
#7 – Overland Travel
OK Dave, I think I have a particularly unoriginal dare that will nonetheless get you out of your comfort zone! When you get there, I dare you to get your picture taken with one of Thailand’s finest ladyboys
And no cheating – we need evidence of a prominent Adam’s apple and manly hands! (As you know, get someone reliable to take it for you don’t want anyone running off with your camera!)
Since you will need to get your running shoes on shortly after the pic has been taken – straight to a chemical shower no doubt – I will stick the amount at $50 which should get you a reasonably decent hotel in Thailand for a night.
Enjoy! ![]()
Reward: $50 (to go toward a nice night in a Thai hotel)
Status: Completed
___________________________________
I’d been seeing ladyboys everywhere I went since arriving in Thailand – Th Khao San road in Bangkok, Koh Samui, the Full Moon Party on Koh Phangan.
In the throes of an unexpectedly fun first night on Thong Nai Pan Noi, I took a few minutes to have this photo snapped with what in my best judgment (at the time) were 3 ladyboys. Note the light handhold to try and show off “manly” hands.
This photo still makes me shudder.

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18 Comments
Dave this looks so cute! You holding hands with the ladyboy of your dreams haha! Well done on your dare! Btw, your photos of the Thai islands and parties are making me VERY jealous and really make me wanna go back there… Hope you’re having an awesome time!
Dave this looks so cute! You holding hands with the ladyboy of your dreams haha! Well done on your dare! Btw, your photos of the Thai islands and parties are making me VERY jealous and really make me wanna go back there… Hope you’re having an awesome time!
Awwww how cute :shock: Dave I’m so glad you found that special someone!!!! Ha Good dare great laugh for a Monday morning some fine pictures as well travel safe..
Awwww how cute :shock: Dave I’m so glad you found that special someone!!!! Ha Good dare great laugh for a Monday morning some fine pictures as well travel safe..
Dave… Your dares never cease to amaze me! Congrats!
Dave… Your dares never cease to amaze me! Congrats!
Good on ya Dave!!!
you got more Balls than me… uhhh, guts than me!
Good on ya Dave!!!
you got more Balls than me… uhhh, guts than me!
Nice pic :p Love the dare idea. My aunt showed me her Thailand pics a while ago and I was super-impressed by how convincing they can be when dressed up. I was -unable- to tell whether a person was male or female in some of the cases.
It’s certainly a strange phenomenon here. I’m all for people doing what makes them happy, I just think it’s wrong if they’re being deceitful to land customers (not that I think all ladyboys are working girls…er guys).
Nice pic :p Love the dare idea. My aunt showed me her Thailand pics a while ago and I was super-impressed by how convincing they can be when dressed up. I was -unable- to tell whether a person was male or female in some of the cases.
It’s certainly a strange phenomenon here. I’m all for people doing what makes them happy, I just think it’s wrong if they’re being deceitful to land customers (not that I think all ladyboys are working girls…er guys).
That’s a classic, Dave – good work! I’ve just donated your “danger money” ;) Hope you can put it towards a nice hotel…
Safe travels, Steve
That’s a classic, Dave – good work! I’ve just donated your “danger money” ;) Hope you can put it towards a nice hotel…
Safe travels, Steve
Thats my sister Dave!
Love the site; keep it up!
A dare will shortly be arriving for you…
Thats my sister Dave!
Love the site; keep it up!
A dare will shortly be arriving for you…
what should I say? These guys look like guys.
ladyboy
18 Comments