Broken – The Perfect Night

My family was out of town for the weekend and Hailey and I decided to get together this was the weekend she referred to in the now infamous email. This time I really wanted to show her a good time. We had that sort of regular hangout night that first overnight.


Broken is a story that is best read Chronologically to start from the beginning – Prologue

My family was out of town for the weekend and Hailey and I decided to get together this was the weekend she referred to in the now infamous email. This time I really wanted to show her a good time. We had that sort of regular hangout night that first overnight. This was a chance to celebrate her being out of her marriage and our love.

While there was still that looming issue of her accepting other “invitations” at this point I in our journey I felt like I recaptured Hailey’s heart. I could tell her focus and hope was on me again. And I wanted to show her it was worthwhile to her.

I made reservations and booked a room at a Casino nearby. It was actually nice to drive in the car with her to a place that we would spend time with. Not ducking James. Although we still were but more on that in future posts… We were just cruising there listening to music and talking. It felt real. We arrived at the Casino and promptly checked in. I asked what would you like to do?… Fuck, Gamble, or Drink first. I think we all know which one was coming.

I laid her at the edge of the bed and leaned on top of her. We kissed and I undressed her, then myself. It wasn’t a crazy experience but a good one. I grabbed her legs and hoisted her close to the edge so I could penetrate her while standing with her laying down. This is one of my favorite things ever because the visual is amazing. I would just try slightly different angles and speeds. And yes ladies when you are getting fucked like this watching your tits jiggle is heaven. As always we had plenty of eye contact. We were excited but kind of living in more than just sex- it was a moment. We were almost a couple. When it was time I pulled out and came on her. I was so excited I covered her neck to navel. I also didn’t want her to have to carry me around all night. I went to the bathroom and grabbed a hand towel and wet it (warm water gentleman). Came back and cleaned her up.

We got up and got ready. She wore a stunning black dress and I got dressed up for her as well. We both clean up really nice. We had reservations at one of the places in the casino. We sat down ordered drinks and Hailey of course made chit chat with the waitress in the charming way she can. We both got something the other one wanted to try so we could taste a few different things. We were a team. We had funny dialogue with each other and the waitress. I told her how beautiful she was and she said how handsome I looked.

When dinner was done we walked into the Casino. She had only played once before so I taught her how to play a little video poker and what slots to pick and how they payout. We held hands as we walked. I would let her sit at the machine and stand by her. At one point in the night. I looked at her brought her chin up and she smiled and we may have shared the sexiest kiss in the world just then. I am sure onlookers were like… what the fuck. It was that good. But it was also sweet.

I then gave her some money to play with and she was on the proud side and didn’t want it. I told her she can give me some on the next one. I told her this night was for her. I didn’t mention it but where she was a single mom just moving into a new place I knew money would be tight. I wanted to treat her but tried to do so without damaging her dignity. And I never cared about money in that way anyways.

She was playing and starting to win and I was cheering her on. Then on one spin. It came up big… $500. She looked at me in the most amazing way. She was glowing but understated, almost as if I was making this happen and it was to good to be true. I lived for that look. I could tell what this night and that moment meant to her.

We went back to the room and made love for hours. It was the perfect night I never wanted it to end. She even said it was the best date of her life. I wanted soooo many more just like that night.

Author: Matt

Hi, I’m Matt. Just your average uneventful guy. Dedicated Dad, emapth, and nurturer. Going through something I couldn’t possible ever thought possible. My story is called Broken. About an affair at the end of a long marriage and how ultimately I experienced the worst heartbreak of my life. It's honest, raw, and a little bit entertaining. I hope to share my story so people can learn while being therapeutic for myself.

13 thoughts on “Broken – The Perfect Night”

            1. That is probably an entirely different blog. 🤣 I may give some hints at some point in a future post.

              But if you want to know feel free to email me. I am going to be a little more restricted on the blog about it.

              Liked by 1 person

  1. I’ve been pondering this post all day. Hm…

    It’s like foreshadowing. I sense something coming that’s not good and will send you into protective mode. Will H feel cornered? Do something rash, irrational? Will your wife, your kids get dragged in? Will you refer back to the cafeteria scene, the manipulation?

    Very clever writing. 🙂

    PS I’ve never been on a date like this. Sounds lovely.

    But did you still look over your shoulder? I mean, you were still married, seen/known as such by people in the community even if you were far away from home and family…

    Great writing, despite the looming heartbreak we all suspect is coming.

    Liked by 2 people

    1. Hi Cassandra! Thank you as always. I didn’t look over my shoulder. I just wanted to be free for a moment. Maybe I should have but didn’t. No matter the outcome I still try to look back on this night as special.

      Liked by 2 people

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