It's also gonna be the second overnight with two ladies, though this time it will be at my place, and not a hotel. Only the one girl is offering it so maybe the other girl can help me relax so I don't end up hurting the  one I'm taking the trip to the isles with. Other girl thought my size might be an issue, but the lady offering it doesn't seem to mind it, plus she said she'll take the lead since it''ll bee my first time at it. Any other advice you guys and gals can give, outside of using a lot of lube and to let her pace herself? Maybe something the other girl can do that might make it easier on the both of us.

Your concern is meritorious.  I would feel the same way.  Your desire not to hurt the provider shows your respect for her and that tells me you are sincere.  It goes without saying that a trip to the isles has to be a covered journey.  The risk of rough seas without cover is too great for both of you.  My suggestion is that her friend help by opening a passageway before you begin your voyage.  With a toy (comparable to your size) and lube, she can begin by softening up the area with her fingers, one at a time.  Then introduce the toy.  Short strokes at first will help ease the natural muscle contractions of the isles.  Once initial entry is reached and the isles are relaxed,  ask the friend to go deeper with the toy.   You will know when she is ready for you when there is no resistance to the toy. Switch positions with the friend and while covered and lubed, slide in slowly but not all the way. Rythmn is important as the contractions may mount as her pleasure mounts.  You may be inclined to go faster due to your own pleasure, as the isles have a different topography than anything you've ever felt.  Remember slow and deep and it will be smooth sailing for the two of you.

Damn........that was HOT!!!!!  EOM

But obviously your concern is valid and proof that you are a gentleman!

You sound like you're facing some kind of medical procedure.

Relax, it's fun as hell, like a really tight pussy.

And I'm sure she is a pro at it and knows what to do, and maybe will enjoy it even more than you do.

Remember, we do this to have fun, not to have more stuff to fret over.

Slow and deep is not how all of us like it ... Everyone is different.  

will never understand the appeal of butt fucking when a willing pussy is just inches away !!!

Thank you brilove for correcting my post as it refers to depth.  It is an excellent point and I wouldn't want to see anyone hurt.  I think I got a little ahead of myself!