What does it mean when someone says an orgasm is not pleasurable?

When women orgasm during rape, it is more humiliating and the humiliation stays with them longer. It becomes a block for them to gain pleasure during sex (orgasm or not). The trauma nags at you years or decades after the rape (orgasm or not).
This. I was made aware of it by someone who experienced it. At 17, 3 men gang-raped her for hours. Toward the end she had several orgasms. It took her years to come to terms with what happened and to trust enough to allow a man to help her orgasm. The first few times she did with her boyfriend (later husband) caused her to go into hysterical crying because of the guilt and fear from those during the rape. She associated orgasms with pain and something being taken from her. So yeah, not pleasurable at all.

Comshaw
 
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