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GreyMoggie -> RE: Ass (boi pussy) (6/19/2014 7:37:35 AM)
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MistressNeon's answer is as complete as it is accurate. I recommend Amazon.com or nawtythings.com for inexpensive, anonymous toy buying.
I'd add that you should be comfortable with your body and aware of what it likes, what it doesn't, under what circumstances these change and where your limits are. How is your top supposed to know what works and what to avoid if you don't have these basics down? For this, playing with yourself solo to learn about your own body is invaluable.
But to approach it without that, and to answer the question, a Master will be able to take it slow or make it hurt as he wishes and thinks is best for both of you. If he chooses a painful way, and a Sadistic Master probably would, you'll have to choose between putting up with it or calling red. But this is true whether you're an anal virgin or not. Negotiation and knowing what you want are important here.
Solo Anal Training:
You might consider starting with just your fingers as you shower. Make sure your fingernails are trimmed well, then take the opportunity to feel around your anus, it's texture and tightness, get to know it (it's also fun to see how it changes as you train, if you don't do this now, you'll miss out on what your virgin hole was ever like). After the shower, get on your bed on a towel with the lube, and a mirror, take a look, feel and watch yourself play, going only as far as is comfortable, easing a finger in and seeing how it feels. There should be no pain at all, and can listen to your body to know how far to go. If you feel a bit tight, push out slightly as if you were trying to poop - this relaxes the sphincter and makes it easier.
The next time take it a bit further, get out the anal training plugs you ordered, and insert the slimmest (probably finger width) lubed up, and see how it feels. Then masturbate with it in. I like to position it at my anus, and lie back to use my heels to push it in hands-free while I masturbate too - the sense that someone else could be doing it is a big turn on. Masturbate until you come, and notice the difference with having that pressure in your ass. The next time, or that time if you feel like it, try the next size up.
By the time you've gotten to a small butt plug size, you'll know you can take most cocks without creating any anal fissures from stretching. You might be tight at the beginning of the session, so squeeze out as you've taught yourself, start slow and you'll be fine.
With these strong foundations, as you get more experience you'll learn if you like a bit of pain, if you like stretching and want to get into larger toys, if you like it rough or smooth, and this will come to you naturally as you play.
FYI:
Anal fissures are tiny tears around the anus, that sting but usually heal quickly and well, just keep the area clean. What you absolutely want to avoid is puncturing the rectum by roughly shoving pointy things, including overlarge cocks up it very hard and/or at odd angles. If you have severe internal pain with bleeding, or have any question that this could have happened, call red and get to a hospital immediately. Rectal punctures are be fatal if not treated asap.
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