Have you ever had sex and it was so bad that you felt like you owed your vagina an apology when it was finally over? That was me Sunday night. I have for the most part sworn off one night stands and fuck buddies, but I have been really in my feels lately trying to figure out what I’m doing with my life and just generally disappointed by dating in general so after dinner and a few drinks with friends when the opportunity for a hook up came about I took it.
I had recently changed my tinder settings to include men ages 21-35 which I think makes me a cougar but I’m not sure. I don’t really know why I decided to do it but I think it was a combination of me being sick getting weirdly timed poorly lit selfies from middle-aged men and I maybe had gone on one too many dates with men over 30 who for the most part haven’t learned that you cant hurt everyone who tries to care about you just because someone did it to you. On day one I matched with some 22-year-old kid who wasn’t far away from me. He was pretty adamant that he was going to somehow manage to rock my world. I guess I did kind of set him up for failure when he told me how women have told him how “good he was with his hands and tongue” to which I responded, “yeah no one is ever going to tell you it was terrible but thanks for playing”.
When he was messaging me earlier in the day I said it was a possibility. I knew I had been super in my feels and probably needed to get some and I also knew I was gonna have a few drinks so I figured I would leave it open-ended so that if I was feeling like I get some cradle robbing strange I would have the opportunity to. Around the 6th vodka soda, I mentioned that I might be into it. Next thing I knew he was in the car on the way to Worcester and at that point I felt bad about backing out so I just gave him my address.
So he comes over and he’s a nice enough kid. We start getting things going and he can’t uh… rise to the occasion. He starts losing his mind and literally SLAPS HIS OWN DICK. I’m just sitting there like woah- we are in my own house- how can I get out of this. I thought he was going to cry. He finally ends his limpdick induced breakdown and we start hooking up and suddenly I wasn’t sure if I had a vagina or a construction site down there because he was like a god damn jackhammer. The whole ordeal only lasted about 20 minutes but damn it was the longest 20 minutes of my life. It was one of those experiences that made me wish I had never moved my emergency hammer away from next to my bed.
I’ve made a career out of trolling guys on Tinder. Its become basically the only hobby I have, that and going on dates with guys who mostly aren’t right for me. A few months ago I met this guy who lived on the Army base near a restaurant I worked at in high school. He was hot, and in the army which somehow made him 10x hotter, and he was charming and funny so when he asked me to meet him for drinks I didn’t hesitate.
You ever end up on a date with someone that is just so good looking that you feel like your being punked because they are way too hot to be hanging out with you? That was how I felt on this date, and I almost never feel like someone is out of my league but I felt like that on this date. We had so much in common that I felt like I was on a date with myself. It was one of the few dates that when it ended I knew for sure I wanted to see him again. We made plans the next day to go for drinks later in the week and he asked me if I would consider going to the military ball with him in April if we were still hanging out. I love a good ball so obviously, I said hell yes.
After that, he started being kind of a dick and bailed on our date for later that week, didn’t make plans to reschedule and eventually just kind of disappeared. I’m not that girl who is gonna pursue someone who is clearly not interested in me or waste my time trying to talk to someone who doesn’t make an effort to try and talk to me so I just moved on and continued going on a bunch of dates and kind of forgot about him until Easter when he texted me clearly hammered trying to get a booty call. I guess something about Christ rising from the dead really got his engine revving. After a few different versions of me telling him there wasn’t a chance in hell that I would ever sleep with him he eventually stopped texting me.
I didn’t hear from him again for over a month until one Saturday morning when he texted me “I don’t care if you won’t fuck me….I just want to be friends”. I can get down with that. One of my closest guy friends is a guy that I had hooked up with a few years ago who completely ghosted me after. When he first started messaging me I totally hated his guys but eventually, I came to terms with the fact that we would have really sucked together anyway and the worlds greatest friendship story was born. I didn’t expect that that would be the case with this guy, but since I have been struggling to make new friends any way I figured at the very least I could give him a chance. It lasted about four hours up until he asked if he could take me home after my shift that day. That was about when I realized that we both had very different ideas about what friendship was.
I thought that was gonna be the last time I heard from him but he proceeded to text me every Saturday for like a month with some variation about how he wanted to just be friends and complain about how terrible his life was. Which I get it, he’s seen some shit and he needs someone to talk to, I can respect that and I can lend a sympathetic ear but then he would get progressively drunker as the day went on and start trying to bang me. Eventually, I just started resending him screenshots of our conversation from the previous week to save us both the aggravation of rehashing the same conversation over and over. He claimed he never remembered any of it and I think he actually wound up blocking my number during the most recent conversation because I wasn’t giving in to banging him. I guess the moral of the story here is- Block everyone they aren’t your friend .