An Affair With My Teacher

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Status: Finished  |  Genre: Adult Romance  |  House: Booksiesilk Classic Group

I run into an old teacher of mine and we end up sleeping together.

I had broken up with my girlfriend about a week before and ended up in the bar. I wasn’t looking to drink my broken heart away, to be honest, I wasn’t that heartbroken about the breakup, she had a husband and kids so I knew it was going to happen. I wasn’t even looking for another lover, just a drink or two. I was nursing my second rum and coke trying to decide if I wanted a third or head home to my empty apartment when I heard a voice from the other end of the bar that sounds vaguely familiar. I leaned on the bar and looked down the length of it to see if I recognized the person speaking. It was the craziest thing, it had been three years since I had sat in his classroom but I recognized Mr. Epenstein immediately. I remembered him so well not because he was the cutest teacher I ever had, but because he worked so hard to get the students involved.

Mr. Epenstein was clearly drunk arguing with another drunk man and it was getting loud. I heard the bartender warn them that if they didn’t quiet down he was going to toss them out. I grabbed my drink and made my way down to where he was sitting.

“Mr. Epenstein.”

He turned in his seat looking at me for a second. It took him less than a second “Anna, Anna Collett.”

“You remember me.” I was surprised since there had been smarter kids in my class.

“I remember all my kids.”

“Do you want to grab a table so we can talk?”

He nodded as he downed his drink. “Barkeep another and another of whatever this young lady is having.”

After we collected our drinks we made our way to a table and I saw just how drunk he was by the way he was stumbling. We sat down at the table and I continue to nurse the drink I had before.

“Are you still teaching?”

“Shaping the minds of the leaders of tomorrow,” he told me with a smile. “What about you?”

“I’m working a bunch of part-time jobs, I can’t really decide what I want to do.”

“You are smart Anna, I saw it even back when you were in my class, you can be anything you want to be.”

I smiled remembering how he was the first teacher that had got me interested enough to actually try. We just sat there for a minute sipping our drinks not saying a word then suddenly I opened my mouth and the words came out.

“How is your wife?”

He shook his head and the look on his face told me something was wrong. “She is visiting her sister.”

“You spend a few days playing the bachelor?”

“A month so far.” He looked even sadder as he admitted that. He downed his drink and headed to the bar for another.

I knew that I should change the subject or just taken off, but back in high school when the other girls were drooling over the buff gym teacher or cute science teacher I was thinking of Mr. Epenstein. He wasn’t handsome or athletic, short and pudgy with a huge bald spot he didn’t look like anything like the kind of teacher a young high school student would dream about.

I had no delusions about what was going to come from this. I didn’t see us running off to Europe and making a life for the two of us. It was going to be a fling, just a little fun before we both went our separate ways.

When he came back I slid closer to him and reached out to touch his hand. He didn’t seem to notice at first as we talked about the others from my class. Mr. Epenstein had kept up with what a lot of them were doing. I just slowly stroked the back of his hand as we talked. Suddenly he stopped in mid-sentence and turned to me.

“What are you doing Anna?”

I leaned in and kissed him on the mouth as I moved my hand to his thigh. He didn’t pull away, but he didn’t really return my kiss. I thought I had gone too fast and he was going to either bolt for the door or start a scene. I sat back leaving my hand on his thigh waiting for his reaction.

“I’m married.”

“This can just be a fling, a one night of fun and passion.”

“I was your teacher.”

“That is true you were my teacher, now I’m out of school and we are both adults.”

I saw him thinking trying to come up with some argument why we shouldn’t do it that would justify not sleeping with me, not for me but for himself. He hadn’t moved my hand from his thigh so as he struggled with his own conscience I slid it higher. Mentally he was struggling with the choice I had given him, but his body had already made the choice for him.

I kissed him again before I whispered. “My place is only a few blocks away.”

He downed his drink in one big gulp and nodded. I smiled and left mine on the table as I stood up and headed for the door. I wasn’t sure he would follow but before I reached the door he was beside me.


My apartment was on the third floor of this rundown tenement and climbing the stairs was an adventure with Mr. Epenstein barely able to stand when we reached it. The stairwell had a musky mildew smell to it that seeped into the apartments. But neither of us paid the smell any mind as we locked lips at my apartment door before I dug my keys out and opened the door to the cramped little place I called home.

We stumbled into the apartment and he began to fumble at the buttons of my blouse as we continued to kiss. I guided us back to the broken-down second-hand couch and pushed him onto it. I put a little wiggle in my hips as I moved over to the stereo and turned on the music. I turned around and found him smiling as he worked on unbuttoning his own shirt.

I slowly gyrated my hips as I reached up and unbuttoned my blouse as he watched me. I let it slip off my shoulders and fall to the floor as I reached up and unhook my bra. I don’t have huge breasts, but they are firm with thick nipples which were hard right then. I danced over to him still wearing my skirt. I hiked it up as I straddled his legs and lowered myself onto him.

He grabbed my ass squeezing my firm ass cheeks through my panties as I rubbed my nipples on his lips. He caught one between his teeth and gently bit down sending waves of pain and pleasure coursing through my body. I grinded on his lap feeling him grow harder as I grew wetter with excitement.

After only a few minutes I pulled away from him standing up again. I reached behind my back to unzip my skirt and let it fall to the floor before I dropped to my knees in front of him. He reached to undo his belt and I smacked his hands away playfully before I undid it myself. His pants were soon open and I reached into his boxers to pull out his cock.

It wasn’t very long and a little on the thin size, but the size didn’t matter it was hard and I wanted it. I leaned down to kiss the head before I parted my lips and slowly lowered my head further. I felt him lean back as he let out a soft moan of pleasure. I worked my mouth up and down his manhood as I gently squeezed his balls. It didn’t take long before I felt him throb in my mouth and I knew he was close.

Pulling away again I laughed. “Do you want me to finish or would you rather take this to the bed?”

He was gasping for breath as he smiled. “I can’t wait to see what you can do in a bed.”

He quickly finished undressing before following me into the bedroom. I sat on the edge of the bed but before I could remove my heels Mr. Epenstein was kneeling in front of me lifting my right foot. He undid the strap and slipped the shoe off before gently massaging my foot and calf. A soft moan escaped my lips and he smiled up at me before switching to my other foot.

I laid back and let him massage my feet and calves but I soon felt his hands sliding up my legs. He hooked my black thong with his fingers and I lift my hips so he could pull it off. He began to kiss my inner thighs as soon as my thong was off. This is why I prefer older lovers, they are not in a rush to feel their own pleasure, many seek to make their partner enjoy the sex as much as they do.

I gasped as I felt him kills my pussy and plunge his tongue into me. He licked me as his hands slipped under me and cupped my ass. He lifts me up as he pushed his tongue in deeper and I felt waves of pleasure running through my body.

I was couldn’t take it any longer and I sat up just enough to grab Mr. Epenstein’s head and pulling him up. He kissed his way up my body taking the time to suck and nibble on my nipples. He pushed into me and I wrapped my legs around his hips pulling him in further. He slowly began to fuck me and pulled his face down to mine so I could kiss him.

The pleasure built and I could see he was fighting to keep from cumming too quickly. He wanted me to enjoy it as much as him, but I knew he wasn’t going to hold on much longer. I slipped a hand down and rubbed my clit as he continued to work his cock in and out of me. I felt my own organism building and pulled his mouth to mine again as we both came together.

He climbed onto the bed next to me after he had pulled out and we snuggled as we kissed.

“Give me a few minutes and I’ll be ready to go again,” he told me and I just kissed him as I held him tight.

I don’t know if it was age or the alcohol but he was soon asleep and I smiled as I hugged him.


The next morning I saw him to the door after he was dressed. We shared a kiss but there were no false promises made or lies told. We didn’t even speak of what had happened the night before. His wife returned a week later from what I heard. I see him from time to time, but we don’t speak even if he is alone, we just smile at each other remembering that one night.

Submitted: July 10, 2021

© Copyright 2023 Gypsy Rose. All rights reserved.

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Add Your Comments:



Nicely explicit when we get to the meat of this story! It's a curious point worth elaborating why the speaker finds a man she admits is unattractive to be so sexually alluring. Is it the alcohol? Is it loneliness? Personality? Anna is quite provocative, hitting on her married teacher. She admits that her previous lover was married also, but Anna has no apology about it - just mentions it in passing. How curious.

Sat, January 22nd, 2022 11:10pm


There is a lot of reasons I found him attractive. He cared about his students, he remembered me after 3 years, I'm not sure any of my other teachers would. He was smart, I find intelligence more attractive than what a person looks like. Of course, my shrink says I search out people to get involved with when there is no chance for it to last. I also should mention I like older lovers; some don't have the stamina but the make up for it with experience.

It is always a pleasure when I see a comment from you DampKitten.

Sun, January 23rd, 2022 5:33pm


Oh, wow...then this is real. Okay, then.
So, I guess the point I was making is simply (as a reader) I want to hear those things you stated. Even if the account is biographical, you can always make a few changes to underscore a point. So, you could have Epenstein ask and Anna elaborate. I will say that 'not knowing' doesn't diminish the impact of the story - it just answers my curiosity.

So, just wow on this relationship with a married woman. That would be an interesting story too. It would be good to do a novella with a few chapters, one of which is a session with your shrink.

Mon, January 24th, 2022 1:52am

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