Greek

Your 1st.... 2nd.... hell even 5th time shouldn't be with a hobbyist, or as a business transaction to be more specific about it. It should be in a comfortable & relaxing environment.

Mildly educational reading
http://sexuality.about.com/od/analpl...sex_how_to.htm
http://www.yourtango.com/200681/anal-sex-for-beginners

Your 1st.... 2nd.... hell even 5th time shouldn't be with a hobbyist, or as a business transaction to be more specific about it. It should be in a comfortable & relaxing environment.

Mildly educational reading
http://sexuality.about.com/od/analpl...sex_how_to.htm
http://www.yourtango.com/200681/anal-sex-for-beginners Originally Posted by Dorian Gray

I can see your point with the first and second time, but my 5th?
I'm a little confused.
I asked for advice on making it easier not whom you think I should try it with.

PLEASE NO NEGATIVE COMMENTS
THANX IN ADVANCE

Get a finger or two up there first. Some chicks use toys I think that would probably help.

Butt plug.

Get a finger or two up there first. Some chicks use toys I think that would probably help. Originally Posted by Trey

I will definately try doing that.

DG don't know what he's talking about!
Of COURSE you want your first few experiences to be with hobby guys!
Think about it, do you REALLY want a guy that's gonna take his time and wanna do it all night or do you want a guy that knows he only has 10 minutes left on the clock?
The hobbiest is gonna get in there and get out, not take their time and stretch you out for hours on end, that would just be uncomfortable for everyone.

Maybe make sure your first few hobbiest are people you have seen and know are somewhat size challenged. Some of us can't even challenge those toys you will buy lol.

DG don't know what he's talking about!
Of COURSE you want your first few experiences to be with hobby guys!
Think about it, do you REALLY want a guy that's gonna take his time and wanna do it all night or do you want a guy that knows he only has 10 minutes left on the clock?
The hobbiest is gonna get in there and get out, not take their time and stretch you out for hours on end, that would just be uncomfortable for everyone.
Originally Posted by riday

lmao you are so silly
But good point though.

To clarify why I said to wait on/severely limit the Hobby Greek IPO is to build tolerance. You yourself said the 1st time didn't go so well. So the 1st few different dicks you should offer/try it with should be someone you are VERY comfortable with. Civi fuck buddies typically may be better, though you can use a client. One reason is the build up will take significantly longer. I don't think most clients will have the tolerance to spend 30-45mins on prep work to loosen your mind and sphincter. Also they'll want you to be tolerant to accepting varying sizes of cock once you do offer it. Not to mention once you do there are those whose sensibilities basically come down to a quarter size dollop of lube. Have a dozen prep strokes with a finger or small dildo. Then ramming their dick in your ass like a plunger.

For all of you that want to know what Greek feels like, lube up a broomstick and shove it up your arse.

It was meant for crapping, not fucking. Unless you are a fag! They only have two choices. Mouth or ass.

To clarify why I said to wait on/severely limit the Hobby Greek IPO is to build tolerance. You yourself said the 1st time didn't go so well. So the 1st few different dicks you should offer/try it with should be someone you are VERY comfortable with. Civi fuck buddies typically may be better, though you can use a client. One reason is the build up will take significantly longer. I don't think most clients will have the tolerance to spend 30-45mins on prep work to loosen your mind and sphincter. Also they'll want you to be tolerant to accepting varying sizes of cock once you do offer it. Not to mention once you do there are those whose sensibilities basically come down to a quarter size dollop of lube. Have a dozen prep strokes with a finger or small dildo. Then ramming their dick in your ass like a plunger. Originally Posted by Dorian Gray

Wowzers. So how many times have you tapped out? if I'm misreading then my bad. ;-)

You definitely want to take DG's advice. Start with someone outside the hobby you are comfy with. This will give you a chance to figure out how to mentally, then physically relax first. Lots and lots of lube. Also, you have to know whether your digestive system is going to behave or not, and adjust your prep work accordingly.

Requirements:

Relaxed mind
Relaxed body
Clean pipes
Tons of lube
Digital warm up
Toy warm-up

Do not proceed until you are to the point that the toys are actually an enjoyable feeling for you.

Eventually a pro (like me...lol) doesn't need warm-up, just lube. When it's time, I just use my Jedi powers to relax my body and enjoy