The Fun Stayed in Portland…

I enjoy ruining endings; Portland was the biggest letdown sexually. Don’t get me wrong, I loved the beer, scenery, the actual reason I was there (running a wonderful half marathon), and the food. However, there were so many reasons for the sexual letdown. First off, I posted too soon on the list of Craig’s (2 weeks is waaay too soon) and then a second time when the first post responders started falling through. The first time I posted, I thought I found two decent candidates. Negative. Then a week before, I posted another. Did it go well? Led to far out in left field miscommunication with a needy individual. Tinder is always full of flakey men, but it was especially apparent in Portland.


A. This is so damn true. B. I've been saving this FOR MONTHS.

So, actual trip time! I was going to Portland to run my 7th half marathon of 2014, and why would I not try to have sex? But I digress…

My flight into Portland was the latest departure time, full of delays and almost missed connections. When I finally arrived, it was close to midnight, but before I even left the rental car facility, I had updated my Tinder to say I was in town for the weekend and started the matching process to see if anyone wanted to hook up since my possible Craigslist guy was MIA (a continuing theme for the weekend.) One decent looking man took the bait; we messaged a bit before texting. He was dragging out meeting like an insecure girl on prom night. He wanted to basically just exchange pics. Annoying, so I went to bed. 

Saturday wasn’t any better; I matched and messaged people that were either busy that weekend (thanks for not reading my profile), didn’t respond, or, my favorite, was all willing…until he then wanted to be super pushy about what needed to happen. No, I’m not finding “us” a woman for a third because women here won’t match with your “bro” personality. Then, an almost hook-up came from an Asian (my kryptonite), who then unmatched me. Now, if you’re not used to being unmatched on Tinder and have notifications on, it is reeeeeally confusing when someone unmatches with you. You’re like, well that message isn’t loading. Why is it not loading? Because they are no longer your match. What a tool. I was texting one of the Craigslist men, who then went MIA; always wonderful. The other one, the one that I thought was a sure thing eventually, was at work and NEVER told me he was off. I literally just sat around, twiddling my thumbs like a loser. I eventually gave up by 10pm since I had a half marathon to run the next morning. 

To conserve my battery while running, I logged off Tinder (but not before I swiped right on probably half of Portland), and kept my battery alive for the instagram pic love. After completing the wettest (not because I was turned on) race ever, toes hurting from the up and down hills, I got in my classy rental car and turned on the Tinder. While driving the relatively quick route to my hotel, a previous match responded and I thought I was going to break my Portland Sucks mentality. Nope, he went silent; it was a huge disappointment since he was pretty hot for a 22 year old that probably lacked sexual experience. Le fucking sigh. As almost all hope was lost and I was going to leave the Hipster capital with only a medal and a sore runner’s body, Mr. Portland responded to me. I quickly, and bluntly, replied that I wanted someone to come over and fuck me before I left to catch my plane. He gave me his number and told me to call him. I told him I had literally just finished running a half marathon, I wasn’t going to be uber flexible and he was ok with it. Once at my hotel, I took off my wet and sweaty clothes to reveal the grossest chaffing ever. I sighed and then screamed while in the shower when the water moved my sweat into the chafed raw areas (below my boobs and between my legs.) At least I would push for doggy style so I wouldn’t have to move and could hide my pain from the running pains. When Mr.Portland showed up, I was not disappointed like I might have been if I had been left with the stragglers at closing time in the ugly bar. Mr. Portland was a catch for a last minute. Wearing my traveling yoga pants, a barely containing my boobs sports bra, and an over-sized shirt, I answered Mr. Portland’s knock. He had dark brown “surfer hair,” some facial scruff, light colored eyes, slightly tan for the northwest, and taller than me with a slim frame. He came in as I continued to pack my bags. Chatting a bit to calm the nerves, Mr. Portland was genuinely nice. With that in mind, I was blunt and to the point with him; I told him to lay down on the poorly made bed so I could give him head. Now, I think I should brag a bit since not only was I exhausted from literally running 13+ miles, but he also repeatedly uttered that he “was not expecting [me] to be this good.” Back handed compliment or not, I enjoyed the satisfaction of knowing he wasn’t expecting my awesomeness on that Sunday.

After a bit and a tensing jaw and impending leg cramps, I told him that he should fuck me. He got up, asked me how I wanted to be fucked, and I just stared at him and then nicely said “I’m already in doggy so…” He tried to shrug off the awkwardness I had created while fumbling for a condom with his jeans around his ankles. Mr. Portland’s cock wasn’t small or even average; it was a perfect fit to me. It had some girth and was probably 7 inches. Maybe four strokes in, and then the super awkward question pupped up: Are you on your period? I quickly snapped back, What, no…

Fuck,fuck, fuck,fuck you IUD and the inability to get your schedule together. He completely stopped, got off the bed and I then decided I should fake my disgust of my vagina revolting in my dismissal of her gift that I left unfertilized. I profusely apologized and then said it must have been because he was so big and my IUD wasn’t used to it. He washed himself off, and just when I thought he might peace out, I somehow convinced him to stay. Mr. Portland wasn’t a quick fuck; he took about 10-15 minutes with some rigorous fucking at one point. When he finished, he washed himself off again; I waited, silently yelling at Catherine for being a Grade A Bitch. To my surprise, Mr. Portland didn’t bolt out the hotel door; he told me he had a great time and wished we could have had more time together. And to inflate my ego more, he told me to call him the next time I was in town. I nicely said that I probably won’t ever be back, but maybe. He left, I showered off again, finished packing and left.

While I didn’t have tons, or even an adequate amount of fucking, Portland was at least pretty. The casual hookups tend to be flakes, and I literally couldn’t even–white girl style. I don’t recommend using Portland as a sex vacation if you’re alone; it may not end well.

Lessons learned: Vaginas are bitches and that you didn’t appreciate their gift of an egg. Sorry, I don’t want a mini me right now, Catherine.

So, what happened to the flakes and MIAs? The one that was working, he texted me while I was at the airport and then continued to try and snapchat me. How about, no. I was perturbed, but I also think I would have been disappointed in his skills. How do I know this? By the way he talked about sex. I think he was honestly lonely. The other guy that went MIA an hour before he was to come over, texted me while I was on my way to the airport. He also wanted to continue to be friends. Do I look like a friendly texted to people who went MIA or silent? I had a limited window and you couldn’t even text to say, hey I’m busy? My luck was shit in Portland.


The Daring Vagina