The Making of a Crossdresser

Mai kicked her foot against Director Akihiro’s office chair as she stepped into his booth where he was busy, hunched over the pile of letters he was signing. Acting as if she had tripped Mai steadied herself by placing a hand on his back.

“Sorry Director Akihiro” Mai said as she firmly passed her thumb, one way then the other, across the bra strap adjuster as if it were some sort of a game controller button in a, yet to be invented, crossdressing game. Mai wanted to leave no doubt they both knew of the bra strap adjusters existence. 

It had been weeks since they had met in the office when she became suspicious. Mai had purposely not mentioned anything to her coworkers. She felt certain she was the only one to have seen a hint there may, at times, be a bra beneath his clothes, if Himari, Ema or Rita had even the faintest idea Line would already be buzzing with gossip.

Since the lockdowns of the early 2020’s the company had downsized two floors of offices for full time staff to one open plan office with booths and a conference room. Like the other staff Mai was only required to spend 15 hours a month in the office. The reason for her visit was to connect her laptop to company intranet for a system update. Outside the day was a balmy twenty-two degrees Celsius and sunny, Mai and Director Akihiro were alone in the office.

Mai had her entire day planned out, Mai planned everything, she had arrived in the office two hours before the shops opened in the Ginza district, she had more than enough time to enjoy her iced latte while her updating laptop made sounds as if it were chewing cotton wool, she had arranged for a courier to collect then deliver her laptop to her apartment that evening. Mai was not the sort of woman to lug a heavy bag with her while clothes shopping. The one thing Mai had not planned for was Director Akihiro’s brassiered presence in the office…it altered everything.

Director Akihiro had the look of a muntjac deer caught in the headlights of a silver Toyota Corolla on a country lane in spring as Mai’s thumb moved. Mai intentionally threw a fleeting look of wide-eye surprise before returning to normal “I tripped over your chair base…how long are you in the office for Director Akihiro?”

“Until 11:00 Ms Mai”

“Me too, we can get coffee and cake after” Mai smiled the sort of smile that, in some indefinable way, dared him to decline her suggestion. “I know where they make the best ichigo cake in Tokyo, is that still your favourite?” Of course it was. The entire office knew his ex had sometimes sent ichigo cake to the office for him. Using the language of cake Emily knew exactly how to send coworkers clear messages that Akihiro was hers.

Director Akihiro nodded his agreement and went back to his letter signing, Mai wandered back to her booth and typed out a long text. The reply came immediately as if the recipient had been balancing on one leg in a cold place. At 10:30, right on time, the courier collected Mai’s laptop, she feigned busyness while she waited for 11:00 to come around. Mai sent her final text of the conversation just as Director Akihiro was reading through the last letter, Mai heard a sound as he replaced the cap on his Platinum 3776 Century fountain pen followed by the snap of the fastener on his pen case. Director Akihiro stood just as Mai was a couple of metres away “perfect timing Director Akihiro, the taxi I ordered for us is waiting outside” Mai had no intention of giving Director Akihiro a single opportunity to remove his bra.

———//———

As the taxi pulled to the kerb Mai handed the driver a slip of paper on which she had written Director Akihiro’s home address, she instructed the driver to take Director Akihiro’s backpack and laptop bag adding “Director Akihiro does not want to carry bags while we shop, please leave them with the concierge in the foyer of his apartment block”

“We are going shopping?” Director Akihiro said, the surprise in his voice obvious even to the taxi driver. Mai just nodded and smiled. He was unusually quiet as they sat drinking coffee “you were right Ms Mai, this really is the finest ichigo cake I’ve tasted”.

“Thank you Director Akihiro”

“Shall we be informal as we are shopping together, please, call me Akihiro”

“Then you should call me Mai as we are having an informal shopping trip together Akihiro…” Mai began then went on to outline how ‘the girls in the office’ had noticed the change in his dress style and, Mai threw a slight blush, some missed smart Director Akihiro. “I never would have imagined seeing you in the office wearing a hoodie let alone while eating cake in Ginza” Mai briefly glanced at Akihiro as she spoke, his ears had a red tinge.

Akihiro nodded in agreement “I know how casually I have been dressing recently” Akihiro explained that since Emily had broken off their engagement he had let things slide a little “thank you for telling me others have noticed, I will return to the old Director Akihiro’s dress standards” he smiled “lets shop”

“I need to freshen up first” Mai said as she stood leaving her iPhone face up on their table. She stood just by the corridor to the restrooms watching Akihiro’s back, if he turned around she could pretend to be returning, she checked her watch 10:29, she smiled, 10:30 she heard the faint sound of a message arriving on her phone. Mai quickly walked to the table, Akihiro’s attention was on the iPhone, so much so that he did not look up when she sat down.

“Is that my ex Emily?” Mai nodded “you know each other?” Akihiro’s voice sounded as nervous as that of a baby rabbit in September.

Mai smiled, nodded “Mmm from yoga class” Her iPhone had been swivelled 180 degrees. Mai picked up her iPhone, pulled a deep blush as she slowly read the message:- ‘do I mind if you get coffee with Akihiro? Why would you think I care? You can have him…my gift’

Mai deepened her blush as she struggled to stop herself from letting the inside smile escape to her lips. She owed Emily for both the perfect timing and perfect wording. Akihiro was looking puzzled the way men do when unsure what is happening.  

“I wasn’t sure if you two were still…” Mai looked deeply embarrassed, mumbled an apology, said the message seemed to give the wrong idea “I just didn’t want Emily to get the wrong idea if she saw us…” Mai needlessly dabbed the corner of her eye with a tissue “this was a bad idea…I should go” her hand lay conveniently atop her iPhone between them on the table. 

Akihiro had, unlike Mai, joined the blushing contest unintentionally “I expect Emily misunderstood… just between us Mai she has a new man in her life. Regardless of that there is nothing wrong with coworkers getting a coffee or shopping” he had missed the invitation of Mai’s hand completely.

“Are you sure about shopping together?” Mai said as the hidden smile forced its way to her mouth

“I would be mad to turn down fashion advice from the most stylish person in the office” Akihiro smiled “let’s shop”

“That bra is too small” Mai said before they stood, Akihiro had the exact same look that a muntjac deer would have after being struck by a Nissan Cube and was just about to breath its last breath “it is so tight it shows…was it Emily’s?” Mai waited for Akihiro to either collapse under the table or breathe. He did neither and, as if in a secret nodding society, moved his head. “What size chest are you?”

“92cms”

“And what size is the bra?”

“C70” 

“What is wrong with you?” Mai shook her head “for goodness sake just buy a bigger bra that fits” she stood “lets go”

———//———

Once Mai had assured Akihiro for the Nth time that she would not reveal his secret they wandered the malls and concentrated on shopping. Akihiro was spending big time and bought two business suits, shirts and shoes. Rather than be weighed down with bags they rented a locker and made regular trips to store their shopping bags. Mai was somewhat more conservative choosing a new top and only one pair of shoes. “I can wait here” Akihiro said as Mai stepped into Intimissimi.

“You will come in” Mai replied surprising herself almost as much as Akihiro. That Akihiro meekly obeyed surprised her but pleased even more. Recently when Mai and Emily were out drinking together Emily had said that after dumping Akihiro she realised he was a real wimp. 

The ease with which Mai had gotten Akihiro into the lingerie store had proven Emily right. Mai smiled at Akihiro, with every step he took he was giving Mai a little more control. He was blushing even before they reached the aisles. Mai picked up a baby blue bralette and matching panties “what do you think about this colour” 

Akihiro remained silent, Mai gave him the look she had perfected for drivers that cut in line “bralettes are soo comfy, lacy but nice and stretchy, no wires digging in, no adjuster lumps to show…so what do you think?” 

“You should buy it…”

“Hold these” Mai passed him the two hangers that held the lingerie “hold them, now we need to look at some underwired bras”

When The Sales Associate arrived beside Akihiro Mai thought that Akihiro was about to give a practical demonstration of the much rumoured phenomenon of spontaneous human combustion.

“These are new in” The Sales Associate said as she took a matching bra and brief from the rack. Mai began browsing the next section leaving Akihiro with The Sales Associate “we have the same set in other colours, what about green?”

Akihiro looked at Mai for guidance, she now stood facing him but on the opposite side of the display rack. 

Mai looked at The Sales Associate, smiled “are all men shy like little boys?” 

The Sales Associate giggled “my boyfriend is the same, we get outside and he is full of advice”

Mai turned towards Akihiro “pick out a bra and panty set B80 bra, M panty. Don’t just pick up anything…shop as if they are for you” then she said to The Sales Associate “can you show me some yoga tops while he shops”

The Sales Associate glanced back toward Akihiro then quietly said “I can’t believe it, he really is carefully choosing”

“You mean carefully choosing like they are for him?

“For him?” The Sales Associate put a hand to her mouth “really? Now the sizes make sense”

Mai looked across to see Akihiro staring back. Mia and The Sales Associate both discreetly giggled.

———//———

Akihiro had picked out a black set and was holding the hangers at waist level while trying to avoid other shoppers as he made his way to where Mai and The Sales Associate stood at the counter. “Are these OK?” He said as he put the items on the counter and took out his credit card.

“Cute” Mai said

“You should check the bras fit” The Sales Associate said as she glanced directly in Akihiros direction.

“Bring everything to the fitting room” Mai said 

“You want me to go there?”

“One person to try on, one person to give her opinion” Mai said

“His opinion you mean” Akihiro said

Mai smiled, The Sales Associate smiled, Akihiro followed Mai.

“What the hell !” Mai said as Akihiro struggled to unfasten what was once Emily’s bra. The exclamation mark clearly audible, the red marks from the too small bra were clearly visible. “Don’t ever wear that again…second thoughts…” Mai smirked “could be ideal for a punishment bra, put it in your pocket”

“Why are you doing this?” Akihiro said 

Mai said how, as a girl, she would dress her brother or any boy who would let her in her clothes, “that is until Mum caught me” as she took pity and fastened the back of the black padded bra for Akihiro. As he looked in the mirror that filled one wall Mia took her iPhone from her purse then quickly took a few pictures.

“What the fuck Mai…delete them” Akihiro said as he heard the camera sounds

“Stop faffing around, put your new bralette on and get dressed” Mai pulled the tags and handed him the bralette and matching panties before turning her back on him. 

“Please pretend they are for you” Akihiro whispered as they neared the checkout. 

“Why would anyone think different?”

Akihiro put the black bra set on the counter, Mai put down the tags from the bralette set “these as well”

“Everything fit?” The Sales Associate the sales associate said. She was busy scanning the items. 

“They fitted her perfectly” Akihiro said feeling all pleased with himself for throwing The Sales Associate off track.

“Is that so? I would have thought they were far too big” The Sales Associate looked up at Akihiro. She brought several items from under the counter then begun upselling “an extra pair of panties for each set and hose, an expensive brand but worth every yen…will four pairs be enough?”

———//———

Akihiro was so pleased to leave Intimissimi that he tagged along with a happy face with the sort of expression normally found on a labradoodle after eating five chicken wings. Mai was in dress shopping mode as she told Akihiro about how, as a child, once she had dressed a boy in her clothes she would use pictures to make sure that she could persuade them to dress up again.

“So you tricked them then blackmailed them?” Akihiro said

“You could put it like that, I would have said that I simply encouraged them”

“Now you plan to ‘encourage’ me?”

“Plan is when something has not yet happened” Mai had heard the air quotes clearly “don’t you think I would find it more difficult to ‘encourage’ you to stop crossdressing?” Mai smiled as she took a second dress from the rack and held one in each hand “this one?” She raised one by a couple of centimetres “or this one?” He smile widened “or do you want both?”

“Neither”

“Choose…remember how ‘persuasive’ I can be” the air quotes echoed around the store until Akihiro spoke.

“Wearing underwear is one thing…dressing as a woman is totally different…a massive step”

“Just a small step” Mai smiled “the sort of small step you will take when wearing a pencil skirt and heels…now, back to today, one or both?”

Akihiro was still not ready to give up “it’s not like I would ever have occasion to wear…”

Mai cut in “of course you will…you can wear your new dress when we FaceTime tonight silly”

“But I am NOT wearing it outside”

“We’ll go with that for now” Mai’s smile widened “I will feel silly calling you Akihiro…do you like Akiko?”

Akihiro stared

“Akiko, Akiko…yes, sounds cute. Stop messing around Akiko and pick a dress” Akihiro took the blue sun dress from Mai. Mai said that was her favourite one as well “Akihiro, Akiko they sound so similar. Close enough for anyone not to realise” Mai was unsuccessful in keeping the smirk inside “like, for instance, if I quietly called you Akiko by accident in the office”

As Akihiro was paying for the dress he began to think about why he had instinctively chosen the blue dress rather than the yellow one, he wanted to wear his new black bra for the FaceTime and that would have shown through the yellow dress. He began wondering about if he should wear makeup as well…and where would he even begin with that, inside he hid a smirk as imagined how he could let Mai think it was her idea to suggest makeup…

“I said…are you hungry” Mai said loudly and with the tone a bank manager would use when refusing a loan application by a tall person.

“Sorry Mai I was thinking about tonight…excited and scared in the proportion of three to two” Akihiro smiled “and yes I am hungry, my treat”

“Can I choose” Mai said, Akihiro nodded “lets go to Ichiran Shibuya for the best tonkotsu ramen in the whole wide world” 

They collected their various bags of shopping from the locker and climbed in a taxi. “You said you were a little excited about FaceTime tonight”

“Sort of…now that I am getting used to us I think you might have speeded up what was going to happen eventually”

“What sort of ‘us’ do you think we might be?” Mai’s tone was suddenly serious, very serious.

Akihiro fumbled with the strings of his carrier bags as he said that he had never really considered Mai as a possible partner. The taxi drivers eyes constantly flicked to the rearview mirror as if it would ensure he did not miss a word.

“Us…if you are thinking us as a couple, romantically, I have some really bad news” Mai smiled “Even though she never said anything outright I got an idea that Emily can be quite bossy and I thought you might be quite submissive”

“Not sure submissive is the right word”

“Pull over driver” they were still five minutes from Ichiran Shibuya and Mai sounded angry “you need to pay attention to driving not our fucking conversation” 

Akihiro held out Mai’s bags towards her as they walked “no…you carry them Akiko” Mai said loudly enough for a couple walking towards them to look. Akihiro wordlessly complied.

They reached a park, not a small park and not a big park but a park that was average in every way. An average number of benches, an average number of cherry trees, an average size pond with an average number of ducks and an average number of children feeding them. Mai stopped part way along the path which led to some unknown place in the distance “this morning has been a test” Mai began “I have discovered that you might be my dream submissive, my very own Akiko to do with as I please” Mai paused, Akihiro did not know what to say and so he silently watched a squirrel that sat in a cherry tree that seemingly watched him right back. “You have already proven that you are not quite submissive, the use of ‘quite’ is completely unnecessary” the squirrel seemed as interested as the taxi driver had been “in just a few hours I have transformed you from Director Akihiro into my sub Akiko who obeys my every instruction” Mai paused again and for a minute Akihiro thought that Mai would rebuke the nosey squirrel but she simply paused to sip from the bottle of water that had been in her purse.

They began to walk a little further and took a branch in the path that seemed to lead in the direction of Ichiran Shibuya. 

“Have you enjoyed this morning?”

Akihiro considered for a moment as they walked “Six parts enjoyed, two parts scared and one part dislike” Akihiro liked the idea of being able to discreetly change his mind by adjusting the proportions of an answer”

“Only two parts scared” Mai looked pleased as she nodded “If we are to become a couple I must warn you that am not interested in men and will be very controlling. Some people that like everything to have a name would call me a dominatrix”

Akihiro felt unsure if he should reply. A crow sat in a high branch of the nearest cherry tree, it also seemed unsure of what the future held. 

When Mai finally considered that an appropriate length of time had passed she said “you can walk away right now, go back to being Director Akihiro and today will be as if it had never begun or we can go to lunch” 

“I am hungry Mistress Mai”

———//———

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