The Cross-Dressing Bet -- 레이디보이

I hadn’t seen my brother and business partner James or his wife Elkie since they headed off for a gap year. Part of the time they spent living with Elkie’s family in Korea and the rest traveling. James had still worked remotely on rare occasions when I needed his help with any difficulties in our joint website design business.

My longterm girlfriend June said she wanted to keep her distance from Elkie but would not say why, now they were back I wanted to spend my every waking moment with James and Elkie. We had exchanged harsh words about her unfriendly behaviour towards Elkie then June decided to spend the weekend alone at the beachside apartment that I half owned with James.

When I arrived at their house James and Elkie were busy in the kitchen, Elkie insisted visiting with a picnic basket would be a perfect surprise for June which is how the three of us came to disturb June in bed with a man I had never seen before. After June and her lover had left the three of us watched sunset from the balcony, then as darkness swept over us I became rather drunk. 

We sat in the living room watching their holiday photos scrolling on the screen on the wall. A bunch of the photos showed Elkie with a familiar looking woman and they both giggled and Elkie quietly spoke to James.

“Don’t you recognise her?” James said and they both lauged when I had said that she could be my sister if we had one. I could not believe what I was hearing as Elkie explained that they had rented an apartment in Seoul for a month where James lived as a woman “it has made him stronger as a person and much more confident” was just a couple of the benefits Elkie mentioned.

James was in a teasing mood and asked if I thought I could do it, Elkie cut in and said that it was unfair considering what had just happened with June, then she said that I was much more caring than James, not as strong but in a nice way. But the seed was sown and as I lay in bed that night with a head full of hurt over June I decided that if James could do it then I would too.

———//———

The bet was simple, the stake agreed over breakfast the next morning — I would take a hotel room in the city and for four weeks I would be wearing women’s clothes the only restriction was that I must not reveal to anyone that it was just for a bet. Elkie had tried many ways to dissuade me saying it would be too hard to do totally alone adding “James would never have been able to do it without my constant help”

Instead of putting me off it only served to make me want two things even more — in a brotherly way beat James at his own game and to find my very own version of Elkie. 

In my heart I already wanted to forgive June and take her back. In my head I was thankful that June was history as she would never have allowed the bet and I wanted to be stronger in every way just as Elkie had said James was. All that I had to do was win the wager…simple.

June would be livid when she discovered that I had cancelled the credit cards, car payments and rent on her apartment that I paid for her each month so I immediately had my cell number changed as I prepared to win the wager. Just as she had for James Elkie chose the name that I would use for the month — I would be 유진  or Yujin

I booked a make-over with a company that specialised and keeping to the terms of the bet I explained that I was starting over, moving to the city and beginning a new life at the same time. The person I spoke to was very helpful and after I had sent selfies they sent back a couple of ‘looks’ and suggested a shopping day also. 

———//———

The hotel was mid range, they had been happy enough to accept the month long pre-paid booking that I had made by telephone. I would arrive what I now understood to be described as ‘en-femme’

I met my personal shoppers for the day — Mike and friend Rachel, we started with coffee and the days trip was planned in more detail as my ‘daytime look’ was created which involved some discreet make-up and changing from boxer shorts into new panties with a built in gaff. Sort of androgynous would be perfect for me to start with Rachel had said. 

I had expected us to be shopping in some of the swanky department stores in the city, instead we took a bus to a shopping area in an expensive suburb and began trawling the charity clothes shops. Mike explained that by wearing preowned clothes I would not be standing out as ‘newly out of the closet’ I repeatedly heard ‘last seasons colours, worn just enough, people still wear this style’ and plenty more as we acquired more and more things. In the first shop the jeans I wore were declared suitable ‘boyfriend’ jeans but everything else was left on the changing room floor. Instead of £350 shoes I wore £4 grubby worn women's sneakers and instead of a £125 Droks shirt a £3 blouse in last seasons khaki worn open over a sports crop top.

None of us were dressed in our birth genders clothes which helped me feel that I was brave enough to leave the shop without shaking. I had money and cards, a hotel room booked and paid for, I was dressed in women’s clothes and wore make-up which is where reality began to kick in -- there was no way I could go home dressed like this.

By the time we arrived back at the makeover salon I had purchased a battered suitcase which now contained enough preowned outfits ‘for now’ and, I’m sure, more new lingerie and makeup than any woman needed.

Next came highlights to my hair to complete the look. Mike told me he was a transman as I sat having odd strands of hair pulled through the skull cap. I realised that Rachel had taken charge of my overall look as she explained about wigs being hot and sweaty, Mike was right that an androgynous look until my hair grew out would work. I cold not believe how different the highlights made me look, the stylist had worked wonders with them and they looked half grown out rather than just done a few minutes before. Watched by three pairs critical eyes I re-applied daytime makeup several times until two out of three of my watchers pronounced it good enough for now. 

When I introduced myself as ‘Miss’ at hotel reception it was without any hint of surprise. In all honesty even I was not sure if I was ‘Mr’ or ‘Miss’ when I had looked in the mirror before leaving the makeover salon. The thin foam lining in the crop top added just a hint of breasts that seemed to swing it towards ‘Miss’. 

After unpacking my new to me clothes I had a growing feeling that I was going to enjoy the month. Even-so I felt nervous about leaving the safety of my hotel room to get dinner and was just about to order room service when an unknown number rang my cell. Mike apologised for casting me adrift on my first night in the city and we were soon enjoying pasta at a nearby diner.

I was unprepared for when Mike asked me what I was going to for work and I said that I would have a few days off before looking for a job.

A few days had passed and the weekend was looming large, Mike had mentioned a pub about fifteen minutes walk from the hotel that was a good place to fit in when out alone. Friday night I was sitting at the bar with a beer when a group including Rachel came in and I joined them at their table. The barman came and sat at the table and began chatting to Rachel, she introduced Brian and mentioned that I was looking for work and soon enough I was behind the bar working a trial shift. In less than a week I had gone from male company director to a barmaid with a growing circle of new acquaintances. 

Even though I had no immediate need for money the job provided me with a way to occupy empty days in-between visits to the many art galleries and museums that the city housed. After mostly covering James’s job as well as my own for a year and having high maintenance June to support being single again days seemed to comprise of many more than twenty-four hours. James now returned the favour and covered my job and June had a new man to fulfil her many needs I assumed. 

I had been in the city a week and half when clicked on James and began a FaceTime, he switched my call to the wall screen and I could see the whole room and Elkie gasp as she walked into the room and stop as saw me on the screen. Are you fed up with hiding in the room yet James asked with a winners smile. They were both full of questions after I had told them about my job, museum visits and shopping. James hid in the apartment for a whole month Elkie said adding that I had already more than beaten him.

James joined in agreeing that I had indeed beaten him in every way and saying that he would pay up. 

“The room is paid, let’s make this more interesting…double or quits if I complete the month” I suggested with a smile and tauntingly added “if you are brave enough that is…”

———//———

Being the new employee I worked random lunchtimes and evenings at the pub as needed and willingly covered for people who wanted a shift off at short notice which made me popular with the full-time staff and in all honesty I was really enjoying the job as well.

Mike and Brian had both warned me about Lizzy the lunchtime regular who was sort of bi-curious and keen to lead people on before getting cold feet. Lizzy had dated Mike for a while and according to Brian Mike had fallen head over heels for her before Lizzy got cold feet and dumped him, now she was hitting on me.

Alcohol was getting the better of Mike when he said to me as I served him one last drink “even though you have hardly any male traits left at all now we need to get you looking a bit more femmed-up like Rachel, you do know Lizzy thinks you are a transman?” 

I kept quiet but after three celibate weeks the possibility of an encounter with Lizzy was seeming very attractive and a worthwhile challenge.   

There was another reason for my declining James’s offer to end the wager early. I had taken to eating lunch at a noodle bar in one of the city centre backstreets where I had noticed a cute waitresses who spoke Japanese with what I recognised from my time living there to be a rural South Korean accent. 

———//———

I did not have long to wait for Lizzy to make a move, as I left the pub Friday lunchtime I nearly walked into her. We chatted for a while and I accepted her offer of coffee at her apartment. Lizzy was all over me in the lift and the possibility of coffee was seeming remote. I was feeling nervous and vulnerable as I had chosen the shortest dress in my closet that morning to go with the stockings that I loved wearing since that very first day.

As we went into her apartment Lizzy made it clear exactly what she hoped for before coffee. All nervousness gone I turned away from her and released my cock from the gaff and let it tent out my dress just the way she asked. I had never met anyone like Lizzy, she was a real control freak and I was loving every second of it.

When we eventually got round to coffee Lizzy said that she only wanted a casual affair for as long as it pleased us both, most surprising was her revelation that she was married and her husband was fine with her having lovers. A casual affair was fine with me and fitted in well with the remainder of my months stay in the city.

Our second encounter Lizzy revealed that she had fantasies about lesbian sex while we had what she called ‘straight sex’ I nodded sagely not sure how me being fully dressed, and living as, a woman could be described as straight.

———//———

I had a rare Friday night off but as life and everyone I knew in the city revolved around the pub that is where I spent my night off. With just a few more days until the end of the month and return to my old life I was in a bit of a maudlin mood, would life in a village ever be the same again I was wondering as I waited for James and Elkie to arrive. I wanted them to see for themselves how well I had settled into this temporary life. It would be hard to describe how but somehow I wanted to try and explain how it was that I felt more confident inside.

More than anything I wanted to thank them. My nerves were on edge, meeting James and Elkie in real life and introducing them to my new friends was feeling more of a challenge than a simple FaceTime chat. I headed for the restroom one more time, that was when I saw the group of waitresses from the noodle bar at a table. I paused and hoping they recognised me said good evening. They giggled and replied in a friendly way all apart from the Korean girl who just blushed, speaking fast in Korean I introduced myself as 유진  or Yujin, the temporary name Elkie had given me and wished her a good evening. 예은 Ye eun replied as she began speaking quickly. 

We were still chatting when I felt a tap on my shoulder, James and Elkie had arrived. I introduced them to Ye eun.

Elkie and Ye eun chatted as James and I went to the bar for drinks, James insisted he paid as he was the man and giggled as he added “but not as big a man as you” then went on to say how he could never have been so confident in his cross-dressing month. James slid the money he owed me for the wager along the bar saying “double and you earn it”

Elkie arrived as I smiled and slipped the two pennies into the charity collection pot that stood on the bar. I glanced across at the now empty table where Ye eun had been. 

Picking up on my glance toward the empty table Elkie said “don’t worry, Ye eun asked me to give you her number” as she passed me a slip of paper. Then Elkie told James that I should return the two pennies as I had told Ye eun my secret.

I strenuously denied telling a single soul but Elkie giggled and said “I thought you knew 유진 is the name everyone undertaking the wager uses”

———//———