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When I want to make trans Sims, I either change the sex through cheats or give a male-bodied Sim a feminine face. Also, the makeup on the eyes should go all the way up to the brows, with a tattoo on the upper arm "Boss". He's probably kinkier than me. I could be wrong or it could have been a mod. They're often items that the females can already wear. There is female to male converted clothes. People often make custom content for male sims that look like female clothes.
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