I would like to be a Ladyboy Bottom but can't

[malibu515]

Several times since I have been coming to Thailand, I have tried to be a bottom. It is a fantasy of mine, to be dominated by a big, mature, shemale and have her fuck me bareback to orgasm. But everytime it has been tried, sometimes with a ladyboy with a small but firm member (with a condom for now) just putting a finger up my ass was terribly painful. Then when they tried to put their penis in me, ever so slowly, it was too uncomfortable and I had to stop. I liked the attitude of the pushy shemales strutting on soi 6/1.
I recently had my enlarged prostate removed by a Trans Urethral Prostatectomy. I had been taking Flo Max before this which made getting a erection difficult, and made me weak, physically. It also reduced my libido significantly. I am now 70 years old. Now that I don't take this medication anymore, I can easily get an erection. Every third day or so, I can jack off to a strong, but dry ,orgasm.
I am waiting for Thailand and the Philippines to open up again but don't know if I dare try coming back again. My desire to fulfill my fantasy, with a big, strong mature shemale having buried her cock balls deep in side of me, is strong.
The additional problem is buying sex toys in Thailand, such as an expander, sized smooth dildos, and other aids. I would also need a topical anaesthetic to try..
Advise is appreciated.
Provided are some photos of the the strong, assertive, mature ladyboys that interest me.

[Rockheart]

There is no problem bringing a few sextoys to Thailand. Plus you are best to use them on yourself some before you go for the real thing, then you control the tempo that you can prepare yourself. Get some very thin short dildos and some progressively bigger ones. Silicone based lube is the slipperiest stuff out there which is good for a starter. I don't really like the silicone lubes for actual sex since they are too slippery and sometime remove sensation, however for a beginner probably worth it.

I have found having some drinks is very helpful in loosening up. Poppers (Rush etc.) really help loosen up the sphincter muscles, however I don't think you can bring or get them in Thailand. However in your home country you if you can buy Poppers then they would be helpful to train yourself just don't mix them with viagra.

As far as partners go, start small and work your way up.
Thailand has lots of smaller hung ladyboys all the way up to huge cocks, so it is good country to start in.
Taking testosterone supplements, viagra and anything to make you more horny ultimately makes it easier too.
Have them use a small toy on you to get you lubed up all the way in and loosen you a bit before they top you.

Once you get used to it, bigger isn't so much problem although you still need to go slow.
I wouldn't really recommend an anethesetic other than alcohol because pain is there for a reason, you don't want to hurt yourself.
At an older age your tissue may not be as strong supple and may tear easier so the pain is there to guide you.

[Escierto]

There is no problem bringing a few sextoys to Thailand. Plus you are best to use them on yourself some before you go for the real thing, then you control the tempo that you can prepare yourself. Get some very thin short dildos and some progressively bigger ones. Silicone based lube is the slipperiest stuff out there which is good for a starter. I don't really like the silicone lubes for actual sex since they are too slippery and sometime remove sensation, however for a beginner probably worth it.

I have found having some drinks is very helpful in loosening up. Poppers (Rush etc.) really help loosen up the sphincter muscles, however I don't think you can bring or get them in Thailand. However in your home country you if you can buy Poppers then they would be helpful to train yourself just don't mix them with viagra.

As far as partners go, start small and work your way up.
Thailand has lots of smaller hung ladyboys all the way up to huge cocks, so it is good country to start in.
Taking testosterone supplements, viagra and anything to make you more horny ultimately makes it easier too.
Have them use a small toy on you to get you lubed up all the way in and loosen you a bit before they top you.

Once you get used to it, bigger isn't so much problem although you still need to go slow.
I wouldn't really recommend an anethesetic other than alcohol because pain is there for a reason, you don't want to hurt yourself.
At an older age your tissue may not be as strong supple and may tear easier so the pain is there to guide you.

Good advice. It’s all about practice, young man, and getting your sphincter muscle accustomed to inbound traffic.