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Anal play help please

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Ok this may be a bit of a strange one for some. I 24 medium build male who is a little curious. I have started experimenting, well for a couple of years I have been trying to find new pleasures other than just jerking off with my hand. I have become increasingly interested in anal play. I sometimes tease myself with my fingers in my ass but don't really know what im doing and can not seem to relax. I am looking for a open minded female or convincing TS to help me find these new pleasures. I am willing to travel to meet such people as I shy to meet people in my area incase I get noticed by someone who knows me. Meetings must be very descreet and clean and to begin with gently. This would be my first time with someone else under such circumstances. I would love for some one to teach me the how to be pleaseured anally and even be penetrated by strapon. Not too big please as I find it sometimes painful.
I hope to find someone who can help me with this. xxx martin.