Hotwife Diaries Ch. 01

Apart from these short conversations about porn, our relationship was as normal and thriving as ever. We continued to have sex almost every day, and I hardly ever thought of her with other men. Meanwhile, we were having conversations about our careers and the idea of having children. I had recently gotten a promotion at work, and I used my increase in salary to save for a nice vacation south of the border in Cancun, Mexico. We booked our plane tickets and purchased a room at an all-inclusive, adults-only resort on the Mayan Riviera in the spring. As our tropical getaway approached, Samantha and I grew more and more excited to enjoy our trip together. I even took her shopping for new swimsuits, and I bought her some scandalous-looking items that I was sure would turn some heads at the beach. Things were going exactly as planned, until one night, less than two weeks before our expected travel date, I got an email from work.

"You're kidding me," I groaned, reading my email from my phone one evening while we hung out on the couch. "Our biggest client will be visiting from out of the country and is insisting on meeting with me. Right in the middle of our trip!"

"What?!" Samantha exclaimed. "Tell them no!"

"I want to," I said, "but I'm not sure I can. They're honestly our biggest account, and my work with them was a major reason for getting my promotion. They want me to personally tour them around our facilities, so I can't just video in."

We rushed to the computer to try to revise our travel itinerary. We learned that our plane tickets were non-refundable but were transferable - we could change them to another date, or even to another name. But the resort, which we had gotten a pretty good price on, was already holding a large deposit over our heads that we couldn't get back.

I sighed. "You should go without me. You can take a friend."

"What? No!" Samantha said. "No way. I only want to go with you."

"Well, you're not going with me," I lamented. "At least not this spring."

Samantha hugged her knees to her chest and pouted. It was disappointing to say the least. I imagined all the fun we could have had together, drinking cocktails on the beach, snorkeling in romantic coves, having sex in new and exotic places. That's when an idea hit me.

"Samantha, I have a suggestion. I want you to go on this trip if you're able to find a friend to go with you." Samantha was about to protest, but I cut her off. "Now hear me out. I'd like you to go on the trip, and I'd like you to go as if you were single."

"I beg your pardon?" she asked. She looked dumbfounded and distressed.

"Think about it," I said. "Those crazy fantasies I have, thinking of you having fun with other men, dating around, enjoying their attention -."

She caught on. "You want me to actually live out your fantasies? And flirt with other men?"

"Yeah," I replied. "Flirt with them, and maybe even more. If I give you permission, it isn't cheating. We'd come up with some parameters, some boundaries we'd agree on. And in return, I'd like you to tell me everything that happens on your trip. In detail."

"I don't know," Samantha said. "The fantasies were one thing, but I can't see myself doing this in real life. What if it backfires? What if one of us ends up really hurt?"

"I won't be hurt," I assured her. "As long as you follow the rules." She gave me a skeptical look but said nothing. "I think it could be fun," I went on. "I know it will be fun for me - I'll hear all about it. And about how sexy my wife is to all kinds of strange men. Your pleasure will be my pleasure," I insisted. I tried to sound playful, as I got up and moved toward Samantha, wrapping her shoulders in an embrace. She leaned in toward me.

"Give me some time to process this," she said. "I'll think about it."

"That's all I ask." I kissed her on the cheek. And despite the sting of not joining her on our trip, deep inside I was more excited than ever.

***

The next morning was a Saturday, and I'd slept in more than usual. It was nearly 10am when I rolled out of bed, and when I got to the kitchen, Samantha was making pancakes.

"Good morning," she greeted me, eyes still down in the pan. "I talked to Jenny. She said she can go."

My mind erupted in shock and excitement. Not only had Samantha agreed, but it had only taken one night to convince her, and she had already asked a friend! Could she be as excited about this idea as me?

"Great," I stammered. "What did you tell her?"

Again, not looking up, she said, "Oh, I told her about your meeting, how important your work function was, but also about how amazing the resort photos looked online. I sent her the link, and she's totally stoked."

"I see," I said. In some ways, Jenny was an ideal companion for this trip. Her family was from Puerto Rico, and not only did she speak Spanish, but she was a total flirt, which would help Samantha get in the groove.

"By the way," Samantha added, quickly glancing up at me and then away. "I hope you don't mind, but I told her she'd only have to pay for half of the room, and we'd cover the plane ticket. Since the trip's short notice. Is that okay?"

"Yeah, perfect," I said. I hadn't even thought about whether we'd ask her to pay. Our finances had looked good lately, and I wasn't even worried. "Did you tell her about - about the stuff from last night?" I couldn't quite say it aloud.

"About that," Samantha began. She looked at me fully now and her eyes looked serious, almost concerned. "Are you sure that's what you want?"

I took a breath. My balls were screaming, YES, but in my mind, I had a whisper of doubt about how things might unfold. I decided to side with the screaming. With measured restraint, I answered, "I still feel good about that, yes. As long as you do."

"I admit it sounds fun. Scary, risky even, but fun. And we'd have to figure out our rules before I agree."

So that morning, as we ate our pancakes, we devised the following rules:

1. Only do something if it feels entirely safe.
2. Only do things you want to do. Don't do anything just to please James.
3. Always let Jenny know where you are and who you're with. Always.
4. Do not form attachments. Do not have an encounter with someone on multiple days.
5. If you decide to have intercourse with another man, he must wear a condom.
6. You will send a daily email update to James. Apart from a general update on the trip, it will include a detailed account of any flirtatious or sexual encounters that may occur. Leave no details out. There should be no secrets.
7. Write what you truly feel: the sensations, good and bad; the emotions, positive or otherwise. Write the truth, not just want you think James wants to hear!

And that was it. We read the list through a few times and agreed that it was a sound plan. Although she would email me daily, we agreed that she'd get no response from me, as I didn't want my input to influence her behavior. The exceptions, of course, would be in case of an emergency or if I got cold feet about our plan. In addition, I assured Samantha that if nothing ended up happening or if she realized she didn't feel comfortable, she could abandon the idea and simply enjoy a fun, relaxing vacation with her friend.

When their departure date finally arrived, I drove Samantha and Jenny to the airport and pulled over in the drop-off zone. We exited the vehicle, and I pulled their luggage out of my trunk. With tears in her eyes, Samantha kissed me goodbye and handed me her wedding band to hold on to - she wasn't going to wear it on the trip, and it was safer leaving it with me. The symbolism wasn't lost on us, as we held each other tightly for a final embrace.

"I love you," she whispered in my ear.

"I know." The Star Wars reference was our little joke, and I think the familiarity gave her comfort as she gave me a final squeeze.

"I'm not sure if I can do this," she said.

"It's okay." Holding her by the shoulders, I looked in her eyes. In my best Yoda impression, I began, "Do or do not," then shifted to my own voice to say, "I will love you just the same."

A moment later, as I watched her and Jenny roll their luggage into the airport and out of sight, I found myself filled with hope but devoid of expectation.