Letting Go

Shortly after I bought my njoy butt plug (See Baby Steps to Build Trust), I got The Perfect Triangle… piercing which was not so perfect. I had 8-10 weeks to heal. That meant 8-10 weeks of no oral sex, and being extra cautious of my new piercing. During this time, Neighbor Boy insisted on using the plug regularly. If I was blowing him, he’d tell me to “Grab the plug.” If we were fucking, “Grab the plug.” If I we were taking out my vibes, “Grab the plug.” If we were sexting, he’d tell me to get out my favorite vibe and “Grab the plug.” He didn’t quite push for anal, but he was eager to get me into the sensation and the idea of anal.

Almost 8 weeks of this and it was working. I was really getting into the plug so much so that I started using it on my own time as well. Sometimes, I would get wet and worked up just thinking about it. I craved the full feeling the weighted plug gave me. As 8 weeks came to a wrap, I started to bring up anal to Neighbor Boy, telling him we should try it when my piercing is healed.

There was only a short window of time anal was going to happen. I wanted my triangle to be healed, but shortly after my triangle was healed, I was getting my VCH repierced. Having oral sex on the table pre-anal was important to me. I wanted to make sure I was fully satisfied and at ease before letting him penetrate my ass.

It was late November. We were messaging as per usual, probably even sexting some, almost like our foreplay before we were supposed to hang out that evening. I brought up that we should try anal that night. He was excited, but told me he expects me to have my plug in and vibe going before he got there so I was extra worked up already.

Although I was excited, I was also anxious about the situation and him telling me to get myself ready before he got there was a huge turn off and quite aggravating. Him telling me to start playing with myself before he comes to fuck me can usually be hot, but this time, because it was to prep for anal, it was more upsetting than a turn on.

I told him I wanted him to come eat me and crank up the foreplay and ease me into it. I explained to him I’ve had a bad experience with anal before (kind of alluding to what happened without directly saying I was raped by Roid Douche yet) and that him helping me be comfortable and relaxed beforehand would be very important.

Well… this conversation quickly went south. I was getting more and more anxious and upset and kept pushing what I wanted and he got frustrated and said that “It’s starting to sound like work and I’m not really feeling it for tonight anymore.” Which of course pushed me over the edge and the night was canceled, at least for the moment.

Because of this, I met up with my gay hubby. We went and got coffee and I vented. The more I vented, the more I realized how stupid the argument was. Yes, he was being an asshole, but my anxiety and frustration wasn’t fully explained to him. I was basically freaking out and he (unaware of what actually happened to me) was responding poorly to my unexplained pushiness.

It was an unseasonably warm November day for Chicago. Although anal was off the table, I texted him to say we should take advantage of the nice weather and fuck on the roof because it was probably our last opportunity before Spring. We put our anal argument on pause to talk more about it later and agreed to finally have the roof sex we’ve been talking about since day one.

When he came up, I grabbed a condom and we went straight up to the roof. I locked the roof door behind us, a cautionary measure taken to buy us a little time if someone tried to come up. After some brief making out, he told me to turn around, lift my dress, drop my panties, and bend over on the edge of the roof. I complied. He kissed my inner thighs and made his way to my pussy with his tongue, teasing me, getting me worked up, just barely tasting me.

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Right when I thought he’d lick my clit, he stood up, dropped his pants, and put the condom on. He started out slowly inserting his dick little by little, making me want to push my hips back into his. With every thrust he went a little deeper and a little quicker until he was fucking me at that perfect pace. As he fucked me, I looked over the ledge, my heart racing, partially because a slight fear of heights, partially because the adrenaline rushing thinking about how anyone could look up from the street and see me bent over the ledge.

After a few minutes of this rush, he pulled out, laid on the roof and told me to ride him. I listened, straddled him, and rode his cock. He finished, I didn’t. I kissed him softly, then stood up and put my panties back on. He took the condom off and put on his pants. As we walked back inside and headed down the back stairs, he tied up the condom, and shoved it in a pocket of the drooping ceiling. I didn’t realize this until we got back to my room and he told me.

Once back in my room, after he divulged the condom ceiling information and I scolded him, I told him a little more about Roid Douche, I didn’t go into detail, but gave him enough to help him understand why I was upset about our earlier anal discussion. He told me he understood and wants me to be comfortable and wants to make sure it’s something I enjoy.

I want to trust him. I want to be able to get over this fear I have. I want to let go of the past. I want to move on.

Yours Truly,
Kallie Pygus

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