All In (Firsts and Forever 2)

“I don’t think about it much,” I said, pulling a pillow onto my lap and hugging it, “the fact that you and my best friend had sex like, a hundred times. I kind of can’t really give it much thought. Because if I do, it just sort of freaks me out.”

“For him, it was business. For me…well, this’ll sound awful, but he was just a way of getting off. I never loved him. We never had a relationship. We just fucked. And it all happened before I met you, Charlie.”

“I know. He told me you cancelled on him the night you met me.” I grinned a little at that. “Little did you know you wouldn’t be getting any for weeks after that.”

He grinned too. “From the first night I met you, I never wanted anyone else.”

I turned the blue toy over in my hand and was quiet for a while, mulling over my boyfriend’s and my best friend’s history. It was only weird if I let it be. The two of them were dealing with it, after all, managing to live cordially as roommates without letting the past cloud the present. I too could choose to just accept it and move on, like they had. Eventually I said, “I don’t get why this would be a favorite. It looks like any other plug.”

“I could show you what makes it special, if you like.”

I handed him the plug, and made a decision. I wasn’t going to let the past throw me off, and I wasn’t going to let Christopher’s involvement in packing this case freak me out. I was just going to enjoy my first sexual encounter with Dante in weeks, and not ruin it with misplaced jealousy and insecurity. I tossed the pillow I was holding aside and laid back and spread my legs, and said, “Ok. Show me.”

“Oh. In you?” Dante looked surprised.

“Yeah. I’m done being weird about it. Show me what it does. In fact, show me what everything in that case does. Use it all on me.”

He smiled at that, and said, “It’ll take me days to use all of that on you. But we can certainly start with this.”

He took a sealed package of lube from the case and said, “Ok, as I said earlier, this needs to be a collaborative effort. Please get a couple towels from the bathroom for me, Charlie.” I did as he asked and was back a moment later, my cock already starting to sit up and take notice. “Spread one towel out on the mattress and tear open this package. Then put a lot of lube on the index and middle finger of your left hand. Coat them thoroughly on all sides.”

“Oh God,” I gasped as I realized what was happening. My cock throbbed in response.

“Lay on your back, angel, and spread your legs wide. And then slowly and carefully work one finger into your little hole for me.”

There was something so fucking hot about being directed like that, about the quiet, confident way Dante was assuming control. I complied immediately with a murmured, “Yes sir.” I rocked back so my butt was in the air, knees on my chest, and reached around to my ass. He liked that, his lips parting slightly, his hand going to his cock, stroking it lightly through his clothes as I rubbed my tight little opening with a slick finger and then pushed it inside me.

I had never fingered myself before, and was surprised at just how tight I was. I couldn’t imagine how Dante’s big, thick cock would ever fit inside me. But now wasn’t the time for random musings, and I pushed deeper into myself. I guess I did it too fast because I gasped at a sudden jolt of discomfort, and Dante soothed me and coached me to go more slowly.

Eventually I took all of my finger inside me, the rest of my hand cupping my ass. I moaned quietly and rocked on my hand, fucking myself as Dante reached over and caressed my cock and balls. Embarrassingly, I made a sound that was not unlike a purr.

He rubbed his thumb over my leaking slit, and then took hold of the hand that I was using to finger myself. He couldn’t make a fist with the cast on, but he could grasp with his thumb and fingers, and he held my hand firmly as he instructed, “Work the second finger in, angel.”

“Yes sir.” I was way too aroused to be gentle with myself, and shoved the second finger inside me along with the first, biting my lip to stop myself from crying out. And then I got why Dante was holding onto me. He began to use my hand like a dildo, fucking my ass with my own fingers. “Oh God yes,” I whispered, rocking up off the mattress, grabbing a fistful of sheets with my free hand.