Trailhead
@trailheadgay.bsky.social
Helpful guides for adventurous bois.
Protect your partners
January 24, 2026 at 1:00 AM
Protect your partners
Don't mask the feelings. Learn to love the stretch and sensations
January 22, 2026 at 7:00 PM
Don't mask the feelings. Learn to love the stretch and sensations
Relax as you breath out 😮💨
January 21, 2026 at 3:30 PM
Relax as you breath out 😮💨
This is a hands-on sport
January 21, 2026 at 1:00 AM
This is a hands-on sport
Studying your map can help you open up new territory for play
January 19, 2026 at 3:30 PM
Studying your map can help you open up new territory for play
Check your lube before play
January 19, 2026 at 1:00 AM
Check your lube before play
Gently massage around the hole and pull the outer rings open
January 17, 2026 at 7:00 PM
Gently massage around the hole and pull the outer rings open
If you see something, say something.
January 16, 2026 at 3:30 PM
If you see something, say something.
Learn your body to connect with your body
January 16, 2026 at 1:00 AM
Learn your body to connect with your body
The right bottle can make clean up so much easier
January 15, 2026 at 1:00 AM
The right bottle can make clean up so much easier
Practice your breathing every day.
January 13, 2026 at 3:30 PM
Practice your breathing every day.
Don't let a poorly prepared space be the reason you're stingy with lube
January 13, 2026 at 1:00 AM
Don't let a poorly prepared space be the reason you're stingy with lube
If you see brown, you may keep that down,
If you see red, something must be said.
If you see red, something must be said.
January 12, 2026 at 1:00 AM
If you see brown, you may keep that down,
If you see red, something must be said.
If you see red, something must be said.
Filing your nails as a fidget toy during breaks is a great way to always be prepared
January 10, 2026 at 7:00 PM
Filing your nails as a fidget toy during breaks is a great way to always be prepared
Filing your nails as a fidget toy during breaks is a great way to always be prepared
January 10, 2026 at 1:00 AM
Filing your nails as a fidget toy during breaks is a great way to always be prepared
Be prepared with the right supplies for easy clean up
January 9, 2026 at 1:00 AM
Be prepared with the right supplies for easy clean up
Would you venture into the woods without a map?
January 7, 2026 at 3:30 PM
Would you venture into the woods without a map?
A good boi trains often and cleans up as needed
January 6, 2026 at 3:30 PM
A good boi trains often and cleans up as needed
Vibe is everything
January 6, 2026 at 1:00 AM
Vibe is everything
Nothing should feel sharp - espcially not your nails
January 5, 2026 at 1:00 AM
Nothing should feel sharp - espcially not your nails
Normalize having adult conversations about STI risks
January 3, 2026 at 7:00 PM
Normalize having adult conversations about STI risks
Take deep breaths there boi.
January 2, 2026 at 7:00 PM
Take deep breaths there boi.
Quick clean ups for quick play sessions.
January 1, 2026 at 3:30 PM
Quick clean ups for quick play sessions.
Protect your hole from infection
January 1, 2026 at 1:00 AM
Protect your hole from infection
The best doms give more than they take
December 30, 2025 at 3:30 PM
The best doms give more than they take