Its easier to answer 'How' does it feel?
It feels amzing.
Penetrating most warm things with your dick feels amazing, for the man.
I've only really done anal with women before, my previous boyfriends weren't so into it - but we did it enough to know that there's little difference between a mans arse and a womans arse from the inside.
Its warm, but not very wet. Lube is usually cold and provides only slippage, not wetness. Its very different from penetrating a girl in some ways, more than you'd think. Same for oral, its different.
To sorta list the differences, (Not going to dwell on it, I know its not strictly on-topic) Oral is very, very hot and warm, but isn't exactly penetrating unless your partner can deepthroat and not many can. There's a tightness at the lips and another sense of something hitting your bellend as/if you hit the back of their throat.
Vaginal is almost always warm and wet feeling, even through a condom. No matter how aroused a girl all that does is make her easier to stretch without pain, her insides will always clamp down around you without missing a centimeter. It might not be tight against you, but you always feel this sense of being 'surrounded' by flesh and most of the pleasure for me comes from rubbing the 'lip' of the head of my cock - the sensitive part - against the insides.
Anal is a hotter feeling, but its only damp on the inside, not wet. It has a very similar sense of being 'surrounded' by flesh, but its overwhelmed by the entrance. When you push in to an arse you feel the tightness of the hole mostly, the rest is just a fairly pleasant place to keep your cock, but the tightness of the entrance is what gets you, its like a really tight-fisted handjob. Pushing in, so long as you've got a fairly smooth, even cock, once the head is in, the whole shaft pushes in carefully with an even tightness.
Final thoughts, with anal, I prefer to keep most of my length inside the whole time, moving only the last 2/3cm of my cock (about an inch) back and forth. Half of that movement is absorbed by the flex of my foreskin and the condom so actually I don't move against the entrance, I move so the two sleeves stay still and doesn't disturb and cause additional discomfort.
Only my experiance, but the less you move against the actual arsehole the more the partner being penetrated prefers it. Feeling you move around inside is enough, without having to actually thrust in-and-out.
Remember that professional pornstars spend upwards of an hour before an anal scene undergoing several stages of foreplay and enemas and are trained/practised at remaining widely dialated for hours. I've never done hot-dogged fast-paced thrusting monkey-sex and probably never will, I'm not honestly sure amatuers like myself often or ever do that.
If this information is for a fanfic, I'd advice doing what most people do with romance, drama, sex and sexuality - don't base it on real life or try to make it factually accurate, because real life is often a bit of a let-down ^^
PS: Again, everything I've written is my own experiances and could be very different to the views of other people!
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