Broken – Dating

Here we go… I launched my Tinder, Bumble, and Hinge game for the first time as a single person. I was putting myself out there. It was scary. I had to put Hailey out of my mind.


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

Here we go… I launched my Tinder, Bumble, and Hinge game for the first time as a single person. I was putting myself out there. It was scary. I had to put Hailey out of my mind. After all she hadn’t given me much consideration while dating some guy 10 times just a couple months ago. The empath justice side of me was coming out in full force.

First week I had 4 dates… whoa that was waaaay too much. Sometimes I had 2 dates in one day. I noticed something early on. I was really uncertain about the way people felt about me. The dates were pleasant. But was it something I was doing. On one of them I nearly broke out in a full sweat. Maybe I wasn’t ready for this, then it happened.

Somewhere on the 4th or 5th date I was out. I was doing well. Maybe it was just me relaxing. Charming she was having a good time we were laughing share and appetizer. We pretty much closed down the bar. I did like her but there was some red flags. She was attractive, tall, blonde (fake), boobs (faker), and sweet but kind of a mess emotionally.

I walked her to her car and gave her a kiss goodnight. Or so I thought. She said what are you doing now… I was like ummmm going home. She asked “where is home?” I lived only about a 12 minute drive from where we were. She said “I will follow you.” I just went with it. We drove back to my place and continued to drink. I just spoke with her. I was nervous about it going too far. So no additional moves were coming from me. Not on purpose. But i wanted to be respectful.

She finally broke the ice on what was going on. She said “you really are a good guy aren’t you?”. I just said. I guess. “She said it’s ok, we are going to fuck tonight if you want to.” I couldn’t believe it. I was turned on by it. It was 1 AM we were up all night already so no time like the present.

I stood up off my couch grabbed her hands stood her up and kissed her good. I wasn’t going to go crazy. I just led her to the bedroom and undressed her slowly. I could already tell she had a great body. So I wanted to unwrap it like a present. I don’t think I was every with a woman as tall we were eye to eye.

As I had her down to her bra and panties I twisted her around with her back to me and I pulled her in and kissed her neck. I just held her for a few minutes. I could feel her anticipation my hand ran over her breasts (definitely fake, but nice), then down in between her legs. I went right under her panties. I firmly touched her warm wet spot. I unhooked her bra and let her stand there naked with my hard cock pressed against her ass.

While playing with her nipples. I peeled off my clothes and pulled the blankets down the bed spun her around and laid her down. Before I climbed on top I pulled her panties off. I grabbed a condom from the night stand and put it on. Climbed on top and assisted myself in her. I was just going slow. I didn’t feel quite myself. Part of these moves were me but not. Almost like a puppeteer or lip syncing.

I started to find some sort of rhythm but I wasn’t great. She moaned I could tell it wasn’t her greatest experience as it was not mine. But I forged on I pushed inside repeatedly. I couldn’t get in the present moment. I apologized and said you are the first person I have been with in a few years. And it was true I had only slept with Hailey in the last 3 years of my life to that point. She said something I didn’t expect. “You are doing alot better than you think you are.” Flattered I finally snapped into it. I started remembering to use my hands, eyes and mouth. I was kissing her and giving her great nipples some attention. I could hear her moans build and she came. And seeing it is way past bedtime it was my turn. I turned a slow burn into something more rapid and then I came… and thought “that wasn’t so bad. I did it.” Then she did the most unexpected thing. She got up and came back with two drinks. And I thought “Oh my god, the night isn’t over.”

We drank and fucked and drank and fucked. I was out of gas as the clock turned about 4:30. She was the energizer bunny. It took me about 4 days to recover. We spoke after but I literally couldn’t make plans with her in fear of the 3 day hangover. It was probably a good first experience minus the recovery time. But it was also hollow at the end. I felt like an addict getting a fix. And I missed Hailey…

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.

11 thoughts on “Broken – Dating”

  1. I appreciate this perspective from the man’s side, trying to move on and nurse a broken heart at the same time. And when you wrote at the end here that you were still missing Hailey….aww man! Love, dating, fucking… all of that is just kind of a beautiful mess, isn’t it?

    Liked by 1 person

  2. I haven’t had a sex hangover in years, I hope to have one soon. But I get how you were feeling hollow. You needed more than sex, you needed a connection. As I’m ending my divorce I’m not looking forward to the dating scene, I never was a serial dater, and I never had sex just to have sex either and yet I have a high freak factor (I’m a hot mess lol).

    Liked by 1 person

    1. So you have kink and like sex but are just reluctant to have sex to have sex? lol!! I hear you. I fall into that category myself. Somedays you just have to grin and bear it for yourself. Even if it is just a quick fix. Sometimes it’s better than being lonely.

      Liked by 1 person

      1. Oh I love sex, lots of sex and lots of foreplay and yes lots of kink. Unfortunately I am married to a man I haven’t slept with in 13 years because of his abuse of pain meds. So I truly feel sorry for the first bastard I sleep with, I may break him lol

        Liked by 1 person

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