Pleasure and Pain.
while i am yet to experience sex with a shemale, i have put things up there (small at first, like my finger or a pen, but then moved up to larger stuff, like rexona deoderant cans covered in cling wrap with a bit of vaseline on it) and even though it hurts a bit, it hurts soooo good.
the most intense orgasm i'd ever had was when i put the can up there and fucked my ass with it, then i wanked off after taking it out. because it had massaged the prostate it was a very intense load.
sorry if this was T.M.I, but hoped it helped your question, and maybe turn some ladyboys on :P
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(ಠ_ృ) I say they seem to be letting all SORTS of riff raff into the internet these days!
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