Oh man, I used to place CE ads on Craigslist and while for the most part, it was a
huge waste of time for a straight cis guy, I did meet someone I hooked up with a couple of times but that was it.
However, I did receive a few responses that stood out.
I once received a response from someone who claimed that they were looking to start a family and had run into issues due to their husband's low fertility so they were looking for someone to donate sperm ... as nature intended.
A quick reverse image search revealed that they had "borrowed" a couple images of woman who produces amateur cuckold porn with her husband. The images were of MILF Becca and being honest, if it had been an actual legitimate offer and she had looked even slightly like her, I might have gone for it, with a few terms and conditions in place, namely that I would need something in writing or on video from her husband that I could take to a lawyer and they would say, "This will hold up in court" where he acknowledged that all this was happening with his knowledge, consent and enthusiastic approval, specifically that he was fully aware that I would be fucking his wife to knock her up. Because if they got divorced and it got messy, he could just say, "My wife has been having an affair, the kids aren't mine and I can prove it!" and as the bio-dad, guess who's on the hook for child support?
I'd also ask that the three of us meet at least once so I could gauge if the husband was on board. If I detected even the slightest bit of hesitation or that he wasn't comfortable with it, I'd either respectfully decline the offer and suggest they look into fertility treatments or adoption or I'd still donate my sperm, only we were going to a fertility clinic, I would jerk off into a cup and they would use IVF.
Something else that threw up my bullshit alarms was the fact they claimed that they lived in Vaughan. I'm sorry, but if you can afford a house there, you can afford even basic fertility treatments!
Here's MILF Becca,
Another time, I received a response from a woman who claimed that she was getting married and was to get "fucked hard a couple times before my time is up".
I was sorely tempted to say, "And if you decide the sex is any good, hold onto my contact info, maybe we can see about starting to hook up again after the divorce you're going to be getting in a year or two."
It could have been that she had a really dark sense of humor but she also came right out and said if I had wanted to fuck her without a condom, that would have been fine, there was also a really narrow window that she offered for a hook-up, not giving me time to get tested if I had actually wanted to do that, leading me to believe that she may have told her fiancé, "No sex before the wedding!" and been hoping that I either would have gotten her pregnant or given her and STD or STI that way she could have said, "You caught me, I cheated, let's get divorced!" I got caught up in one couple's break-up in college and I do not want to go through that again!
Maybe I'm being judgmental and gave her fiancé a hall pass as well or he had a cuckolding kink and fucking another guy before the wedding was her gift to him.
I have to admit, if she hadn't mentioned anything about bareback, there's part of me that thinks it might have been fun to have gone through with. I even would have suggested hooking up either the night before the wedding or coming over first thing in the morning the day of. Because all I could think is, "When they tell you 'You may now kiss the bride', just so you know, she had another man's penis in her mouth a few hours before!" And her fiance might have liked that!
Hell, even if we had time to take all the precautions for not using a condom, that might have been fun. I kind of like the thought of her going about her wedding day after getting creampied a couple times either the night before or that morning. I kind of like the thought of that last little bit of my cum leaking out, maybe as she was walking down the aisle, and staining her bridal lingerie serving as a reminder.
The last time was nothing anywhere near as elaborate, I received a response from a woman who said her husband had given her a "hall pass" to find a FWB.
We made plans to meet for coffee, then back to her place for naked fun times if we hit it off I'm assuming, but it never panned out.
Yeah, semi-regular casual sex was the big draw but I think I would be lying if I said there wasn't some small part of me that didn't kind of like that I would have been fucking a married woman and her husband would have been fully aware and cool with it.