25 Ink Masters Reveal The Strangest Requests They’ve Encountered

Published 1 month ago

Tattooing is often seen as a form of artistic expression and personal transformation, but for those who wield the needle, it’s also a profession filled with unique challenges. Recently, a Reddit user posed an intriguing question to tattoo artists: “Which tattoo made you the most uncomfortable to do?” The responses poured in, ranging from the bizarre to the deeply unsettling, revealing the wild and unpredictable nature of the tattooing world.

Some stories took on a darker tone, highlighting the moral and ethical dilemmas tattoo artists sometimes face. Read some interesting answers below.

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Image source: subhunt1860, pablogomez / Instagram

I was asked by a research lab to tattoo 3 hamsters that were identical. Like a little symbol on two of them, so each could be distinguished. I wasn’t sure if it was real or not, as the interaction was over the phone.
I tattooed a couple of real characters over the years, including one guy who kept getting the same tattoo over and over again (a tiger head) and eventually just got little dots to fill in around them all, and another guy who got vertical and horizontal lines on various body parts to make himself appear larger. He talked about getting additional teeth implanted so he could process food more efficiently, and wanted me to be his disciple.


Image source: jacobchex, cottonbro studio / Pexels

My ex-girlfriend’s best friend was dating a guy at the time named Dustin. Her nickname for him was ‘Dusty’. I’ll let you guess what she got tattooed… right above her vagina.

She’s not dating him anymore, so I’m sure that’s an interesting one for current / future partners.


Image source: anon, Pavel Danilyuk / Pexels

I’m not a tattoo artist, but this is good…

I went into a tattoo parlor to do some human trafficking education. The owner was very receptive. As I was showing him the tags used by the human traffickers active in our area, he became visibly uncomfortable and started calling over his artists. It turns out that they had done dozens of one of these tattoos. They thought it was a fad. When I asked if any of the women to whom they had applied these tattoos came into the shop alone, the owner turned white as a sheet. And started crying. He has been branding slaves and he never knew it.

Edited to add: Please stop asking me to post images of the brands. If a human trafficker finds out that their brand has been made public, they will cut or burn it off their victims. And then rebrand them.


Image source: overcomebyfumes, tribaltattooer

I was flipping through my tattoo artist’s portfolio as I was waiting for him to get set up to do the massive tribal piece on my arm. I got bad tribal a while back, and, since it was pretty much unfixable as it was, the only solution was to go over it with a bigger tribal piece.

Anyway, I’m flipping through, and turn the page to an ultra-realistic black and grey portrait of Hitler on this guys ribs. I almost drop the book.

“Hey (artist’s name)! What the f**k is up with this? You actually did this?”

“Well, that’s from my shop out in (rural area about two hours away). It’s a little different out there.”

“Yeah, but… I mean you tattoo Nazis?”

“That’s a long-time client, and yeah he’s a Nazi douche, but he tips well. Anyway, the joke’s on him, ’cause that’s not Hitler.”

“What do you mean? It’s clearly Hitler.”

“Look closer.”

“I’m not seeing it.”

“It’s Charlie Chaplin. Did you really think I’d tattoo Hitler on someone?”

And, yeah. It was Charlie Chaplin.


Image source: wishmewells, xMiakatx / Reddit

My friend is a tattoo artist and a guy came in wanting a KKK tattoo. So the very heavily muscled black tattoo artist came out like “you’re gonna be in my station.” The guy shuffled out of the shop very awkwardly.


Image source: Grimzkhul, nijhawan31 / Instagram

Couple came in to get their names tattooed on each other, I hate doing those but I inform them about the risks etc. She was getting hers across the lower back, his on the stomach. I start with the guy, big dude too, large piece once I’m done she says something like: “now deal with this m**********r!” Slaps hims “This’ll teach you to cheat on me with my best friend!” And hastily makes her way out of the shop.


Image source: andiewtf, Anh Tuan T / Unsplash

It wasn’t so much the tattoo, but rather the customer. He was a very strange older guy, and out of 7 artists in the shop, only one could tolerate working on him. He came in sometimes days in a row, and normally we don’t recommend getting multiple tattoos so quickly, but with this guy it was like, f**k it.

He came in one time for a semi truck with ‘kicking a*s and eating pussy’ written on the back window. A few days later he came in to get ‘alone and beating it’ – completely unaware of the irony. Now whenever someone’s going through some s**t I get to say “sometimes you’re kicking a*s and eating pussy and sometimes you’re alone and beating it.”.


Image source: anon, Pavel Danilyuk / Pexels

I’m not a tattoo artist, but I briefly dated a guy who was. He had a handful of stories of folks who made him uncomfortable, but the one that sticks out the most is the elderly dominatrix.

She came in, told him what she wanted: a tattoo of a sexy lady with a paddle doing one of those physically impossible romance novel poses. She wanted it huge and she wanted it on her back.

The entire time, she told him about all the dungeons she went to and how much she loved hurting boys and how pretty he was and that he should visit her sometime. And he was trying very hard to be like, “THAT’S NICE I WORK BETTER WHEN YOU’RE NOT TALKING, THOUGH.”.


My long time artist (he’s done at least a dozen on me) had a woman come in and ask for her husband’s d**k imprint to be tattooed on her tongue.

She was politely sent away.

Image source: CrushingPowerOfWaves


My regular tattoo artist and friend messaged me one day that she tattooed a penis. I instantly had so many questions! She explained how in this long story about him getting semi hard when she put the stencil on then going totally limp the second the needle hit his penis and how she had to stretch it out with her free hand while tattooing. Finally I asked what he got. Thor’s hammer. I laughed so hard. At least it was funny.

My coworker brother in law also has a d**k tattoo. When he gets erect it says Ta Da!

Moral of the story if you’re gonna get a d**k tattoo at least make it funny.

Image source: momadance


When I had only been tattooing for around 2 years, some old guy got the initials D.N.R, said it was his wife’s initials.
Shortly after he was done, he told me it legit was “do not resuscitate “. I felt horrible as f**k about it. A while ago on here, a year ago maybe, a similar discussion was going on. Some resistors cleared it up however and said that paramedics would still do CPR etc in the event regardless of the tattoo.. still, felt fairly horrid about it. I never knew at the time.

I’ve done a lot of weird s**t over the years. One time I tattooed a woman’s a*s with a mans name, later found out it wasn’t her husbands name and they both wanted another mans name there so it made him feel like he was f*****g someone else’s wife. I get role play but that’s being dedicated lol.

Image source: ItsJustGizmo


Image source: king-khajiit, 1_quarto_studio_art / Instagram

I was getting tattooed once and this guy comes in to get a tattoo of a diver swimming out of his a*****e. Luckily I was lying down so I had an excuse not to look over but the artist seemed kinda uncomfortable afterwards.


Image source: Vilonious, genes_tattoo_company / Instagram

I worked in a tattoo shop for many years, and I gotta say, we all had a good sense of humor, but one that stands out to me as being extra hilarious, was an older (gay) gentleman, who got a HUGE violin on his back (like from his buttcrack to the back of his neck. We of course asked why he chose that, and he said “my partner plays violin, and he wanted to be able to ‘play’ me from behind” and we were like “oh”

Also, when he got to the lower part of the tattoo (near the but) he stood up, and revealed that he was wearing break away pants and proceeded to sit butt a*s naked for the rest of the tattoo. The artist doing it was soooo uncomfortable but the rest of us were dying from laughter. Great day. I miss working there sometimes.


Image source: anon, torrestattoo.studio / Instagram

“HATE LOVE” on the knuckles. I said no, said he would regret it and so on. He got mad at me and started calling me names. Instead of screaming back, my “f**k you” was that I agreed to do the tattoo.


Not an artist (though I do have a lot of ink) Dated a girl once with numbers tattoo’d on her wrist. As it was highly unlikely she had been in a concentration camp, I asked her for the story. It was her social security number, apparently her mother had this done to both her and her brother in case (and I quote) “they find your body but the head’s been cut off and they need to identify you”.

Yeah that family was a little messed up.

Oh and it was pretty sloppy, like prison level, so considering that and the fact that it would have been done on children, it wasn’t likely done at a professional shop.

Image source: Nymaz


Image source: CWavves, Motoki Tonn / Unsplash

Tattoo artist here.

I recently had a man come in and ask about getting a name covered that was placed right above his genitals. He brought a drawing in of a tribal dragon that he did himself. After explaining that his drawing really wouldn’t work for the area or the cover up he said, “I guess that spot wasn’t a great place to put my daughters name huh?” After a really awkward few moments he left.

I didn’t end up covering it and haven’t seen him since.


Image source: emimhatstat, cottonbro studio / Pexels

Not me, but my tattoo artist.
When I went to him for my first tattoo, I made small talk and asked him this same question. He had a stripper come in and ask for a star tattooed on her a*****e with cursive script on it saying “I’m a star”.
While he was tattooing her, his wife and 7 year old son surprised him with lunch, as a stripper kneeled face down a*s up, holding her a*s cheeks apart, getting her a*****e tattooed. Apparently both the wife and young lady were very chill with the situation, but my artist didn’t like having to explain why daddy was “putting his art in her butt”.


Image source: Gandalfthepinkk, ink.byhales / Instagram

My tattoo artist told me of a tattoo he did around the edges of a strippers b-hole saying”one ring to rule them all”. I remember him mentioning how bummed he was that she didn’t allow him to photograph it for his portfolio.


I’m not a tattoo artist but I worked as a receptionist for 6 years in a popular local studio. I’m quite talkative and friendly so I liked to chat to the clients while they were waiting for the artist to set up. A late 40 something year old conservative looking woman came in wearing her work skirt and blazer. I signed her in and got her to complete the consent form and asked what she was having, she just replied “oh some text on my lower back”. I replied that was cool and then showed her into the room where the artist was working. I could hear the artist and client deciding on placement and that she wanted the tattoo low enough on her back so that her daughter wouldn’t see it as it was private. So it’s pretty much just above her butt crack. Fair enough I thought.
Afterwards I asked the artist what she had. The woman had the words “a**l s**t” tattooed in thick black script. No wonder she didn’t want her daughter to see it!

She came back a few months later to have “woo whore” tattooed on the front…

Image source: always-aimee


Image source: Njodr, ohsorob_tattoo / Instagram

I worked in a tattoo shop that my friend owns after I graduated high school. One day a gay couple come in and one of them says he wants a dart board on his a*s. Ok, I thought. A little odd, but ok. I don’t really care because I’m not the one doing the tattoo, my friend is. Anyways, after he says he wants a dart board, he clarifies and says he wants it regulation sized. The initial confusion took me for a moment and I thought, “No.” This mother f****r wanted a regulation sized dart board on his a*s with the bullseye as his a*****e. He f*****g got it too.


Gang members generally have their own people to do their tattoos. Normal “street “ shops don’t have to deal with legitimate gangsters. I tattooed in Oakland for many years and did a lot of local “40th ave” or whatever their street affiliation, but no serious gang tattoos. Turned down a few swastikas, but not many. I put “party hard” in script on a frat douches a*s while his brothers cheered him on. A*s tattoos on dudes was about the worst. Never tattooed a d**k, I always said it would be expensive and nobody ever ponied up the dough. Like was previously mentioned, 90% of the job is super mundane. I was asked to tattoo a deceased person who had apparently wanted a tattoo, I declined because of a lack of consent. Memorial tattoos are hard if you’re a caring person, the hurt really comes to the surface during the process. I enjoyed sharing their burden for a while.

Image source: subhunt1860


I was getting a tattoo on my calf in Magaluf…yes I know, great start. My tattoo actually turned out great but a group of lads sat down in the room adjacent to me, big glass windows so I could see everything. Boy wanted “ANDY” on the sole of his foot…

He was carried out half conscious before it was even finished.

Image source: Rubberbandballmaker1


Image source: mackenzie_2113, Monstera Production / Pexels

I was being tattooed once and this guy walked in, super strange and we could tell something was off about him. He was wanting some kind of Japanese symbol on his forehead and my artist(shop owner) asked him if had any other tattoos. The guy says no and the owner tells him he won’t do face tattoos without having any other tattoos. This guy proceeds to just stare at us all for a solid two minutes without saying a word. Wide eyed, like we were from outer space and told him the Earth was flat. Then the artist says “Sorry man. I can tattoo the symbol on you anywhere else but I won’t tattoo it on your face without any other ink.” The guy continues to stare at us, says okay, slowly turns around and walks out the door. We thought he was going to come back and k**l us.


I went to my shop for an appointment and I was walking in to the extremely crowded shop when my tattoo artist grabbed me and told me to come outside. As soon as we got out the door he burst into laughter. He told me to come back to his booth to grab paperwork and check out the piece he’s finishing up. But I absolutely cannot laugh.
Sitting spread eagle in a chair with one foot propped up in a chair, this extremely large woman was grinning at me pointing to her crotch (at least she had underwear on?) Where my buddy was coloring in a “caution wet” sign. She also informed me that the tattooed “puddles” dripping down her legs were in fact “sex juices”.
I let out a quick “oh. Wow” before I had to get the f**k out of the store and let out a good laugh.
After she left my buddy said it was a rough one but she paid insanely well. We still laugh about it when I see him.

Image source: static_fiction


Image source: meowmeow138, cottonbro studio / Pexels

The discomfort came after. When the client was paying I went to grab the money and he said something along the lines of “you like that money baby?”

It was awkward I’m usually quick with comebacks, but I just stared at him until he left.

Also the women who moaned loudly the whole time I tattooed her. She said it was to help her ease the pain, but I’m not entirely convinced as I was near her lower regions.

Also not me, but my boss and other workers at the shop had to deal with a lady that would reach into their shorts. Some liked it some didn’t, plus she was aggressive and would call for the lords help loudly every time she got tattooed.

Saumya Ratan

Saumya is an explorer of all things beautiful, quirky, and heartwarming. With her knack for art, design, photography, fun trivia, and internet humor, she takes you on a journey through the lighter side of pop culture.

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strange tattoo requests, tattoo, tattoo artists, tattoos, uncomfortable tattoo artists, weird tattoos
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