TS Amelia requests you wear a cock ring and no underwear to see her. Is this particular to her? I wouldn't know the first thing about how to buy one, how are they supposed to fit?

sounds like a fun request.  any adult entertainment store.  get the high tech polymer versions, don't want to have to call paramedics or show up in er with the metal ones.  snug is all i can say.

Sounds like a fun request, but why would anyone make such an explicit request on email or phone....sounds too risky.

if a t wants to get a real long hard fuck she may think a cock ring will keep you up and loaded, if you have experience with it then it may be the ticket. The rubber or strechable ones are easy to start with, metal is cool but sizing can be troublesome. adult stores and internet suppliers are the place to shop. Get several as one can easily break when putting in on if too tight, but if not tight enough it will slip off. Most guys put them on when they think they will have trouble keeping it up, but they always look cool, especially the ones that trap your balls in an iron ring, but practice first to no miss the fun

I think they look cool and I would imagine they feel cool, but if possible, could someone provide an in-debth education: Cock Ring 101?

http://www.intimateattitudes.com/ia_education/edu_erection_rings.php

just this once, after that you get scolded for not making a little effort