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.
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.