Getting a tit job from a woman is best when she's wearing a bra or bikini top because it holds her breasts together for your shaft to slide between her boobs, and leaves her hands free to play with you. Especially when she's on her back and you are getting your TJ astride her.

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No personal experience of this but I used to chat to an aquaintance who told me that he had a girlfriend who used to basically get her kicks from teasing him with her naked body and then leaving him unsatisfied. He told me that when he decided to finish with her it was during a long session when she had repeatedly denied him any release so when she decided the session was over and went to the toilet he picked up her bra and quickly shot a massive load into one of the cups. She returned and put her bra on! He said the look on her face was almost worth all the aggravation!

Not exactly. I had a girlfriend who masturbated me with her panties while she was wearing them once. It had the same effect of my cum soaking through the material then she rubbed her clit till she came through her cum-soaked panties. On another occasion, a friend jerked me off and we got her bra wet then she put her blouse on over the wet spot. All night long we waited for the wet spot to be noticed by someone but no one ever made a comment on the small stain on her blouse.