In the Horns of a Dilemma

[Rom]

This post is an attempt at livening things up here in the Board, so please opine even if the topic (my sex life) is not of much interest to you.  Here is my Horny Dilemma:

- I got a small paid gig in the PH in September and am traveling ahead to spend a week or 2 in TH first.

- I am definitely first going straight to Pattaya where I spent almost 3 weeks 2 months ago.

- As TRed, that trip was a sissy mongering success quantity and qualitywise but none of them latched on.

- Since I got back to Europe only 2 of those June fucks kept in touch with me.  They are:

#1.  Fang who is objectively the most beautiful sissy I am aware of currently selling his ass in TH.  It's really me who has strived to stay in contact with her.  She is polite enough to answer me but once it became clear I wasn t sending any money the nude videocalls stopped.  If I catch her at the bar I think it will not be a problem to barfine her and ST her at market rates and perhaps LT her at an overnight premium.

#2 - Is a homely 50 yo GG beer bar slut with a fat gut and huge saggers that I STed in the 1 hour interval between 2 Euro 2024 matches.  She blew me and massaged me for most of that hour and at the end she pressed her breasts together and i titfucked her to completion.  I don't remember her name and never thought I'd see her again.

3 -  I must have given her my FB and a few days after our ST she contacted me saying she wanted me to take her anal cherry (maybe she is lying, but a lot of women go through life with their anuses unprobed).  However, when she offered her ass it was already my last night and I had made plans to fuck another premium sissy's ass instead.

4 - 2 weeks or so after I returned she messaged me to say she had quit the bar (and quit being a prosti, or so she said) and that she missed me and wanted to be with me.  I still don't know her name and at this stage am too embarrassed to ask.  She kept calling me and I revealed I was going back to TH soon.  She wants and at this stage ASSUMES she will shack up with me.  She calls me almost every day.

5 -  A couple days ago she confessed me she knew me from like 25 years ago and that I used to fuck her "sister" who used to work with her in one of the former soi Pattayland bars.  I have no recollection of either her or the sister but I used to go a lot to the Pattayalands 1-2 GG bars when I stayed at the Penthouse... Apparently, at the time, I was famous for being a butterfly even greater than I thought I was.

6 - The saggy MILF does not seem to know I fuck boys in frocks...

5 -  So here is my dilemma:

The most beautiful ladyboy in TH         versus        a live-in mature GG anal sex slave.

I confess I am inclined for the GG slave option as I can feel much lust for her imperfect curvy body that I want to use like a a XIX century boss would use his housemaid's and buttfuck her 24/7 til it gapes like a 2 euro coins stacker.

On the other hand: Fang is the most beautiful sissy in TH and she may not give me another chance if she realizes I am passing her for an old fat whore...

This is a ladyboy board, so I expect most BMs would pick the ladyboy, especially since she is the hottest one alive.  But is there anyone who can understand I may pass Fang for 2 baggy tits down to the hips and an old stinky hairy pussy for me to lick???

Thanks in advance for your enlightened opinions...

Party On,

 

Edited August 2 by Rom
sorry cant post their pics. I was already heroed to Fang. And the old sagger would be a bit of a freak show and that's not how I want to cast her.

[Dan Miller]

4 hours ago, Rom said:

This is a ladyboy board, so I expect most BMs would pick the ladyboy, especially since she is the hottest one alive.  But is there anyone who can understand I may pass Fang for 2 baggy tits down to the hips and an old stinky hairy pussy for me to lick???

To be honest: NO !! 

I totally can understand you being tempted to pass Fang for another whore, or a GG, or a freebie. 'Change of food makes you eat' right, or is this just a silly Dutch saying 

But when you describe her as above yourself, i wouldn't copy your choice on any weekday nor in the weekend! Not sure what I dislike more, the old, the hairy or the smelly ... but the combination is a No-Go  

[Rom]

thanks Dan.  I dont think I described the old GG prosti  in a way that elevates her "above" myself.  On the contrary: I referred to her as a prospective sex SLAVE ("anal sex slave").  It's she who has been the one elevating me by calling me everyday, saying she misses me and remembers me from like the 1990s, and not once asking me to send her money (unlike Fang).  The only part of my words of her possibly being "above" myself is perhaps where I said I'd be licking her pussy, which would be somewhat submissive of me considering her age and homeliness with her fat ungroomed ass sitting on my face...  but that's precisely what attracts me to her is overcoming my reluctance and taking my pleasure with an ugly old one.  I concede there is an element of my submissiveness in this, but hey! she is the one who licked my ass for half an hour after the PL-NL match while I waited for the next one... The thought of me now eventually licking hers both repulses me and challenges me....

Hope this clarifies my mind frame.  There is no question I will be with her again when I go to Pattaya. The question is will I let her latch on to me for more than a night or 2 and forego beautiful sissies who unlike old GGs I cannot avail myself of when I am in Europe...

Thanks for posting.

 

[Dan Miller]

1 hour ago, Rom said:

thanks Dan.  I dont think I described the old GG prosti  in a way that elevates her "above" myself.  On the contrary: I referred to her as a prospective sex SLAVE ("anal sex slave).  It's she who has been the one elevating me by calling me everyday, saying she misses me and remembers me from like the 1990s, and not once asking me to send her money (unlike Fang).  The only part of my words of her possibly being "above" myself is perhaps where I said I'd be licking her pussy, which would be somewhat submissive of me considering her age and homeliness with her fat ungroomed ass sitting on my face...  but that's precisely what attracts me to her is overcoming my reluctance and taking my pleasure with an ugly old one.  I concede there is an element of my submissiveness in this, but hey! she is the one who licked my ass for half an hour after the PL-NL match while I waited for the next one... The thought of me now eventually licking hers both repulses me and challenges me....

Hope this clarifies my mind frame.  There is no question I will be with her again when I go to Pattaya. The question is will I let her latch on to me for more than a night or 2 and forego beautiful sissies who unlike old GGs I cannot avail myself of when I am in Europe...

Thanks for posting.

 

Haha, up to you brother! Age for sure ain't an issue. Some of my best encounters in LoS where not with the youngsters but near, or even above 40. No substitute for experience!

And I get the submissive part, can be so relaxed to just go with the flow and do what you're told to do 

It's like you said: Party On!! 

[RHH33]

3 hours ago, Rom said:

thanks Dan.  I dont think I described the old GG prosti  in a way that elevates her "above" myself.  On the contrary: I referred to her as a prospective sex SLAVE ("anal sex slave").  It's she who has been the one elevating me by calling me everyday, saying she misses me and remembers me from like the 1990s, and not once asking me to send her money (unlike Fang).  The only part of my words of her possibly being "above" myself is perhaps where I said I'd be licking her pussy, which would be somewhat submissive of me considering her age and homeliness with her fat ungroomed ass sitting on my face...  but that's precisely what attracts me to her is overcoming my reluctance and taking my pleasure with an ugly old one.  I concede there is an element of my submissiveness in this, but hey! she is the one who licked my ass for half an hour after the PL-NL match while I waited for the next one... The thought of me now eventually licking hers both repulses me and challenges me....

Hope this clarifies my mind frame.  There is no question I will be with her again when I go to Pattaya. The question is will I let her latch on to me for more than a night or 2 and forego beautiful sissies who unlike old GGs I cannot avail myself of when I am in Europe...

Thanks for posting.

 

Regardless, we will look forward to reading the adventures of Rom!

[Pdoggg]

5 hours ago, Rom said:

s there anyone who can understand I may pass Fang for 2 baggy tits down to the hips and an old stinky hairy pussy for me to lick???

I understand.

It comes down to what you think you should do vs what will make you most comfortable

This "should do" vs. "want to" is what I experienced during my last trip to Angeles.  I felt a strong resistance to heading out to Phillies and dealing with the BS from the ladyboys that hung out around there.  It was so much easier just to make a call to someone I felt comfortable with even though her looks and the the sex was just average.  I knew it would be a hassle free experience.  My general mood was Netflix and chill rather than the pursuit of of new and exciting partners.

There's lots to be said for taking Fang to Miss International Queen.  Perhaps a rush that you're with a ladyboy that's prettier than any of the contestants.   But it seems you're in a mood for a relaxed holiday without the effort involved with pkanning.  A couple of short times with Fang with no pre-planning hassles might be just what the doctor ordered.

I would suggest though that your anal slave fully understands that you are a big butterfly, that you need yur space, and that you don't want your freedom compromised.

 

[Rom]

Thanks @RHH33 for your interest and encouragement and thanks PDoggg you are a wise and kind leader... Let me react to what you reckoned by quoting it:

This "should do" vs. "want to" is [ ... ] so much easier just to make a call to someone I felt comfortable [for] a hassle free experience.

I know what you mean but it's not the case with my saggy tits old bag crush.  I don't see her as hassle free as I will have to keep my guard up, at least initially.  I don't know if she is still affiliated with the Chayapoom bar where we met and would not know where to start if she pulls something on me (I have her FB name and some pics that's all).  I betcha she is now doing Beach Road as a lowest end old whore and I would not look at her twice if I passed by (unless she flashed those saggers down to her knees).  A comfortable experience as you call it would be for me to stick around at Cindy's Secrets 2 where I am known and danmiller 1-by-1 the staff sissies there...

There's lots to be said for taking Fang to Miss International Queen.  Perhaps a rush that you're with a ladyboy that's prettier than any of the contestants.   (...)  A couple of short times with Fang with no pre-planning hassles might be just what the doctor ordered.

Yes Fang is throwing me off my game.  Not because she is so beautiful I get horny for her and the sex is better.  No.  It's because she is so beautiful I just want to be with her and be seen with her and post here how I was with her.  Seriously she is so beautiful it hurts and she is gracious at all times even when she is  ATMing me.

I would suggest though that your anal slave fully understands that you are a big butterfly,

She knows well that I am and keeps mentioning it.  According to her, I am the biggest butterfly she ever saw in her 30 (my guess) years as a prosti.  She is the one remembering and telling me of GG prowesses I committed in the 1990s that even I was not aware I had committed.  According to her I fucked like 20 GGs in the old Classroom bar where she worked (more like 6 or 7!) and I fucked every mamasan in Pattayaland 2 (only 2 and one was a sissy and I wonder if she is aware of that and of my fondness for sissy cock).   Allegedly I fucked her "sister" although I don't know if she means a blood sister or a closer friend of hers.  If she hadn't mentioned a very personal detail that happened with one of the Penthouse GGs and that I never talk about, I would think it's a case of mistaken identity or flattery with a view to gaining my barfine money... 

...  that you need your space, and that you don't want your freedom compromised.

It's not clear yet to me she wants to latch on for the duration. Honestly I don't know what exactly she wants from me.  All the stuff she says about me indicates that she knows I am a seasoned monger, thus unlikely to be milked by an old prosti... Perhaps she can tell I am a good heart.  Or maybe it's my fat cock which she has gagged on already and invited to bust her ass... 

I will keep you posted... In the meantime just a few hours ago the plot thickened with another former bargirl GG (this one a gorgeous MILF in her 30s) vying to stay with me.  I will tell about it in a forthcoming post...

Fang hasn't buzzed me in 2 weeks and probably does not plan to. 

Party on.

R

[Pulci Gorgon]

Strange question and dilemma posed by such an experienced member. You  ( @Rom ) 've mongered both GGs and ladyboys for decades, so you know better than we do what you like. If you ask us what you should choose, anyone will answer based on what they like, not what you like. In another time, on another forum, I might have commented that this is 'a wind-up,' but you're not a newbie asking such a question.

The point for anyone is to analyze and understand why they have always visited Thailand and other Asian countries. If one could discuss this subject without risking a clique (not at LBR) gossiping and arguing, one would be surprised to see how basic motivations differ from one BM to another. Therefore, I'm not going to tell you what I would do in your situation. It wouldn't help you. I just hope you make the right choice based on your own tastes.

[Rom]

Thanks PG for the vote of confidence in my mongering proficiency.  Asking BMs for advice is a way of trying to engage them and generating posts that this board could use.  It develops the narrative with an element of uncertainty meant to capture the reader's curiosity and attention.  As you said: it's me who will decide, but I like to listen to other people.  So listen to this:  I have 3 GGs already in play for this trip:

#1 is the abovementioned old bargirl who calls me every day.  She keeps asking which exact day I arrive and says she will stay with me as long as I want and will take it up the ass, which she says she never tried.  She asked me if I am into ladyboys and I said "I tried ladyboy. I like lady" which technically is true. Even though she is in her upper 40s and not particularly attractive, she is so motivated to stay with me that I cant pass her up.  It happens to me a lot in the PH, but not in TH anymore.  On my last trip to Pattaya I fucked like 20 sisses+GGs and none showed interest in latching on.  I welcome this chance to have a 24 hour sex partner for at least a few days.

#2 is a former bargirl I already featured here in one of my TRs.  She is really fun to hang out with and is quite attractive with a body to die for also with big tits but firm ones in her case.  I met her towards the end of a trip and stayed with her through the end even though her barfine was 1000.  Then I met her again on the following trip and we stayed together in BKK.  The she quit the bars as apparently she stroke it rich and was flashing all kinds of big chunky gold bracelets and necklaces on FB.  Perhaps the source of that gold dumped her because she is back in Pattaya (but not in the bars) and wants to hook up with me again.  I can't pass her up.

#3 is a PH GG I have been biding my time to be with her again.  We met 10 years ago when she was 18 and fresh from the farm. She became Ermita's prettiest demi-mondaine and we were together a few times over the next few years.  Her aim was to land a husband but she is too good a person to let herself go for a guy she does not care about so she never ensnared one like the far less attractive pinays manage to.  She quit the prosti life, became a maid and eventually went to live with a poor pinoy guy closer to her age.  I knew it would not last forever and YESTERDAY she messaged me for the first time in like 2 years saying she is going back to her province.  I showed the required sympathy and did not take me long to convince her to meet me on my next trip. I sent her a 1000 pesos to show I care. My plan is to have her join me in Angeles and party with her and the sissies.  We have a precedent from like 7 years ago when we came back plastered to the hotel with a sissy and slept together and she did not mind. I ate her pussy while the sissy blew me.  I look forward to doing it again.

So as you see, this trip is shaping up to be more of a GG fuckfest than sissies'.  I know BMs here are into sissies mostly, but do I have your attention?

[RHH33]

1 hour ago, Rom said:

Thanks PG for the vote of confidence in my mongering proficiency.  Asking BMs for advice is a way of trying to engage them and generating posts that this board could use.  It develops the narrative with an element of uncertainty meant to capture the reader's curiosity and attention.  As you said: it's me who will decide, but I like to listen to other people.  So listen to this:  I have 3 GGs already in play for this trip:

#1 is the abovementioned old bargirl who calls me every day.  She keeps asking which exact day I arrive and says she will stay with me as long as I want and will take it up the ass, which she says she never tried.  She asked me if I am into ladyboys and I said "I tried ladyboy. I like lady" which technically is true. Even though she is in her upper 40s and not particularly attractive, she is so motivated to stay with me that I cant pass her up.  It happens to me a lot in the PH, but not in TH anymore.  On my last trip to Pattaya I fucked like 20 sisses+GGs and none showed interest in latching on.  I welcome this chance to have a 24 hour sex partner for at least a few days.

#2 is a former bargirl I already featured here in one of my TRs.  She is really fun to hang out with and is quite attractive with a body to die for also with big tits but firm ones in her case.  I met her towards the end of a trip and stayed with her through the end even though her barfine was 1000.  Then I met her again on the following trip and we stayed together in BKK.  The she quit the bars as apparently she stroke it rich and was flashing all kinds of big chunky gold bracelets and necklaces on FB.  Perhaps the source of that gold dumped her because she is back in Pattaya (but not in the bars) and wants to hook up with me again.  I can't pass her up.

#3 is a PH GG I have been biding my time to be with her again.  We met 10 years ago when she was 18 and fresh from the farm. She became Ermita's prettiest demi-mondaine and we were together a few times over the next few years.  Her aim was to land a husband but she is too good a person to let herself go for a guy she does not care about so she never ensnared one like the far less attractive pinays manage to.  She quit the prosti life, became a maid and eventually went to live with a poor pinoy guy closer to her age.  I knew it would not last forever and YESTERDAY she messaged me for the first time in like 2 years saying she is going back to her province.  I showed the required sympathy and did not take me long to convince her to meet me on my next trip. I sent her a 1000 pesos to show I care. My plan is to have her join me in Angeles and party with her and the sissies.  We have a precedent from like 7 years ago when we came back plastered to the hotel with a sissy and slept together and she did not mind. I ate her pussy while the sissy blew me.  I look forward to doing it again.

So as you see, this trip is shaping up to be more of a GG fuckfest than sissies'.  I know BMs here are into sissies mostly, but do I have your attention?

I so enjoy living vicariously through Rom!  He exploits are to die for and his writing is superb. "Write on Rom"

[Rom]

So kind of you to post to say that @RHH33.   In a way I am also living vicariously through my posts as if I am already enjoying the things I am going to do with the 3 GGs knowing that, once on the field of play, outcomes will deviate from plans/prognostics and if I nail 2 out of 3 of those GGs it will already be a success in terms of the plan.  Other things will happen on my side or theirs that may make it untimely to meet.  For example if Fang wants to stay with me, all the pussy is out the window...

Thanks also RHH33 for complimenting my writing.  It's the best I can manage not having been born a native-speaker although I studied and worked in the US for 3 decades.

As a thank you to RHH33 I will post pics of the 3 GGs which I was not planning to do until if/when I am with them. Chances of being heroed from this sissy site to any of them are very slim, but you never know and I am not going to risk it, so no faces...

Here are the boobs of bachelorettes #1 (the old TH hoe); #2 (the hot TH MILF); and #3 (the pinay cutie)

 

[ribbitrabbit]

Late to the party here but interesting dilemma there @Rom. At the the risk of appearing to hijack your topic I'm in a similar one myself as I visit BKK next week on a work trip for about 4 days. Got a tight Thai GG milf (who I mentioned toward the end of my June TR) who's been in touch with me and having very engaging conversations without once asking for monies. The other is a LB from CIB who I really liked and we seemed to have some chemistry, and she's asked to spend a day by the riverside where we can "complete fantasies" (in her words). Too many experience, too little time.

So I'm gonna put my butterfly cap on and... squeeze both in. In my limited exp Thais have a way of keeping you engaged online and acting different once you finally meet them after months (that could be just my luck tho). My play's is to get some time with both on the first few days, and then spend a hardcore day/night with whoever I click with better at the time and how i'm generally feeling to be around them in reality (instead of my digital infatuation with how things could be.) That'll probably my advice here too -- see if you can spend some time on the ground and see who's making you feel how then.

On side note - love, love your writing style and how raw and imaginative it feels. If you ever choose to write a book (or a TR compilation) count me in for an autographed pre-order!! 

[Rom]

thanks @ribbitrabbit it's kind of you to show interest and want to pre-order a book I havent written  THANKS ...  By now you are probably on your way to BKK so the wheels are in motion and I hope you nail the GG and the sissy ... if at all possible IN A THREESOME.   That would be the Rom thing to do.  Naturally, the fact that u are on a 4 day business trip may limit your mongering range and picks, especially if you are part of a delegation and want to hide such mongering especially the sissies. So it's smart to have taken care of the courtship PRIOR to the trip and just have them deliver themselves to you at the hotel.  Good luck!  I look forward to your field report and how you managed to monger right under your colleagues' noses...

[Rom]

As I write this post, it's 48 hours to departure and already it looks like the 3-lady plan I outlined above is out the window.  Let me make a quick pre-trip update and afterwards I will TR from the field. 

I am going to taxi straight from the airport to Pattaya and I havent told anyone what day exactly I arrive.  This will leave me 2-3 days to scout and pursue opportunities that may present themselves.

I will arrive mid-afternoon and the first thing I will do is check in with the beautiful Fang.  I think my prospects of connecting with her are limited and we lost messenger touch after I told her I had to delay my trip and would not be in Pattaya in time for the Miss Tiffany Universe, which she wanted to attend with me paying for her and a friend.  While I can just call Fang anytime, my plan is to surprise show up at the bar at night and hope she is there and barfine her on the spot and thus achieve the bare minimum objective of enjoying her intimate company for an hour or 2.  Anything beyond that will depend on Fang herself wanting to be with me, which does not look likely at this stage.

The old huge saggy tits MILF had been calling me everyday, but hasn't for the last 3 days just when I wanted to have closer communication.  I recall that she said she wanted to stay with me the whole time and surrender her anal virginity and if it happened I would be left non-butterfly and sissyless this trip but would compensate with 24-7 butt gaping (hers!).  Maybe it will happen maybe not.  I view it as a challenging opportunity as I wonder also if I will rise to the occasion with such a homely coarse woman.

The other Thai GG that I may or may not hook up with open-ended is the beautiful MILF with big firm tits.  She struck it rich with some eurofool and if she stays with me will be because SHE wants to as she knows I am not going to pay her more.  Problem is we stopped chatting 2 weeks ago and it's not clear to me if she is still in Pattaya.

The 3rd lady is a former pinay fuck who left her husband to go back live in her province.  We had talked about shuttling her to Angels and introduce her to group sex with my sissy groupies.  Unfortunately income opportunities in the province are scarce and after leaving her son there she moved on alone to Manila, where I can only assume she has resumed being a prosti after a 6 year hiatus... I don't think I want to meet her anymore as it was going to be all about the old GF illusion and besides I'd be holding her back from cashing in as I'd never pay her what she can earn with multiple other guys.  It will only happen if we run into each other in Ermita (if she is there she will be informed within minutes of me being spotted there).  If she is renting out her pussy in Makati it's unlikely we will run into each other.

There is now a new Joker card on the table. 2 days ago I was contacted by my steady Pattaya sissy fuck that I featured in a few of my TRs under the name Coca-Cola (because her cock is thick like a Coke can).  She is beautiful, fun and devoted to me and once we hook up she stays on and never counts the money.  The problem is that on our last time together I realized she was too far gone with that substance we cannot talk about in ladyboy boards.  She implored me to take her with me to Europe and, that not being a choice, she moved back to Issaan where she stayed for over a year.  Now she is back in Pattaya in the hair salon where she worked when we met, after which she gradually became a freelancer and a user-dealer of said substance we cannot talk about.  I probably should just leave her to her complicated life and not tell her I am in town but I miss gagging on that thick cock.  I confess that I also care for her enough that I crave the intimacy of being with her open-ended... I just hope I don't casually run into Coca-Cola in Buakhao holding hands with Fang or another of the hot sissies not having told her I am in town.  That would break her heart.

That's all for now folks.  Showtime is next.

Rom

[Dan Miller]

Great way of announcing the plans @Rom

It's now 8.14pm here in BKK and I don't even know where I will go at 9pm