Taking BossDog for a ride~
July 22, 2025 at 4:55 PM
Taking BossDog for a ride~
🎶 On the fourth day of Kinkmas, my Bossdog gave to me, four training pups~ 🎄🔔🎁
December 21, 2025 at 1:43 AM
🎶 On the fourth day of Kinkmas, my Bossdog gave to me, four training pups~ 🎄🔔🎁
🎶 On the third day of Kinkmas, my Bossdog gave to me, three French Kisses~ 🎄🔔🎁
December 20, 2025 at 5:23 PM
🎶 On the third day of Kinkmas, my Bossdog gave to me, three French Kisses~ 🎄🔔🎁
Me and who I'm bossdog
January 3, 2026 at 9:05 PM
Me and who I'm bossdog
🎶 On the eighth day of Kinkmas, my Bossdog gave to me, eight pits for huffing~ 🎄🔔🎁
December 23, 2025 at 12:02 AM
🎶 On the eighth day of Kinkmas, my Bossdog gave to me, eight pits for huffing~ 🎄🔔🎁
[commission] Scep gets first dibs on Bossdog! Eager pups have to wait their turn...
January 9, 2026 at 6:04 PM
[commission] Scep gets first dibs on Bossdog! Eager pups have to wait their turn...
🎶 On the first day of Kinkmas, my Bossdog gave to me, a Were-Coop in a pear treeee~ 🎄🔔🎁
December 19, 2025 at 8:37 PM
🎶 On the first day of Kinkmas, my Bossdog gave to me, a Were-Coop in a pear treeee~ 🎄🔔🎁
🎶 On the second day of Kinkmas, my Bossdog gave to me, two docking dogs~ 🎄🔔🎁
December 20, 2025 at 3:45 AM
🎶 On the second day of Kinkmas, my Bossdog gave to me, two docking dogs~ 🎄🔔🎁
🎶 On the fifth day of Kinkmas, my Bossdog gave to me, fiiiiveee golden showerrrrssss!~ 🎄🔔🎁
December 21, 2025 at 4:09 PM
🎶 On the fifth day of Kinkmas, my Bossdog gave to me, fiiiiveee golden showerrrrssss!~ 🎄🔔🎁
🎶 On the sixth day of Kinkmas, my Bossdog gave to me, six hours of edging~ 🎄🔔🎁
December 22, 2025 at 3:08 AM
🎶 On the sixth day of Kinkmas, my Bossdog gave to me, six hours of edging~ 🎄🔔🎁
🎶 On the eleventh day of Kinkmas, my Bossdog gave to me, eleven stinging spankings~ 🎄🔔🎁
December 24, 2025 at 7:35 PM
🎶 On the eleventh day of Kinkmas, my Bossdog gave to me, eleven stinging spankings~ 🎄🔔🎁
Arttober Day 27- Drunk
Looks like Bossdog has had a bit much to drink- is anyone gonna tell him he never buttoned and zipped back up after the restroom? 😅 Fun fact, Waldren's belly gets EXTRA pink when he drinks. He can't help it.
Looks like Bossdog has had a bit much to drink- is anyone gonna tell him he never buttoned and zipped back up after the restroom? 😅 Fun fact, Waldren's belly gets EXTRA pink when he drinks. He can't help it.
October 27, 2025 at 2:01 PM
Arttober Day 27- Drunk
Looks like Bossdog has had a bit much to drink- is anyone gonna tell him he never buttoned and zipped back up after the restroom? 😅 Fun fact, Waldren's belly gets EXTRA pink when he drinks. He can't help it.
Looks like Bossdog has had a bit much to drink- is anyone gonna tell him he never buttoned and zipped back up after the restroom? 😅 Fun fact, Waldren's belly gets EXTRA pink when he drinks. He can't help it.
🎶 On the seventh day of Kinkmas, my Bossdog gave to me, seven paws a-stepping~ 🎄🔔🎁
December 22, 2025 at 5:36 PM
🎶 On the seventh day of Kinkmas, my Bossdog gave to me, seven paws a-stepping~ 🎄🔔🎁
🎶 On the ninth day of Kinkmas, my Bossdog gave to me, nine tally-markings~ 🎄🔔🎁
December 23, 2025 at 3:36 PM
🎶 On the ninth day of Kinkmas, my Bossdog gave to me, nine tally-markings~ 🎄🔔🎁
🎶 On the tenth day of Kinkmas, my Bossdog gave to me, ten bites and scratches~ 🎄🔔🎁
December 24, 2025 at 6:18 PM
🎶 On the tenth day of Kinkmas, my Bossdog gave to me, ten bites and scratches~ 🎄🔔🎁
Waldren Dakis are now available!
I am launching my OWN shop for all of my future merchandise! Starting with two versions of everyones favorite Bossdog! These are available for pre-order at a discount of $65 until January 26th! Don't miss out!
jackaloo.com
I am launching my OWN shop for all of my future merchandise! Starting with two versions of everyones favorite Bossdog! These are available for pre-order at a discount of $65 until January 26th! Don't miss out!
jackaloo.com
January 12, 2025 at 10:54 PM
Waldren Dakis are now available!
I am launching my OWN shop for all of my future merchandise! Starting with two versions of everyones favorite Bossdog! These are available for pre-order at a discount of $65 until January 26th! Don't miss out!
jackaloo.com
I am launching my OWN shop for all of my future merchandise! Starting with two versions of everyones favorite Bossdog! These are available for pre-order at a discount of $65 until January 26th! Don't miss out!
jackaloo.com
Giving me the "I want to go to bed now and you have to go too" look. I think not #BossDog, we have to watch the Dallas game. Chill bossy pup. 🐶 Chill.
December 23, 2024 at 2:13 AM
Giving me the "I want to go to bed now and you have to go too" look. I think not #BossDog, we have to watch the Dallas game. Chill bossy pup. 🐶 Chill.
It’s the LAST DAY LAST CHANCE to get good ol’ Bossdog with his shiny pre-order discount ‼️ if you needed a sign or a reason to treat yourself to a big soft dad to cuddle at night, this is it. You deserve it❣️
Waldren Dakis are now available!
I am launching my OWN shop for all of my future merchandise! Starting with two versions of everyones favorite Bossdog! These are available for pre-order at a discount of $65 until January 26th! Don't miss out!
jackaloo.com
I am launching my OWN shop for all of my future merchandise! Starting with two versions of everyones favorite Bossdog! These are available for pre-order at a discount of $65 until January 26th! Don't miss out!
jackaloo.com
January 26, 2025 at 8:44 PM
It’s the LAST DAY LAST CHANCE to get good ol’ Bossdog with his shiny pre-order discount ‼️ if you needed a sign or a reason to treat yourself to a big soft dad to cuddle at night, this is it. You deserve it❣️
May 21, 2026 at 2:15 AM
Got a new shirt the other day! ✨💪
March 8, 2026 at 10:41 PM
Got a new shirt the other day! ✨💪
No matter what guy always lets us know "I was here first and knew her first." 🤣🤣🤣 #sussexsquad #BossDog
January 3, 2025 at 1:20 PM
No matter what guy always lets us know "I was here first and knew her first." 🤣🤣🤣 #sussexsquad #BossDog
Another silly Bossdog I drew one time. ♡
#CollectiveUnconscious
#CollectiveUnconscious
June 22, 2026 at 1:39 PM
Another silly Bossdog I drew one time. ♡
#CollectiveUnconscious
#CollectiveUnconscious
Bossdog with another banger
June 20, 2026 at 10:08 PM
Bossdog with another banger
🎶 On the twelfth day of Kinkmas, my Bossdog gave to me, twelve loads of backshots~ 🎄🔔🎁
[insert the rest of the song above]
AND A WERE-COOP IN A PEAR TREEEEEEEEEE!!!!
Thank you for singing along everyone! I hope you all enjoyed this festive round of lewdles together and have a Happy Holiday Season :3
[insert the rest of the song above]
AND A WERE-COOP IN A PEAR TREEEEEEEEEE!!!!
Thank you for singing along everyone! I hope you all enjoyed this festive round of lewdles together and have a Happy Holiday Season :3
December 24, 2025 at 7:49 PM
🎶 On the twelfth day of Kinkmas, my Bossdog gave to me, twelve loads of backshots~ 🎄🔔🎁
[insert the rest of the song above]
AND A WERE-COOP IN A PEAR TREEEEEEEEEE!!!!
Thank you for singing along everyone! I hope you all enjoyed this festive round of lewdles together and have a Happy Holiday Season :3
[insert the rest of the song above]
AND A WERE-COOP IN A PEAR TREEEEEEEEEE!!!!
Thank you for singing along everyone! I hope you all enjoyed this festive round of lewdles together and have a Happy Holiday Season :3
Gym shorts that read
BossDog across the booty
BossDog across the booty
January 3, 2024 at 12:10 AM
Gym shorts that read
BossDog across the booty
BossDog across the booty