Over the weekend I attended a convention in Chicago. I booked my hotel in advance, and checked my itinerary the day I left. I realized that I had booked the wrong hotel. The one I wanted was con-adjacent, and the one I booked was not as close, mistake made because they were the same chain. Anyhoo, day one goes ok, but I am starving. I go eat way too much at a steak place, and go back to the room feeling really full. My next decision is what to do with the rest of my night, find a karaoke bar, or go find a bar with the UFC fights. My belly was hurting from eating too much, so I decided instead on a whiskey at the bar. I popped what remained of a weed edible and went downstairs.Turned out to be a great decision.
At the bar was a female bartender, and what I initially thought was a couple. They were both blondes, he was wearing a wristband from the convention, she was not. They both spoke with heavy European accents. He was HAMMERED, to the point he couldn’t remember he had a drink in front of him, so he went to bed. She plopped down next to me, and we started talking. She was really hard to figure out at first, she was wearing a bright pink GAP hoodie, and a front facing acid wash fanny pack and brightly colored cowboy boots. She looked like she could be from Indiana, but the accent meant something else. She was in her 40s that I could see, but hey, so am I. We got to talking, and she started buying me drinks (maker’s on the rocks). Turns out she was from Switzerland, and was just returning from a solo dude ranch vacation out west. By my second drink, it seemed like my night was going to take a turn for the better.
Soon a wedding party came into the bar, and the place started getting louder. She complained about being warm, and took her hoodie off. I actually stopped breathing for a moment when I looked at a stupendous pair of C cups straining against a tight pink top. She saw my expression (couldn’t hide it), and laughed. She regaled me with stories of the teen ranch hands ogling her, and I said when I was that age, I know I would have been as well. She said she hadn’t gone to her room yet, and wasn’t sure where it was. I asked what number, she says 612. I was 625. Sealed. Done. Happening now whether I want it to or not. The Gods have spoken.
She got up to use the bathroom, and the bartender said “Wow, you going to hit that?” I about spit out my drink. I told her it seemed that way. We decided to cash out, because if i had a 4th Maker’s I would pass out, and I was getting high as giraffe nuts by this point. We adjourn to the elevator, and push the button for 6. Her room was before mine, so we both stop. I joke that it looks like my room, which breaks some tension. I tell her I’ll be back (I had to drop my wallet off, just in case). I come back and it’s game on.
We kissed passionately, while frenetically tearing our clothes off and pawing each other like horned up teens. Off came an item, more groping, another, groping. When she took off her bra, I nearly wept. I hadn’t seen breasts that perfect on 25 yr olds. They were each a nice handful, no sag, with half inch nipples standing at attention. Her waist tapered down into her jeans, which fit perfectly. I removed her pants. and laid her on the bed. She was wearing blue silk full back panties, which I ripped off from the back, exposing an amazing pert ass. I turned her over and she was shaven bald. I took in the view for a moment. This woman, who I met only because I booked the wrong hotel, had the best body I had ever seen waiting for me . I proceeded to go down on her, making her come with accented orgasm sounds (!). My tongue and fingers worked in tandem to bring her to several climaxes. Unfortunately the weed was giving me wicked cotton mouth, so i stopped. I mounted her from on top, and she would orgasm every few thrusts, keeping me from building a rhythm to my own release. Just when I thought I was coming, she’d fall off my cock and start spasming. I lost count after a while. She orgasmed in every position we did. She was petite, so she was easily maneuverable into all kinds of positions. It was getting pretty late, and we were still fucking like kids. In fact I think we both forgot we were booked in a hotel, until I heard the neighbors door slam in what could only be frustration. Breathing heavily, she said she needed a break, I figured we were fucking for over an hour at that point, and the weed and alcohol were helping. She said I could stay, so I did.
I woke up at 5 AM, and memories of what had occurred came flooding back. Blood started flowing to my cock again, at which point I remembered, SHE’S RIGHT FUCKING NEXT TO ME. I began rubbing her back, and she moaned her approval. She cuddled up to my chest and began jerking my hard cock. I couldn’t take any more so I climbed behind her and we fucked some more. Again I would get close, but again she would come off to cum, her face in the most beautiful expressions of agony and ecstasy I’d ever witnessed. She got on top, and I grabbed her pert little ass and began to thrust. I finally got a good rhythm going and told her I was coming. She did not fall off, in fact holding on to me while I emptied my blue balls inside her. She kept bouncing up and down until I thought I was exploding. We must have been really going at it, because the neighbor’s door slammed again. We had a good laugh about it. After that I said I needed to get some sleep (still had one more day of Con), and I had to be there at 10. She said to see her before I left. I went back to my room, and passed out, waking up several times to check the time. Checkout time was 10, and I woke up at 9. I went to her room to say goodbye, and asked if I could take her picture, just so I could remember she was real. It was the perfect set of circumstances that lead me to what was the best fuck I have ever had. For the rest of the day, and into today, I still have a stupid grin on my face.