If she's getting anal for the first time, what's the best way to start?

Lube lube lube and more lube. As much lube as possible. Astroglide.

With the strap on
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Lots of patience and slowness. Softness. Remembering that she is the most important one out of the two of you right now. Being in tune with where she’s at. Lots of warm mouth and tongue and slippery fingers Lots of lube but not oceans of lube.

With a fist once you are all loosey goosey it will be easy

And always tell her that she loves it, even if she doesn't. So be like "Yeah, you love it, yeah you love it good!".

I imagine small, slow and plenty of lubrication

lots of fingering and then lube, then take it all the way in

Lots of gentle Anal Fingering first followed by a long Tongue Rimming to ease the Anus Hole open and then a very slow and gentle shallow penetration slowly working towards full penetrative Anal Sex when she is Ready ... Checking her feelings all the way and making sure she is okay so that she experiences more Pleasure than Pain 💘 Good Luck 😉😘

With a gag in her mouth so she cant call for help.

gosh thats a tough question for an inexperienced

Asking for a friend?

Are you getting or receiving?

slowly and lots of lube

Slow always wrks

Is this 'she' you?

How was it?

keep it timed entry ,,,slow and steady,,,, no ramming or thrusting

With a small plug, not the plug which blocks the sink either

Anal is like reverse pooping, just think about it

Not with a sir ram'a-lot,trust me on that. 😓😬

A troll in need is a friend indeed.

Heavy meds

how sexy crazy are you for hi anal erotica and pic exchanges?
i get horny inserting into you