Like a Virgin: All Oiled Up

Content Warning for language and descriptions that might be considered vulgar.

The first day I met my boyfriend at the time, he left me with the loveliest words: “Your ass is so fuckable.” I knew that it was eventually going to come one day, and no matter how many times I tried to practice having something shoved inside of me in the shower, I was still terrified at the thought of being penetrated. From talking to all my non-virgin friends, I learned that lots and lots of lube was key. Thankfully, having worked the Pride Festival in New York over the summer, I was well stocked up.

The day started when I received a text from him asking if I wanted to go to the mall and get first-day-of-school outfits. I made sure to shower in preparation for what we both assumed was going to happen afterwards. With my hygiene and our shopping out of the way, he told me that he wanted to take me to Buffalo Wild Wings since I had never been before. Long story short, I hated it, but I didn’t feel like complaining because I wanted to make our last days of summer vacation the best ones yet. He asked me if my parents were home, which they weren’t since Sunday was their usual casino day, so he asked if we could go back to my house. I nodded my head. In a sudden move, he grabbed my hand and grinded his crotch into it, showing me his erection. Of course, I knew what was going to happen next.

As he began driving back to my place, I teasingly put my head against his crotch. With him panting above me, I unzipped his fly and licked the fabric of his boxers. 

I felt the car jerk.

“Are you trying to make me crash the car right now?” he asked me with lust in his eyes. I simply told him that I thought I could make him finish before we even got back to my room. As I began giving him road head, he made me stop, saying that he was close and didn’t want to finish so soon. I clicked my seatbelt back in and abided, but still felt him up to be a tease.

The minute he parked, we literally ran into my house. Locking my bedroom door, we were on the bed in seconds, him on top kissing and nibbling every spot that he knew. It instantly put me in the mood. Suddenly, with the button on my jeans already undone, he ripped them off and they slapped the wall on the other side of the room. We spent a lot of time on foreplay for this occasion, with him prepping me in my nether region.

“Can I fuck you?” he asked me.

I told him that he couldn’t, but he could instead make love to me. He gushed at those words, but based on his next statement, the adorableness didn’t last long.

“This ass is mine,” he said, groping both cheeks.

As he broke open the condom and lube packets, I tried to relax myself. He slid one finger in, and I felt myself resist. Slowly I adjusted. Two, three fingers. I was ready to have my cherry popped.

I felt a bit of pain with the initial push, so I told him to start kissing me to drive my attention away from the stinging I was starting to feel. It felt like we were stuck in that missionary position for a good couple of minutes, and I started to feel nothing down there.

“Are you in all the way yet?” I asked.

He looked at me, looking a bit shocked and offended, and told me that he had been balls deep in me for a while.

“Oh, awkward,” I laughed.

With that, I was no longer an ass virgin and I was amazed at how great it felt. As we went from position to position, we were both lost in the pleasure that we were feeling. The first time he hit my g-spot, I even moaned out loud, which surprised both of us since I was generally pretty quiet.

“I’m close,” he told me.

He told me that he wanted me to blow him to finish, which I agreed to happily. He erupted in my mouth, and even though he tried to return the favor for me, I ended up having to jack myself off to cum. He simply watched me until I was ready.

“Was that supposed to hurt?” I asked him. He looked at me dumbfounded.

“I guess you aren’t as big as you thought you were,” I joked.

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