He wanted her opinion on the dress he was thinking of wearing on his first date as a woman tonight still not feeling fully confident in his own opinions about women's fashion.
Mary just looked at her brother standing there in a red dress that barely covered anything and said oh not enough which really surprised him as he thought he had done a really good job.
Mary just stared at him not knowing where to start trying to be as tactful as possible about how slut he looked with his tits practically falling out of his top and the very short hem of his dress that barely covered his crotch.
She just said to him with a rye smile on her face why don't you just borrow one of my dresses I think that one's a little bit too small for you I think you must have gotten the wrong size not wanting to tell him that dress would definitely send out the wrong signals and he would be fighting off creeps or night as she watched him slip out of it and pad across to her room.
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