That wasn’t totally what he had in mind though. He had gotten up on the bed behind me, but he leaned to reach past me and grabbed the pillow to my left. He folded it and then pulled up on my hip. Going along with the pressure, I pulled my knees up under me until he stopped.
He slid the folded pillow underneath me. “There we go.”
Then he gave my cheek a light tap. I let my weight settle down. With the firm pillow folded underneath my hips, I didn’t end up lowering down more than a few inches. It was actually pretty comfortable, but I felt really exposed, not in a bad way though.
“Nice”. He clearly liked what he saw.
As soon as I settled into position on the pillow, with my ass fully exposed, his tongue went back to probing into my hole, penetrating even further due to the new, more accessible position.
His face pressed between my cheeks as he thrust his tongue into me. I was delighted. “Uhhh. Oooh.”
I didn’t really need to, but I reached back and pulled my cheeks apart to give him even better access. It didn’t help him get his face any closer, but it did serve to stretch my entrance a little wider for his tongue. He slowly made out with my ass, soon becoming more urgent and he started thrusting it in and out as much as he could, tongue fucking my ass with everything he had.
“Oh! Fuck yes!” I was loving every second, every thrust of his tongue amplifying the pleasure coursing through me.
He pulled his face and tongue away but, before I even had time to think, he replaced it with his finger, swirling around the outside, then gently pressing until I loosened up just enough for him to push the tip of it in. Once it was in, instead of working it forward, he continued working in circles. The pleasure of the intrusion and the pressure all around the inside of my ring was amazing, so amazing that I didn’t even think that there might have been another reason for what he was doing.
I felt him shifting around on the bed behind me as he started to move. He left his finger partially in me but stopped working it around as he shuffled to the side and leaned toward the nightstand. I had conveniently left a bottle on the nightstand, feeling like I might be needing it one way or another. I was happy that John had found it.
It seems cliche but once he returned to his position behind me, I heard a soft click followed shortly by a cool liquid slipping between my cheeks and down my crack. It wasn’t until it reached my pucker that John pulled his finger free, just long enough for him to slip it up and down my crack to coat it before pressing it back in.
He was gentle as he slowly pushed it in deeper, twisting it back and forth as he went, until finally I felt his knuckles pushed against my ass and the tip of his finger sent a shock through me as it pressed against that previously undiscovered button inside. He had to have seen the large amounts of precum dripping from my cock due to his probing. He pulled most of the way out before slowly driving back in to first press against, then massage my sensitive prostate.
I blurted out, “Yes!” and moaned while pushing back against him.
He thrusted more quickly in and out a couple of times, then he paused to squirt more lube down my crack before squeezing a second finger past my puckered ring. Once he got past the first bend in his fingers he stopped pressing forward and rotated them back and forth. The new pressure was mildly uncomfortable at first but as I relaxed into it the added stretch and friction started to feel amazing.
Again, he started forward while continuing with the twisting machine until he bottomed out with two fingers now pressed against my pleasure button. He didn’t pull back out immediately. Instead, he stroked the tips against it, causing even more thick precum to ooze from my cock. Each time he flexed inside of me I moaned and dripped.
The building pleasure continued with his two fingers curling, and twisting and thrusting continued but was soon cut short, too soon it seemed at the time. My disappointment was soon laid to rest when the familiar feeling of more lube was followed with the feeling of yet more pressure. The narrow tips of three fingers pressed in smoothly at the start, but as they crept forward the stretching increased quickly.
He took his time as he worked them in, keeping the dull ache at bay as he allowed me to get used to the new girth that each centimeter forward brought with it. I was quiet as he pushed, focusing on relaxing, all while enjoying the new pressure as my previously tiny ring stretched to new widths.
“Mmmm…”
“You like that? You’re squeezing my fingers so hard.”
“Oh yea.”
“And you’re oozing and making a big wet spot on the bed.”
“It’s…ung…your…oh…fault.” He finally bottomed out and kept interrupting me with short pokes at my prostate, sending ripples of pleasure deep into me.
He only pumped into me a few times with his three fingers before pausing, “My fault? Just wait.”
At that, he withdrew them completely. I heard him with the bottle again but there was no new stream down my crack. I was about to look behind when I felt something else slip between my cheeks, this time moving up instead of dripping down. That something was thick and both soft and hard at the same time.
I gasped and a jolt shot through me as I realized what it was. “Oh god.”
I reached back and held my cheeks open wide.
He pushed my hands away, held onto my hips, and continued grinding his hips and thrusting his rod up and down my crack. “What a sight, my cock slipping between your cheeks.”
“I’m ready.”
He pulled his cock out from my crack, and I readied myself, but he didn’t put his head to my entrance. Instead, he swatted it lightly first against one cheek, then the other. “Ready for this?”
“Mmhm. So ready.”
He poked the underside of my balls with it before dragging the fat, spongy tip up across my now slightly open hole, and up through my crack. He thrust up and down between my cheeks again, driving me wild in anticipation.
He placed his head against my pink ring and held it against me, then he pulled it away. “I don’t know. It looks like it might not fit.”
The next thing I felt was the three tips of his fingers again, rather than the single tip of his penis. He pushed them in and I realized that, even though he was intentionally teasing me, he was also partially right. I had tightened up again since he pulled his fingers out.
He continued forward with the steadily growing taper of his fingers until he bottomed out once again. He stopped short of his fingers pressing against my prostate, pulled them back and worked on stretching me but not quite like before. Rather than just twisting, he was working his hand in a circle, pushing out in different directions as he was, trying to loosen me more.
It was amazing but it wasn’t what I wanted anymore. “Fuck. I think you should check again.”
He pulled his fingers back out and then smacked his cock against my cheek again. “You think so?”
He slapped his cock against my other cheek. “You want this?”
“Yes.”
He dragged the tip down through my crack and then paused at my partially gaping entrance. He pushed lightly against me, the very tip squeezing in to close the hole, “You sure?”