Jean's Awakening Ch. 10

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Anal for the first time.
1.2k words
4.47
9k
7
0

Part 10 of the 12 part series

Updated 06/13/2023
Created 12/17/2022
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I slept the sleep of exhaustion and woke up realizing that I had about 30 seconds before I wet the bed

I couldn't open my eyes.

I moved and the pain in my ass reminded me why.

I gently opened my eyes with my fingers and ran to the bathroom.

I barely made it.

I had to use my fingers to get my mouth open as well.

In the mirror, I saw my mask, dried and cracked.

And God help me, I was proud of it.

Bobby was in my bed, smiling as I went to him.

"Will you kiss me?" I asked and he held out his arms.

I crawled on top of him, guided that enormous cock between my legs, and settled onto him before leaning forward and kissing him.

It was an odd kiss. My lips were so crusted with last night's semen that I didn't get the sensations I was used to.

"Do you want to fill me up or add to my mask," I asked when I felt him getting close.

"Honestly?" he asked, and I stopped moving.

"Of course honestly," I said.

"Jean," he said, and his hands caught mine, looking at me, holding my eyes with his, "what I would really like some time, is to have your beautiful ass."

I didn't reply for a few seconds and he squeezed my hands and said, "it's okay, I still love you."

"No, silly," I said, bending down for another of those crusty kisses, "I was just wondering to myself what the best way to satisfy you would be."

His eyes got big.

"Really," he said, looking for all the world like a six-year-old who had just been told he was going to Disneyland.

I kissed him again, lightly caressed that big cock, and said, "hold that thought," as I rolled off of the bed and went into the bathroom.

I was thankful, for the first time in my life, for the way the skin of my index finger would crack at the knuckle in the winter. The big jar of vaseline I kept in the medicine cabinet to soften the skin there would be necessary now.

I went back to the bed with his eyes on me.

I walked proudly, head high.

I grinned at him as I sat on the side of the bed and opened the vaseline jar, making a bit of a production of it.

I took a big dollop of the clear jelly and started right at the tip of that magnificent cock, slowly working my way down.

I did that for a minute, until he was slick, a thick coat of vaseline leaving him shiny.

I stood, and as he watched took another thick fingerful of the jelly on my right middle finger and used my left hand to spread my cheeks, bent over a little, and began lubricating myself.

He watched, apparently fascinated, as I did that several times.

I wanted to be slick for this.

I knew I needed to be slick for this.

I put the vaseline jar on the nightstand and went back into the bathroom and cleaned my hand.

I went back to the bed, crawled up, and straddled him.

He caught my hands in his and said, "Jean, you don't have to do this."

I giggled, kissed him, and said, "don't be silly honey. You want it and I want to give it to you, now hush while I work it out."

He gave me a soft little smile, a mixture of concern and happiness.

I lifted myself up so I was kneeling, reached down, and lifted his cock, guiding him, until I could slowly lower myself until he touched what he wanted.

I relaxed and lowered myself until I felt the pressure there.

We both held our breath as I gently lowered, feeling the pressure build.

A little more pressure built but he was still pushing against me. There was no beginning of penetration yet.

"Jean," he said again, "stop honey, I don't want to hurt you."

"shhhhhhh," I whispered, very softly.

I pushed back and he started to enter me.

I hissed, and waited, holding the position, taking time, and allowing things to stretch.

"Are you okay?" he asked.

"shhhhhhhh," I repeated.

I pushed back once more and his shaft was fully inside of me.

The sound I made can be best written as, "unnnnhhhhhhh."

The sound he made was "sssssssssssssssssssss."

I was cumming but it was different than anything before.

I was flowing again, I could feel my pussy running thick and hot and wet.

But there were no muscular contractions at all. Just the pure sensual thrill of that flowing.

I settled a little more, accepting more of his length into me.

He whispered softly, "oh Jesussssssssssssssssssssss."

I leaned forward and kissed him and then whispered into his ear, "do I please you, baby?"

"Yesssssssssssssssssssssssssssssssss," he whispered.

I lowered myself until I felt him bottom out.

I tried to adjust myself, to accept that final part of him into my bowels but I couldn't find the right angle.

I was breathing hard by then.

There was no pain, but I felt so full I was afraid I would explode.

I pushed, like I was trying to take a shit, and he hissed again.

The pressure of him against those strong muscles was delicious and I was flowing faster but still none of that instant release of an orgasm.

I was too impaled to rock my hips as I usually did during sex, so I began rocking my entire body, slowly pulling off of him and then settling back on.

When I started to get dry I reached up and grabbed the vaseline, pulled all of the way off of him, used my finger to lubricate again, and took him back into me all in a matter of a few seconds.

He cried out this time, "JESUS!"

I giggled and set up my rhythm again, pulling off and pushing back, slowly, masturbating him with my asshole.

I couldn't lean forward enough to embrace him but I could bend forward enough to kiss him.

And his arms could reach my back, and my ass.

I was tiring though, it was an awkward position.

So I sped up and squeezed as much as my stretched-out anus would allow.

My nose was running again, and thick mucus ran down my breasts.

When he came I exploded.

The orgasm, and it was an orgasm now, was huge. I squirted onto his belly and cried out his name.

My hands were on the small of my back, for support, but also pushing my boobs out and I could feel them sway.

When we finished, together, and he started to soften and I could finally lay on him, embracing him, telling him I loved him, and, of course, saying, "thank you."

He softened, as men do, and slipped out.

"No Jean," he said, "thank you. I always wondered."

"Well," I said, giggling, "was it what you'd hoped?"

"Oh God yes," he said.

"Good," I said, "because now that we know I can you can have it whenever you want it."

His eyes got big.

I giggled.

"Yes baby," I said, "and maybe next time from behind. I think I could take all of you like that."

He wrapped me in his arms and kissed me, hard.

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