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To bottom or not to bottom?... That is the Question !


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Manliness and bottoming are still seen by many ladyboy mongers as contradictory, which leads some of us to refuse to even consider it (like our most off-the-beaten path BM) or to be ambivalent about it and not enjoy it as often or as thoroughly (like myself).  Of the mongers who enjoy it (the majority of BMs here I suspect) most keep quiet about it, the one exception in our Board being our illustrious fellow BM who was prison-style raped 6 times in one night alternating between the shower and the bed and posts about it every chance he gets.

It's not that I don’t enjoy being penetrated.  I totally love being fingered by the GGs when I missionary top them, or when they are blowing me.  I am also game for strap on bottoming which I view as the price I have to pay for routine anal access into the ladies wearing the straps.  But with the ladyboys it’s case-by-case.  With only a very few it happened spontaneously that they showed eagerness to fuck me.  The rest it never happens unless I propose it, which I only do with repeat partners.  This has mostly to do with their own notions of femininity, which they may put ahead of their sexual pleasure.  If I insist it means I have to choose between having them in the subservient feminine kathoey mode or becoming a bit of a kathoey myself (for Thais "kathoey" has a default strictly passive sex connotation).  I always choose the former for the sake of the overall sex and GFE.

Let me give an example:   3 years ago I met this 18 yo filipino sissy who had never gone past giving blowjobs (or so she said).   On our first time in bed during the foreplay I put my mouth to her cock and she jumped in horror at the thought of role reversal.  I told her to close her eyes and relax, and then I licked a little lower while jerking her off to orgasm.  Then I took her virginity (or so she said).   I became her sex teacher and 2 or 3 sessions later I slid a condom on her cock and sat on it.  She fussed and protested, but took to it like a duck to water and ejaculated in less than 30 seconds once she got me positioned doggystyle.  We did it 4 or 5 more times after that and each time the same reluctance followed by quick intense release. But the fact that she never showed interest led me to stop asking and on my last trip I was with her at least 10 nights (she now has a daytime office job) and she never fucked me once and we were both OK with that.

BMs who are open-minded (and open-assed) enough to post about their bottoming, may want to share how that affects their overall roleplay interaction with the sissies?   Especially those BMs in long term relationships where the intimacy should be there to put sexual pleasure ahead of gender pretense and where the much younger sissy partners presumably rise to the occasion more often than the elderly farang ones … 

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I got jail raped 7 times one night...  not 6 times. I watched my dignity swirl down the shower drain early Sunday afternoon at the Pattaya Hyatt after an entire Saturday night and Sunday morning of being ass pounded.

my last shower was to remove Bukake off my face which was preventing my eyes from opening so it was time to clean up a bit.

 

For me..... I ALWAYS like anal stimulation. Masturbating as a early teen prior to getting with girls...then after losing virginity.... Fingers and tongues with GGs....well before getting into LBs.

But during my time with LBs.... I would have to force myself to actually get topped because I rarely found it comfortable (in comparison to fingers and tongues) and generally find it difficult having a cock pounding my ass in and out. I was just going thru the motions.... eventhough I didnt really find it that fun.

With some tricks LBs have taught me to control breathing and becoming more relaxing I find that getting topped is an interesting and fun aspect with LBs.... currently I try to have 75% of my Trans encounters top me because if I want to exclusively top...  I prefer to top GG Vag. GGVag feels much better for me and I'm not as enthusiastic about banging any ass these days......the size and angle and the condom all tend to make a substandard experience versus vag fucks....IMHO.

 

As I get older, my cock sensitivity and ability to come quickly multiple times in a day has substantially reduced. Getting anal stimulation....which includes the girls licking me, fingering me, using toys and topping me.... allow me to have super super intense orgasms because they combine penis stimulation with anal stimulation that bring me to a totally new level of energy explosion. Its sometimes so crazy I can't move for 10 or 20 minutes after because I am so depleted. My orgasms last 2minutes... 5 minutes....even 10 minutes non stop!!!!  GGs who witness this fear that i may have had a heart attack the orgasim is so intense and part way between my flopping in ecstasy on the bed i have to yelp out "everything is ok"....so they stop feeling i might be dying and calling 911 might be in order.

The enhanced fun is mostly from the combo of penis and anal stimulation with toys and tongues... (versus actually getting topped by a penis).

Basically including my ass as a sexual organ into my encounters has taken what is a declining physical sexual life in my late 50s to become the best its ever been in my life....ever!! More fulfilling than even my 20s and 30s......  my sexual energy, orgasms, comfort with self and absolute satiatation with pleasure every time that leaves me with a glow and great feeling for weeks after, all come with using both of my organs during the act of sex. It's not 1+1 = 2 but more like 1 + 1 = 5. 

My ass has stepped up just at the right time and "buttresses" my prior penis-only sex life to glowing results!

 

 

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thanks The-Sith for posting unabashedly.   And yes it was 7 times Sandy rammed you.  In fact it was me who pointed it out in another thread that you took a 7-0 pounding (same same North Korea owned by Portugal) not 7-1 (Brazil by Germany).

The absence of more BMs posts underscores the whole uneasyness of the topic.   Not many mongers are willing to admit they enjoy bottoming.   It's just how it is.  I hesitate also.  Not only to admit it.  But to enjoy it when I have a chance.

But I have personally witnessed enough mongers who, like The-Sith, enjoy and do it more and more as they get older.  For example, some time ago I mentioned that one of the PY mods has become a frequent crossdresser.  Well I remember distinctly reading in PY 10 years ago that same mod posting how he had bottomed in the course of a casual encounter and did not enjoy it at all and would continue to avoid bending over for sissies.   Well get this:  10 years later, the same Thai sissy source who told me that mod is now a flaming CD also told me he has become the designated pass-around-party-bottom on lingerie pool nights. I also heard stories about one of the star bar owners demanding to be topped by each and every one of his staff (while giving the opposite impression at PY).

Does anyone else agree that there is a positive correlation between age and willingness to be topped?  In my case it is not working out that way but that's not due to increased aversion.  Just that I am not pursuing being porked as part of the sex repertoire.   But I think with the right sissy it might happen more often.

@The-Sith  when Sandy topped you 7 times did he deep kiss you like there was no tomorrow ?   I remember that, after I denied him access to my butt, he forcefully shoved his tongue down my throat in what was otherwise a very transactional ST sex encounter...

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8 hours ago, Rom said:

.

@The-Sith  when Sandy topped you 7 times did he deep kiss you like there was no tomorrow ?   I remember that, after I denied him access to my butt, he forcefully shoved his tongue down my throat in what was otherwise a very transactional ST sex encounter...

are you kidding me?

the minute we laid our eyes on each other the first time...... in Fantasy Lounge around 6pm so it was still daylight outside.... I grabbed her and gave her the deepest most romantic kiss of her life. I held her tight in a way to tell her she was all mine. I bought her a beer and said she would be coming with me all night and morning. And I fed her the most romantic words I could. She melted in my arms......... and became my little kitty Kat (she had the super short tiger hair back then). We deep tongue smooched at the bar for about 30 minutes before going any where else.

I think it was that type of domination that brought out the animal in her. Remember.....for a male/transwoman/nonbinary with a cock to fuck and cum seven times in one night..... something has to induce it. 

I was the one forcefully shoving my tongue down her throat.

 

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thanks The-Sith for your candid testimonies .   It would be interesting to hear also from other BMs but one of the points I tried to make in starting this thread was precisely that bottoming remains somewhat of a stigma for most sissy mongers to admit to, including apparently the LBR mongers.

I will just make this one more post sharing why I don't bottom very often despite enjoying it under the right conditions.  There are 2 main reasons why I don't: (i) shit; and (ii) HIV.   Advance cleaning up in preparation of bottoming is a must and often I feel am not ready and shit may happen as it has with me both topping and bottoming.  The other reason I hold back is that bottoming exponentially potentiates HIV infection and I don't want to risk it even when I know my partners are wearing condoms and tested negative.   As a result if a sissy gets past my sphincter, I will remain tense and alert to make sure his condom stays intact and in place and I don't let myself be swept into that kind of absolute-pleasure-let-it-rip-ecstasy-mode such as described by The-Sith.  In this vein, during my recent trip my main pinay sissy (mentioned above) and I HIV tested together and then I started fucking her bareback, but still did not want her to fuck me despite knowing she tested negative.  She stuck to her passive lady role and did not ask to fuck me and I avoided telling her that if she were to fuck me I would still want her to wear a condom even though I wasnt wearing one on her.  So no fudge packing up my crapper by the sissy I love the most.

Are there any other BMs who pass on bottoming even though they know they might enjoy it ?

 

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13 hours ago, Rom said:

bottoming remains somewhat of a stigma for most sissy mongers to admit to,

13 hours ago, Rom said:

As a result if a sissy gets past my sphincter, I will remain tense and alert

The stigma of bottoming is quite distinct from the reason many don't bottom.  Beyond HIV, STDs, and condom slippage that you describe, I think there is a real fear, not unfounded, that a sissy or ladyboy could perhaps do permanent damage to one's bottom and that is why many won't try or give up after one or two uncomfortable experiments.

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On 9/7/2022 at 1:43 AM, The-Sith said:

I got jail raped 7 times one night...  not 6 times. I watched my dignity swirl down the shower drain early Sunday afternoon at the Pattaya Hyatt after an entire Saturday night and Sunday morning of being ass pounded.

my last shower was to remove Bukake off my face which was preventing my eyes from opening so it was time to clean up a bit.

 

For me..... I ALWAYS like anal stimulation. Masturbating as a early teen prior to getting with girls...then after losing virginity.... Fingers and tongues with GGs....well before getting into LBs.

But during my time with LBs.... I would have to force myself to actually get topped because I rarely found it comfortable (in comparison to fingers and tongues) and generally find it difficult having a cock pounding my ass in and out. I was just going thru the motions.... eventhough I didnt really find it that fun.

With some tricks LBs have taught me to control breathing and becoming more relaxing I find that getting topped is an interesting and fun aspect with LBs.... currently I try to have 75% of my Trans encounters top me because if I want to exclusively top...  I prefer to top GG Vag. GGVag feels much better for me and I'm not as enthusiastic about banging any ass these days......the size and angle and the condom all tend to make a substandard experience versus vag fucks....IMHO.

 

As I get older, my cock sensitivity and ability to come quickly multiple times in a day has substantially reduced. Getting anal stimulation....which includes the girls licking me, fingering me, using toys and topping me.... allow me to have super super intense orgasms because they combine penis stimulation with anal stimulation that bring me to a totally new level of energy explosion. Its sometimes so crazy I can't move for 10 or 20 minutes after because I am so depleted. My orgasms last 2minutes... 5 minutes....even 10 minutes non stop!!!!  GGs who witness this fear that i may have had a heart attack the orgasim is so intense and part way between my flopping in ecstasy on the bed i have to yelp out "everything is ok"....so they stop feeling i might be dying and calling 911 might be in order.

The enhanced fun is mostly from the combo of penis and anal stimulation with toys and tongues... (versus actually getting topped by a penis).

Basically including my ass as a sexual organ into my encounters has taken what is a declining physical sexual life in my late 50s to become the best its ever been in my life....ever!! More fulfilling than even my 20s and 30s......  my sexual energy, orgasms, comfort with self and absolute satiatation with pleasure every time that leaves me with a glow and great feeling for weeks after, all come with using both of my organs during the act of sex. It's not 1+1 = 2 but more like 1 + 1 = 5. 

My ass has stepped up just at the right time and "buttresses" my prior penis-only sex life to glowing results!

 

 

Umm you realize you just gave most of us an epiphany.

Explains a lot of things that have often puzzled us.

Zen and the art of nederlands maintenance - Ryan Millar

Why some mongerers love newer and younger ladyboys..

Answer:

because the young ladyboy cock works perfectly,

you're a bottom and have becoming better at bottoming and

you'd rather not waste time and money on flaccid cocks.

Feng Shui : 5 règles d'or pour vivre plus zen : Femme Actuelle Le MAG

And why some small % of us have shacked up more long term with a good ladyboy bottom..

Answer:

our cock works,

she's a very good bottom that's become better at bottoming over time and

we don't care to waste our time and money on "Your koy yai too much, my toot not open".

zen - The Alden Network

 

Occam's Razor

the idea that, in trying to understand something, getting unnecessary information out of the way is the fastest way to the truth or to the best explanation.

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The post above illustrates precisely the risk of ridicule a monger runs for admitting he enjoys bottoming.   In this case an insinuation that his cock might not work, combined with a non sequitur conclusion that to be in a monogamous relationship with a sissy is a further indicator of steel hard erections...

That's a jab and an uppercut on The-Sith.  And that's so cute...  Maybe The-Sith will jab back once he is done plowing every last trap and chonga in the US East Coast...

But as far as the thread is concerned, it pretty much killed it bc if BMs had so far not shared their experiences with bottoming it's not now that they are going to start...

(... ooooh  the things I know...!...)

 

6 hours ago, Pdoggg said:

 fear (...) of permanent damage to one's bottom and that is why many don't try or give up after one or two experiments.

 

1mrij3.jpg

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17 minutes ago, Rom said:

The post above illustrates precisely the risk of ridicule a monger runs for admitting he enjoys bottoming.   In this case an insinuation that his cock might not work, combined with a non sequitur conclusion that to be in a monogamous relationship with a sissy is a further indicator of steel hard erections...

That's a jab and an uppercut on The-Sith.  And that's so cute...  Maybe The-Sith will jab back once he is done plowing every last trap and chonga in the US East Coast...

I think you misunderstood me. I didn't slight/ ridicule on Sith at all.

After a while I got tired of some ladyboys saying "your cock is too big for my ass" or worse not being able to get hard with hormones.

Infact I praised him for having it figured out what he wants and what he doesn't want.

That's a compliment because too often mongers or first timers are like just go with the flow and often end up with a hefty bar bill trying to please the ladyboy.

So kudos to him being smart and enjoying himself.

You have 1 life to live, why be miserable?

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no offense taken on any of this.

 

I'm totally cool with what I like and very aware of what gets me pleasure and tolerant with what others like and tolerant with myself too........ that's the definition of "cool".

 

I'm a natural top.... and anal pleasure heightens my fun. With GGs.... I'm always top...100% of the time. I don't bother letting them peg me because I don't think its something they can really do.

 

with LBs I use to be 100% top.... and now do both.

I totally agree with the HIV factor. it's horrible. And so my rendezvous are careful and always with condom and not frequent for actually taking a cock in my ass. I might include PrEp into this but its not so easy to get.

 

But whenever I can..... I have them playing with my ass with their fingers....tongue....and toys. And sometimes their dick.

And my sexual experiences have gotten way better because of this!

 

as the drummer at Spinal Tap said.....

 

Have a Good Time, All the Time!

 

 

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it's always been hard to cum. 20 yrs ago my last regular gf, a cute Canuckian was in tears almost over her inability to make me squirt even after I'd told her over and over that no matter HOW GOOD IT WAS, that was not always going to happen. Then the years passed and insensitivity crept in...they might as well be sucking on my thumb. Add some more years (I'm 68 now) and the fucker won't even get stiff for enough minutes to get any job done (tho I will try the blue pill again).  So what's left? Suprisingly years ago I found out that my MOST satisfying act was being fucked to completion. Or getting a mouthful of that good ol "GOD I needed that" jizz.

yeah, I'm a cum slut and a total bottom, it's a calling :)

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3 hours ago, JustSumGai said:

(...) I'm 68 now (and) my MOST satisfying act was being fucked to completion. Or getting a mouthful of that good ol "GOD I needed that" jizz.

yeah, I'm a cum slut and a total bottom, it's a calling :)

Thank you.   The fact that finally one BM other than The-Sith posted to admit to bottoming and explain why gives me the incitement to go another post:

Let's talk about POWER BOTTOM mongers  !   The passive bendovers who supposedly remain in control and set the fuck tempo even if they are the ones being fucked.  I guess paying for it is already a show of power... so is ordering "fuck me" to a sissy, who would probably rather be fucked instead.

I don't bottom much, but when I do: I like to think that I am a power bottom.  The cautious kind who exerts his power to tick a daring sex act off the list and to keep such sex safe and hygienic.   But I think @The-Sith is LBR's best example of a true power bottom.  Do you agree The-Sith?  Did you feel like a power bottom when Sandy jail raped you and left you curling and wimpering on the shower floor (your words) while she peed on you (my imagination)?  Despite The-Sith's submissivness inherent to such scene, I think you were the power one in control bc you scripted or improved (as in "improv") the whole scene and steered Sandy to perform it .   Please The-Sith share your wisdom on power bottoms and why and how you are one?

tumblr_p4pxlyRSET1v58qm7o1_640.jpg

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41 minutes ago, Rom said:

so is ordering "fuck me" to a sissy, who would probably rather be fucked instead.

This the dilemma of ladyboys and the disillusion we buy into. If you got them to be completely truthful in a poll, I'd say 99.9% of them wants to be just that. Lady. 

They do what they need to do, I e fuck old manky sextourist ass for money. When they kick back in their free time, spending our money in a karaoke bar on Soi Kophai they're all in their natural habitat being a lady.

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20 hours ago, Rom said:

Thank you.   The fact that finally one BM other than The-Sith posted to admit to bottoming and explain why gives me the incitement to go another post:

Let's talk about POWER BOTTOM mongers  !   The passive bendovers who supposedly remain in control and set the fuck tempo even if they are the ones being fucked.  I guess paying for it is already a show of power... so is ordering "fuck me" to a sissy, who would probably rather be fucked instead.

I don't bottom much, but when I do: I like to think that I am a power bottom.  The cautious kind who exerts his power to tick a daring sex act off the list and to keep such sex safe and hygienic.   But I think @The-Sith is LBR's best example of a true power bottom.  Do you agree The-Sith?  Did you feel like a power bottom when Sandy jail raped you and left you curling and wimpering on the shower floor (your words) while she peed on you (my imagination)?  Despite The-Sith's submissivness inherent to such scene, I think you were the power one in control bc you scripted or improved (as in "improv") the whole scene and steered Sandy to perform it .   Please The-Sith share your wisdom on power bottoms and why and how you are one?

tumblr_p4pxlyRSET1v58qm7o1_640.jpg

I think you may be projecting. Both the power bottom part and the piss part.

 

i have an idea what a power bottom is.... because someone has bottomed and likes it doesnt make them a power bottom. i like anal stimulation....... I am a natural top that likes the additional physical pleasure of having my ass stimulated.

someone who fantasizes about being a power bottom or passed around as a party bottom or being engaged in piss play should more actively pursue it. 

While keeping it safe..... go for it Rom!

 

 

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oooops.  looks like I touched a raw nerve.  Apologies The-Sith.

This thread was meant to be cathartic about bottoming, which I knew is a subject many BMs (myself included) are not entirely comfortable with (doing it or talking about it).  Some awkwardness and resentment are to be expected when I try to push the discussion further into more intimate aspects.  Please understand.

One such aspect I peripherally touched on above (and that deserves its own thread) is "Watersports" (urophilia, pee play) which is an even more delicate topic and one that I know not to document at ladyboy boards even when i was at PY hellbent on shocking their BMembership with my daring sex life.  Not that I ever pursued it or practiced it much.  Sometimes it happens in shared showers.  I let it out, the ladies or the sissies let it out.  Expressions of disgust or laughs ensue.  Sometimes oral sex.   I once had a GG lover (non-pro) who was very much into it and pushed me into unchartered "waters".  But with the Asian sissies it just does not come up.  Once a Thai one made it his mission to suck me clean every time after I peed.  I dont think he enjoyed the taste.  Just the submissiveness of it.  He was very much a sub and we did things I really did not want to do to him.

That's where I want to get at:  Bottoming and submissiveness.  The two are correlated as the act and pain of allowing others to penetrate you for their pleasure is conceptually as submissive as it gets.  But bottoming and submisiveness are NOT always coincidental.  That's where the Power Bottoms come in and to where I was trying to steer the discussion.  Let me try again:  Anyone here sees himself as a power bottom ? If so, what makes you feel emPOWERed ?

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On 9/8/2022 at 1:56 AM, Rom said:

Are there any other BMs who pass on bottoming even though they know they might enjoy it ?

 

On 9/8/2022 at 8:44 PM, Rom said:

The post above illustrates precisely the risk of ridicule a monger runs for admitting he enjoys bottoming.   In this case an insinuation that his cock might not work, combined with a non sequitur conclusion that to be in a monogamous relationship with a sissy is a further indicator of steel hard erections...

(I haven't read Ashoka's post as an offense too. This just reminds me that forums are sometimes invaded by bottoming shemale customers. Our community needs tolerance and bottoming customers turned up to be the worst intolerant BMs (I think of a forum I left 2 weeks ago that no one knows). I also wonder whther this kind of intolerance is not the origin of PY manners in teh ugly forum. 

I remember a post almost 20 years ago in which a monger (who must be in his 70s now) explained he used to find cheap and easy sex with shemales for prices as low as 20 or 30 FF ( 3 to 5 € now). That was so simple to get a BJ once in a while after work before going back home. Then, one day he he got on all fours and bottomed for the first time. He didn't really explained how he slowly "transitioned" from the top who enjoyed dirty cheap BJ to a bottom. 
I thought about it during my last trips in Thailand. I tried prostate massages first. I din't want to go further than that. Definitely not for me. I also noticed that the kind of ladyboys I enjoy don't like their cock. They either ignore it or even hide it. The subject is off my topics. 

However, I want to wanrn against discussions that could be divisive. We (you) can deal with bottom mongers or top mongers as long as we want. We must bear in mind that we are a small community. I just say "not for me" and I don't criticize. We need each other to share information. 

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  • 3 weeks later...

I can't imagine why bottoms would be the "worst intolerant BM's" and find the use of the word *invaded* to be a bit intolerant actually. Doubt it has anything to do with PY and manners.  I'm pretty sure dedicated bottoms are a real small minority in our special group. Ironically you warn against discussions that could be devisive...does that mean bottoms should keep it to themselves? I'm kinda getting two messages here, as half your post kinda rails against bottoms, but hey some of my best friends are bottoms? Can't we all just get along :)

p.s. 

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17 hours ago, JustSumGai said:

I can't imagine why bottoms would be the "worst intolerant BM's" and find the use of the word *invaded* to be a bit intolerant actually. Doubt it has anything to do with PY and manners.  I'm pretty sure dedicated bottoms are a real small minority in our special group. Ironically you warn against discussions that could be devisive...does that mean bottoms should keep it to themselves? I'm kinda getting two messages here, as half your post kinda rails against bottoms, but hey some of my best friends are bottoms? Can't we all just get along :)

p.s. 

 

No, I don't. What I experienced was far (very far) from PY. After arguments that I won't develop here, one of the guys eventually posted what he meant : we want a guy who doesn't bottom to be banned because he's not one of us. I just don't feel comfortable about a discussion who woulkd be restricted to bottom guys only. (I probably overreacted after this  recent unpleasant experience.). 

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