Blowjob Confession (Chicago #15)

"Fuck, I'm cumming!" he grunted, gripping a fistful of my hair once again and holding my head back a bit, looking into my eyes as he kept thrusting, his cock pulsing spurts of hot cum inside me.

My face gradually relaxed into a smile as I held eye contact with Mark while he came inside me. I liked that he wanted that, to feel even more connected as we came together.

He leaned down to kiss me again, moaning against my lips and causing me to clench on his cock again as it continued to twitch inside me, our bodies still wrapped around one another.

"That was fun," I said, smiling as we pulled back a few moments later, kind of jokingly making light of the intense experience.

Mark chuckled. "It was pretty fun."

Neither of us was in a rush to get up. Mark shifted to his side, laying against the back of the couch, his top leg still draped over and between mine as we kept talking and touching. It felt exciting to have so much time after. We talked about that too, and how it hadn't really ever happened before. Normally, if we were on the phone, we would go to bed soon after we finished cumming together. And all the times we'd been together to have sex so far, Mark had to rush off pretty much right away to get home or to work.

"Maybe we can plan a time to go away somewhere together soon," Mark suggested. "I could pretend to have a business trip."

"I like that idea," I smiled. "Maybe when my summer break starts."

"Yeah, that should work," Mark smiled back, pinching and teasing my nipple, lightly.

I squirmed a little under him. "I guess we can think of tonight as a trial run. See how many times we each cum with an entire night, and then try to beat it on the business trip."

"Maybe I should pack some viagra," Mark joked.

I laughed, still squirming as I got worked up again with anticipation. "Where do you think you'd want to go?"

"My company has an office in Milwaukee, so that might be a safe bet."

"That works, I guess."

"Not the most exciting, but I guess it doesn't matter, as long as there's a nice hotel, and maybe a couple of fun places to go out to if we ever feel like leaving the room."

"We'll have to see," I grinned, reaching down to rub my pussy a little as my clit tingled, pressing two fingers between my lips until they were coated with fresh wetness. "Might not be necessary."

"Mmm," Mark moaned, watching me touch. His hand slid up my thigh, pulling my legs apart further. "Maybe we could venture out to a sex shop at least."

"Oh, yeah?" I asked, smirking. "What would we buy?"

"I think you already have a bigger dildo on your list, since your current one is smaller than Chris."

"Yeah," I agreed, flushing and tingling a little more as I thought about it, squirming and pressing my fingers into my pussy a little deeper.

"I want to fuck you with it."

"Mmm," I moaned. "I want you to. Pushing it so deep into me. Or maybe even wearing it as a strap-on." The idea popped out before I'd even considered whether I should've screened that thought. I hoped Mark wouldn't be upset by the suggestion.

He seemed to think it over, like he hadn't considered that option before. "So I could fuck you with a bigger cock," he said, his voice coming out neutral, not giving me any sign of how he felt about the idea.

"Only if you want to do it like that," I said, trying to backtrack a little. "It would be fun just to feel you sliding it into me, too."

"Switching back and forth between fucking you with my cock and the dildo, so you could really feel the size difference."

"Yeah," I agreed softly, trying not to give away my excitement. I felt more wetness on my fingers as my pussy throbbed.

Mark seemed to sense it, reaching down to rub his fingertips along my slit, too, pressing two of his fingers into me to join mine.

"Fuck!" I groaned with the sudden intrusion, my pussy stretching to accommodate the extra fingers. I started to pull mine out, wanting him to take over, but he stopped me.

"Don't," Mark said, suddenly stern. "Leave them in."

I followed directions as always, breathing harder as he continued rubbing and thrusting his fingers into me again.

"I could also fuck you with both at the same time," Mark continued. "The dildo in your pussy while I fuck your ass. So you could imagine Chris and I filling you at the same time."

I moaned and started writhing beside him, my head rolling back as his fingers picked up tempo, his thumb rolling in circles over my clit. Then he pulled his fingers out suddenly, leaving just mine inside. I started to object, but Mark didn't give me the opportunity.

"Keep fingering yourself," he commanded.

Then, before I had a chance to beg him to touch me again too, I felt a wet finger sliding down further, rubbing between my cheeks and then pressing into my asshole.

"Oh, fuck!" I moaned, grinding my hips and pressing back on his finger.

"You want that, don't you?" Mark asked, unnecessarily.

"Yess! I want to feel both of your cocks inside of me at once," I moaned, writhing and fingering myself harder, faster.

"Such a needy slut," he teased, pressing in with his finger until I felt it breach my ass.

"Oh, my god!" I reached for his arm, pushing on it, trying to get him to give me more of his finger.

"Tell me what you want," he said. It felt like taunting as I writhed and moaned beneath him desperately.

"I want more of your finger. Please!" I begged, shamelessly.

"Like this?" he asked, pushing it in just slightly further.

"More!" I pleaded, moving my fingers to my clit and rubbing fast, the wetness of my juicy pussy audible as I touched myself.

Mark groaned, leaning down to take one of my nipples between his lips, licking and sucking. He gave me more of what I was begging for, pushing his finger in and out slowly, sliding it deeper with each thrust. "Such a hot slut."

"Oh god!" I felt close again, rubbing faster and faster, focusing on the feeling of Mark's finger fucking my ass faster and deeper.

"Are you imagining my cock inside your ass like this? Both of your holes filled."

"Yes, I want that so much!" I whined. "I'm gonna cum."

"Do it. Cum with my finger in your ass. I want to feel how tight it gets while your pussy clenches."

I kept moaning and writhing, rubbing my clit fast, pushing back on Mark's finger as much as I could, and imagining him and Chris both fucking me at once like that. The fantasy of double penetration wasn't new to me. I'd masturbated while watching porn videos on the topic plenty of times before. But this felt different. It was more intense and exciting knowing that it might actually be something that Mark and I could try together, with Chris or some other guy.

Before long, I was yelling out and cumming once again, my pussy clenching and my ass squeezing around Mark's finger.

He pulled it out slowly as I came down, moaning. "That was so hot. I love watching you make yourself cum like that."

"Mmm," I smiled, resting back and closing my eyes, luxuriating in the post-orgasm feeling. "That felt great."

"Maybe we should go out dildo shopping tonight," Mark suggested then.

I opened my eyes, looking up at him to gauge whether he was serious. "Really?"

Mark shrugged. "Maybe. I don't think you want to wait until summer break, do you?"

I laughed. "Not really."

"We could look up a place kind of out of the way, so it would be less risky going in together," he suggested.

"Yeah, that could work. And we could walk in separately, so it's not obvious we're together anyway," I added.

"Yeah," Mark agreed. "You can pick one out, and I'll approve it."

I smiled up at him. "Okay."

"Someone's excited," Mark teased, flicking gently at my still-hard nipples.

"I think two someones are excited," I joked back, reaching down to tap his hard cock.

"Maybe," he conceded. "I think the trip out will give me a nice little break, too."

"Doesn't seem like you need it," I observed, wrapping my hand around him, stroking gently.

Mark groaned, but pushed my hand away gently, shifting back on top of me briefly before standing and offering a hand to help me up. "Might need to take a break to ice it at some point."

We kept joking around and teasing each other as we got dressed and ready to head out. Every moment felt fun and exciting, having all of this extra time with Mark to myself. The warning voice was still there in my head, telling me I needed to be careful; I was letting myself get in too deep. But after everything Mark and I talked and opened up about that evening, it felt easier than ever to ignore that voice and enjoy whatever time we had together.