Learning to wear a thong

Timothy's friend tutors him on how to be a girl

After Timothy came out to his best friend Sandra she offered to help him learn more about experiencing the feminine world and she took her job very seriously. Now as she helped him prepare for an evening out together he wondered just what he had got himself into.
Timothy shuffled from one foot to another as Sandra slid the denim mini skirt up his hairless legs. The coarse material rubbed against his smooth skin and but it the thong panties he was wearing that were giving him the most trouble.
"Do I really have to wear this?" he whined. "It's riding right up and it tickles."
"You said you wanted to experience being a girl, and we girls often wearing thongs because they are so sexy. You don't want to go out wearing Granny panties, now do you?"
"I suppose not," Timothy sighed. He ran his hands through his hair and tutted to himself.
"Just give it some time and you will forget that it is there," Sandra assured him. "Now hold still I want to see how you look in this skirt."
Timothy was already wearing a lacy crop top that Sandra had lent him but the denim skirt looked tiny. As Sandra pulled it around his waist he was shocked to see that it only just covered his bottom.
"I can't wear this, it is far too short," he complained. He was sure everyone would be able to see right up his skirt.
"Nonsense, it looks very sexy," Sandra giggled although secretly she did think it was a bit too short. Even she would never wear it in public anymore but she felt it would teach Timothy a lot about how exposed a girl can feel. The skirt was quite narrow and the top of Timothy's thong was just showing over the waistband. Perfect! Now all they need was to find him some high heels and he would be guaranteed to turn every head in the room...