I enjoy it with the former, but not the latter.

As far as enjoyment, it does have more sensation, and the kinkiness of it is a turn on, at least at first.

After performing it with a number of gals over the years my feeling is that it is nice, but nothing to get that excited about.

Watching the gal enjoy it is probably the best part of it.

By the way, the easiest postiion for insertion is with the gal on her back with her legs wrapped around your neck. You can also watch her face and play with her vagina in this position as well.

As far as lube goes, the more the better.

Before you criticize me, let me first off state that none of my SO would let me do greek. They tell me its unnatural, so I gave it up. Even when offered greek with a couple of providers, I passed.

Now however, I am curious about it and want to try it. A few questions: is lubricant necessary? How does it feel, i.e. is it tighter than vaginal? Is there certain parts that I feel in greek? How deep can I go? How should I start off, slow like vaginal and work through it? Does size makes a difference? I don't know what regular means, so, providers can shine in on this. Does girth makes a difference? Does length makes a difference? Can I cover most positions with this?

I would assume providers would properly cleanse themselves before greek. Is it worth the extra fee? Does it make you feel different after the session? Again, I have never done greek before, and any insight would help. Thanks!

I am a greek provider - I typically get this service requested with more of the PSE visitors than the GFE though it is available for anyone.  I have a personal limit on how many greek sessions I will provide in a week and in my sessions it is greek to complete - typically in the doggy position (guys choice)

With that being said, I always use ample lubricant to avoid any potential tearing and make the ride smoother. Size does matter and some providers want to see what is in store for them before offering the service. Initially,no matter who I am with, it is painful for me, however, converting that pain to pleasure is what makes the experience.

As far as cleanliness,always be clean - and of course you are using a cover - though I typically start in one place and end in one place HOWEVER on the GD board right now there is a discussion on how to move safely from vaginal to anal.

Some of your other questions, you will have to experience and answer yourself. In my civie life, I have had some people love it and some not into it. To each their own.

Good luck!

Have fun and play safe!

Summer

of providers in your area who offer greek and find one who turns you on.  An experienced greek provider will help you happily cross to The Dark Side.

Then I started to get the urge to try it. Take my advice, that urge won't go awy when it starts. The key to good greek is preparation and patience. Manicure your nails, bad nails that have rough edges can cut the flesh. Use a water based lubricant and take a thin, clean latex or non latex plastic glove with you. The glove helps protect against your nails and makes the lubricant more effective.

Start the greek session by picking a women that has good hygiene and is ok with greek. If you ask and a woman says no, end things there. If the woman says yes, put on the plastic glove and lubricate your index finger. Gently work the lubricant into and around the inside edges of the woman's anus. A tight muscle exists in the anus, you must slowly and patiently loosen up that muscle enough to allow you to slip your lubricated, covered penis in. In my experience, I require ten to fifteen minutes to loosen a woman's anus up enough for me to slip the tip of my penis in. Once you have the penis in, pull it out and quickly lubricate the entire penis and put lubricant a little deeper in the woman's anus. Don't take more than thirty seconds to do all of that. Slowly move your penis deeper in as the woman's anus loosens up, be gentle. At some point you will be fully in or in as deep as you can go, note that point. Once you are fully in start stroking. As the woman loosens more and gets into the session, you can increase your stroke rate to the point where your tights are slapping against the woman's ass. If a woman can't take all of you be careful with the stroke distance, you can seriously hurt her if you are insensitive to the depth limit that she naturally has.

There is no better and intensely satisfying sight for me than having a woman go nuts with passion as I give her greek. Many women have the most intense orgasms possible during that act.

I had this on my list to try because of the curiosity factor.  I remember walking out saying to myself well I tried that and it wasn't worth all the hipe.  Granted I'm sure the experience varies by lady.  My lady did greet me at the door asking if she could be my ass slut.  I seleted her because it was on her menu for no additional charge and thought if it happened it's a bonus.  I didn't request it but she must prepare for it for every client and offer.  Assume there is prep time because i see guys say in review the girl is up for it if advance notice.  Give it a try, just one guys thoughts

To answer your questions
Yes plenty of lube and my provider handled the application and cover.   Go in very gently and increase your stroke.  My provider started out with standing doggie for the first insertion and later in the session she monted me.  Either way don't forget the lady will most likely require a change in covers between holes.  i.e no mix and matching for sanitary reasons.  I didn't notice any tighter feeling or I'm in and I'm going to cum in 2 seconds feeling.