[jacksonhole]

One of my wife’s oldest friends, Liz, is really cute, and is probably the person I have wanted to see naked for the longest time without success. I have known her since my wife and I started dating when we were 19, and she had been friends with my wife since they were kids. I can’t even count all the times that I tried to engineer a situation to see Liz naked, but it just never worked out. A few close calls where it looked like things might go that way, but something would always happen and needless to say after 30 years I had pretty much given up hope.

Then one night, a couple years ago, Liz was over at our house and she and my wife were drinking pretty heavily because she had recently gotten divorced and was really bummed about how her life had turned out. I left them alone to do their girl talk, but after a few hours they asked if I wanted to hang out with them. Now this is usually a perfect setup for me to try and get a strip game started, the girls are drunk and are looking to do something to change the mood, but given my history of failure, plus the fact that I thought my wife was getting a little annoyed by my attempts over the years, I just blew it off.

We started playing cards, but I didn’t bring up rules or forfeits or anything, we were just playing cards. Just for background, when my wife and I play cards, we have a few “house rules” because we use it as foreplay before fooling around. For example if you are dealt a 4 of any suit, you can get an extra card if you flash, moon, etc. It’s a nice rule because you can use it in almost any game. We have a few other standard rules but I didn’t mention any of this, and honestly wasn’t even trying to make something happen that night.

So I was stunned when about five minutes into the game my wife laid down a 4 from her hand and without saying a word, stood up and flashed her tits for about ten seconds, and I just automatically gave her an extra card. Liz was confused and asked what just happened, so my wife explained. I was still shocked about what my wife had done so I didn’t comment as my wife explained the rules.

It was now Liz’s turn, and she laid down a 4 from her hand and then said, “so now I just flash?” and as she said this she pulled her shirt and bra up to her chin and held it there for around ten seconds although it felt like longer. It was definitely not a quick flash. I openly stared at her boobs. They were very nice, b-cups, with small nipples and very little sag for a late-40’s mother of three.

My wife gave her a high-five and explained that she now got an extra card, which I gave her. The game resumed as if this was the most normal thing in the world, like saying Aces are high card or something like that.

30 years of trying to see Liz’s boobs, and it had just happened right in front of me with absolutely no warning. I don’t know if I was more surprised by my wife or by Liz, but my head was definitely spinning.

The hand ended with my wife losing and without a word, she stood up and took off her t shirt. Apparently we were following all the “house rules” now.

Over the next hour we played a variety of games, always following the house rules which my wife explained to Liz as we went along, and with my wife leading the way we all got naked.

Normally once we are naked, my wife and I start adding sexual dares to the rules because for us the games are a part of foreplay, and I was curious to see if she was going to lead us in that direction. I had decided not to try and guide the evening at all because my wife was doing such a good job, and I could only fuck things up.

But then, rather suddenly, we lost our leader. Liz had gone to the bathroom, and I was fiddling with my phone trying to find a new playlist of music, and when we got back we discovered my wife curled up on the floor sound asleep - passed out would a better description.

Liz and I were both naked, as was my wife, and for a minute we didn’t know what to do. I got a blanket and covered my wife so she wouldn’t get cold and then looked at Liz to see what she was thinking. I was certain that she would decide that it was time to call it a night, and I wasn’t going to disagree if that’s where she was at - it was after 2am.

But once again, the unexpected happened. Liz asked if I wanted to go into the basement and play pool so we didn’t wake up my wife. Umm yes!

So we went down to the basement and played a couple games of pool, which was awesome because of all the bending over to take shots and the fact that I could really stare at her tits, ass and pussy when she was focused on taking a shot. I’m not sure how long we played pool, maybe an hour, but we were naked the entire time. We went upstairs to check on my wife between games, but she never even stirred.

Some time after 3am we both decided that it was time to call it a night. We went upstairs and gathered up all the discarded clothes and I managed to wake my wife up just enough to get her up to our room and tucked into bed.

When I came back down to the main floor, I expected to see Liz in her pajamas crashed on the couch, but instead she was cleaning up the kitchen still naked. 30 years of hoping to catch a nipple slip, and then one night, it appears that Liz may be a nudist. We briefly hugged, which was the only physical contact we had of any kind that night, and then I went up to bed.

The next morning my wife said she didn’t remember anything after we started playing cards. I mentioned that she had taught Liz our house rules, and she said that jogged her memory a little, and she hoped Liz hadn’t been uncomfortable. I shrugged and said it didn’t look that way to me. She and Liz went out for breakfast and when she came home she took a long nap. The naked evening never came up again, although Liz sometimes makes side comments if the topic of cards comes up.

I have seen Liz naked or topless on one or two other occasions since then, but those are other stories and this one is already long enough.

Two lessons that I take from this:

1. If your wife is your wingman, anything can happen
2. I am terrible at predicting what events will lead to nudity