Skirts and Heels 2: TRANSGENDER, CROSSDRESSING

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Set in the early 2000’s, Jeremy Clarkson is a desperate man. He took an ill-advised joy-ride in a stolen car a few years ago which landed him in jail. That would have been punishment enough but as an ex-con no-one wants to hire him once he gets out. Having no money left, he is made an offer than he can’t refuse. He can work for the demanding boss of an exciting new fashion house. She is willing to give him a chance but she does have some mysterious conditions. Jeremy, though has no choice and agrees. Little does he know, that the mysterious conditions involve him getting rid of his scruffy beard and dirty torn jeans for the dainty makeup and low-cut dresses of a fashion model. Jeremy goes along with the ruse initially – it can’t be worse than starving to death. But when male models and high-powered men start taking an interest in him, will Jeremy be able to keep his new skirt and heels on?

In the second part of the series, Jeremy continues to be the demure and accommodating assistant to Camilla. Camilla too takes a shine to the newly minted young woman and takes her under her wing. Camilla shows Jennifer (Jeremy) the ropes in both the corporate world and the world of women. Jennifer is hesitant at first but slowly starts to open up to Camilla and begins to enjoy being a woman. But when men start hounding her for dates, will Jennifer come clean and admit that she is really a he?