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Virtuous Vices Part 2

Penny finds out that masturbation isn't the most pleasurable part of sex.
Virtuous Vices Part 2

This is part two of my story about Penny, the sixteen year old desperate to grow up but afraid of losing her own privacy. I hope you enjoy.

Well it had been just over a week since he sent the email and although now, when I masturbated, I came stronger than ever before, nothing much else had changed. I still didn’t know who he was, this strange voyeur. We spoke often via email. He never offered any information, nor did I ask. I was a little afraid that reality wouldn’t live up to expectations. He complimented me often and when I asked him if he knew my age he said numbers didn’t matter and so I didn’t tell him I was only sixteen. Sometimes he’d ask me to do things because he liked watching me do them. Although he didn’t specify when I should do them, and I didn’t for one minute imagine him sat wherever he was waiting all day I’d do them two or three times for him, maybe more. And when his next email arrived he was always very grateful for me complying.

The things he wanted me to do weren’t too odd, so far at least. I enjoyed doing the more unusual ones for him like sliding my fingers inside my bottom because it felt very naughty and I was definitely decidedly curious. It felt good, and I imagined him thinking about his fingers going inside me there as he stroked himself to climax. But mostly it was positions he’d like to see me in. On all fours with my tiny breasts pointing to the bed and my hand between my legs, flat on my front, laid sideways and many more. I knew from our conversations that he wasn’t some young ill-mannered teenage boy. He hadn’t told me his age but the language he used was intelligent and well thought out.

I liked this arrangement, it suited me more than I had ever imagined. If I didn’t feel like talking I’d ignore the email until the morning or the next night. He didn’t infringe on my Dad time either, as he never emailed whilst he was there.

My inability to concentrate at school stopped and I found my daytime daydreams whilst sitting under the old oak tree pleasant and fruitful once more. I was, however, aware that things could change. He might ask, or even demand, that we meet. This didn’t worry me too much, I was enjoying things so far but I had started to imagine what it would be like to have him in my room watching, rather than in the far distance. I wondered if he’d enjoy the mutual masturbation as much. Or would I? I hadn’t even seen a man’s arousal apart from on the odd picture. I didn’t know what their nakedness smelt like, looked like not to mention their orgasm. How would he sound pleasuring himself? Actually sound, not what erotica told me. Furthermore would he find me as appealing close up? Did he really realise how young I was? From a distance I may seem to be eighteen perhaps, but close up I wouldn’t be able to hide my hairless cunt, or my freckled face.

This was on my mind as my English teacher announced this week’s homework; a short story. We had the last fifteen minutes of lesson to make a start on it. I knew I wouldn’t hand this piece in but I couldn’t stop myself writing about him. How he’d watched me through my bedroom window. I elaborated more around his character, describing the emails and pretending that he wanted to meet me. I told how he’d phone me and let me listen to him, describing how good it felt to touch myself for him. The story continued to him wanting me, aching for my youth.

I was quite enjoying writing down my feelings; it helped put them in order in a way. In fact I hadn’t even heard the bell ring for the end of the lesson I was concentrating that much. Nor had I heard, for the second time now, my English teacher sidle up to me. I looked up from my work and smiled. I hadn’t jumped this time and his fingers were nowhere near my nipple, unfortunately. Unfortunately?? What had I become! A couple of weeks ago I’d have blushed at my mind telling me such obscenities. Now I not only welcomed them with open arms but had, amusingly, started to embellish on them. I drifted into a half awake half daydream state where this person of authority, my teacher, with his thick ruffled dark hair and brown eyes told me he’d like to brush his fingers against my nipple once more. Packing my belongings up and having a quick check that I hadn’t left any tell tale marks of my arousal on the chair I left, desperate to continue this fantasy in privacy.

A good couple of hours later I realised my stupid mistake. I’d been that engrossed in my teacher seduces me fantasy and in that much of a rush to leave I’d left my story behind on the desk. I was foolish. It was if my young age was letting me down to ground me back into reality. Hey, you’re going too fast! It was bellowing in my ear. But what would happen now? Would he find the story and be shocked enough to ring my father. Would he realise the meaning behind the story? Well, I hadn’t heard from Dad yet, so perhaps he hadn’t told him, yet. Maybe he’d not found it. But I knew if I left it there it would be found sooner or later.

Dressing quickly I fled to the school. The Caretaker would let me in if I told him I’d left my house keys on my desk, if all the teachers had left. A little white lie to save my skin. Because if Dad did find out I was writing such things he’d assume, quite rightly, that something was happening even if I wasn’t actually meeting this fellow. And if that happened I would lose everything. I’d grab the story and thank my lucky stars that I’d not been caught before punishing myself for my foolishness. That was if it was still there.

The car park was empty of its usual melee of cars. The school looked sad and disregarded at this hour of day. Bygone was its rush of hurried feet from classroom to classroom; its walls empty of their usual canteen aromas. I wanted to set it free as I was, embrace it and kiss it farewell. Never the less it wasn’t a time for empathy, my own liberty was on the line. If I didn’t hurry I’d look just as melancholy as the building I was staring at now.

I knew I was stalling. I didn’t want to lie but it was a necessary evil. I had left something behind, it just wasn’t my keys. But if I told the Caretaker the truth he might tell me to wait till morning. I had to lie. Finding him in his usual place, working in the tool shed, I greeted him with a fake smile, gave him my lie and almost, just almost, replaced that nervous pseudo smile with a genuine one as he led me grumbling to my classroom.

“I take it you know your way out young lady? Or do I have to wait all evening while you look?”

I nodded in desperation for him to disappear. The gruffness in his voice sending shivers of fear over my body. I never lied, hardly ever. I feared the loudness of his call would awaken others dotted around the building and they would gather and my lie would increase like Chinese whispers before I didn’t know what it was I’d come for in the first place. I had to move fast.

Already I knew it wasn’t sat as I’d left it on my desk and that was before I’d even crossed the room. Striding over with fear weighing down my every step I checked inside the desk drawers, nothing aside from the usual pencil shavings and notes. Well it wasn’t in my school bag, I’d emptied it and triple checked. Glancing over to the front of the classroom my eyes scanned the teacher’s desk. Immediately without thought I crossed the room and rummaged through his drawers. There were so many pieces of paper this would take ages. I tried to work fast, looking for my handwriting amongst all the others.

“It’s just NOT here!” I shouted out loud in frustration, not caring who came or saw me. The game was up.

I saw his shadow before I saw him. His silhouette outlined across the floor from the light in the hallway. Daring not to turn my body trembled with fear. Not only had he now obviously seen my fantasy story but he’d also caught me with my hands in his desk. I didn’t have a system folder of lies in my mind that would cover this.

“Looking for this?”

His voice was smooth and had the teeniest trace of a northern accent mingled in. I hadn’t noticed this before. Perhaps now it was time to properly listen.

I turned, my eyes fixed firmly to the floor. Shame thundered through my bones. A tear fell to the floor on his shadow, pooling waiting for the stream to follow. The game was definitely up. I dared not answer.

He crossed the space between us. I wanted to run. Fear had now bolted my feet firmly to the floor. Quickly I tried to think of the possible outcomes. I lie and say it wasn’t me who wrote it. I lie and say it was make believe. I plead for forgiveness and ask him to forget he ever saw it.

His fingers, the same fingers that had grazed my nipple accidently over a week ago now held my chin up so he could look me in the eyes. I didn’t look at him still, knowing what he saw, reddened bloodshot eyes and tears. Gently his thumb wiped my tears away; joined by his other thumb he cupped my face, tenderly forcing my eyes to lock with his.

I didn’t see anger, or hate, or rage of any kind. I wasn’t even sure if I saw him, the way he usually looked. He wore a kind of look of recognition on his face which made him appear different than the man who was my teacher. Yet the same dark brown eyes and ruffled, if not more messier hair, stared back at me. I imagined he’d raked his hands through his hair agonising over my story over and over.

“Did, err...” my voice croaked. “Did you phone my father?”

I expected the answer to be yes. I knew it was yes, but as he whispered no into my ear it still took several minutes before I realised that he’d said no.

My face still sat in his hand and as I tried to make sense of the situation I noticed he was breathing in my aroma, deeply inhaling the scent of my hair. I could feel his breath against my neck; it warmed the goose bumps that had arrived moments earlier, easing them a little.

“Do you want me to?” He asked.

Confusion reigned in my mind. I knew what he meant but the question seemed open ended. Perhaps it was the sudden rush of adrenalin that accompanied my relief that caused me to react in such way. Did I want him to do what? Kiss me like the handsome men in the erotica I read so avidly? Watch me like the other man. I wanted to say yes, scream yes please. I wanted him to be my hero. But in saying yes he wouldn’t do any of the above. He’d let go of my face and pick up the phone next to us.

I didn’t want him to let go. His touch felt almost fatherly, like he cared more than I knew. I realised as the light cotton material of my hastily thrown on school dress grazed against my breasts that my nipples were reacting once more to his closeness. This time there wasn’t any training bra to hide a little bit of my modesty, just naked skin against gingham material and I knew how erect they’d become the more aroused I felt. If he shifted the position of his arm slightly he was sure to find my predicament.

Kissing my forehead he pulled me into an embrace, pressing my body into his, folding his huge arms around my tiny frame. I hoped, perhaps, that he wouldn’t feel my swollen nipples through his corduroy blazer. Leaning my cheek against his chest as I was too small to reach his shoulder I too began to deeply inhale his scent. It was an intoxicating mix of sweat, the school itself and books, yes books. I loved the smell of books. Drawing in again and again this heady potion I closed my eyes and relaxed into his body.

I could have slept, there and then in his comforting embrace. If it wasn’t for my body playing host to my minds desires. They worked in unison, creating almost a reality out of my thoughts. When I imagined him kissing me, telling me everything would be ok, my lips tingled causing my tongue to dart out and moisten their need. This worked on all levels, right down to my toes.

Alas I knew it was all pointless. I was sixteen, he was my teacher. He was merely comforting my sadness. What would he want a naive school girl for? He was, I knew now, quite handsome.


His voice broke my thoughts. Carefully almost as if he did it reluctantly, he widened the zero gap between us, placing his hands on my upper arms.

“Was the story true?”

I looked down to the floor and then back up at him. My Dad’s face flashed upon his, just for an instant. I knew then I couldn’t lie. Sitting down we allowed a desk to separate us. I explained, trying to alleviate any morsel of embarrassment on my part by not admitting directly that I masturbated often, that it was true up to a certain point. He didn’t need an explanation, I think he understood that I was, yes, letting this stranger watch me, but I hadn’t, yet, met him.

When he asked if I would meet him, again I found it impossible to lie, to him or myself. I knew that although I had agonised over if there would be the question of meeting I had already unknowingly allowed myself to consent to a meeting. It was the next step on my ladder of self learning. He looked pained at my yes answer to his question.

“I do not need to tell you that what you are willing to give him is a huge thing, Penny. I do not need to tell you of the risks either. I know you’re going to take this step sooner or later even if it isn’t with him...”

He stood, rather forcibly, and paced the floor in front of me, running, as I had predicted, his hands through his hair. Stopping suddenly his face softened and he crouched immediately in front of me. I listened; I really listened as I knew it was the time to start listening, as he’d entered the room and found me I had predicted that too. He explained that as my teacher it was his job, not job but duty to teach me and it angered and upset him to think that anything I was going to learn, anything at all, had to be taught in the correct manner. There were things that could hamper my learning if not taught correctly, and even spoil my innocence.

“Let me be your teacher, Penny, let me show you what that man, whoever he is, would have shown you. I care for you Penny and yes I am envious of what he’s seen. I watch you daily sit under that tree with your eyes closed daydreaming. Only now I know what you’re dreaming about. I suspected it, but wasn’t sure. Penny.. do you understand?”

I think I did. He wanted to teach me how to become a woman, what I suspect I’d have learned from a continued email relationship with that man. He did want me. My head mixed with thoughts, whizzing around making me dizzy. But I didn’t know what to do; he’d laugh at my incompetence. Or maybe not, he wanted to teach me, right? If I knew everything then they’d be nothing to teach.

I nodded slightly and blushed, staring at my feet.

Standing me up he mumbled in my ear, ‘Now where were we?’

Slowly he ran his fingers from my neck line down my throat before parting on my chest circling his thumbs underneath my small breasts. The cotton material of my dress pulled tightly against my nipples, showing them off precisely to his eager eyes. Hungrily he raised his thumbs and this time he deliberately grazed over their peaks. Or perhaps now armed with the knowledge I had now it wasn’t ever accidental. I couldn’t help let out a low deep guttural moan. Although the air had caressed me numerous times I had never been caressed by any hands other than my own. And as he rubbed them both between a finger and thumb alternating from softly to harder, more certain strokes I knew now that anything I felt previously, even knowing that someone was watching paled to the arousal I felt now. The jolts that usually ran from the tips of my nipples as I caressed them to the pit of my stomach and then onto the desire between my legs were now merely trifling whims compared to the huge avalanche of volts that made me visibly shake and shudder.

As he continued his pursuit of my pleasure on my nipples alone for now his mouth accompanied his lesson starting on my long protruding neck and throat that jutted forward as my head hung back from the pleasure. His lips were warm and delightful. Tiny butterfly kisses ran straight up the under my chin and back down leaving a trail for his eager tongue to follow. I wanted to feel his lips on mine so I leant my head back forward causing our lips to join instantly. Softly we kissed, his tongue darting in and around my mouth.

My dress was removed with one swift move. He stared at my nakedness beneath, his eyes lingering on my hairless pussy and the wetness on my inner thighs. I wasn’t scared of him running at the sight of my immaturity. The look of passion in his eyes gave me the strength to be certain about his desires for me.

Laying me down on top of his desk his tongue and lips continued their journey from my neckline, past my nipples stopping slightly to circling them briefly right down to my navel. He’d undressed as quickly as he’d undressed me. It was now I caught sight of his true arousal. I gasped, not realising how large it would be. It stood erect and proud, jutting out from dark black curly hair. As lethal as it looked I could tell it would be soft and velvety to the touch. However I knew now wasn’t the time for me to find out as he dipped lower in his actions, his tongue lapping up the juices on my inner thighs.

My clitoris was tingling in anticipation, swollen more than I had ever known it to before and the more he idled on my inner thighs, teasing me, the more it ached for his touch. I expected his lips to touch its eagerness, or his fingers, but as he climbed over me, kissing my forehead once more, his own arousal undirected by his hands at first, rubbed gently against its urge. This time I gasped louder, nearly exploding there and then at the shock that ran through me. Now my silly thoughts of being able to please myself without the need for anyone else were put to shame. I had never felt such pleasure before. My god, I’d nearly cum from the briefest of touches.

I dug my nails into his back as he grabbed hold of his own need firmly in his hand and rubbed it forcefully against mine. Running it up and down and around and around he brought me closer and closer to my orgasm. Looking in my eyes he searched for something, at first I didn’t know what – but as I almost reached my orgasm he knew, as my back arched and my eyes glazed and my breath shortened I invited him to join me. He instantly, without fault or hesitation, pushed himself lower against me, entering my wetness. He slid almost effortlessly into my innocence, taking from me what I wouldn’t ever be able to offer any other man, but didn’t want to. It was now that I understood the gift he talked about that I was willing to give to the stranger who watched me. I knew, however that as my orgasm erupted instantly when he plunged fully inside me that I was glad I’d given it to him, my teacher.

He came moments later after I had, filling my tight previously unchartered pinkness with wave after wave of warm cum. I sensed he’d tried to hold back, last longer, but his need was as great as mine.

“You’re beautiful” he whispered as his kissed me, our union still undisturbed.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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