Dear Diary: the Beginning

Dear Diary, part one.

Today like all other weekdays I went into school to teach my classes. I would have the seniors today, last period and I have to say, I was feeling a little uncomfortable about having to listen to a certain young boy read. Tudor 10 (house name) is my class of eighteen year olds and the young boy I am talking about is in this particular class. We shall call him W to protect him, although I fear that it may be I who am in need of protection from his rather precocious ways. This particular young boy has developed a rather large crush on me and I have noticed, when he is around me, he has taken to fiddling in his pocket a lot. Added to that, he will take every opportunity available to either look at my cleavage, or up my skirt and recently he has been brushing up against me a lot.

W, is a very good-looking boy, this cannot be denied and will obviously be a great success with women when he gets older. He has the most beautiful green eyes and dark hair, with a chiselled bone structure that an artist could not improve upon. There is something about this boy that draws you to him, he seems much older than his years when you look into those eyes. Perhaps this is just me and I’m just over sensitive due to being flattered by this boys crush. I have certainly found myself responding and am ashamed to confess that I am now finding myself creating situations to provoke his attentions further.

Today for example I am wearing a grey skirt much shorter than usual, about 2 inches above my knee and is pleated, so it is not restrictive to movement at all. I am not wearing panties beneath, I have on black stocking held up by a rather sexy black lace suspender belt. I have put on an ordinary black cotton shirt, however underneath I am wearing a black lace wonder bra that lifts my breasts. The blouse is unbuttoned to the V of my cleavage, so when I lean over anyone stood at the side of me would have an ample view of my bra and breasts. Looking at me directly you would say I am dressed appropriately and sensibly, but that was my plan.

I listen to W read alone to me at my desk, because he has found it increasingly difficult to overcome his shyness and read aloud to the class. I felt he benefited from the one to one approach and it has proved successful, he is not struggling and academically he is certainly improving, but I digress. It is at these times that I have noticed W fiddling in his pocket and recently he has become bolder and has started to get as close as he can while trying to rub his self against my arm. I have pretended not to notice, hence his increasing boldness. Oh and he occasionally drops something on his way out of class, very close to my desk, so he can clamber underneath for a brief look up my skirt. The truth is, I have found that I am actually enjoying this and have been getting very wet during his reading sessions, to a point where I am continually squeezing my thighs together to get some relief. When he is gone, I quickly go into my storeroom, which is situated, behind my desk, to masturbate.

So you can see why I am becoming increasingly uncomfortable every time I am due to teach this boys class. I am afraid that one of these days I may have to keep this boy behind, take out his cock and let him feel what it is like to be in heaven. That is what worries me, for I have fantasised often about doing just that, indeed today I have perhaps gone a little further than I should with my teaching.

Today’s class was an hour long and the last class of the day. By the time his group came into my class, I was feeling very aroused and in dire need of some relief. When they were all sat in their places I began their English lesson, eventually asking them all to begin writing an essay, which they would later take home and finish as homework.. I went and sat behind my desk, to do some paperwork, leaving the class to work quietly on their own. I moved some books around my desk and accidentally knocked off my desk tidy, which contains all my pens. W, quickly jumped up from his place at the front of the class and offered to pick up my pens. I told him to go ahead and he informed me from his kneeling position, that some had fallen under my desk.

It was a very strange feeling to have this boy shuffling under my desk and knowing that I had no panties on. I couldn’t resist giving him a little peek and quickly uncrossed my legs and let them open just the tiniest bit. I knew he would be straining to see something, and would have an ample view, without anything being revealed to any other pupils. I could have sworn I heard his sharp intake of breath, indeed it may have been my imagination but I’m almost sure I felt his breath close to my knee. I opened my knees a little more; I wanted him to be very sure of what he was privy to.

This time I was almost positive I could feel the lightest of touches on my legs, which I pretended didn’t happen of course. Obviously I couldn’t let him stay under there much longer, without him drawing suspicion from the other pupils, I briefly opened my legs wider, enabling him to see my pink lips parted. I keep myself very closely trimmed down there; I know he would have had a beautiful view. I then crossed my legs and asked if he had found all the pens. Apart from a little hoarseness in his voice, when he replied “yes miss” he seemed to have coped with the show remarkably well, replacing the pens on my desk as if nothing untoward had occurred. However as he backed away from my desk I couldn’t help but notice the front of his trousers looked a little bulky, this pleased me very much.

I think it was only a couple of minutes passed when I looked up and noticed his hand in the air, “yes W” I asked “is there something bothering you”. “Miss, I don’t understand this passage in my book” he replied. I beckoned him over to my desk, telling him to bring the book with him. He obediently took his place to my left leaning over to point at the passage that was confusing him, telling me exactly what he did not understand. The chair that I was sat in, is a rather comfortable swivel chair with arm rests. I rested my left arm upon the rest, this meant that I was leaning slightly toward him, I knew the position would give him a good view of my breast if I moved my right arm or shoulder forward. This I did, while innocently explaining the passage to him.

I felt him move closer to my arm, standing slightly behind me, I could feel the swelling in his trousers against the back of my arm and occasionally, I could feel him shift his weight from one foot to the other in order to massage his self against me. I thought I might inadvertently assist him, so began playing with a pen on my desk, this caused my arm to move gently against his erection. I was a little afraid that this boy might cum in his pants and scurry away nervously. But I have to say W seemed to be made of stronger resources, in fact I wonder if he was manipulating me, he certainly seemed in control of himself. I continued to lean forward, while explaining the passage to him, ensuring that he had a good view inside my shirt. At one point he leaned over to point something else out and I’m certain he hesitated to breathe in the scent, around my neck, I could feel the whisper of his breath which caused Goosebumps to rise on me.

I felt myself getting very sticky below the desk and was desperate to slide my hand underneath and stroke myself. However propriety would not allow me to do that just yet. After I finished explaining the passage to him, all the time continuing to innocuously and gently rub my arm against his cock, while at the same time giving him a good view of my breasts. I asked if he now understood the passage, he calmly said he did and moved back as if to move away. I don’t know what came over me but I quickly decided that I had not finished with him yet and felt I didn’t want him to waste that orgasm by masturbating later in the boys’ toilets.

I hadn’t given any thought to what I was doing, but said to W, that seeing as there was only 15 minutes left of class he could help me collect some books together from my storeroom and continue his work at home. He readily agreed. The rest of the class, were quietly working away, so I led him into my storeroom. Actually it’s more than a storeroom, it is quite a big room I also use it to have breaks in, when I can’t be bothered with the staff room. There is an easy chair in there, which folds out to a bed should any of my students or I feel a little ill. I have a coffee machine and a small refrigerator in there too and all my stationary and exercise books are stored on the shelves around the room. The storage shelves reach all the way to the ceiling; I have some stepladders to help me get to the higher shelves. With the storeroom door closed, one can be afforded much privacy, however I left the door open, I needed to pay attention to what the rest of the class might be doing. The storage shelves are on the wall left of the door, no one can actually see into this room from the main classroom even with the door open, they would have to walk in.

On entering the storeroom, I bustled about to find W a box, explaining that I would like him to put some things in it that I needed to take home with me. I told him that I needed some stationary from the top shelf and asked if he would stand below me, that way I could easily pass them to him from the ladder. Added to this he could ensure that the steps remained stable for me, again he readily agreed, looking slightly flushed. I smiled to myself, as I was sure he must have thought all his dreams were about to come true, which indeed they were. I had not planned any of this, therefore had no idea how he would respond or for that matter what my next step would be. At this moment my thoughts were upon the aching need within me and how incredibly turned on I was. Perhaps if I had given myself time to think I might not have proceeded as far as I inevitably did.

I slowly climbed the ladder, while W placed himself strategically, I thought. He stood astride the bottom of the steps, holding the sides of the steps with both hands, almost lying against them, which would afford him the best possible view. Obviously he knew I was not wearing panties and he was probably certain he would get another show, how could I disappoint the boy. I climbed about four rungs and then placed one leg on the next rung up, this had two benefits, the first being that my legs were completely stretched apart allowing W to have full view of my, now very wet pussy. The other being that my skirt slid up my thigh exposing my stocking tops. I slowly took one book at a time and passed them down to him, I then made a point of not being able to find a particular book and pretended to look for it. Taking a furtive look down at W, I noticed his hand was very obviously rubbing the front of his pants. The sight almost had me falling, as I imagined descending the steps, freeing his cock and having him fuck me against the ladders. I pushed the image from my mind, I would not, could not allow myself to take too much advantage of this boy. I informed W, that I had found the book, in order that he correct himself before I passed it to him. I was surprised at how calm and in control he appeared to be, as I leaned down to pass him the last book. I slowly descended the rungs while W busied himself putting the books into the box I had given him earlier.

I informed W that I was going back into class and that he had about five minutes before class ended. I said he could stay in the storeroom and finish packing the box for me and anything he didn’t manage to do I would finish later as I would be working late this evening. I then went back into class to go about the arduous task of getting all my students to pack up their things properly before leaving for home. Also to be sure they understood their assignments, after all I still had my responsibilities. All the time I was doing this, I was conscious of W, still in my storeroom, I just knew that if I went back in I would find him masturbating, which had me so wet I could feel my juices trickling down the inside of my legs. About a minute before the bell was due to sound, alerting the children that it was time for home and therefore stampede, I let them all go. As the last three children were leaving the classroom, the school bell sounded, I expected W to come scurrying out of my storeroom looking all flushed and embarrassed, but he didn’t. I waited for a minute or so, but he did not emerge, I called his name and said it was home time, either he didn’t hear me, or he chose to ignore me.

I ventured back into the storeroom, a little nervous of what I might find. I feigned mild shock as I walked in and saw W stood nonchalantly leaning against the ladders rather confidently and slowly stroking a rather impressive penis. I adopted a slightly stern tone and asked him what on earth he thought he was doing. W immediately burst into tears, however as I rushed over to comfort him, I noticed that his penis had not lost its erection nor for that matter had he stopped stroking it. I pretended nothing was unusual as I put my arms around him placing his head upon my chest, I told him that he shouldn’t feel ashamed, what he was doing was normal for all boys. He continued to sob into my cleavage and I was pretty certain this clever young man thought he was cleverly manipulating me. All the time he was crying, I could feel him rubbing himself faster against my thigh and realised that he had probably planned this little charade while I was in the classroom. I had to smile to myself; I was indeed impressed at this boy’s cunning ingenuity.

I decided that I would play along, so continued to stroke his hair and offer soothing words. W’s sobs had subsided into snuffles and his head was resting in the open V of my shirt with his face turned towards my left breast. His left hand continued to rub his cock, he brought his right hand up to wipe the tears from his face, which allowed him to accidentally brush his fingers against my breast. I pretended nothing untoward was happening. Through his tears he was saying that he was sorry and pleaded with me not to report him to the headmaster. Even though I got the distinct impression that he was having no such regrets, I continued to reassure him that on this occasion I would not report him, explaining why he should not have been doing that to himself in my storeroom. W was panting, which could have been through his sobbing, however I felt certain it was more to do with the frantic rubbing I could feel against my leg. I’m sure I felt his tongue flick against the side of my breast; the heat in my pussy was becoming unbearable.

I continued to ignore the fact that he was blissfully jerking off against my thigh and asked if he felt ok to go home now. At that moment I felt him shudder, I carried on stroking his hair and gave him the impression that I thought he was still upset. I heard him heave a huge sigh and knew that there would be a large sticky patch against my skirt, when he moved away. Strangely enough, after his breathing had returned to normal, he calmly stepped back, slowly put his now flaccid penis back into his pants, looked at me with those beautiful green eyes and said “thanks miss” and calmly left.

After he left I took a few minutes to compose myself, I needed to re-orient myself before going back into the classroom to make sure everything was as it should be. Eventually I walked back in and began to tidy things on my desk, putting away my books and pens. While doing this I looked around the class and I noticed that beside W’s desk was his school bag. I didn’t pay this much attention as children were often forgetting their bags, usually as a justifiable excuse for not doing their homework.

Everything tidied I went back into my storeroom, made myself a coffee and sat back in my easy chair to think about all that had occurred. I was in no rush to go home, there would be no one waiting for me and I often stayed and did my marking at school. I preferred to do this as it meant I wouldn’t be taking work home with me. I hated to do that.

As I sat there, flicking through some of the children’s exercise books, I became aroused all over again recalling W masturbating, then feeling him doing it against my leg. The boy had obviously had some agenda of his own and I had willingly colluded, if not manipulated the situation further. Believe me, I have had boys have crushes on me before, even tolerated some rather immature efforts to see up my skirt. But never have I allowed a situation to get out of hand in anyway. In reality I prefer my men to be a little nearer my own age and have never fantasised about boys, until this one of course. This boy seemed different somehow; perhaps it was just the way he seemed to look at me with those green eyes, eyes that appeared older than their years.

I found myself unconsciously clenching and unclenching the muscles in my pelvis. The school would be empty now, it would be a good time to relieve that build up of tension, especially here where I had only minutes earlier had the novel experience of a young boy ejaculating over me. I decided to unfold the bed, I wanted to take my time and enjoy reliving every moment of my last lesson. Again I left the storeroom door ajar I still needed to hear if someone entered the classroom, like the cleaner or caretaker. I was certain that no one could see me from the classroom, so felt I could enjoy myself undisturbed.

Once I had unfolded the bed, I lay down on top of it and just allowed myself to wallow in my recollections for a few moments. Of their own volition my hands crept up to my nipples and began stroking them over my clothing. Mmm there is something very erotic about masturbating where you know you shouldn’t, where you may possibly be caught. It is also a very nice feeling to touch myself over my clothing, feeling the friction of the cloth against my skin heightens my sensitivity. My nipples are very sensitive; I often feel that there must be a nerve that connects my nipple to my clitoris as touching the first causes an automatic reaction in the other.

I continued to stroke my breasts, while my mind conjured up images of that young boy. Slowly I began to unbutton my shirt, I needed to feel my hand caressing my soft skin, I unclasped my bra and felt the cool air kiss my breasts. I couldn’t take the risk of undressing completely, after all if someone did walk in, I would be caught naked, with little explanation. This way, I could tidy myself up quickly if I heard someone enter. I let my nails gently illicit tingling sensations from the peaks of those soft fleshy mounds, shivers coursed through me and I could feel the heat rising below.

I heard a sound emanating from the classroom, a creak of a floorboard perhaps; I stopped what I was doing to listen. I heard nothing more, I rationalised that if someone had come in I would have heard them moving about. I presumed I had imagined the noise, as I didn’t really want to get up and check, everything seemed to be very quiet.

I continued touching myself, allowing my hands to glide over my stomach, wandering back and forth to my breasts in lazy, tingly swirls. I was painstakingly slow, enjoying the sensations that my fingers were arousing. After some minutes, I lifted my knees, this movement caused my skirt to slide up and bunch around the top of my thighs. I let my hands move down to caress my thighs, first over the silky material of my stockings. As I let my knees part and fall, I remembered I was not wearing any panties I felt the cool air whisper against me and cause the dampness there to feel cooler. I delicately scratched along the naked part of my thighs, luxuriating in the almost painful effect it was having upon my senses. Aching to feel my fingers stroke my now, throbbing pussy. I waited continuing to run my hands gently over my body, while my mind invoked decadent scenes of carnal depravity, which involved an innocent young boy. In my mind I could allow anything to happen, things that I would not permit in reality.