How much of a must is it for you to assfuck your ladyboy picks ?

[Rom]

This thread was inspired by one of our Board’s most butterflying BMs who routinely posts that some of the ladyboys he features in his updates and TRs were “too tight” for sodomizing, some to the point that he does “not even attempt it” and pursues instead other forms of sexual pleasure with them.  It’s a matter-of-factly admission not many BMs are prone to make, including myself.

But I think it’s something we all encounter sooner or later, especially later when age takes its toll on our testosterone levels.  All my life when confronted with a tight asshole (especially butt-virgin GGs) I just redoubled my lubing and probing efforts and skillfully used my hands to drive the tip in, followed by the whole enchilada as they contort themselves in pain.  With the invention of Viagra, I also started planning ahead by taking one that guaranteed I’d be rock hard when the time came to let it rip.  Such reassurance was all the more important because 90%+ of my first times with new partners I used condoms, which require even greater firmness for the initial insertion.

But with age and perhaps habituation, the Viagra no longer guarantees me the rock hardness as it did 20 years ago, and even if it gets me there it will take longer and I may rush into premature attempts at insertion that may lead to the “too tight” pretext to just try something else.

The other thing age has changed for me, is that once inside there I may not be able to achieve orgasm with the condom on … while the anus ring is pleasurably tight as a vice, once past it there is not as much lateral friction in the rectum as there is on the walls of a vagina.  So what is happening more and more often with me is that I may lose the erection (and interest) before orgasm and just stop the pummeling, or I fake orgasm in the condom to get it over with.

This thread is not to induce anyone to post about their limitations, but rather to ask how important it is for you to fuck the ladyboy’s ass when you are with one .  To me it used to be paramount and default.  And if I barfine one, it still is.   But when they latch on to me for days at a time I don’t have that sense of urgency and find myself favoring unprotected oral sex.  On my last trip I had one begging me to fuck her and wondering why I showed no interest in fucking her 3 or 4 times a day like when we first met…

[RHH33]

Do I admit the same issue with a lack of hardness?  Nah, I'll just like Rom's post...

[Dan Miller]

I do think it's the first time I inspired someone to a interesting topic, hahaha. Well done @Rom.

As you might have noted, for me it's really not a 'must' to be able to ass fuck my date. Despite my age I'm still blessed with good hardness, but I care too much for the girls to hurt them, and I simply refuse spending too much time on 'preparing' them 

Especially for some of the youngsters, relatively new in the business, a finger can sometimes even be challenging. In that case, knowing the size of my dick compared to my fingers, I draw the conclusion pretty fast. But like you mention, many other ways to continue the rumble, some might even be more porny and sexy than the ass fuck 

But curious to know if other BMs share my view on this 

[cobber32]

Age has changed my outlook on this - not only the getting hard (or not) but also really wanting to enjoy the moment. Do whatever we both feel like at the time. To focus just on fucking her is no longer my plan. Even cumming, or not, is secondary to enjoying. It's my money and my time. I've said before; life is short, so enjoy.

[Rom]

12 hours ago, Dan Miller said:

I do think it's the first time I inspired someone to a interesting topic, hahaha. Well done @Rom.

As you might have noted, for me it's really not a 'must' to be able to ass fuck my date. Despite my age I'm still blessed with good hardness, but I care too much for the girls to hurt them, and I simply refuse spending too much time on 'preparing' them 

Especially for some of the youngsters, relatively new in the business, a finger can sometimes even be challenging. In that case, knowing the size of my dick compared to my fingers, I draw the conclusion pretty fast. But like you mention, many other ways to continue the rumble, some might even be more porny and sexy than the ass fuck 

But curious to know if other BMs share my view on this 

Hi Dan, thanks for your candour.  You just posted in your ongoing TR that last night (?) you barfined Why Not?'s Zammy (you call her Sammy) which is an excellent choice I have  partaken myself last year on 2 occasions and prior to that (and covid) for horsing around at Baby Boom.  I am curious to hear if you fucked Zammy in the ass ? and if not, how did you 2 take your pleasure instead ?  and I'd rather ask it here than in your TR (because of the pic below) but you may answer in there if you prefer, or not answer at all of course.

With me Zammy tried to get a waiver saying I was too big, but I insisted and despite her reluctance I managed to stuff it in AS PHOTO-DOCUMENTED in the TR I posted to this board.  But with that reluctance, she did achieve me not attempting it again in the morning, as I did not want to push my luck and risk a flat out refusal or a hostile parting ...

This to say that PICTURE TAKING is a big part of the sexual satisfaction I get from my encounters.  In fact it's one of the reasons I get distracted during sex instead of focusing on pumping to orgasm, I start thinking about making my move to take the pics and then the actual picture taking, which detract from the sex itself.  But a good 5 or 6 pics that I can revisit the rest of my life have become more important to me than the orgasm I will forget a few minutes later.  With GG P4Ps,  I also find myself going straight to anal and I usually get my way if i do with confidence and insertion skill, while with farang women my age I dare not take such liberties on first fucks, especially the photos taking which is a red line for them.

While we wait for more BMs to share their mind sets, heeeeeere's Zammy:

[Pulci Gorgon]

Before answering your question, I'd like to point out that you developped a side topic explaining that you don't feel as sexually performant as before with age but you don't want to deal with it. 

So, back to the question of ass fucking a ladyboy, the answer should be very simple. When I asked her before going "do you like bum bum" and she answers "yes", well, we go for bum bum. 
I had exceptions. The first one was my first ladyboy I had invited for a LT. After a few days, many adventures and twists and turns, we were both sick in Chiang Mai. I had noticed she would hardly stand being ass fucked. However, as I needed to go out to look for a pharmacy, she required to have sex with me before I go out. She would pretend I stinked and ordered we have shower together then would perform a great BJ thrice or 4 times a day.  ( I discovered 2 years later the neigbourhood was full of ladyboys and she feared me to put an end to our agreement). 

I had the problem of meeting too tight ladyboys a few times during a trip. 2 of them tried their best during 1 hour in the room but wouldn't manage. I had the feeling they missed experience and also failed since they feared something or were stressed by the situation. I wished they had proposed something else to compensate again and again, but they didn't. 

I remember a   prosti statuesque beauty who pretended to be the best in the city to make me pay her a short time. Once in the room, she started complaining about my dick that would be too big for her (LOL). I managed   to put her on her 4 and screw her. I made sure I didn't injure her since she was screaming but had a somewhat sadistic pleasure in shagging her and listening to her screaming. This is how I sometimes like to treat a bad  b... . 

[Dan Miller]

Haha ... well Rom, unlike some of the others, Sammy can handle probably any cock around. At least a girl with her experience should! So for sure I enjoyed her ass   (And before you ask later, yesss, Pookies too ).

Regarding the photos, I do agree it being part of the 'ritual'. But, like you notice in my TR, I prefer to take more 'SFW' pics than you do. And even when taking naughtier ones, I only post them with explicit approval of the girls themselves. Mostly take some pics before the rumble, before I ruin their make-up 

[Hard1]

On 9/2/2023 at 6:37 AM, Dan Miller said:

Haha ... well Rom, unlike some of the others, Sammy can handle probably any cock around. At least a girl with her experience should! So for sure I enjoyed her ass   (And before you ask later, yesss, Pookies too ).

Regarding the photos, I do agree it being part of the 'ritual'. But, like you notice in my TR, I prefer to take more 'SFW' pics than you do. And even when taking naughtier ones, I only post them with explicit approval of the girls themselves. Mostly take some pics before the rumble, before I ruin their make-up 

I can assure that Sammy could handle any cock also at the Baby Boom's time, when still Silicone-free 

[barforth]

For me it's paramount to top the lb, so I have to do due diligence before bar fining or a TF meet as I am above average in girth and I don't use condoms as I hate them and can't cum with em. This obviously limits my choice but usually ensures mutual satisfaction.

I suppose because of age I've lost some sensitivity so most BJ's don't do much for me and hj's forget the way they yank it up and down.

I concur that with anal there can be a lack of necessary friction but for me I always end in the spoon position where 9/10 times strangely I get more feeling and can cum.

[Rom]

3 minutes ago, barforth said:

For me it's paramount to top the lb, so I have to do due diligence before bar fining or a TF meet as I am above average in girth and I don't use condoms as I hate them and can't cum with em. This obviously limits my choice but usually ensures mutual satisfaction.

I suppose because of age I've lost some sensitivity so most BJ's don't do much for me and hj's forget the way they yank it up and down.

I concur that with anal there can be a lack of necessary friction but for me I always end in the spoon position where 9/10 times strangely I get more feeling and can cum.

Your self-description applies to my own situation EXCEPT the part about not using condoms.  I always use them with ladyboys or GGs I assess to be prostitutes and sometimes I take my chances with some I know are not because they have a job, go to school, live with their parents, show me HIV- tests, etc... but even in those cases I refrain from pumping as hard as I might need to achieve orgasm because it may result in blood which is the riskiest exposure.   To me it remains paramount to top as a matter of principle.  But it is no longer a matter of orgasm.

[barforth]

4 minutes ago, Rom said:

Your self-description applies to my own situation EXCEPT the part about not using condoms.  I always use them with ladyboys or GGs I assess to be prostitutes and sometimes I take my chances with some I know are not because they have a job, go to school, live with their parents, show me HIV- tests, etc... but even in those cases I refrain from pumping as hard as I might need to achieve orgasm because it may result in blood which is the riskiest exposure.   To me it remains paramount to top as a matter of principle.  But it is no longer a matter of orgasm.

Now that I reside in Pattaya I take Prep, yes I'm aware that there is an increased risk in contracting other std's but in my 6 years of residence it hasn't been a problem.

[Pulci Gorgon]

PREP is a highly efficacious protection if you take it seriously. I was told in the hospital  it has an efficacy close to 100% when taken continuously. BUT, I still use condoms since PREP doesn't protect against other STDs and many of them recovered since people use PREP and stopped using condoms. 

[PayingPiper]

I also found I can easily cum in the spoon position. I get into the lady's ass and put a hand on her hip. Then I masturbate her anus on my dick. I get a powerful orgasm in a short time. 

When I go for a long time I often can't cum or I deflate and can't cum.