How do i start pleasuring myself anally?

Start with fingers or a small butt plug and use lots of lube! Seriously - when it comes to lube, if you think you've used enough use some more!

If you're a bit squeamish about using a finger, try something like the Vixen Creations "Spur". It's a nice thin realistic dildo made of VixSkin, which I'm sure you'll love. Take it slow, use lube and just relax

Lube your finger & just rub around your anus, vary the pressure. When you are ready lube up some more & just put your finger in a little little bit & pull out & repeat. Then maybe 2 fingers, spread your fingers a little. Don't over do it all at once.
Maybe start in a warm bath tub.

Yes - lots of lube is a must! Too much lube is almost enough. The best thing to start with is your finger/a partners finger. If you'd rather not use your hands directly, you can throw on a rubber/latex glove (like in the doctors office). Make sure your fingernails are trimmed, and start off with your pinky, teasing around the opening. Once you've relaxed you can start with some penetration, adding another finger when you feel ready. You could also try a good silicone probe like the Tantus Ripple.

Again I have to recommend lube!

You could start with fingers if you like, or with some sort of toy.
The anal starter (link) might be a good choice- it's small and inexpensive.
My first anal toy was this plug: link which is also inexpensive, but it's just a bit more girthy.

In general, I'd say start with a small toy. Be sure NEVER to use any toy anally unless it has a flared base of course, you don't want to be losing anything in your butt!!
Also, be cautious, and take it slowly. If you aren't enjoying yourself, stop. If anything hurts, stop. Don't push yourself too far.

fingers.

get really horny and masturbate a bit normally to start. then lube up a finger and do some circles around the rim of your anus. should feel good already! take your time and slowly go deeper and deeper with a finger. dont skimp on the lube and don't go too fast. I'm talking 1/4", then 1/2" then 1". eventually you'll love it in there!

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