Alright folks, let’s get into this. Been getting a lot of DMs asking about easing into stuff, you know? So yeah, decided to finally try anal properly myself and wrote everything down. Honest truth? It ain’t just jumping in, takes prep.

First Attempt Was a Mess
Started dumb. Thought hey, fingers worked before, probably fine. Got myself a small plug, figured it’d be similar. Wrong. Used some cheap water-based lube I had lying around. Didn’t lube nearly enough either. Tried pushing it in slow, breathing deep. Still felt way too tight, kinda stinging. Got it maybe halfway? Gave up fast. Hurt, felt like my asshole just clamped shut. Realized I knew jack about actually relaxing down there. Was just clenching up expecting pain.
Stopping to Actually Learn Stuff
After that fail, spent a week actually reading and watching. Found out relaxing is a skill, not just luck. Key points hammered home:
- Lube is sacred: Gotta use a ton. I got this thick, silicone-based one recommended for anal. Worlds different.
- Pushing out: Sounds backwards, but not tensing in, actually pushing out gently like taking a dump helps open things.
- Breathing isn’t optional: Deep belly breaths, not shallow panicky ones. Needed to time pushing with breathing out.
- Start tiny: My plug was too big for a beginner. Got a proper anal trainer kit – teeny tiny sizes.
Round Two: Doing it (Mostly) Right
Took this slow. Night before, ate light. Day of, cleaned out properly with a bulb – awkward, but necessary. Set the mood in my room, no rush. Massaged my own butt cheeks first, just getting touch familiar down there. Showered, relaxed.
Got the smallest trainer plug. Covered the damn thing in a massive blob of that new silicone lube. Seriously, soaked it. Put even more lube around my actual anus. Laid on my side, knees kinda pulled up.
Started breathing deep into my belly. Put just the very tip against the opening. Focused on pushing out gently with my muscles, like letting something pass. While pushing out, I exhaled slow and steadily applied pressure. Felt resistance, but no sharp pain. Kept breathing, kept pushing out with my hole. Suddenly, pop, the tiny tip slipped in. Weirdest sensation, intense pressure but not pain.

Held it there, kept breathing deep. Let my body adjust to this weird object being inside. No rush. After a minute or so, pushed out again while breathing out and gently nudged it deeper. Felt the sphincter stretch around it – again, intense pressure, different kind of burn, but manageable. Got the whole small plug in without tears!
Wore it around for 15 mins, moving gently. Just getting used to the feeling. Took it out slow later. Zero pain, minimal discomfort. Success!
Big Takeaways
Can’t stress this enough:
- More lube than you think. Double it. Seriously.
- Start absurdly small. Forget what porn shows. Trainer kits exist for a reason.
- “Pushing out” is the magic trick. It fights your instinct to clench.
- Breathe like you’re meditating. Deep belly breaths, exhale slowly when inserting.
- Go stupid slow. Like, annoyingly slow. Your body needs time to tell you it’s okay.
Felt like a win. Built a foundation. Next step might be the medium size… eventually. Patience, people.