From Assassin to Ass Man

The story of one guy getting naked in a mask and oiling himself up — and that’s just what we can show you!


Hidden behind a superhero mask sits what some would call an insanely attractive man, with his chest oiled up, one arm above his head and the other down below stroking his member. He has been going at it for hours, sometimes getting up bending over to play with his rear. No, this stud isn’t enjoying a session of self-love; he is making money. A lot of money. His name is Diddlepool and he is taking the adult cam site, Chaturbate, by the horns. Or, his horn at least.

The man behind the mask likes to keep things secret. His true identity is known only to the owners of Chaturbate and his personal page holds little details as to who the man really is. Even his family and friends know nothing of what he does.

“I keep them out of the loop as well. I just don’t want to put anyone else in the position where I have to trust someone else with my identity and they can spoil it. It’s just way simpler to keep everyone in the dark.”

That, however, is not something that drives away viewers. In fact, Diddlepool said this is in part why his audience is so large. Something about the mystery of his identity brings viewers back time and time again.

“I get a lot of requests to take the mask off and obviously like, no…it’s sort of like half the people aren’t into it and the other half are really into it. They like the whole mystery factor, they like that I could potentially be someone they know, they just don’t know I do this now.”

However, that has never happened, at least to his knowledge. And if it has, no one has told him. Diddlepool said his fascination with exhibitionism started while he was in high school with the advent of texting. He said he would sext and enjoyed that aspect of being watched sexy. It was the idea of being seen in sexual situations in front of people that caught his interest. He then went through and found the various Reddit pages where users posted NSFW (Not Safe for Work) photos of themselves.

“There is the /r/gonewild section, and things like that are pretty cool. That was sort of a gateway drug for me,” said Diddlepool.

About a year ago, the performer said he found the site Chaturbate and started doing broadcasts without being paid.

“I don’t know how I actually found it…I kinda lurked for a while and then I did a few shows — you can go on there and you don’t have to verify yourself or anything.”

So why the Deadpool mask if he didn’t need to verify himself? The need for a secret identity.

Because the mask had to be full faced and there are only so many fully-masked comic heroes so Diddlepool settled on his choice of Deadpool. It also helped that he started wearing the mask around the same time the movie came out, so he capitalized on the film’s success.

“That was back before when I did the exhibition shows, I didn’t want to verify because I didn’t want CB to have all my information because I was like ‘oh what if they release it or they get hacked’ or something like that happened. I have since gotten over that.”

Now, he just uses the mask as a gimmick and because he really likes the character.

“I also have always liked Deadpool, breaking the fourth wall and all that stuff is really cool. Huge comic book nerd here so it worked out.”

And that is part of what makes his mystique that much better. The character of Deadpool has always been a sort of anti-hero. He is the bad-ass, does what he pleases, flirts with anything that moves kind of guy. Avoiding identification and finding loopholes around rules is something the super anti-hero is known for.

“You can just go on and say you’re 18 and do exhibitionist shows; you can’t get tips but you can just kind of go and do your thing.”

Eventually, he was told by viewers that he could get paid for performing. After trying it, Diddlepool said he really got into the groove and has been enjoying the paid shows for roughly two months.

Aside from providing a sexual stimulant, the shows have also helped him pay off his student loans quicker.

“I usually make about fifty bucks a show. It varies based on my work schedule and things like that but I’m officially — I have super cheap rent — but I’ve been paying my rent doing this. Which is really good because I still have a ton of loans from school so I can actually funnel that into that.” Before getting paid Diddle was in it for the exhibitionism.”

“[Exhibition] was sort of part of why I started doing it. But since I’ve been there, there’s a lot of [cool people.] I like meeting new people, I like seeing what they’re into.”

Diddle said that one thing he enjoys about the site is the private shows. For his time on the site, the performer said he has only done a handful of private shows where he was able to see what people were into, and that was part of the excitment or allure for being online.

“There was one guy who had me get naked and blow up balloons for him until they popped. That was what got him off,” he said. The show would run for approximately 15 minutes and Diddlepool said he made thirty bucks for each one. “The only thing is that it was kinda loud and I couldn’t really do it at night so I was kinda restricted but we figured it out. It was interesting. I made good money so hey.”

Not all his private shows went off without a hitch. During his first time on the site, Diddlepool said that he encountered a man who would latter end up cyber-stalking him.

At the time of their meeting, Diddlepool said that he would not verify his account because he was afraid the site would get hacked or share his private information. So when he met this man, the deal seemed perfect.

“I met some guy who was like, ‘yeah I’ll pay you for a private show through Paypal.’ I was like OK, that sounds good, I can get paid for this and I won’t have to verify.” The performer then began to do several shows for the soon-to-be stalker, which Diddlepool said got stranger and stranger each time.

“He wouldn’t let go of the wanting to see me in person and I would repeatedly tell him no and he would just insist that we were going to do it and that was where it kinda started to spiral out of control.”

During this time, the performer had various accounts to help connect with viewers on different platforms. When this viewer went off the rails Diddlepool began to block or ban all the accounts this man had. He said he was “just trying to get rid of the guy.”

This, however, is not the strangest thing about their relationship. Apparently this man was into impregnation. Yes, impregnation.

“At some point he had me finish [ejaculating] into a bunch of condoms and had me send him those condoms and he would like put them in his butt.”

The condoms weren’t just novelties either, they were expensive. Diddlepool said he charged ten dollars per condom. He added that he was in a worse financial situation at the time so he wouldn’t do anything like that at the moment. Still, the condom thing wasn’t what set things over the edge. It was just mainly the whole insistence on meeting. Now however, the performer has new accounts and he does not believe the man recognizes his new persona.

“He did find me again, but I don’t think he knew I was the same guy because I was wearing a different mask and different room and different set up. I wasn’t sure if he knew who I was or not but either way I banned him everywhere I could. Hopefully that won’t be a problem anymore. I think when you ban someone they’re only banned for six months, so in six months I’m going to have to figure something out.”

For someone as energetic as Diddlepool, there is only the here and now, which is also part of his gimmick. The superhero he uses as an alter-ego is also known for breaking the ever-present fourth wall. Diddle said that he enjoys doing the same to help drive his tips up.

According to Diddlepool, around 80 percent of his audience are just lurkers browsing anonymously, some without accounts. Of the other 20 percent of viewers, half don’t participate but tip and the other half participate or tip or both.

“The participation is kind of interesting because a lot of people that actually show up don’t talk much. Even if you only have 10 people talking it’s pretty exciting; you get a pretty active room.” And the more active, the more tips he is likely to earn. What else helps earn tips? An ambiguous sexuality and range of turn-ons, much like the comic character.

Like his counterpart, Diddlepool doesn’t openly disclose his sexual orientation or exact turn ons to keep people interested. He doesn’t mind keeping his orientation hidden because at the moment he has no plans to meet up with anyone in real life.

“I perform for anyone who wants to watch me perform. I don’t currently state my sexual orientation because I don’t think it is that relevant. I don’t have any plans to actually meet up and do anything with these people so I don’t want to pigeonhole myself into one side or the other, also I don’t want to ruin the whole fantasy thing where people think you could be into them and that sort of thing.”

On the site however, the performer has a host of friends that are both male and female who tip him regularly. Most are men, which Diddlepool said is because most users on the site are male.

Whether or not he is gay, straight, bi, or asexual does not matter; Diddlepool has managed to meet and connect with other users who build up the Chatturbate community. He said that it has been very friendly and helpful to have other performers show him the ropes.

“I’ve made a lot of friends since I’ve started there. The whole community is really nice. Even like other people that do shows have been really helpful and helped me out. The’ll teach me how to do certain things and stuff like that…other performers [sometimes] go on there, hang out and throw me some of their tips. And then every now and then I’ll throw them some tips. It kind of keeps things moving along, it sort of helps each other out.”

This community has been especially helpful for the performer. Many of the existing users have shown him the various features of the site and have even gone to encourage viewers to tip during his live shows. It just isn’t other users that make Diddlepool’s shows unique.

On his page, Diddlepool has a list of actions and how many tokens they cost to perform. For example, a bicep flex is 10 tokens, a dick smack with his hand is 25, and to oil up his booty it is 200 tokens, just to name a few.

Of this list, he said, “That’s been a work in progress and it’s probably going to keep changing based on what people want or request what things are worth more than others or what is seen as more valuable. Like for example the oil thing I do halfway through, it’s more of an effort to keep the show going and get bigger tips. It’s also the kind of thing I can only do once, you can’t just re-oil it doesn’t have the same effect.”

Some things have just evolved on accident, and he has capitalized on that to keep himself fresh.

“I think the cock slap thing just kind of happened one time, someone asked for it and I did it and people were really into it so I was like, ‘alright this will be a thing.’ [I do it usually] on my hand or on my chest.”

Noises are are usually pretty affective, and that is part of the attraction to caming sites like chatturbate. Users log on and get a somewhat custom experience based on their turn-ons, where as other sites a simply static. You are not going to generally see the kind of talent that you see in real porn — although there are some people that do porn on cam.

“A lot of the people that model — especially the guys — are average dudes that might be muscular and good looking but that are just normal dudes that interact with people.”

Diddlepool said there are some people who just want him to wear shoes on the show. They don’t care about anything else, just the shoes. Every once in a while he said he would pan down and show them the shoes, but nothing else.

“The whole ability to interact with the show is what sets us apart from just like PornHub, that’s what I think brings people to CB, so I don’t know I’ve tried to capitalize the best I can. I think that’s really how you build a successful show. I’ve had a pretty good run of it so far.”

Despite his openness for viewers, Diddlepool is not without his limits, though he did admit that over time those limits have changed. Before recently, he said he was opposed to anal play. Although he has tried it, it is something he is not very interested in, at least at the moment.

He once received a prostate massager from a viewer that he experimented with. But, unlike the cock slap, it was not something he enjoyed. Diddlepool said that showing off isn’t an issue, it’s the penetration.

“Showing stuff, I’ll do. I show my butt a lot. That’s usually one of the things people like so I do it. It’s not like, it doesn’t really matter to me if I’m showing my butt but, there’s not anything ever going in there.”

It hasn’t all been fun and games for the 20-something-year-old cam star. A major priority for him is to remain anonymous, which hasn’t been particularly easy. For example, he has thus far successfully managed to keep his two lives separate, which has proved difficult at times.

“So that’s an interesting kind of story because nobody actually knows I do this. At all. I literally tell nobody I do this.”

Part of it is because of his career. Although he has no problems with sex work or performing, he believes that if anyone found out that he is a sex worker — and by definition he is considered a sex worker — they would not understand. He added that some people may consider it morally wrong.

“I just feel like there is a big stigma against it, and also that’s the whole reason I wear a mask which is for my work situation. If this ever got out to anyone…it’s just a lot simpler to keep it on the DL. Make my money, have my friends, keep the two lives separate because if this ever got out into my professional life it would be really, really bad.”

For now, Diddlepool does not see himself going any further than he already has. He said he would do more private shows because they’re “usually more efficient with my time.”

“I think I’m in a kind of holding pattern right now and even like the amount of money I’m making. I’m kind of okay just doing. I don’t see myself stopping soon, in the near future, maybe a year’s time but not sooner than that. It really depends on if my living situation changes.”

And his advice for newcomers looking to go live? Have a decent set up. According to the performer that makes a lot of difference — if you have a grainy camera and people can’t see you or hear you then you’re not going to have a lot of success right off the bat. Diddlepool suggested getting a camera from Bestbuy or some other electronic store.

“I think my camera was only 30 bucks and it made a huge difference in the numbers that I saw with people tuning in.”

He added that it is best to just find a way to set yourself apart, to make it fun for yourself and your viewers.

Despite some early issues, there have been more good times than bad, which is what keeps him on the site. He mentioned that there have been some interesting people with interesting desires that have come across his page. Most of the time, these people average folks with tastes that they may not be comfortable voicing out-loud, but behind the keyboard all bets are off.

“There was one guy who wanted me to make out with my bicep. It’s part of why it’s kind of fun to me. It’s interesting to see what people are into.”

Graphics by Albert Serna Jr. photos courtesy of Diddlepool.