The Halloween Party

A cougar teacher and a former student reunite at a Halloween party and begin to have a have a secret affair.


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I had always loved dressing up for Halloween as a child and wearing fancy and colorful costumes and pretending to be someone else, even if only for a few hours. I truly looked forward to it all year, and getting to go to school dressed up and show off our costumes. The class parties where the teachers would bring in usually homemade treats, or the male teachers would bring in treats their wives had made and a few of the students mom’s would as well for the class. There was always lots of goodies to look forward to, from fudge, brownies, caramel coated apples and popcorn balls and tons of candy and cupcakes and punch. The decorated classrooms with fake cobwebs, black cardboard cutouts of bats and witches and muslin ghosts hanging from fishing line.

It was truly a wonderful time. Now that I am a teacher myself, I like to have the same sort of fun atmosphere for my own students. I teach grade nine and ten English, so the students are not as enchanted with decorations and costumes as the younger elementary school students are, but some still enjoy it and many still seem to get dressed up. Halloween was on a Saturday night that year, and on the Friday night before, there was a party at the principals house. I didn’t really care for her, but she was my boss, so I figured I’d best put in an appearance, and most of the staff was going to be there dressed up, it could make for some funny pictures at the very least.

I had decided a few weeks before on a Southern Belle type of costume with a plunging neckline to show off my ample cleavage and large hoop skirt. I had questioned how I was going to drive in the hoop skirt, but thought since it was a party and I’d be drinking it was easier just to take a cab and forget about getting behind the wheel with the ungainly skirt. It looked beautiful, but certainly was not meant for driving. I got to the principals house and a few others were arriving at the same time and it was fun to see people dressed up, and the front yard had been decorated beautifully, with fake headstones and bales of hay and pumpkins and the path to the door from the driveway was lined on either side with many jack’o lanterns, it looked lovely.

The cab driver had to help me out of the backseat since the large hoop skirt was difficult to manage on my own. I’d piled my blonde hair up and had granny boots on under the dress. Only the tips of them showed as the dress was dragging the ground. I walked up to the door and was greeted by the principals teenaged son, Andrew.

“Andrew! I haven’t seen you since you graduated last year,” I proclaimed.

“That’s right, Miss Rogers, it’s nice to see you again,” he said politely.

“Dracula, huh? Ha ha! You look great, it’s a fantastic costume,” I said truthfully.

Andrew had been a student of mine for two years a few years ago, I always liked him and had even semi flirted with him on a few occasions. I likely shouldn’t have, but he was very witty and had a good turn of phrase and we bantered well together, I’d often wished he was a few years older when he’d been my student, but now he WAS a few years older and no longer my student…I grinned to myself at my naughty thoughts that quickly ran through my mind. He ushered me into the home and the downstairs was as beautifully decorated as the outside was with many festive decorations.

He wasn’t quite 19, but what a handsome boy he was, dark hair and dark eyes, slim build, mischievous grin, so fresh faced and sweet. There were waiters from the catering company walking around with trays dressed in costumes offering the guests beautifully presented hor d’oeuvres and colorful punch drinks served with small bits of dry ice so they looked as though smoke was pouring over the sides of them, it was a feast for the eyes, all the autumn and Halloween decorations and everyone looking so whimsical. I smirked to myself most of the teachers looked far better in costume than they did in their everyday wear, here at least many of them had paid attention and looked festive and colorful.

I walked with Andrew over to a far corner and we sat down and enjoyed our punch with the mist pouring out of it and caught up on what he’d been doing the last year since I’d seen him last. He told me he was in university and going to go to law school afterwards, and I thought to myself he’d be a good courtroom lawyer with his flare for words and love of attention and crowds.

“So what about you, Miss Rogers, what have you been up to,” he asked me.

“Please, I’m not your teacher anymore, no need to be so formal, call me Laura,” I insisted.

“Alright Laura, have you been up to anything exciting in the last while since I have seen you?” He asked, looking deep into my eyes with his piercing dark ones that looked as if they were peering right into my soul.

“No, same old stuff, school, a bit of volunteering now and then, some gardening, really nothing exciting at all,” I confessed.

“What? No hot romances or trips around the world?” he joked.

“‘Fraid not, I wish!” I said in all honesty.

“But you’re a sexy, mature lady, Laura, how is it the guys aren’t falling all over you?” he asked sincerely.

“Good question, young man, guess I’m just not looking in the right places, or don’t go out enough,” I countered.

“This is true, you’re not going to be dating the students, and they are the ones you are around all the time,” he said.

“Very true, well you get into a comfortable routine, and time slips away, weeks become months, months become years, years become decades,” I said trailing off.

“Now don’t get all down on me, you’ve got plenty of living to do!”

And with that he pulled me up and we started to dance to the “Monster Mash” song and he spun me around and then pulled me close and I all of a sudden had feelings and desires for Andrew I wasn’t sure I should be comfortable with, especially standing in his mother’s, my boss’s, living room. And with that thought who should approach with a rather stern look on her puckered face than his mother.

“Andrew, you shouldn’t be monopolizing Miss Rogers’ time like this, go into the kitchen and see if the caterers need any help with anything,” she said dismissively towards him and he turned on his heel and his black satin red lined cape swirling around him as he marched off towards the kitchen.

“Your son has grown into a handsome and ambitious young man, I didn’t expect to see him here tonight, but I’m glad I ran into him to catch up,” I explained.

I wasn’t quite sure how to read the expression on her face, but it wasn’t a positive one, that’s for sure. Over her shoulder I saw Andrew mimicking her and I was trying not to smirk, as he was indeed a very accurate mimic of the old bat, and I just wanted to get away from her. Luckily a few more people were arriving in the door and she went over to welcome them and I went over to where Andrew was standing and again was taken back by how handsome he had grown. It’s a good thing I wasn’t this aware of his appeal when he was my underage student. He looked around for his mother and she was nowhere to be found. He grabbed my hand and pulled me down the hall and into a media room. It was beautiful, the wall mounted screen was the largest one I’d ever seen in a private home, with two rows of comfortable seats, it was spectacular, with black walls and speakers, pot lights, I was very impressed.

Andrew sat me down in one of the seats and sat down in the seat beside me and took my hand. At the same time I felt both uncomfortable and aroused. He was a former student half my age and we were in his mother’s house and she was milling around and I had no idea if she might waltz in here at any moment. He leaned in close to me and I could feel his breath on my cheek and I looked into his dark eyes and was lost in them, caught up in the atmosphere, the costumes, being lonely, I must admit I didn’t stop him when he leaned in and kissed me. He pulled back as if to see if it was ok to proceed and I didn’t resist and let him continue to probe my mouth with his tongue. He was so young and alive and filled with youthful energy, I really wanted him. It had been several years since my last relationship and I now realized how much I missed being touched, kissed, held and made love to.

“You’re beautiful, Laura, I want you,” he whispered in my ear as he kissed my neck and his hand found its way to one of my breasts and started to caress my nipple which was hardening at his touch as my breath quickened. I was so afraid his mother was going to come looking for one of us. We kissed passionately, and I ran my hand down over his black satin pants and felt how hard his young cock was through his pants and I kept rubbing my hand over and over his satin covered cock.

“I want to taste you,” he said huskily in my ear.

He got down on his knees in front of me and lifted up my hoop skirt and pulled my panties to the side and started to lick me in a way that was driving me absolutely crazy, I was already very wet from being so turned on kissing him and touching him and he was indeed tasting me, lapping at me, sucking on my clit, nibbling on it, and sucking on my juicy inner lips and sliding his tongue inside of me and teasing me as I rubbed my own nipples. All of a sudden I heard the door and pulled down the upturned hoop skirt and totally covered poor Andrew under there.

“Miss Rogers, are you alright, I came to see where you’d gone to,” Andrew’s mother stated. My heart was racing, knowing her son was under my hoop skirt, and was continuing licking me even though the old bat was less than ten feet away from us.

“I had a bit of a headache, I just came in here to get away from the noise for a bit, I’ll return shortly,” I promised.

“Yes, you do look a bit flushed, sit in here for a while, I’ll go get you some aspirin,” she offered.

“No, it’s ok, I had some in my purse, I’ve already taken a couple, once they kick in I will be fine. Thanks for your concern,” I said.

As the door closed, Andrew emerged from under the hoop skirt laughing.

“It’s not funny, if she’d ever caught on, I might lose my job,” I worried aloud.

“Oh don’t be silly, I’m over eighteen, you haven’t done anything wrong,” he countered.

“She might not see it that way,” I questioned.

“She won’t be back, she’s waiting for that aspirin to kick in, after all”, he laughed.

I leaned back and tried to forget that awful woman and just enjoy the teenager under my skirt, which I must say, was very enjoyable indeed! Fuck, he knew how to lick pussy, I will give him that. I think he was the best pussy licker I’d ever had. I had to be quiet as I orgasmed, I sure didn’t want his mother returning to see me in the throes of orgasm with her son between my legs.

“Andrew, I’d really like to continue this, but I just don’t feel comfortable here, we already had one close call, let’s go back to my place, ok?”, I offered.

“You’re right, too risky,” he agreed.

“I took a cab here, should I call one, or can you drive me, or what should we do? I don’t want your mother to see you driving me home, that’s also asking for trouble,” I said.

“Yeah, tell you what, I’m parked on the street since mom wanted the driveway clear for the guests, let’s go out the kitchen door and out the back, she won’t see us leave at all,” he explained.

So we crept out the door and down the hall to the kitchen which was busy with catering people and out the door with no one paying much attention, they were too busy refilling their trays to worry about us escaping unseen through the back door. We walked the half block to his car and he helped me in with the ungainly skirt and off we drove to the peace and quiet of my little cottage style house around fifteen minutes away.

“God I want to fuck you,” he said in that sweet, young voice of his. “I’ve wanted to fuck you since you were my teacher. Do you have any idea how many nights I jerked off thinking about you and fantasizing about bending you over that desk after school?”, he confessed.

He pulled into my driveway and I let us in my door. He pressed me against the door, and my heaving bosoms were pressed right against his chest, my nipples two points, hardened with desire. We started to undress each other as we walked kissing to my bedroom, a pile of a satin cape, hoop skirt, bodice, pants, all in a telltale trail towards my room. I was standing there in my damp panties and push up bra, and Andrew in nothing but his boxers as we fell onto the bed breathing heavily as we explored each others bodies with our hands and tongues. Our underwear was soon a pile on the floor and we were naked and writhing all over one another. Fuck, he was hot. So firm and young and eager to please. His cock was around seven inches I’d estimate, a good size, and thick, any time now it was going to be inside my greedy pussy and I couldn’t wait.

We kissed and stroked each other and the room was filled with our panting. He started sucking on one of my nipples and opening my pussy lips with his fingers, finding my juicy wetness and stiffened clit, he rhythmically rubbed me as I gripped my fingers in his shiny, dark hair as he suckled me. I had my legs open to him, my shaved cunt slick with my juices as he teased me faster and faster. I reached down and grabbed his hardness and pumped it vigorously in my hand. He had a beautiful, veiny shaft and I smoothed his precum that was oozing out the tip of his dick all over it, and massaged his balls as well. I pushed Andrew on his back and knelt between his legs and lowered my head down to that young teenage cock and finally took it in my mouth. Drooling all over it and swirling my tongue around the head licking it like a melting ice cream cone, and tracing my tongue up one side and down the other. I could feel his hand on the back of my head pushing it down, making me gag a little bit on his long, thick cock, but I didn’t mind, he was a beautiful, young boy and I loved having him in my bed.

I felt his load of warm cum, gush into my throat, squirt after squirt, I think seven in all, and it was dripping down my chin as I swallowed it down. He maneuvered me onto my back and then climbed on top of me and impaled me with that throbbing, hard cock, all the way up to the balls. I could feel my cunt lips spreading open wide to his young cock as he thrust inside of me and I gripped his shoulders. It was a tight fit, but he got it in and slowly started to rock back and forth inside of me, his cock grazing against my clit. I wrapped my legs around him, pumping his dick deeper inside of me with every rocking motion. I could feel another orgasm welling up inside of me, and I could tell from his breathing that he was getting close, too. I urged him on, “Fuck me faster,” and he picked up his pace and all of a sudden I felt the first waves of my orgasm approaching and my pussy lips clenched around his cock milking him and he then exploded inside of me, his bare cock unleashing its torrents of cum. We lay there, him still on top of me, inside of me, catching our breath.

“I never thought all those nights I jerked off to you when you were my teacher that I’d ever get to really fuck you,” Andrew said.

“I hope it was worth the wait,” I replied.

“It sure was, Laura. My school is a couple hours drive away, but I can certainly come home on the weekends to see you if you’d like me to,” he said.

“I’d like that very much, Andrew. Now we just have to keep your mother from finding out!,” I laughed.

“Oh don’t worry, I’m a crafty one,” he promised.

“I’m sure you are, now young man, I’d like a repeat of everything we have just done tonight, are you up for the task?,” I said through my smile.

“Oh yes, Ma’am, I’ll get right to it!”

Once again, sexy young Andrew began his attentions towards me and my always greedy pussy and we continued to fuck until the sun came up.

“Your mother is going to wonder where on earth you went to,” I stated.

“Yes, not quite sure what I can say, maybe that I went out for some fresh air and ran into a buddy and went back to his place and crashed on his couch, it could happen,” he said.

“I guess so,” I said.

And with that, he leaned down, kissed me once more, so sweetly and deeply and said he’d be back next weekend and was I free.

“Of course, I am already looking forward to spending the weekend in bed with you,” I admitted truthfully.

“Oh I bet, you horny cougar,” he said teasingly as I laughed and playfully reached to swat him as he sidestepped it.

“Ok Laura, I have to go now, but I will return, my lady…”

And with that he left, and I was left there laying smiling on my back, anticipating all the fun yet to come. Yes, I really did still love Halloween.


The above story was written by me. If you see the above story posted on any other websites than Climax Connection, Literotica or Lush Stories, it has been stolen, posted and copied without my permission. Please notify me if you see it on any other sites.

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