When he returned, he had a clear glass jar of Vaseline with a blue label printed right on the glass and a white tin screw on cap. “Okay. We will keep this in here from now on so we won’t have more interruptions in the future, if we should need it.” He opened the jar and set it aside. “I’m going to get you ready. You are pretty much there, but I want to make sure you are really open for me since this is your first time. Lift your legs for me again.”
I did as he requested and without warning he licked me again, but this time felt different. He did it with the purpose of preparing me, not for strict pleasure. After a couple of minutes of me softly whimpering, he popped his head up like a groundhog. “You, okay? I’m going to use my fingers now.”
“I’m okay, Jimmy. But I’m getting impatient.”
Jimmy chuckled, “Okay, it shouldn’t be much longer until you are completely full of me.” But he paused like a thought smacked him. “But Honey, if you want to stop at any time, we will stop. Even if I’m inside you, if you want to stop, it will be done.”
He leaned over me and kissed me again. He dipped an index finger in the jar of Vaseline, completely coating it. He moved the tip of his finger to my hole, smearing the jelly around the entire area.
Once I was coated well on the outside, he looked up for permission, which I gave. I felt his finger start to slide into me, the pressure completely different than his tongue, which had softness to it even when he stiffened it into a point.
I wiggled my butt a little from the uncomfortable feeling I was experiencing for the first time, not being able to not move. When I felt Jimmy’s hand hit myass, I knew he was completely in. Then he shot sparks through me when he rotated and moved the finger side to side. “Holy Fuck!” I arched my back off the bed.
Jimmy snickered. He pulled out to his top knuckle and slid back in, before he warned me he was going to add a second finger, repeating the process but this time with some pain. There was some resistance this time, like something was blocking the route he wanted to take and I think he could tell I was uncomfortable. “Honey,” he whispered, kissing the back of my thigh. “Slightly push for me.”
I did as Jimmy asked, and it was like nothing was in his way anymore, as his fingers slipped right in making me gasp in slight pain, but more out of surprise. Once he was completely inside me again, he stayed still. As he was letting me get used to it, the pain transitioned to comfort, me relaxing on his fingers while rubbing my body. He scissored my hole, stretching me out, before rotating and repeating.
I gasped, “Oh my God.” When I looked down to try to see what he was doing to make me feel the way I was, I noticed my dick had flagged, laying limp below my naval.
Probably noticing my panic and embarrassment, Jimmy took me in his free hand, and held me tight. “It’s okay. This is normal. Your body just reacted to the initial pain. You will eventually get used to it to the point it may not happen, yeah?”
He started to stroke me, my glands still sparking even though I had lost my hardness. The static shocks from the movement brought my cock back to life like Frankenstein's monster.
As he worked me, he pulled his two fingers out before adding a third, much slower because of the width of them together. I groaned the entire time in a mix of a sting of pain and rolling pleasure, the widthof his fingers hitting something within me, making me leave my body.
He removed his fingers once he seated his hand against my ass. He stood to show me all of him again. He covered his dick in the jelly, leaving a big glob on the tip. “Okay, Honey, scoot up to the pillows and let me up. I want you comfortable.”
After getting in position, he braced himself on his elbows over me and kissed me deeply. While distracted, Jimmy lifted my legs and spread them, giving himself access. I felt the tip of his cock against my pucker, which attempted to suck-in on itself in reaction, but I was open and ready. I whimpered, “Jimmy, please.”
Jimmy pushed. He started to slide in, stretching around him effortlessly, when I felt a pop happen as his head pushed through my muscle, the sting turning into a flaring burn. “Holy fuck, Jiiimmmyyy!” I was having a hard time breathing. It was so much. I thought the three fingers were the sensation I was going to be feeling.
After giving me a moment, Jimmy asked, “Are you okay, Honey? Tell me when you are ready. Or if you want me to stop completely.”
My chest and stomach were both expanding with air from the deep breathing I was having to do to help control the dual sensation of pain and pleasure. I finally nodded, hoping that once he starts pushing in some more, the feeling will spread and won’t be so contained to just the rim and opening.
Jimmy started to slowly slide in some more. He leaned down as best as he could from his position without fully pushing in and started to give me open mouth smooches. It distracted me enough, the feeling in my ass turning to full pleasure, moaning air straight into Jimmy’s mouth, whilehe was so calm, like this wasn’t affecting him at all. I reached up and put my arms around the back of his neck to brace myself.
Then I felt his groin touch my ass, his balls tapping against me. At that point, I completely engulfed Jimmy, my legs spread framing his body, while I moved my arms down around his shoulders, holding him closer. “I can’t believe you are in me. You feel amazing. Oh my God, is it always like this?”
“It will be,” Jimmy said breathily, his composure finally slipping, like he was having a hard time holding himself together now that there was nothing between us. “Are you ready for the main event, Honey? Because this was just the preshow.”
I snickered at his wording which made my hole clench around his dick, causing Jimmy to moan in pleasure and drop his head to rest on my chin.“Okay, Jimmy. Show me what you can do.”
Without even looking up at me or lifting his head from my chin, he pulled back a little and pushed in again, sending me up to the height of cumulonimbus clouds, turning my brain into its own thunderstorm of pleasure. I howled like a wolf at a moon peeking out of those same clouds.
Jimmy did it again but pulled out further. And again, and again, until he had a good rhythm going, pulling almost all the way out, feeling the lip of his mushroom tip on the inner rim of my ass before he pushed it smoothly back in again. His nut sack bouncing off my ass, swinging like a pendulum.
It sounded like my moan was one continuous noise. I couldn’t get any words out. The pleasure was overwhelming. I wouldn’t have noticed at this point if the house was on fire. The feeling I had at the base of my own dick felt like I was continuously juicing myself, when my dick wasn’t even being touched.
“Honey, I’m close to finishing. Are you ready?” Jimmy’s breathing was ragged and labored with all the work he was putting into my ass.
He leaned up and grabbed my cock at the base and squeezed, sending a bolt of lightning down into my balls and my ass. I arched off the bed at the feeling, “Jimmy, Jesus Fuck! How!”
He slid his hand up and down twice, making me blow instantly, losing all control. The first shot went over my shoulder, landing on the pillow, barely missing my own face. The rest flooded my neck and chest.
My ass clenched and squeezed Jimmy’s ramming rod from juicing so hard, making him have to push a little harder in, but it set him off. He yelped, “Honey, your ass!” I felt a warmness fill me up, Jimmy’s cock pushed all the way in, pulsing several times like it was trying to bounce but couldn’t while inside of me.
He collapsed on top of me, his dick still plugging my hole, the mess I shot now, all over the both of us. “Hoonneyy.” Jimmy kissed me sweetly. “You are my everything.” Kissing me again.
