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I had quite alot of problems getting things to fit properly when my girlfriend and I got together.
perhaps the cross-sectional area of my penis is larger than average, as I do find regular condoms a bit snug.
put some lube (or saliva) on yourself before trying to put a standard sized condom on, it should make the process smoother and give you a better "roll out"
get some good lube that is compatible with latex condoms, of course. personally, I never liked any of KY's products, I found ID and some other brands online to be much better....just go to a condom store and buy a bottle.
make sure she's plenty in the mood, make sure you dont try to just jam it in.... I cant help but be reminded of when my materials science professor brought silly putty into class.
when you apply a force to silly putty over a short time duration, it behaves like a brittle material, but if you increase the time duration that the force is applied, it behaves like a liquid.
I'm sure the fleshy parts of the human body are much the same way.
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