The idea for The Ladyboy gauntlet came from two movie sources , one being the old Clint Eastwood movie aptly named The Gauntlet (only think cum instead of bullets flying) and a macabre sci-fi movie I watched on Netflix called Circle.
Oh you can throw in one more scene from one of the Saw movies where a circle of prisoners were tied to a chair and revolving around a shotgun. (replace cocks for shotguns in this case)
Session Cost :
Mistress Jaa : 7,000 baht
Mistress Wael : 3,000 baht
6 Ladyboys : 12,000 baht (2k each)
Total: 22,000 baht
Session Duration: 2 hours , though we did run way overtime and ended up closer to 3 hours.
Initial Email Request: I want to be used like a sissy , like a whore , be made to serve you in any way you deem fit. After reading some of Mistress Wael’s recent adventures and yours as well I have no doubt that you can provide me with the mind blowing experience I am seeking.
The Ladyboy Gauntlet Session
No bulshit here guys, this is how it went down. I’ve had this idea in my mind for a very long time , going back to when we used to use that “ladyboy hair salon” at the corner of Sukhumvit Rd and soi 5 which was a cover for what we’d arrange in the reclining hair dressing chair in the back room.
Pity that place shut down , it did so way before covid hit , and I’ve been itching to put my session idea into play for the longest time since those two movies manifested themselves into this idea I’ve had floating around in my mind.
It’s a pricey session though , and its not every day a submissive slave walks into town and is willing to drop 22,000 baht on a fantasy.
However, given Mistress Wael’s prowess at arranging mind blowing Female Domination and sexual fantasies , this has all become easy to arrange given her little black book of willing participants that we can call upon.
What blows me away – if you can allow me to digress for a moment – is just how willing certain Ladyboys are to engage in far fetched sessions like this one , whereas Mistress Wael – with me talking to her and helping her – asked over 100 girls lately to just fucking face sit a guy in her 2 hour session and every single one refused. Sukhumvit girls man , they have the combined brain power of a gnat. The only thing they want to do is “fuck & go” – and do so as fast as they possibly can. Which , plays right into our hands as there’s a certain level of imagination , brain power, organizational skills required to arrange such a fantasy. Something a gnat can’t possible handle. That pretty much leaves us as the only game in town when it comes to fulfilling these wild fantasies some of our slaves have.
I wanted to blow this fucking guys’ mind by doing something so far beyond what even he had imagined in his most wildest wet dream – and I knew this idea would accomplish just that.
Mistress Wael did the heavy lifting behind the scenes for me. She has this magical ability to gain immediate rapport with ladyboys – they all call her “mae” (mom) out of respect , and she was able to corral 6 of them to come over to my condo.
You’ve never seen 6 ‘girls’ so eager and willing to destroy a slave like this in your life. The more I whispered into their ears over coffee an hour before the session the more they bounced their own ideas off of me.
One of which was a magnificent idea where the ladyboy with the biggest cock would line up at the 12 o’clock position so that her cock would be the biggest drill in the session.
Ok enough skirting the edges of the fantasy, let me explain to you what the ladyboy gauntlet was to be for my slave.
I had the ladyboy’s line up in a circle , one pair standing opposite one another at the 12 and 6pm position. Two more opposite one anther at the 2 and 8 pm position. And then the last two at the 4 and 10pm position.
The slave was to be pulled into the middle of the circle the way one would drag an unwilling animal into a circus cage and he was to face – on his knees – the dangling cock of the ladyboy standing at the 12pm noon position.
Upon my order , the one standing at the noon position – the one with the largest cock – was to grab my slave by the ears , the hair, the back of the neck – whatever … and fuck the ever loving shit out of that slaves throat.
As deep as she could drill him , as hard as she could drill him, for as long as she could drill him until she was to pull out and explode all over his face.
Simultaneously, the ladyboy standing at the 6 o’clock position … the ladyboy with the smallest cock … was to fuck his ass as ruthlessly as she could possibly fuck it.
I specifically told the ladyboys to have absolutely no remorse for the slave.
They were given the green light to pull out and slap or spank the slave’s ass or face as mercilessly as they wanted. In fact I encouraged them to do so as it would potentially frenzy them into fucking even harder.
When the first ladyboy was to jizz all over the slave’s face Mistress Wael and myself would use popsicle sticks to scrape the cum off and into a shot glass … but NOT before taking a selfie with his cum covered face to be used as blackmail material.
How so?
Well the way I had it envisioned in my mind, each progression to the next ladyboy tandem for the slave would be increasingly painful and harder to endure to the finish.
Thus, for motivational purposes , I had wanted to seize the slave’s phone and have password access so that I could threaten to send each and every cum filled selfie to every single person on his contact list IF he used his safe word before completing The Ladyboy Gauntlet.
Upon finishing the first round , the slave would turn to the 2 o’clock / 8 o’clock duo of ladyboys … the next size up of cock thickness and length … and endure another simultaneous face and ass fucking until such a time that she too would pull out and cum all over his face.
We’d take the selfie , then popsicle stick the cum off the face and into the ever increasingly full shot glass and we’d turn him to face the next pair of ladyboys.
Come the end of the final round we intended to use the shot glass as so …
The slave had to guzzle the entire contents of the shot glass WITHOUT so much as making a disapproving sound or wince of his face , else , he’d be forced to endure The Ladyboy Gauntlet yet again.
However, upon hearing me give the slave this final set of instructions just before The Ladyboy Gauntlet began , they told us in Thai that this would not be possible – not without us supplying them with free Viagra an hour before the session.
Ah, lesson learned.
So I had to just use that final repeat of The Ladyboy Gauntlet as a mere threat , but next time … I’ll be ready with Viagra , handing them out like they’re candy. Because , as I’ll attest to in a moment, the slave did indeed wince and we missed out on what would have been an excruciatingly painful second time ’round the gauntlet.
But man, just that all 6 of the ladyboys were willing to do a 2nd round – had I the Viagra to allow them to do so – opens up endless possibilities in the future.
Because I know you guys have that natural improv instinct to play “yes … and” with all my stories , adding on to and improving all these ideas that I come up with. Which is why these sessions get wilder and wilder as they manifest themselves to improved versions stemming from your ideas going forward.
The slave , needless to say , was both excited and apprehensive at the same time.
It is quite daunting I would imagine to be led up the elevator talking to me as we approach my condo , and then seeing Mistress Wael with 6 gorgeous naked ladyboys standing in what must have looked like a witch’s circle all holding hands and smiling devilishly at my slave as we entered the room.
Yes, quite daunting indeed.
“Drop” I said to the slave as soon as he entered the foyer of my condo and I kicked at the back of his knee to buckle him to the floor. It’s a good Jiu Jitsu trick that Wael taught me some time ago.
From there I attached a collar to his neck and told him to strip naked from his knees – tossing his clothes at the door.
At that moment a very cool thing happened – I could see his knees trembling so violently that he could barely support himself as he raised his left leg to remove his pants and he ended up crashing to the floor as everybody in the room simultaneously burst out in laughter.
From there I could visibly see his ears turn beat red and his knees shook even more … so much so that he had to support his knee with one hand as he tried to kick his jeans off. Never wear jeans in Bangkok in August. Sticky sticky.
With now his right leg raised like a dog pissing and his left hand supporting his left knee as he did so I couldn’t help myself. I saw right away how off balance he was and so I tugged on his collar – this time to the right – causing him to crash into the book shelves by the door.
As a few landed on his head the ladyboys all laughed out loud again and I could see a real determined look overcome my slave’s face , coupled with a mark of concern judging by the stressed wrinkles all across his forehead.
“Come” I said after he had disrobed and I walked him like a dog on his quivering knees into the circle of ladyboys and tugged to the right on his collar getting him to face Judy the 12 O’clock ladyboy.
He gasped at the massive size of her cock. Judy was fucking hung like a bear. Not so much in length as she was 6″ inches hard but in girth , oh my gosh , she was inhumanly thick. It didn’t even look like a normal cock , and trust me ok , I’ve seen 10,000 cocks in my time as a Mistress.
This one looked like a slug. A thick fat buggy looking cock that got thicker and thicker as it got to the base. Uncut too so it looked hideous.
But it was hard as a rock and already leaking cum. Some ladyboys , man , they live for gaping throats and asses and Judy was just such a ladyboy.
It was at this point that I began to explain The Ladyboy Gauntlet and what was awaiting him.
Slaves man , they’re a different breed. The more I explained, the harder he got. Well , until I demanded he hand over the password to his phone , that caused his dick to immediately shrink.
Mistress Wael, without even hesitating crashed down upon his ass with her cat-of-nine-tails with a stroke so hard it made my slave actually yelp. That high pitched – loss of verbal control – that people get only when terrified beyond what they thought was humanly possible … that was the sound he made when Wael hit him.
Without further hesitation he barked out the password.
“Why do you need the password? What are you going to do with it? Don’t sms my wife for god sakes , please.”
I kneeled down beside him and whispered gently into his ear while I ran my fingers softly through his shortly cut hair at the back :
“I’m not going to sms anyone , not as long as you continue to survive The Ladyboy Gauntlet. But the moment you use your safe word , well let’s just say that every contact you have in that phone is going to be looking at photos you definitely don’t want them to be seeing.”
He nodded. His cock growing even larger as he acknowledged those new set of conditions.
It started off awkwardly enough as the smallish ladyboy at the 6 o’clock position took a while to get her cock embedded in his ass.
I can only imagine the pressure of having 7 people staring at you , having to keep your cock hard , and be the first to step forward and get the show rolling – the poor ladyboy was struggling with stage fright at the start and I had this “aww , fuck” feeling and so did Wael for she gritted her teeth as I glanced over at her.
But like starting up a rusty old lawnmower her cock finally came to life once the 12 o’clock ladyboy got things rolling by stepping forward and shoving her cock half way down our slave’s throat.
All it takes is a few moans and audible struggles for guys to get their dicks hard , men be they dudes or ladyboys all love the concept of something being forced.
I think Judy has always had trouble with slaves consuming her whole cock and she wasn’t as forceful as I had hoped and neither was the small ladyboy fucking as hard as I wanted , so I gotta admit the whole thing got off to a so-so start.
Sure enough , Judy pulled out after 10 or so minutes and gushed her cum all over our slaves face allowing Wael and I to get in beside him and take a selfie with one of us on each side of his cheek pointing at the small sized mess of cum dripping mostly down his nose.
Again, at that point it felt like a wedding rehearsal … you know, where you are going through the motions but the anxiety and the tension aren’t quite there yet?
That changed though as soon as we made him rotate to the 2 and 8 o’clock ladyboys , and it changed in an instant.
Again, sorry I don’t have all their names put to memory yet, it was Mistress Wael who arranges these things from her little black book of contacts.
What I can describe for you is just how rough and explosive the 2 o’clock ladyboy with the gargantuan boobs was.
She stepped up and within seconds was absolutely drilling the guy’s mouth. So much so that each thrust was making him slide backwards onto the dick of the ladyboy at 8 o’clock and she was doing a good rhythmic pounding job back there.
At one point we had to reset the circle because the 2 o’clock ladyboy had pushed our slave a good 5 meters outside the circle with her cock thrusts.
Her method was to grab our slave by his long hair on the side of his head and use that for leverage. She wasn’t fazed by his gagging or the oodles of spit that her cock was extracting with every withdrawal.
The load on his face from her cumshot was sizable and by the time we had scraped that 2nd load into the shot glass there was enough to swish around.
The third pair in the rotation were off balance with the rear ladyboy going absolutely ape shit on our slave’s ass – by means of grabbing his love handles and literally pulling his asshole onto her cock.
Which meant the ladyboy doing the mouth drilling was always having to shuffle forward to mouth fuck our guy and could never get it deep for too long.
At exactly the same moment Wael and I looked at one another and in one of those great moments where two people think alike we both made the same hand singles indicating we had the same idea in mind.
Flip the ladyboy positions.
And oh boy.
Once we matched up the crazy ass fucker with the mouth destroyer our slave experienced 15 minutes of the hell he had so desperately sought all his life. And then some.
He was trying to gasp out in desperation but neither would let him. Not for one moment. Oh, and it was rhythmic as well. Like a furious concert of cock strokes , in and out, in and out in unison.
There were a few moments where they would shift out of the “in the front , out the back” rhythms to where they would both penetrate at the same time.
It was in those moments that our slave made sounds I had never heard before.
Sorry there’s no better way to describe it , I don’t mean to be cruel but imagine the sound somebody would make being double impaled by swords in a field of battle. Exactly that noise.
Like a short super panicked gasp / squelch … oh kind of like if you stepped on a dog’s toe … but a huge fucking dog with a deep bark … that kind of short yelp.
Over and over our slave was just getting worked over and oh my , when the face fucking stopped the cum shot was legendary.
First shot went in his eye, the second one directly up his nose , the third into his hair … which subsequently dripped down into his other eye and the rest dribbled out onto his mouth.
By the time we took the selfie and gathered all that cum the shot glass was 3/4 full. Clearly it was going to overflow.
Wael and I moved closer together to discuss whether we should end the sequence with those two swapping positions but we decided against it hoping the girth of the 12 o’clock ladyboy would give us the finish we were hoping for.
Oh did we ever get the finish.
That yelping I just tried to describe above changed immediately to outright screaming and collapsing on the floor as she tried to work her godzilla cock into his ass. Clearly he had not ever experienced that kind of pain in his ass before.
Twice more he fell to the floor trying to escape her cock and so I said to Wael out loud “I’m going to send this photo to Renee”
“Noooooooo , fuck nooooooooo” he cried out. “Please. Please. Please.”
“Then take her cock without falling down for if you fall one more time I’m sending these to everybody” and I began naming off people in his contact list. I nodded over at godzilla cock to resume and she did.
He did that silent scream where his chin lifted way up so that he was looking directly at the ceiling for a moment , then with his mouth gaping wide open and his eyes rolled back in his head he sort of screamed but not a sound came out.
Then to try and compensate for the entry he tried to bow his head and rest his forehead on the floor but in dramatic fashion the cock sucking ladyboy lifted his head up with both her manly hands , grabbed him by his cheek bone, and inserted her whole cock down his throat.
His feet began to kick the floor and then he grunted as godzilla cock finally crept in that final inch and he was double impaled. Fuck , it was magnificent.
No acting, no embellishment , no fake fucking sounds.
They just stayed there motionless , both enjoying his quivering body as it tried desperately to adjust to being fully impaled from both ends. His knees were back to convulsing. Not just shaking but fully convulsing.
In fact, it seemed in that minute that the only thing keeping him from keeling over to one side or the other were the two cocks in his throat and ass.
The pounding began again and this time godzilla cock was making full exit and entry insertions and the poor boy , every time she entered him he would lurch forward and re-impale himself with the other cock in his throat.
Then he just gave up. His body went limp and the two ladyboys didn’t give a single fuck in the world. They kept going harder and harder but this time they both pulled out and both jizzed on his face at the same time one from the left and the other from the right.
His face was completely soaked in cum. But I could still see tears running down his left eye only and mixing in with the cum on his left cheek. His right eye was closed from the stinging of cum that had gotten inside his pupil.
Basically he was a total mess. We took the selfie anyways.
I was completely let down by the downing of the cum filled shot glass though. I was really hoping that he would cry, wince, moan or even better – gag on the cum.
And he didn’t disappoint, he winced. However, as I mentioned at the start, the ladyboys were all drained and my condo looked like the end of a hot air balloon festival without the Viagra to prolong it.
Our slave, nonetheless , had survived the ladyboy gauntlet. But at what price?
He could barely walk and even when he did his hand was wrapped around clutching at his asshole.
His voice was unintelligible with the raspy quality of a 100 year old pack-a-day smoker.
The poor guy’s knees were knocking against one another because he was shuffling with his feet so close together they were touching. I guess walking like that helped tighten up his gaping asshole? I dunno.
When he finally emerged from the shower fully dressed I let him sit down ever so slowly on the sofa , easing himself gently onto the seat cushion before asking him:
“So, mind blowing enough for you?”
“… and then some” he replied. 🙂
Mistress Jaa
Mistress Wael
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If you decide to fill out the form, double check that you’ve typed in your email address properly cuz guess what? If you fuck that up, I can’t get back to you, end of story. It’s shocking how many guys can’t spell their own email address.
Mistress Wael is available from 1pm until 10pm every day, while I am available at either 7pm or 10pm Monday – Thursday and 4pm on Friday’s.
1 hour sessions are 5k baht while 2 hours are 7k.
Human Toilet Training with Mistress Wael is 15k and with me it’s 20k.
With Mistress Wael sessions are outcalls at your hotel, house or condo and with me they are held here at my condo.
Check out our Fees & Bookings page for all the information you need to know for booking your session with us.
Mistress Jaa : [email protected]
Mistress Wael : [email protected]
[…] In fact I don’t have any concerns presently. I’m fully booked , Wael even more so. The Ladyboy Gauntlet story has taken off and is by far the most in demand session right now, regardless of the […]