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. I let out a sigh of relief that things were going to end so easily. But before I had even finished that sigh, I heard the door shut quietly, and saw the lights go out. I looked up and stared as Emily, having shut the door (which locks automatically when closed) and shut off the lights, walked back towards me. I was in a state of shock. She stopped directly in front of me, and I just stared at her in shock with my mouth half open, not knowing what to say. She proceeded to grab the arms of the chair I was sitting in, and rolled me a few feet towards the wall next to the teacher’s desk. This wall was the same wall that had the door, though the door was on the other side of the room, so she had dragged me to a place where we could not see into the hall, and no one from the hall could see in. Also, as this classroom was on the second floor, no one could see in through the windows, which the blinds half covered anyhow, making for dim but clear lighting.
As Emily stopped moving my chair, she stepped right up to the foot of the chair, and then, without warning, straddled me, with one leg over each arm of the chair. She then put her hands on my shoulders, and, stared directly into my eyes. The feeling of her legs across mine, her hands on my shoulders, her eyes looking deep into my own, it was completely electric. I was frozen in place and could not move. After a few seconds like this, she began whispering to me, “Okay. Now the door is locked and the lights are off. No one is going to come in, and anyone wondering where you are will look in, see an empty classroom, and assume you went to the faculty room. There is no chance of us getting caught, so neither of us will get in trouble. So again, do you want to, or want me to, break rule number one?”
Holy fuck! This was like my nightly jackoff dreams come true! One of the, if not the hottest student I had ever taught was trying to seduce me. But it was still wrong! She was absolutely right, no one would ever know besides her and me. Anyone who came to the door would assume I had gone to the faculty lounge, as most teachers do with their periods off. The only reason I don’t is because I know students like to drop by and say hi, and I like to give them that chance. Well, things had definitely gone differently this time. So I knew we wouldn’t get caught, no one could see us from the door and no one could see through the window, but did that make it okay? I mean, she’s 16 for God’s sake! She’s my student! It’s illegal! It’s immoral! I mean, it’s one thing to jackoff to girls like her, but then I’m not really doing anything to her, no harm no foul. But this – this was something completely different. I knew I shouldn’t be doing this.
“Emily,” I began, “we can’t–”
But she cut me off. She put one finger to my lips to quiet me, which worked perfectly. “We can,” she said, smiling. That smile was killing me. It wasn’t a slutty “fuck me” smile, like some girls are known to do to get their way. It wasn’t the innocent smile where girls pretended they didn’t know the effect they were having. No, this smile was genuine. It was a smile of pure happiness. I had never seen Emily look happier. She moved her face closer to mine, her lips were only a couple inches away from mine. “We can,” she repeated, “we can do whatever we want. The question is what do you want?”
She removed her finger from my lips. I was frozen. I was fighting with all my might against her, but she was breaking down my barriers like they were butter. Add to the fact that I had not had any sexual relations since before grad school, which made me abstinent for about three years until this point. My body wanted this. Emily clearly wanted this. But my mind was still trying to tell me it was wrong.
“Emily,” I sighed. I broke her gaze and looked down at her legs spread over mine. I took a deep breath, and, determined to try one more time to stop this, continued. “Emily,” I repeated, “you are beautiful. One of the most beautiful girls in this school. You are a genuinely honest and good person. If you were my age, or I yours, there is nothing I would want more than for this to happen. But that’s not the case. I’m too old for you. This illegal. It’s wrong. We can’t do this.”
Emily’s smile just seemed to get wider. A couple tears went down each side of her face. I had meant those comments to console her while hopefully ending the situation. Instead, it seemed she had taken the comments to heart, and it just furthered her drive to get me. She suddenly lunged forward, wrapping her arms around my head and hugging my head tight into her neck, which forced my chin into her cleavage. “Oh, Ryan,” she whispered directly into my ear, “It’s only illegal if we get caught. And how can it be wrong if we both want it so much?”
Shit. I felt my last shred of resistance snap like a twig. She had me. I hadn’t felt a girl’s touch like this in three years. And I hadn’t had a girl’s touch with such love and care in it in at least six. She was right. I wanted this. I wanted it bad. In fact, at that moment in time, there was nothing I wanted more in the entire world.
“Oh, Emily,” I whispered back into her ear, and for the first time since she had turned the lights off, I moved. I reached around and hugged her tight against me.
While I wanted to continue hugging her like this, she pulled back almost immediately from when I hugged her and looked straight into my eyes. At first I was worried that I had done something wrong. But then she asked, a couple tears of happiness continuing to roll down her face, “So we can do this?”
“Emily,” I replied as I took one hand and wiped the tears away from her face, “we can do whatever you want.”
The dam broke as tears started streaming down her face. She again lunged forward and embraced my head again, which I gratefully returned, gently and slowly rubbing my hands around her back. She whispered in my ear, “Thank you, Mr. Ryan.”
I found it odd that Emily called me Mr. Ryan right then, as she normally just called me Ryan, but I pushed it out of my mind. “You’re welcome, Emily,” I whispered back, hugging her tight to me again. This time we stayed in the embrace for awhile, listening to and feeling each other’s breathing.
After a minute or so, Emily pulled back. I let my hands slide from her back to her sides, just above her hips. She slowly slid her hands from the back of my neck, over my shoulders, and onto my chest, avoiding my subbing nametag that was clipped to my shirt pocket. She kept her hands on my chest for a bit while I lightly squeezed her sides. Then her hands slid up, one hand reached inside my knot tie, and she pulled outwards, loosening it, but not undoing it. When it was quite loose, she grabbed the sides around my neck, and with both arms, pulled the tie up over my head. I thought she was just going to throw it to the side, but instead she put it over her own head. She then asked, “How does it look?” while putting her hands on her hips and faking her best serious face.
I couldn’t help myself, and let out a light laugh. “Emily, I don’t think that tie has ever looked better.”
She smiled again, looking deep into my eyes. Slowly, her gaze moved down, and her hands returned to my chest. I looked down and watched as this beautiful girl’s small hands started unbuttoning my shirt from the top down. When she was done, I leaned forward on the chair, putting my head on her shoulder, and she pulled the bottom of the shirt out of my pants. I then leaned back and unbuttoned the cuffs of the sleeves while she ran her hands around my chest over my tank top undershirt. I pulled my left arm through the sleeve, and leaned forward again, letting Emily pull the rest of the shirt off my right arm and toss it on the floor. She then pulled my left arm towards her, and loosened my wristwatch and slid it off my hand, lightly dropping it on top of my shirt. Finally, Emily reached down and pulled my undershirt out of my pants. Holding onto the bottom of it, she looked at me and said “Arms up!”
I smiled at her, raising one eyebrow, and raised my arms above my head as she pulled the undershirt off over me, dropping it on the floor with my shirt. After that was done, she pulled back and looked me over for a few seconds. Then her eyes met mine, and she threw her arms up in the air and exclaimed, “Your turn!”
Without saying a word, I put my hands on her side again. I was about to grab the edges of the shirt, when I realized she was still wearing my tie. Not wanting to take the tie off of her yet, I slid my hands up over the front of her shirt, feeling her breasts for the first time (which was amazing – they were more firm than I ever could have imagined!), and got to the tie. I reached around the collar of her polo shirt, and tucked the neck of the tie inside, then, getting to the front, tucked the front of the tie down the front, briefly brushing the bare top of her breasts. Her arm’s still up in the air, Emily giggled and closed her eyes. I finally reached down and, grabbing the bottom of her shirt, slowly pulled it up, over her beautiful stomach, over her large chest (revealing a white lace bra), and then over her head and off her arms, dropping it on top of my shirts. She put her arms down and I took the moment to absorb the look of this gorgeous 16 year old on my lap, wearing just an incredibly sexy white lace bra and my tie on her upper body. I noticed that Emily’s hard nipples were poking out her bra. They appeared to be poking out nearly half an inch! I always had a thing for long hard nipples, so this just increased my desire for the girl. While looking her over, I ran my hands from her sides, onto her stomach, lingering for awhile on her breasts, and finally up her neck and onto the sides of her head. When me eyes finally met hers again, she asked, “Can you get my bra off, or should I?”
I hadn’t unhooked a girl’s bra in quite some time, but I used to be quite adept at it. Not wanting to risk looking stupid, I told her, “I’d love to, but I’ll need to see what I’m doing.” She smiled at me, apparently catching my drift, and leaned forward resting her head against my shoulder and reaching her arms around me, hugging me underneath my own arms. From here, I could see clearly down her back. I gently cupped Emily’s breasts beneath me, and slowly slid my hands along the sides of her bra until they met at the hook in the back. While I was doing this, Emily had started lightly kissing my neck. The feeling was amazing, and I briefly got distracted. Getting back to my mission, I flipped the hook of the bra up so I could see it better, and found that the tag was right next to the hook. Curious, I flipped over enough of the bra to fully see the tag. 34DD! I knew she was big, and having taken off the shirt knew they were bigger than I had initially thought, but DD never even crossed my mind! I got back to the hook and gently unhooked the bra. I reached up and pulled the shoulder straps towards me. As I did this, Emily stopped kissing my neck, and slowly backed up, letting me continuously pull the bra towards me while she backed out of it. The tie got pulled up and over her bra, falling back down against her naked chest. The bra came off her hands, and she dropped her arms to her side, staring at me. When the bra came off her arms, I got my first full glimpse of her bare breasts with my tie caught between them, at which point I accidentally whispered aloud, “Good lord!”
Emily, misinterpreting my meaning, frowned and worriedly asked, “What’s wrong?”
I looked up at her face, smiled, and told her, “Nothing is wrong Emily. I’ve just never seen such perfect breasts in all my life!” She immediately smiled again, with her cheeks becoming very red, apparently slightly embarrassed. I looked back down at her chest. “They are beautiful,” I continued, while bringing my hands up to cup them from the bottom. “Their color, just dark enough is incredible. They’re so firm, but soft, and they stand straight out.” I started rubbing my thumbs over her nipples. “And these nipples! Slightly darker than the skin, so hard, so big!” And they were big, the areolas were about an inch and a half in diameter, with the nipple itself being about half an inch in diameter but sticking out what must have been damn close to three-quarters of an inch, maybe more. I gently flicked them and watched them come back to full attention. I was in heaven. “In my wildest dreams, I never thought such amazing breasts ever existed,” I told her.
“I’m so glad you like them!” Emily exclaimed, adding, “I was always worried they were too dark and too big.”
I looked up into her eyes. “You should never worry about that! They truly are the most beautiful things I have ever seen in my life, and anyone that thinks otherwise, well, that’s there loss,” I whispered to her, genuinely meaning every word of it. She gave me her now famous smile again, and I looked back down at her breasts. I realized I found them all the more appealing with my tie lying between them. Suddenly I felt her hands on the back of my head pulling me forward. I briefly resisted and looked up at her. I raised my eyebrows at her, as if to say “are you sure?” Apparently catching my meaning, she nodded and pulled my head towards her chest again, more forcefully. This time, I did not resist.
Emily pulled my head into her right breast. She was clearly aiming my mouth for her nipple, which I desperately wanted to do, but I also wanted to heighten her pleasure. So while she was pulling me in, I twisted my head a bit to the left, so that she ended up pulling me to the outside of her breast. I began gently kissing in circles around her breast, starting on the outside and tightening the circles each time. I could hear Emily lightly moaning above me, and she started running her hands through my hair. When the circles became so tight that I was kissing part of her areola, I pulled my head back a tiny bit, gave her nipple a brief flick with my tongue, eliciting a more distinctive moan from Emily, and rather than continuing, started kissing my way over to her left breast, lifting the tie behind my head, and began the same process on her left breast. By the time I was closing in on her left nipple, her anticipation and arousal must have been incredibly high as she was now tightening her grip on my head, shaking lightly, and breathing so heavily that it seemed like she was thrusting back and forth with her chest. I decided it was time to stop teasing her and give her what she wanted. I closed my mouth around her left nipple.
As soon as my mouth closed around her nipple, Emily gave a somewhat loud moan. I pulled back immediately and looked up at Emily. As soon as I pulled my head off her nipple she had stared down at me wondering why I had stopped, though she was still breathing in gasps.
“You have to stay quiet,” I reminded her, “remember, we can’t get caught.”
“Sorry, Mr. Ryan,” Emily panted with a smirk on her face, “I’ll stay quiet in class, I promise. That was just so good, I couldn’t hold back.”
I smirked back at her, treating me like the teacher, and said, “I’m glad you enjoyed it, but we need to stay quiet, even when it’s good, and if you can, I promise I’ll give you even better!”
Emily smiled back at me and raised one eyebrow, responding, “Oh will you? Well, I guess I’ll have to stay quiet to find out.”
This girl was killing me. Every time I thought I couldn’t want her any more, she did something to make me want her more. I smiled back at her after this last comment, returning the single raised eyebrow. Then, without saying a word, I lowered my head to her right nipple and began sucking it for all it was worth. Emily gasped above me, but kept quiet.
I continued sucking on her nipple, lightly running circles around it with my tongue, and occasionally flicking it, eliciting a quiet gasp every time. After what seemed like an eternity (but was probably only a minute or two), I kissed my way back across her chest to her left nipple, again sweeping my tie aside, and repeated the process. Soon after I started on her left nipple, I felt Emily start lightly thrusting her hips on my legs. I don’t think she realized she was doing this, she was just so clearly lost in pleasure the action was subconscious. I took this as a sign to move on. I left her nipple, and kissed my way up from her nipple, over my tie, up her neck, and lightly nibbled on her ear. I started kissing my way back to her mouth. When I was about to kiss her mouth, she pulled back. I pulled back as well and looked up at her wondering what was wrong. Still breathing heavy, Emily smiled and put her finger on my lips and whispered, “Not yet.”
I wasn’t sure why she didn’t want me to kiss her on the mouth, but I didn’t have much time to think about it. Emily backed up off of me standing up, grabbing my hands as she went. She then pulled me up off the chair, which sent the chair rolling a couple feet backwards behind me. I was now standing up right in front of her, standing about ten inches over her. I had never realized how short she really was until we were this close.
I was staring down at Emily, but she was not looking at me. Rather, she was staring at my torso. She slowly slid her hands up from my hands over my bare arms and onto my chest. She started lightly running her nails back and forth through the hair on my chest. My nipples responded quickly, becoming just as hard (though much smaller), than hers were. Emily didn’t fail to notice this, and flicked each nipple with her fingers, making it my turn to let out a quiet moan. After doing this, she slowly slid her hands lower, and lowered her own body as well, eventually sinking to her knees in front of me with her hands on the top of my pants. She leaned forward, and gently kissed around my stomach, and started to unbuckle my belt. After she unbuckled my pants, she pulled her head back and stared at the crotch of my pants. I was staring down, unable to take my eyes off of her. She then unzipped my pants and was starting to unbutton the pants. I could feel my hard-on straining against the button of my pants, and knew this next step was going to be interesting. Sure enough, as soon as she unbuttoned my pants, my boxer-covered prick flicked out a few inches nearly hitting Emily in the face, which she was clearly not expecting. She let go of my pants, jumped back and gasped. This caused my pants to fall down to my ankles. Emily looked up at this point with a look of surprise on her face. I was looking down at her smiling, and when she looked up, I just cocked my head to the side and shrugged. Emily smiled back at me, followed with the now infamous one eyebrow raise, and then directed her attention down again.
Emily grabbed my hips through my boxers, with her fingertips just brazing my ass. She looked down and saw my pants, and proceeded to slide her hands down over my legs to my feet, not taking the boxers with her. She then untied each of my shoes, and, pulling each leg up (I caught on and lifted my own leg), took off first one shoe, sock, and pant leg, and then repeated the process with the other leg. When she was done, she tossed the shoes, socks, and pants onto the pile of other clothes, which was a little behind me. I looked down and again assessed my situation. Here I was, a 27 year old substitute teacher, standing with just my boxers on (not to mention the hard-on I had straining against those boxers!) with the most beautiful 16 year old girl I had ever seen kneeling topless in front of me, her face mere inches from my raging prick. The thought that this was wrong had long since disappeared from my mind.
Emily brought her hands to my boxers again. She reached around the front and traced the outline of my prick against my boxers. The feeling was incredible! I knew it was coming, but I still jumped, as nothing could prepare me for her sensual touch. She seemed to do this for awhile, apparently intrigued with it. I was guessing this was because it was probably larger than any she had seen before, as I’m a little longer than 7 1/2 inches long, which is longer than most high school students. My prick is also about 1 3/4 inches in diameter, making it thicker than most high school students as well. Eventually Emily grabbed the sides of my boxers, and started to slide them down. As she was doing this, my prick head got caught by the elastic band on the boxers and was being pulled down with it. When she had my boxers below my ass in back and just showing the base of my prick in front (as it was pulled nearly perfectly downward, which was getting me hornier by the second), Emily suddenly looked up at me and exclaimed, “You’re shaved!”
It was true. Since I was 21, I found that I had enjoyed the feeling of shaving off all my pubes, and found that, for the few years after that that I had sexual encounters, girls seemed to enjoy it better as well. As such, I got into the habit of shaving downstairs twice a week, even when I had stopped hooking up with girls. I had happened to shave the night before, so I was perfectly smooth down there for Emily. I just looked down at Emily smiled, and raised one eyebrow. Emily laughed in response and looked back down and began pulling my boxers down again. My prick was still caught by the band, which Emily must’ve noticed, but apparently she misestimated either how long it was or how far she was from it, because as soon as my prick got free from my boxers, it snapped upwards and hit Emily in the chin, snapping closed her slightly open mouth. She had a look of complete surprise on her face, to which I couldn’t help but laugh at. When she looked up at me, Emily started laughing to. After some ten or twenty seconds of laughing, Emily grabbed my prick and kissed the head, which caused me to immediately shut up. She heard my immediate quiet, and looked up at me and smiled, then let go of my prick and pulled my boxers all the way down with both hands. I stepped out of them and she tossed them aside and raised her face back up to the level of my prick.
I watched as Emily just stared at my prick for a bit, apparently wondering what to do next. I didn’t want to force her to do anything, so I just stood there waiting. I didn’t have to wait long. With her right hand, Emily grabbed my prick while reaching around and rubbing her left hand around my ass. She then leaned forward and, moving my prick out of the way, started kissing the area above my prick where my pubes would have been. She then circled around one side to kiss and lightly tongue my shaved balls, then went up the other side. She repeated this circle around my prick, making a smaller circle each time, always moving my prick out of the way. I was simultaneously in heaven, with the feeling of it all, and hell, dying for her to kiss and lick my prick. I guess this was punishment for what I did to her breasts!
By the time Emily began kissing up my shaft, I could feel my prick pulsing in her hand and beneath her lips. I was breathing in quick gasps, which she must’ve been able to hear. She kissed up and down both sides of the shaft, avoiding the head, then began licking all around the shaft, slowly moving up towards the head. When her tongue first flicked the head of my prick, I had to suck in my breath, grit my teeth and close my eyes to fight not to cum right there. I wanted this to last longer, but this girl was quickly wearing me out! After holding back for a bit, I felt I was safe and opened my eyes to look back down at her. As I did, she pulled her head back and kissed the tip of my dick, lightly running the length of my piss slit with her tongue. I started quietly moaning. As she did this, she slowly slipped more and more of my prick in her mouth until she had the first four inches in. Then she slowly pulled her mouth off my prick, dragging her lips along my prick as she went. The feeling was incredible, I was holding my breath the whole time, and I felt myself getting close to the edge again. Luckily, when she got to the end and pulled her head off, she looked up at me, smiled, and started to stand up again, kissing up my body as she went. While this might have killed me in another situation, given I was so close to cumming, I was actually really happy she stopped when she did. It gave me a chance to cool down, which I needed as I wanted to do so much more!
When Emily got to my neck, she kissed it a couple times, then pulled back and smiled at me. While I was looking at her, she reached down to her skirt and unzipped the back. As she did that, I grabbed the sides of it. I think she was planning on letting it fall down her legs, but I had other plans. Getting a glance of surprise, followed by a smirk from Emily, I began pulling her tight skirt up her body. She raised her arms and I pulled the skirt up her torso. I had a bit of trouble getting the skirt around her large breasts, which led to some giggling from Emily. I ended up having to go over each breast one at a time, and carefully pull my tie through to make sure it didn’t come off with the skirt. I then pulled the skirt over her head and arms, and tossed it with the rest of the clothes.
When I finally looked down again, I saw Emily in low cut white lace panties that matched her bra. I briefly wished I had been able to see Emily in the matching lingerie, but realized I didn’t want to cover her beautiful breasts ever again. It was my turn to kneel. I got on my knees in front of Emily, and untied and removed her shoes and socks, with her lifting each leg for help. Then, I reached up to her lace panties, the only article remaining between the two of us, save for my tie that she was wearing. I reached around and felt her ass through her panties. She briefly shuddered, and I looked up to see her head looking at the ceiling. I slowly slid my hands around to the front, tracing a finger down the line where I could feel her slit through the panties. This caused Emily’s whole body to shake and jerk back and forth briefly, as well as cause multiple gasps that I could hear. At first I was wondering if I had given her an orgasm that easily, but it ended too quickly. I figured she was just extremely aroused and thus sensitive.
I finally grabbed the sides of Emily’s panties and began pulling them down her legs. I watched as they revealed a neatly shaven strip of hair above her slit, while the slit itself was completely bare. Her outer lips also hid all of the insides of her pussy. I loved pussies like that, no skin sticking out between the lips, just true slits. Unfortunately, I hadn’t seen one like that since my second year of college – eight long years ago. I felt my prick jerk up a bit while I looked at her slit. I paused with her panties around her thighs and looked up at Emily and said, “Looks like someone else here shaves!”
Emily looked down at me, smiled, and just raised a single eyebrow. I laughed at her reciprocity, which caused her to laugh as well. I looked back down, and pulled her white lace panties down to her ankles, letting Emily step out of them. I tossed the panties aside, then grabbed her ankles, and slowly slid my hands up her smooth legs. When I got to her thighs, I reached around and brought my hands up the back of her thighs to her ass. I leaned in and started kissing up the insides of her thighs, switching back and forth between sides. This led to light moaning from Emily. As I got to her slit, I briefly licked from the bottom of her slit up, lightly pushing inside and feeling the skin in there. Emily violently gasped and her body shook again. I thought she must be on fire to be that sensitive! I was about to lean back in and delve deeper into her slit, but Emily grabbed my head and stopped me.
“Not now,” she said. I couldn’t hide my disappointment. This was something I was highly looking forward to. I loved to eat pussy, and had not done so in over three years, and here, I had the chance to, and I was being held back. My disappointment must’ve been obvious to Emily, as she said “Sorry, I can’t stay quiet if you do that. But here…” As she finished saying that, Emily knelt down and laid back on the floor, spreading her legs slightly and putting her arms above her head, her incredible breasts drifting slightly to their respective sides, but still standing up pretty firmly. She lifted her head up slightly, looking at me kneeling before her beautiful exposed naked body. She smiled at me, and then looked very serious, whispering quietly, so I could barely hear it, “Make love to me Mr. Ryan.”
I continue to look on in awe at the sight before me. I figured I must be the luckiest man alive, to have this slightly dark-skinned young goddess laying on the ground in front of me, asking for me to make love to her. I slowly soaked in every detail of this image – her beautiful brunette hair spread out on the floor around her head, her arms raised above her head, the look of sincere desire on her face, her rosy cheeks, her beautiful breasts that, though slightly off to each side, still appeared nearly unnaturally firm, the slight sink from her ribcage down to her navel, the small brunette stripe of hair above her slit, her smoothly shaven slit that was slightly open showing a hint of pink with her legs spread as they were, her defined and smooth legs spread out awaiting me to come between them. It was an image I will remember for the rest of my life.
Somewhere in the back of my mind, I felt like I should make sure that Emily truly wanted to go through with this, having sex with a teacher, but I felt we had gone too far to turn back now, and I was going to be damned if I was going to ruin this moment by asking if it was okay.
I moved my knees forward and leaned over, and slowly let my body weight fall against hers, feeling my prick settle along the line of hair above her slit. I leaned down to kiss Emily on the mouth, but she brought up her hand, and put a finger to my lips to stop me again. “Not yet,” she whispered, quite seductively. I didn’t understand this girl, I was about to make love to her, but she wouldn’t let me kiss her? I tried to let that go and move on. I held my upper body up with my arms, gazing into Emily’s beautiful face. She moved her arms behind my head, held onto the back of my neck, and looking me squarely in the eyes, simply said, “Do it.”
I needed no further encouragement. I lifted my lower body slightly and put my upper body weight on my left arm. With my right hand, I gently stroked Emily’s cheek, which caused her to moan quietly and close her eyes. I gently slid my hand down her neck, and then followed the path of my tie down her body, reaching her strip of hair and simultaneously my prick. I grabbed my prick, slid my body a bit lower, and rubbed the head of my prick through her slit. Both Emily’s body and mine shook as the head of my prick brushed by her wet clit. As I dragged it slightly lower, I aimed it directly into her hole, putting the head barely in so that my prick would stay there without my holding it. I brought my hand back up and used both arms again to hold my upper body up. As much as I just wanted to continue, I had to know something first. “Emily?” I asked, causing her to open her eyes, “Are you on the pill?”
“For nearly six months now,” she answered, under her breath, closing her eyes again, apparently enjoying the feeling of my on top of her.
I continued staring at Emily’s beautiful face, her eyes still closed. I whispered, “Ready?” Keeping her eyes closed, Emily just nodded in approval.
I slowly pushed in with my hips, entering Emily. She immediately began moaning. She was incredibly tight! I only had the head in, and my prick felt like it was entering a smooth vice grip! I had felt nothing like it ever before. If she was not so wet, I don’t know if I would have been able to get in her. I closed my eyes, thinking of nothing but the sensation, and continued to slowly push into her. As I did, I heard Emily start gasping, and opened my eyes to look at her again. Her eyes were closed, and she was biting her lower lip, apparently trying to keep quiet. The scene just aroused me more. I kept pushing in, but started to feel resistance. I didn’t think I could have filled her up already! I looked down, and saw that my prick was only about two inches into her. I tried to push lightly again, and heard Emily gasp again. Then it clicked – she was a virgin!
Emily was a virgin, and I had my prick right up against her hymen. I looked back up at her face. She was still biting her lip, but her eyes were now open, looking deeply into my own. I couldn’t hold back my surprise. “You’re a virgin!” I exclaimed. She just nodded, still biting her lip. My mind freaked out. I had never taken a girl’s virginity before! I lost my own when I was 16 to a girl who had had sex before me, and no partner I had since had ever been a virgin. I suddenly realized I was about to taken a 16 year old’s virginity – when I was 27. The wrongness of the situation crept back into my mind. “Are you sure you want to do this?” I suddenly asked.
“Oh god, yes,” she quickly shot back, a little louder than I expected. I could tell not only by the way that she said it, but also by the way she was staring into my eyes, that she was telling the truth. I made up my mind – this girl wanted me to make love to her, and I certainly wanted it, so I was going to take her virginity, despite the back of my mind telling me I shouldn’t.
I pulled out about an inch, so just my head was left inside her and whispered, “This might hurt a bit.” She nodded her head while staring at me, closed her eyes, and bit her lip again. I tightened up my lower body, preparing to shove my prick through her hymen and as deep in as it would go. I pulled back a little bit and –
“I can’t do it,” I suddenly told her. She opened her eyes, as my body untensed. I couldn’t do it. I just couldn’t bare hurting this innocent girl and taking away her virginity.
“Why not?” she replied, suddenly on the verge of tears. “I want this, I want you!”
“I’m sorry, Emily,” I replied, “I just can’t make myself hurt you.” A couple tears flowed down her face as she closed her eyes. I didn’t want to make her cry, but I also knew I couldn’t plow through her hymen. The solution suddenly came to me. “You have to do it.”
Emily opened her eyes again and asked, “What?”
“I can’t bring myself to hurt you, but if you want this, then you’ll have to be the one that breaks your hymen on me, not me breaking it for you,” I replied.
Her tears appeared to slow, and she smiled again, making her already flushed cheeks even redder. “How should I do that?”
“We’ll roll over,” I answered, smiling back at her. “I’ll lie on my back, and you can get on top of me, and bring yourself down on me whenever you’re ready.”
Emily giggled a bit, why I’m not sure. “Okay,” she whispered back.
I smiled, and pulled out of her. Emily started to sit up and moved to the side. I laid down on my side facing her, and rolled onto my back. Emily spread one leg to the other side of my hips, grabbed my prick, and, just as I did before, put just the top of the head in her slit so that she could let go of it and it would stay in place. I stared up at her beautiful body, her stomach, her breasts, her face, her hair, and of course, my tie between her breasts. She looked back down at me, and whispered, “Ready?”
“Whenever you are,” I replied, staring back into her eyes. I then watched as Emily close her eyes and bit her bottom lip. I heard her suck in air through her bit lip, and before I had a chance to blink, Emily forced her entire body down on me, my prick ripping through her hymen and filling her completely. I had to close my eyes and suppress a moan as she came down on me. If I thought the first two inches were tight before, then there are no words for what fully entering her felt like. I must’ve just laid there with my eyes closed for nearly a minute soaking in the sensation. When I opened my eyes, I saw Emily looking back at me, her eyes full of happiness, her whole face slightly red, and that wonderful smile on her face. As I was looking at her face, I felt her lift her body slowly up, and then go back down. I had to close my eyes again and suck in deeply to prevent moaning. As she slowly continued, I gained enough control that I could hold back from moaning loudly, though my breaths were coming in deep bursts.
When I opened my eyes again, I saw Emily rising and falling on my prick. Her head was tilted up slightly towards the ceiling, her eyes were now closed, she was lightly biting her lip again, and had this look of pure ecstasy on her face. I slowly brought my eyes down her body and saw my tie swinging lightly back and forth with her breasts. Her breasts were lightly bouncing, not only from her movements, but from her heavy breathing. Her stomach appeared to be quivering slightly. Then I saw where our bodies met and, though I really shouldn’t have been surprised, I hadn’t thought much about it and was very surprised to see, as she pulled her body upwards, a few small trails of blood on my prick, only to see those trails disappear when she brought her body down on it again.
Having seen this, I couldn’t help myself and reached forward and placed my right hand on the front of her hip, sliding my thumb over her tiny, exposed clit, which I could see for the first time. This girl had to be the most sensitive girl in the world! As soon as I touched her clit, Emily slammed her body down harder than she had yet and gasped loudly. She stopped riding my prick for a bit, and opened her eyes and looked straight at me. She grabbed my hand, pulling it away, and shook her head while looking at me, indicating that I shouldn’t do that. I understood that she would not be able to stay quiet if I did, and raised both my arms to her sides, just above her hips. She smiled back at me, ran her hands up my stomach to my chest, closed her eyes again, and started riding my prick again.
While she was riding me, she was running her hands through my chest hair, occasionally leaning forwards and putting her weight on me while at other times tracing my nipples with her fingers. I started quietly moaning again. I slowly slid my hands up her sides until I was holding the sides of her beautiful breasts. I watched as Emily bit her lip again. I slid my thumbs around the sides of her breasts, slowly moving them inwards towards her nipples. When I finally flicked her large nipples, Emily started gasping again, and she started increasing her tempo on my prick. Her increased tempo caught me by surprise, making it my turn to gasp in pleasure. The speed, combined with her tightness, was overwhelming! I had to close my eyes and focus not to cum in her right then. I tried to focus on my thumbs on her nipples rather than my prick in her slit. My body started shaking, and I realized I was going to cum soon whether I liked it or not. But I was going to be damned if I was going to cum without this wonderful girl cumming as well!
I opened my eyes and slid my left hand up to Emily’s face and my right hand down to her hip. As my left hand reached her face, Emily’s eyes opened in brief surprise, though she kept riding my prick. I brought my hand around the front of her face, and traced her lips with my pointer and middle fingers. When she opened her mouth a bit, I slid these two fingers in her mouth and told her, “Bite.” She looked at me questioningly, but rather than answer her, I slid the thumb of my right hand back over her clit, and watched as she immediately closed her eyes and, first gasped, then bit down on my two fingers. I kept running my thumb in circles around her clit, while Emily started moving faster and faster on my prick. I was right on the verge, but I was trying to hold out until Emily hit her peak. Emily was moving so fast now I couldn’t move my thumb in circles around her clit anymore, I just held it in place and Emily brushed her clit against it as she was pumping my prick.
Soon, her body began to shake, and I could feel the quivers coming through on my prick. That was it for me, and I knew it. I slammed my hips up and launched shot after shot of cum into this young girl. Though Emily initially stopped in surprise when I started cumming, she soon picked up her tempo on my prick while it was cumming. Suddenly, while my prick was shooting the last of its cum into her, I felt Emily slam herself all the way down on me and bite down hard on my fingers with a guttural grunt. I quickly remembered where my other hand was, and started rubbing circles around Emily’s clit with my thumb. I could feel her body shaking violently on top of me and could hear many quick and violent gasps and moans coming from her mouth as she was biting down on my fingers. While I believe she was trying to stay quiet, she wasn’t doing a very good job, though luckily she wasn’t loud enough that anyone in the rooms next door could hear. I can only assume no one was in the hallway, as I would think they would’ve been able to hear her through the door.
When I heard her gasps slow down and stop shaking (though her body still spasmed every few seconds), I finally opened my eyes again. The sight was amazing – this sixteen year old beauty sitting on top of me, biting my fingers, eyes closed, head tilted up slightly towards the ceiling, and occasionally spasming which made her incredible breasts jiggle ever so slightly. As I was watching, the spasms came farther and farther apart, and Emily’s mouth let up on my fingers. I gently pulled them out of her mouth and caressed the side of her face, causing Emily to open her eyes and look directly at me. Her face was completely flushed as she smiled down at me. Then, without warning, she leaned forward, nearly falling on top of me with my deflating prick still inside her. I felt her large breasts crush against my own chest, with my tie still on her caught between us. Her face was mere inches from mine. Then she wrapped her arms around my neck and leaned the side of her face against mine. I kissed her cheek, and ran my hands up her back. Then I twisted my head in the same direction as hers so our faces were cheek to cheek and just laid there closing my eyes.
We laid there for what felt like an eternity, though it was probably not even a minute. Then, without warning, Emily lifted her head up slightly, looking at me. I twisted my head to look straight up at hers, and saw a slight smirk on her face. I was wondering what the smirk was about, but before I had time to figure it out, she whispered, “Now!”
Before I had time to react, Emily had leaned in and began kissing me on the lips. My eyes briefly opened wide in surprise. Then I closed them and began kissing her in return, bringing my hands up to her head and holding her tightly against me. Finally! I thought. This was the one thing that had been truly missing from the experience. Our tongues started flicking each other’s lips, and then flicking each other’s tongues, and finally we began to explore each others mouths. It was an unbelievable kiss. I think there was more love in this kiss than there had been in any other kiss I’d had in my life. It just went on and on, getting better as time passed.
As the kiss slowly ended, Emily started kissing my cheek, up to my forehead, and then pulled back a little bit looking at me. I had to ask, “Why couldn’t we kiss until then?”
Emily’s face flushed even more than it already was, obviously a bit embarrassed. “Well,” she began, averting her eyes from mine, “You see, I… well, I….” She stopped and took a deep breath, then looked directly into my eyes and told me, “I never really kissed someone before. I was worried I would be bad.”
I was completely shocked! I had my first kiss when I was 12, and here was this beautiful 16 year old girl hanging out with the most popular girl in the school, and she had not even kissed a guy before! Then something else struck me. “You mean,” I began, “you never–”
“Did anything with a guy before,” she finished for me, smiling. I suddenly thought back to when she was staring at my prick through my boxers and playing with it. She wasn’t staring at in surprise because she’d never seen a prick that big before, she had never seen any prick before! Holy shit! I had just introduced this girl, who I had guessed had been with many guys before, to all the pleasures of men, and I was the first person to touch this young girl’s body! She had never even seen a prick before today, and now she had one deflating in her body after making love to it!
I started thinking back through the whole experience and all the things that occurred that were new to her – me seeing and fondling her breasts, sucking on her nipples, her licking and briefly sucking my prick, me briefly licking her slit, my prick at the edge of her hymen, her slamming down on top of me losing her virginity to me, her body shaking, me cumming in her…
“Holy shit!” I said, leaning forwards starting to freak out, “Are you really on the pill?” I couldn’t imagine why she would be having done nothing up until this point. Maybe she had lied before just so that I’d make love to her!
Emily saw my face and started laughing. “Don’t worry, I am,” she replied. “My mom put me on it six months ago, just like I said before. She doesn’t believe I haven’t done anything with guys before. Plus, I figured, better safe then sorry. You never know when you might need it.”
I laid back on the floor, letting out a deep breath. That was a scare! I continued questioning her, “Why haven’t you gotten with any guys before? I mean, a beautiful young girl like you, you must’ve had the choice of just about any guy in this school.”
Emily smiled as I described her as ‘beautiful.’ “I’ve told you a million,” she began, “I wanted a mature guy, a guy that really liked me as a person, not just for my looks.”
I flashed an evil smile at her, “And what makes you think I’m like that?”
Emily got a smirk on her face and leaned up a bit and lightly slapped my chest. “Well, you are, aren’t you?”
I pulled her back down on top of me. “Of course I am, Emily,” I whispered, “You are a wonderful girl. You are funny, nice, honest, and of course beautiful. Any guy would be lucky to have you!” Emily then kissed me briefly then leaned her head against mine again and we both just stayed like that for awhile.
Unfortunately, I knew what I had to say next, and I knew it would ruin the moment, so I held back as long as possible. Finally, I whispered, “You know we can’t do this again, Emily.”
I felt a drip against my face as she lifted her face away from mine. I looked up and saw she had been lightly crying, but she was smiling back at me. “I know,” she whispered back, smiling.
I wasn’t expecting this response. Rather, I was expecting her to get mad at me. I brought my hands up and wiped her tears from her face as I queried, “You do?”
“Of course,” she replied, still smiling but still tearing. “I knew from the beginning that if this happened, it was going to be a one time thing. There are too many risks, for you and me. I certainly don’t want you to get in trouble, and hope I can still see you around the school.” She paused for a second, looking down. Then she looked up, with a bit of a worried face and asked, “You don’t regret it, do you?”
I looked straight into her eyes, smiling, and told her, “Emily, this was the greatest and most loving experience of my life. I’ll never forget it. I wish we could make it last, but we both know it wouldn’t work. I hope you don’t regret it either.”
She smiled back at me. “Of course not,” she whispered back, “I am so lucky to have such a great guy, Mr. Ryan, even if it is only for one period.”
One period! That’s right! I had completely forgotten about the time. I looked up at the clock to check the time. Six minutes left of the period! That whole experience had lasted less than half an hour. Emily saw my gaze, and said, “Guess we should be getting dressed now, huh?”
“I guess so,” I sadly replied. Emily began to stand up, my limp prick finally popping out of her. As she stood up, I sat up. She was about to turn around to get her clothes, but I grabbed her arm, keeping her facing me. Confused, she looked back at me. “One last thing,” I said. I reached over to the desk, and Emily followed my hand. But she suddenly frowned and grabbed my hand before I could get what I wanted.
“Oh my god,” she whispered, while looking at it, adding “I’m sorry.” This completely confused me. I looked at my hand, and saw that there was some light blood coming from a couple teeth marks. Apparently she had drawn blood while in the midst of her orgasm, and I was too lost in my own orgasm to notice it.
I just chuckled, looked back up at her and said, “Well, I guess we’re even.”
“What?” she replied. I just pointed towards her slit, which had blood, and cum, dripping out of it, starting to drip down the insides of her thighs. Apparently she had forgotten about that, or never saw the blood in the first place, I don’t know. She started giggling now. I pulled my hand away from hers, and reached for the desk again, grabbing a tissue from the box. I then took the tissue, and wiped the blood and cum dripping down her thighs, and then what was leaking from her slit. I took advantage of the situation to spread Emily’s lips and finally see her beautiful pink insides without my prick in her, I gave one more light wipe inside, gently flicking her clit as I wiped it, which elicited a light gasp from her and a push from her hips. Having cleaned it completely, I leaned forward and gently kissed her clit, then looked back up at her, seeing her smiling down at me.
“That’ll probably make putting your panties on more comfortable,” I told her, tossing the tissue into a garbage can on the other side of the teacher’s desk. She giggled some more, grabbing my wrists and pulling me up.
“Your turn,” she whispered in my ear, while reaching to the desk for a clean tissue. She then sank to her knees in front of me, and began wiping off my prick, balls, and the skin around them. This was another time I was glad I shaved down there, as that would have been an unrecoverable mess! But as it was, Emily lightly rubbed the tissue around my prick, and briefly cleaned up the few drips of blood and our mixed cum on my balls. She then moved up to my shaft, holding my prick straight out by the head, and wiping up and down the length of my shaft. She then let go, wiped her hand a little, then put her hand around the shaft now and began wiping off the head. Her light rubbing of the head caused my prick to jump a bit in excitement level, causing me to gasp. I saw her giggle at this response, followed by her leaning forward and gently kissing the head of my prick.
It was now my turn to pull Emily up by the wrists. She turned slightly and tossed her tissue into the same garbage can I threw mine in. I looked up at the clock – four minutes left. “I guess we should get dressed again now,” I whispered, smiling at her.
Emily put on her best pouty face, and whispered, “I suppose. Guess that means I have to give this back to you.” While saying that, she pulled my tie over her head and handed it back to me. I gave her my most loving smile as I took it and put it down on the desk. I then briefly soaked in my first sight of Emily’s completely naked body, without my tie, knowing that soon that beautiful slit and those enormous breasts would be hidden from my view forever, never to be seen again. When I looked up to her face, I saw Emily’s eyes coming up my body. I was wondering if she was doing the same thing, trying to keep a mental image of my body for the rest of her life. I guess I’ll never know. When her eyes got up my body and met my own, we both smiled at each other, though it was a sad smile as we both knew our time was coming to an end. We soon turned and took the few steps towards the pile of our clothes.
Emily grabbed her white lace panties off the top while I dug out my boxers. I was about to step into my boxers, when I looked over and saw Emily stepping into her panties, and slowly pulling them up her legs. For some reason, I became completely entranced by it. When she had them up, she looked up and saw me staring at her. She smiled, giggled, and said, “Mr. Ryan, I don’t think you’re going to get dressed by staring at me.”
I blushed, not having realized how badly I had been staring at her and how desperate I must’ve looked. I immediately put my boxers on, and reached for my pants and undershirt, tossing them on the desk for easy reach. As I did this, Emily grabbed her bra, shirt, and skirt putting them on the end of the desk near her. I looked away from Emily briefly while putting my pants on, and then my undershirt. When I looked back at her, the only thing left on the desk was her skirt, and her beautiful breasts were hidden behind her shirt again. Though I knew this had to happen, I couldn’t help being slightly disappointed.
Suddenly, the afternoon announcements began over the loud speaker, signaling that there was only two minutes left of the period. Both Emily and I suddenly went into a frenzied rushed dressing state. I pulled my dress shirt on, buttoned it up as quickly as possible, pulled the tie over my head, under my collar, and tightened it. I then stepped into my shoes, without socks, pushing both my socks and watch under the desk, hoping I looked decent enough. I looked up and Emily was standing completely dressed, waiting for me to finish.
As I looked up, I said, “Time to go, Emily.” She gave me a half smile and started walking to the door, with me following right behind her. About halfway to the door, it struck me how sad an end this was to our brief time together. I suddenly grabbed one of Emily’s arm and pulled her back to me, spinning her around in the process, and without saying a word planted my lips on hers, and kissed her for a few seconds. She kissed me back, and we briefly relived our past experiences, savoring this last kiss. When I pulled back, Emily’s eyes were closed, and a couple tears were going down one side of her face. I wiped them away with my thumb, leaned into her ear, and whispered, “I love you Emily.”
I heard Emily whimper in response to this, and through the whimpering, whispered back, “I love you too Mr. Ryan.” I smiled at her, wiping away a couple more tears. The afternoon announcements ended while I was wiping away her tears, reminding me how short we were on time. I stepped in front of her, getting to the door. I turned on the lights and opened the door, stepping out to see if anyone was in the hallway. It was completely empty. I stepped back into the classroom and nodded in Emily’s direction, indicating she was safe to go. She just smiled, and walked by me. I reached out and ran my hand down her back as she was stepping through the doorway, but she didn’t turn around and kept walking out of my sight. I waited just inside the door of my class, buttoning the cuffs on my shirt. What must’ve been less than ten seconds later, the bell rang. I waited five more seconds in my room and heard the hallway get loud as the classes got out. I then walked out into the hallway, which I normally did at the end of the day to monitor hallway behavior. I looked to the right of the door, and saw the back of Emily’s head far down the hallway disappearing into the mass of people. I kept hoping she’d turn back, so I could see her face again, but she never did, eventually reaching the stairs and going down them and out of my sight.
I tried to be personable as other students came up and talked to me about various things, but it must have been pretty obvious I was distracted, repeatedly looking back to where Emily had been walking away, despite the fact that she was long gone. About six minutes later, the hallways were clearing up as students were leaving school. I went back into my classroom and went to the teacher’s desk. I took off my shoes, putting my socks on and then put my shoes back on. As I was doing this, I noticed the bite mark on my fingers again, having briefly forgotten about it. There was still some light blood coming from a couple teeth marks. I opened the front drawer of the teacher’s desk and pulled out a couple band-aids, wrapping them around the two fingers with bite marks. I then put my watch on and went to a closet at the side of my room and grabbed my jacket and put it on.
Normally I leave a note for the teacher I sub for, but I could not think about that right now, so, after putting my jacket on, I grabbed my messenger bag and slipped it over my head. I then grabbed the folder off the desk and unclipped my name tag from my shirt pocket, and walked out of the room, turning off the lights as I went.
As I handed in my folder, nametag, and keys at the office, the secretary saw the band-aids on my hand, and exclaimed, “Oh! What happened?”
“I accidentally closed a drawer on my fingers,” I replied, a bit spaced out.
“Ouch!” she said back, cringing, “That must’ve hurt!”
I smiled, telling her, “Oh, it wasn’t too bad,” as I turned around, walking out of the office and heading out of the school.
I should add a couple side notes here. As I continued subbing at the school, I saw Emily many times after this. It seemed she would search me out whenever she heard I was in the building. Though nothing like this ever happened again, whenever she saw me she would always give me a hug (the kind where you wrap one arm around the other person), which I would always reciprocate. Another odd thing, Emily began calling me ‘Mr. Ryan’ instead of just ‘Ryan.’ I’m not sure why, she did that, but I can tell you that it caused many a rise in my arousal level when it happened, always reminding me of our time together. She also seemed much happier anytime she was walking down the halls than she was before this whole event occurred.
As a final note, I was in for a surprise when I got home that day. When I got back to my apartment, after putting my jacket away and taking my shirt off, I went to empty out my bag. When I opened it though, I was completely surprised to see Emily’s white lace bra was right on top. Apparently she had slipped it in my bag as she was getting dressed. I laughed, pulled it out, and looked at it. It truly was a beautiful bra. It constantly serves as a reminder of what transpired that fateful day. I actually put it under my pillow, and to this day, whenever I’m feeling depressed or desperate, I pull it out and look at it briefly, then close my eyes and relive the whole ordeal. And let me tell you, I’ve never had a better orgasm when masturbating than I’ve gotten while dreaming of that incident with her bra in hand.
