simkinkster @simkinkster.bsky.social · 17hIt's great to see the marks after a hot scene. Trying single tail whipping again was a real rush. 1170
simkinkster @simkinkster.bsky.social · 29/08/2026First time ever getting fucked by a fuck machine. I was leaking in my cage so hard can't wait to try it again 🥵 2251
simkinkster @simkinkster.bsky.social · 03/07/2026Locked 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 2421
simkinkster @simkinkster.bsky.social · 12/06/2026The theme was B(DnD)S&M so I was a wizard looking to cast hold person 2311
simkinkster @simkinkster.bsky.social · 04/06/2026Love watching the stages of heavy impact take their toll. 0171
simkinkster @simkinkster.bsky.social · 30/05/2026There's just something about showing off in the bathroom 3442
simkinkster @simkinkster.bsky.social · 09/05/2026I would rather be wearing leather at all times. 4595
simkinkster @simkinkster.bsky.social · 03/05/2026Some fun rubber pics from CLAW. Great to have some nice ones in this harness. 5655
simkinkster @simkinkster.bsky.social · 23/04/2026Some pics from CLAW. Sad to be missing IML this year and getting to wear more leather. 2273
Reposted by simkinksterMyfroghashat, now with more Hats @myfroghashat.bsky.social · 22/04/2026Happy #HumpDay from @simkinkster.bsky.social enjoying a shockingly good time 🪢⚡️😈 19211
simkinkster @simkinkster.bsky.social · 14/04/2026This Polaroid from CLAW might be one of my new favorite pics 0354
simkinkster @simkinkster.bsky.social · 19/02/2026I think it's so hot when you can see the cage through a jockstrap 1481
Reposted by simkinksterMyfroghashat, now with more Hats @myfroghashat.bsky.social · 12/02/2026Happy Birthday @simkinkster.bsky.social 🌈🪢🎉 0889
simkinkster @simkinkster.bsky.social · 31/01/2026Getting roped down and beaten by @bootsnbluf.bsky.social at MAL was such a great experience 0212
simkinkster @simkinkster.bsky.social · 24/01/2026Going to have to sort through a bunch of MAL pictures but had such a fun time 1362
simkinkster @simkinkster.bsky.social · 28/12/2025This throat training order turned out to be much hotter than I expected 6946
Reposted by simkinksterSirMF @sirmf1.bsky.social · 10/12/2025Lastly 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 18316
Reposted by simkinksterSirMF @sirmf1.bsky.social · 08/12/2025Time to practice my flogging skills on @simkinkster.bsky.social 29111
Reposted by simkinksterSirMF @sirmf1.bsky.social · 07/12/2025Got sub chained up to the pole in some pvc trackies. Just warm up before he's strapped to the bench. 1969
Reposted by simkinksterSirMF @sirmf1.bsky.social · 08/12/2025Teasing my blind and gagged sub. @simkinkster.bsky.social handled it well. 210119
simkinkster @simkinkster.bsky.social · 23/11/2025I took this as a joke because I don't think I look good in hats. But then chest day was showing so 3714
simkinkster @simkinkster.bsky.social · 13/11/2025Always super fun and sexy to suit up with the quarterback @blfootball2.bsky.social like we did at MIR. 1884
simkinkster @simkinkster.bsky.social · 01/11/2025Another Halloween with a dumb pun. I was a baseball bat. 3531
simkinkster @simkinkster.bsky.social · 26/10/2025Boys who complain about being horny during the end of locktober get put in the no cheating cage. 0622
simkinkster @simkinkster.bsky.social · 22/10/2025I had such a fun and sexy MIR. I met lots of new people this time and got up to lots of real fun play 😈 3435
simkinkster @simkinkster.bsky.social · 08/10/2025Way 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" 0182
simkinkster @simkinkster.bsky.social · 05/10/2025So who am I gonna see at MIR? Really looking forward to getting into some trouble that weekend. 160
simkinkster @simkinkster.bsky.social · 28/09/2025@onth3hill.bsky.social showed me a great time while I was giving my best baseball look 0796
Reposted by simkinksterAZKinkyDom @azkinkydom.bsky.social · 09/08/2025GREAT 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 216016
Reposted by simkinksterMako and Tiger @makoandtiger.bsky.social · 05/08/2025So, every day we add another 5 minutes to the posture correction machine, yes Mako? 😼 531922
simkinkster @simkinkster.bsky.social · 04/08/2025These pictures from Dore might just be my new favorites. Felt so good in the belt and chaps. 3313
Reposted by simkinksterJackson Miller @jaxxxonmiller.bsky.social · 25/07/2025San Francisco sure knows how to make a boy feel welcome W/ @simkinkster.bsky.social 1383
Reposted by simkinksterMaster Nick @kinkysirnick.bsky.social · 11/07/2025Getting some big loads out of @simkinkster.bsky.social while he's strapped to a bondage chair and getting eaten out by @pupsprout.bsky.social. 19110
simkinkster @simkinkster.bsky.social · 21/06/2025It's pride and I'm not a sodomite I'm a sodoDEFINITELY 0130
Reposted by simkinksterMyfroghashat, now with more Hats @myfroghashat.bsky.social · 20/06/2025It’s Pride Fest this weekend in Chicago, who am I gonna see out and about? 🏳️🌈🪢 @simkinkster.bsky.social 2988
simkinkster @simkinkster.bsky.social · 19/06/2025Once again it's time to attempt to team even slightly after all the indoor months of Chicago 1990
simkinkster @simkinkster.bsky.social · 19/06/2025Who called it having sex with a ginger and not Dick à l'orange? 041
simkinkster @simkinkster.bsky.social · 31/05/2025Loved getting into full leather during IML. It feels so good I should just start wearing it around at home more. 1342