Wingmanned by an Entourage

What ever happened to Boy #1 and Boy #2 from my post Failing my Break From Boys? Well nothing has happened with Boy #1… but if I wasn’t so occupied with Boy #2, I might have had more time to write blog posts.

About a month ago I met Boy #2, Chase, we continued to message back and forth on Facebook for an hour or so the first night we met, I gave him my phone number, and then texted well into the night. When he messaged me, at one point he sent a cat sticker with a donut. He found my sweet tooth. He later invited me to his band’s show, I told him I would go if there was donuts.

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The next day, my roommates had band practice and one of them texted me saying to guess who has a practice space next to them. I quickly guessed Chase’s band. I was right. I took a screenshot and sent it to Chase because the night before we had played a little bit of a guessing game which I kicked ass at so I had to brag about this guess being correct as well. We then texted back and forth with some flirty banter which lead back to my sweet tooth. He then questioned if there was more to me than just my love for sweets, I ended the conversation to go to bed and leave some mystery.

Thursday couldn’t come soon enough. I was eager to see Chase again, but I knew I had to be patient. Being that his band was performing, it wasn’t really a date, he just said I should come see them. They were playing at a bar in Wrigleyville… not quite the scene my friends hang out in so the challenge I faced was getting at least one of them to come with me so I wasn’t showing up alone.

I asked my roommates. All of them refused. I asked my gay husband. He said maybe, which usually means no. I then asked my friend and her boyfriend and another friend. They were all reluctant because Wrigleyville, but I did just give them a ride to and from the airport, so one of my friends and her boyfriend agreed, the other said maybe.

When Thursday came, my friend and her boyfriend met up with me before the show to grab dinner beforehand. I haven’t heard from Chase at all since Sunday night. My friend Ana wanted me to text him to confirm what time they were playing. I was reluctant because I don’t want to come off too desperate. To make it light, I sent a donut fact meme and asked if he had a donut waiting for me at the bar. He said I would have to come to find out, opening it up for me to confirm what time they were going on.

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While at dinner, my other friend that said maybe texted saying she was on her way. Then my gay husband called and asked if he could bring a friend. So now, even though I really only needed one wingman, I had an entire fucking entourage of five people coming to the show. I wasn’t sure how I felt about having so many people, but it was too late to tell any of them not to come.

The three of us that went to dinner showed up to the bar first. He was with his friends at a table, so the three of us grabbed some bar stools and ordered drinks. He came up and said hi baring a Stan’s Donuts bag just for me. I excitedly thanked him and introduced him to my friend and her boyfriend. We chatted a bit, then he got back to his friends.

His band was about to start, we made our way to the tables near the stage. I snacked on the donuts and watched as he got behind the drums. While his band was playing, my other friend, my gay husband, and his friend showed up and sat by me at the table. When Chase finished his set, his band packed up, he hung out with his friends for a bit, then came by us to see what we thought. I introduced him to the three newcomers. Now that there was six of us, the table was pretty full.

Chase stood next to me for a moment to chat, but I was now also entertaining five other people who were supposed to be wingmanning me, but somehow they failed to get the memo because they all wanted my attention. He excused himself and went to the nearby table where his band and friends were sitting. I gave my friend the ugh look, and she realized they cock blocked me. My girls and my friend’s boyfriend then decided to go to the bar next door temporarily to play skeeball. Now it was just my gay husband and his friend leaving the table a little more empty. A few minutes later, Chase came back to ask why my friend’s ditched me. I laughed, it was deja vu from the night we first met.

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The next band started. My friends came back, but my one friend and her boyfriend said their goodbyes pretty quick, leaving it with me, my gay husband, his friend, my other friend, and Chase. He offered to by me a drink so I told him my order and he went to the bar. When he got back, he sat next to me and we continued to flirt a bit and then the band asked everyone to get up and stand closer to the stage. We did so, and my girlfriend and I danced a bit to the music while Chase watched.

After the bands were done, my gay husband and his friend left pretty quick. My girlfriend hung out with me for a bit, but Chase lingered close by. He joined in on our conversation for a bit, then excused himself to go buy a band tee from the last band, but promised he would be right back. While he was gone, my friend asked if she should call her Uber, I told her to get on that because it was obvious Chase wanted to hang out with me.

She requested her ride. Chase came back, she then announced her ride was waiting out front. She said bye. Chase and I got talking. Then his friend interrupted to see what he was planning on doing. He hesitated and said he would catch up with them later. He then told me his friends wanted him to come out. I told him he could go, but then he said he would rather hang out with me. I said we could both go hang out with his friends. He revealed he lives in the suburbs, so that would mean going out there instead of staying in the city.

It was already 1am, so not worth going to an actual bar to have it close an hour later, so I then invited him to my place. I have a bar, so the drinks are free and the night could go as late as we wanted it with no restrictions. He agreed to come over.

We had both driven to the bar separately, so we both drove to my place in our own cars. He parked out front at the pay to park. I parked in the back and walked around to the front to meet up with him. We went up to my apartment, I gave him a tour, then took him to the bar and poured us each a drink. I sat behind the bar and he sat on one of the bar stools across from me.

Chase and I got talking, but not long into our conversation, one of my roommates drunkenly joined us. We entertained him for a good hour arguing about an upcoming party we were throwing for a friend. Chase played along and helped me with my argument. He was winning on every front; looks, charm, humor, and now defending me without even knowing me.

After the argument subsided, my roommate finally quit and went to bed. Chase and I were finally alone. It took all night to get my friends to give me space with Chase and then an hour of arguing with my drunk roommate before we actually had a moment to ourselves. It got quiet for a second. The sexual tension was so thick you could cut it with a knife. Chase then stood up and leaned over the bar to kiss me. We kissed for a moment, and then I pulled back and walked around to sit next to him, before I could sit down, he pulled me in and we began to make out. Another roommate walked in, I pulled back and laughed. I told him we should go to my room to avoid having any roommates getting scarred for life.

We got up and took it to my room. We fucked all night and then some. It was good, not great. I didn’t come, but I rarely do on the first night of sex. It was approaching 6am, I had to be up at 8am to shower and go to work. Even in the summer heat, he spooned me until my alarm went off. We woke up, he lingered as I said I had to jump in the shower and get to work. I then invited him into the shower, he joined me. We couldn’t stop touching each other and kissing the entire time. I was running late for work, I had to stop him from rubbing my body. We got out, both got dressed, and I walked him to the front door where we made out some more. I then went to gather my stuff and left out the back door to my car.

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I was exhausted, but staying up all night with Chase was well worth it. There’s more to tell you… I promise I will write again soon.

Yours Truly,
Kallie Pygus

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