensuring my female role developed as I gained my rounded education!
I described to mum how the evening had gone whilst getting undressed into my nightwear and she was well pleased with the result. I was less sure however. Whilst I had enjoyed being treated as a woman and would always remember my first kiss, I doubted that Brian would feel the same way if he ever found out. Inevitably I would hear his version of the events, which naturally varied from mine. As for Emma, who knew what had fate had yet in store for her, but her clothes were returned to mums wardrobe, apart from the nightgown, bra and pants which I was permitted to wear for just one more night.
Chapter Three. A surprise bath!
Next morning I arose early to go fishing with my father in the Lake District. Meeting my uncle by the river, which was close to flooding, we ‘tackled up’ and dispersed to ‘try our luck!’ To this day I don’t understand what happened to me, for one moment I was fishing from the bank and the next swimming for my life. Despite being swept swiftly down stream I managed to reach the bank and scrabble out of the water, completely sodden and shivering, to trudge miserably back to the car knowing that Dad would be none to pleased. His days fishing was ruined and he faced the prospect of returning home so soon after arrival. My uncle came to the rescue suggesting we returned to his house so I could dry out. He would see what he could find for me to wear, and then he and dad could resume fishing for the rest of the day. So fate took charge!
Upon reaching his house, my uncle and aunt could only find some of my cousin’s gym gear for me to wear – a white short-sleeved cotton blouse, blue gym knickers, short dark skirt, white ankle socks and a pair of plimsolls that she had recently grown out of. Obviously an awkward situation, but I really had no choice but to accept as I stood shivering and dripping in front of a roaring fire. Stripping off in a bedroom and towelling dry, I quickly put on the new clothes, handing my aunt the sodden garments to dry in front of the fire. Unbeknowingly in towelling my hair dry it had bushed out it into a more feminine style, but my aunt chose to ignore my appearance and dad and uncle had returned to their fishing.
Cousin Jayne eventually returned from school and, after getting over a fit of giggling at my misfortune, we adjourned to her room to play with a jigsaw. Casually the conversation turned to what I was wearing and she thought that her clothes suited me, although the skirt seemed a little too tight. Would it not be better if I wore one of her old panty girdles and a bra, so that I became more comfortable and the clothes would hang better? In view of my recent experiences I found myself agreeing and within a few minute had change into the selected underwear. Returned to check that all was in order, she commented on the improvement and that the bra was not really noticeable. Brushing a few knots out of my hair she rummaged in her make up bag and produced a pale lipstick. Stopping momentarily to test my reaction, she sensed nothing adverse and proceeded to give each lip a light coat, whereupon we both left to play outside for a while.
Eventually meeting one of her girl friends (who accepted me at face value when Jayne introduced me simply as ‘her cousin’) I was asked my name. ‘Erm’ I said thinking how to explain, but Jayne surprisingly said that I was Emma. So we whiled away a very pleasant afternoon, chatting and walking around the village until teatime when dad and my uncle returned. They were too full of fishing to notice any changes in my appearance, apart from dad commenting that ‘it served me right to be dressed as I was’ clearly thinking it was some kind of punishment!
Returning home later, having travelled in the clothes I had been given as my own were still too wet to wear, mum’s reaction on arrival home was one very much of surprise- Mikes departed and Emma returned. In explaining the circumstances she had to smile, whispering that ‘such is life. Your training obviously stood you in good stead. What more will the future bring?’ Next morning I awoke to find Emma’s clothes had returned to my wardrobe and so my future continued to develop. Life still had plenty of surprises in store for me, not all pleasant.