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The Hardest Goodbye

Sep 22, 2024

7 min read

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Ever wake up one morning and feel like something isn’t quite right? Nothing has happened out of the ordinary, nothing surprising or unfortunate, but something just feels off. This sense of wrongness happens often in prison, and it occurs with such frequency that it can be difficult determining the cause. Honestly, the last couple of months of my life have been the most productive I’ve ever been. I truly believe that I’m making a difference and fighting for what I believe in no matter the cost, but I knew something about this weekend was off. Now that I’ve realized why I’m feeling like this, it all makes sense. A year ago this weekend was the last time I spent with the only girl I think I’ve ever truly loved.


Twenty-one days out, I got the letter that told me when and where I had to report to prison. This was like finding out I had twenty-one days to live, twenty-one minutes left on the clock where, when the time runs out, life as you know it is over forever. There’s no word that can explain that feeling. Devastated? Shattered? Nothing does it justice. During these twenty-one days of absolute loss and hopelessness, there was only one person in the world that I wanted to see. I hadn’t seen her in person in over fourteen months, but I knew I couldn’t go to prison without holding her one last time. Many things had happened during the time we’d been apart—I could point fingers, as could she—but none of that mattered now. All that mattered to me was being able to hold her close, look into her eyes, and tell her I was sorry. The truth is that I hadn’t been there for her in her darkest hour; I had failed her when she really needed me. I had my own reasons, and a lot of them were valid, but when you really love someone, none of those things should matter. There was no way I could let myself go to prison without being able to apologize for everything in person. It just so happened that a friend of mine was scheduled to be driving through New York anyway, so I caught a ride with him and headed up to see her one last time.

I was an absolute emotional disaster leading up to and during my twenty-one day countdown. Depression over the entire situation had compressed and compounded into an entirely new feeling, one that was an absence of everything. It feels like being numb, but there’s no word for the ocean of emptiness that waits at the end of depression. Here I was, in New York, finally able to look into the eyes I had fallen in love with once again. She was absolutely beautiful, in the best shape I have ever seen her in, but on the other hand, I was in the worst shape of my life. When she and I were together, we had taken great pride in always looking hot. I had let myself go completely, and to be honest I was very self-conscious. None of that seemed to matter to her though, she took me right in and I felt loved again. Things were different, but the love we had for each other couldn’t be denied.

After we hugged and spent some time just embracing each other’s company, that spark we’d always had lit up again. Daddy’s dirty little slut had been bad while he was gone, and she needed to be punished for it. We had talked on and off through the time we were apart, so I knew about some guys she had fucked. She was in the middle of showing me different lingerie she could wear for daddy when I sat down on a chair, grabbed her by the waist, and bent her slutty self over my knee. I spanked her perfectly tight but juicy ass and asked her if she had been bad.

“Yes daddy, I’ve been really bad. Are you going to punish me for it?” I told her to show daddy what she had done the last time she had gotten a spanking. She got on her knees and pulled out my cock and started sucking it with a passion. She’d told me before I got there about another guy she had fucked that would bend her over his knee and spank her. I could tell she was re-enacting the way she had sucked his dick, and for some reason I found this extremely hot. I got up, picked her up off the floor, and bent her over the bed. I asked if she was ready, and she begged to be punished. I fucked her bent over the bed until I couldn’t keep myself from eating her pussy. I pulled my cock out and tossed her down on the bed; it was my turn to atone for my sins.

I spread her legs open and I spit on her pussy, kissing all around it to tease her. She asked daddy if he had missed her tight little pussy, and indeed I had. There are some girls that, when you put your mouth on them, there’s a special kind of connection. It truly feels to me like I know exactly what her pussy needs. She asked me if I liked eating other girls’ pussies and, I couldn’t lie, I had. I told her to make me eat hers exactly the way she liked, so she grabbed the back of my head and controlled my mouth, pushing it down on her when she wanted me to go harder. She would lift it up if she just wanted me to lick it lightly. She loved to make herself cum with my tongue. Other guys might eat my dirty little slut out, but no one does it like daddy.

After she punished me by cumming on my face, I got on top of her. I put myself inside of her, but this time the mode switched. Hot, dirty, daddy sex is awesome, but we really loved each other, too, so the sex turned more passionate, imbued with that intense, emotional connection that pure love generates. I looked her in the eyes while I slid myself back and forth, deeper and deeper inside. I grabbed her by the back of the head and made her watch my cock go in and out of her. She started playing with her clit—it was so hot to watch—and she begged daddy to let her cum. I wanted to feel her cum on my cock again so badly, so I said yes, baby, please cum on daddy’s cock. Her legs started to shake; I could always feel when she came. As soon as she had come, I spun her around to punish her again and started pounding her from behind. She had a mirror hanging on her closet door, and I made her watch daddy pound her. I asked her if she liked when other guys got to pound her, and she told me that she did. I pounded her harder, and she started begging for my cum. But she had been bad, she couldn’t have it. I asked her if other guys always came when they pounded her from behind, and with her ass, I already knew the answer. Daddy was different though, he could control it, and I wasn’t done reminding her of one of the main reasons why she loved me.

We switched positions and she got on top. She is truly a cock-riding master. A lot of girls have ridden my cock well, but my dirty little slut had a special talent. She really does ride dick the best. She started riding my cock while looking at herself in the mirror, her abs in clear view. Her body was so fucking tight, she was the hottest I had ever seen her, hands down. She was soaking my cock with her cum, splashing up my body to my chest as she slid back and forth. I loved feeling her squirt over every inch of me, and I was ready to cum with her. I could tell she was building up, and she started asking me if I was ready. I knew it was time to finally let her have it.

“Daddy, I need to cum. I need you to cum with me,” she breathed. I told her I was ready, that all she needed was to beg for my cum and I would give it to her. She moaned, “Daddy, I’m cumming, please fill me up, daddy, I need it right now.” I could feel myself pulsating deep inside of her, and this made her cum even harder. There really isn’t a better feeling, cumming at the same time as someone you honestly love.

We went on to spend the weekend together, but the sweetness of our time together was touched with a bite of the bitter. It was the end. I knew it then just as I know it now. Even though I’ve still talked to her, even though I’ve held on to the hope that one day I’ll be out of here and we’ll reunite, it really isn’t fair to her or myself to cling to this fantasy. What we had was incredibly special, and for that time in our lives we were each other’s “one.” I think that sometimes we get so caught up in the idea that there is this magical forever “one” that we forget to appreciate the people we love for a season of life.

I hope she meets the next man to make her happy. I know I’ll be fine when I get out of prison, and I need to spend this time perfecting me. That’s why our story needed an ending, so that I can find the closure I need to close the chapter on someone I deeply loved and connected with. If only turning the page wasn’t so fucking hard.


Sep 22, 2024

7 min read

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