Great thread, thanks to everyone who’s shared their stories here, particularly JohnAMacdongnot and Rhuard29. Regarding JohnA’s account, my inclination would have been to go to dinner with her, out of curiosity and as a sort of adventure. But I’m not saying that he should have.
The part of JohnA’s story about the lady bringing condoms that were too small triggers a similar (but lighter) memory that I’d sort of forgotten.
It was my first appointment with a certain SP. When it was time for the condom, she brought out a box of Magnum condoms, which I have to admit were too big for me. That first session with her was amazing, except that I kept worrying that the condom was going to slip off. I had to repeatedly reach down to pull it back on! A bit of a distraction, but she was so hot and the sex was otherwise so incredible that, afterward, I was just thinking about how wonderful she was and sorta forgot about the condom problem.
So I saw her a second time. When she pulled out the Magnum box again, I thought, Oh shit — I forgot about those damn Magnums! But I was horny and couldn’t be bothered to complain, so on went the baggy Magnum. Again it was an amazing session, so, after it was over I again was just focused on all of the positives and forgot about the condom issue
So I saw her a third time. Yet AGAIN she pulls out the Magnum box. Again I just go ahead and fuck her with this stupid loose condom. But this time, after the amazing sex, I explained to her that the Magnum brand is too big for most guys and, by continuing to use them, she was risking having a condom accident of some sort. She was a sweet newbie and just didn’t know any better — I had been one of her first clients. A condom was a condom to her.
After that, she provided regular-size condoms, and I got to have fun without worrying that I was about to slip out and accidentally have unprotected sex with her.
Yes, I know, we clients should have our own condoms on hand for situations like this.
The happy ending to the story: that was years ago, and I’m still repeating with that beautiful woman now. And she’s still amazing.