It was probably 12 years ago, but this remains one of the hottest experiences I had.
It was with my ex girl friend. We were in a distance relationship – she was in Vietnam and I was going to college in Singapore. She was visiting me for a couple days.
We didn’t have much money back then, so we rented a room (airbnb style before airbnb was a thing) in a 3-bed condo apartment. The host of the condo was this 30-something woman, apparently she was a stay at home wife. We didn’t talk much but I remember she was hot, in a MILF way.
So we got into our room, and of course having seen each other like a couple months before, we spent the whole day on the bed. My ex was a squirter, and I have been able to get her to squirt using 2 fingers. That day for the first time I put 2 fingers in while my cock was thrusting. My length is decent, but I’m not very thick so that definitely helped filling her. She went wild and after a couple minutes, she squirted twice in a row. Until this day I couldn’t forget the feeling when her legs trembled, and her vagina compressed and pushed my cock out. Her vagina was really shallow then when I pull my cock out I could see her pink flesh inside.