Broken – Catch 22

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

Nothing like life giving you one of those damned if you do, damned if you don’t things. It would have been great if I met Ashley in the spring. It would have even been better if Hailey never left me.

But here I was caught between winding down Ashley and ramping up Hailey. Or vice versa. It was only a challenge because of Hailey’s availability. Otherwise it would be more obvious about what I would want to do. She said it may take her til the end of the year as well as James expressing to give him til the end of the year. Another delay tactic?

Hailey is such a wildcard but my heart was really with her. It was that chance to have what we dreamt about for 2 years. In my quest to figure out how would it be different this time. I failed to ask just simply that.

But she was saying all the right things. Showing me so much love and interest. And quite honestly when you want to be with someone so bad it is difficult at times to invest that energy into something else.

I still had time. I was giving myself a couple weeks to figure it out. I would continue to see Ashely and talk to Hailey. I would even see Hailey sparingly. When I started to settle without the anxiety my desire for her started to return.

One day she came for lunch. But she didn’t know she was on the menu. lol. I grabbed her almost the minute she crested the door. I scooped her up brought her to the bedroom undressed her in record time. Although it was Hailey. No panties just a bra and a long sundress. I flipped her down head hanging off and basically fed her my cock and dived into her pussy. I was sooooo maniacally going down on her. I was targeted and sloppy just trying to overwhelm her with stimulation. I could hear her simultaneously gag and moan it was an amazing sound. We did this for quite a while. When it was time to cum I got up rolled her over and went to the other side of the bed grabbed her ankles and pulled her to her hips were at the edge of the bed. I penetrated her and fucked her hard until I came.

I needed it. I needed to re-establish myself in this dynamic. I didn’t like how sensitive I had become to her. I was just always questioning not enjoying her presence and wanted to change it a little. She even commented later that “I think 69 is my new favorite thing.”

It was probably in that mindset that I had started the idea of winding Ashley down. It wasn’t conscious but I knew it wasn’t fair to not have her know that my heart wasn’t fully in it. So I started to have a conversation with Ashley about where we are going and it didn’t take her long to say… “Look it’s ok if you see other people. Still kind of exploring dating myself. But I would like to see you because I really like you and am attracted to you and sex is important so I would like to see you at least once a week.” Huh? Didn’t see that coming, although looking back Ashely was the straight shooter and a realist. Can I have my Ashely and eat Hailey too? I am probably not that lucky but let me see how far this goes.