The thing about condom-buying is the embarrassment fades the more often you do it, because in truth, the cashiers really don't give a shit unless the person buying them is really young or really old. What does get the raised eyebrows and in turn, a red face and fluttery stomach, is buying larger-than-normal amounts of condoms...
Not getting any in my life, I nonetheless buy the things on a fairly regular basis because it's cleaner and easier ro rub one out into a creamcatcher than kleenex or a sock, so I'm pretty much going through a 36-box of lifestyles every two to three weeks. That gets expensive at $17 a box. No it's not "oh shit I have to switch from Heinz to store brand ketchup" bank-breaking expensive, but it is $300 a year compared to a sock you had to wash anyways. Anyhoo, these 36pk boxes go on sale for $10 or $11 at my local drugstore some times, and when it does, I tend to stock up on three or four boxes at a time, and standing at the checkout with 144 condoms does get you the funny looks.
Speaking about funny...