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:

nb1

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:

NB2.jpg

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

5 thoughts on “Proceeding with Caution

  1. Great story. You have an interesting attitude about sex. This guy must be extremely good looking – to have gotten anywhere with you despite saying things like, “wear some nice shorts or jeans to show off that ass,” or ” “Let me eat you, even just for 60 seconds, to give you a taste of what I can do.” Was he able to help you cum since then? What kind of toy do you use that is so effective?

    Great, brave, honest, interesting blog – following.

    Thank you

    Like

    1. He’s cute. Yes we’ve been fucking ever since and he’s learned very well how to make me cum. And I’ve got a whole drawer of toys, but my lelo vibes are my go to for a quick orgasm when I need it. Thanks for the follow. I’m really behind, but will be posting again soon.

      Liked by 1 person

      1. I’ve got 3 lelo vibes, they’re all wonderful. I couldn’t tell you the exact models off hand, but all three do the trick and I could only imagine that many other lelo vibes would do the same.

        Liked by 1 person

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