Teacher's Pet Pt. 08

The discussion had made my cock hard, thinking about fucking Caroline and what I had learned from Sharon and Judy. Sharon's hand brushed against my almost completely rigid cock.

"Oh someone was turned on talking about fucking," she said as she stroked me lightly.

"Have you ever played with her ass?"

"No, I've not tried that. Not really sure how it works."

She chuckled, "Well its kinda like fucking a pussy, but much tighter. My ass does not get wet like my pussy so you have to bring your own lubrication to the game. I understand it feels incredible on the cock. It certainly feels good in my ass. But some people don't like it."

"Like Judy?"

"Exactly, but I am not sure she ever learned to do it right. If you do it wrong it can hurt and make you not want to do it. If the guy is forcing it or clumsily doing it, it can be bad."

Her talking about anal sex was really turning me on. My cock was rock hard by now and remembering what it looked like fucking her from behind earlier made it even harder. Sharon continued to stroke it lightly.

"Do you like it in your ass?"

Sharon laughed, "Yeah I do it sometimes, prefer it in my pussy, but I usually cum pretty hard when I do it."

She was squeezing my cock really hard. Slow strokes. Looking into my eyes.

"Want your first ass to be mine?"

My cock twitched in her hand as I nodded my head yes.

"You want to fuck my ass?," she asked squeezing my cock harder.

"Yes," I answered.

"Good cause I feel like a cock in my ass this morning."

My cock was aching, it was so hard. I had never really heard of anal sex before getting in with Judy and Sharon and now I was going to get to do it.

Looking into my eyes she said, "I need you to listen to what I tell you. It can really hurt if we don't do it right. Understand?"

Nodding my head I said, "Yes."

"Good. Need you to go slow when we start. Let me work you into my ass. You cannot not get too excited and start pounding my ass before we are ready."

"Ok." I was just following her lead, I had no idea what was to come.

Sharon was slowly stroking, squeezing my cock. She reached over with her other hand, turned the lamp on and grabbed the KY Jelly, laying it on the bed next to me.

She then leaned over and took my cock into her mouth and proceeded to suck my cock for a couple of minutes, occasionally resting with my cock in her throat. Sharon let my cock fall from her mouth and slid up next to me.

"I need you to help me get warmed up."

"Tell me what to do," I said. I was ready to do anything she told me to do.

She smiled, grabbed the KY and got up on all fours. Opening the bottle, she squeezed the gel onto her fingers and moved her hand to her asshole. I moved so I could see what she was doing and was behind her. Sharon spread the gel around her asshole and then began to ease a finger into her ass.

"OH, HMMMMMMMM," she moaned as she began to work the finger into her ass.

I watched amazed as her ass puckered around her finger. She reached back with her other hand to give me the KY.

"Squirt a little more around my finger."

She pulled the finger almost all the way out and I spread more gel on her fingers. The finger moved back into her ass. After a minute of fingering her ass she brought a second finger up and began to ease it into her ass. She was grunting and breathing a little heavy. I could also see her pussy starting to glisten. Slowly she worked the two fingers into her ass and then held them as deep as she could in her. Working the fingers around her ass it began to loosen up on her and she moved her fingers more easily.

She was moaning and working her ass with two fingers. Looking over her shoulder she said, "Put some gel on your fingers."

I took the KY and spread it on the fingers of my right hand. Sharon pulled her fingers from her ass.

"Slide your finger into me."

I tentatively touched my index finger to her asshole. Pushing it slid smoothly into her ass and I began to slide it in and out. She was pushing back as I finger fucked her ass.

"Put another one in," she panted.

Pushing a second finger into her ass caused her to moan deeply. I could feel the heat and her ass squeezed on my fingers. Sharon was slowly rocking back on my hand as my fingers slid in and out of her. We continued like that for a couple of minutes. It was amazing watching her ass clench around my fingers and my cock was as hard as it could get.

Sharon pulled forward and my fingers slipped out of her. Reaching back she grabbed the KY and squirted it into her hand. She grabbed my cock and began to smear it on me. Moving the bottle near her ass she squeezed some right on her asshole.

"I need your cock in me now," she said as she maneuvered my cock to line up with her asshole.

Sharon rubbed my cock against her asshole. Holding me steady against her she began pushing back against my cock. Her ass resisted but she held the head of my cock against her ass. Suddenly she gasped as the head popped into her ass, twitching as I remained still behind her. I wanted to push it in deeper and started to but remembered her telling me to not move as we entered her ass.

"OH GOD, I forgot what this felt like. Give me a minute to get used to it," she said panting lightly.

It took all my willpower to not shove my cock into her ass. I could feel her clenching my cock, squeezing it tightly. After a couple of minutes I could feel her begin to push back against me, my cock bending as she did. Holding my cock steady it suddenly popped halfway into her ass, her breath shooting out of her.

"Ah fuck, that hurts, don't move. Let me settle a little more."

Her ass was clenching, squeezing, crushing my cock. It was hotter than a pussy and much tighter. I could feel her starting to loosen up as we waited for her to be ready for the next part.

Taking a deep breath, she looked back at me," I think I am ready. Stay still and I will push back against you."

I nodded my head yes and put my hands on her hips. She put her head down on the bed and pushed against me. Her ass resisted and then I suddenly slid all the way in her ass, my balls slapping against her pussy. She gasped and took a couple of deep breaths. I held onto her hips and did not move. Her ass was incredibly hot and tight.

"Whew, that hurts but feels so good. Love the full feeling in my ass. Wait a minute and then we can get started."

"Ok, this feels a lot different than your pussy. Hot and squeezing my cock tight."

She smiled back at me.

After a minute she turned to me, "Start slowly, take it easy at first."

Holding her hips I began to slowly fuck her ass, pulling my cock about half way out then pushing it back in. Being in her ass was so different from her pussy, hotter and tighter. I was going easy, not wanting it to end and not wanting to hurt her. Sharon had her head on the pillow. I could feel her hand reaching back and touching my balls as I stroked in her ass then her hand moved to her pussy.

Looking up at me she said, "Start going faster. Fuck my ass hard."

I did not need any encouragement for that. Had been waiting for her to give the signal to start really fucking her ass. Pulling her to me by her hips I rammed all the way into her. Sharon had slipped her fingers into her pussy and I could feel them pushing into her as my cock moved in her ass.

"Oh, god, yes, just like that," she panted as I began to fuck her ass as hard as I could. It was unbelievable. In my sexual inexperience I had not considered someone's asshole as something to stick my dick in. But here I was, balls deep in an older, more experienced woman's ass.

Sharon was moaning, working her pussy with her fingers, her breath beginning to get ragged. I could feel the cum building up to explode out of my cock, I was not going to last much longer.

"OH YES. Cum in my ass, fill it up," Sharon said as another orgasm slammed into her causing her to push her fingers as deep as she could into her pussy and for her ass to clench my cock even harder.

Her gasping for breath sent me over the top and pushing as far as I could, I began shooting cum deep in her ass. It was like her ass was milking my cock.

"YES, fill me up, I can feel it pumping. FUCK."

Sharon collapsed on the bed, my cock still embedded in her ass. I laid on top of her, both of our hearts beating rapidly. Slowly her ass released its grip on my cock and I slid out of her ass. Rolling off of her, I was laying next to her on my side with my hand rubbing over her ass and lower back.

Sharon purred quietly as I stroked her back. Turning her head she looked at me and smiled.

"That was amazing. I don't do that often, but after getting fucked like that I need to do it more often. Problem is guys won't be patient like you were and go right to town. Makes my ass hurt a lot."

I smiled back at her, "Thank you for being a great teacher. I had no idea that we could do that, it is an amazing feeling."

We laid there quietly for a while.

Sharon leaned over and kissed me and then began to get out of bed "I am a mess, need to clean up. Something is leaking out of my ass," she said smiling.

I watched as she went into the bathroom, her freshly fucked ass jiggling as she did. Hearing the shower start after a couple of minutes made me decide to clean up too. Joining Sharon in the shower we cleaned each other thoroughly. When we finished we went back to bed and slept well into the morning.

Sharon and I spent the next couple of days fucking all over her apartment, including another session in her ass. Even though it would be a while before I got the chance to fuck another ass, I would always remember Sharon's lessons.