Proceeding with Caution

The morning after my encounter with Drunk Neighbor Boy, I woke up early to drive up to the campsite to meet up with my family. Shortly after I got there, he messaged me to apologize for his drunkness and to thank me for coming to his birthday party. Our banter was on point. He asked if he made an ass of himself, I poked fun at all of his ramblings of me being attractive.

It didn’t take too long for him to ask me out. I agreed. He then tried to see if we could hang out that day. I told him I was out of town for the next few days and would be back Tuesday. Without even asking, he then declared that Wednesday we would hang out. Lucky for him I was free.

Wednesday rolled around. No word from him since the morning after his party when I agreed to hang out with him. Now it was getting close to 6:30pm and I haven’t heard from him. I should have just canceled on him, made him think twice before being inconsiderate and not confirming or actually coming up a plan. Alas, I was intrigued by the fact that he lived downstairs and those possibilities, so I messaged him:

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His mention of telling me to wear shorts or tight jeans was a red flag. Who the fuck thinks it’s ok to tell a woman what to wear like that? I still give him shit to this day about it and he still tries to say it was a joke. In spite of his jeans comment, I wore a dress, and not a dress that was revealing. It was just above knee length, t-dress with a high neck line so absolutely no cleavage.

Anyways, after all this, I was starving, he was dragging ass, it was about 9pm by the time he was finally ready. My friend was still chilling, but she was about to head out, I told him to meet me out front in five because I was walking my friend to her car. He agreed. After walking her to her car and then walking back to the front door, I waited. He wasn’t there. I messaged him to hurry his ass up. A few minutes later he finally got his shit together and came out. I instantly gave him shit for his behavior, he apologized but insisted it was a joke.

We walked to DMK burger down the street. On our walk and during dinner we flirted, asked some basic questions to get to know each other, and discussed our expectations. I told him I wasn’t looking for a relationship, he agreed. We kind of hit it off now that we understood that we were both interested in casual sex, but I did tell him I would have to proceed with caution.

As we continued this conversation and walked back to our building, he asked more about what I mean with proceeding with caution. I explained to him that because he is my downstairs neighbor, obviously there are times we will run into each other with other people or if one of us catches feelings and the other doesn’t, things can get weird. He assured me that he would be totally fine and that if he saw me with some dude, he would smile at me and we would keep walking. He even threw in there that he would high five the dude or something which made me laugh.

We got back to our building, I invited him up to my floor for a drink. He accepted. We went directly to the bar and I made us each a whiskey ginger. We made our way up to the roof and kept chatting a bit more about our expectations. He explained his thought process, saying that it would be cool to have a fuck buddy that lives right upstairs. I agreed and it definitely felt like we were on the same page. We then started to discuss some of our sexual styles and kinks. We seemed to understand what the other wanted quite well.

He finished his drink and set it down. I took the last sip of mine, and that is when he went in to kiss me, drink cup still in my hand, I felt around to set my cup down, then wrapped my arms around him and kissed him more. The kiss was hot, not quite my style, but still enticing. He rubbed his hands down my back to my ass to grab it. Obviously an ass guy. He then went to lift my dress. I stopped him.

I kept telling him I’m proceeding with caution and I still can’t be sure if him being downstairs is too close to home. He kept insisting that it would work out just fine. I then joked and said, “You might not be any good.”

He laughed and then proceeded to tell me, “You might not be any good,” and then added, “I can show you and then you can show me your skills.”

I laughed, “Hmmmm, maybe…”

Neighbor boy pushed, “Let me eat you, even just for 60 seconds, to give you a taste of what I can do.”

I laughed, “Tempting. But I’m still being cautious.”

He persisted, “Just 60 seconds so I can show you and then you can show me.”

I bit my lip, thinking about how hot it would be, but also hesitant still, “I have yet to have oral or fuck on the roof…”

“So bend over and let me eat you.” He pressed.

“Fine.” I agreed, slid off my underwear, and looked at him, wanting him to give me direction.

“Turn around and bend over.” He asserted.

I listened and bent over, hands on the ledge. He came up behind me, kissed my neck, and bent me over further, my body now pressed on the ledge, he worked his way down and lifted my dress and ate me from behind for a few minutes. Something about being on the roof looking down at the sidewalk was both frightening and a huge turn on. At any moment, someone from the building could try to come up to smoke or someone could see us from across the street. I was getting into more than expected and his oral skills almost met the hype he gave himself.

He stopped, I turned around and kissed him and unzipped him as we made out, grabbing and teasing his dick. Once I got him all worked up, I worked my way down to kneel to blow him. I took him in and out of my mouth, looking up at him enjoying every bit of it. After a minute or two, I pulled away and stood back up.

“Why are you stopping?” He asked.

“You gave me some, and I gave you your 60 seconds and then some, now I’m done.” I explained.

“Don’t stop, let me eat you some more…”

“Ok, but not over the ledge.” I agreed, as much as it was hot, I also have a minor fear of heights.

He took off his shirt and laid it down on the surface of the roof  a bit further back from the front and told me to lay down. He began to eat me for a brief moment, then asked about 69. I agreed. He laid down, I kissed him, then worked my way down towards his cock and straddled his face. This lasted several minutes. It was hot, I was enjoying it, but I also knew at that moment there was no way I would cum from it. I was excited about the possibilities with Neighbor Boy, but wasn’t in a rush to test him out fully that night. I unmounted his face and continued to blow him a few minutes longer then stopped. I worked my way back up to his lips, gave him a kiss, and then stood up to grab my underwear from the front of the roof.

“Really?” He asked.

“I’m not gonna cum like this, I’ll probably go in and grab my vibe…”

“I like watching.” He tried.

I laughed, “There will be plenty more chances for that, but right now, I’m good. You gave me some and you got some.”

He pulled up his pants, zipped up, and put his shirt back on. We made our way back to my apartment. I walked him to the door, kissed him goodbye and went to my room to take my vibe out.

I wasn’t sure what to expect going into tonight, but I am glad he and I were upfront and discussed our expectations right away. This type of arrangements rarely work, even if the two people don’t live in the same building. I still wasn’t sure if it could work, but I was excited to see where things went. The next day he messaged me:

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The endless conversations we’ve had via messenger since this evening have been very open and honest. We’ve both inquired about our experiences, our likes and dislikes, inform if/when we’re sleeping with other people, and have discussions to make sure the other is satisfied with our sex. This is definitely different than most fuck buddies I’ve had, but I like it. It helps inform our sex and shapes our expectations of one another. It’s been good and proves how important communication is especially when sex is involved. More on communication and it’s imporatance another time.

Yours Truly,
Kallie Pygus

Drunk Neighbor Boy

A week later, while on my way to my family camping trip, I got a call from work asking if I could bartend. They knew I was on vacation, but the girl that was covering for me ended up in a car accident and would not be able to cover my shift anymore. I reluctantly agreed and said I would be running late as I was already almost to the campsite and would have to drop my brother off at the campground and then take his car to get back to the city.

While still on our way to the campsite, Neighbor Boy messaged me on Facebook. He was following up about the key for the roof. I told him I wasn’t home at the moment, but would be home super late and he could message one of my other roommates for the key to the roof. He flirted for a bit and said that if I hear a bunch of music and noise coming from his apartment when I get home tonight, I should stop by for his birthday party. I told him I would try, but it wouldn’t be until about 3am. He said the party should still be going, but I could also message him to double check whenever I get home. He also tried to tell me he wanted to get my number last week, but didn’t want to ruin my date. I told him that Shane and I are just friends and it wasn’t a date. He didn’t believe me.

I dropped my brother off at the campsite and turned back to go bartend for the evening. My manager thanked me for being there and said that if I wanted, I could leave as early as 12/12:30 as long as it’s not crazy. I took advantage of this offer, closed my POS, and booked it at about 12:20am.

I messaged Neighbor Boy as I was leaving and told him I would be there in about 20 minutes. He didn’t respond. When I got home, as I walked up to my apartment, I heard music coming from Neighbor Boy’s apartment. I wanted to freshen up and grab myself a drink to bring down, so I went up, I stalled in hopes that he would respond before I just showed up.

Fifteen minutes or so went by since I’ve been home, about forty minutes since I messaged him and still no response. In his earlier message, he did say if I heard a bunch of noise and music to stop by. I grabbed my drink, and walked downstairs and walked into the party. As I walked in, there was hardly anyone left. Like less than 10 people. I didn’t see Neighbor Boy in the vast open space, but I also didn’t look for him. I started to say hi to one of Neighbor Boy’s roommates, and not long after I got talking, Neighbor Boy sat up, he was laying on the couch nearly passed out.

He hurried over to talk to me and although I already introduced myself to his roommate Max, Neighbor Boy intervened to introduce us (kind of), but more or less to tell Max that, “This is our sexy upstairs neighbor that I’ve been telling you about,” as he looked me up and down basically staring at my tits.

Kind of offended, also embarrassed, yet some how flattered, I shut him down by saying, “Thanks for the introduction, but I think I got it covered, we already met.” And I continued my conversation with Max. Neighbor Boy drunkenly flustered now, tried to participate in the conversation. I still wasn’t accepting his drunk ass. Max offered to grab me a drink, I finished mine and accepted.

While Max went to the kitchen, Neighbor Boy stepped back in and apologized for his drunkness. He claimed he was napping and trying to sober up before I came, but I got there earlier than he expected. I listened to his drunkness, laughed as he frantically tried to explain to me his approach, and laughed some more as he drunkenly tried to make up for it by telling me things like, “You’re so attractive. Obviously I think you’re attractive. But you’re also cool. You’re sexy….” His drunken statements kept spewing out in a repetitive manner.

I tried to hang out for a bit, when Max came back with my drink, he stood near by to observe the drunken mess in front of us. Neighbor Boy was sloshed, trying to come back, but failing hard. His favorite thing to tell me over and over, “You’re so attractive.” He was trying so hard not to say hot, sexy, or anything that would offend me because he already fucked up. He also brought up my “date” with Shane a few more times, trying to tell me how he didn’t want to ruin it. About twenty minutes of this went by, I finished the drink Max made me, and then said my good byes. Neighbor Boy, upset and confused, followed me to the front door, “Sorry I’m fucked up. You’re so attractive. Can I take you out?” Slurring his words.

Now standing by the front door, I laughed and told him, “Try asking me again when you’re sober.”

“I’m sober enough. I think you’re attractive. Also cool…” he persisted.

“You hardly even know me.” I explained.

“You brought my dog back, so you’re cool.” He was trying so hard. I laughed, he continued, “So can we hang out?”

“You’re drunk. Try another time, and maybe,” I told him.

“Is that maybe a yes? Or are you just being nice?” and before I could tell him to ask me later again, his drunk ass continued, “Do you even find me attractive? I find you attractive.”

“Yes, I find you attractive.”

“Do you really? Or are you just saying that?” He questioned.

“I do.”

“So we can hang out?” He tried again.

“Ask again when you’re sober.” I insisted, and he conceded.

“Fine. But can I get a birthday kiss?” He was pushing it.

“A birthday hug.” I told him.

“A kiss?” He said.

“A kiss on the cheek.” I negotiated.

“Fine.” he accepted.

He hugged me and held me for a moment. He then leaned back still holding me. I looked at him, he pointed to his cheek. I smirked and went to kiss his cheek, he tried to turn his lips towards mine to try to kiss me. I pulled away and gave him a look, he then turned his cheek to me again, and I kissed his cheek. He pulled me in to extend the hug for a moment, then I pulled away and walked out and headed up stairs to pass out.

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Is downstairs too close to home? Am I shitting where I eat? When the boy in question lives right downstairs, it’s important to proceed with caution. We’ll see.

Yours Truly,
Kallie Pygus

When Two Boys Meet

Fast forward about a month to early August….

I haven’t seen Neighbor Boy at all since I met him a month earlier, which was kind of disappointing, but then again we didn’t exchange numbers or anything. During this time, I went on several tinder dates, saw Chase a time or two, and have been hanging out with Shane more and more platonically. I had so much going on with other boys that Neighbor Boy was the last guy on my mind.

There’s always extra bartending gigs in the summer with festivals, so Shane and I got to work together for a friend’s booth at Taste of Lincoln. Throughout the day, we were mildly flirty, but more friendly and comfortable with each other than anything else. We bonded over both being bartenders; however, during this same gig, he told me he started applying for full-time jobs again and even had an interview, so would be quitting bartending soon.

Although I still find him very attractive, it seems like Shane and I got to a point where we’re friends. Or so I thought… He was very confusing throughout the day. Like he kept giving me this look like he wanted me. A few hours into the day, it slowed down and I sat for a moment and got my sunblock out to reapply. As I went to put some on my shoulders, he walked up behind me and began to rub them for me and spread it down my upper back. Shane is the best with his hands, his massages are to die for, so I relaxed and tilted my head down to let him continue to rub my back. Some people walked up to the booth, Shane stopped massaging me to take their order. I quickly finished adding my sunblock and went back to the front of the booth.

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Our light banter continued, but it was still hard to read. I want to be able to be friends with him, and I think we were doing well for a while minus the times we ended up fucking (even then we easily continued being friends). On the other hand, I really want to fuck him. I miss kissing him, holding him, having him massage me, and I miss feeling his body against mine as he fucks me. He is still one of the greatest lays and I know we couldn’t ever be in a relationship with each other, but I wish we could continue to fuck.

As our evening wrapped up, Shane and I cleaned up our booth, closed up, and headed out. We both walked towards the redline and he asked if I wanted to grab a drink with him. I told him there was a party going on at my place, but that he should come by and we could have a few drinks there. He accepted the invitation and we hopped on the next redline to my place.

When we got to my place, the party was packed, we squeezed our way to the bar and I grabbed Shane a beer and made myself a whiskey coke. There was a band playing that night, so it was pretty loud. My roommates needed some help with the party, so I was running around picking things up and grabbing some friends some drinks. During this, Shane and I kept making eye contact. I pulled one of my other roommates aside to tell him to pick up my slack and let me chill with Shane. He agreed and I got back to entertaining my guest.

I sat at the bar next to Shane. He told me how sweet the party is; it was his first time at one of our parties. I laughed and tried to keep it platonic, but I kept thinking about how I wanted him. The band ended, I went back behind the bar and grabbed Shane and I each another round. As the next band started, I took Shane up to the roof, hoping to find a quieter space.

When we got to the roof, there were about twenty or so people up there, but definitely a bit more quiet and tame compared to inside. I lifted myself and sat on the ledge on the front of the roof, he sat right next to me. He was closer than I had expected, but it was a pleasant surprised. His leg against mine, we started with some bar talk, ranting about various customers and telling tales and horrors of our bartending experiences. This quickly changed to a more flirtatious banter and got to a point where there was a comfortable silence. We locked eyes for a moment in our silence, but at this very instance, Neighbor Boy and his roommate Mike walked up.

I stood up and gave Mike a hug and said hi, then looked and Neighbor Boy and said hey to him as well. I introduced them to Shane and we all got talking. It was Neighbor Boy’s first time on the roof. He asked me how to get a key for the roof because they were having a party next weekend. This was getting complicated, I wanted Shane, but couldn’t resist my flirtation with Neighbor Boy. I’m terrible at hiding it. To be a little sly, instead of flirtatiously giving Neighbor Boy my number, I told Neighbor Boy that Mike has my information or to find me on Facebook and I could get him a key. At that moment, Neighbor Boy got a bit weird, said thanks but then said bye right away and left.

Mike stayed up and chatted with Shane and I a bit more. He told me that next weekend is Neighbor Boy’s birthday party and I should come. I told Mike I have a camping trip planned with my family, but if for whatever reason I’m around, I would stop by. The conversation wrapped up and Mike went to talk to another one of my roommates that was on the other side of the roof.

Shane and I sat back where we were at, but now he was a good foot or two away from me. He took a sip of his drink, I took a sip of mine. At this point, he said he should finish his drink and head out. A little disappointed, I jokingly asked, “Why? Is it past your bedtime?” He laughed, but then told me he was going to meet up with some friends. I let it go. He finished his drink, we hugged, and said our goodbyes.

That was the last time I saw Shane. He got the job he interviewed for, so he quit bartending. As a result, we texted less and less. He no longer had bartending stories or customers to bitch about. We no longer had common ground. He is back to being a soccer playing corporate employee with a 9-5, while I’m still a free-spirited artist and curator that works odd and end jobs. Every rare occasion we will text one another, but usually it’s just a one-off meme or quick text. Nothing more.

Although this boy was no more, you know what they say; when one door closes another opens.

Yours Truly,
Kallie Pygus

Neighbor Boy…

What happens when there’s a new hot downstairs neighbor? Well, you flirt a little here and there and then one night, he drunkenly tells you he thinks you’re sexy and wants to take you out. Then what? I will fill you in on all the dirty details, but let’s back up to when it all started.

Neighbor Boy moved in the floor below me early this summer. I actually never met him though until July. It took his roommate’s dog escaping and wandering up into my apartment. Someone walked into my place during a party, and left the door open, the dog followed shortly after. As the dog walked by me, I grabbed his collar, and made my way downstairs. I recognized that the dog belonged to Neighbor Boy’s apartment because I’ve seen Mike from their apartment walking him before.

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When I got downstairs, the door was wide open. I walked the dog in and saw several guys I didn’t recognize chilling in the living room, so I asked, “Is Mike or anyone that lives here around?”

Neighbor Boy quickly jumped up and introduced himself, “I live here.”

“Ok, well your dog came up to my place just now, I’m returning him.”

Neighbor Boy thanked me. He then walked me to the door and we continued to flirt in the doorway a bit. After a couple minutes of chatting, I told him that him and his friends should come by the party for a bit. He accepted and said he would round up everyone and be up shortly.

I went back upstairs and told my friend Jackie about the new neighbor and how he is pretty much my type; handsome, fit, funny, not a total prick… what more could a girl want? When Neighbor Boy and his friends came up, Neighbor Boy came in and we flirted some, but I played it cool and told him to check out the bar and grab a drink.

At some point, one of Neighbor Boy’s friends came back to talk to Jackie and I. He kept telling us about Neighbor Boy, but in the most suburban white boy type of way by saying, “He’s cool. Have you ever had a black neighbor? He is the cool black neighbor but isn’t bad black if you know what I mean.”

Jackie and I were absolutely speechless. He then continued drunkenly, “I bet you don’t even have any black friends.”

We were appalled. That is when we shut him up and told him that this is Chicago, we know a lot more black people than he does (obviously) being that we went to school with, dated, are friends with, and work with numerous black people and that he should shut the fuck up while he’s ahead (not really ahead).

During this discussion, Neighbor Boy caught this happening and came up to apologize for his friend. As he apologized, I intervened his apology and said, “Don’t be sorry, if anything, I’m sorry for you. He’s kind of an asshole.”

Neighbor Boy laughed at this and agreed, “Yea, it really seems to come out when he’s drunk. I’ll get him out of your hair.” Soon enough, Neighbor Boy and his friends made their way back downstairs to be safely drunk away from the party.

That was the first time I met him and I could tell already that we could have some major chemistry, but being that he lives down stairs, I would have to proceed with caution.

More soon.

Yours Truly,
Kallie Pygus