A transgender, smoking involved, slightly twist ending story.

Yes! I'm a crossdresser Mum! in that one simple sentence, Alan was fully exposed in the worst possible manner, to his own mother in her house and in mostly her clothes.

And the smoking! she exclaimed, He felt more shame and embarrassment over this one, as for years he had been so vocal in trying to make her quit, yes, I smoke a little too Mum, but never when I am wearing my male clothes.

But you,,,,I?,,, you, Oh I can't think Alan, and she stormed out of the room.

This was the beginning for Alan and the end. He was frozen to the spot the cigarette burning in his hand unable to think, he took another long drag and exhaled toward the ceiling.

The weekend had been planned and looked forward to, with such meticulous care and attention to detail. His mother was due to go away for a long weekend to see family and he had the whole house to himself from Friday lunchtime till Monday teatime, but this was NOT how it had played out for him.
He had the clothes, he wanted, borrowed and his, the cosmetics, the wig, the breast forms everything in fact to become his alter ego, even a bottle of an expensive white Chardonnay was in the chiller, and so, at noon he had waved goodbye to Alice his mother, right on cue, as she left for the airport.

Alan had not "chosen" to be a crossdresser, as no-one does, it was within him, a burning need that made him feel "normal" feel "right" feel like he looked on the inside.
Alan was a 27 year old male, he had moved back home after working in another part of town when his company was forced to shut, thanks to the recession, and as a recently qualified interior designer, his company was a victim of the banking fiasco. He had been a crossdresser since his early teens and had quite a collection of items but none of them made him feel quite as feminine as his own mothers clothes as ones that a real genetic woman wore, or would wear, even though he had many identical pieces.

Alice? well she was a bright beautiful and youthful 44 year old who looked acted and dressed about half that age in fairness, and Alan adored how she looked and dressed and wanted, no, wished, prayed even, that he could be just like her. He dressed all through his teens and when he moved away continued much more freely and frequently by amassing his own double wardrobe much of this was still packed away in the garage attic for fear of being found out. He adored her elegance and her shape and had his own style almost to the point of being a twin of her.

The weekend was his big chance to release all that desire and need, and now it was his downfall, that Volcanic Ash had really cost him, possibly everything he had.

After the shock of the face-off calmed, his mother re-entered the room with a freshly lit cigarette and even though he was in mortal fear, part of him felt a true pang of jealousy looking at her in her beautiful suit.

She was the first to speak. "Why do you do it"
" I don't know really, I need to, I enjoy it,,,"
She interjected "So, are you gay then?"
"No! I do not do it for that"

She continued, "why then, what is the motivation for this, this, this,,, I can't think what to call it?" then said, "I did know you experimented a little when you were younger, but put it down to a phase, you must have become expert at concealment as I thought it passed"

Alan finally responded, "I adore looking like you do, I love the way the clothes fit, drape and fall, the movement and the way breasts move and feel on me, I can't explain it more that that"
Alice was getting bolder, so you like looking like a woman then?

Not just any woman thought Alan but caution erred and he simply agreed.

"OK then now tell me about how the Anti-smoking nark my son was, became what looked like a very accomplished and probably hooked, smoker?"

"Muuuummmmm!" was all that came out, but she persisted, he had to think of something and it then all came out in a blurt. "I wanted to be like you, to understand what you feel when smoking how you looked doing it made it seem so appealing that I put aside my disgust for it,I wanted,,,,,,"

"To be a copy of your own mother?" she finished the sentence astutely.

"I'm so so sorry" he said and finally he broke down a little.

Alice wasn't mad at Alan, she wanted to hug him right there as she felt his pain almost physically but needed him to express his inner true feelings to her to give her closure. This was a life changing event and for both of them, so she wanted to understand the detail.

Alice asked again, "so you prefer looking like me and acting like me?"

A long silence followed by simply, "yes, I do"

"Your life choice will be very difficult for you, it will be something that will cause you mental anguish if you continue" wise words from Alice that didn't fall on deaf ears as Alan adored being like his mother more than anything and was this an offer to let him continue?

"Your not mad then? but you don't want me to continue? I need to stop right?"

Alice sat down and lit another cigarette before throwing the pack to Alan, he blushed but she signalled to have one and right then need was so strong, he wanted it so lit a cigarette inhaling just like his mother a long cheek hollowing drag, after a few seconds it hit the spot.

"No" Alice said, "I think you cannot stop either, and if I kicked you out, apart from being a dreadful mother, you will continue in any case so I think you should try another way"

Alan felt excited and nervous, what was coming now? "I would like you to dress permanently for the next month as,, what's your girl name? would you be willing to try this?"
Alan hadn't given himself a name, in truth he had always stopped short of that and told her that, so Alice selected the name that she would have given Alan had he been born female, she said "OK Chloe" for the next month I want to give you the opportunity to live here as you are now, do you have enough outfits and underwear or do we girls need to shop?

"Yes and Yes" came Alan's response, and so Alice set to work on making Chloe look that little bit more passable by re-doing her cosmetics and sorting a lovely skirt and jumper to wear out to the mall.

Chloe's first trip with Alice was scary and frightening as it always was going to be but the two managed to look and feel so natural that Chloe was soon relaxing into the role as she found no one stopped no one stared no one really paid much notice.

She even had the courage to join Alice for a cigarette outside of the large Debenhams store and then she did spot how guys would watch discreetly, a notion she wasn't altogether comfortable with. After a lot of shops a lot of spending and a load of carrier bags, the loaded the car and the two drove for home.

By now it was getting late and both of them were tired, a lot had happened and been said in a short time and they both needed some thinking space. Alan however would find sleep difficult that night as he felt incredible excitement for the coming month more than the fear and dread of actually doing this role.

When Alan woke it was mid morning, the routine of not working had got him into the routine of sleeping in again, and when he ventured down to the kitchen his mother was finishing off on the phone.
"Morning sleepyhead, get yourself fed and ready for a long day" she said and he duly complied.

"We have a couple of places to go this morning and over lunch so wear jeans and a T shirt for now, oh and don't shave, we are going to have your beard growth looked at" Alan was perplexed, what was she meaning? he always kept his face ultra close shaven to take advantage of any opportunity to dress up.

They arrived at a beauty spa where she told him he was going to have a treatment on his facial hair, he didn't question it but after the laser removal process began he was racing in his mind about the impact on the return to being Alan at the months end.
After the course was over they had a few minutes to wait and Alice wanted a cigarette, " want one" she asked? Alan had never smoked as a male and didn't plan to change than now, but went with her for the company, "are you not addicted yet then" Alice continued, "No I don't think so" said Alan, He had never felt the cravings his mother so enjoyed and did often wonder how they would make him feel, but the stinging in his face and neck kept his attention more than the sight of Alice enjoying a needed cigarette.
It was then time for him to have his body waxed, everywhere and this was NOT a pleasant feeling for him but he figured no pain no gain, after finishing they stopped at the hair salon and a friend of Alice's pierced Alans ears.
"This female lark is very painful Mum"
"Well it is part of your month's regime but rest assured the worst is over,,,for now honey" Alice quipped.

After doing some shopping for food they returned home and Alice instructed Alan to retrieve his clothes, "ALL of them!" and to have a shower.

When that was done they had a process of transformation into Chloe and Alan sat bewitched as his mother applied moisturiser and foundation over his still red skin. This will show me what I am working with she told him and after the sensitivity subsides and redness goes will look far more natural.
Alan didn't argue he dressed in a beautiful knee length skirt and satin vest top, his freshly waxed skin tingled and when he put on his wig stood transfixed at the reflection in the mirror, he looked so much like his mother her gene's were strong in him and despite a male shape he could have quite happily stood in a line up to guess the gender.

Alice had been busy on the internet as well and over the next few days a waist cincher and a gaff arrived and in those two items alone Chloe took on shape and form, with the addition of a human hair lace cap wig, and silicone forms, Chloe was becoming much more real than the old Alan had ever achieved on his own.
Then there was the smoking, Alice wasn't prepared to let Chloe be around and not learn to smoke elegantly and like her, and so she gave him lessons on how she held and inhaled the smoke held the cigarette though this was something Chloe had practiced her instruction made it seem much more real. The drags were to be much longer and deeper, "Do it like you are a real smoker, the important part is the inhale" she told him "the exhale should involve you cocking your head and pursing your lips, look this way" as she exhaled a long cone toward the ceiling.

Chloe practiced but the strength of them would take a bit of getting used to and the quantity! as he had only ever had one or two a day, this was such a thrill and quickly his shyness of smoking in front of her wained as Chloe grew in confidence. Chloe did notice that first thing in the morning her mouth felt a little "raw" almost which she knew was down to the amount and strength of the smoke being consumed, Alice told her that it was her morning reminder of being a smoker and she would become accustomed to it, but secretly Chloe loved it, as it made her feel even more like Alice as a shared experience.
Chloe also noticed she had to clear her throat more often until she had a cigarette Alice knew this was more than clearing her throat but didn't mention it's real cause.

"It is only for the month isn't it" he asked at breakfast "I mean isn't this laser treatment is permanent?" Alice reassured him it would all be fine and he was not to worry. His skin was feeling far more normal again by this time and he did like not having to shave so hard each day, and his legs in a skirt, well they felt so shear, this month would fly past he feared.
The two set off for a lunch in town Chloe naturally nervous but in a conservative jacket and skirt with a plain white blouse that truly exposed the shape and curves of her lace gel bra and forms if not in sight the semi see through fabric did a wonderful job in creating the illusion of real female form.
Chloe smoked at the same pace as Alice and slowly the taste and feeling become more normal and by the second weekend, Chloe felt so at peace, that already dread was growing for the end of his "punishment"

It wasn't until they had been to the cinema near the end of the third week that Chloe emerged and was first to reach for a cigarette, Alice had a knowing grin as she accepted one of Chloe's and watched her cheek hollowing drag followed by a five second hold then exhale, she know Chloe was becoming a smoker if she hadn't already become one as her eyes were glazed in the pleasure of that moment.

Alice decided to probe it a little, "you seem to be enjoying that" she said, "Oh yes,,,,, I needed that" was all the answer Alice needed, "and you seem to be enjoying this experiment as Chloe too, maybe too much, do you want to stop? there is only a few days left" she teased Chloe's fearful eyes told Alice that she was having too much pleasure to go back to being Alan, ever, just as she had suspected, so decided to try a softer tease instead.
"Chloe, if you enjoy this so much, as it has been fun for me too to have a daughter why not just keep going, say another month? maybe two?"
Chloe was being teased and she knew it, "maybe? or I might just go back to being Alan!"

Alice was too wise for that, she know he didn't want to go back but wanted to go forward and that was the plan made. That evening the two had another frank and upbeat discussion, Chloe loved this new way of life, she had been made aware that after only a few weeks she was finally matching inside feeling with outer appearance, and she knew she had become hooked as each morning she woke "needing" a cigarette, it had moved so swiftly and enjoyably that from being as simple as one or two every few days, now, she was averaging 20 to 25 a day and even after an hour or so, felt those same feelings of need Alice had been experiencing for many many years, and who also loved it. It was strange she could no longer smell her own smoky smell any more, she had gotten used to how smoky she was after each cigarette but now, well now she just smelt her perfume. Alice told her this was another step in the process with smoking that it becomes a part of your being and you feel the non-smoker is the one missing out as they will never know the pleasure and delight of enjoying a cigarette as the need takes you. Chloe although new to it was very quickly understanding that the habit easy to pick up quickly took full control over you, and felt her penis stiffen at the thought of being held in nicotine's unforgiving and firm grasp.

Now, what happens next? Chloe was starting to wonder when Alice said that they had a meeting with a gender clinic to discuss how Alan as Chloe could move forward.
"If you are going to stay as Chloe, we need to know what is best to do about, you know, your obsolete parts,,,?" Chloe was a little mixed in feeling as she loved being herself as she had become, but didn't know how or what in particular to move on with.
The meeting was very reassuring after some initial hesitancy in those first few minutes a floodgate soon opened and Chloe talked and talked with the councillor and the first second and third sessions were text book, at the fourth meeting Alice was with Chloe and the councillor said that it would be a good time to start on a course of HRT, Chloe was to read up on the full implications in a booklet that was given to her and if she was ready take two tablets daily.
Naturally Chloe started almost as soon as they had the prescription filled and the feelings made her ecstatic inside, reassurance of being a woman externally to match her internal vision, however, her development was not the fastest nor the slowest and her body slowly took on a new more pleasing female shape and form, her emotions roller-coaster of tears and laughter followed a prescribed path and inner peace descended over her. After nine months her breasts were a full A+cup if not a B and she discovered that wearing even a T shirt was no longer something she could do with out a bra due to discomfort of rapid movement, just another little pleasure as she was a most womanly girl.

If Chloe was going to go further then she had to start earning and as a qualified Interior Designer, she could start working self employed from home, a website and some adverts later and Chloe had a meagre but growing list of clients and potential clients for home and office design work and the best part? no one suspected she was anything other than a young pretty woman.

Alice frequently commented that she almost never wore trousers, infact she didn't have a single pair of jeans, preferring a demure pleated skirt and top to almost anything, this made Chloe look more than her 29 years but pleased her so Alice was pleased. Never going out in plain clothes established her with her clients too as she was never less than elegant and knew her craft of design inside out.
Alice asked her one day about this, Chloe told her that as a man anything goes but as a woman she felt it her obligation to be pretty and feminine at all times and even round the house was always immaculately turned out. Of course elegant women smoked as role models in Holywood and indeed almost everywhere could be seen smoking and Chloe was gripped by her passion to smoke and tried to always let it be known in her style that she too was that which she aimed to be.

Alice seemed to enjoy watching Chloe evolve as the HRT and the ongoing councilling expanded Chloe's horizons she had developed a buxom figure and Alice often commented that she had a better figure than she did to Chloe's inner delight, she had found a new appetite for food also and that combined with the hormones gave her a beautiful curving waist, and genuine pert breasts that Chloe found uncomfortable if not supported in a bra, but to gain the figure she dreamed of would mean surgery, and both of them knew that to wait for this would not be what Chloe wanted and so with her new income growing healthily, she told her councillor that she planned to fully transition. This was a big and bold step for Chloe but one that was a natural progression on from living as a woman to becoming one, she cleared a ten week gap in her schedule to have several procedures done, the biggest of them was gender re-assignment.

Operation day dawned and Chloe and Alice checked in at the private clinic, the outline was full SRS, breast, and facial feminisation a major step and one longed for as the hormones had long since rendered her male parts useless.

Recuperation was long and tedious but her new body had curves in all the right places her face now unrecognisable from her 27 years as Alan and for her 30th birthday Chloe celebrated on a cruise as a woman, legally in the eyes of the world and in her own eyes which was arguably the more important factor.

She had returned to her working and had converted the garage into a beautiful office suite where, naturally she would design and operate from able to indulge her design passion.

The surgery only made Chloe more elegant and she had worked on her deportment ensuring that her new sashay was as much a feature as a cigarette when she walked around the city, she turned heads too, often but as yet had never once thought of being anything other than single, she was still more attracted to women somehow?

It was at the flat of a new client one afternoon a woman called Liz Farley, that she made a very unusual discovery, Chloe was discussing the project and the designs and Liz seemed more interested in Chloe, the tow talked and it became clear Liz was flirting with her, Chloe was out her depth but enjoyed the attention but Liz was "very" attentive. After the meeting was over Chloe was offered a glass of wine and accepted on the glass patio of the flat overlooking the river, Liz coyly asked if Chloe minded if she smoked and Chloe enthusiastically encouraged her and admitted to being a smoker as well, the two seemed quite comfortable and talk progressed to an invite to stay for dinner, and Chloe and Liz had a long lazy meal that was way too informal for mere business.
When she was ready to leave, Liz kissed her on the cheek and there was that lifetime long second where both of them seemed to want more but not know how, and it was Chloe who took the first step and kissed her again on the lips a very soft sensuous kiss, the taste of her cigarettes in Chloe's lips was intoxicating and Liz asked to see her again on the following Saturday,,, for lunch?

When Alice heard she was speechless, as she had sort of assumed Chloe would find male company more her thing but didn't show any disapproval, as this was another step another twist in the evolution from having a son to,,,,,,,,,,

Liz and Chloe spent as much time together as their bust schedules allowed over the passing days and weeks and they became truly bonded and lovers. It was only initially uncomfortable as the two presented themselves to Alice for the first time, Liz was far more feminine than Alice expected and was certainly not a woman you would have thought as a lesbian, but Alice could feel her love for Chloe and he total devotion won Alice easily over.

Life seemed to be settling down with Chloe after the turbulent time they had spent in the transition, her figure blossomed and eased into her now complete life.

End.