It had been over three months since the great shift turned Jessie into a woman and luckily he was about the same size as his sister who was unshifted so he could share her clothes which was a great help to him.
He just stood there with his hair in curlers dressed only in a bathrobe after his sister did his makeup for him staring down at the sexy panties his sister had just handed him stunned for words when she said they might be uncomfortable but they're sexy just in case you get lucky tonight.
It was something he had not really thought about but he was a woman going out with a man and there was a possibility he could end up in bed with him which was only natural for a heterosexual woman and a heterosexual man.
Which frightened him a little bit as he was not sure he was ready for that.
He slipped on the uncomfortable underwear and squeezed himself into a form fitting dress and uncomfortable high heels that made him feel like he was wearing stilts just in time for his boyfriend to pick him up.
He was even more surprised when his sister kissed him on the cheek and said I won't wait up for you & there is condoms in your handbag have fun little brother.
When he returned the next day his knickers were bunched up in his handbag and he was practically glowing as his sister nagged him to tell her everything that had happened.
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