12/02/2025
One of my fantasies is to have sex with a family friend of my wife and mine. She's Japanese and has an older husband. She's really sweet and I've fantasized about her off and on for a long time. Sometimes I'll jack off to the thought of her. My wife and her are close, so it would definitely be awkward. But it's just one of those things that simmers in the background.
What do I imagine? Well, I wonder what it might be like to have a night together. Maybe per agreement that this could happen on the condition that it was a one-time thing only – and so we would have to fit it all into a single night. I don't think her and the husband are intimate anymore – so it might be something she's thought about as well. I imagine it being awkward in the beginning. Maybe she eventually takes off her top and dress so that she's in bra and panties. I would take off my shirt and be in briefs only. My erection would be very visible through the briefs. She would lay down and I would lay on top of her. There would be cuddling and foreplay and then I would remove my shorts. My erection would be full and would excite her because she's not used to such a hard erection – and maybe hasn't experienced one in many years. And then I would remove her bra and panties. I would sit on her chest and she would stroke my cock. Eventually I would enter her, moving slowly at first but then faster. She would be very wet and would have multiple orgasms, and I would eventually pull out and cum on her breasts. We would spend the rest of the night cumming together repeatedly.
When it was over we'd go back to our regular lives. But the memories would always be there - and whenever we got together each of us would look at the other with that knowing look – knowing what the other looks like naked, what they feel like in the most intimate way. And it would be exciting each time.