The Worst Lay of My Life

Hi WOTP, I’m Jack and this is my first time writing for Way Of The Player and I’ll be submitting more material in the future.

I’ve been meaning to tell this story for sometime so I figure, why not not. I’m pretty okay with the majority of my decisions and so I’ve never been one to regret much of anything. However, this is by far the biggest and only rememberable regret of my life. I’ll be tasting vomit this entire writing process. I’m hoping that this can be some form of therapy, and that by writing the story out I will have cured my mind of the reoccurring daymares.

This took place about 5 years ago. I was fresh out of a relationship, I was horny on the hunt to get laid as quickly as possible. So of course I took the easy way out and logged onto a dating website and begun spamming messages to every woman I came across. I didn’t bother reading profiles and to be honest, I didn’t bother looking at their pictures either. I was on a mission to hurry and get laid and so I didn’t have time to worry about superficial details like looks (wink). Now of course while, in the act of spamming and responding to hits I never thought I would end up in this type of situation; but anyone who is as horny as I was in that moment can see how not looking at pictures could lead to unfavorable outcomes.

Now before I reveal meat of the story; let me first say that I’ve always had game and I’ve always had high quality girlfriends. The majority of which are 8’s, 9’s and 10’s, maybe one or two sevens depending on your rating system.  I had probably slept with over sixty women at this point.

Back to the part that you actually care about.

So, as you could guess.. While spamming simple copy and paste messages on online dating you’re going to get replies from a lot of fattys. Now to my credit, I wasn’t at all experienced with online dating at this point. I had always gotten my girlfriends from social circles or street/club approaches.

So here I am spamming messages like “I’m pregnant. Its yours”  and I get a hit from this one account, Wanderlust112 ( don’t you dare google it) replying and engaging me in a 20 message banter about having, and planning for a child from the perspective of a male. It was awesome. She was funny, witty, and no online dating awkward one word replies. She made it easy, and thanks to my ego I thought it was my amazing game that had her so open.

Now about her icon picture… Like I said, I was just trying to get laid, I wasn’t paying  attention to photos and I definitely wasn’t reading profiles. I was spamming, just spamming. So…

Okay I’m lying. As the conversation picked up I definitely went back to look at a couple of her photos.. Blonde white girl, with lots of make up, and the perfect “fat girl angles”.  Of course I didn’t know what fat girl angels were at the time, but at that level of horny I was not worried about a little pudginess. If it was going to be a quick same night lay I was going to take it.

After about 22 messages or so, and an exchange of phone numbers  I hit her with one of my classic ask for the lay text messages. “ So are you trying to watch Nick @ Nite with a man or what? lol “

Her of course, being desperate to hook up with an attractive guy responding favorably “ Of course! 🙂 “

She thought I was only kidding at first, and suggested we take a walk around central park before coming to her house so she knows I’m completely sane. I rejected this proposition, and after a little back and forth and me making her feel like she’s not weird or a slut for having some random guy she met on the internet come to her house on the first night without meeting in public she sent me the address and I jump in a cab ride to head her way.

The entire cab ride I’m thinking “ This is far too good to be true. This was just too easy. I usually at least have to put in a 20 minute phone call before a woman is comfortable enough to invite me over without having actually met me. But before I could finish my thought I had arrived, and hadn’t even noticed before arriving that she lived in one of the wealthiest areas of New York City.  I let her know I’m outside so she can page the door man and tell him its cool to let me in. I greet the door man, enter the beautiful antique rope and wheel style elevator, and make my way to her door. I stood before the door and before knocking my gut began to sink; it knew what I was getting into. I doing my best to ignore it, crossing my fingers, hoping that maybe, just maybe she’ll turn out better than I imagine. I stood staring at the door for at least 7 minutes without knocking; patiently savoring the last few minutes of a ‘hot chicks only’ track record before my fate.

I take a deep breath and tap the door twice as lightly as I could, hoping she wouldn’t hear it and I could give myself a good reason to just run out of there. But, nope. Not today. She swung the door open immediately as if she had been waiting there the entire time looking through the peep hole, watching me sweat and worry as she rubbed her hands prepared to take full advantage of the opportunity.

She was much shorter than I expected, so upon her opening the door I hadn’t yet looked down. I was looking over her head and into the apartment. She let out a barry white voiced “helloh” unsure as to whether she should hug me or shake my hand.  I looked down and immediately did the slowest blink of my life. Taking time to read the words “what the fuck” written on the inside of my eyelids. I held a poker face so I wouldn’t hurt her feelings with my reaction. I’m a sweet considerate guy and I was sure after seeing her that she gets enough unwanted stares as it is. But I could tell from her brief frown, before catching herself mentally and forcing a smile that she saw the disappointment in my eyes.

She led me into the home; her first, with me dragging slowly behind. I turned around to lock the door at her request before turning back to watch in agony, as the apartment shaked from everyone of her 300 pound steps to the living room.

I looked up to the ceiling, did a catholic cross by taping my forehead, chest, left shoulder, to right shoulder, and the followed behind her to the living room to continue being polite.

Now I know you’re probably wondering why I didn’t just leave at this point.

For several reasons:

1) I used my last 20 bucks to take a taxi to her place, leaving me with only a train pass to get home.

2) Its winter time in NYC at 2 am, and since I took a cab I wore a thin little jacket  so I would have to walk 30 minutes in freezing night time cold with just a jacket. So I needed to crash at hers.

3)  As sweet gentlemen I didn’t want to hurt her feelings. Its called empathy. If she was a hot chick acting bitchy, I would of left. She never gets that kind of treatment, but this girl.. It seems like she gets treated like this all the time.


I sit with her on the couch and immediately realized that I wasn’t going to be able to look this girl in the face and utter another word without getting wasted. I immediately ask her if she had wine. She told me to go to the kitchen and take as much as I would like. And I definitely did. I chugged one entire bottle straight, and then poured me glass to take to the living room as if it was all I had. The apartment was beautiful by the way; it was an amazing 20’s designed duplex apartment. I couldn’t help but wonder how a 23 year old could afford to live in such a place; Daddy’s baby girl is what she told me. So although I was with Rosannes unattractive step sister, the place did make the experience seem just a little bit better.

After a few more tall glasses of wine I get so drunk that I allow her to pull me head first into her red hairy quooch and I began drunkenly licking like a maniac; the smell was awful, but I did it long enough just to get an erection. She invited me to her bed, I follow her. I didn’t even take off my clothes. I unbutton my pants, put a condom on, insert my penis, and ejaculated in less than 10 seconds. After being drunk, and cumming I passed out and fell asleep. And we all know how we see women we aren’t interested in after we cum, so just imagine what the 300 pound funny girl looked like in the morning when I woke up.

I rose out of bed two hours later with a bladder full of wine; a bit hazy as to what happen and where exactly I was. It didn’t take long though, I looked to my left, and then jetted off to the bathroom to gather my thoughts and take a piss.

The nice guy in me kicked, so now i’m sitting on the toilet like a woman with my chin on my palm peeing trying to figure out how i’m going to get out of here while preserving this girls mental and emotional condition. The brain fog I got was worse than writers block a hour before your procrastinated final paper is due for class. I had nothing.  I looked at the time and it was 5:30, and so I decided I would just slide out the door before she woke up, hoping she would’ve been too drunk to remember what happen. The thing is, she wasn’t drunk. She was completely sober for the entire experience. I’m the one that finished wine bottle after wine bottle. I head back into the bed room and start putting on my shoes as quietly as I could. By the time I get the first one on, I see her tossing and turning reaching for me in the bed. I immediately start rushing to put my other shoe on before she awakes and catches me in the act of trying to escape before she woke up. And just like anyone would imagine, my newly found sense of urgency and fumbling woke her up immediately causing her to ask me “ where you going? “

My mind began racing fast, and I came up with 3 options.. Option 1: Tell her I’m going to get breakfast. Which would make her feel valued for the first time in her life.   Option 2: Tell her I have something important to attend that I’m late for and I have to go. Option 3: Grab my stuff and just run out with one shoe on.

I lift up and prepare to run and stopped as I started to feel concerned. I decided not to run out of there. I turned to her and without thinking said. “ I have a meeting and I’m already running late”.  Her eyes widened as she tapped her phone to turn the backlight on to check the time as she said “At 5:30am on a Saturday?!”. I stuttered while informing her that it won’t be in the city and that I have to go home shower and changed and then take a 2 hour drive to get there on time. The truth is, I did have a meeting that day with a very popular website, but it wasn’t until 11 am. She knew that what I said was a lie, and with a face of disappointment she still managed to ask me if we could just have morning sex one last time before I go. Throw up started climbing up the back of my throat and she started slowly making her way toward me as i nervously said “ I’m going to be late. I can’t”. She was still coming my way. I’m taking steps back, she’s taking steps forward while I’m pleading with her like the next victim being back down in a horror film “ I said..  i have a meeting. I really can’t I swear”. She was still inching closer and at that point I decided that she didn’t care about my feelings at all so I slipped my shoe on untied, ran out the door, leaving the elevator to go down the stairwell and out the front door.

I power walked all the way to the train station and not once did I ever look back.

Moral of the story: If you’re going to do online dating, look at those pictures extensively before you agree to meet up.

The End.

Jack Walls



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