I would suggest more anal foreplay. More than one finger, or even a small thin vibe well lubricated may be a great way to loosen things up a bit before you attempt his penis. Also a couple drinks could not hurt. Being nervous and tense will cause you to subconsciously clench the exact muscle you are needing to relax.

__________________

The practice of putting women on pedestals began to die out when it was discovered that they could give orders better from there.~ Betty Grable

If I wanted your opinion, I'd remove the duct tape and ask you for it.~ Me
<~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~>
One man's dream is another man's nightmare~~~~> §¤ Lilith ¤§
~>My Scribbles<~
==>Gone Shopping<== ~Just a Quickie~ *~A Celebration Vacation~* ~Surprises~ Sleeping With the Window Open
What Did You Do Today? Self Defense Class ~Short Sweet Snippets~ § Summer Spin § Story Challenge Submission Pajamas