The Rules of Dating My Best Friend's Sister(68)

After a moment, she said, “Yeah. I trust you.”

Yes.

“Thank you.”

There were no words to describe how turned on I was by what I was about to do to her. I tossed the condom aside, unable to fathom how freaking lucky I was. I reached into the front seat for a tube of lube I’d bought just in case.

“I came prepared. And no, I don’t carry lube around in my creepy van.” I chuckled. “I took a little trip to the drugstore this morning so I could be prepared for anything.”

She looked up at me, lying on her back, and smiled, awaiting my next move. I opened the lube and squirted some out before using my middle finger to explore her hole. I inched it inside her ass until it was all the way in.

“How does that feel?” I whispered.

“Good.”

“You want me to add another finger?”

She bit her bottom lip and murmured, “Yes.”

As I slowly inserted a second finger inside, I used my other hand to massage her clit. My fingers were all the way in now. She was still so tight, and I wasn’t entirely sure my dick was going to fit easily. There was only one way to find out.

“Do you feel ready for me?” I asked.

“I am.”

“Spread your legs wider. I want you to touch yourself while I fuck your beautiful ass.”

Lala began massaging her clit as I lowered my pants to my ankles. I took my rock-hard dick out and jerked it a few times, ready to come from the mere idea of what I was about to do.

“Tell me if I hurt you, okay? I’ll stop.”

“Okay,” she breathed.

I squirted lube into my palm and rubbed it over my shaft. Placing the head of my cock at her opening, I moved it around in slow, circular motions for a while until I finally made my first attempt to enter her. Inch by inch, I eased in, moving gradually deeper and deeper. It took several minutes before I was able to push halfway inside of her. I moved in slow, controlled movements, not only because I was afraid of hurting her, but because I was in danger of losing it at any moment.

“You’re so freaking tight…” I groaned. “Okay if I try to go deeper?”

She nodded through heavy breaths. “Yeah, it feels good.”

Lala bent her legs back farther and tilted her ass to allow me better access. Eventually, I was all the way in and moving freely.

“Nothing in my entire life has ever felt like this,” I muttered.

It was the damn truth.

“You can go faster…” she said.

I was trying to go easy here and she wanted more? I wasn’t sure I could handle it.

“When I come inside you, Lala, I want you to think about how you’re mine and only mine, sweetheart. You got it?”

“Mmm-hmm.” She tightened around me for a moment, nearly causing me to come.

Sliding in and out with ease now, I said, “You tell me when you’re ready.”

I continued fucking her slowly, my eyes alternating between rolling back in pleasure and watching myself enter and exit her, which was pretty much the hottest thing I’d ever had the pleasure of witnessing.

A few minutes later, she began to massage herself faster. “Come inside my ass, Holden. I’m ready.”

Her words totally undid me as I thrust deep inside her once, my balls slapping as I exploded, filling her with my hot cum and pumping in and out until there was nothing left. Holy shit. What just happened? That was phenomenal. After we both came down from it, I lowered my head to her chest.

Her body shook with laughter. “I’m almost afraid for you to pull out.”

“Don’t worry. I’ll clean you up nice and good before you have to go back.”

“Not sure there’s much you can do. I may have to use the work bathroom for like a half hour.” She laughed.

“Sorry, yeah.” I leaned to kiss her forehead. “I get that.”

“Don’t apologize. That felt amazing. Especially when you came.”

“Amazing doesn’t even properly describe what that felt like for me, beautiful.” I ran my thumb across her lips. “Thank you for trusting me.”

I slowly pulled out before lifting myself off her and reaching over to my bag to take out a towel I’d packed, knowing she might need it. I handed it to her. After she cleaned up—as best as one could in the back of a van—I looked at my phone.

“We still have like fifteen minutes before you have to be back. You said you ate, but do you want to get ice cream or something?”

“Anal and ice cream?” She broke out into hysterical laughter. “Why, you romantic man!”

“What can I say? I’m a romantic kind of guy.” I pinned her under me and tickled her. “That’s how we do it in the Creepy Lunchtime Van Express, baby.”

***

Lala came over to my place straight after work, and we had sex a few more times that evening.

That might have seemed like a lot, but if you took into account our prolonged weeks of foreplay, we were simply making up for lost time.

It was after 9 PM before we finally rolled out of my bed and went to the kitchen so I could figure out what to make us to eat.

Lala leaned against my counter as I perused the fridge.

“So, you knocked three items off my list today,” she said.

“Let me see…analingus, anal, and sex in a car, right?”