[jacksonhole]

Last night one of my wife’s friends named Sam came by to hang out and have a few drinks. I left them alone for a couple hours and then asked if they wanted to play a game or something. I suggested a dice game, but my wife’s friend said she was too buzzed to learn a new game so we played that game where you hold your phone up to your forehead and the other people give you clues to the word shown on the phone.

It was fun for a while but got kind of repetitive and at some point I suggested we do something else. They asked what I had in mind and I jokingly said we should play truth or dare. Sam just laughed and said there was no way she was doing that, and we went back to playing the other game.

About ten minutes later, Sam said, “if we did play truth or dare, how does it work?” We started to explain the rules, and she shook her head and said there was no way she could do it. She went to the kitchen to refill her drink and I started looking on my phone for something else to play because I was getting sick of the other game.

When she returned, she sat down and said, “ok, somebody ask me a truth question.” We weren’t sure if she was serious, so my wife and I just sat there for a minute and she insisted she was ready to play and told us to make it a good question. So I asked her when was the last time she had an orgasm, and she immediately replied, “this morning.” Then she asked what happens now, and we said it’s her turn to ask one of us. The next few rounds were all truth questions, but they got increasingly personal and all had some element of sex. Questions about favorite position, favorite toys, masturbation frequency, that sort of thing.

The next time my turn came up I chose dare, and my wife dared me to moon them. I stood up, turned around and pulled down my pants and boxers, and the the girls cheered and applauded in appreciation. As anyone who enjoys playing stripping games knows, this is a pivotal moment in the game, the first showing of skin and the reaction to it by the other players. If anyone is going to get cold feet, this is when it happens.

I pulled up my pants and then asked Sam, “truth or dare?” She started me straight in the eye with a little smile on her face and said “dare.” I said that she had seen my ass, so I wanted to see her boobs. She made a joke about nobody wanting to see her saggy boobs, and I thought that she might be about to back out, but then she lifted her shirt to her chin and pulled up her bra revealing her breasts to us.

I told her that her boobs weren’t saggy at all, and that I thought they looked fantastic. She asked if I was being honest about that and I said absolutely. I asked my wife for her opinion and she agreed that Sam’s breasts were great. The best part was that she kept her boobs on display during this whole discussion, and she actually lifted one of them and squeezed it a bit as she looked down at her breasts.

Now the game was on for real, and while people still choose truth sometimes, we all started doing dares. Both girls showed their tits a couple times, and everyone showed their ass, and did funny dances, and then the next time I chose dare, my wife took things to the next level. She dared me to kiss Sam, and made it clear that she wanted to see a real kiss. If showing skin is the first milestone in a stripping or dare game, actual contact with a player who isn’t your spouse is a bigger one, and I was a little surprised my wife had suggested it.

Sam and I stood directly in front of my wife and then leaned in and just started totally making out. Sam uses her tongue a lot more than my wife does, but she was a decent kisser and we sucked face for at least a couple minutes before declaring the dare complete.

My wife picked truth next and I asked her if watching me kiss Sam had turned her on and she said it had. Then Sam chose truth and my wife asked her if kissing me had turned her on and she said that it definitely had. Things were definitely progressing nicely, but I still had no idea how far this would go.

On my next turn I chose dare and Sam said, “you should just take your pants off,” and when I stood up to do so she added, “and your underwear too.” I paused for a second and looked at my wife and then Sam who were both smiling, I was expecting them to say for two minutes, or for the next round, but they didn’t. Permanent nudity is another huge milestone in a game like this, and once someone takes that step I’ve found that nobody backs down on any dares that follow.

I took my pants and boxers off and stood in front of them for a few seconds. I was about half-hard when I first stripped down, but my dick was growing right in front of them and they both seemed to appreciate it and were openly staring at my penis. My wife reached over and cupped my balls, then leaned in and took my dick into her mouth. It wasn’t a full on blow job, but she took it all the way in and licked around for a few seconds. Sam was intently watching this and when my wife pulled back she said, “Nice!”

I sat back down and remained bottomless for the rest of the evening. Over the next couple rounds I managed to get both the girls topless which led to them comparing boobs and discussing nipple size for a while. The nudity also improved our options for dares which quickly led to both girls getting their boobs sucked on simultaneously by the other two players, and that turned up the heat considerably. Both of them also seemed comfortable groping me whenever they wanted so that was happening too.

So I am naked from the waist down, and they are both naked from the waist up, and we are all hanging out drinking and laughing as if it’s totally normal. Amazingly, we continued playing and on my wife’s next turn she chose truth. “Have you guys ever had a threesome?” Sam asked my wife. My wife said yes and then Sam chose truth and my wife asked her the same question. Sam quietly replied, “No, not yet.”

The game broke down, or at least they decided I wasn’t needed any more, and my wife and Sam just kept going back and forth, each time asking “truth or dare?” Replying “truth” and then asking some very specific questions.

Did you enjoy it? Yes.
Have you ever thought about having a threesome? Yes.
Is that where we are headed tonight? I don’t know, maybe.
Would you be ok with that? Yes.
Would you be ok with that? Yes.
Are we really talking about this? Yes.
Should we go upstairs? Yes.

So we went upstairs. I will finish the story of what happened upstairs in a separate post.