I remember a few times SP's that I was going to see would tell me they needed condoms, and since these were girls I knew, I would just offer to stop and grab some on the way. One time though, I was set to see one lady just after she arrived in town, and she texts to say she got here late, I was already on my way over, and she said she needed to go get condoms and some other supplies, could I push back an hour. I said "I'm like 10 minutes away, why don't I just come pick you up and take you?", to which she agreed, to my surprise. We ended making it a mini-date, we stopped for a bite to eat (I mean, I prefer sex first and food after but I had my doubts I was going to get her back out afterwards lol). The Shoppers nearby was one of those "closed by 10pm" stores, so we went for a bit of a drive. I asked if she wanted me to wait in the car or if she was OK if I went in with her. She said "I'm fine if you come in, but what if you see someone you know while you are with me?" and I said "I only hope they also notice the box of condom
I remember in high school working in a Mac's and the guys coming in to buy condoms and them making it those most awkward thing. And back then, they were behind the counter like cigarettes, so they had to ask. The amount of shit they would buy to try to distract from the condom purchase was funny. So here's me and "Tanya" and she buys the big box of Trojans, and a few other things and I'm like, "I'll carry those for you". Get to the front, plop them down on the counter and proudly tell the pimply faced kid working "Big weekend ahead".