Thursday, December 8, 2016
I woke up to a voice message from The Australian; hearing his accent was a nice way to start my morning. He’s been consistent and true to his promise. So far we talked pretty much all day every day, we shared things about our childhood, our hopes, our dreams, and kept up with our flirtatious banter; we shared things that I usually avoid talking about with most guys. It’s only been a week and I was beginning to miss him, a guy I just met briefly for two nights hardly a week earlier… but alas, he was on the opposite side of the world in Australia for the next few months and there was no promise of coming back to Chicago permanently (or at least semi-permanently).
Mixed in with my snaps and Whatsapp messaging with The Australian, I got a message from Neighbor Boy, he asked for my review on his performance on Day 2 of my Birthday Sex Marathon. He did quite well, he teased me till I was begging, repeatedly brought me to the brink of orgasm multiple times, and once he finally got me to come, he pulled out and left me craving more. His game plan, as revealed the night before, was to do everything to keep me begging for more the next few days and it was working. He then asked what I wanted more of; I told him the obvious, more oral sex.
That evening, he told me when to take my toys out and demanded I start playing with myself as he would be up soon. I sent off my “Day 3 of my birthday marathon…” snap to The Australian and got my toys out. I started off slow, set my vibrator on the lowest setting and ran it down my body starting at my nipples, circling them gently, then down my torso working my way closer and closer to my vulva. As I approached my inner thighs, the temptation to give in was magnified.
My clit tingling, I finally caved and brought my vibrator to it, but only lightly, running it up and down my inner lips tickling my clit with every upward stroke. I was on the brink of coming when my bedroom door swung open; it was Neighbor Boy. Resisting my orgasm, I set my vibrator aside.
No words exchanged, he dove face first into my soaking wet pussy. I demanded more oral and he delivered. He brought me back to the brink of coming, then stopped. He looked at the toys and handed me the butt plug. I lubed it up and slowly inserted into my ass. He got back to work, licking my clit and playing with the plug. The sensation of the plug mixed with his tongue on my clit pushed me over the edge and my body gave in, my breathing got heavier, my back arched, my vagina contracted.
Neighbor Boy slowed down, and as the final contraction released, he looked me in the eyes, crawled up, and kissed me. “Better?”
“Yes,” I smiled.
We laid there for a second, then after I came down from my orgasmic high, I proclaimed, “Fuck me in the ass.”
He smiled, agreed while demanding, “Sure, but blow me first, get me hard.”
I crawled backwards down his torso kissing him down his chest and took his cock into my mouth and blew him. A few minutes in, he was worked up and ready, I got up and handed him a condom and lube. I laid next to him anxious. I was nervous yet excited for us to have anal sex. This was the first time I was fully eager and willing to let a guy enter my ass with his dick since ten years ago when I was raped by Roid Douche.
As he put on the condom and lubed up, he asked, “Do you want to be on top? Or bottom?”
“Bottom, missionary, it will help me relax more,” I explained as my anxiety was kicking in more. I then reminded him, “Take it slow, also, no promises we can finish.”
He nodded, “I know, I’ll take it easy on you, don’t worry.” He then squeezed some more lube on his finger and slid it into my ass.
We laid missionary, we kissed, with one hand I held my vibrator to my clit and with the other I guided his dick towards my ass. With a deep breath in and exhale, he slowly inserted his cock. I focussed my energy on kissing him, the stimulation on my clit and relaxing my ass. My heart pounded. A few minutes in of him slowly sliding in and out of my ass, we switched positions, doggy style now. He entered from behind slowly. As he slid in and out, he added some light spanking and hair pulling, something I’d usually allow, but I panicked. I stopped him, I rolled over and he laid beside me.
He asked, “Is everything ok?”
I started to tear up, “I’m fine. I was enjoying it, it’s not you…” I paused.
“Are you sure?” He asked.
I sat up and the tears flooded out turning into full on crying. He pulled me towards him, holding me, trying to soothe me as I had a breakdown. “I’m sorry,” I explained, “It’s just difficult for me. I’m enjoying it, but it’s also overwhelming.”
He made a smart ass remark, “Dick so good she cried,” but quickly realized that wasn’t going to work in this situation. He then took it down a notch, “What’s up?” And that’s when I fully unleashed the tale of Roid Douche to him. He kept trying to comfort me, yet the whole scenario was awkward as fuck. He tried to be sympathetic, it worked a little, but he kind of failed after the fact.
Once the crying subsided, he left to go back down to his room, leaving me alone vulnerable in my room. He then messaged me:
Really? “This gonna be all worked out for tomorrow or what”? What type of question is that after I have an emotional breakdown and spill everything about being raped? To top it off, he still pushed trying to get his dick wet and gave me a maybe for my official birthday sex. He was failing on his response and he wasn’t getting it.
Having anal sex was a big deal to me and I still don’t think Neighbor Boy fully understands this.