Trail Bear @trailbear.bsky.social · 03/10/2026Well I’ve had them on all day, but just getting a chance to post. #jocktober2026 day 2! 0141
Trail Bear @trailbear.bsky.social · 01/10/2026It’s the best time of year! Happy #jocktober2026 to all that celebrate. Today’s theme is blue! 0202
Reposted by Trail BearCarolinaBeef 🦍➡️ Western Xposure 10/8-10/11 @carolinabeefbull.bsky.social · 27/09/2026It’s been awhile 👋🏾🥰 948648
Reposted by Trail BearBigBroTaco @bigbrotaco.bsky.social · 26/09/2026My new Star Wars shirt calls for appropriately themed space underwear. A new pair courtesy of @rugratapparel.bsky.social 7904
Reposted by Trail Bear🏳️🌈 Alexanders Biscuits ⭐️ @fierybiscuts.bsky.social · 22/09/2026A “brief” glance at random pictures from the other place. I love briefs, easily top choice for my favorite underwear. They just look so heckin’ cute. I got in my head that people are tired of old stuff, etc. It’s all stuff you’ve seen before blah blah but a little encouragement helps a lot! :3 3263879
Reposted by Trail BearAspen & Cam @aspenpup25.bsky.social · 30/09/2025Pound the cum out of me 😈💦 #gay #gaycub #gaybear #gaychub #gaypup #nsfw #gaychubby 225626
Reposted by Trail BearDaddy’s Big Bitch @aspicynugget.bsky.social · 19/09/2026Fat boy Friday ft the speedo some nice boys from Melbourne gave me 950331
Reposted by Trail BearThe Fruity Bear @onbeario.bsky.social · 08/09/2026A little #mcm from the last swim of summer, and also the colour version because I look good in colour 1331114
Reposted by Trail BearBrandon 🧸 @brandonthecub.bsky.social · 02/09/2026Messy room but I looked good here 😈 318618
Reposted by Trail BearMarquis The Honey Bear @marquis.bsky.social · 20/08/2026Gotta get the pump in before going to the theater to watch a musical pro shot for 2 hours 🫡 325228
Reposted by Trail BearBearybrian🎃 @bearybrian.bsky.social · 05/08/2026For National Underwear Day (and #humpday) please enjoy this assortment of my favorite jocks, briefs, etc. 1539831
Reposted by Trail BearBearyBrad @bearybrad.bsky.social · 21/07/2026A happy #TummyTuesday and #TightyWhiteyTuesday (even though they’re navy briefs - let me have this) from my flight home from Cincinnati! The airplane bathroom was very very small.. 41349
Reposted by Trail BearDennis Nedry’s Butterfingers @snacksatanorgy.bsky.social · 17/07/2026The booty was bootying this morning. 650823
Reposted by Trail BearOld Major Pig @sociologistpig.bsky.social · 16/07/2026*goes to a bear week pool party hosted by @chonkclub.bsky.social exactly once* 768859
Reposted by Trail BearStearbear @stearbear.bsky.social · 19/02/2026I just LOVE how my ass looks in this thong 2502
Trail Bear @trailbear.bsky.social · 15/07/2026Take two with my photo: This week I’m combining a late Tighty Whities Tuesday with a Wet Wednesday thanks to all the sweat from my jog. Are these too sheer now? Shear? Ones for a sheep right. 0211
Reposted by Trail BearStlcitybear @stlcitybear.bsky.social · 14/07/2026Summer vibes and cheetah print 467042
Reposted by Trail BearRick 🥝🥝🥝 @rickqmx.bsky.social · 10/07/2026Some jockey tighty whities I've not been in the mood for pics lately but took those yesterday before work 3705
Trail Bear @trailbear.bsky.social · 08/07/2026About to head home from the beach luckily I’ve got these new sexy undies to wear for my ride. 0100
Reposted by Trail Bearmowxla @mowxla.bsky.social · 07/07/2026wearing slutty underwear helps depression 🙂↕️ 3077230
Trail Bear @trailbear.bsky.social · 07/07/2026In the past week I took a shower at the gym for the first time and wore my speedo on the beach. Both of these things I’ve been so terrified of. I feel so liberated. 050
Trail Bear @trailbear.bsky.social · 02/07/2026Well pride is over. But I’m still fucking gay. Here’s to more undies pics all year! 050
Reposted by Trail BearNorthwest Cub @northwestcub94.bsky.social · 01/07/2026Final submission from tighty Whities Tuesday 😮💨 841937
Trail Bear @trailbear.bsky.social · 28/06/2026Well the blue faded a little more than I wanted. But I still like them I think. 190
Reposted by Trail BearDennis Nedry’s Butterfingers @snacksatanorgy.bsky.social · 28/06/2026Breaking my own dirty mirror rule. Just seeing the fingerprints and cum. Such a MASSIVE error on my part. 1286344
Trail Bear @trailbear.bsky.social · 27/06/2026Went to a queer book swap today so wore my book briefs and Frog and Toad shirt in honor of the occasion. 070
Trail Bear @trailbear.bsky.social · 26/06/2026I’m a very excited to see how these turn out after being laundered. I’ve been wanting to try cyanotype for years. I’m nervous the Hanes will look weird on my hips once I put them on. 140
Trail Bear @trailbear.bsky.social · 24/06/2026Rocked the elliptical for an hour this morning because my old man joints are hurting. Resting now listening to my new audiobook “There Be Dragons Here “ by S.L. Rowland. 080
Trail Bear @trailbear.bsky.social · 23/06/2026Headed to the beach in a few weeks. I really wanna try and wear a speedo for the first time out and about. Anyone have any Speedo suggestions? 000