Fiction: Professor of Women's Studies

No, that really sucks.  No suspense.  Here we go again.  We need a female coach:

It was the sexy professor S__ who suggested that he start wearing women's underwear.  She would supply him with his first pair.  She never got it back.

Months later, R__ asked for more.  She gave him another pair.  Then, a bit later, he asked for a brassiere.  S__ asked, so you think it's working, do you?  R__ enthusiastically agreed, feverishly awaiting his new set of underwear like a mad scientist or a drug addict.

When he came back for more, S__ decided to take him shopping.  They went to a lingerie store, pretending to be a couple, and they bought lingerie together.  R__ was somewhat sheepish, and insisted on her buying it, and he would pay her back.  S__ agreed.  But she couldn't believe that he was actually wearing it.

S__ thought that this was pretty funny.  She was a vamp, and she wanted to figure out how far R__ went.  She began to flirt with him, to see, possibly, if he really wore his feminine attire.  She fondled him in his office.  He liked it.  She would now discover.

But he was reluctant to get started right away, right there on his couch.  She goaded him on, and he timidly acquiesced, and stripped down to a sexy little black panty and bra outfit.  He looked ridiculous.  S__ laughed.

"You need training," she stated, and began to show him the ropes.

She showed him how to shave his legs.  He also had to shave his body.  He looked much better now.  And sexy, too.  She only changed him gradually.  He started out with just panties and bra, carefully shaving often enough to not get stubbly.  Then he began to wear pantyhose, and then garter belts and stockings, and then teddies and lingerie.  He wore only women's underwear now. 

When I discovered him again, he wore a skirt to work.  He was embarrassed.  But he'll get used to it.

It seems these stories only need to end when the hero decides to wear women's clothes only.