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ORIGINAL: shalin

we have done all the prilims adn use astroglide and stimilation and smaller insertions how long before we can actually do penetration?

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ORIGINAL: Hillwilliam
...........If you want to do it lots, make it so she likes it.

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Loosen up however you need to, if you need to. A small toy, a finger, a thin carrot, whatever. If you use your finger, or borrow one, make sure the nail is trimmed and clean. You or your partner might even work up to two or three fingers prior to taking his penis. You'd be surprised how much the ass can be stretched if it has been trained, and the stretching has been gradual. (One of my Favorite Clips)

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ORIGINAL: ChatteParfaitt

Using FR:

I love anal, but then I'm with someone how knows how to do it. You really can't use enough lube, and if the s-type doesn't at some point relax, they won't enjoy and the potential to harm them (through tearing) is great.

One major tip is that you must force the end of your penis through both anal rings. Unless your penis is really tiny and thin there is just no way to ease it in there. Trying will just make it more painful. So lots of lube, force it in, then stop. No matter how good it feels wait for the s-type to relax and start pushing back. Let them set the pace until it's obvious from the screams of bliss that you can move forward, so to speak.

BTW: If the s-type is terrified of anal, (after a first bad experience or just because they are), you do need a lot of prep to get them used to being relaxed with something in their ass. I think a well lubed finger or two is fine for this, but dildos and vibes can also be fun.

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Original: Epytropos

As to your question, have done it with toys before, mostly because I refuse to do anything to a sub that I don't know the feeling of doing to myself or having done to me. No prep - lube, insert, sodomize - and it wasn't nearly as bad as everyone (read: het females) make it out to be. It hurt at first, no question about that, but it certainly wasn't life-shattering pain by any means.

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Original: Arturas

Well. Anyone can do anal. What we do is "sexual magic" here. So, let me ask you if the "prilims" include the following minimums:

1) He has blindfolded you in a black silk scarf and bound you nude on all four bedposts with at least red designer bondage tape or preferably clean white nylon rope wound at least five times around each of your appendages for security while allowing the required bloodflow to your tiny toes and fingers.

2) He has properly flogged you over an hour while he plays his old Slayer CD loud enough to cover your screams earned during said flogging while interrupting this flogging perodically with evil unshaven beer bellied and smelly southern Mississippi jailer threats and perhaps wanton sex acts perpetrated on the innocent young maiden totally in his power.

3) He has carefully but sadistically actuated your new marks with his clean and beautifully chromed Wartenburg Pinwheel while watching you jump delightfuly within your tight restraints.

4) He has contasted the just hot enough but not too hot wax applied to your back side, likely writing his name or something else that occured to him at the moment, and then contrasted this with crushed ice to cool things off a bit and make a most pleasant but delighfully scream somewhat different from the ones he earned a moment ago with his flogger.

5) He has donned a strangely colored condom that glows under the purple light he mounted just over you and applied a liberal quantity of his favorite warming lub and then your saliva as he grabbed your hair and forced you to taste test his favor flavor lub. Oh yes, my favorte part, I am a hair puller and use that handle liberally throughout the night. Oh yeah.

Now that you have verified he is wearing a condom with your no doubt wonderful oral sensitivity (remember, you are tightly bound and blindfolded and since you cannot hear a condom, especially over his old Slayer tracks, the only sense left to you is taste, oh yeah) you are finally ready.