Two married ladies. With both it was a long build up of hanging out and making out finally culminating in a one-time-only fuck.
First was a coworker at a newspaper that I moonlighted at. I'll call her Pauline. She was about ten years older than me but married to a guy about my age. At the time I was just split up from the second wife and dragging my ass around. Pauline was actually happily married and I rather liked her husband. But, we felt a connection pretty fast (may have started off as pity for me but it grew) and explored it for months.
She was fairly petite and quite cute- a short-haired fire blonde with no butt at all but great natural tits. They were serious handfuls with very small nipples stiff as the proverbial pencil erasers. I was thinner then and had gotten a bit of a build throwing newspaper bundles around for several months.
We worked afternoons into evenings and would finish around the same time- 8 or 9 at night. She'd come over to my little apartment. Pauline really liked to drink, and I was pretty much a lush back then, too. We'd hang out and drink and talk and make out for a while (but never getting to fucking) until she needed to get home to her hubby. Of course after she left I'd give Old Blue a serious beating and her hubby would benefit from her worked up state after she arrived back home. A few times we'd go to a bar near our work but after a few drinks Pauline would say some random stuff like, "You know I really don't like giving blowjobs" quite loudly- it was embarrassing, so I stopped taking her there.
A couple of times I got her over to my dad's house while he was out of town and use his secluded hot tub in the back yard. That was nice to just slide around on each other in the hot water and fondle her while we drank.
One time at my place while making out on the couch Pauline laid down with her head in my lap and did give me a blowjob with her tiny little mouth that could still amazingly take quite a lot of my cock, while I worked my hand into her shorts and pushed my fingers along her ass crack until I could fondle her wet pussy. She didn't cum then and in fact I was a little too drunk to reach a peak either, but we both enjoyed the feeling we were giving each other.
We only fucked once- at my dad's house after a hot tub session. We were naked on the couch and really getting into it- I finally slid her on the floor and laid over her and worked my cock inside. Pauline's pussy was snug and warm. I thrust in her for a few minutes with her hard nipples on top of those wonderful tits rubbing my chest until she came, when she suddenly pushed me off her and started going into the 'we can't be doing this' thing. OK, I wasn't going to force the issue but dang my balls were blue by then. She agreed to suck me and this time I did cum. Turns out she really didn't have a problem with blowjobs
As I met and began dating my next wife things tapered off for us. She did get mad about that but after I said, "Yeah, but Pauline- I can't HAVE you!" she understood and backed off. I also think her husband figured out something was up but didn't push the issue- perhaps deep down he didn't want to know the truth. It was time to move on.
The second married lady was actually an old girlfriend from high school that I reconnected with years later. This was far and away a much more enjoyable experience than with Pauline. We hung out in the same circle of friends- me and my wife and her and her husband. I'll call her Gwen. At that time I was married to the new wife from the "Pauline Era". Gwen was in the middle of a serious rough patch with her husband and feeling rather down.
We were both in early middle age- Gwen wasn't ravishing but was attractive. She was fairly tall and had great soft 'hanger' boobs. Pretty curvy- she had been fighting weight issues all her life. But that just meant some great handfuls of ass and tits to work with.
In high school I had treated her pretty badly, but I always liked her. I felt pretty guilty about it as time went on and was hoping to find a way to make it up to her. We ended up doing theatre together and after a while I'd get her to hang out after rehearsal and we'd talk, either in the theatre parking lot or out in the sticks. I really wanted to do something to make up for being a dick those years ago, so after I specifically apologized for my rotten behavior way back then, I was the good friend and listener while she poured out her hurts. There was a lot of hugging and arm wrapping around shoulders and that kind of touching, while the tension built and built.
Finally, one evening she was right in the middle of a sentence when I pulled her to me and laid a big kiss on her mouth. Gwen remains one of the best kissers ever- nice full lips, very enthusiastic, and she knew what to do with her tongue.
This making out continued for a few weeks (I move very slow in these matters) while her husband moved out. As a summer holiday weekend approached my wife wanted to go visit her family, but I couldn't go because I was scheduled to work then. Finally an opportunity to take things further with Gwen!
After work on Saturday that weekend I had a few people over to celebrate the holiday and drink, including Gwen. Eventually everyone left, except Gwen. We were actually pretty drunk but we still fell into bed and got naked. I enjoyed the feel of her curves and her great nipples in my mouth and well as eating her pussy. She used those fantastic lips on my cock and it felt so good. I climbed on her and pounded her for the first time.
That's when I learned something new about Gwen. In recent conversation she had hinted at a checkered past, and I found out what it was- in the early 1980s she was a hooker in West Hollywood, for about six or eight months. She obviously survived that just fine but she picked up a good trick with squeezing her Kegel muscles while her johns (and everyone since) were inside her. Wow- that was an amazing feeling. We had a great time and she came once or twice and of course I was too drunk to get off. We slept together all night and then parted ways the next morning.
I went to work that day and after getting home and showering went over to Gwen's house. We sat and talked on her porch for a bit but we both knew we had unfinished business. We started kissing and rapidly moved to groping and fondling just like when we were teenagers. It was only a few minutes of that before we went into her house and to her bedroom. We helped each other get undressed and into bed.
I got her to get on top of me for a bit during which I was playing with her large floppy tits. It was easy for me to squeeze them together and rub her nipples against each other, and then put both in my mouth at the same time for some good sucking and licking. She wasn't as sensitive with her nipples as some ladies I've known but she enjoyed the attention anyway. I went down on her and she came. She also sucked my cock some more which felt very nice.
Finally it was time to get serious. I climbed on her once again and ran my cock into that fine, fine pussy. I was tired from work and a bit tipsy from drinks we had together, but it just served to slow me down. I pumped at her for the longest time while she gripped and squeezed my cock with her Kegels- making me work to get past that ring. It was the slowest build up to orgasm I had ever experienced (and never duplicated with anyone else).
I don't think she came any more- she seemed focused on me. Every push felt even better and near the end I was moaning with every thrust. I hit that plateau of tingling in the base of my cock, slowly spreading to the head, but it was still a slow five minutes of this before I finally crested that wave and with some pretty loud grunts and moans started squirting my cum into her fantastic wet pussy. It was the longest orgasm I had ever known and seemed to go on and on, but of course we know it wasn't more than about 15 seconds or so.
I collapsed on her with my elbows on the bed holding most of me up while we both floated down from that cloud, kissing and snuggling. I eventually rolled off and she hopped up to get a hot washcloth. She tenderly cleaned my cock and washed her pussy and climbed back in bed with me. I stayed most of the night but had to get going early to get back to my home and be ready for my wife to return from her visit.
We had a few more months of hanging out together but it appeared we both got "the horns" for each other out of our systems and we never repeated that weekend or even made out much after that. Soon her self confidence returned and she got another boyfriend, and I never strayed from my wife again (who was pretty damn good in the sack herself).