Copyright - Lorna Elizabeth Black 2000

None of this work may be distributed as original by any other person or group. Permission is given to redistribute this work in its entirety and any credit is given to me as the original author.

Any resemblance between characters in this work and persons living or dead is purely coincidental.

Be also advised, some of the storylines contain adult themes including sex. If you are underage or if this offends, then please go elsewhere.

 

Joanne

by

Lorna Elizabeth Black

 

A very shy man meets an equally shy woman. Slowly they get to know each other and as their relationship begins to blossom, a cure is found for his shyness.

 

Chapter 1

 

Meeting

 

John and Jenny were two people that were very much alike. They were the same age, about the same height and had similar temperaments. In fact you could say they were the ideal couple but there was only one thing, neither knew each other. As well as that, both were single, and extremely shy, or so that was how the world perceived them. Although they had never met, things were about to change because there were other people with plans for them to do just that.

 

Now it was late summer and it was Mark and Susie's wedding, Mark knew John and Susie knew Jenny and between them they decided to manipulate events so that John and Jenny could meet. As far as Mark and Susie were concerned, they looked ideal for each other, and they thought if they could just meet, then events would take their own course. So for the wedding reception meal, the table plan was made so that John and Jenny would be sitting next to each other.

 

At the wedding reception, John was indeed sitting next to Jenny and apart from the usual niceties; there were long periods of painful silences. John did want to speak to Jenny and vice versa but their shyness seemed to be to the fore. Actually they did find each other mutually attractive but words between them were few and far. It was not until after the meal was over and the dancing started, the now married couple made sure that they stayed together and after a lot of cajoling, John and Jenny eventually had a dance together. It was really at this point they began to communicate with each other a bit better, realising they actually had much in common.

 

They danced more that evening, they were now beginning to relax in each other's company and whether it was the drink that had something to do with it, the plan that Mark and Susie had hatched seemed now to be working.

 

As the evening drew to a close, it seemed right that John escort Jenny home. In the taxi, they didn't say very much until they arrived at Jenny's flat. On the doorstep, John was about to turn and head for home when Jenny said,

"Would you like to come in for coffee?"

John hesitated for a bit and replied,

"I had better not. It's getting late."

"But I was going to give you that book we talked about earlier," Jenny said.

"If you're sure it's all right."

John followed Jenny inside, his shyness was coming back because gone were all the other people around where John felt safer. Jenny showed him into the lounge and asked him to sit down while she made coffee.

 

For the rest of the time, John did not say much, again his shyness dominating all his actions. It was Jenny who really made any of the moves. It was her who led the little conversation between them and it was her that suggested they meet up again. John agreed to this because to him, he seemed he had found a female companion but in reality had no idea on how to handle any relationship.

 

John left Jenny's flat only about half an hour after he had first entered there and made his way back to his own place, on foot, some two miles away.

 

Chapter 2

 

And Again

 

Almost as soon as John got in the door of his flat, the telephone rang. It was Jenny. She had decided to move things along by asking John round to her flat the next day. John was flattered and delighted and accepted in a stuttering voice.

 

John turned up at Jenny's flat at the pre-arranged time. He rang the doorbell; Jenny opened the door and answered,

"Come in."

There was one thing that John noticed immediately about Jenny was that she looked so different from the time they had first met at the wedding. Gone was the rather attractive bob, now Jenny's hair was short, almost boyish. She was wearing black trousers and a plain white shirt. The one other thing that John noticed was Jenny did not seem so voluptuous as he had remembered. In fact she looked decidedly flat chested.

"I'm not late, am I," John said rather nervously.

His shyness was beginning to creep back. He was starting to feel unsure of himself again. This immediately changed when Jenny gave him a long kiss. She was the one that was showing the most assertiveness of the pair. To John this was truly amazing, because he had never really been with a woman before. This was sending strange signals of mixed emotions.

 

Jenny suggested that they go for a walk in the local park and since John had no other suggestions, this they did. To start with as they walked side by side, there was no physical contact between them. It was Jenny who slipped her hand into John's. This startled him at first when she did this, but after realising what she had done, this for some reason, made him feel so proud. As the walk progressed, so the physical contact progressed as well. By the end of the walk, they were arm in arm and John loved every bit of it.

 

So it seemed, after all these years, John had at last found himself a girlfriend and he felt good about it. Gone were any doubts he may have had about his sexuality although he had many doubts about how to proceed next.

What was to be this next stage?

Should he kiss Jenny?

What if she rejected him?

Would there be any chance of taking this further?

If so what should he do then?

 

Although John perceived Jenny as shy as he was, in reality she was the one that was actually making all the moves. It was her that was leading John, subtly from stage to stage.

It was Jenny who took John's hand.

It was Jenny who linked into John's arm.

And it was now Jenny who was about to initiate their first kiss in public.

So that is what she did, there and then, in the park, she turned round to face John, put her arms around his neck and gave him a full kiss on the mouth. John, to say the least, was taken aback, but he did nothing to stop her. In fact all he could feel at this precise time was a rising in his trousers. When Jenny broke away, she said,

"Sorry."

John said nothing, he was too flabbergasted to reply, he was rather taken aback with Jenny's boldness. The only other reaction Jenny could see was that John had gone quite red in the face. Jenny continued,

"Are you all right, John?"

John eventually gathered himself together enough to splutter out,

"Yes I'm fine."

Jenny beginning to get a bit concerned, said,

"I haven't offended you, have I?"

"No, " John blurted.

"Are you sure?"

"Quite sure."

This incident passed with John, actually, feeling elated and Jenny still a bit concerned about what she had done. Really all this was the progression of this relationship, which although going painfully slow, was making some headway. In fact, once back in Jenny's flat, the kissing resumed, John having got over his initial shock in the park.

 

Over the following weeks the relationship began to flourish, the two of them seeing each other most days. John, though, always left Jenny's flat at a reasonable hour in the evening, the thought of staying all night never entered his head. Jenny, for her part did want John to stay overnight. She also wanted to have sex but she knew that between the pair of them, because of their shyness, that this would a long time in coming. She thought that she would probably have to take the initiative when she thought the time was right, just like their first kiss.

 

Chapter 3

 

Progress

 

Jenny and John's relationship had been steadily progressing, however slow, over the past number of weeks, that Jenny thought the time was about right to take it to the next stage. That next stage, as far as Jenny was concerned, was sex. If John was not going to do anything about it, then she was. Jenny knew that John would be round at her flat that evening, but instead of the usual, which was a meal a drink, a walk and a kiss goodnight something different had to happen.

 

So Jenny decided she would dress 'appropriately' in the hope that this might spur things along. Although she had bought a new outfit for the wedding, she didn't want to wear this. Really, Jenny didn't have a lot of clothes that were suitable, as she was a person that tended to dress very simply, even underneath. But this was an emergency, so that lunchtime, she went to the high street to buy a few things for the evening. She bought a Wonderbra, a pair of lacy French knickers, a matching suspender belt and a full slip with lace trim, all in white. Other things she bought included a pair of sheer black stockings, with lace tops, a white satin blouse, a rather short black skirt, a new pair of high-heeled shoes and lots of make-up. As a result she was late back to work and there were a few comments from the other girls there about her purchases and what she was up to. Jenny said nothing.

 

Work over for the week, Jenny set about transforming herself for the evening ahead. She stripped naked, removed any hairs on her legs and underarms and sunk into a bath of hot soapy bubbles.

 

Out of the bath, Jenny dried herself and started to dress in what she hoped would be her seduction outfit. On went the new French knickers followed by the suspender belt. The next item she put on was her new Wonderbra. In her opinion, she needed all the help she could in that department. She had also worn a Wonderbra for the wedding but on this occasion she considered it not appropriate as it was a bigger size and she was hiding something then.

 

Next the stockings followed by the make-up and red nail varnish. Normally Jenny did not usually bother with much make-up or nail varnish but on this occasion, she would lay it on a bit thicker than normal, almost tarty, she thought. On went her slip followed by her new skirt and blouse. The finishing touches included watch, rings, a bracelet and a pair of clip on earrings. Jenny slipped on her new shoes and looked at the finished result in the long mirror in the bedroom. She thought to herself that if this doesn't get John going, then nothing will. So it was now just a matter of waiting for John to turn up and take it from there.

 

John turned up at Jenny's flat precisely on time. If Jenny had any criticism about John, his time keeping was not one of them. If he said he would be at a place at a certain time, then he was definitely a man of his word. When John saw Jenny in her new clothes as she came to the door, he was somewhat taken aback. For here again was that rather glamorous person he had first seen at the wedding, that person, frankly, he had fallen for. He had got used to, over the past few weeks, to Jenny looking boyish in her trousers and shirts. To see her looking like a woman again began to start something stirring inside himself. On seeing her, standing at the door, he said,

"You look nice."

"Well thank you kind sir, please come in," Jenny replied.

So in he went. Jenny had done other preparations for this night. She had prepared a delicious meal and they would eat it by candlelight. There was wine that if all else failed she would use it, to excess, if necessary to try and get John to loosen up. Actually it turned out that John was putty in her hands. The combination of the clothes and the atmosphere did the trick. It was still Jenny who had to initiate every move. However she tried to orchestrate it so that John thought he was in control.

 

Once the meal was over, they both settled on the settee in the lounge where Jenny said,

"Well did you like the meal?"

John replied,

"It was lovely, thank you very much."

Jenny went on,

"Well thank me properly."

John took this to mean that she wanted a kiss. So that is just what he did. Jenny however made sure as the kissing started that she was going to put some real passion into this. When their lips touched, Jenny opened her mouth and let her tongue stray into John's. John could do nothing to stop this, even if he had wanted to as Jenny had put her arms around his neck and was holding him in an extremely firm grip. This went on for a while with Jenny almost climbing on top of John, and with all the scrambling around, a couple of buttons had become undone at the top of Jenny's blouse. John noticed this and Jenny noticed that John had seen this, and before John could say anything, Jenny took his hand and laid it directly on one of her breasts. She had put her hand on top of his so that he couldn't pull it away. Jenny whispered to John,

"Let's go through to the bedroom."

John could do nothing to stop this. He was nervous, very nervous, because he was not sure what to do next. Jenny was making all the moves and he was powerless to stop her.

 

Chapter 4

 

Revelations

 

As they nervously started to take off each other's clothes, Jenny couldn't help but notice the way John would hold each of her garments, so gently, so lovingly. First came Jenny's blouse, and then it was John's shirt. Next came Jenny's skirt followed by John's trousers. Jenny now stood in her beautiful white satin slip and John slowly, but nervously guided the straps down her arms to let the garment fall to the floor. By this time Jenny was down to her bra, French knickers, stockings and suspenders and John down to his underpants. Instead of leaving the slip lying on the floor, John picked it up and as he did allowed it to touch his body, in fact he made sure that he held it to his body. It was the way that John had held Jenny's slip to him that aroused Jenny's suspicions. She said,

"What is it John?"

John suddenly realising what he was doing, quickly pulled the slip away, threw it on the bed and spluttered,

"It's nothing."

Jenny persisted because she saw that John was trying to hide something.

"Are you sure?"

"Yes quite sure."

The next thing that Jenny said really made John reel.

"Would you like to put it on?"

"Put what on?"

"My slip, of course."

At that particular moment, you could have wiped the floor with John. It was like a bolt out of the blue. John's face went bright red and Jenny seeing this said,

"I think you would, wouldn't you?"

John replied,

"I think I had better go."

"No, I'm sorry. Please don't go."

"Well I don't think you would want me to stay."

Jenny went on,

"Look I really want you to stay because I think we've got a lot more in common than you might realise."

"I don't understand."

"Neither did I until a few minutes ago but I think you will."

Any thoughts of sex at this moment were completely gone and Jenny suggested they both get dressed, which they did. They went back into the lounge, Jenny poured two large drinks and they sat down on the settee together. Jenny said,

"Would you like to talk about it?"

"Talk about what?"

"You know, what you are feeling being with me."

"I don't know."

"Well is it new? Is it different?"

"Yes."

"Is it me?"

"Yes."

"Is that all?"

"I'm not sure."

"Is it something to do with the clothes I'm wearing?"

"Possibly."

These questions were beginning to embarrass John and he really was not quite sure why. Jenny was noticing John's embarrassment and realising she knew the answer, came out directly and said.

"Is it that you would you like to dress in my clothes?"

John got even redder, Jenny repeated her question before John replied in a tiny voice,

"Yes, I think so."

"Wait there."

Jenny got up from the settee and left the room leaving John somewhat dumbfounded. He really did not know what to think. Should he stay or should he go and that would be an end to the possible start of any relationship with a woman he ever had. Anyway, he had just convinced himself that he had blown it with the things he had just said. He was just about to get up from his seat and leave when Jenny came back and said,

"Where are you going?"

"I thought I had better go," John replied.

"Don't go, please."

"I think I've probably embarrassed you because I've certainly embarrassed myself."

"Don't be silly, there's nothing to be embarrassed about. In fact everything is ready, so why don't you come through to the bedroom?"

Jenny took John by the hand and led him into the bedroom, almost forcibly, where lying on the bed lay some beautiful items of lingerie plus a blue satin dress. There was one other thing that John noticed was a wig in the style that Jenny had worn on the day of the wedding. Jenny said,

"These are the things that I wore on the day of the wedding, the day we met, and I would like you to now wear them. Will you please?"

What could John do? He was seeing laying on the bed some beautiful clothes, especially the underwear of the type he had only seen in magazines and although he had never worn anything like this before, he had this amazing urge to dress in them. He stood there for a moment open-mouthed.

"Well?" Jenny said.

"Well what?" was the reply.

"Are you going to dress in these clothes or not?"

"If you like."

"Thank you."

This was followed by a kiss. Jenny went on,

"John, there's just one thing I would like to ask. If you dress in my clothes, will you prepare yourself properly, please?"

"What do you mean?"

"Well, shave your legs first?"

"If you like."

"Thank you again. So shall we do it then?"

"Yes."

Jenny led John to the bathroom where she showed him where there was a razor so that he could shave his legs and body hair, if he wanted. She handed him her dressing gown as he entered the bathroom asking him to wear it when he had finished. John was excited, elated and nervous about what might happen soon. There was one thing; he decided he was going through with it because something inside was urging him to do so.

 

John did what was necessary in the bathroom, not only did he shave his legs, he shaved all his body hair off, arms, chest and even his pubic area to leave himself completely smooth. He dried himself completely and put on Jenny's dressing gown. It felt nice. It felt right.

 

On hearing John coming out of the bathroom, Jenny called him to come into the bedroom. While John had been in the bathroom, Jenny had changed, gone were the skirt and blouse, she was now dressed in trousers and a shirt. To John, she looked quite good in them, almost male in a boyish sort of way.

"Well, what do you think?" she said.

"You look fine."

"This is the way I prefer to dress. Right it's your turn now," Jenny said summoning John to sit on the seat at the dressing table. John did as he was asked as Jenny began the task of transforming John into Joanne. He queried why the dressing table mirror had been covered with a towel. Jenny replied that she did not want him to see himself until she was finished because she thought it would be nicer that way. First was the plucking of eyebrows, which John did not care for much, but he said absolutely nothing to indicate this. Next came make-up foundation cream, which Jenny smoothed on his face, slowly and deliberately. Jenny got John to turn round and face her as she applied blue eye shadow to John's eyelids.

"To match your blue dress." she said.

A blusher was applied next with a soft brush and the whole thing was finished off with a bright red lipstick. The wig was removed from the bed and placed carefully on John's head. Jenny adjusted it and brushed it and looked and said,

"Yes, that is nice."

She removed the towel from the dressing table mirror to let John see himself and said,

"Well what do you think, Joanne?"

"Pardon."

"Well I can't keep calling you John when you look like that, can I?"

"I don't know."

John or Joanne was not really that interested in names at that particular moment because all that was in his mind was the reflection before him. He was seeing himself in a way that he thought he should be. He was seeing his female side for the first time. In his eyes, this looked right and thinking, had Jenny seen this even before he realised it himself. He couldn't be absolutely sure because he thought that Jenny had her own thoughts about herself. Jenny saying that it was time to get dressed interrupted John's thoughts. By this time, of course, any reluctance on his part to dress in women's clothes had completely gone. As far as John was now concerned, he couldn't wait to get into these clothes that were lying on the bed and if, because of this, he was now to be Joanne, then so be it.

 

Jenny handed John a pair of white satin French knickers with a lace trim. He put them on eagerly. Jenny said,

"Take your time, we've got all evening."

At this point he removed Jenny's dressing gown to be standing there only in the French knickers and to reveal to Jenny his now hairless body. Looking at this she gave John a peck on the cheek and merely said,

"Thank you."

"What was that for?"

"For doing things properly, that's what."

The bra produced was a Wonderbra which Jenny guided John's arms through the straps. She fastened it at the back after which, with John sitting again and her at his back, she pulled the fleshy bits from his chest to fill the bra cups. This immediately gave John the impression that he had a small, but noticeable, bust. But more was to come; Jenny produced two silicon inserts for the bra cups to give a bigger and more voluptuous bust. John now realised that Jenny had been wearing them on the day they met. On Jenny's instructions, John stood to allow the matching suspender belt to his French knickers to be fastened into place around his waist. At this point Jenny said,

"You see, normally I don't wear things like this. I only got them for the wedding and for this evening."

"Oh, I see."

"All I really see is someone who can appreciate them more than I ever could. Am I right?"

"Yes, I think so."

Next came the stockings, the sheer black stocking with lace tops. Jenny showed John how to put them on by first bunching them up and slowly and carefully rolling them up his legs before clipping them to the suspenders. He was feeling good, in fact he was feeling great, but still questioning himself, why. His stockings on, John stood up on Jenny's request and led to the front of the long mirror at the other side of the bedroom.

"Well, what do you think?" Jenny queried.

John said nothing, because in front of him stood a woman in her beautiful underwear, this woman, of course, was Joanne.

"Well?" Jenny repeated.

Joanne, who John now considered himself after seeing his reflection in the mirror, still said nothing. Jenny now getting a little concerned, said,

"Are you all right, John?"

John coming to his senses replied,

"Er, yes. I'm sorry, I got carried away. Anyway I thought you wanted to call me Joanne now?"

"You certainly did. So what do you think, Joanne?"

"It's nice, I like it. But should I?"

"Why not, if you like it."

"But what about you?"

"What about me?"

"Well, what do you think of me dressed this way?"

"Put it this way, since you've started to dress this way, your shyness has disappeared and you're more confident in yourself."

"So I am."

"And to top it all, you look good."

"Do I?"

"Yes, but let's finish dressing you."

"All right."

Jenny led Joanne from the mirror back to the bed where she lifted the full slip from the bed, put it over Joanne's head, guided 'her' arms through the straps and allowed it to fall down over his body. Joanne shuddered in delight at the feeling of the silken material as the slip fell down around 'her' body. Next Jenny held Joanne's dress so that 'she' could step into it and it could be pulled up. Joanne's arms were guided into the sleeves and Jenny zipped it up at the back. Joanne's slip was adjusted so that 'her' dress sat properly.

 

The last thing to be produced was a pair of high-heeled court shoes. Joanne slipped them on, they fitted perfectly. Joanne wondered,

"Does Jenny have the same size of feet as himself, or did she get these shoes specially?"

Jenny requested Joanne try a few steps in 'her' high heels. 'She' did so and as if he had been wearing them for years, 'she' walked around the floor full of confidence.

Jenny said,

"Well, you've certainly got your confidence. Anyway shall we finish getting you dressed?"

"I thought I was finished?"

"No, there are one or two things left."

"Fair enough," as Joanne sat at the dressing table again.

Jenny requested that 'she' hold out his hands in turn as she applied a bright red nail varnish to each nail in turn. As each hand was completed, Joanne had to make sure that 'she' touched nothing until the varnish was dry.

 

The final finishing touches were, one of Jenny's watches was strapped to Joanne's left wrist and a gold bracelet to the other. Round 'her' neck was fastened a gold chain to match the bracelet and to 'her' ears a pair of clip on earrings were fastened to complete the transformation.

 

Joanne now stood up from the dressing table and was directed to the long mirror to see 'herself', as 'she' really wanted to be.

Again Jenny asked,

"Well, what do you think?"

"I'm amazed I could look like this," was the reply.

Jenny went on,

"I've seen pictures of men dressed in women's clothes who will never look anything other than that and will never, in a million years, ever look like a woman. But, there are some men who actually look better as a woman than a man and as far as I'm concerned you're one of those. So welcome Joanne. Welcome to the world of womanhood."

 

Chapter 5

 

Where Do We Go From Here?

 

"Is this really how I should be?" said Joanne.

"I think so," replied Jenny.

"So what do I do now?"

"Put it this way, what do you want to do now?"

"I don't know. I'm confused."

"Let me put it another way, are you happy being Joanne?"

"Yes, that's why I'm so confused."

"There's no need to be, if you're happy that way then that's the way you must go."

"Must go?"

"Yes, must go. Ask yourself this. Do you want to become a confident attractive woman or a shy, rather effeminate man?"

"I think you know the answer to that."

"Well, you know in which direction you must go."

"But how?"

"Would you like me to help you?"

"Yes, but how?"

"Well for a start, why don't you move in with me?"

"Are you sure?"

"Of course."

"Then what?"

"Let's see what develops."

"Why are you doing this for me?" Joanne said with concern now rising in 'her' voice.

"In a lot of ways I'm doing this for myself," Jenny replied.

"What do you mean?"

"Remember when I said we've probably got a lot more in common than you realise?"

"Yes."

"Well with me I'm not really that keen on men."

"But you went out with me."

"True, but I saw something else in you."

"What?"

"Your feminine side."

"My what?"

"Your feminine side. I could see in you that your feminine side was dominant."

"Well I never knew anything about it."

"Perhaps it took someone like me to see it and bring it out."

"But what are you trying to tell me?"

"About me or about you?"

"About us both."

"Well, now that I've brought out Joanne, I want Joanne to move in with me."

"As friends or as lovers?"

"Really, let's see how things develop."

"I'd like that., I really would."

"Thank you," said Jenny giving Joanne a big kiss on the mouth.

"Obviously you're going to need more clothes."

"Like what?"

"Like everything, bras, knickers, slips, blouses, skirts, dresses and anything else you might need."

"Yes I will, won't I?"

"Perhaps tomorrow we can make a start."

"O.K., but what about tonight?"

"Well tonight, my dear Joanne, I would like you to stay here with me. I have a nightdress for you wear. Actually I bought the nightdress for myself in the hope of using it to seduce you as John. I've never worn it."

"But I thought you didn't like men?"

"That was Plan B, if you like. I was, if we had made love going to persuade you to wear it."

"Oh, I see."

"But I don't think any persuasion will be necessary now."

"You're probably right."

Joanne thought how things had developed in the last few hours, from being a very shy man with absolutely no confidence to now being a woman, with no shyness and full of confidence and looking forward to 'her' new role in life. There were obviously going to be problems in the future with work and their friends but at this precise moment, Joanne put them out her mind. Actually, Jenny made the suggestion that they both sell up and move to a new area where Joanne could be accepted as a woman from the outset. This sounded like the best solution.

 

The End

  

  

  

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