#AlessioHelluvaBoss
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foxwot.bsky.social
Looks like Alessio wanted a taste of that Red velvette Crimson got!
😋 a wonderful 🔞 commisison done by @shinaratani.bsky.social!!
🦈 🇮🇹 💚
#CrimsonHelluvaboss
#AlessioHelluvaboss
#Criminale
Alessio eating that Crim Cake!!
October 30, 2026 at 2:54 AM
chinheitsang2.bsky.social
😍This Alessio doll is so cute!💕 🥺✨I want one too!🦈🪝💚
#HelluvaBoss #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #Vivziepop #Hellaverse #Spindlehorse
bsky.app/profile/asta...
astarvingfarbeagle.bsky.social Boba👽 @astarvingfarbeagle.bsky.social · Sep 29
🪝Finished my Alessio plushie yesterday and wanted to share💚

#HelluvaBossAlessio
A sitting chibi plushie of Alessio Same plushie, front view
September 29, 2026 at 10:53 PM
chinheitsang2.bsky.social
🤭❣️Alessio sees Crimson putting on makeup!👿💄🦈
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #Halloween2026 #Halloween
bsky.app/profile/sato...
On Halloween, October 31st, around 7:00 PM, Crimson was applying makeup in the bathroom. Alessio walked up to the bathroom doorway, grasped the knob with his right hand, and opened the door. He watched Crimson applying his makeup and then explained the matter to him. Alessio: Boss, are you wearing heavy makeup? You look like you're about to perform in a rock band, right? Crimson held an eyebrow pencil in his right hand; he has long bangs and a longer short-hair style; he features black lines on his eyebrows and eyelids, and wears black lipstick. Crimson was wearing a sheer black cropped tank top and tight black micro-shorts—featuring vertical rows of pink "X" symbols on both sides—along with a pair of black thigh-high boots. He turned 180 degrees to face Alessio and told him that, before the Halloween event, he had to dress up as his chosen character. Crimson: How did you guess what was on my mind? Actually, I just wanted to join my friends for some Halloween festivities tonight, so I decided to dress up as a different kind of character. Alessio sees Crimson putting on makeup (Helluva Boss) 30-09-2026
September 29, 2026 at 8:27 PM
chinheitsang2.bsky.social
☺️👍CriminAle Week 2026 Day 3 Body Worship (SFW)😈🦈💕
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #CriminAleWeek2026 #CriminAleWeek
Alessio removed Crimson's hat with his right hand, then transferred the hat from his right hand to his left; with his right hand, he gently stroked Crimson's left horn. Alessio said earnestly: Crim, your horns are very sturdy. Crimson blushed with shyness upon seeing Alessio, and his tail wagged incessantly—a sign that he was in high spirits yet feeling somewhat bashful. Crimson said, looking a bit bashful: Yes, you're right, Ale. CriminAle Week 2026 Day 3 Body Worship (Helluva Boss) (SFW version) 13-09-2026
September 13, 2026 at 5:19 AM
astarvingfarbeagle.bsky.social
#criminaleweek2026 Day 5: Sick/Injury

stupid clingy shark got sick🦈🤧😈

#CrimsonHelluvaBoss
#AlessioHelluvaBoss
Alessio is laying sick in a bed. Tissues are strewn around and and there's a hot tea on the nightstand. Crimson is sitting on the bed next to him, scolding him but also petting his snout. Text: Crimson: I told ya to keep your distance, but ya just HAD to play Mother Hen. Ya know how much that big drippy ass nose is gonna cost me in tissues? Alessio: Sorry, Boss... Crimson: Just get better. I can’t afford havin’ my number one laid up with the sniffles for a month.
September 10, 2026 at 10:47 AM
chinheitsang2.bsky.social
☺️😈🦈CriminAle Week 2026 Day 2 Date Night (Modified)🌃🍷🕯️💚💕
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #CriminAleWeek2026
Around 7 p.m., Crimson and Alessio were enjoying an outdoor candlelight dinner at a restaurant near the beach in Greed Ring. A candelabra with three long white French candles sat on the table, along with two mini scented white candles. Two plates of dinner were on the table: cooked salmon, mashed potatoes, and green beans. Cutlery and napkins were placed next to the plates; a knife was on the right of each plate, with a napkin underneath, and a fork and spoon on the left. Crimson and Alessio were seated, each holding a glass of red wine in their right hand, their eyes meeting and smiling at each other. Crimson smiled broadly, while Alessio smiled with his mouth closed. Furthermore, their tails were curled forward in a heart shape, symbolizing warmth and a deep emotional connection. CriminAle Week 2026 Day 2 Date Night (Helluva Boss) (Modified) 10-08-2026
September 6, 2026 at 5:17 PM
tommy18plus.bsky.social
🥵🔥Alessio masturbates🦈🍌
#HelluvaBoss #HelluvaBossFanart #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #HelluvaBossNSFW #NSFW
bsky.app/profile/crea...
During Alessio's orgasm, his face flushes, he sweats profusely, and saliva drips from his mouth. He rubs his two erect penises together incessantly, licks the right side of his upper lip with his tongue, and then ejaculates, each time releasing a large amount of semen. His tail wags incessantly, indicating extreme pleasure. My CriminAle NSFW Painting (Helluva Boss) 05-09-2026
September 6, 2026 at 12:16 PM
chinheitsang2.bsky.social
🤣👉Alessio mocks Crimson🦈👿
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse
bsky.app/profile/crea...
When Alessio sees Crimson, he can't help but laugh loudly and point at him with his right hand. Crimson crosses his arms, angered by Alessio's appearance. My CriminAle Painting (Helluva Boss) 05-09-2026
September 5, 2026 at 2:57 PM
chinheitsang2.bsky.social
😎😈🦈CriminAle Week 2026 Day 6 Role Swap🚬💚🖤
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #CriminAleWeek2026 #CriminAleWeek
In Ale's office, Alessio, playing the mafia boss, sits in his office chair, while Crimson, Alessio's personal bodyguard, stands nearby. Alessio rests his hands on his desk, clasped together, and looks directly at the camera. He has a cigarette in his mouth and a slight smile. Crimson stands with his hands behind his back, also looking directly at the camera, his expression blank. In the background, three shark tooth figurines hang on the wall, two of which are named "Jake Sammons" and "Bupke Vachell." A herring bone figurine sits on the fireplace, bearing the name "Clupea harengus." There are three bullet holes in the wall, and stubborn bloodstains and claw marks are visible on the wall and fireplace. On the desk, there is an on desk lamp, an ashtray containing ashes and three smoked cigarettes, a pen, a record sheet, and a stack of contracts. In front of a pile of contracts was an introduction card with the company name "Alessio Boss". CriminAle Week 2026 Day 6 Role Swap (Helluva Boss) 26-08-2026
August 26, 2026 at 12:09 PM
tommy18plus.bsky.social
😊😈🦈I have my first CriminAle NSFW paintings.💚💕
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #CriminAleWeek2026 #HelluvaBossNSFW #NSFW
During Body Worship, Crimson examines Alessio's body. Crimson is wearing only dark gray-blue boxer briefs with a herringbone pattern. Alessio is wearing only a dark red thong. Crimson sees Alessio's muscular body and genitals, and gently touches Alessio's penis with his right hand and his buttocks with his left. Furthermore, Crimson rubs his left cheek against Alessio's lower right waist and abdomen. Crimson: Ale, actually your two dicks are quite big, they feel warm and comfortable. Crimson also makes a "rubbing" motion. Alessio places his right hand on Crimson's right shoulder, then looks down at him. Alessio: Don't mind, Crim, I think so too. The sight of Crimson and Alessio not only exchanging pleasant smiles but also blushing suggests a warm sexual desire and deep affection. CriminAle Week 2026 Day 3 Body Worship (Helluva Boss) 11-08-2026
August 26, 2026 at 10:41 AM
chinheitsang2.bsky.social
🤒😈🦈CriminAle Week 2026 Day 5 Sick🥣💚💗
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #CriminAleWeek2026 #CriminAleWeek
Around 8 a.m., Crimson was sick with a fever, his temperature reaching 102 degrees Fahrenheit (38.9 degrees Celsius). In addition to the fever, Crimson also had a mild cold, slight dizziness, and was generally unwell. Crimson sat on the bed in his room, sweating profusely. An ice pack and a thermometer were placed on top of a drawer next to the bed. Alessio was taking care of Crimson, feeding him a bowl of warm oatmeal. Judging from Crimson's expression, he looked quite unwell, but Alessio insisted on waiting about 1-2 days until Crimson fully recovered. CriminAle Week 2026 Day 5 Sick (Helluva Boss) 19-08-2026
August 19, 2026 at 8:49 AM
chinheitsang2.bsky.social
😜😈🦈CriminAle Week 2026 Day 4 Possessiveness📲💌💋
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #CriminAleWeek2026 #CriminAleWeek
Crimson and Alessio both held a cell phone in their left hands, reading messages. Alessio's message: Crimson: Ale, good morning! My favorite breakfast today is hotcakes! Crimson sent Alessio a message with a picture of a plate of hotcakes. Alessio received the picture message from Crimson, which showed a plate of hotcakes. Alessio immediately shared the picture of the hotcakes from Crimson. Crimson's message: Alessio: Crim, good morning! Your breakfast looks delicious. Would you like me to try one of your hotcakes? Alessio's message: Crimson: Um… sure, but I'll let you have a bite! Crimson's message: Alessio: Thank you, you're welcome. Alessio's message: Crimson: Ale, I wanted to ask you something. What's your favorite way to kiss? Crimson's message: Alessio: My favorite way is to kiss the back of your hand. After seeing Alessio's message, Crimson blushed shyly, touched his right cheek with his right hand, and wagged his tail incessantly. Alessio suddenly turned his head to the right, then looked at Crimson with a slightly suspicious gaze. Although Alessio was a little jealous, he understood Crimson's thoughts and feelings. CriminAle Week 2026 Day 4 Possessiveness (Helluva Boss) 15-08-2026
August 15, 2026 at 2:18 PM
tommy18plus.bsky.social
😳😈🦈CriminAle Week 2026 Day 3 Body Worship🫴🍆💚💕
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #CriminAleWeek2026 #HelluvaBossNSFW #NSFW
During Body Worship, Crimson examines Alessio's body. Crimson is wearing only dark gray-blue boxer briefs with a herringbone pattern. Alessio is wearing only a dark red thong. Crimson sees Alessio's muscular body and genitals, and gently touches Alessio's penis with his right hand and his buttocks with his left. Furthermore, Crimson rubs his left cheek against Alessio's lower right waist and abdomen. Crimson: Ale, actually your two dicks are quite big, they feel warm and comfortable. Crimson also makes a "rubbing" motion. Alessio places his right hand on Crimson's right shoulder, then looks down at him. Alessio: Don't mind, Crim, I think so too. The sight of Crimson and Alessio not only exchanging pleasant smiles but also blushing suggests a warm sexual desire and deep affection. CriminAle Week 2026 Day 3 Body Worship (Helluva Boss) 11-08-2026
August 11, 2026 at 1:27 PM
wicken.bsky.social
Some shmucks get the mercy of death. but the unlucky few get put to work.

#ChazHelluvaBoss #AlessioHelluvaBoss #HelluvaBoss #bhm #fatfur?
June 3, 2025 at 5:01 PM
foxwot.bsky.social
Another beautiful piece of Criminale ft Foxelli!! I guess you can say Crimson really Love's his "Penne" pasta!! 🇮🇹 🤌🦈

Thanks again to @cizdude.bsky.social !!

#criminale
#helluvaboss
#alessiohelluvaboss
#crimsonhelluvaboss
Crimson about to dig in some penne pasta! Happy crim!
June 3, 2026 at 4:47 PM
radiospooks.bsky.social
Im no writer just thinking about how crim would probably Hate and love watching ale take care of business at least maybe in their earlier years of ale being his body guard #helluvaboss #crimsonhelluvaboss #alessiohelluvaboss #criminale
March 25, 2025 at 9:28 PM
lilah350.bsky.social
Let me know if you wanna see more of these so i can keep dressing up Alessio

And maybe some other characters that don’t get love #HelluvaBoss #HelluvaBossFanart #helluvabossAlessio #alessiohelluvaboss #helluvabossfandom
February 19, 2025 at 1:45 AM
lilah350.bsky.social
I give you! Math! 🤣

It’s always fun to dress up Alessio for you guys 💗

#HelluvaBoss #HelluvaBossFanart #helluvabossAlessio #alessiohelluvaboss #helluvabossfandom
February 2, 2025 at 9:04 PM
lilah350.bsky.social
Imma sucker 🤣😝 So I give you an incomplete goal reward 🤷🏻‍♀️ #HelluvaBoss #HelluvaBossFanart #helluvabossAlessio #alessiohelluvaboss #helluvabossfandom
January 18, 2025 at 5:57 AM
lilah350.bsky.social
#HelluvaBossFanart #Alessiohelluvaboss #helluvabossAlessio #helluvabossfandom

One down! Counts are add from Here that other place.
Cuz I’m realistic 🤣😅
January 5, 2025 at 11:25 PM
lilah350.bsky.social
“Time to make me some money!” ::Crimson

#helluvabossalessio #helluvabossdressup #helluvabossfandom #alessiohelluvaboss
January 5, 2025 at 12:15 AM
hellacollab.bsky.social
#CrimsonHelluvaboss and #AlessioHelluvaboss arrived!

Check out all of @lilah350.bsky.social 's designs for them on our collab page:
acggoods.com/artist/Hell-...

#criminale #Helluvaboss #Hellaverse #Mermay #Hellacollab
May 21, 2026 at 9:15 PM
hellacollab.bsky.social
It iiisss #CriminAle indeed! Both #AlessioHelluvaboss and #CrimsonHelluvaboss are drawn by @witchsyi.bsky.social !

#Helluvaboss #Hellacollab #acggoods
January 10, 2026 at 7:15 PM
cammyfallen.bsky.social
Crimson x Alessio (Helluva Boss)
#crimsonxalessio
#alessioxcrimson

#helluvaboss
#alessiohelluvaboss
November 9, 2025 at 6:04 PM