Temptations of a Substitute

When I went into teaching, I did so because I genuinely believed that I could make a difference. I had many horrible teachers when I went through school, some that left life scarring marks on me (mentally, not physically). I thought I could be one of those few great teachers that could both teach the material and help the students enjoy life and stay in school. But I never thought I would have the effect I ended up having.

My name is Tom Ryan. I am 27 now, having come back for a teaching degree a couple years after getting my undergrad in mathematics. This following fact may have a lot to do with my experiences: I was not too good in college as an undergrad, spending more time partying, drinking, and sleeping around than I should have, and ended up spending an extra year in college because of that. So when I came back for grad school, I essentially took a temporary vow of celibacy to get through it as fast and well as possible. God knows I jerked off every night (thank God for online porn), but for the two years I was in grad school, I had stopped myself from hooking up with any girls (even over the summer, in fear of ending up in a relationship that would last into the school year), despite some very enticing opportunities. I had also done no partying, and very little drinking. At this point, I thought I was in perfect control of my own desires. What I soon discovered, though, was that man can only withstand so much temptation.

After finishing grad school, I applied for a few jobs, but unfortunately there were very few opportunities, and the ones that arose people were already lined up for. Thus, I ended up going into subbing at various middle and high schools in my area (my teaching range was for grades 7-12 math). I took subbing somewhat seriously. I mean, I would go in and follow the directions the teacher had given me and make sure all work they told me to do was completed, but that was it. And as any sub can tell you, teachers rarely leave behind enough work to last a full period. So, for the remainder of the time, while most subs would come up with some bullshit work for the students to do, I’d kick back and let the students talk amongst themselves, give them such much needed free time that you don’t seem to find in middle and high schools these days. Many times, the class would end up talking to me, and I’d share some of my stories from high school or elsewhere in my life (though never about my partying or drinking or things along those lines). I guess most subs aren’t this personable, and do not give free time to their classes, as I became very well known amongst the students in the schools I subbed for (despite the fact that I was in most these schools less than two days a week). I ended up finding I really liked three schools: a suburban high school, an urban high school, and an urban middle school, amongst which I split up most my time. In all these schools, the students soon stopped calling me Mr. Ryan and just called me Ryan. The students would see me coming in the morning and rush up to see if I was subbing for one of their teachers. I would walk down the hallways and high school kids would come up to me saying things like “Yo Ryan, what’s goin on man?” and “Ryan, you the man!” They constantly reminded me that I was their favorite sub (if not teacher in general).

I never expected this kind of reaction when I got into subbing. I kind of assumed it was because I was not only a laid back teacher, but also a young teacher, who looked even younger. Though I was (and am) 27, I look much younger, often being mistaken for being under 21 when I order drinks. I’m about 6’1” and quite skinny, at about 145 pounds, much of which is muscle from my crew days in college. For whatever reason, I never got fast growing facial hair. I only have to shave every two days, thus never really getting the five o’clock shadows most people equate with men my age. I also had somewhat long hair (for a guy). It wasn’t long enough to pull back into a ponytail or anything, but it was four or five inches long, and I guess people equate men with long hair as being younger for some reason.

Now, it was not unusual for students to drop by whatever classroom I was in for the day when I had a period off to come and say hi and talk for a bit, but it usually did not last long. Usually. But a few times they did. The following being one such time.

I was subbing in the suburban high school for a ninth grade math class. I had to give all the classes a full-period math test, and then keep them all quiet while taking it, so it had been a very long, boring, and highly uneventful day. I had the last period of the day off, but the school would not let subs leave until the end of the day. Luckily, this school has great cushioned chairs for the teachers that roll around and recline. Hence, I had rolled the chair back a bit from the desk, leaned back, put my feet up on the desk, and had just started reading a book. Not soon after I got comfortable, three tenth grade girls came in. This was not unusual, so I didn’t make much of it. They were all students I had subbed for at another time (Amber, Erica, and Emily), and they heard I was in the building so they dropped by. When they walked in the room, they all simultaneously shouted, “Hey Ryan!” They had done this before, apparently they plan out saying it simultaneously.

I looked up and responded, “Hey there! How are you all doing today?”

“We have a study hall right now and nothing to do, so we thought we’d come see you,” replied Amber enthusiastically.

“You don’t have any work to do?” I queried. While we had been talking, the girls pulled up chairs from around the room to the teacher’s desk. Amber and Erica brought seats over and sat on the opposite side of the desk from me, while Emily brought her seat to the side of the desk facing me. I pushed my chair back and a bit to the side so I could see them all at once.

“Of course not, Ryan,” Erica exclaimed while settling down, “It’s a Friday!” The school had an unwritten tradition of not giving out much homework on Fridays, so I easily accepted this story as true. Friday study halls generally were free time, with the students either sticking around and talking in the classroom or getting passes to hang out in the cafeteria or to visit another teacher.

“Oh, so it is,” I said, “I had completely forgotten. Any big plans for the weekend?”

The girls launched into various stories about what they were going to do that weekend. Apparently Amber and Emily were going to have a shopping extravaganza while Erica was being forced to visit her mom’s brother’s family some five hours away for the whole weekend, which she was not too excited about.

While they were all talking, I took in the surrounding scene. Now, teachers can tell you they would never do anything sexual with a student, but that does not mean they do not notice how hot their students are (and if any deny this, they’re lying). I certainly had no plans on doing anything with any of these girls, but that did not mean I couldn’t appreciate their looks, and masturbate to them later (another thing nearly all teachers, male or female do, but rarely, if ever, talk about).

Amber was, from what I could tell in my time at the school, the most popular girl in the tenth grade at this school. She was somewhat tall for a high school girl at, I’m estimating, 5’8”. She was a very skinny girl with her blonde hair pulled back into a ponytail that was purposefully off center. She had gorgeous features – defined cheeks, slightly puffy lips, a small nose, and beautiful green eyes with long lashes and, today, purple eye shadow. She was wearing very tight, low cut jeans and a tight bright purple T-shirt bearing the word “Cheerleader!” across the chest. The shirt fully accentuated her ample bosom, which I can only guess was a 36C. The way she was sitting in her chair, leaning back with her legs out in front of her, it exposed a couple inches of skin between the bottom of her shirt and her jeans, allowing me to see her flat stomach, the purple string of her panties (I’m guessing a thong) coming up her hips, and her pierced navel. I took a mental picture of this, figuring that was going to be the focus of my nightly jackoff that day.

Next to Amber was Erica. Erica was not nearly as attractive. She wasn’t ugly by any stretch of the imagination, but wasn’t a knockout. She was a bit chubbier than Amber, though not what one would call fat, and also a couple inches shorter. She too had blonde hair, with a barrette holding it at the back of her head. Erica had green eyes as well, though of a lighter shade than Amber, and was also wearing purple eye shadow (they had probably passed it around the table at lunch, as they had told me another time that they did that when I questioned why they all had the same color eye shadow on). She had slightly chubby cheeks, but a small mouth with small lips that were unquestionably her best facial feature. She was wearing jeans, but not nearly as tight as Ambers, and was wearing a somewhat loose high-cut white shirt with tiny sleeves. I was guessing that her chest was about a 38C, maybe a 40 though I was hoping not. She was leaning forward in her chair the whole time, so I didn’t get to see much more than that. Though still a pretty girl, she wasn’t making it into my jackoff dreams with Amber looking like she was right next to her.

Finally, sitting at the side of the desk facing me was Emily. Emily also was pretty popular in the school, but not nearly to the level of Amber. I think this was mainly due to her attitude. She wouldn’t pretend to be nice to guys just so that they would like her, something Amber did continuously. She also was very honest, and if you were pissing her off, she’d let you know. However, with that honesty, if she enjoyed being with you, she wasn’t afraid to let that be known either. She also didn’t seem happy very often. She always seemed happy with her friends, but alone she often looked depressed. I never understood why. I can only assume that guys did not like that she would not suck up to them and that she had no problem telling them she didn’t like them, or they didn’t like how she was rarely happy, as those are the only reason I can see for her not being more popular. It certainly had nothing to do with her looks. I mean, damn, was she hot! Possibly more so than Amber. Emily was shorter than the other two, at about 5’3” with long wavy brunette hair that flowed behind her and dark brown eyes to match. Though she was not as skinny as Amber, she was definitely thinner than most girls. And honestly, I thought she looked better than Amber, who was just bordering on being too skinny. It seemed that Emily didn’t have any makeup on today (apparently she didn’t join in on the eye shadow pass-around at lunch), but that just made her more beautiful, knowing that her good looks were completely natural. She was slightly dark skinned, which made her stand out from her two friends, but whether that was because she came from a mixed ethnicity or from heavy tanning, I didn’t know. Erica was very white, while Amber I knew tanned, as she loved to talk about it. Emily had a small, rounded nose and very red lips (which I knew were natural, not lipstick, as I saw her put lipstick on in class when I subbed for her one day to make her lips even more red). Emily had very small dimples at the corner of her mouth, which were only really noticeable when she smiled. Also, when she smiled, it always appeared that her cheeks got this slightly rosy tint to them. I never understood why, but I always loved seeing it. Today, Emily was wearing a tight white skirt that went down to just above her knees and showed off her beautiful, semi-dark legs that ended in casual white shoes covering low-cut socks. On top, she had a white and green striped polo shirt that went down to just over the top of the skirt, which unfortunately gave me no midriff view, which was disappointing as, having seen her baring the midriff before, I knew she had a gorgeous flat stomach, and that she did not have her navel pierced as so many other girls in the school did (which I never was a big fan of). Emily was sitting in her chair with her legs tightly crossed, with her elbows leaning on them looking forward at me, with her beautiful hair thrown over her right shoulder and hanging over her right breast. Now, that hair would have drawn my attention to her right breast, if it wasn’t for the fact that the way she was sitting, combined with the fact that she had not buttoned any of the buttons on the polo shirt, gave me a view straight down her shirt, showing me massive cleavage, and, on occasion when she leaned forward a little too much, the tops of what appeared to be a white bra. And let me tell you, this cleavage was nothing to be scoffed at. Emily was one of the most well-endowed short girls I’d ever seen. If she wasn’t a 34D then she was a damn full 34C. Taking this whole view quickly into my mind, I made sure to capture it perfectly, for she would definitely be in my dreams when I jacked off that night.

While I was taking my mental images of the three girls, they had finished talking about their weekends. They went on to discuss how certain boys were pissing them off, how their global studies teacher was ridiculous and giving them way too much work during the week, talking about upcoming basketball games (Amber, as her shirt said, was a cheerleader, so she was always up on the sporting events), and various other little things. I joined in whenever I could, pointing out that boys can often act immature, that their global studies teacher was probably just doing his best to prepare them for their upcoming midterm (which was a lie, he was just a bad teacher, but I make sure to never talk badly about other teachers in the school), and wished Amber luck cheerleading at Saturday’s game, amongst other things.

At one point during this conversation, Emily happened to uncross and re-cross her legs putting the other leg on top. I had just turned my head, and could swear I saw a brief glimpse of white panties beneath her white skirt. Having been a popular sub for sometime now, I had many girls purposefully give me similar brief glimpses up their skirts, and usually when they did it, they made this innocent smile while staring at me. I always pretended I didn’t notice, as I figured that was the best way to deal with the situation. However, Emily had never done this to me before, so I was a bit surprised. But when I looked up, she was talking to her friends, looking in their direction, so I apparently got an inadvertent glimpse of her panties, which my prick definitely jumped at. Of course, my mind could’ve been playing tricks on me and I might have just seen the inside of her white skirt and nothing more, but I liked to think otherwise. I quickly looked back at the other girls and pretended as though I saw nothing.

About ten minutes after they had first come in, the girls decided they should be heading back to their study hall, so they put their chairs back, I wrote them passes, they said their goodbyes (with the traditional request that I should sub for one of their teachers next time, as if I had control over who I was subbing for), and they headed out of the room. After they left, I leaned back in my chair, put my feet back up on the teacher’s desk, and continued reading my book.

About three minutes later, Emily walked back in the room, alone this time. “Back already?” I asked.

“Amber and Erica have the same study hall, and they went back to theirs,” Emily replied, adding, “my study hall is no fun, so I thought I’d come back here instead.”

In my four months prior experience subbing, I actually never ended up alone in a room with a student, but I figured I knew Emily, so it wasn’t a big deal. “Well, if you want to kill a few more minutes here, that’s fine,” I told her, figuring she’d either leave or I’d kick her out after five minutes, forcing her to go back. Though I didn’t think there’d be a problem having her alone in the room with me, I was more worried about another teacher walking in (which rarely happened, but still possible) and getting the wrong idea, so I thought I would keep it short. Emily pulled up the same chair she had sat in before and took up the exact same position, though she was looking towards the ground now, and looked somewhat sad. “What’s up?” I inquired.

“Uggh,” she began, “boys.”

Not the topic I want to be on with one girl in a classroom, but I’ve talked to her about it before with others around, so I thought there was little harm in it. “I’ve told you a million times, Emily, high school boys are just immature, it’s something you’ll have to deal with. That’s not gonna change much until about your second year of college.”

“I know,” she answered, “but I don’t want to wait that long. I want a mature guy that likes me now.”

“Sorry, Emily,” I replied, “I think that is just something you are going to have to wait on.”

Emily then looked up at me, still with a bit of a frown on her face, and abruptly asked, “Do you think I’m pretty?”

Seeing her sadness I immediately replied, “Of course I think you’re pretty.”

She half smiled at me, then looked back down towards the ground. “You’re just saying that cause you’re a teacher,” she mumbled.

“No I’m not,” I defended, “In fact, it is because I’m a teacher that I shouldn’t have said that.”

Emily looked up at me, still frowning, but raised one eyebrow and asked “And why is that?”

“You see,” and I stopped talking for a second to dig through the folder of instructions given to every sub every time they come in and pulled out the regulations sheet and handed it to Emily. “The second rule for subs here says I should avoid controversial topics with students, which this most definitely is.”

Emily took the sheet and started to read it while asking “Why is it controversial?”

“Let’s just say if another teacher walked in and I was telling a female student she was beautiful, I could get in a lot of trouble,” I replied, starting to get uncomfortable with the path of the discussion.

Emily suddenly looked up and smiled when I said that, and asked “So you think I’m beautiful then? Not just pretty?”

Shit, I thought, dug myself that hole, didn’t I? I sighed, then looked to the open door on the other side of the room, saw a clear hallway, and replied, “Yes Emily, I think you are beautiful. Now I think we need to stop having this discussion and you should go back to your study hall before we get in any trouble.”

Emily smiled and looked back at the sheet. “You wouldn’t get in much trouble – at least we’re not breaking rule number one,” she said. Then, looking up at me and smiling a full smile that made her cheeks turn rosy, coyly added, “Unless of course you want to….”

Fuck! This hot sixteen year old student was coming onto me! I was in shock for a second, not knowing what to say. Obviously, I wanted this in theory, but I didn’t want the ramifications of getting caught. I had to lean towards the latter. “Alright, Emily,” I began in as calm a voice as I could maintain while looking her directly in the eyes, “that crossed the line. You need to get up and go back to your classroom. The door is wide open and someone could come in at any point in time, and then we’d both get in trouble. This needs to stop before that happens.”

Emily’s face straightened for a bit, and then she smiled. She put the sheet on the teacher’s deak, got up, put her chair back, and started walking to the door.