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If you can trick your mind into always believing "you are great" - your actions and assuredness will follow suit. This position is usually the least "painless" to be penetrated. LOL I'll try to cover this subject as exacting - "as professionally" - and as lady like - as "Renee" can. Good luck and happy birthday. Wanting to add to her pleasure. One frustration many t-girls come to know is how difficult it is to develop friends who don't have a private sexual agenda in mind. However, if you're relatively new to transgender related sex issues, you'll certainly walk away with some fresh perspectives. If you can grip it's width with a single hand, you task will be much easier as it is far easier to "squeeze" all at once.
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