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by deety
Rated: 13+ · Draft · Erotica · #2253797
A journey into crossdressing
It was an unseasonably cold Monday evening that Dai eventually built up his courage enough to step through the doors of the Fiona Lewis School of Dance. Painfully shy Stephen had few friends and none in this locality. It was the summer of 1960 and Dai had moved to Northampton after leaving his boys only Grammar School in Birmingham to continue his training as an accountant. It had been Steven’s mothers suggestion that he go to a dancing class as a way of meeting other young people and he was feeling alone and incredibly shy about trying to approach strangers.

This could quite easily have been a disaster as his mum's ideas on social interaction were many years out of date. Socially inept Stephen would have been the butt of humour and generally teasing in most ballroom dancing schools of that time. However, by sheer good fortune he had landed in one of the nicest schools which still maintained many of the old traditions. Standing nervously in the doorway Stephen was about to turn tail and run when Fiona came up to him and welcomed him. Used to the nervousness of young men, Fiona took him over to a quiet corner and explained the little bit about the school before introducing him to Barbara and Caroline, two of the girls in the class whom she thought he might get on with.

Leaving them to get acquainted Fiona was already quite worried about Steven. He really was quite abnormally shy, and was already blushing and stuttering as he spoke with the two pretty girls. However as time passed he seemed much more comfortable and was talking, not only to them, but to the other girls in their little gang. Satisfied for now, Fiona hoped but by the time the dancing class itself started he would be comfortable enough to accompany one of the girls onto the floor. To be honest she need not have worried too much, as Barbara and her friends had rather taken to this shy and gauche young man, he was so different from the rather brash, over confident men they normally saw here.

As the class proper started it soon became apparent that Steven’s shyness meant that there was no way he could approach and ask a girl to accompany him. Barbara, noticing this, took it upon herself to ask if he would like to dance with her. Accepting gratefully, Stephen was soon getting to grips with the basic steps of the waltz. At the end of this first dance, another of the girls invited him to dance with her. During that first evening Dai had met and danced, sort of, with not only Barbara, but also her friends Jane, Carolyn and Trixie.

Over the weeks of that summer Dai became an accepted part of the little group. The girls found his gentlemanly shyness very endearing and he in turn enjoyed, for the first time in his life, pleasant feminine company. He loved talking to the girls and in turn they loved talking to him, and rather enjoyed teasing him a little. If the truth be told Stephen was finding the company of these young ladies far more acceptable than the rather coarse company of those men had met at work. Conversation in pubs with other men seemed restricted to football and what Steven guessed were imagined sexual conquests. He much more enjoyed the time he spent with the girls and loved the way they gossiped about men and clothes.

Dai’s innocence was noticed by the girls who found it endearing but extraordinary. In time, however, they had come to understand the reasons. His mother had died in childbirth and he had been brought up by his father and a brother nine years his senior. He had attended an all boys Grammar School and had had really had no feminine influences on his life whatsoever. Concerned about this they had secretly discussed ways that could help and educate the hapless lad. It was his obvious delight in watching them when they danced the jive that caused the flash of inspiration.

The late 1950;s early 60’s were very much the heyday of the Rock and Roll years. Girls often wore very full skirts with stiff sugared petticoats and when they danced showed off many a pretty leg and even the occasional flash of stocking tops. They knew that Dai really enjoyed watching them dancing in such skirts and that had given them the idea.

It was an Autumn Saturday and they had been shopping dragging a somewhat reluctant Dai with them. Finding it amusing as they made a few purchases in the lingerie store how he hung about outside, pretending he wasn’t with them and wasn’t looking at what they were buying, and failing miserably at both.

They teased him about it, making him blush before they all descended on the newly opened coffee bar. Here, there was a jukebox, and they could listen to some of the latest music and enjoy a frothy coffee, so different to the ‘Camp’ coffee essence that was all you get otherwise. Sometimes, you could even get up and dance although there wasn’t much space between the tables. Carolyn and Trixie were dancing to Expresso Bongo when Carolyn’s skirt caught a cup on the table and sent (fortunately cool) frothy coffee all over poor Dai.

Spatters of milky coffee covered his shirt and trousers and really were quite a mess. Barbara quickly came to the rescue saying as her flat was just around the corner we could go back there. Once there, she should be able to sponge the worst of the mess off to allow me to get home. So rapidly the three girls and Dai left to hurry back to Barbara’s flat to reduce the damage. Reaching the safety of Barbara;s little flat, Dai quickly realised that there was a problem. Little More than a bedsit the flat comprised a small galley style kitchen and one larger room comprising a bed, a small table and two easy chairs. Obviously he would need to remove his shirt and quite possibly trousers to get them properly sponge to clean and he could hardly sit there in his underwear with the three girls.

He voiced his concern, but the girls who had planned this all along reassured him that it would all be quite safe and proper. Passing him a floral dressing gown Barbara told him to go into the toilet, take off his trousers and shirt and put the dressing gown on while she sorted things out.

Feeling somewhat foolish, Dai did what he was told. He gave Barbara the soiled trousers and shirt and self-consciously sat on the edge of the bed, Trixie and Caroline already being in the chairs. Barbara, having sponged off the trousers and actually washed the shirt, came back in and sat on the bed too. Conversation was difficult because it was very obvious and Dai was somewhat embarrassed being sat there in a woman's dressing gown.It was Trixie, the extrovert who broke the ice. Standing up, she said everyone was being ridiculously coy. There were only the four of us and we can be all girls together for now. Laughing, the others agreed, even Dai, who said he would be proud to be an honorary girl in such a company. On impulse Barbara kissed Dia on the cheek and welcomed him to the Fiona Lewis Girls Club. The other girls immediately did the same, confirming him as an honorary girl.

The ice broken, they started chatting freely once more, teasing Dia about his furtiveness outside the lingerie shop. They told him he was rather silly and his furtiveness made him more, rather than less visible. Just what was he so afraid of they questioned. He tried To explain that he wasn't afraid, just totally confused by all the stuff that he didn't know. How he loved how pretty They looked all dressed up but exactly what went where and why he had not the faintest idea.

That made them giggle and they said that he now had the perfect opportunity to find out more. After all, hadn’t they just said it was all girls together and welcomed him to the girls club. Was he going to spoil it by going all macho boyish?He was now one of the girls, and perhaps it was time that he learned exactly how a girl dressed. This made him blush even more furiously, and they giggled at his discomfort. Trixie, flicking her skirt up, and swishing out the starched frills of her petticoat, suggested he would look lovely dressed in the same. Barbara suggested how sexy he might feel , and how would he like to try a few girly things and truly be ‘one of the girls’. After rather more teasing, his curiosity aroused Dai agreed to try if they promised not to laugh or ever tell anyone else.

Suddenly he found he was the recipient of even more kisses and hugs, before the girls mysteriously sought out some extremely feminine frippery. Handing him a pair of satin knickers, Barbara told him to go out to the loo, undress completely, put on the knickers and dressing gown and then come back. A few minutes later, feeling remarkably foolish, he slid his legs into the slippery shiny panties and pulled them up. He was surprised how flimsy and light they seemed, but was pleased that they fit and that there was enough room to tuck everything neatly, if rather snugly, out of sight. He put the dressing gown over his shoulders and returned to sit meekly at the end of the bed.

Carolyn asked him how he felt and was he ready for the next stage. Barbara said we know that he liked stockings or or at least he seemed to like peeking at theirs. So they thought he would like to try some of his own and she handed him an unopened pack of nylons. As was usual at that time they were fully fashioned, seamed stockings. Ten denier and very very fragile, and because of that he needed their help in getting them on and getting the seam to run straight up his calf. He was beginning to rather enjoy all this attention. He suddenly came to realise that if he was to stand up that the stockings would just slip down his legs. Trixie told him he would need either to wear tight elastic garters or do what they did and wear a suspender belt. She lifted her skirt and underskirt to show him the one she was wearing. Commenting how nice it looked he was surprised when the other two girls also lifted their skirts to show that Barbara was wearing a ‘roll on’ and Carolyn a high waisted girdle. Barbara said that there were lots of possibilities and each has its uses, but in the proper circumstances each can make you feel very sexy and attractive. Dai was amazed, no wonder girls spent so much time shopping for lingerie when there were so many choices. The girls suggested he start with a suspender belt and helped him put on a belt that coordinated with his knickers. He nearly freaked out when Carolyn started poking the Garter Tabs into those knickers until it was explained that that way he could pull his knickers down to wee without needing to get half undressed.

So, there he was,wearing knickers and stockings, sitting on a bed with 3 lovely girls who seem to have decided to get undressed themselves as they stripped off their dresses and underskirts and sat back down wearing not much more than him, except they each had a beautiful bra, but of hugely different variety. They Wanted him to know the delightful variety that women enjoyed. Barbara was wearing a lacy full cup confection, obviously underwired and displaying her small breasts delightfully. Carolyn, who was quite a ‘busty’ young lady wore a balcony style again underwired to support her ample bosom. Finally Trixie showed how less was more. She had tiny little mounds more like fried eggs than breasts but a wonderfully cantilevered strapless bra left her looking fabulous and gave the impression of much more than she possessed. He was obviously delighted with what he could see and was easily persuaded into another elaborate confection like Trixie’s, but this one with straps that enabled the back of the bra to be much lower than on the girls bras. The reason for this would become obvious very quickly. He was delightfully surprised when the girls gathered him into their arms again, not only kissing him but pressing their naked flesh against his.

Now they handed Dai one of the wonderful stiff lace petticoats. Comprising many layers of sugared lace this stood out proud when standing but as he soon discovered had the propensity to rear up when sitting to expose legs, stockings and even knickers. The girls showed him how to control it and smooth it under himself as he sat. Once he had mastered this the girls all together said it was time for his frock and handed him a lovely blue dress. In a rich a velvet fabric dress was cut in approximation of the New Look Style with a 360 degree flared skirt under tight fitting bodice. The neckline was a modest vee at the front but the dress had virtually no back exposing and Dai’s shoulders. Looking and feeling extremely glamorous, Dai pirouetted, causing the hemline to rise as if he were dancing and exposing his legs and stocking tops.The girls clapped in delight and truthfully told him how feminine he looked.

Dai, now overwhelmed with new sensations, was quite obviously enjoying himself and when the girls asked if they could finish what they were doing he was in no position to resist. They set to work with a will, first attending to his makeup and then putting a blonde wig onto his head and brushing it out. Completing their transformation they invited him to take a look in the mirror and see what he thought.

Looking into that mirror Dai was amazed that there appeared to be no trace of him, just yet another gorgeous looking girl. Thanking the girls for the experience he commented it was such a shame that no one else could ever see have he could be transformed. The girls said they would be happy to transform him anytime he wanted but he would have to have a new name. For simplicity they suggested that why didn't he become Di, short for Diana rather than Dai short for Dafydd. After all they sounded almost the same and they could use it as a secret code to remind him of those moments when they helped him embrace his femininity. In any event, the day wasn’t over yet and his own clothes were still drying, why didn’t they go out together for a while as four girls DI was by no means sure about this but the girls convinced him that there was no way he would or could be recognised. Eventually he agreed and handed a cardigan and a handbag he left the safety of the flat in the company of his three friends.

Once outside he was amazed by all the new sensations from walking in heels, to the breeze blowing gently up his skirted legs. The gentle tugging of his suspenders against his stockings and the slight constriction of the bra strap constantly reminded him of how he was dressed. Feeling exposed he was grateful that Barbara and Trixie chose to link arms with him as all four walked arm in arm around the still busy town centre. Suddenly he realised that they had brought him back to the lingerie shop where he had become so embarrassed earlier. This time there was no escape and he was embroiled in looking through the dainty garments with his girlfriends.

Trixie had found a pretty pink elasticated rollon which she showed Di. Telling her she would look good in it she dared her to not only go and buy it but also to ask if they had any bras to match it. Feeling both extremely bold DI accepted the challenge and was soon being directed to a display nearby. The motherly lady who owned the shop was soon extolling the virtues of various garments and hapless DI suddenly discovered she had bought the girdle, a matching bra and three pairs of matching panties. Paying with a bemused look on her face the ex-boy left the shop clutching his carrier bag of purchases wondering why on earth he had done that.

If you like this story and think it has any merit please tell me and I will try a bit more.
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