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simkinkster

@simkinkster.bsky.social
882 followers 191 following 94 posts

Submissive. Chicago. My Erdös number is 5 if it comes to that. Recon: simkinkster

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simkinkster @simkinkster.bsky.social · 17h
It's great to see the marks after a hot scene. Trying single tail whipping again was a real rush.
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simkinkster @simkinkster.bsky.social · 29/08/2026
First time ever getting fucked by a fuck machine. I was leaking in my cage so hard can't wait to try it again 🥵
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simkinkster @simkinkster.bsky.social · 06/07/2026
See you in the locker room
1210
simkinkster @simkinkster.bsky.social · 03/07/2026
Locked boys are the best at knowing what locked boys want. "If you cum like this then we can keep you permanently in the belt" @axxpup.bsky.social
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simkinkster @simkinkster.bsky.social · 12/06/2026
The theme was B(DnD)S&M so I was a wizard looking to cast hold person
2311
simkinkster @simkinkster.bsky.social · 04/06/2026
Love watching the stages of heavy impact take their toll.
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simkinkster @simkinkster.bsky.social · 30/05/2026
There's just something about showing off in the bathroom
3442
simkinkster @simkinkster.bsky.social · 09/05/2026
I would rather be wearing leather at all times.
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simkinkster @simkinkster.bsky.social · 03/05/2026
Some fun rubber pics from CLAW. Great to have some nice ones in this harness.
5655
simkinkster @simkinkster.bsky.social · 23/04/2026
Some pics from CLAW. Sad to be missing IML this year and getting to wear more leather.
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Myfroghashat, now with more Hats @myfroghashat.bsky.social · 22/04/2026
Happy #HumpDay from @simkinkster.bsky.social enjoying a shockingly good time 🪢⚡️😈
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simkinkster @simkinkster.bsky.social · 14/04/2026
This Polaroid from CLAW might be one of my new favorite pics
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simkinkster @simkinkster.bsky.social · 19/02/2026
I think it's so hot when you can see the cage through a jockstrap
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simkinkster @simkinkster.bsky.social · 13/02/2026
My ass is all I've got for you 😈
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Myfroghashat, now with more Hats @myfroghashat.bsky.social · 12/02/2026
Happy Birthday @simkinkster.bsky.social 🌈🪢🎉
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simkinkster @simkinkster.bsky.social · 31/01/2026
Getting roped down and beaten by @bootsnbluf.bsky.social at MAL was such a great experience
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simkinkster @simkinkster.bsky.social · 24/01/2026
Going to have to sort through a bunch of MAL pictures but had such a fun time
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simkinkster @simkinkster.bsky.social · 04/01/2026
Ready for the Chicago chastity social
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simkinkster @simkinkster.bsky.social · 28/12/2025
This throat training order turned out to be much hotter than I expected
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SirMF @sirmf1.bsky.social · 10/12/2025
Lastly getting @simkinkster.bsky.social strapped to the bench and take out some frustrations on him. Man I love the sound of my hand slapping his ass. #spanking #kink #ass
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SirMF @sirmf1.bsky.social · 08/12/2025
Time to practice my flogging skills on @simkinkster.bsky.social
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SirMF @sirmf1.bsky.social · 07/12/2025
Got sub chained up to the pole in some pvc trackies. Just warm up before he's strapped to the bench.
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SirMF @sirmf1.bsky.social · 08/12/2025
Teasing my blind and gagged sub. @simkinkster.bsky.social handled it well.
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simkinkster @simkinkster.bsky.social · 23/11/2025
I took this as a joke because I don't think I look good in hats. But then chest day was showing so
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simkinkster @simkinkster.bsky.social · 13/11/2025
Always super fun and sexy to suit up with the quarterback @blfootball2.bsky.social like we did at MIR.
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simkinkster @simkinkster.bsky.social · 01/11/2025
Another Halloween with a dumb pun. I was a baseball bat.
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simkinkster @simkinkster.bsky.social · 26/10/2025
Boys who complain about being horny during the end of locktober get put in the no cheating cage.
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simkinkster @simkinkster.bsky.social · 25/10/2025
Halloween part 1
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simkinkster @simkinkster.bsky.social · 22/10/2025
I had such a fun and sexy MIR. I met lots of new people this time and got up to lots of real fun play 😈
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simkinkster @simkinkster.bsky.social · 08/10/2025
Way hornier than usual at this point in locktober. And sounds like I'm not the only one. Gotta be something in the air.
0362
simkinkster @simkinkster.bsky.social · 07/10/2025
"I'm not giving you any warm up today boy" "Yes Sir"
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simkinkster @simkinkster.bsky.social · 05/10/2025
So who am I gonna see at MIR? Really looking forward to getting into some trouble that weekend.
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simkinkster @simkinkster.bsky.social · 28/09/2025
@onth3hill.bsky.social showed me a great time while I was giving my best baseball look
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SirMF @sirmf1.bsky.social · 10/02/2025
love anything shiny
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AZKinkyDom @azkinkydom.bsky.social · 09/08/2025
GREAT COCK TO EDGE The leather stud #AZBoy330 normally keeps his #hung cock in a chastity belt. And he does so exactly to allow a Dom to do this for long periods of time. #gaybondage #gaybdsm #edging #milking #hungmen @simkinkster.bsky.social
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simkinkster @simkinkster.bsky.social · 09/08/2025
I just wanna ride (you)
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Mako and Tiger @makoandtiger.bsky.social · 05/08/2025
So, every day we add another 5 minutes to the posture correction machine, yes Mako? 😼
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simkinkster @simkinkster.bsky.social · 04/08/2025
These pictures from Dore might just be my new favorites. Felt so good in the belt and chaps.
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simkinkster @simkinkster.bsky.social · 27/07/2025
Sometimes you just gotta sniff
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simkinkster @simkinkster.bsky.social · 25/07/2025
Chaps really help show off the behind barz 😈
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Jackson Miller @jaxxxonmiller.bsky.social · 25/07/2025
San Francisco sure knows how to make a boy feel welcome W/ @simkinkster.bsky.social
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simkinkster @simkinkster.bsky.social · 12/07/2025
Stole my look
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Master Nick @kinkysirnick.bsky.social · 11/07/2025
Getting some big loads out of @simkinkster.bsky.social while he's strapped to a bondage chair and getting eaten out by @pupsprout.bsky.social.
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simkinkster @simkinkster.bsky.social · 22/06/2025
Giving switch
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simkinkster @simkinkster.bsky.social · 21/06/2025
It's pride and I'm not a sodomite I'm a sodoDEFINITELY
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Myfroghashat, now with more Hats @myfroghashat.bsky.social · 20/06/2025
It’s Pride Fest this weekend in Chicago, who am I gonna see out and about? 🏳️‍🌈🪢 @simkinkster.bsky.social
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simkinkster @simkinkster.bsky.social · 19/06/2025
Once again it's time to attempt to team even slightly after all the indoor months of Chicago
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simkinkster @simkinkster.bsky.social · 19/06/2025
Who called it having sex with a ginger and not Dick à l'orange?
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simkinkster @simkinkster.bsky.social · 31/05/2025
Loved getting into full leather during IML. It feels so good I should just start wearing it around at home more.
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simkinkster @simkinkster.bsky.social · 16/05/2025
Looking forward to suiting up at IML again
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