My Most Embarrassing Moments As An Escort
Updated: 4 days ago
Escorting has brought some truly wonderful experiences into my life...and it's also gifted me a collection of moments that would surely register a perfect 10 on the cringe-o-meter.
One might ask why I’d choose to publish a collection of rookie errors and flinch-worthy follies.
The answer is simple: why not?
Escort websites and social media profiles are often full of carefully curated perfection. Behind the smoke and mirrors, the reality is that none of us are perfect.
From rogue slugs and beef soaked ponytails to accidentally apologising to my own reflection, these are my most embarrassing moments as a Wellington escort.
The Library Cafe Breast Symposium
This was my very first social only booking as an independent escort, and it was at the old Wellington library cafe - if I remember correctly it was called Clark’s.
We were there during the busy lunch hour, and on this day it was jam packed full of elderly ladies.
The conversation was flowing normally - until he began talking about his daughter and the size of her breasts.
Loudly.
People were staring. People were hearing. People were judging.
In hindsight, it was a useful lesson. I'd discovered that conversation steering is a skill, and clearly one I hadn’t fully developed yet.
But as introductions to lunch dates go, a gaggle of horrified grandmothers and a topic I would’ve cheerfully launched into Wellington Harbour wasn’t exactly ideal.
Beef Au Jus Hair Treatment
My very first dinner date was going beautifully.
My client was telling me about visiting Jim Morrison's grave in Paris and I was listening with genuine fascination.
Unfortunately, I was listening so intently that I failed to notice the end of my ponytail had drifted into a generous pool of beef au jus.
Nothing says elegance like marinating your own hair during fine dining, although to be fair, my hair probably needed it.
The Day Discretion Died
My second lunch date ever, and sadly another one that resulted in my face being redder than the CCP.
Truth be told, and I know it might sound silly, but after this occasion I was like, “fuck it”, and took lunch dates off my list of services altogether.
My client and I were seated in a tightly packed Wellington cafe. I can’t emphasise the words “tightly” and “packed” enough. The majority of the seating was at one long table. If I’d stuck out both elbows, I could have just about elbowed the diners to my left and right.
Not that I’d do that, mind you. Always on my best behaviour in public places.
But it illustrates just how damn close everyone was.
We chatted normally at first, but eventually my client began discussing my profession.
Not discreetly, nor quietly, and absolutely not in the sort of voice one reserves for sensitive topics.
The diners on my left heard.
The diners on my right heard.
At one point I wouldn’t have been surprised if the fucken seagulls outside knew what I did for a living.
Our waiter certainly knew. To his credit, he remained the picture of professionalism, patiently hovering nearby and waiting for a gap in the conversation before approaching the table.
Now, having survived the Wellington Library Cafe Breast Symposium a few months earlier, I fancied myself far better equipped to redirect awkward conversations.
Or so I thought.
Every attempt to steer us into safer territory failed. No matter what subject I introduced, somehow he’d circle right back to the fact that I was an escort.
After lunch we were to go to my nearby incall (yes, I briefly offered them) for the bedroom portion of the booking and, yes, he brought that up too.
His comments about what he’d be doing to me later were met with my most desperate attempt yet to change the subject:
“I see Andrew Little has stepped down as leader of Labour.”
It didn’t work.
Looking back, I suppose I could have simply leaned in and quietly said, “Let’s save this topic for behind closed doors.”
The problem was that I didn’t want to embarrass him. He was just completely oblivious to the fact that half the cafe was getting an unsolicited insight into my career.
Note: To be clear, I’m not asking for secrecy so much as basic situational awareness.
I’m perfectly happy to talk about being an escort in public places if a client brings it up first, provided we’re using suitably hushed voices and aren’t crammed shoulder to shoulder with other diners.
If we’re packed in like sardines and half the cafe could join the conversation without moving their chairs, let’s save the finer points of my profession for somewhere a little more private.
Thankfully, this all happened nearly a decade ago. Although I’ve never brought lunch dates back, I’ve shared many, many lovely dinner dates over the years and have never experienced issues with client discretion since.
And if I do in future? I know how to handle it.
The Great Wellington Slug Incident
This remains one of the most surreal experiences of my career.
I arrived at a hotel booking directly from home. Everything was going smoothly.
I took payment, made conversation and reached into my bag to unpack my condom pouch and other bits and pieces needed for the service.
While rummaging around in my bag, I felt something cold and slimy.
"Oh fuck”, I thought. "The lube has leaked." A tale as old as time.
I glanced inside my bag.
It wasn’t lube.
It was a slug.
A full sized, very alive slug. And a real thicc boi, at that.
To this day, I have absolutely no sluggin’ idea how it got there and why it decided to travel with me to an outcall.
Anyone heard of SGFE? Slug Girl Friend Experience? No, me neither.
Still maintaining conversation, and back to making eye contact with my client, I felt around blindly in my handbag looking for something to wrap the slug in. Found a supermarket docket, wrapped the slug in it, and continued as though nothing had happened.
Cool, calm and collected.
Slick as. Literally.
I confess - I felt like a real winner, a covert slug gatherer (whisperer?) extraordinaire.
Please, just let me flex.
I had a shower not long after and I smuggled the slug (fortunately still wrapped in the receipt) into the bathroom bin.
The client never knew.
At least, I hope he never knew. Depends if the slug crawled out of the New World docket I guess.
Never did hear from that client again...
Mirror mirror on the wall, who’s the biggest fool of all?
The majority of these stories are super vintage. While we all love all things retro, here's one that happened a little more recently in February 2026.
I had a booking in a high rise serviced apartment with a three layer security system involving multiple codes.
Glass door one + code: success.
Glass door two + code: success.
Door three + code: where???
There was supposed to be another glass door with a code, wasn’t there? Or nah? Or just a normal door? Maybe even no door at all? Hmmm....
I was about to refer back to my email instructions, but then - THUD - I’d bumped into another lady!
I apologised immediately and stepped back, and while doing so I noticed her jacket and thought, "nice jacket".
It wasn’t another lady.
The entire wall was a mirror.
I had bumped into - and apologised to - myself.
From Sandwich Bags to Business Class
In my very early days of working independently, my "inventory management" solution for condoms was literally a Glad sandwich bag. A sandwich bag close to bursting with as many condoms as it could fit. Big ones, small ones, flavoured ones...all the condoms, because evidently I thought it'd be best to approach every booking with a minimum of thirty at a time.
At the time, I didn't think much of it - I guess I was just improvising as I was starting out. An early setup, if you will, and clearly unaware of the amateur hour vibes I was exuding via this humble zip lock bag.
A few months into my career as Gem a client ended up taking pity on me and handed me a fancy Air New Zealand business class amenity pouch. I still use it to this day, nearly ten years later. (It can be washed by hand.)
This story was admittedly a little tame, but since I've had more than one long time client say to me upon placing my elite Air New Zealand pouch on their bedside table, "Remember when you used a sandwich bag?", I thought I'd include it.
Behold! A woman powered almost entirely by bran!
One evening I had a booking in Masterton (many years ago I used to travel further afield) and as I was about to jump in the car I realised I hadn’t eaten all day.
I went back inside and had a quick rummage through the pantry where I found a box of fibre-licious Kellogg’s All-Bran.
I poured myself a generous bowl and then left the house feeling satisfied with my pre booking meal.
Felt rather full, too…
About twenty minutes into the drive, my digestive system lodged a formal complaint. I undid my fly, and eventually the entire zipper on my jeans. The pain, the pain!
The long drive wore on. As the winds howled over the Remutaka Hill there was also a fair bit of turbulence inside the car.
So.
Fucken.
Windy.
I wasn’t ready to resign myself to the fact that my client was about to meet a woman powered almost entirely by bran. Surely by the time I got to Masterton I’d be all farted out?
And indeed (can I get a hallelujah up in here) the situation had in fact settled by the time I arrived.
We chatted, relaxed, and I quietly reveled in the knowledge that I was no longer Farty McFartyface.
Until...
Yeah. You knew where this was heading, no crystal ball needed for this mortifying moment.
It happened, and I'll explain shortly, but before we go any further I think it’s important to establish a scientifically rigorous tier list of unplanned farts.
Tier 1: The Betrayal
The fart that comes without warning and turns into something else. Surely the scariest fart of all.
Tier 2: Silent But Violent
The fart that comes without warning and reeks to high heaven.
Tier 3: The Diplomat
The fart that comes without warning and resolves internal tensions peacefully and without casualties. Just air, just innocent air - the gold standard to which all farts should aspire.
I experienced the third tier...yay!
But at the worst possible moment...argh!
And when I say the worst possible moment, I really mean it.
The fart was loud - a dynamic bass boost, if you will. The sort of fart that could startle livestock.
And it happened while he was going down on me.
For perhaps the first time in my life, I was completely lost for words.
Eventually, I managed a lame ass “Oh… I don’t know what that was.”
Without missing a beat, my client replied:
“That was a fart.”
And to his credit he took the whole thing in his stride. We laughed about it later, and I saw him several more times afterwards. Onya, Masterton Man.
The Great Under Bed Escape
This next one wasn’t embarrassing for me - although it certainly was for the clients, bless ‘em.
I had a booking with a wonderful couple, N and S. Not their real initials.
It was my second time seeing them, and even though I unfortunately haven’t seen them since, they remain one of my favourite couples.
We were “relaxing together” (hehe) when N suddenly sprang off the bed and sprinted to the window…
Someone had arrived.
After a quick glance outside, she identified the unexpected visitor: her father, who had a key to the house and was letting himself inside.
N and S hurriedly dressed, and, seeing a generous space under the bed, I volunteered to hide under it while they dealt with the situation.
Could I simply have stayed on top of the bed with the bedroom door shut?
Sure.
But where’s the fun in that?
I’m all for adventure, so for several exciting minutes I lay hidden under the bed like an undercover operative while N and S greeted an unsuspecting father.
They were mortified and very apologetic, but there really was no need - I found the whole thing rather exciting! Better work stories and all that.
The time my client was denied a visit to Narnia
This next story admittedly doesn’t really belong here. No one was embarrassed so much as completely and utterly confused.
Had a fantastic booking with a new fulla - drinks were flowing, vibes were vibing. One of my favourite bookings of 2024.
Anyway, all I know is that one minute we're on the bed enjoying a wide range of listed activities and next minute he’s somehow launching himself sideways, colliding with a closed wardrobe door and ultimately falling against it with a big bang.
Neither of us knew what happened.
As I said, the drinks were flowing, but it really seemed like the universe had randomly decided to send him to Narnia, forgetting that the wardrobe door must be open if a mission to Narnia is to take place.
To be fair, he didn’t seem all that embarrassed - and nor should he have been. We were just so absolutely befuddled as to how the hell he’d launched himself at the wardrobe in the first place.
The whole thing was surreal, and actually rather punk-rock.
Looking back, I think these stories taught me a few things.
Firstly, lunch dates were apparently cursed.
Secondly, conversation redirection is a skill that takes practice.
Thirdly, if you spend enough years meeting people from all walks of life, eventually someone will attempt inter dimensional travel via a wardrobe.
Over the years I’ve become more experienced, more confident, and considerably better at navigating the unexpected. Thankfully, the truly embarrassing moments have become fewer and farther between.
Just don’t ask me to bring back lunch dates ;)
