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He fucked her at least 600 times during the 10+ years and he ALWAYS made sure he finished inside her pussy.
Even the very first time we met and had all agreed that even though the wife doesn't like condoms, he would wear one at least the first few times.
Well, that did not happen as there was instant chemistry and he entered her without one and wound up cumming inside her. I was stunned to be honest but also naïve( as he was the first time we met someone for sex) and to caught up in the excitement to say anything( most likely would not have mattered at that point anyways) until I saw his checks tightened ,grunting, then I knew it was too late.
When I did mention it, they looked each other and said they were "sorry" and just caught up in the moment.
Then they wanted to get together the next day also and we all agreed. Then he asked me about should wear a condom and I admitted that it was kinda late to worry about condoms and I had to admit that I actually loved watching and fucking her after he had ejaculated in her.
So for the next 10+ years that's exactly what happened,so we all wound up being happy, very happy