A Whole New Meaning for Ride Sharing

Wow, I’m really spoiling you guys with this frequency. Two posts in two days? Holy shit, is it like 2014 again or something? Haha, might as well be.

Alright, so I just told you about the guy who talked a lot of game but just didn’t deliver. This next one one happened about a month after that in February 2016.  Unlike the last story, this one was an actual pre-planned date, but it didn’t get setup through an app like basically every other date since my first Tinder date. In fact, I had met him previously, but not at a bar or through mutual friends or anything like that. I met this guy… because he was my Uber driver.

So how exactly did this happen? Well it goes back to late 2015 and rather than taking the subway back to my place, I went the lazy route and decided to Uber. Now, before I get too into this, I want to address something: how annoying is it when your driver keeps trying to talk to you when all you want to do is sit in silence? I mean, seriously, how many people out there can agree with me on this?


Cool, thanks team. So yeah, I was in exactly that kind of post-workday mood where the last thing I wanted to do was talk to another human being. But OH MAN when this guy’s photo showed up as my driver while I was waiting for him, you bet your bottom dollar that my mood perked up. Like, I can barely find any bearded men I’m attracted to during an hour-long Bumble swipe sesh but yet the magical Uber radar managed to connect me to this beautiful man on a ridesharing app. Hell, I’ll ride him all day even if it means I have to share him.


Bahaha couldn’t help it.  But yeah, funny how that works. Anyways, he pulled up to get me in his black sedan, and I was pleasantly surprised that he was quite attractive in person from what I could see from the backseat.

We chatted the entire ride to my place, and I was SO CLOSE to asking him out before I got out of the car, but I totally chickened out (people still say that phrase, right?). I was kicking myself after the fact and decided I’d use my only remaining connection to him to give it a shot: his post-ride rating and comment. I wrote something along the lines of, “Hey Uber, if [his name] is single, then tell him to contact me so we can meet up for drinks [then provided my cell].”  I didn’t hear anything from him or Uber and so eventually I guess I just forgot about the whole scenario.

FLASH FORWARD OVER THREE MONTHS to February 2016. I’m at work and receive a text from an unknown number: “Hey do you remember me?”


I replied with, “Should I?” and sure enough it was the hot Uber driver! Apparently he hadn’t logged into the Uber app for months and had finally done so and saw the comment I had left him. I was completely not expecting him to suddenly reappear, and on top of that, it was unbelievable to me that he was single since literally every attractive male I meet in person is in a relationship. So we made plans and here’s how the two dates (yes! more than one!) went down…

Date #1: The Grand Unveiling of… Me

Something I didn’t really think of going into this date was that the comment I had left him was anonymous and from over three months ago. Yup. This guy was essentially going on a blind date since there was no way for him to actually confirm who left him the message. Know what that also meant? He didn’t even know my name going into the first date. I could have been literally anyone he’s ever driven.

He did admit, though, that he had a feeling it was me because of the date I’d left the comment and that I was so memorable. *blush* OH, and get this: he had actually wanted to ask me out at the time when he drove me but it was against Uber rules since I was his customer. Well geez, thank goodness I commented! Like for all I know, the only reason I’m single is because all the good ones are held back from me via who knows what regulations exist out there!


Shut up, Marsha. Awesome, so yeah that’s what I’ll keep telling myself.

The date itself went well and there weren’t any Dating Problems that I can recall now nor that I had originally written down in the draft post I made just after going out with him. He was still attractive, interesting, and was making all the right moves as we sat next to each other at the bar. Afterwards, he walked me to my apartment since he already knew where I lived, and before I knew it he was fingering me up against my apartment door (like in the hallway OUTSIDE my apartment… really unsure how I allowed that to happen so out in the open). Soooo yeah it clearly escalated quickly and I definitely could have just let him into my apartment, but considering the fiasco with the 10-inch fakeout guy and that I had just recently begun sleeping with that almost-two-year guy, I figured there was no rush to immediately bang this one.

Hahaha so in a true sign of practicing patience and self-restraint, I waited a full week and a half.


Date #2: Most Convenient Post-Hookup Uber Experience Ever

I’ll be honest, I don’t remember a whole lot of specifics about the actual date. He picked me up in his black sedan and we went somewhere for drinks and apps.  The date itself wasn’t bad but it also wasn’t memorable at all. THAT SAID, our apartment hallway makeout sesh from Date #1 had been very memorable. Since I wasn’t sure a third date was something I was for sure going to want to invest time in, I was hundo percent down to pick that hookup back up now while we were still together.  He must have been thinking the same because at the first red light on the way back to my place, he leaned over to kiss me… which led to us making out… and getting super touchy at every stop… and yeah we were really getting after it so I told him to head to his place instead of mine. Don’t you love how Uber gives you the ability to switch destinations mid-ride like that?

We got to his place, he made us each a drink, and I think we maybe had like two sips before I was laid on top of his kitchen table and he was going down on me.


Since he had a roommate who was probably going to be home soon, we gradually moved our way to his room, losing more and more of our clothes along the way.  Literally the second we made it onto his bed, the condom was on and boy did I have high expectations given how hot and heavy he had been with me so far. We started having sex and I was loving how he was taking full control and being amazingly aggressive and I was on the road to getting my world rocked.

But then.





Yep. He came.

I’d be shocked if it was more than three minutes. It really was a shame because while he was going he was doing great. I won’t hate too much on him because I get this sort of thing can happen and even he seemed shocked/embarrassed that he came so quickly. In fact, I give him props because since it was clear as day I hadn’t orgasmed, he wasted little time to go down on me and finger me and put in a real effort to get me there. I feel bad because I did end up faking it… but that letdown had just messed with my mindset and I knew I was not going to get there at that point. He wasn’t bad; it just wasn’t going to happen, and I didn’t have it in me to tell him after he knew I also wasn’t thrilled with our short-lived sexcapade.

I immediately got changed to make it clear I wasn’t going to be staying the night. Fortunately it was a weeknight so it wasn’t a completely savage move to just up and go. I said I’d order myself an Uber (ha), and he STILL offered to drive me home. I wasn’t sure if refusing it or accepting it was the correct way to go… so I took it!

Never ended up seeing him again, but… that, my friends, is how you get a free Uber ride.


Ten Inches of Disappointment

Hi again. Yes, I’m still alive. And yes, I know we’re almost entirely done with 2017 and I still have yet to update you on any dates from 2016.  But since I recently completely ended things with the guy I’d been regularly hooking up with for almost two full years, I’m too poor to go out until Christmas money starts coming in (really counting on you, fam), and the red wine I’m drinking is making me feel creative, I figured I’d finally brush the dust off these posts I’ve had drafted forever and send them off into the world.

As I’ve mentioned before, 2016 was a bit of a wild year for me and so only a few will be getting a dedicated blog post. But the ones I do post will be in chronological order… and fortunately, this first one is one of my all-time faves.  Prepare to be indulged.


Let me start by laying out the scene for you because this was not a pre-planned date or meet-up or anything of that sort. It was a Thursday night after work in January 2016, and I was getting ready to leave the bar I’d been drinking at for a fundraiser for the past few hours (funny enough, the fundraiser was hosted by the guy I mentioned I just ended things with, and this happened literally two weeks before we hooked up the first time). I was drunk, but nothing outrageous. My coworker friend left at the same time as me and she hopped in a cab while I continued walking by myself towards the subway which is how I decided I was going to get home. All of this I completely remember. Then…

Part 1: The Shortest Blackout of My Life

I must have blacked out for a total of 2 minutes tops. It could not have been more than that because next thing I know, I’m no more than 30 paces from the exit of the bar, and I’m making out with some random guy. On the sidewalk. No clue who this guy is. Never seen him in my life.


Since there was no one else around, I have to rely on what he said happened as truth. Apparently he saw that I had just left the bar to which he was headed, he asked me a question which is what got us talking… and then we started making out. Honestly, at the time I was so confused but also intrigued that I didn’t dig too much more into it. Plus, we continued making out on the sidewalk so that kind of limited conversation. I KNOW this makes no sense but he was super tall and a decent kisser, so I just went with it. That had literally been the shortest blackout of my life because from this point forward, I remember everything.

Part 2: From the Uber to the Park

I told him I had to get back home, and he said he had to go back as well.  Again, I really wasn’t wearing my Olivia Benson hat because otherwise I would’ve called his bullshit since he had just told me he had been on his way to the bar when we started talking. But I digress. So he ordered an Uber, saying he’d have it drop me off then continue on to his apartment. Since the plan was to go our separate ways, we swapped phone numbers then made out the entire ride to my neighborhood. I had the driver drop me off at the park near my apartment since I didn’t want him to know which building I lived in. Cuz yano, gotta look out for my safety.  Then he hops out of the car as well, and probably because I was super turned on at this point, I didn’t get creeped out at the fact that this guy was essentially following me. Cuz yano, I was clearly looking out for my safety.  We continued to make out on the park bench for a few minutes… then he decided he had something important to tell me.

Him: “I have a huge dick.”




Me: “Oh, uh, ok, did I just hear you correctly?”



Him: “Yes, I have a 10″ cock.”

Naturally, the only response I had to that was, “Ok, let’s see it.” So I took him back to my apartment to avoid the risk of arrest for indecent exposure. Cuz yano, safety.

Part 3: The Fun Begins

Once in my apartment, I took him immediately into my bedroom and closed the door.  He tore my top off, but I stopped him before he could get his hands on any other articles of clothes because there was a purpose he was there: I wanted to see this gigantic penis of his.  I made him remain standing, and my skepticism was building as I was unbuckling his belt because I wasn’t seeing or feeling anything yet. Pants drop. Still nothing. Boxers off… flaccid.


I’m not sure about any of you, but having a limp dick stare at you in the face when you were expecting this 10″ rod is not only disappointing but also super gross. They are not cute. It’s one thing when they’re only at least partially hard, but when the sucker is just dangling there lifelessly, then there is zero chance I will be doing anything with it. You gotta meet me at least part of the way there.

So with his pants and boxers still around his ankles, I stand up in front of him and ask, “Alright, where is it? I only see about two inches here.” His first plan of action was to begin aggressively jerking off tugging at his worm-like penis, but that had no effect at all. Next, he asked me to take my bra off; feeling bad for the guy/still wanting to see this ten-incher, I did just that and we made out against the wall for a bit. No luck. Still soft.

This brought him to his last attempt at trying to get hard: telling me to put my mouth on it.


For the record, I actually really don’t mind giving head to people who I’m hooking up with regularly and trust.  But strangers are a totally different story.  Now add in the fact that this stranger’s p was also soft, and it was enough to completely kill my DTF-status that night. It was time this ended.

I grabbed my shirt, put it back on, and immediately I saw the panic in his eyes that this might not be happening for him. Things turned savage pretty quickly.

Me: “It’s time that you go.”

Him: “No! I just need another minute!”

Me: “At this point, I have no reason to believe you are even close to 10 inches.”

Him: “I make girls cum like crazy, you have no idea.”

Me: *major eye roll at his last comment* “Congratulations but I’m ordering you an Uber.”

Him: “NO! You are so hot! I will die if I leave here tonight without fucking you!”

Me: “Please don’t die, but you are leaving.”

Him: “Let me go down on you, and then I’ll be ready to fuck you.”

Me: “Nahhh I’m all set.” *ordered him an Uber*

Fortunately, the Uber didn’t take too long to get there, and I managed to force this guy out the door. Unfortunately, I had given my number to him earlier in the Uber together. I’ve since deleted the texts, but based on his confident tone, he clearly did not pick up on the fact that he failed pretty miserably that night. After not responding to his persistent texts for about two weeks, I finally replied saying he must have the wrong number.


Despite that one and only reply, I continued to receive occasional messages from him as if I’d never said anything. Aside from one or two texts where he said he was going to be in the neighborhood and was going to stop by (thankfully, he never did), the rest of what he sent me were desperate attempts to get me to meet up with him. I kept my silence, and eventually he stopped trying.

So there you have it. This is what set the tone for my 2016 dating hookup single life.