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Here is my entry into the Halloween Contest. Any votes and comments would be greatly appreciated. Thank you.
I always thought of myself as a hopeless romantic. It seemed like I was always falling for the girl who would be the most unattainable for me. I think it started with my first crush on my teenage babysitter when I was 10 years old. She was so smart and nice to me and I had so much fun with her, who could blame me for getting a crush on her. When I was starting to be aware of the opposite sex, it seemed like I skipped over girls my own age and looked at girls who were years older than me. I did date a few girls my own age in middle school, but they didn’t interest me as much as the girls in the next grades. I never really thought of it as a fetish or anything like that once I learned that term, I could appreciate the beauty in girls my own age, but I just wasn’t fully drawn to them.
During my freshman year of high school, I had a huge crush on my Honors English teacher, Miss Walker. She had only been teaching for a couple of years and was in her mid-twenties. She was beautiful in a bookworm sort of way with her long brown hair and her black frame glasses. She was modest in the clothing that she wore but you could tell that she was fit and she had large tits that had to be D cups. Compared to most of my other teachers she seemed genuinely excited to be a teacher and found a way to make every class interesting. Honors English was the class that I excelled the most in so it was the only class that I liked to raise my hand and speak in. I got a thrill every time Miss Walker said how I was right or that I had brought up a good point.
Miss Walker was helping out with the yearbook class which the older English teacher next door taught so she always had her classroom open before and after school, and also during lunch. I took to hanging out with my friends in her class during lunchtime since I had her class the period after lunch hour. My friends had classes across campus so they would leave a few minutes before lunch ended to make it on time. I would use this time to read a little or polish off some homework. Miss Walker saw I was reading and asked what book I was reading. When I told her, she said how she had read that series a couple of years ago and how much she loved it. That got us talking about other books and then T.V. shows and movies. I loved talking to her one on one. When she would smile, I felt my heart melt at the thought that her smile was just for me. I know I was crazy for having a crush on a teacher, but I couldn’t help but feel that way for her.
I didn’t have her as a teacher for my sophomore or junior year, but I still hung out in her classroom for lunch almost every day. I thought it would be weird at first when I was no longer in her class, but when I spent the first week of my sophomore year away from her classroom and then decided to finally eat lunch there, she said how she had missed me and wondered what had happened to me.
I signed up for AP English in my senior year. Since I had a free period after I made my schedule, I decided to take yearbook class as well that year. The old teacher for both classes ended up getting sick and having to stop teaching that year right before school started, so I was surprised when on the first day of school Miss Walker was the new teacher for both classes. It felt good to be in her class again. I hit my growth spurt during the summer before senior year and put on some lean muscle from joining the tennis team with my friends. When Miss Walker saw me for the first time, she seemed confused for a moment and had this look in her eyes that I didn’t know what it meant. Now I was taller than her by several inches and she had to look up at me.
Between having two classes with Miss Walker and spending a lot of my idle time at school in her classroom we talked more than ever. My friends teased me all the time about my crush on Miss Walker and I didn’t blame them, but at the same time, I just loved being around her.
When I turned eighteen at the start of October I was surprised when Miss Walker gave me a present in between class periods. I unwrapped it and it was a box set of one of my favorite book series. I told her how they had been lost during a move and I hadn’t gotten around to getting them again. I was so happy that I couldn’t help myself and I hugged her. Miss Walker seemed to tense up for a moment and I realized what I was doing. I was about to let go but then Miss Walker hugged me back. The hug lingered and then she reluctantly pulled away. We had just enough time to separate before a student walked in.
For the rest of the month, something seemed different about Miss Walker. We had already talked a lot together before, but now she seemed to be paying me extra attention. She also started to come to school more dressed up than usual. Before she would never wear makeup and her clothes were often loose on her and hid her curves, but now she started to come in with some makeup that highlighted her natural beauty and wore outfits that clung to her curves better Finike Escort and showed off how amazing her body was. Some of my classmates speculated that she had a boyfriend.
My school held an annual bonfire the Friday nearest to Halloween, this year Halloween was on a Saturday. It wasn’t much, but it was one of the only events that the school put on that most of the students liked to attend. I guess there was something about a giant fire, games of chance, food, and club booths that drew in students. My money was it was the fire that did it.
Miss Walker was running the yearbook/spooky books booth and had asked for volunteers to help out. I had raised my hand immediately to help out. I knew that a few of my classmates thought I was a teacher’s pet, but I didn’t care as long as I got to spend more time with Miss Walker. Another student and I were chosen to help out, but when I showed up to help Miss Walker to set up after school, she told me how the other student had texted saying that she was sick so it was just the two of us working the booth that night.
Miss Walker was dressed up in the same witch costume that she had worn during school. It wasn’t super revealing, but at mid-thigh length, the skirt was shorter than anything else she had worn before, and the blacktop allowed some of her ample cleavage to be seen. Her costume looked like a sexy Hermione outfit with her long golden-brown hair, the short cloak, and Gryffindor emblems on it. I tried my best to not stare as we talked, but every now and then my eyes would be drawn to her tits. I tried to be sneaky when I would look at her tits and I was confident that she hadn’t caught me. I had spent the last four years checking her out in secret. Like usual we talked about the books we liked and what shows or movies we had recently watched. We tended to have a lot of the same interests, and when we found something that the others hadn’t read yet we would share books. When we talked it didn’t seem like how a student and teacher would talk, but rather like two friends talking.
The bonfire was dying out and the event was ending. Miss Walker started to put her stuff away into boxes. I helped her without being asked. “You don’t have to help, really, I got this, go have fun with your friends,” she said.
“I have more fun with you,” I said with confidence that I had no idea where it came from.
She smiled, but then said, “You really have spent enough time with me tonight.”
“What if I said I wanted to spend more time with you tonight?”
I thought I saw her blush, but then she turned her back to me and bent over to pick up a box. Her skirt clung tightly to her plump ass. She looked back and caught me checking her out again, “Are you going to help me out then or just stare?”
“Sorry,” I said. It took a few trips for us to take everything to her car.
“Thank you, it would have taken me twice as long to get this done,” she said as we put the last box into her trunk.
“Anytime for my favorite teacher. Have a good night.” I said and turned to start to walk home.
“Wait…do you want a ride home?” She asked.
“I don’t mind walking,” I said, playing it cool when really I was excited that she had offered to give me a ride.
“You kept me company all night and helped me out, let me repay you.”
“Ok, you win,” I said. I walked to the driver’s side door and opened the door for her.
“Oh, thank you.”
“You’re welcome.” It felt odd sitting in my teacher’s car. It was cluttered with some books and papers that she had had to move off of the passenger seat for me to take my seat, but other than that it was clean and smelled like cherry suckers.
“Sorry for the mess,” Miss Walker said as she threw some more stuff into the back seat.
“It’s not that bad.” She asked where I lived and when I told her she said that we didn’t live too far away from each other. We drove in awkward silence for a minute. We normally talked and got along so well, but being with her right now in her car was outside of my usual environment with her so it threw me off a little. I knew that Miss Walker giving me a ride home wasn’t technically wrong, but was something that would be highly frowned upon if the school found out.
“So,” she finally said, breaking the silence, “are there any girls in that you like?”
We had talked about so much together, but we had rarely talked about anything overly personal like that before. “No, not at the moment,” I said honestly as long as I didn’t count Miss Walker, who was a woman, not a girl.
“What about Heather, you two seem to really get along in class.”
“She’s nice,” I said.
“She is a beautiful girl, and I’m pretty sure she likes you,” Miss Walker said.
“Yeah she is, but she isn’t exactly my type,” I said.
“Oh, what is your type then?” She asked after a moment.
“While, I like a girl who is smart, funny, and also has a nice personality.”
“She seems to have all of those things,” Miss Walker said.
“Yeah, but I also like my girls to be a little Finike Escort Bayan older, I don’t really think I am all that into high school girls, to be honest,” I said.
“You are still young, maybe you should give some of the high school girls a chance. I am sure Heather and some other girls are dying to get a chance at you.”
“I doubt it,” I said.
“Don’t talk like that. You are one of the nicest and smartest students I have ever had, and you are handsome too. There has to be someone that you like,” she said.
Why was she asking me about this? Did she know about the secret that I had been holding in for years? I had dreamed of the perfect moment for years to confess my feelings for Miss Walker. I questioned if this was the time. Why would she be asking me so much about this if she wasn’t curious for some reason other than just wanting to make idle small talk?
“There is someone who I have had a crush on for almost four years now,” I said.
“Who is it?” she asked.
“I don’t know if I should tell you,” I said, still debating if I should or not.
“Come on, I promise I won’t tell, don’t you trust me?” she asked with a pout.
“Ok, she is older than me-“
“Is she in college?” Miss walker asked. We made it to my house and she parked in front.
“No, a little older than that. She is kind and smart and beautiful, and I have had a crush on her since I first saw her.” I paused for a moment, thinking about backing out, but now that I was starting to tell her there was no going back. “Every day I see her, I can’t help but think about how amazing she is, and how much I love talking to her.
“Who?” she asked quietly.
“It’s you.” Here it was, I said it. The moment I had thought over for so many years now, what was she going to say, how was she going to react? Did I just ruin my friendship with her and was the rest of the school year going to be super awkward now? The silence stretched on for a minute as my mind went into overdrive thinking about all of the different, mostly bad, possibilities.
“Oh Justin, I’m flattered, really I am, but I am your teacher. You have to know that you liking me can’t come of anything right? It would be illegal and immoral if I had a relationship with a student.”
“But I’m eighteen now and I know, that’s why I have never said anything,” I was already starting to feel how much of an idiot I was for thinking that I had a chance with her.
“I could still lose my job. Plus, I’m way too old for you and you deserve to be seeing girls your own age and enjoying high school while you can.” She must have been able to tell how upset I was because she reached out and held my hand gently.
“You’re not too old for me, your only ten years older, that doesn’t mean anything to me. I’ve tried to get over my crush on you, but none of the girls my age can come even close to you,” I said.
“Justin, stop,” she said and grabbed my hand.
“No. I have held this in for years now and I have tried waiting but I can’t. How do you expect me to try and date other girls when you are the one who has my heart and I think about all the time? It wouldn’t be fair to them when all I would do the whole time is comparing them to you. No one else is as beautiful or smart as you. You always talk about yourself as if you were some old maid but you are still young and amazing and I hate hearing you talk about yourself like that all the time. We are already such good friends. I can’t help but think that if I was with you then I could show you just how amazing you really are.”
I felt like I was fully spent after that outburst, I had laid it all out there, and even if this was the end of our friendship, at least I could tell myself that I had tried. Neither one of us said anything and the silence stretched on. The dread of her further rejecting me built up, but that didn’t happen. She hadn’t let go of my hand. I started to sense that there was something different happening, but it was hard to put a reason for the feeling. I turned and looked at Miss Walker and she looked back at me. We held each other’s gaze and all of the stress of confessing my feelings for her seemed to start to melt away. I don’t remember consciously thinking about doing it, I would have never tried it if I wasn’t acting on instinct. I leaned over and kissed her. Miss Walker let out a small “mumph” and squeezed my hand. At first, she didn’t kiss me back, but she also didn’t resist the kiss, her lips parting. Her grip on my hand relaxed and she started to kiss me back.
My whole body started to tingle with excitement from having the woman who I had a crush on for years kissing me back. I had only kissed a few girls and they didn’t even compare to how it felt to be kissing Miss Walker. When we finally broke apart, we were both panting.
Miss Walker broke the silence. “We shouldn’t have done that.” I kissed her gently. “This is wrong,” I kissed her gently again. “Ohhhh fuck it,” she said and kissed me deeply. I wasn’t prepared for when she flicked her tongue across my lips Escort Finike and then slid it into my mouth. I did my best to French kiss her back, but I wasn’t used to it and I was feeling so turned on that it was hard for me to keep up with her. I started to kiss up and down her neck, working my way down to her chest. I kissed her cleavage and made her moan.
After kissing and sucking on her neck and cleavage for a few minutes Miss Walker gently guided my lips back up to hers. We kissed deeply one last time and then she pushed me back to my seat.
“We really shouldn’t be doing this… here,” she said, the start of her sentence scared me, but then the end of it gave me hope. “Do you have any plans for tomorrow night?” she asked me.
“Why don’t you meet me at my apartment, there is a costume party my friend invited me to if you want to go with me,” she said. She seemed hesitant as she asked me this.
“Isn’t that a bit risky?” I asked.
“Yeah, but as long as you wear a costume no one will know who you are,” she said.
“Ok.” I did have plans to hang out with my friends, but if they knew the reason why I was canceling on them, they would understand. Of course, I wasn’t going to tell them. Miss Walker gave me her number and we kissed and hugged one last time before I got out of her car. I seemed to float to my room from the euphoria that I was feeling I went straight to my room and jumped onto my bed. I couldn’t believe it, I confessed my feelings for Miss Walker and we had made out, and even more, I had an invitation to go to a party with her on Halloween. I thought about making out with Miss Walker and how much of her tits I had gotten to kiss. I pulled out my throbbing erection and started to jerk off, replying over and over again in my mind the feel and taste of her lips on mine. I was so worked up that I came just a couple of minutes. My cum shot up and landed all over my shirt. I took it off and used it to clean up myself up and then threw it into my hamper.
I lay in bed, going back over tonight and how perfect it had all gone. I had had so much anxiety building up over the years about what would happen once I finally confessed my feelings for her. I had always had fears of how it could go wrong, and fantasies about how it could go right, but it going right had always been thought of just that, as a fantasy because there was no way that an amazing woman like Miss Walker would possibly like me back. Now that I had confessed and it worked out perfectly, I felt like there was a huge weight off of my shoulders.
I looked on my phone at Miss Walker’s number, tangible proof to me that what had just happened hadn’t been some kind of delirious fantasy. I wanted to text her so badly but wondered if that would come off as desperate. In the end, I decided to text her asking if she made it home safely.
She responded saying that yeah, she had and added a smiley face at the end of it.
“I really had fun tonight,” I texted.
“Me too,” she responded. We texted back and forth for the next hour until she said that she was about to fall asleep. It was a little weird texting her for the first time, especially since it didn’t seem like I was texting a teacher, but more like just a girl who I liked. I spent so long putting Miss Walker on a pedestal because she was a full-grown woman and my teacher, that it was going to take some getting used to thinking of her as a person as well. We said our goodnights and she sent me her address with a winky face saying that she would see me tomorrow, I fell asleep with a smile on my face.
I woke up to a good morning text from Miss Walker, no, I had to get used to using her actual name that she had put down in the contact, Melissa. I responded good morning back and we texted throughout the day.
The party was going to start around eight but Melissa wanted me to show up at her house before then. I knocked on her door and waited a couple of minutes for her to open it. My phone buzzed and when I looked at my message from her, she said for me to let myself in. “Have a seat, I’m just finishing getting ready,” Melissa called out from the bathroom.
I took a seat and looked around me. She didn’t have the biggest apartment, but it was well furnished. Along one wall of the living room were three large full bookcases. After a couple of minutes of sitting there, I decided to get up and check out the books. She had a wide variety, there was a lot of the books that we had talked about reading, along with what looked like textbooks from when she was in college on teaching practices. One shelf of the bookcase was nothing but romance books. I pulled one of them from the shelf and looked at the cover, it looked like a typical romance cover with the heroine clutching at the hero’s bare chest and both of them looking longingly at each other.
I heard Melissa walking out of the bathroom. I was going to tease her about her reading choices, but when I turned around and saw her outfit my jaw dropped. She was wearing the Hermione witch outfit that she had worn at school, but this version was much more sex. She was wearing high heels, fishnet stockings her miniskirt barely made it passed her midthigh, and the blazer that she was wearing that had the Gryffindor crest on it was a tight fit and was low cut so that her tits wear barely contained inside of it.
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