Editor note: 1st time. storyline based off true events with embellishments.
Ms K
My senior year of high school was less than typical. I enjoyed the success and popularity of being a star athlete and everything that came with it. I was a good looking kid with a quick sense of humor and commanded my fair share of respect around town which led to a fair amount of girls losing their clothes around me. I rarely ever wanted for anything. My teachers were all fond of me and did their due diligence to keep me eligible even though I put very little effort into schoolwork. One teacher specifically took a special interest in my work and eventually time outside of school. Ms. K was my journalism teacher.
She was attractive for a teacher of that era and enjoyed her students having fun in her classes. We learned and put in the work but she made sure the environment was always joyful and positive. I've always been a good storyteller so it was a class decision to install me as the "editor" of our school paper which was basically our entire coursework for the year. I enjoyed the "job" but did as little work as I could get away with. As the school paper editor I worked closely with Ms. K on the final decisions before the weekly news went to print. The first time I noticed Ms. K in a sexual way and not just my teacher was when my football coach who was also my math teacher told me in the locker room before practice that she needed to see me.
"Go see Ms. K, she says there's an issue with your paper going to print in the morning Mr. Editor" he joked. "Hurry up and then get to practice." "
"What seems to be the problem with my newspaper, boss" I said strolling into her room.
"Well, I can see you're ready to save the day" she said mocking me in my football pants and sleeveless shirt.
"I come prepared for anything". I said.
As I leaned beside her with our hands on the desk studying the layout, I couldn't help but notice I could see directly down her blouse with a perfect view of her bra and tits. They weren't big but on her small frame were more than adequate. My 18 year old hormones reacted accordingly. After staring for what seemed like minutes I averted my eyes and found Ms. K looking directly at me.
"Umm, a little more focus on the problem at hand" she said directing my eyes back to the paper.
I felt embarrassed but her reaction left me at ease. What was happening in my football pants was anything but at ease. After a few changes and an agreed upon solution I said I better get to practice. As I turned awkwardly towards the door trying to hide the obvious bulge in my tight pants Ms. K said, "I thought you guys wore protective cups or something like that."
Weirdly, I felt a little emboldened knowing that she had looked as well.
"I don't, too restrictive and uncomfortable."
"Well, have a good practice. Thanks for responding so quickly." she said taking one more quick glance at my obvious hard on.
For the next couple weeks there was a subtle change in how we interacted with each other. Nothing blatant enough to the naked eye but different. From my desk at the edge of the room I could see somewhat behind the teachers desk. Never crossed my mind or drew much attention until the day I was spacing off and caught an eyeful of Ms. K's nylon clad legs. Now, her dress wasn't pulled up inappropriately but I caught a glimpse of her shapely upper thighs. I couldn't help but stare. She always wore stockings and knee length dresses but now these small details were catching my eye. She had great legs and as I found out later, stockings are my Achilles heal. Once again she caught me looking although this time after our eyes met I returned my gaze to her beautiful legs. She watched me watch her and then crossed her legs inching her skirt up just high enough to expose the bottom hem of her thigh high stockings. I almost came right then and there. This game continued for a couple weeks until I decided to instigate a little myself. It was Thursday of homecoming week and as the rest of my classmates were finishing up the paper for the next day I was up at Ms. K's desk going over the layout of tomorrow's article. I couldn't help but focus on the sexy legs wrapped in nude stockings tucked safely behind her desk. I wasn't even trying to hide my intentions and neither was my throbbing cock which was directly at her eye level.
Ms. K quietly said " you should probably go sit at your desk before somebody notices your issue" motioning her eyes to my bulging crotch.
Now for the record I'm no John Holmes but I'm above average at 7" long and 4.5" circumference. On a 165 pound high school kid it was definitely noticeable. I avoided being noticed and sat down at my desk. As I did I reached down and tried to adjust it for comfort making eye contact with Ms. K. She didn't take her eyes off my cock and my adjusting turned to stroking over my jeans. This went on for a minute or two and was a major turn on for me. When I couldn't take anymore I asked to use the bathroom and jerked off to the thought of Ms. K watching me stroke my rock hard cock. I couldn't stop thinking about it for the rest of the day.
We won our homecoming game on Friday and our school dance was Saturday night. A few guys and I were going stag so we could keep our options open and proceeded to get a few drinks in before it started. It was relatively lame like most school functions but we had plenty to look at. I saw Ms. K across the room with a man who looked to be her date. I knew the guy and didn't think much of him. We made eye contact a few times but I kept my distance for a couple reasons but mainly because I had been drinking. I came face to face with Ms. K leaving the bathroom.
"Great game last night, really proud of our editor!" She joked.
"It was a tough game" I said "not sure I've ever been this sore after a game."
"Nothing that a few beers won't fix" she said winking at me.
I played the old "who me" game but could tell she knew.
"Don't worry, I'm not going to tell. I've had a few myself tonight."
"Don't you know it's against the rules to be drinking on school property?" I said coyly, feeling a little more confident.
"What they don't know doesn't hurt them. Matter of fact I have a couple left over from earlier in my office. You and your friends can have them if you're careful."
"Hell yes we'll take them!" I said quietly.
"Follow me and try not to be seen."
I let Ms. K go first and a couple minutes later I followed her back to her room.
"Thanks, I think I can set them outside the side door and we can pick them up when we leave. You're the best teacher at this school."
After an awkward silence and maybe with help from the alcohol we kissed. We were both in disbelief. "I'm sorry, I shouldn't have done that". She said
"I'm not. Can I try it again?" I asked
This time it was full on make out session. Tongues, hands, you name it. At one point I slid my hand down over her ass and down her hip and could feel the top of her stocking. I tried pulling up her dress to feel the stocking first hand but she pulled away.
"I can't believe I'm doing this and on school property no less."
"It's kinda fun" I said jokingly.
"You better get back to your friends" she said with concern.
I then took my shot. "I'll leave after you show me those sexy legs and stockings"
"Are you crazy?" she said with a little grin.
"Yes. Show them to me"
It was then under the red glow of the hallway exit sign that she lifted her skirt up to her waist giving me a clear view of her beautiful stocking covered legs and panties. I couldn't help but stare.
"Ok, that's enough." She said dropping her skirt and smiling. "You owe me one."
"I don't like owing people" and with that I unzipped my pants and showed her my throbbing cock concealed in my underwear.
"See what you do to me Ms. K." I said while stroking my cock through my underwear.
Ms. K didn't say anything. She was completely focused on my hand stroking up and down on my cock.