This letter was originally published May 20, 2004:
My problem can be summed up in two words: Hate condoms. I'm a straight male college student who recently broke up with his girlfriend of nearly two years, and I'm finding it hard getting back out there to play the field. My ex was on the pill, so I never once had to use a condom when I was with her. But now that I'm getting with random girls, I'm forced to wrap the tool. And for whatever reason, when I wear a condom I cannot come. I have no problems getting it up, but pulling one off is the problem. Any words of wisdom, ideas, tips, etc.?
Insert Witty Name Here
My response after the jump...
My answer summed up in two words: Suffer, bitch. Until you have a steady girlfriend—until you're with a non-random, pill-poppin' woman you trust who also trusts you—you're just going to have to settle for wrapping the tool and a sub-optimal sexual experience. Explain to the next random girl you're banging that you have a hard time coming with a condom on and that you'll have to "finish yourself off." Then fuck the random girls until they come, pull out, take off the condom, and finish yourself off with your own right hand.
This is sub-optimal, as I've already pointed out, but there are always trade-offs, IWNH. When you're in a sexually exclusive LTR with someone who doesn't have an STD and is on the pill, then you don't have to use condoms. When you're with someone random—and enjoying the kind of thrills that only random sex provides—you do. If you really hate condoms, if they absolutely ruin sex for you, then you have a huge incentive to get back into a stable LTR with a nice, pill-poppin', non-random girl.