After The Train
Part 2, Chapter 3: After the Train - The Weekend in Chicago - A Question of Choice & Sharing
After hours of shared enemas and playing enema games with each other (like who could hold their enema the longest or could hold it while engaged in some very sexual play) and then spending more time in her bed just exploring each other through each and every sexual position and penetration, it seemed that we were both contented to be intertwined in her bed that had become our own personal "wet spot." As I slipped out of her one more time, my mind drifted through how sexually intimate and erotic this had all been and how I had so missed this type of connection with a woman. It had been too long since I felt connected and close in this way.
With her beside me, us in each others arms, I was prepared to drift off to sleep in the afterglow of so much sexual release and satisfaction. I was already allowing myself to consider what might be next for us and how that might work for the two of us. At some point in my life, I would come to a fork in the road or a crossroads of sorts to choose between the marriage that had all the appearances of ending (but might not) or moving on to something else with someone else. I had been in a holding pattern for quite some time. It seemed too complicated to be definite about a future for us, but I allowed my brain permission to consider it. I knew some version of the question about us (Catie and I) would come up sometime before I would leave to go home.
"Can I ask you a question?" she asked.
I remember thinking that she's reading my mind. The question she was thinking about just wasn't the question I was thinking about. "Sure," I said.
"If you had your choice, who would you choose?"
In an instant, the thought flashed through my mind faster than she could ask the question, choosing between her and my soon to be ex-wife.
"Jody or me?"
"What?!!?"
"If you had to choose between Jody and I, which one of us would you choose?"
At this early hour of the morning, after fucking our brains out and multiple orgasms for both of us, this was the last question I would have expected. I had encountered this type of question before and metaphorically it was an emotional landmine to step on and explode. It was more fraught with danger than the question "what are you thinking?"
"On what basis? It would be like me asking you who you would choose, me or Mark (Jody's current romantic interest)? He's much more handsome than I am." I probably came off as a bit indignant over being asked this question. It certainly was destroying my mellow mood. And this could go very badly and I was expecting this to go down the path of Jody's appearance compared to Catie's.
"I didn't mean the question that way. It's something you suggested."
In that moment, I was totally clueless.
"What did I suggest?"
"Jody dropping her shorts and you fucking her...in the ass! Would you have done that?"
I thought for a moment, though I've already recounted what happened.
"I was standing there naked in front of both of you...with a fairly sizeable hard-on...talking about anal sex. I wasn't embarrassed or intimidated by it, but I was looking for a way out of her questioning. You gave me the opening by telling her how she would have felt to have me inside her ass like I was in yours."
I continued,
"I didn't expect that she would accept the offer and you seemed to make it clear that I'm yours, though the 'maybe later' threw me."
"But if she had, what would you have done?"
"I would have assumed that I was exclusively yours."
Which was a true statement of my feelings in the moment. I was laying there, confused about where this was going. Afterwards, it made sense because I was assuming something that was incorrect about both the nature of the question and the exclusivity of the relationships.
"If I told you that it was okay?"
"I think I'd ask if you were sure about it."
"And if I told you that I really wanted to watch you two together?"
"I'd never expect that of you. That's the stuff of male fantasies."
"Women, too!"
She went on to describe some of her fantasies. I listened, interjecting here and there, as she described multiple scenarios. It got both of us horny and hot again and we had another orgasm session before I pulled the sheet over us and then falling asleep in each others arms.
We had a mid-morning start planned and it was already pretty late into the early morning.
A very great story above your trip and …