By the Weak

10

Why would anal be a better idea than vanilla sex? Good question.

The entirety of our relationship was a big ole mess. Here I was saying 'no' to sex, but yes to a relationship and anal? His mom is my neighbor, and I will have to look at the woman after her son puts his cock in my ass. I genuinely need to rethink my life choices.

"Get on your back," Joel said with a slap to my ass cheek.

"My back? I think you are doing it wrong..."

"You can have anal in a missionary position. That's what I want. Got a problem with that, babe?"

"Oh, uh, no," I said as I crawled into the middle of the bed and laid down on my back. "Are you sure about this? I mean..."

"Look at this," Joel said as he unfastened his jeans. He fished out his erect cock and stood there with it wrapped in his fist. Somehow it looked even more menacing, captured in a firm hand as though it was a snake that required a handler to keep it tame. "Do I look unsure?"

"Uh, no. Definitely not unsure. Uh, lube?"

"Ah! Hold a sec!" Joel said as he strode to the bathroom. When he returned, he held a small bottle of KY. "For your pleasure."

"How did you?"

"I basically unpacked this place. Plus, I needed some once when you weren't here. Ya know, a bit of self..."

"Got it!"

I watched as Joel opened the snap top and poured a bit of lube into his hand. He began a slow tease of his heavy cock as he watched me. My legs automatically fell open for his gaze. "Touch yourself," he said as my pussy became exposed.

I did as he asked and placed my fingers between my legs. I circled my clit as I teased myself. It was a game I often played when I masturbated - being so close but not touching my center of need.

Joel crawled up the mattress and rubbed his lube-coated fingers through my center and down to my ass. He circled the puckered hole as he did earlier, and I moaned, moving my finger closer to its target. Then he pushed the lubricated finger inside, and I clenched my pussy on air.

"Fuck," I said on a long exhale. "That feels so good, Joel."

"Yeah? Want more?"

"Mmhm," I agreed as I felt him remove his finger to add a second. He used the two digits to fuck me as he kneeled between my knees and watched not only his penetration but my masturbation.

"Three?" He asked.

"Yes," I groaned as he pulled out again. "Three."

Joel added the third finger and started to stretch my virgin hole. He scissored the fingers and added more lube. It felt like an eternity before I began begging for his cock.

"Joel, I want you to... I need you," I whined. Since he was as excited as I was, he quickly withdrew and relubricated his cock. I continued to rub my clit as I watched him manhandle his hard dick.

Joel placed one hand by my head to support himself as he leaned over my excited frame. "I hear it hurts an awful lot the first time, but just talk to me, okay?"

"Mmhm," I hummed, not being a stranger to anal play.

"Good girl," Joel said before kissing my forehead and then directing his cock head to my ass. "Relax."

Joel pushed forward slightly, then realized that for such a broad crown to enter my rear passage, he would need a bit more force. He pressed the head inside, ensuring he guided it with a firm grip. When it finally popped in, I groaned at the feeling. It was definitely uncomfortable, but Ryan would often use things much larger.