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Tattoo artist working on a detailed design under bright lighting in a studio.

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.

Intricate geometric tattoo on forearm, showcasing bold black lines with complex patterns.

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.

Uncomfortable ghost tattoo with bishop hat and cross detail on skin.

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.

Chest tattoo with the name “Shweta” and a dandelion, representing uncomfortable tattoos created by artists.

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, fk 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 st I get to say “sometimes you’re kicking a*s and eating pussy and sometimes you’re alone and beating it.”.

Man with an intricate tattoo on his back in a blue-tinted room, related to uncomfortable tattoo experiences.

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.

Tattoo of a violin and theater mask, an example of uncomfortable tattoos artists have created.

“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.

Knuckle tattoos reading “LOVE” and “HATE” in a tattoo studio setting.

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.

Tattoo artist creating uncomfortable tattoos in a studio, with art on walls and two people observing.

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.

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 ae 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 as up, holding her as cheeks apart, getting her ae 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”.

Tattoo artist focused on creating a detailed design, wearing a beanie and mask.

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 dk tattoo. When he gets erect it says Ta Da!Moral of the story if you’re gonna get a dk tattoo at least make it funny.

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.

Tattoo on wrist with intricate lettering, showcasing a design that artists found uncomfortable to create.

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.”.

Tattoo artist inking a detailed design on a client’s arm, wearing blue gloves for precision and safety.

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 “al st” 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…

Not a tattoo artist but I asked the guy who gave me my first tattoo this same question and his response was:[sigh]“I’m not proud of this but I used to work next door to a strip club and a stripper wanted zebra stripes in her vagina. Notice I didn’t say ‘on’ or ‘above’. IN her vagina. I kept telling her the same things over and over. The skin there is NOT meant for that. Not only will it not look good AT ALL, it will fade VERY quickly. And it will f***g hurt worse than anything you’ve ever experienced. But she kept upping the price more and more very time I said no. So eventually I just said fk it and basically just annihilated this stripper’s vagina with some zebra stripes. I would’ve felt weirder about it but I’m a guy who’s tattooed about fifty penises in his life so there’s that.”.

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.

Ok so I’m not a tattoo artist myself, but my Dad is, and I’ve heard his stories. When he was young and inexperienced, someone asked him to tattoo a rat tail coming out of her vagina. When he asked why, she said she wanted to tell people that “her pussy ate it.”.

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 fk 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 st 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.

Wife’s friend is a tattoo artist. She said her most memorable was a young woman who came in and wanted Johnny tattooed on her chest because she loved her boyfriend so much. Said boyfriend showed up at the tattoo parlor after she finished so she could show off the new tat, they ended up getting in a huge fight and he broke up with her.Couple months later, girl comes back in with a different dude for another tattoo. Says to the artist, “this is my boyfriend, Johnny!”.

Tattoo of a heart with an arrow, featuring “JOHNNY” on a ribbon, showcasing an uncomfortable creation.

Arm with minimalist tattoos, wearing shorts, featuring unique line designs that artists found uncomfortable to create.

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.

Tattoo of a scuba diver with bubbles on an arm, illustrating unique and uncomfortable tattoo art designs.

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 as while his brothers cheered him on. As 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.

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.

Tattoo artist concentrating while creating an intricate and challenging design on a client’s side.

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 as. 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 as with the bullseye as his ae. He fg got it too.

Tattoo depicting a black and red dartboard, noted as uncomfortable for the artist to create.

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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.

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.

Individual in a gray hoodie standing by a tiled wall; reflective of tattoo artists’ uncomfortable experiences.

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.

Tattoo artist concentrating deeply in a dimly lit studio setting.

I guess this isn’t uncomfortable so much as embarrassing.My dad found an old drawing of an anime cat-girl that I did when I was like, 10, and made me tattoo it on him. I at first tried to say hell no, then I tried to convince him to let me at least redraw it first, but he insisted on that drawing specifically. Yeah.

My families tattoo artist once had a really normal average looking guy come into his shop. The guy looked like a bible salesman or something. He asks what and where we wants it and the dude drops his pants and underwear to show him, and his entire bathing suit area is almost entirely covered in ink. He’s done some weird s**t over the years but something about that one was really awkward for him.

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Not a tattoo artist, but this girl I know wanted to get a tattoo of some clunky, “inspirational” quote that said, “Accept your destiny and the unknown” or something.The tattoo artist drew it out for her before he tattooed it. It said, “Except your destiny and the unknown.” The girl is like, “No, no. Not ‘except,’ the other one, it’s with an ‘a.'” The guy’s like, “Oh, right…” and changes it. He shows her and gets the okay to proceed.He finishes it, and shows her the final product. “Axcept your destiny and the unknown.“All of her tattoos are terrible.Edit: so many typos.

This is my own tattoo but I can imagine how it made the guy feel, it was under my belly button, a big arrow pointing down that said “Enjoy!” Not my proudest moment…

Girlfriend’s mom comes in.She wants a giraffe… Ok. That’s cool.She wants it on her bikini line. Ehh, ok… I’m a professional…Because giraffes have 10 inch tounges… Oh WTF?I get the stencil ready and start prepping for the tattoo, she sees the razor and says “you won’t need that, I shaved for you.“Nope. Not ok. My boss can handle this one.They f****d in the office when it was over.

“We Were Like ‘Oh’": 30 Tattoos That Artists Found Pretty Uncomfortable To Create

I am the canvas and not the artist, but I went to get the word misled on my chest. Front and center. I had just turned 18, was a little drunk and high, and loved the font. Let’s do it!Turns out mislead and misled are two different words, and I basically had liar on my chest for years with the word mislead. Finally covered it up with a self made design and I’m much happier with my chest now.

I know this guy who identifies as a “tree hugger” and he has a tattoo that starts on the side of his face and goes towards his forehead. If you see it you would think its complete gibberish but no, its “victory or death” (I believe) but in the World of Warcraft language of the orcs. Like… REALLY!? Everyone just calls him face tat now and makes fun of his poor decisions he makes on a daily basis.I don’t think anyone could have a worse tattoo than this. I wonder how much he has to pay his tattoo artist for all the stupid tattoo’s he gets.

Not a tattoo artist. But i went on a couple dates with a girl before i met my now wife.I discovered she had a hatchet man tattoo above her vagina. Things fizzled out pretty quick after that.

“We Were Like ‘Oh’": 30 Tattoos That Artists Found Pretty Uncomfortable To Create

While I’m not a tattoo artist, it always makes me uncomfortable to see typos.Just as an example, I once saw someone write “they” when they meant “the.”.

When I was apprenticing a dude asked to have a toxic waste tattoo very close to the base of his dk. I was basically a slave so I had to say yes. He made an appointment and came in drunk as a skunk. He broke a shot glass in our parking lot and my mentor almost beat the living fk out of him. I did the tattoo angel payed and left. It was hairy for a moment but all in all thing worked out. Even the wackos are better in the long run.

“We Were Like ‘Oh’": 30 Tattoos That Artists Found Pretty Uncomfortable To Create

Not a tattoo artist. But I did meet a guy once, a friend of a friend, who, within the first hour of our meeting, pulled out his d**k to show me he had a knife tattoo. He said “it’s cool because it looks like I’m stabbing my girlfriend in the pussy.”.

I am the canvas. I have a chinese dragon styled tattoo. It starts on my chest with the head, then over my right shoulder, down my back, over my left hip and down my thigh. It’s unfinished but in 5 hours I managed to get all of the outline and a third of the shading done.The artist skipped town and now I’m having a difficult time finding someone to finish it.This was painful to have done and I love it. Definitely a conversation piece.

I’m not going to look for it, but I have seen a DEVIL FACE vagina tattoo where the mouth was the opening. So if anyone wants to post that. To be clear, I am not a tattooist and am violating the question.

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