I have done it with 4 different shemales, one time with two.
But it is the risk of being found out that gets me most. I have a son that lives with me who would not understand. So I have to schedule adventures when he is out of town or something.
Also, the times I have done it were all pay times. I would rather find someone who I could maybe build a relationship with than a pro, but maybe that is a wrong assumption.
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Only 3 times so far.
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