My Ladyboy Mate

My Ladyboy Mate

Sex Tourists Not Welcome Here, read a large sign in the foyer of my Bangkok hotel. It was slightly off-putting, as in the back of my head, that sprawling, sex-craved metropolis was just the place to tick another item off my bucket list. As a conscious and open-minded guy, I struggled to attach the term “sex tourist” to my own persona.

Am I a sex tourist? I guess all types of horny arseholes somehow justify what they are doing as okay. After a lifetime of marriages and kids and heterosexual relationships, I just wanted to explore my sexuality.

I was in Thailand as part of a much larger solo trek through South East Asia. Though, I was there. In Bangkok. Looking for a ladyboy.

As I sat in my hotel room pondering my intent, I battled to find clarity. I don’t have any issues with the sex industry as a whole, but am well aware of the many parts of it that are completely exploitative and fucked up. To reconcile the conflicts of interest, I reached a personal compromise. I would not attend the sleazy street bars where old white men sat smoking, drinking and revelling in the lacklustre attentions of middle-aged Thai prostitutes. No, I was not that type of guy! Instead, I would look for a higher quality sex worker where business was conducted on a more professional and transparent level.

Was I simply attempting to do the wrong thing better?  Maybe.

As I sat in gridlocked traffic going nowhere, I had every reason in the world to talk myself out of the adventure I had just set out on. My mind flashed back to when I was 24, living in Sydney and suicidal. I decided the world was too big for me and that leaping from the 1000 Steps at the top of the Blue Mountains would be the best way to fly and ease the pain. I got in my car and headed west. 10 minutes up Parramatta road and I hit a roadblock. I sat behind my steering wheel wondering what the fuck I was doing. I did a U-turn and headed back to the pub. Being stationery, as I discovered that night, can be a grand leveller.

As my taxi driver dropped off yet another sex-starved, over ambitious and under achieving farang at the parlour doorstep, I panicked and walked across the road in the opposite direction. My nerves were wrecked as I watched the ladyboys (ka-tois) from across the road. Something I had always wanted was there in front of me, but I froze. It’s one thing being able to get up on stage or ooze confidence in one’s own cultural context, but to face up to a famous Thai ladyboy and ask them how much it costs to suck their cock and fuck them up the arse is something else altogether.

I sank another beer and walked across the road to the parlour. The dude I had my eye on was immense. Tall, straight, buxom and with a classic, sexy, late 50s Sophia Loren-type persona. The hair was huge, the eyelashes epic, the blue tight-sequined dress was lavish and the thought of what lay underneath it captivating.

It was now or never.

“Massage?” she asked.
“Sure,” I said. “What else do you do?”
“You tell me,” was the reply.
“Well … it’s complicated.”

Five minutes later I was following Sammy up a tight set of steps to a room which I paid $10AUD for. It had a grim-looking single mattress and a half-arsed ceiling fan. The haggling wasn’t easy. Broken English, broken nerves and mild anxiety all contributed negatively. Explaining that no massage was required was the easy bit, but manning up and asking her if the suck and fuck were on the menu, and how much it cost, was something more surreal. They must get it all the time, but for each one of us sad sacks chasing the Short Time option in a strange land, it’s back to the drawing board.

She wanted 3000 Thai Baht for an hour, and I immediately went lower. Partly because I’m a tight motherfucker, and partly because I knew I was, at best, good for half an hour.

“2000,” I said.
S̄ịh̄ạw pị,” (fuck off) was the reply.

We settled for 2500THB (90AUD).

Once inside, nervous formalities were undertaken and the obligatory shower scene unfolded. I asked if I could undress her before she got in the shower. It was then that I realised exactly what I had just paid for. She was divine. Curved, smooth and an arse to die for. However, the best was kept till last, as I turned her around to reveal a semi hard 8-inch cock that was mine for the next half hour.

As the nerves were swept away by a mixture of raw sexual energy, lust for life and half a Viagra, the fun began. She was communicative and easy to get along with. I could do what I wanted and I didn’t exploit that fact. I managed to accomplish all the fantasies I had been masturbating over for many years. Some of the hour was a little awkward, especially the part where I misjudged how tight an anus is to fuck. It took all my best efforts to enter and enjoy. Other moments were really funny (some of the condoms she pulled out were more like shopping bags), but overall, the experience was fantastic. She showered me clean at the end and let me put her underwear back on for her.

The ladyboy experience is not for everyone. Even a few of my closest friends couldn’t get past the, “You gotta be fucking joking, brah.” But if you have a thing for gorgeous women and a flickering penchant for a bit of cock action and adventure, then the result can be mind-blowing.

As we walked out of the hotel foyer and back onto the seedy dimly lit back streets of Bangkok central, she looked across at me and gave me a little wink as if to say thank you.

Immediately after that brief but lovely act of closure, I went one way and she the other.

Cover by Paul Kondritz