Jack-Off Week
@jasckoffweek.bsky.social
Chaotic week of trashy fun - December 29, 2024 - January 4, 2025
#JOW. #JackOffWeek
Mods -
@cannibalsnplaid
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@waywardaf
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@star_swallow
#JOW. #JackOffWeek
Mods -
@cannibalsnplaid
.
@waywardaf
.
@star_swallow
Pinned
Prompties!
Ol’ Jack wants everyone to have fun. Prompts are meant to be accessible. Post a photo, write something, make a collage or an edit or a song, share something you found that fits - whatever you come up with share it!
Go easy or go hard, Jack likes it both ways! :- {D
Ol’ Jack wants everyone to have fun. Prompts are meant to be accessible. Post a photo, write something, make a collage or an edit or a song, share something you found that fits - whatever you come up with share it!
Go easy or go hard, Jack likes it both ways! :- {D
Reposted by Jack-Off Week
December 31, 2025 at 6:14 PM
Reposted by Jack-Off Week
Didn't art much this year, but here's a little roundup of my 2025 stuff:)
1.
1.
December 31, 2025 at 6:13 PM
Didn't art much this year, but here's a little roundup of my 2025 stuff:)
1.
1.
My humble offering to the trickster god #Jackoffweek #JOW
Title: His Name was Jack
Rated: Mature
Summary: An old photograph from a forgotten love affair threatens the comfortable fictions of Stede Bonnet's middle age existence.
archiveofourown.org/works/617670...
Title: His Name was Jack
Rated: Mature
Summary: An old photograph from a forgotten love affair threatens the comfortable fictions of Stede Bonnet's middle age existence.
archiveofourown.org/works/617670...
His Name was Jack - Chapter 1 - wasabi_poptart - Our Flag Means Death (TV) [Archive of Our Own]
An Archive of Our Own, a project of the
Organization for Transformative Works
archiveofourown.org
December 30, 2025 at 5:27 PM
December 30, 2025 at 5:26 PM
its Jack-Off Week so have a StedeJack fic I guess😭
🔗: archiveofourown.org/works/61759801
cc: @jasckoffweek.bsky.social 🙄
🔗: archiveofourown.org/works/61759801
cc: @jasckoffweek.bsky.social 🙄
December 30, 2025 at 5:20 PM
Hell yeah, fortune cookie!!!
November 14, 2025 at 11:49 PM
Hell yeah, fortune cookie!!!
Ol' Jack's been summoned
Hello, I'm not sure what they were going for here but this bottle looked like one (1) singular testicle.
August 23, 2025 at 2:09 AM
Ol' Jack's been summoned
Reposted by Jack-Off Week
Okay STEVE
The party sucked anyway
The party sucked anyway
April 28, 2025 at 12:36 AM
Okay STEVE
The party sucked anyway
The party sucked anyway
Reposted by Jack-Off Week
Pick your poison baby girl
April 28, 2025 at 12:15 AM
Pick your poison baby girl
Reposted by Jack-Off Week
Pirates don't have friends
Just fuck each other over
Except me for you
Just fuck each other over
Except me for you
Day 25 – it’s Form Fuckery Week, an invitation to experiment with writing in forms beyond prose ✍️
Up first: haikus!
the best gay pirates
enjoying life together
or maybe there’s angst
Quote w/ fills, reply w/ recs!
Get silly, let it be amateurish - have fun with it!
#OFMDAUpril
Up first: haikus!
the best gay pirates
enjoying life together
or maybe there’s angst
Quote w/ fills, reply w/ recs!
Get silly, let it be amateurish - have fun with it!
#OFMDAUpril
April 25, 2025 at 7:11 PM
Pirates don't have friends
Just fuck each other over
Except me for you
Just fuck each other over
Except me for you
Reposted by Jack-Off Week
Y’all, check out this fabulous piece of art of Jack enjoying the heck out of Izzy’s tits. #cjizzy #ofmd #ourflagmeansdeath @jasckoffweek.bsky.social
February 23, 2025 at 3:56 AM
Y’all, check out this fabulous piece of art of Jack enjoying the heck out of Izzy’s tits. #cjizzy #ofmd #ourflagmeansdeath @jasckoffweek.bsky.social
Thanks A&A. Always knew I was immortal. 😁
April 5, 2025 at 7:18 PM
Thanks A&A. Always knew I was immortal. 😁
Reposted by Jack-Off Week
Jack: To everyone who has treated me poorly; I am sexier than you.
February 2, 2025 at 3:49 PM
Jack: To everyone who has treated me poorly; I am sexier than you.
Reposted by Jack-Off Week
Reposted by Jack-Off Week
Have we done an idea where Jack has clapper lights installed just so he can make them strobe on and off when he’s fucking someone hard enough?
January 22, 2025 at 5:41 PM
Have we done an idea where Jack has clapper lights installed just so he can make them strobe on and off when he’s fucking someone hard enough?
Reposted by Jack-Off Week
You know what they say, ride a horse and all!
For #jackoffweek I got to cross of one of my to-draws with a cheeky Calico Jack!
I pulled down my original post bc someone kindly let me know the one of my references requests credit when his image is used. My bad... 1/2
For #jackoffweek I got to cross of one of my to-draws with a cheeky Calico Jack!
I pulled down my original post bc someone kindly let me know the one of my references requests credit when his image is used. My bad... 1/2
January 5, 2025 at 10:37 PM
You know what they say, ride a horse and all!
For #jackoffweek I got to cross of one of my to-draws with a cheeky Calico Jack!
I pulled down my original post bc someone kindly let me know the one of my references requests credit when his image is used. My bad... 1/2
For #jackoffweek I got to cross of one of my to-draws with a cheeky Calico Jack!
I pulled down my original post bc someone kindly let me know the one of my references requests credit when his image is used. My bad... 1/2
Reposted by Jack-Off Week
CJizzy as that one scene from Ghost
Commission for @strangeairships.bsky.social
I'm almost done with this batch so feel free tomdm me have many more spots free if you want one !
#ofmd #cjizzy #commission #izzyhands #calicojack
Commission for @strangeairships.bsky.social
I'm almost done with this batch so feel free tomdm me have many more spots free if you want one !
#ofmd #cjizzy #commission #izzyhands #calicojack
January 19, 2025 at 4:07 AM
CJizzy as that one scene from Ghost
Commission for @strangeairships.bsky.social
I'm almost done with this batch so feel free tomdm me have many more spots free if you want one !
#ofmd #cjizzy #commission #izzyhands #calicojack
Commission for @strangeairships.bsky.social
I'm almost done with this batch so feel free tomdm me have many more spots free if you want one !
#ofmd #cjizzy #commission #izzyhands #calicojack
Reposted by Jack-Off Week
I need to catalogue that man’s hair. Show me your back. Show me your shoulders from other angles. Show me the bit where the hair over your belly transitions into
January 20, 2025 at 10:29 PM
I need to catalogue that man’s hair. Show me your back. Show me your shoulders from other angles. Show me the bit where the hair over your belly transitions into
Reposted by Jack-Off Week
Oluuuuuuuu 💚💚💚
jocs is the cj/oluwande ship name
January 20, 2025 at 3:27 AM
Oluuuuuuuu 💚💚💚
Oluuuuuuuu 💚💚💚
jocs is the cj/oluwande ship name
January 20, 2025 at 3:27 AM
Oluuuuuuuu 💚💚💚
Reposted by Jack-Off Week
Okay I admittedly forgot completely about #JackOffWeek despite having it in my calendar but anyway! Reposting some of my older works:3
#edjack #ofmd #nadsart
#edjack #ofmd #nadsart
January 9, 2025 at 9:31 PM
Okay I admittedly forgot completely about #JackOffWeek despite having it in my calendar but anyway! Reposting some of my older works:3
#edjack #ofmd #nadsart
#edjack #ofmd #nadsart
Oh yeah!
January 9, 2025 at 9:37 PM
Oh yeah!