CARNAL NATION

First of all: stress. Totally a bummer. I commend your avoidance of pills, unless absolutely necessary. Good for you for turning to sex instead of traditional American habits like shopping, alcoholism, or TV to help you unwind. Drinking lots of water and getting lots of good sleep will help your boner for sure.  Starting sex more slowly and teasingly, breathing deeply ‘into’ your cock and being willing to slow it down and build up the action again can all help you keep it up. You can also practice jerking it with a condom, to get used to staying hard with that sensation, though I won’t hold it against you if you ignore that suggestion. Just a thought.

But if you want a quick and dirty fuck—and you want it now, some external assistance could be helpful. If you live within reasonable proximity to stores such as Early to Bed (Chicago), Good Vibrations (Bay Area, Boston), Madame S Leather or Mr. S. Leather (San Francisco), Babeland (New York), or Sugar (w00t to Baltimore), go there, take a deep breath, and ask for help finding a cock ring. Their employees are nice, non-judgmental, and they like to make people happy, especially people courageous enough to ask for help despite embarrassment. It’ll be a feel-good experience all around. If you’re still shy, think about what kind of material feels sexy to you before you go shopping. Will heavy stainless steel make you hot? Leather? Does something more low-key like neoprene sound more comfortable? Get what feels sexy but is also inexpensive enough that you wont be pissed if it turns out not to be what you're looking for. You might want to start with the cheap-o rubbery ones to check the fit.

As for sizing, there are some great tips involving a string and a ruler and pi (yes, as in 3.14...) on www.qtrading.com/cockring-sizing.html, as well as a handy-dandy sizing chart. Or just use your fingers; wrap them around the base of your cock and balls when you’re hard until you get pressure that feels firm but comfortable and then mark with a pen on your hand where your fingers meet. In the store, refer to your measurement for sizing. If you are interested in DIY cock rings, look up CBT (cock and ball torture) rope bondage: with a soft, fat shoelace and a slipknot you can easily adjust the fit yourself—just keep some safety scissors handy. If you have some girth to your package, try cutting the inner ring out of a female condom.
 

Reading your question makes me wonder: if you can’t talk about a cock ring in a sex-toy shop to a person who sells them all day and who you never have to see again, how will you introduce a cock ring to your lover?  Embarrassment is a fancy word for fear.  Get over it!  Whatever part of your brain that inhibits you talking and behaving openly around your sexuality is not your friend. Here's a fun idea: bring your lover with you when you go to the store.  Shopping for sex toys together is sexy! 

In my personal experience with cock rings, I started by tying a shoelace around my cock and balls. It worked OK, but it looked tacky and kept loosening. Then I tried a piece of silk—looked better but still wouldn’t stay tight.  At the supermarket, I found elasticized hair ties. They came in cool colors and were soft; they stayed tight and didn’t pull pubic hair.  Then I bought a mail-order leather strap with snaps so I could adjust the tightness. Very butch. Then I bought a three-size set of rubber rings.  Finally, when I knew what fit me, I bought a metal one. Have fun finding what’s right for you.

Reminds me of a funny story my father liked to tell about a guy having an affair with a wealthy, wild, sex-hungry woman. She decides to buy him a solid gold, bejeweled cock ring but can’t find such a thing in any store. (There isn’t a sex toy department at Cartier or Harry Winston, you know.) So she brings him to an old jeweler her family has purchased from for years and years, in the jewelry district in New York. They show the jeweler a design: it should be round, about 3 inches in diameter, with jewels on the outside. The jeweler asks what it’s for?  “A baby bracelet.”  He looks at them, winks, and in a heavy New York-Jewish accent says, “Really? Because it’s just the right size for a cock ring.”

Don’t be so quick to discount the pills. The erectile-dysfunction drugs aren’t just for those who can’t get it up at all. The secret the drug companies won’t officially tell you is that they have a very positive effect on the rest of us. It’s a bit like being 18 again but knowing what you know now about sex.   Many (most?) doctors have free samples from drug reps, so you might want to give better living through chemistry a try.

If you do still want a cock ring (and there is no reason you can’t do both or switch it up for a some variety), I suggest you start with either a leather one with snaps or a rubber one.  The stainless ones look good, but this is one case where size matters: too small is going to be painful and too big is not going to do the job. If you go with leather, you can use it to work out what your perfect size is for a steel ring. Measure the length of the leather strap on a comfortable setting (can you put it on and take it off without unsnapping it?), then take that length and divide by 3.1415926 to give you the minimum diameter of the steel ring you need. In most cases you’ll want to add a ¼ inch or so to that for comfort.