The Cross-Dressing Project

 I read some fiction on-line where the lead character wore woman's clothing, I think I would like to try it for myself.   ————    OK…we are professionals in our own fields lets embark upon this as a joint project with open minds.

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“I think my male menopause is beginning Fi, I’m having a mid life crisis.” Ladislau said.

“Don’t tell me, let me guess” Fiona replied as she abandoned finishing reading the news item on her tablet. “Mid life crisis, well I hope it’s not your new research assistant…please tell me you want to buy a Harley or a sports car or perhaps take up fishing.” 

Wine over dinner had put them in a playful mood.

“How could you suggest such a monstrous thing Fiona?” Ladislau said

Fiona’s playfulness kicked up a notch or two.

“She is very pretty Ladislau, young, flirty, pretty, busty, Abigail…even her name sounds pretty…the sort of girl young men’s wet dreams are made of. I would be devastated but I could understand if you have feelings for her…and I expect you have little pet names, you know, perhaps call her Abi when no one else is within earshot.” Fiona stared into Ladislau’s eyes in the way she knew he felt threatening.

“I was talking about your suggestion that I might consider a hobby like fishing when you know my thoughts on using creatures for entertainment…your other suggestion had not occurred to me but I can see advantages in that.” Ladislau paused, took a sip of coffee then continued “the young studs are always pursuing Abi, you really think I might stand a chance…” 

Was as far as the conversation went that night before Fiona silenced Ladislau with her lips and all thoughts of a mid-life crisis were forgotten.

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Sunday morning rolled around again and their routine began. Ladislau brought coffee out on the patio where Fiona sat reading the arts section of their regular Sunday broadsheet newspapers. An hour or so slipped by as they swapped sections of the newspapers. 

Fiona finished her paper and lay it on the table. “You never did tell me what form your midlife crisis is taking.”

Ladislau had been waiting for this moment, no reason to be coy. “I want to try wearing woman's clothes Fi.”

There - it was out there - come what may, no backsies.

“You want a sex change?” Fiona said.

“No Fi, I just have a desire to wear woman's clothes sometimes not to be a woman. In private of course, if you think you might be OK with it that is.” Ladislau said.

“Do you think it may be a hormone imbalance, have you had your levels checked recently?” Fiona said.

“They were fine in my annual check-up a month ago. I read some fiction on-line where the lead character wore woman's clothing, I think I would like to try it for myself.” Ladislau said, sipped his coffee and pulled his ‘ugh’ face. “Only with your agreement of course…shall I make some fresh coffee?”

“Yes please, my coffee is cold. Can you send me a link over so I can get up to speed before we next talk about it?” Fiona said.

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“My issue is that some of the practices outlined in the fiction you linked I would find distasteful.” Fiona said after she had read some on-line fiction and googled cross-dressing.

“Wearing woman’s clothes in the fiction quickly moves into situations which I find unacceptable as well. My interest lies purely in the clothes.” Ladislau said.

“We could exchange lists, yours of what you want, mine of what I would like to avoid and use them as a starting point.” Fiona said.

“Excellent suggestion, how about next Sunday after breakfast?” Ladislau said.

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They both sat to read the Sunday papers as usual, Ladislau made fresh coffee as usual. Not as usual they exchanged lists and sat considering the contents while drinking their coffee.

“Your short list almost makes mine unnecessary.” Fiona said and placed Ladislau’s list on the table:

1. Wearing woman's clothes remains our secret

2. I wear woman's clothes when we agree.

3. Choice of clothing a joint decision.

4. Either of us can decide to stop.

 

“I’m a little surprised at some of the things on your list Fi.” Ladislau said as he placed Fiona’s list on the table:

1. We do not involve others
2. Only at home 
3. No fetish/sexual undertones
4. No uniforms
5. No domination on either part
6. No female clothing in bed
7. No oral sex

“I must say I am rather relieved, I had this awful idea that you might want to prance around like a maid or sex worker instead of a nearly 50 year old woman. What sort of look are you thinking of?” Fiona said.

“I’m not sure, what would you suggest Fi?” Ladislau said.

“You must have an idea perhaps something like I wear…” Fiona sips her coffee and enters tease mode “…or is there a little something Abi wears you imagine slipping into.”

“I’m pleased you are being so supportive about this but please don’t tease Fi.”

“Oooh…please don’t tease me…” Fiona says in a camp voice and is giggling “is that what Abi says?”

Ladislau laughs along, thinks how much he wants this but how nervous he is of it becoming a reality.

They are in the bedroom. It’s too late now for second thoughts. Fiona is busy with a measuring tape.

“I need your measurements not the measurements you think you are Ladislau” Fiona moves on to tapping at her phone. “All finished.” 

Ladislau recognises her finger movements as online shopping while he dresses in chinos and shirt ready for lunch at the village pub - The Bell.

“As you are not sure what you want to wear I’ve added some suggestions to your M&S online shopping basket. Big pants should accommodate you, just one pair to try. Do you want a bra?” Fiona waited. “Blush tells me nothing. Yes or no?”

“Yes”

“Yes to…?” Fiona said as she struggled to keep from laughing.

“To a bra” 

“How are you going to wear woman's clothing if you can’t even say ‘yes I want a bra Fiona’?” Fiona crossed her arms and pinched hard under her arm using pain to keep from laughing.

“I would like a bra please Fi” 

“There - I’ve added a sale bra to your basket, that should be enough for now.” Fiona passes over Ladislau’s iPhone “and I’ve added 4 pretty summer dresses in your basket so that you can you chose your favourite then delete the other three and checkout while I change for lunch.”

“Just one dress?” Ladislau said.

“One outfit for now, let’s see if you like being a cross-dresser before you buy a whole bunch of things” Fiona calls out from inside her walk-in closet. “If you were the same size as me you could order a dozen dresses.”

“I’m not a cross-dresser Fi.” Ladislau calls back.

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The green parcel from M&S had an urgent look to it when arrived first thing Tuesday then sat unopened until Saturday morning. 

Fiona had a trip with ‘the girls’ to a local art exhibition then lunch planned for the day, their part-time domestic helper Maude was not working until Monday, Ladislau had cancelled his round of golf.

Fiona was ready to leave the house, Ladislau was trying to delay opening the parcel until after Fiona had left. 

Fiona’s iPhone rang “Hi Alice…running a little late…Ladislau wants to show me something…see you soon” she ended the call. 

“Come on, get a move on, hurry up and get dressed.” Fiona said.

“You can go” Ladislau said.

“Not until you’re dressed, we are not playing the flogged to death ‘my wife came home and caught me’ fiction favourite” Fiona smiled “are you going to wear make-up? I could do a quick makeover if you want before I go.”

“No, no make-up thanks Fi” Ladislau said as he opened the parcel and hung the dress.

“Good choice, that dress was my favourite too.” Fiona said as she picked up the bra and slackened off the shoulder straps for him. “Panties first.”

Fiona watched as he slipped the big pants on and suppressed a smile as she watched his cock growing and filed his reaction away for ‘future reference’ as she held her hand out saying “here is your bra Ladislau.”

She watched him struggling to fasten the bra for a while. 

“you could try hooking it at the front then spin around and slip your arms in until you get a bit more practice” Fiona said as she took pity and clipped the back for him, spun him around and put a hand in one of the bra cups. “Scoop your little man-titties in…one…two…” then helped herself to a squeeze. “Step in your dress and I’ll help you with the zipper.”

Ladislau had not spoken since he put on the panties.

“That’s it” Fiona said as she guided his fingers helping to close the zipper. “Don’t forget this little hook right here at the top or the zipper might work loose during the day…how does it feel?”

“I’m feeling more nervous than anything” Ladislau said

“Well now I have seen you wearing your dress that you chose, my guess is the bit to be nervous about is over…look at the time the girls will think I’m not coming.” Fiona leant in and kissed Ladislau. “I doubt any of my sandals will fit you, perhaps you could wear your white sneakers for now.”

“How long should I wear this?” Ladislau said.

“Until you don’t want to…or until we go to bed tonight if you want - either would be fine with me.” Fiona called as she  opened the street door.

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“Ladislau… Ladislau…are you home…” Fiona called out. She had checked the study and lounge, now she was at the bottom of the stairs.

“No, I’m out” Ladislau called from somewhere upstairs.

“Very funny, why are you upstairs? Are you coming down?”

“Are you alone?” Ladislau said

“Of course…is that what all of this hiding is about?” Fiona smiled inwardly as Ladislau finally appeared at the top of the stairs still wearing the dress.

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“Are you wearing your dress this morning” Fiona asked as they lay in bed Sunday morning.

“Do you think I should?”

“No it is not what I think is it?” Fiona said as she leant across for a quick kiss. “I’ll ask again, are you going to wear your dress when you get up?”

“Yes I will…until we change to go out for lunch.”

“I bought a pair of thong sandals for you, they are in my closet.” Fiona said as she stepped towards the shower. “Do you need my help with your bra before I get in the shower?”

“Might not wear it, it keeps sliding up when I lift my arms.” Ladislau said.

“Loosen the shoulder straps.”

“I tried that they slip down.” Ladislau said.

“It’s not easy is it?” Fiona giggled “but you really should wear a bra at your age.” Another giggle.

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Fiona went to make fresh coffee while Ladislau continued reading the papers, when she topped Ladislau’s cup up she said “make the most of this morning Ladislau it’s your last chance to wear your dress until next weekend unless you plan to wear it one evening.”

Papers read, coffee drunk they set off to change for lunch. Fiona burst out laughing as Ladislau stepped out of his dress. “Whats so bloody funny Fi?”

Fiona eventually got herself under control “all these years I have always thought that you were a feminist. Now you shave your tits.”

“It’s not funny Fiona, my hairy chest was the reason for my bra slipping up.” Ladislau said

“Don’t you ‘Fiona’ me missy.” Fiona said still laughing.

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Fiona was first home, Ladislau would be another hour. The house smelt wonderful - Maude had cooked a curry for them while she was there earlier and left it ready to heat through. 

Fiona phoned  Ladislau to give him the good news and to make sure he didn’t stop at the pub on the way. “I’ve left a little present on our bed for you to wear at supper.” Fiona said.

She poured herself wine then set the table for two, a candle-lit supper would set the mood perfectly she thought, the second glass of wine had disappeared as fast as the first. Fiona was three glasses in-front by the time Ladislau sat at the table wearing his present - a plain navy blue dress.

 Fiona took tiny morsels of curry and rice on her fork, the alcohol had taken the edge off of her appetite. “Can I ask you something personal Ladislau? You don’t have to answer.”

“Of course, anything.”Ladislau said.

“well…I have noticed when you put your panties on.” Fiona paused and seemingly turned her thoughts toward the curry, she was regretting drinking so much wine on an empty stomach, she continued “that you seem aroused by them…I’ve been wondering…”

Fiona forked a piece of meat in her mouth and chewed slowly - no rush.

Ladislau concentrated on his food.

Finally Fiona plucked up courage to say “Do you masturbate when you are cross-dressed?”

Ladislau sipped his wine but before he could answer Fiona continued. “Most cross-dressers do according to the internet, it’s not a problem Ladislau I just wondered.”

“I’m not a cross-dresser Fi.” Ladislau said.

“Of course you are, even Wikki agrees. Would you prefer I call it ‘dressing’?”

Ladislau said “Dressing does sound a little less judgemental but saying ‘I am a dresser’ does not really work does it? Sounds like I am furniture. Cross-dressing is fine. To answer your question…” was as far as Ladislau got before Fiona cut him off.

“I’m sorry Ladislau don’t answer, please forget I asked.” Fiona loaded a forkful of curry and rice. “The wine I drank before supper has gone to my head and I’m feeling a little drunk. I had been wondering if that was the motivation to begin dressing and the alcohol has made me less than tactful, sorry Ladislau.”

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Fiona was driving, it was her turn. 

Ladislau would be drinking, it was his turn.

They were heading to a friends house for a dinner party.

“It’s your months anniversary today” Fiona said.

“Of what?” Ladislau said.

“Of becoming…of starting your hobby” Fiona said.

“It’ OK to say of being a part-time cross-dresser. I am so there is no point in me having a hissy fit about it.” Ladislau said.

“Why haven’t you bought more clothes? Autumn is coming and I am fed up with seeing you in that one summer dress.” Fiona said. Out the corner of her eye she saw Ladislau smile. “Have you been waiting for me to suggest that?”

Ladislau nodded a yes.

“You are a real sweetie, more so since you began part-time cross-dressing” Fiona said as she glanced away from the road ahead and smiled. “I like the new and improved Ladislau mark 2.”

“You really think I am different?” Ladislau said

Fiona nodded “Mmm…when dressed and it lasts for a day or two after. Others have noticed a change in you as well.” Fiona paused while she negotiated a roundabout. “Angela said I should keep an eye on you, said you are at a wandering age. If only she knew how wrong she was.”  Fiona laughed. “That you are the other woman.” 

Ladislau joined in with Fiona’s laughing.

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Fiona was surprised when Ladislau burst through the kitchen door one Friday afternoon laden down with bags full of groceries. “I’ve bought some things we could have for Sunday lunch, does an ‘at home’ weekend sound a good idea Fi?” 

“Not sure I am that keen on spending a weekend cooking Ladislau. Is there a special reason?” Fiona said.

“We could share cooking.” 

Fiona sensed an underlying excitement in Ladislau and a rising playfulness inside her. “That sounds a wonderful idea, just us, a romantic weekend, how sweet…are you playing golf tomorrow?”

Ladislau said “only in the morning.”

“Oh and you have bought my favourite wine.” Fiona said as she unpacked the bags “two bottles…are you planning to take advantage of me?”

Ladislau smiled “would you mind?”

“I would be offended if you didn’t. One rule for the weekend.” Fiona threw a serious look Ladislau’s way. “No part-time cross-dressing this weekend.”

Fiona saw the instant change in his face, inside she was bursting with laughter.

“Oh come on Fi…”

Fiona said “The answer is NO and don’t pester me to change my mind” Ladislau had the look of a sad dog that had just received even sadder news. Together they finished unpacking the groceries. Fiona noticed the small packages from their favourite upmarket deli and imagined what treats they contained. 

Ladislau looked ready to say something, 

Fiona was ready to deal her final ultimatum. “I am taking a firm line with you Ladislau, I do not want you changing back and forth until Monday…male or female…whatever you choose to wear this evening needs to be for the whole weekend.”

Ladislau wore an ear to ear smile as he double thumbed his phone “ducked out of golf” he said as he pressed send. 

——————————

With Ladislau’s 50th birthday close Fiona had been thinking of something special for his milestone birthday. 

“I know you think we are too old for surprises Ladislau so I am telling you in advance. You need to book a week off work. I know it is two weeks before your birthday but that is when it must be” Fiona said. She had been researching online and had managed to get a booking for ‘the’ week. 

“Will I need my passport?” Ladislau said in an effort to find out what Fiona had planned.

“That won’t work - your passport is valid for another 8 years. And we both know how useless you are at packing so don’t even bother asking if you need winter or summer clothes, I’ll pack appropriate clothes for us both.”

——————————

“Maude asked me some questions today, she asked if we are satisfied with her work. Any idea why Ladislau? Have you said anything to her?” Fiona asked Ladislau even though she had a good idea of the reason.

“No I haven’t spoken to her apart from offering a cup of coffee.” Ladislau said.

“She thinks someone may have been dusting, perhaps hoovering the rugs. Why would she think that?” Fiona said as she noticed Ladislau was blushing ever deeper now.

“I might have hoovered some crumbs up.”

“Might have?”

“OK when I am home working I sometimes take a break, do a bit of housework…well I can’t go for a walk or shopping can I?” A crimson Ladislau said.

“What exactly do you wear when you do a bit of housework?” Fiona said.

“Nothing special, whatever I’m still wearing when you come home. Why?” Ladislau said.

“Well it might be better not to do her job the day before she comes that’s all.” Fiona giggled “perhaps cooking supper would be a good alternative.”

——————————

“Are we driving there?” Ladislau said as he pulled off the drive onto the road.

“Turn left. Stay on that road for 23 miles” the satnav ordered.

“She sounds like Abigail don’t you think?” If Fiona’s grin could not have been any wider “do you like it when satnav Abi orders you around Ladislau?”

“Why did you insist I wear this corselette under my male clothes, it’s very tight, a little uncomfortable to drive in” Ladislau had a barely detectable whine in his voice.

“It’s hurtful when you say ‘this corselette’ as if it is someone else's. If you don’t like the first part of your early birthday present we can spin the car around so that you can slip it off, I don’t want you feeling uncomfortable. We are still only a few minutes from home.

“I really do like it, and it is much better than having to keep fiddling with my bra. It’s more nerves Fiona, you know, being out in public, wearing my corselette in the car. Please god we don’t but what if we had a road accident and had to go to hospital Fi?”

“So bad that the nurses needed to cut your clothes off?” Fiona said still smiling, she was anticipating his reply and could not wait to make her killer comment. She had to pinch her thigh to keep from bursting into laughter. 

“Exactly.” Ladislau said all serious while nodding.

“Well if we were that badly injured I expect the nurse would say - look this man has pissed and shit in his new corselette.” They must have looked like maniacs to anyone seeing them drive past as they both cried with laughter.

As calm returned to the car Fiona revealed that they were heading to a holiday camp at Blackpool. A week of old fashioned British entertainment all provided on site from supermarket to clubhouse with entertainment provided every night. “Even better this week is adults only.” Fiona excitedly added.

As Fiona outlined the growing list of facilities Ladislau’s enthusiasm grew as well. 

“Sounds a great way to step back from the pressures of modern life. We could even have a week without screens or phones.” Ladislau said.

“That is a brilliant idea.” Fiona said as she leant over to plant a kiss on his cheek. “I’ve been worried that you might have though it too old fashioned. Without tech we will be old fashioned as well.”

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“Wait in the car, I’ll check us in and get the chalet key.” Fiona said as Ladislau stopped the car at reception. He was checking out the facilities shown on the large ‘site map’ hoarding when Fiona got in.

“Look Fi, two club houses, an olympic size pool, crazy golf, supermarket, courtesy bus to seafront - we won’t even need the car for the whole week.” Ladislau said with enthusiasm. Fiona had their chalet key and some ‘what’s-on’ leaflets. 

They were sitting in the chalet recovering from the car journey and drinking tea when Ladislau spotted him.

“Look Fi there is one…no…two cross-dressers walking past. What’s the chance of two?”

“Pretty good chance I would say.” Fiona said as she handed him the what’s-on leaflets.

——————————

“I’m a little sad to be leaving” Ladislau said.

“And I am pleased you enjoyed the week, I was worried I had made a bad mistake that first day.” Fiona said.

“If you had told me you had booked ‘cross-dressing week’ at a Blackpool holiday camp I would never have wanted to come, now I don’t want to leave.” Ladislau said.

Fiona giggled “your face was a picture that first day, and that first night we went to the clubhouse…”

“You looked nervous as well Fi as everyone looked at you.”

“You bastard.” Fiona said, but she was laughing “are you suggesting they weren’t sure if I am a woman?”

“Do you think some thought I was a woman Fi?” Ladislau said.

“This is real life Ladislau not some internet fiction, it’s how you feel on the inside that matters not how you look to anyone but me.” Fiona said.

“So I still look like a 50 year old man in a dress and wig?”

“Pretty much.” Fiona said. “The best 50 year old man in a dress and wig in the world.”

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“It’s me” Fiona said as she tapped on their bedroom door, there was a scraping sound as Ladislau took the chair from under the handle. He stood behind the door as Fiona carried their tray of coffee in and set it down on the dresser. Ladislau wedged the chair back under the handle.

“There really is no need for that Ladislau, no one is going to come in here.” Fiona said.

“Just in case…it makes me feel safer, this is not Blackpool.” Ladislau said. He was still wearing his favourite A line dress which came to mid calf with a shortie cardigan worn loosely over. “How are the final preparations coming along?”

Ladislau’s 50th birthday had finally arrived and preparations for the nights party were nearing completion, all of their friends and plenty more from the village would be coming.

“The caterers are nearly finished setting out the buffet, time for a coffee before we change.” Fiona poured their coffees “I really like your new wig and it looks really natural, are you pleased with it Ladislau?”

“Yes, especially the colour. It goes so well with my skin-tone don’t you think?”

Fiona nodded an agreement. “Have you heard about Penny?”

“What?”

“Well you know about Gerald’s affair with his secretary?” Fiona paused while Ladislau nodded “Penny is giving Gerald some of his own medicine and is having an affair with Angela now.”

“That’s all old news Fi.”

“Only a month or so.” Fiona said, Ladislau nodded “now no one cares or even mentions it anymore.”

Fiona walked into her closet as if the conversation was over, she returned with the dress she had bought for the evening and hung it on the hook on the door next to Ladislau’s suit.

“That is a pretty dress.” Ladislau said

“You think I haven't noticed you jealously eyeing it up?” Fiona let a little smirk spread. “Have you thought what it might be like to wear it tonight?”

“In my dreams…imagine what people would say.” Ladislau said.

“The same as everyone said about Gerald, his secretary, Angela, Penny and plenty more people besides.” Fiona paused “for a couple of weeks gossip would circulate then it would all be forgotten…history.”

“I guess you are right, must be hard to ignore the initial gossiping.” Ladislau said

“Only if you are listening.” Fiona said.

“That is your dress next to your suit, my dress is in the second bedroom, I’m going to change.”

Fiona lightly kissed Ladislau on the cheek. “Wait until everyone is here before you come down to make your birthday entrance. Wear the suit or dress - whichever one you choose remember I am your excalibur ready to defend you from incoming gossip…”

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