This is based upon a question my wife asked me back in the summer of 2007:
My wife nervously asked me if it'd be okay to ride with her boyfriend from work on the back of his motorcycle and spend the weekend at his cabin up north.
I asked for time to think on my answer, she said okay.
~~~~~~~~~~~
The next day I said yes but with some conditions. I told her I wanted her to keep me informed of their activities with selfie photos. And that anytime they had sex, to send me a selfie of your vagina afterwards (before cleaning up). It's the least she can do if I cannot be around to watch her.
Then I also told her, "And ... I want you to present your ass to him to fuck at least once. You have the nicest ass on this planet, and it'd be a shame that he could not enjoy it." I pressed a small tube of anal desensitizing lube into her hands.
I continued, "And this is important...take a selfie of your backdoor afterwards before you clean up. I want to see that he filled your ass."
Her eyes opened in alarm at that last part.
Still holding her hands, I told her, "Look. He will have a VIP Access pass to your body for the weekend. I want to know what happens and enjoy it from afar."
I continued, "bend over forwards and backwards for him this weekend, but when you're back, I will reclaim you as mine. Agreed?"
She started, "but anal is only for you..."
I put a finger over her lips to quiet her, "this is what I want in return for letting my wife go with her coworker boyfriend on an unsupervised weekend of sun and fun in the boonies. Can you do this?"
She thought a minute while looking down at the lube in her hands. "Okay."
"And whenever you're on his bike, you wear a helmet. But no 'helmet' for him when he's mounting you." She smiled at my lame joke.
She grabbed her phone and went off to the other room to call him with the news. A few minutes later she returned, "we'll leave early from work on Friday, so I'll take a small backpack with me to work in the morning with everything I need for the weekend."
~~~~~~~~~~~
On Thursday night, she laid out everything she planned to take on the bed. Since the place is remote, she said a lot of clothes weren't really needed. Plus, she needed to pack light for the bike.
She decided to go with a southern redneck girl theme. She pulled out a couple of her skimpy crop tops, one vest to cover more if needed and some jean short shorts and a couple of bikini bottoms plus her cowgirl hat. Then she packed her cowgirl boots for the ride and boho sandals for the time up there. She added basic personal effects and threw them into a backpack.
"Don't forget the lube I gave you; you'll regret it later."
She smirked and said, "oh yeah".
I suspected she had forgot on purpose, "do you plan to ignore my deal and not give your ass to him?"
"Honeybun, this is a big deal for me. I don't like giving my ass up for just anybody."
"And I can still cancel this weekend, dear. Do you want me to do that?" I asked.
She looked up quickly, "please no, I already promised him this weekend at his cabin."
"And you promised me you'll give him your ass this weekend." I countered then added, "AND to send me proof of his cum leaking from your bum."
She sighed, "yes. But I worry he won't be gentle as you."
She was trying to stroke my ego.
"He hasn't hurt you in any other way, right?"
"No"
"Then you need to present him your naked lubed-up ass. You just need to guide him to be gentle, don't you?"
She sighed again. "I guess."
I took her hands in mine, "I want you to have fun, darling. And I know you will. But make good on my requests and there might be more times like this in the future."
I continued, "Will this be the first time you've ridden his Harley?"
"I took a short ride on his bike in the Spring, remember? But not this far."
I also remembered she had told me when she had been on Harley's years prior, the vibrations from the seat alone could cause her to orgasm.
I wrapped my arms around her, kissed her and whispered into her ear, "and wearing those short shorts on a Harley all those long miles won't be giving you reoccurring waves of pleasure?"
I could feel her grin on my neck, "maybe..."
I laughed, "you'll be worn out before you even get there!"
"I'm sure I'll find a way to get through it," she smirked.
~~~~~~~~~~~
The next morning was a rush to get ready and with a quick kiss, she was gone to work with her morning Coke in hand. I could tell she was energized for the day.
I tried not to be nervous about letting my wife go for the weekend. I tried to focus on my work, but I had butterflies in my stomach most of the afternoon.
Early afternoon I got a message from her.
"Heading over to his place to change and prepare to go!"
A minute later my phone dinged again and it showed her in her business casual work clothes sitting in her car and sticking her tongue out at me.
I smiled.
~~~~~~~~~~~
About 30 minutes later, another ding.
"How do I look?" followed by a picture of her wearing a short crop top, her jean short shorts, cowgirl boots and her light brown cowgirl hat. And a smile.
"Damn! You look hot babe!" I replied, "don't forget our deal... lots of selfies and give up that a**!!"
"I can't forget... one thing, he said the cell phone coverage is really bad out at his place. What do I do?"
"Damn that sucks! I'll tell you what, keep taking selfies and send them when you are in range again."
"Okay."
"Okay be safe. I'll worry about you until you're back home. Love you!"
"Love you too Hun. And thanks for agreeing to this."
"Yep. I hope I won't regret this later."
"You won't, I'll be extra good for him like you said, but when I'm back, I'm yours!"
I closed the conversation with a lip emoji.
~~~~~~~~~~~
Another 30 minutes later and my phone dinged. It was a photo of her sitting on his Harley wearing the same outfit, one hand around his waist, the other stretched out with the phone. They looked to be sitting at a red light or something. She had on the helmet -- good girl -- with the visor up, her eyes smiling at me.
~~~~~~~~~~~
After an hour, another pic of them at the entrance of a dirt road off the main road. He was unlocking the gate while she waited near the bike.
A message followed, "we're going into his property now. Still have signal."
I answered with, "did you cream your shorts during the ride?" and added a smile emoji.
It dinged. "Yes, I'm unable to resist tight shorts combined with STRONG low freq vibes."
And dinged again, "I didn't wear panties today either so these shorts smell... interesting." and she added a laugh emoji.
I replied, "oh my. Still horny?"
Ding. "We both are. I expect I'll be sending one of your photos soon to prove that after we arrive!"
"Awesome. Look forward to it."
I couldn't focus on work anymore, thinking about what they were probably doing. I packed up and headed home.
~~~~~~~~~~~
I got home with no message. I tried to forget about it and busied myself with some chores around the house. When I finished, I grabbed a beer and sat down. I kept checking my phone but nothing. I began to wonder if their reception was shaky.
After almost two hours, there was a ding. Then another. Then another.
I scrambled for my phone.