For me it was 3 different women (civies) in 24 hours. Two were 18 and one was 31. I was 39 at the time. The first 18 year old spent Friday night with me and left Saturday morning at 11:00 AM. The second 18 year old called me an hour later from the bus she was on. Said she was a couple blocks from my place and asked if she could come over. She really wanted to suck my cock so I hopped in the shower. She was a master at giving BJs. Made me cum a couple times and left a couple hours later. At 5:00 PM, the 31 year old called and asked if I had any plans. I'm thinking, to myself (and laughing) is this really happening. Well, she came over and by 8:00 PM, I was giving it to her hard. That only ever happened once. A very memorable day indeed.
Another time I went for dinner with an ex-gf's and her husband. We all get along well. After a bunch of after dinner drinks, my ex crashed on the living room couch. Her husband and I stayed up and drank for a couple more hours. When it was time to leave, he said I could crash in their spare bedroom. So off to bed we went. I got up early and made my way downstairs, expecting to leave right away. My ex was still laying on the couch but awake. She motioned me to come over and said, lay down with me for a minute. She moved forward, I laid down behind her and wrapped my arm around her.
It was summer, I was wearing shorts and she was wearing tights. After a minute she takes my hand and moves it down and presses it against her pussy. I'm like okay, this is risky. I take her lead and start rubbing her pussy. Then I slide my had down the front of her tights and slip a finger inside her. She was so wet. My cock was so hard and I'm pressing it against her ass. Sensing the inevitable, she reached back, undid my shorts, pulled her tights down and I immediately slide inside her. There I am, fucking her hard on the couch in her living room with her husband sleeping upstairs. All I'm thinking, besides how fucking hot this is and how good it feels, is what would happen if her husband came downstairs. After what was probably only 2 minutes of jamming it deep inside her, I blow my load, leaving her with a lovely creampie. She gets up from the couch, puts her hand between her legs so she doesn't leave a trail of cum on the floor as she walks to the bathroom. I'll never forget that experience. I left before he woke up. We had sex probably 6 times after we broke up. Still friends to this day. She is one horny woman but she tells me her husband doesn't have much of a sex drive. That's probably the most taboo thing I've done.