The only condom that ever broke on me was a Trojan "Her Pleasure." Because I didn't yet understand that "my pleasure" was actually determined by my clitoris and not some barely detectable "ribs" on a condom, I felt doubly duped by Trojan's false promise of 98 percent effectiveness and—hello?!—Her Pleasure! Her pleasure? More like "her pregnancy!"
I stand against Trojan Her Pleasures to this day. This position is backed by the existence of far better condoms (see "Love Your Latex"), but it's also just plain superstition because realistically, Her Pleasures, like all condoms, are 98 percent effective in protecting against pregnancy and STDs, including HIV/AIDS.
When used correctly.
This is the part of the condom packaging people always tune out. It won't be 98 percent effective if you put it on your big toe. For it to work, you've got to use it right.
The first step toward 98 percent is knowing when to use a condom: as a backup to other birth controls like the pill. As a barrier between your mucus membranes/sexual fluids and another person's, whether that be via vaginal, oral or anal sex. Anytime you switch orifices or partners, use a new condom. Use condoms on toys like vibrators and dildos if you're sharing them, especially if they're made from porous materials like elastomer. If you have an STD, especially if it's incurable and deadly like HIV, always, always use a condom!
Don't store condoms for long in extreme temperatures (meaning in your car, wallet or pocket), and always check the expiration date before you use one.
Open condom wrappers carefully and not with your condom-ripping teeth, you vixen, you. And unless you've got removable dentures, don't put one on with your mouth.
In your hand, roll down the edge slightly to make sure it's not inside out —the rolled edge should be facing up on the outside. If you accidentally put it on inside out, don't just flip it over, because the outside of the condom could be "contaminated" with your partner's fluids, so start over with a freshie. Treat condoms like Lil' Wayne treats hundred dollar bills: carry them in wads. Use them often, toss them often. Don't be a cheapskate. Make it rain.
Put a few drops of lube in the inside of the condom to increase his sensation. Only put it on when he's semi-erect or erect. Some guys have a hard... or unhard... time staying at attention when it comes time to suit up. This is no reason not to use one. Try keeping the foreplay going while putting it on, or, if he's more comfortable doing it himself, let him do that. If he loses it, restart with a new condom to assure a proper fit.
Before you put it on, pinch the tip! This leaves space for his grand finale, which can bust through the condom if it's un-pinched. Keep pinching as you roll it down to the very base of the penis. Then run your hand from the head to the base to push out condom-breaking air bubbles.
Use lube during intercourse! It reduces friction, which feels better and prevents condom breakage. Only use latex-compatible lube. Water-based and silicone—yes. Oil-based—no!
If he goes soft during romping, pull out and start over or it could slip off inside, which is against the point (protection is the point).
When you're done, hold the base of the condom against the base of the penis the whole time he's pulling out. This prevents the condom from slipping off and spilling the stuff you were trying to avoid in the first place.
Take off the condom by gently pulling at the tip and pushing up the base simultaneously. Latex is elastic, so just pulling at the tip can make a satisfying snapping noise but also a huge mess. If you're using toys, hell—make it snappy.
Tie a knot at the end and trash it. Never reuse a condom! If you just got naughty by nature, think of the earth (and the innocent children trying to enjoy the park) and don't toss your used condom on the ground, sicko.
And just as overthrowing our government won't solve all our problems, doubling up on condoms doesn't make them 196 percent effective.