Feminized waitress

Ian looked cute as a waitress

It was Ian's idea that his girlfriend Sally try dancing on the bar to get more tips but when she sprained her ankle she held him responsible. Sally worked as a waitress in a night-club and she wasn't prepared to miss out on a week's wages until her ankle was strong enough for her to work again. That meant Ian was going to have to fill her place.

He has to fill her shoes

 Ian wasn't at all keen on the idea of pretending to be a woman but Sally was so upset that he went along with the plan. She carefully waxed his legs and body and plucked his eyebrows. However, once Ian tried on her waitress outfit he finally realized just how sexy and exposed it really was. The dress was pink with layers of frills and a very short dress. He had always told Sally that she looked good in it but now that he was wearing the short frilly little dress he felt very embarrassed. He had to admit that Sally had done a good job on him but the thought of going out in public like that made him blush. Sally was thrilled with her handiwork and was sure that Ian would get plenty of tips from the customers as long as he remembered to flirt the way she had shown him.

Being a waitress isn't fun

"I can't do this Sally," he said. "I can't be a waitress and walk around like this. Everyone can see up my skirt."
"That's the least of your worries," Sally warned him. "It's the hands that will be trying to get up your skirt that you need to watch out for..."