"Yes, man, I'm totally serious. She really agreed to it!" My best friend couldn't hide his excitement and practically shouted into the phone. We had gone to high school together, but now he lived a few hours away, so we talked on the phone every so often to keep up with one another's lives.
"There's no way," I replied. "Elena would never do that."
"I'm telling you, we had a big discussion about it." John enthusiastically recounted his tale to me again, the story of how his fiancée agreed to let him have a one-time "hall pass". "We talked about how nervous we were to be getting married, and I made a joke about only sleeping with one person for the rest of my life. She gave me a look, and I was about to apologize and tell her it was just a joke, but then her look changed. She almost looked like she was wondering about something. I was preparing myself for fireworks or the silent treatment all week, but instead she offered a hall pass!"
"Did she explain what she meant?" I asked. "You don't want to get in trouble because of some technicality in the rules of the arrangement."
I was admittedly curious, but I was also jealous. I couldn't believe his luck. Not just because of the hall pass. Most guys would likely jump at the idea of a pass to sleep around, but most guys also weren't dating Elena, my best friend John's fiancée, who had been a crush of mine ever since he introduced me to her a few years ago. How could he even want anyone else? She was a cute, spunky Mexican girl with an alternative-leaning fashion sense. She tended to like alternative rock, grunge, and punk, and this influenced her style. She didn't have a mohawk by any means, but she did have more ear piercings than typical girls and often wore band tees and flannels. I had always been attracted to girls like that, so she instantly caught my eye. John, on the other hand, was much preppier and more traditional. He often dressed in polos and khakis. When they were out together, they were a mismatched odd couple. Then again, the same could be said of John and me when we hung out. I tended to align more closely with Elena, and we both listened a lot of the same bands and often had to pull ourselves away from music conversations so that John could join in.
All in all, and Elena and I had lots in common which led to us having a particularly good relationship. We were never inappropriate or anything, but we definitely often found ourselves chatting when in a big group. I'd be lying if I said there was no flirting, but it was never anything more than playful banter, and John had never seemed to mind our friendship. He was an extreme extrovert and loved talking to anyone and everyone, so he was often glad to have me around to keep Elena company as he was being a social butterfly. It also didn't hurt that, in addition to her style, I always thought she was super cute. She was just over 5' with short, dark hair and light brown skin. She had beautiful eyes and very plump lips that I found to be incredibly sexy. She kept in good shape and had a cute butt, but her large breasts were certainly her most obvious feature. While being big, they suited her small frame, and she accentuated them in her clothes without being overt and explicit. As I had been single and on a bit of a dry streak for a few months, I often had to make sure to not ogle her when hanging out. I'm sure she'd caught me looking a few times, but she never mentioned anything.
John's voice broke me from my imaginings of Elena. "I asked her multiple times if she was serious, and she kept saying yes. She had to really convince me she meant it. She said she understands that getting married is going to be a huge step for us, but she said she wants me to be as comfortable with the decision as possible. Elena told me that she thinks it's normal and natural for me to feel a last-minute curiosity, and she's okay with it. She said I can have one 'meaningless fling' before the wedding, no questions asked. I just can't tell her anything about it, it has to be a one-time thing, and I have to do it before the big day next month. I can't believe it!"
"I can't believe it either," I responded. "I had no idea Elena was so open to this sort of thing." Then I realized there was another pressing issue. "Does she get a pass too?"
"Well," John hesitated, "of course I was super iffy about that once I thought about it. She didn't specifically ask initially, but I wanted to be fair to her, especially if I got to have some fun of my own. And the way I think about it is, when would she do it? She works all the time, hates going to bars, and barely has any energy left after wedding planning. I don't think she really even would have anyone that would work for this sort of thing in the next month. She's not the type to just sleep with some random guy."
"So when are you going to do it? Do you have someone in mind?" I asked. This whole scenario was crazy to me but also very hot. I was dying to know more about it.
"Well, here's where you come in." That stopped me in my tracks.
"Me? What do I have to do with this? Don't tell me you're picking me. I'm flattered, but you're not my type," I joked.
"You wish," John laughed back. "But no. Remember Caitlin? From my old job before I moved? Well, she's actually going to be in town this weekend. She messaged me the other day, and she and I always had a thing before I met Elena. Even after we got together, Caitlin was usually prowling around nearby."
"Are you just going to spend the night out?" I asked. "That seems a little obvious to Elena."
"Again, this is where you come in. You and Elena were talking about a concert this weekend, right?" John continued. "Well, I'll buy your tickets if you take her and keep her company."
