Thailand Ladyboy Romance and Life With Apple
Seems like these are never ending disaster stories many my own fault. After a couple more disasters lately I think I found a happy ending.
I am now 75 still fit and healthy in all ways. I have been coming to Thailand from Australia since 2017 mostly motorcycle riding and other pursuits. Where I left off in my last story I had just finished kicking a Pattaya bar girl out of my Chiang Mai apartment which was stupid. Guilty as charged. I was still looking out for a long term ‘take care’ relationship and I’ve had a few false starts along the way having said that I’ve never missed out in the short term.
Six months before COVID hit in February 2019 I had a very nice relationship with an older farming lady near Phetchabun. I was a replacement for her previous Danish man husband who she nursed (but never got a bean for her efforts) until he died of cancer. Her whole house was a shrine to him. She and her son ran a diverse farming operation with many different Central Thailand crops fruits and trees mangoes bananas papaya and limes. Being an ex farmer myself I enjoyed the farm life and I like pruning.
Unfortunately she was a terrible farmer to grow these crops on poor land with no chemicals. Lovely lady but her idea of aerobics was like doing her duty. In the end I really didn’t like living there in the village. I also had issues with some members of her extended family who were always trying to fleece me. So when COVID hit in 2019 I knew it was going to last a very long time so I decided to end things. Of course she was upset.
The Search Continues
Fast forward to 2021. The Western Australian government finally dropped the gate and let us out of Australia. I drove to New South Wales so I could fly to Thailand from Sydney. I enjoyed the whole Thailand Pass and visa application nightmare and finally arrived in Chiang Mai in December. I had friends there. I was going to try again.
I went through a sort of interview process with some older ladies I had met online lots of lunch and dinner dates. Some really beautiful ladies however usually some issues and no aerobics. With one lady I wasn’t even allowed back to her village because she was worried about her reputation. Another lady quickly pointed out the bald tires on her 4×4 pickup truck then she tried to sell me some illegal homemade wine that one of her friends had made. Another was in Chiang Mai for Thai boxing training but also a masseuse she wanted me to rent a condo for her and her two kids. A very close call. I found a great condo and I did eventually rent it for myself but then I found out from a friend that her real agenda was to run off to Europe with her stud Thai instructor.
The Pad Thai Lady
Now we are getting to the good bit. I met another lady who had a pad Thai shop who I clicked with. 55 years old good English funny and a nice body. We had some good times together below average aerobics but then she announced she needed 30000 Baht to fix her nose. Then she announced she was selling her pad Thai shop and wanted to open a beauty salon in another part of town. I was already starting to realize she would be difficult to get away from. Part of her salary was for rent on another condo nearer to her new shop some subsidy from me for fitting it out so I would see her three nights a week.
To her credit she was a fantastic cleaner my condo and clothes were spotless. But it gets worse. Then one morning she told me that she really doesn’t like aerobics. I knew then that somehow I would have to end it but not that easy. She agreed that I could see other ladies but I could not bring them back to my condo. Her beauty shop was struggling so I kept her on as a cleaner for a generous salary but still not sustainable. I had to use what they call love hotels in Chiang Mai. They are driving high society Thais mostly use them for their encounters. The most famous being The Love Boat.
Along Came S
Then along came S. I also met her online. She was completely upfront. She said she owed a lot of money and had receipts. The bank was going to take her to court for credit card debt. From a good family very little English a 13 year old son from one early marriage a business that COVID impacted badly. Today I have not found out anything bad about her but always at the back of my mind knowing my history.
So after meeting her one time she stated that if I could help her she would help me with anything I wanted. Sounded suspicious but I was interested. I asked her if that included aerobics. She said ‘all right’ and we agreed to meet. She actually picked me up at my condo and then off to the Love Boat hotel we went. I was very nervous but I must say she was a willing partner no problems. We agreed on a salary package. She was very grateful and it got her out of trouble. This arrangement lasted quite a long time and usually a meal after. However I must say at 75 the best aerobics of my life. And I have not missed out especially after coming to Thailand.
We got closer but then trouble was looming. The lady who was still my cleaner got instantly jealous and thought I was paying too much for S. One morning after she stayed overnight (but in separate bedrooms) I was waiting for her to go to work because S was coming to pick me up. The cleaner wanted to confront S. I didn’t want that to happen but let her talk to S on the phone who was in the driveway waiting to pick me up. Well she went off and terribly abused S and even called her several very bad names. She also threatened to kill the both of us. S was recording all of this on her phone but was very upset. I knew the cleaner was dangerous because I found out from other people. So I thought ‘This is it if she won’t leave I will.’
I thought I would never see S again. I said I was going away for a few days on my motorbike. After the cleaner finally went to work I packed up as much as I could to carry and went to another city in Northern Thailand. Not to worry I was getting bored in Chiang Mai anyway because of the pollution and traffic jams. With a little help I found a house to rent cheaply. I still had most of my stuff in Chiang Mai in my Chiang Mai condo but fortunately only one month left on my lease. I thought S would never talk to me again but it turns out S really wanted me to contact her again. I did after a few days. You’ll probably be thinking ‘Yeah she needs the money.’ There is that but sometimes you know when there is more.
So her best friend’s husband (a mean looking Thai man) and I cleaned out the condo without the cleaner even knowing. I was still afraid for my life as are some of my Chiang Mai friends. She moved everything to the new city. When the cleaner found out she threatened to kill us if she’s seen us again. At least the cleaner had enough pride not to trash the condo. So Chiang Mai is out of bounds for some time.
Turns out that S is a great cook and cleaner and takes care of me very well. She stays with me when she can and commutes to Chiang Mai for her business and son.
Story Two Falling in Love with P A Different Kind of Romance
I’ve been a physiotherapist for over 20 years and I’ve still not discovered an adequate explanation for that phenomenon we call romantic love that feeling that unexpectedly takes a hold of you when a certain person walks into your life. Sometimes it happens but usually it doesn’t. I’m 56 years old have been married and divorced three times. I am embarrassed to admit that I have had more girlfriends and encounters than I could count or remember. Still those special moments of wonder have only happened to me a handful of times. My last encounter may be one of those times.
In my preparation to visit the Land of Smiles I became well aware of the possible scams and deceptions that many travelers experience. Many YouTubers have become downright pessimistic and bitter about some of the women they have met in Thailand.
As for my story I landed in Bangkok December 5th around midnight. By 130 I’d arrived at my hotel the Sheraton on Soi 15. Too excited to sleep I cleaned up changed and went out walking down Sukhumvit Road around the Nana area. I was smiling from ear to ear as I had previously watched countless videos of YouTubers walking from Soi Cowboy to Nana Plaza passing the famous Thermae Cafe. I planned to spend time at all these venues before flying to Phuket on December the 8th.
Meeting P in Bangkok
So on the 5th around 2 AM I walked down to Soi 4 still in amazement that I had made it to Bangkok. I passed all the usual freelancers and ladyboys competing for the attention of the men walking by. Then somewhere around Soi 7 I saw a beautiful smiling woman sitting on a stool on the sidewalk. I stopped to say hi. I was stunned by her beauty. I could have sworn that I had seen that exact same woman in one of the many videos I had watched before. She said she had worked there for three months. Her name was P and she asked me if I wanted a massage. After my grueling 24 hour journey from Houston Texas a massage sounded like exactly what I needed.
I followed her into a dingy establishment up a flight of treacherous uneven stairs into an even more dark dingy room with mattresses on the floor. I thought this was a terrible situation to have a relaxing massage in. When I said I wanted to leave P suggested that she could come with me to my hotel and give me a massage in my room. By this time I realized that P was a ladyboy and I was apprehensive to say the least. But it was my first day in Bangkok and I figured ‘Why the heck not?’ After a wonderful authentic Thai massage I was feeling much better. During the next hour or so a very special time of affection and flirting commenced no aerobics as I was still freaked out that I was in fact with a ladyboy.
She offered to stay the night but I didn’t think that was a good idea. So she told me to message her on her Line app if I wanted to see her again tomorrow.
Disappointments in Bangkok
I managed to get some sleep that night and woke up still elated that I had made it to Thailand. I thought about P and considered her offer but thought there were way too many places and people I wanted to see and experience. The second night I went to Soi Cowboy and ended up at Crazy House. While it was still early I quickly understood how it got its scandalous reputation. In no time I was approached by a petite completely naked beauty. I bought her a lady drink hoping to spend time talking and seeing if there was any chemistry between us. Within a few minutes she suggested that I bar fine her for short time and take her back to my hotel for drinks. I thought this was kind of fast but when I opened my mouth I heard myself say ‘Sure why not?’
I have to say that it usually takes me a while to get comfortable enough and in the proper mindset to get physical with a woman but this lady wanted to get right down to business. Needless to say after a fruitless attempt at some aerobics things didn’t exactly work out. She was soon gone along with a few thousand Baht. The night was still early and I decided I’d finally visit the Holy Grail of freelancer establishments the Thermae Cafe.
In the videos I’d seen it was a wall of beauties regular Thai women with daytime jobs and regular lives who would spend a few hours at night hoping to meet an interesting foreign man and make a few extra Baht on the side. After doing two walk arounds in the cafe my experience wasn’t quite what I expected it to be. Then a pleasant smiling attractive woman grabbed a hold of my hand and wouldn’t let go. She propositioned me right there and then and said that for a normal fee I could take her to my hotel. I didn’t quite know how to say no so I agreed. The second encounter that night played out similar to the first one only worse. No attempt at conversation no small talk or flirting only right down to business. Again things didn’t work out and she was gone as fast as she had come.
It was only my second night in Thailand and my expectations were severely dashed. It still wasn’t even midnight and I was sitting in my spacious hotel suite feeling disappointed. ‘One more shot’ I thought to myself and headed out to Nana Plaza. It was loud and hectic music blaring go go dancers shouting out to passersby and grabbing hold of them if they were close enough. I poked my head into a few go go bars and finally went into one. It was loud small and crowded. I found a seat and spotted a drop dead gorgeous woman near the stage. I gestured for her to join me and she came and sat down next to me. She was equally as attractive as P and I assumed she was a ladyboy as well. This woman said that she was not however but I doubted her for some reason.
No sooner than it took for her lady drink to arrive at the table she asked me if I wanted to take her out as well. She asked me to pay her bar fine and ‘Coyote fee’ and that we could go to a private room. It was very loud in this place and any attempt at conversation was fruitless. At that point I couldn’t bear another disappointment and loss of a significant sum of money so I made an excuse to leave and returned to the hotel. By that time jet lag was catching up to me and I slept until 3 PM the next day.
Giving P a Chance
After two days in the Land of Smiles I thought my long planned holiday my journey to the end of the rainbow was going to be a bust. I woke up thinking about P as she had been my best experience so far. I text her and asked her if she wanted to go to dinner with me. The noise and chaos of Nana Plaza and Soi Cowboy the previous night had been off putting and left me with little desire to return. However dinner and a movie with P sounded just great to me. P showed up at my hotel looking stunning. We went to the best reviewed steakhouse in the area truly a first class experience with a price tag to match almost double the price of a steak dinner here in Texas but worth every penny.
Sitting across from P was mesmerizing and I soon began to relax. We sat shoulder to shoulder holding hands in the theater and I was happy as a clam. She offered to stay the night and I agreed. It was an innocent but tremendously satisfying night.
The next day P took me to see the Reclining Buddha temples and other holy sites in Bangkok. She referred to it as paying homage to the monks. She was pleased that I wanted to go and took her Buddhist faith very seriously. She also took me to a large mall where her cousin worked in the food market. Within the first few days I had already met two of her cousins and video chatted with her sister and father more than once.
P’s English was limited so we relied heavily on Google Translate. I was used to this arrangement as I live and work in a mostly Hispanic area in Houston many of my clients don’t speak much English so I had become comfortable using a translator. I learned that P was from Laos and traveled back and forth to Bangkok to work and support her family. She told me that she had a visa prior to COVID but since then she’d had to travel to Laos every 45 days to renew her current visa. She said her mother died when she was 10 years old from a lung disease and she lived only with her sister and her father most of her life. She said that her father had remarried a wonderful woman who had accepted her for who she was.
She told me that her father had been very physically abusive towards her when she was younger and forbid her to become a ladyboy. She also said that as an adult he eventually accepted her for who she was. She said she will be 30 years old in February.
I noticed that P couldn’t understand and speak Thai but didn’t seem to be able to read or write it either. She told me that her father was very poor and so she didn’t get to study. I didn’t pry into how much education she actually had but she didn’t seem to know about history such as World War II or current events. She also said she didn’t know who Elon Musk or Donald Trump were. None of that mattered to me. In America we tend to be Western centric and assume our culture is all that matters.
Phuket A Dream Come True
P and I were connected at the hip for the first few days in Bangkok. When it was time to fly to Phuket I just didn’t want to go without her. I had heard someone say that bringing a woman to Phuket was like ‘bringing your own sunscreen to the beach’ but I was so comfortable and elated with P that I asked her anyway and she accepted. The next five days were a dream come true. We traveled the island and went to Koh Phi Phi and Maya Bay. We also saw the Majestic Big Buddha and saw many more attractions. Being from Laos P said she didn’t often have the opportunity to swim in the ocean. Neither of us wanted to leave. It was one of those times you wish time could stand still.
We flew back to Bangkok the day before I was to return to the U.S. It was a sad time for both of us. She had begun trying to tell me she had feelings for me but having limited English she could only say ‘I love you too much.’ She asked several times if I could return in six months to which I replied ‘I will try’ along with the necessary conditions and variables. I’m not sure if all that translated and I’m afraid I might have misled her.
Some may think that this was simply a run of the mill scam pulled by massage workers. This possibility was never fully out of my mind during the trip. However after paying her for her massage the first night she refused to take any money from me. She didn’t ask for anything upon leaving. She didn’t give me any information on how I could send her money or ask if I could help support her family. I half expected to get a story about a sick water buffalo or an accident causing an urgent need for medical expenses. I suppose time will tell.
I know it’s impossible for me to be completely objective about the situation but I couldn’t help but feel sincerity in P. Being an Asian ladyboy and massage worker finding a nice Western guy to settle down with could be an ideal goal for her and many in her situation. I’ve personally known fully transitioned trans people who live with the insecurity about their looks and the fears that they will ever be fully accepted. In one interview a trans woman said ‘No one loves a trans woman.’ I met a ladyboy 25 years ago who voiced the same sentiment to me saying ‘A lot of guys want me to be their bit on the side but no one wants to take me seriously and settle down with me.’
In my practice I have several transgender teenagers. Some of their parents and families are supportive but many are not. I suppose my biggest surprise of the trip was that I developed feelings for and fell in love with a ladyboy. When I was arranging for a flight to Phuket I noticed her passport still said ‘male.’ This was a wake up call. I thought ‘Am I in a same sex relationship?’ Although she was born and was still a biological male everything about her was a woman. She was truly a ‘her.’ While the battle still rages in America and I usually find myself on the conservative side personal experience has caused me to reevaluate my assumptions and opinions.
Since I’ve been back P video calls me twice a day and I’m still as fond of her as I was on holiday. I tentatively planned to return in June. So I’m not sure how this story will end. I suppose time will tell.
Story Three A Journey Through Relationships And a Life Changed
This story has its beginnings in 2017 when I visited Thailand for two weeks and I enjoyed myself one week in Chiang Mai and one week in Bangkok. Before I arrived I struck up a few conversations with women online. One of the women I met online picked me up at the airport and we hung out together for the day with me paying for everything massages and a nice lunch. She had a medical procedure the next day and she said something about wanting to see me although I never heard from her again.
So I got on Tinder and I found a cute woman that worked in the courts system and we enjoyed aerobics a lot although she did things to me that no one has ever done before if you know what I mean. Unfortunately we had to communicate via Google Translate which got tiring.
Charm Warning Signs
Finally I connected with another one of the online women named Charm. Although we only met for a few times we hit it off right away because she spoke good English and seemed familiar with Western customs which will make more sense later. I ended up flying Charm down from Chiang Mai to stay with me in Bangkok. She had worked in a hotel in Bangkok many years and knew the area well. We finally got to know each other in the biblical sense and had fun in my hotel on Sukhumvit Soi 11. Although she was older 44 she was very cute and playful. She was used to getting her own way having had an older American husband who passed away and left her with a son and enough money to buy a farm and home in Chiang Mai.
She had been a real looker in her early twenties and was used to getting whatever she wanted. After her husband died she hooked up with another American and he invested with her in a big new house that he is still paying for even though he doesn’t live there any longer.
When I returned later the same year in August and September for three weeks she met me in Phuket for a week of fun aerobics and touristy things then flew back to her home in Chiang Mai where we traveled around the area with overnight excursions. Her ex knew about me and was hoping that I would take over the expenses as he was only living on a dwindling pension and Social Security. I realized after those three weeks that she was used to a higher standard of traveling than I had been. Up until that point I had booked a hotel Best Western on the beach but she complained. She said she had ‘hi so’ friends and wanted that life as well. That was warning sign number one.
Number two was that she still had guys on online dating sites that she talked to as these were her ‘friends.’ When I suggested that she ended these relationships she got defensive and claimed they were only friends. Number three when we went out to eat she would order enough food for four or five people instead of just the two of us. When I objected she then said that she would pay. Even after that I flew to Hong Kong for my birthday and a few days of fun before I left to travel back home she complained that the hotel room we stayed at was small which was true but being Hong Kong it was still very expensive.
I was making plans to come back for three or four months to study Thai travel and see if I wanted to live there. This trip was going to be in February so I had a lot of things to prepare for with my business and my house to dispose of. During that time we were discussing living arrangements. She wanted to pay back the money that the American boyfriend had invested in her home which I thought was great but I think she wanted me to buy him out instead of selling it since she wanted to leave the house to her son. She wasn’t agreeable to that and it was becoming clear she wanted me to pick up the tab for everything house and car payments.
Since her son had an American passport he was eligible for traveling to the USA and wanted me to host him in December to show him around and even help him pay for his ticket. When I said that I did not have the time nor the budget as I was moving and busy with wrapping up work and putting a lot of stuff in storage she said that she had already told him and now he would be disappointed. She’d never asked me before. She told him that I was pissed off and was feeling used and manipulated. Then I remembered that she had warned me that her children would always come first before me.
Ending Things With Charm
I had suggested that we could sell her home and together with what I had we could travel and live almost anywhere without worry by the way I don’t blame the young man he was a good guy and just trying to please his mum. She then said that her home would go to her children and that I should continue to pay her expenses for the home car and buy her a new home on the beach somewhere. I finally woke up to the fact that I was only being used for one thing. Well that was the end of it for me. I told her that I wouldn’t be living in Chiang Mai but Bangkok. I believe that she got the picture but still held out that she could save the relationship. After some calls and tears I finally said goodbye and went on my way to Bangkok.
Not the end yet but I will get to that later. I was sad but looking back I really dodged a situation that would have ended badly for me a me out of money.
Apple and the Daughter
Well it didn’t take long for her to help me get a room around the Thong Lo area. Then I got enrolled in a language class which meant a walk and then a commute on the BTS. Depending on the time I left early in the morning before 7 AM and traveled between 20 to 30 minutes. I should have only rented for a week instead of a month but I was moving too fast and should have taken more time. However it worked out okay as I got to see that part of Bangkok. I then found a short term one bedroom condo rental for the balance of the time I would be staying for the same price as a single room. This place had a small gym and a nice pool. The location was an easy six minute walk to the class that was three hours a day.
This was close to the BTS which is located in the Silom/Sathon area and turned out to be great not as crowded as the other area but still close to the action if I wanted it.
I was now getting assimilated into the culture. With Apple I was introduced to her seven year old daughter a similar story of abuse by the husband and Apple was divorced soon before her daughter was born so he wasn’t on the birth certificate. Nice kid but way too hyperactive and had to be medicated. She worked in the area and kept close tabs on me and I was dependent on her like a fish out of water. As we spent more time her daughter began to grow on me and we soon became attached. I had never had children so this was a new experience for me. I continued to take Thai lessons and became more able to get around and enjoy the culture and sights.
I found a business in Chiang Mai that I thought I could invest in and get a work permit and some cash flow. It was with an English guy who had an impressive operation and was growing fruit food and shrimp. After much discussion Apple and I flew up to Chiang Mai to see the operation while staying at a hotel. We were seen by my other lady friend from the past called Charm and after we got into the guy’s truck to go to visit his operation I got a nasty text from her it was full of venom and hate. So I deleted it and blocked further contact.
Once it was confirmed that I had avoided an unpleasant relationship I can’t stress enough that it is important to take your time and not jump into the first or even second relationship until you get solid with who you are and what you are looking for. It is very easy and tempting to fall for someone right away because of the attention from a much younger woman than we are used to.
So I managed to visit with some women for short time fun. I had been reading a blog from a guy that bragged about how little he could get away with without paying. So when I tried that I got disappointed looks until I realized that this guy was cheap and that the women expected more than a night out on the town with dinner and breakfast. It is different if you are in a long term relationship but you end up paying in other ways. I was getting a real education in life here in Bangkok and like a sponge I was soaking up the information new culture and language all at once and at a rapid pace.
Planning a Life in Thailand
Apple had now gotten used to staying at my place during the week as it was a short walk to her job so that was becoming a thing which I now know was limiting my exposure to other relationships and opportunities. At some point I was introduced to her daughter and thereby began the bonding process. Little did I know that I would be taking a drastic turn into an interesting change of life. I returned to the USA and decided that was it so made long term plans to return get a retirement visa and make life in Thailand.
A Life Changed
I returned a few months later and found a real nice two bedroom apartment for 1200 US dollars a month that I thought would be nice for friends to visit and for Apple to stay on occasion. Well that was a plan and it worked for a while but soon her daughter began calling me ‘Papa’ and we became closer and I wasn’t complaining. Her daughter had emotional and development issues which were being treated medically from a young age. At this point a normal person would have run away but for some reason I didn’t. I soon realized that the public education system in Thailand is lacking in quality with the average class size over 30 plus kids. The school she was at didn’t have a special needs qualified program. She was being held back and ignored.
So I found a private school that had a special needs headmaster and enrolled her in an English based program that she is thriving at. After four years she can now speak very good English and now has the self confidence to succeed in life.
I now travel between the US part time and Bangkok where we live together. I’m also traveling more to different countries and making more friends. I know enough Thai to get around but I’ll never be able to hold an in depth conversation. So for now life is good with enough choices to do whatever I want. I know that I am making a difference in someone’s life that had limited possibilities before. I have reduced my housing budget to accommodate my traveling allowance so most of the expenses here are rent food and education. Apple is working and taking care of her parents on her own and I am free to travel and enjoy life. I have been to various countries and will be going to the Philippines next. I haven’t found the perfect place to settle down permanently yet but I am working on it.
The main takeaway is to not rush things and be picky for what you are looking for. I don’t regret most of my choices but it would have been interesting to have gone in another direction but ‘the grass is always greener’ comes to mind.
