Unexpected Anal Office Tryst Ch. 06

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Unlike the train to Philly, our New York train was off peak hours, so there was plenty of space. Three or four empty rows were between us and anyone else.

"So, do we need to talk about what happened last night?" I asked.

"I'm thinking we probably should."

I paused, not knowing how to start.

"I suppose," she began, "More than anything else, I want you to know I didn't plan for any of that."

I smirked. "I know. Jenny told me it was all her. Or, at least, that your sarcastic mention of it made her want it. But I know you didn't plan it."

"But I also fucking loved it. It was so intense!"

"Yeah," I said. "It went over the top super quick. You calling me daddy was a twist I wasn't expecting, but it really turned me on."

"I don't know what came over me. I just went for it and you both seemed on board."

"My only hesitation was over how Jenny would react. I didn't want to make her curious about our chemistry or anything. But when I saw how turned on she was, I felt better about the whole thing."

Kathryn let out a heavy sigh, and I could tell she was trying to figure out the best way to put whatever she was going to say next.

"Let me guess," I said. "You think we should put an end to this."

She nodded. "I mean, I don't want to. But think about everything we've done and gotten away with at this point. To me, it's a matter of karma. Eventually it will all come crashing down if we keep pursuing it. Let's just live with the incredible memories we've created and quit while we're still ahead."

"One again, Kathryn, we're in synch. I can't even imagine how we could make things any more exciting or risky than we did the last two nights. Anything else would just pale in comparison."

"That's what I'm saying. We had our fun. We have our memories, and we have our secrets. No one can take that from us. But it's time to recommit to our spouses. And Jeremy and I are going to start trying for kids, even if late thirties is a bit late to be having one."

"OK, so...what the hell are we going to talk about for the next half hour?" I joked.

Kathryn laughed out loud, then rested her head on my shoulder. "You're a good man. I'm glad we did this."

And instead of needing something to talk about, we enjoyed thirty minutes of silence.

At the train station, we called separate Ubers. On the ride home, I got an incognito message.

"Just to help myself resist temptation, I'm deleting this app. Just wanted to be transparent about it."

"Me too," I replied, and deleted the app.

And at that, we agreed not to see each other anymore.

Of course, that's what we said after the first time.


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  • COMMENTS
5 Comments
AingealanLannAingealanLannover 2 years ago

Man, I really wish you'd return to this. Feels like the door was left open for it and we never got t9 see the friend get her anal cherry popped. Great story.

BigpickleBigpickleover 2 years ago

Another five star and a surprising twist. I must say when they were strolling to the convention center, it was Katherine who was late for breakfast not Jenny. Oddly , It reminded me of something like that that happened to me. But when I woke up I had a wonderful wet dream in my PJays. Bravo

Lithium_hoboLithium_hoboabout 3 years ago

As unseemly as it might be that they got away with the adultery, having them get caught would have added chapters upon chapters of drama, I'm sure. Plus it might end in a "they found love for each other by cheating on their spouses, and lived happily ever after - thanks to anal" ending, and that would be unsatisfying.

Nevertheless, as disappointing as it may be that they got away with it, it was a hot-as-fuck ride, all the same. An awesome story. I don't usually zero in on anal stories, but this one really made the kink more appealing. And as much as seeing their continued adventures would be neat, I think ending it here is ideal. No idea what you have planned, if anything, in the future for this.

Jenny for life!

RTR10RTR10about 3 years ago

I figured it would end after Kathryn met Jenny. It's harder to cheat when you actually know & like the spouse. And what they said on the train about the risky behavior. Better to end on a high note. Maybe fast forward six months & do an epilogue chapter with Kathryn pregnant & going to Henry for "relief".

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