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If he's that embarassed to buy condoms, then he is too immature to be having sex!
Have you ever heard of a small town? Not all of us have that luxury. Live in a town of 400 and everyone knows what brand, size, and flavor you're using. I used to buy my condoms two towns over; someone may recognize me but it's better than buying condoms from my math teacher's wife.
There's an unwritten rule with self check-outs that the moment you try and scan something even remotely personal it screams 'UNEXPECTED ITEM IN THE BAGGING AREA' at you and all the check-out attendants have to come and help you.
Plus they can see what you're scanning. It's on a monitor at their station.
He does not seem ready to have sex. Imagine if this guy was ever a parent
Why don't you buy them instead?
Hey OP tell you boyfriend to buy a birthday card when he buys condoms. People won't judge him as much. Or just buy them off Amazon.
Oh that's nothing. My uncle was embarrassed to buy just condoms on his wedding night, so he grabbed a random item off the shelf to buy with them. That random item happened to be a bottle of Vaseline. :D But anyway OP, I hope you didn't actually go through with it if he wasn't going to use some (legitimate) form of protection. It's worth it to save your virginity for when you're both prepared.
Get a real man who can handle his meat. And package it. I mean I can use more puns if it's not awkward yet.
Keywords
If he's too embarrassed to buy condoms, he's definitely not ready for sex.
Sorry Op but if either of you are too embarrassed to buy condoms then you are not ready for sex.