I'm no sex expert, but I think I can answer these...
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1. If I ejaculate....can I continue to go at it without fear that some will leak out?
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Not really, whenever I've used on it will start leaking almost immediately. When you put it on make sure there is LOTS of room at the tip, I usually roll the condom down and then lightly tug the top and roll it back down. This is so when you cum there some place for it to go besides out the condom. Once you cum you can SIT there for a few seconds, but make sure you don't lose your erection or it will leak.
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2. If not, is it safe to take it out, wash it off, put another condom on, and go back at it?
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Don't see why not. Just make sure you use a new condom and throw out the old.
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3. Kinda unrelated, but would the shower be a good place to have sex for the first time? (less mess? I dunno)
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Having sex in the shower is a pain unless you have a pretty big shower, just not enough room. Sex really isn't that messy, maybe a towel underneath if you are afraid of getting fluids on the bed.
Have fun!
Gariig