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I recommend relaxing, breathing deeply, and taking it slow. Fap a little before you get started and get horny.

I think the easiest position is on your knees, sitting on your finger or toy. Sharpie pens seem to work well for some people.

Lube up whatever you're going to play with, lube your hole, inhale deeply and let it out, and relax as much as possible before you ease it in. Push out (as if you were going to poop) as you push it in there. That helps your sphincter relax.

Once it's in there a little ways, stop and get used to the feeling or pain. Breathe deeply and relax again. Play with your dick a little more until you are feeling good. Being turned on helps a lot to work through any minor twinges of pain.

After the session, rest a few days and let your hole heal, and repeat. This is a long-term process, and you can't just stretch yourself to take a thick 9-incher overnight. It takes a lot of experimenting on how to relax and open yourself up before you can comfortable let a guy bang up in there.

Don't use body wash as lube. That's going to irritate the lining of the rectum. Find a water-based lube that you like. Preferably not one that contains irritants like the "warming" or "tingling" sex lubes.

If you're going to use your fingers, make sure your fingernails are clipped and smoothed.

I find a position like the one in your picture the most comfortable for me. (On my back, legs spread and up.)

Pretty much as you get familiar with the feeling of having things inserted, you begin to relax and be able to accept larger toys.

If you feel pain, stop, and do more foreplay. Forcing yourself will just cause you to tighten up more, and that leads to tearing and damage. Anal bleeding isn't fun, and it will be a number of days before you feel like playing again.

Well, I also used the end of a razor, because I could feel my fingernails.
I did what >>659 said squatted down first, and got it in, but took it out because of the pain. Then I tried what >>661 said, laying down, legs spread, and thought it was harder to get in.

I dunno. I'll try more tomorrow, or the next day.

Your guy covers his cock in lube and slowly shoves it in and you take it and jizz your prostate off while it goes balls deep. No need to practice

Relax and take this cock, bish. lol

I just bottomed my first time the other day with a transgendered woman I met on manhunt (best sex of my life). It hurt like hell because she was way to eager and I didn't have a chance to prepare, but once as I got her to go slow, I just pushed like I was taking a poop and she went right into me. The sex after that was pretty amazing!

>>721 congrats! :)

I work in the adult industry n agree dont use anything but lube for anal! Also may i add dont use water based lube as the lube will desolve quickly get yourself some silicone or lube that is designed for anal! There is an anal lube product that has a relaxing additive with it! With anal lube up loads! Also i suggest you douche yourself also clean ur insides out n when u do make sure the water comes out clear. Then use the lube! Lube up anus and also lube up ur fingers or whatever u use! BUT i suggest u get a toy that is flexible! And with all anal GO SLOW AND EASY if it hurts STOP. Pain is your body telling you something is going wrong! Slow n steady is the best thing! Also if u rush to stretch urself you may end up ripping urself inside which can only be fixed by surgery, so just be careful :)

>>721

That's actually kind of what you need to do, a lot of the time. since what you are actually doing, as far as I can tell, is relaxing the anal muscles, or at least opening the sphincters.

The key is to practice getting control over those muscle groups. I can do that no problem, but other muscles groups in your abdomen can help you orgasm, which I don't have down yet.

Yes,
Lie on your side
Lube it good, then get a dildo like in the picture, put the end (20%) in your ass, then pull the dildo the same way you would make a lollipip pop out one corner.