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I'm the same way, so you are not alone. I tried a few different makes/models all to no avail and finally gave up. I do recommend that you try different ones even if you have to order them.
Another thing you should do is to apply some lubricant to just the glans of your penis. Doing so will give it more wiggle room and transmit more friction. This might very well be all it takes to solve the situation. Regardless, do it with all condoms you use.
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We normally recommend that teens use three forms of contraception because of the high likelihood of becoming pregnant. Yours, hers, and ours. If you do not use a condom, then at least use a spermicide in addition to what she chooses to use.
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