Can't find a condom with an elastic ring that fits me!

Dear painfully pinched,

Oh no! That's quite the "condom-drum." Luckily, there are a variety of condoms available for you today, with new ones being introduced all the time! Also, not all condoms have the same circumference and some have more elastic "give" than others. As a result, it's a good idea to try on a variety, and see which brands and styles you like more than others. Furthermore, some condom manufacturers offer specialized sizes and styles, such as "large" and "extra large." However, this may or may not affect the rubber band elasticity. Additionally, it may interest you to know that several condom manufacturers actually market sized-to-fit condoms, offering a variety of sizes (between 55 to 95 different ones!) that correspond to different penis length and circumference measurements to create a custom size.

So, unless you really have tried every available brand and type of condom under the sun, and not just the few kinds usually available at your local drugstore, it may be beneficial do some extra research. You can get condoms in variety of ways, such as by ordering them by mail, over the Internet, or by visiting a sexuality specialty store. At a store, you'll have the bonus of getting direct customer service to ensure better matches for you. As silly, private, or embarrassing as it may seem, you can also ask around and see what brands have worked for others who've experienced similar discomfort with the elastic ring of the condom. With such a variety of condoms available, it's hopeful that you will find a condom that won't leave you feeling painfully pinched anymore. Once you have your new finds, give them a whirl and test them out, either on your own or with a partner, to get a sense of how it feels.

You could also try to remedy your condom troubles by experimenting with lubricant, as condoms with water-based lube on them can be both easier to get on and more comfortable. In addition, applying a dab of water-soluble lube to both the inside and outside of the condom (outside only once it's covering your erect penis) eases penetration, enhances comfort and pleasurable sensations, decreases friction, and reduces risk of condom breakage.

Finally, if you've truly exhausted every possible alternative and still can't find a comfortable condom, then perhaps you could ask your partner if they would be comfortable wearing the condom. If your partner has a vagina, internal (female) condoms could be an option. These types of condoms are effective against pregnancy and most STIs for vaginal sex. Additionally, internal condoms can also be used during anal sex. Remember to use plenty of lubrication, as the anus isn't self-lubricating. 

Hope this information helps solve your condom-troubles!