NOT Your Grandma's Book of Progressive Erotica: Vol 6

Zero To Hero

Going out to the bar on a Friday night to pick up a girl was my forte. I never had any problems picking out the easiest girl there, but I still had standards. There would be a group of women I'd pick from and out those I would pick the one who was drinking the most, or the most interested in going home with me. The system was flawless and allowed me to have a different girl every single week.

Since I had relatively bad luck all throughout highschool and college, my number was quite low and made me feel like a nobody. I never felt like a man with a low number of sexual partners, so I always envisioned popularity coming to me with a higher number. My close buddies always spoke about their conquests when we'd go out, but any time they would ask me, I'd have to say I was too busy to find someone.

That wasn't completely a lie, but it was a combination of that and women not finding me overly attractive in my early years. It seemed they all wanted the cool guys, or the bad boys. I was neither and I wanted to stay that way, until I got my first time under my belt. We were both virgins and good friends. She was fat, but cute enough to fuck for my first time. I was always told, "you have to slay a few dragons before you get the princess".That statement seemed to have some truth to it as I worked my way through a rollercoaster of dragons, goblins, trolls, snakes, swamp monsters, amazon women and then eventually a few decent girls who I got numbers from, but they never called me back.

Getting a number before the end of the night, or before they left my bed after plowing them into tomorrow, was never a top priority for me. Girls came and went like the hours in a day as I worked my ass off to pay for my truck and rent. I didn't make a lot of money as a mechanic at a small auto repair shop, but business was steady due to word of mouth and I was always working on days we were normally closed just to keep up with the workload. My boss was a dick at first, but he eventually gave me the keys to the shop and a decent raise due to the influx of work. I would have opened my own shop if he hadn't to be honest with you.

I had finally caught up on work after pulling many weekend shifts by myself. Friday night was going to be mine again and I was sitting on the cusp of number fifty for conquests. She wouldn't have to be a ten, but I would have to fuck her senseless with everything I had saved up over the past few weeks. I would have to make sure she was crawling out my front door and not just limping like usual.

Taking her clothes off, I made quick work of my own and then helped her finish getting naked. She wasn't a regular at the bar that I knew of and was relatively eager to jump into bed with me. Seeing as I hadn't been to the bar in a few weeks, I was happy to see some fresh meat for me to choose from. Her friends at the bar didn't seem to mind that I was taking her home and the conversation we had was quite short.

Slapping her ass, I slid my cock into her pussy without any foreplay, just my spit. I fucked her as hard as I could and slapped her ass continuously until she was moaning from pain and possibly pleasure. I grabbed onto her swaying titties at one point and squeezed as I drilled her from behind. I always found that the drunk girls were the ones that liked it rough, or at least got drunk so they could handle the rough stuff.

We switched to missionary position where I could barely see her face from the lamp in my room that dimly lit up in the dark. I could tell that her mouth was open as she gasped for air as I thrust my cock balls deep into her pussy without any sign of slowing down. As I had told myself prior, I was going to be relentless so she couldn't walk at all.

I eventually wore myself out and pulled out of her pussy, bringing my cock up to her face and shooting my whole load into her mouth. Pulling her hair back into a ponytail, I held it as I forced my cock down her throat until she swallowed my jizz. To my surprise she had no gag reflex and sucked my cock with no problem. I began to face fuck her and then slapped her a couple of times in the face with my cock and then on her tongue. She was definitely a dirty girl who wanted to be taken control of and as my number fifty, was quite the milestone if you ask me.

When we had finished completely, she said she was going to call for a cab and go home. I had no problem with that and even offered to pay for it since their was still booze in my system. She declined the offer and got dressed, then clumsily walked out of my house after nearly falling over from the shaky legs I had given her. Crawling was the goal, but I got pretty darn close I thought.

As I laid there, thinking about number fifty, I looked around my room and realized that I was all alone. I had done away with dating after a few girls broke my heart and caused me to fall into depression. My doctor managed to help me with some meds and even recommended a therapist, which I tried when I could afford to see her. I let my work consume me to the point of just wanting a quick fuck and nothing more. I was content with living by myself, drinking with buddies and not giving a fuck about the girl I just had sex with who I met at the bar hours earlier. I never gave her a second thought as she walked out the door every time – with, or without leaving her number. My phone wasn't overflowing with girl's numbers, but that's the way I liked it, or perhaps felt was the right thing for me. I guess we all make mistakes in life and sometimes we fall into a trap of comfort, or the easy way out, not realizing that it is consuming us in a bad way.

Number fifty didn't take me from a nobody to a somebody. I thought it did, but in that dimly lit room of mine, I realized I was a horrible person, or perhaps a damaged person who was doing horrible things out of fear, or confusion, perhaps even frustration. I had become something that was animal-like, savage even, something that I never imagined myself becoming when I first fell in love with a woman I cared about. Where did that optimistic young man go and why has he been so distant?

I could ask myself questions all night long until I fell asleep, but the answers wouldn't come if I was asking the wrong person, or wasn't willing to change my ways, now that I had come to this defining moment in my life. It wasn't that I hit fifty on my list of sexual conquests, it was that I had fifty women fuck me, then leave, never turning around for a single second thinking that there could be anything more. I found myself reflecting on my actions and wondering how many other men were out there doing the exact same thing to these girls.

Prior to me, they had probably been fucked and chucked many times over, probably more than fifty times I figured. My number of conquests meant nothing to me now. The idea that it was some sort of rewarding challenge was complete bullshit. There was no reward in fucking fifty women, or a hundred, or even a million. That connection that I felt from five minutes of pleasure to an hour or more, wasn't a connection I wanted anymore. It wasn't real and it wasn't worth it. Having a number to hold onto at night didn't comfort me. It reminded me of how lonely I was and how damaged, empty and lost I truly was when it came down to who I thought I was. I had lost myself through all of those fifty women. They stripped me of all that I was by me giving in to them, giving them a piece of me that I never valued, or thought was somehow going to regenerate itself. How fucking wrong was I.

Hopping up from my bed, I leaned up against the wall as the blood rushed to my head. Once I was steady and able to move, I put my pants on and ran out the door into the cool night air. The girl from the bar was still there, sitting on the porch in silence. I sat down next to her and noticed she was crying.

"Are you okay?" I asked.

She shook her head and didn't say a word.

"Did you call for a cab?"

Again, she shook her head as she wiped the tears from her cheeks. I felt like such a filthy human being as I witnessed her crying on my porch in the middle of the night. I wasn't sure why she hadn't called the cab yet, but I wanted tonight to be a good defining moment. I wanted to change who I was and be a better man from that moment on. The first thing I was going to do was dry her tears and then maybe I'd be lucky enough to find some hot chocolate mix in the cupboard to warm her up.

I put my arm around her and whispered, "Let's go back inside. I don't want you to go."

Words weren't necessary in that moment. She slowly turned her head to me, smiled slightly and then nodded in agreement.