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What do I do if my Mistress wants me to have sex with a man but I don't know how? 
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Tinker
It is still up to you what you want to do.
 
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SissyMimi
I think I want to, but I am afraid it will hurt.
 
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Ellie Jean
@ SissyMimi
  I suggest practicing with a dildo first; I have a couple that I practice with; a 7 inch one and a 10 inch one. Be sure to have lot of lube handy; makes it way more comfortable. Once you're confident in your skills with the dildo(s) you can try it with the real thing with much less worry. Hope this helps!    
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