Plain Jane Becomes Dirty Jane

My name is Jane Rawlings, and at the time this story begins in 1990, I was 20 years old. It is the story of my sexual awakening and a gradual drift into my craving for more risqué encounters with men and just more men.

I have always been tall for my age, and now at 5' 11" was the tallest in my family, and yes, taller than my parents and also my older brother by a couple of inches. My family was quite well off, and I grew up in the south of England in a comfortable detached home with a large garden. I have a fairly posh accent being well spoken which contributed I think to many people assuming I was aloof although I was actually always just very shy and lacking in confidence, especially because I felt like I stuck out like a sore thumb being quite tall, and rarely spoke out loud if at all possible and I didn't mix easily. Some people at school would tease me, referring to me ask 'Plain Jane', which they would often utter in a monotone posh but boring voice which only added to my feeling self-conscious. I have light brown hair down to my shoulders and although not a beauty queen, have been told I have a pretty face, along with a fairly slim body with prominent 34c breasts, which I have noted were often the source of attraction for many men.

I was at university studying human biology, hoping to go on to further studies in medicine. My difficulties however began a couple of years previously when my parents broke the news to me that I was adopted. In a sense it wasn't a total surprise, I had become increasingly aware of how different I looked from my family, but the news was still quite devastating, and I had a huge row with them as I couldn't understand why they had not informed me before. I got the usual platitudes about them always thinking of me as their own child and as my father was often largely absent during my childhood as he was often away abroad for extended periods on business they had consequently put off finding the right time to tell me. This also meant off course that Marcus was actually my stepbrother. As if I hadn't dealt with enough drama just before I went off to university my parents also split up, once again not a total surprise as when my father was at home they often had terrible rows, but it did unsettle me considerably.

I was not a virgin when I went to university, I had had a couple of fairly disastrous encounters with men my own age before, which were far from satisfying and I was far from confident with the opposite sex and quite inexperienced. I had gone on the pill as a remedy for problem periods some time ago but didn't have an opportunity to enjoy the relative freedom that offered as I drifted through the first two terms of university, academically doing rather well but failed fairly miserably with the social life. I was not a naturally outgoing person and still rather shy and somehow despite a noticeable increase in my hormones which were frankly now raging, I could not bring myself to form anything like a romantic relationship, and satisfied myself with increasingly long bouts of masturbation, which I enjoyed immensely. I particularly liked to play with my breasts to start with, pulling gently on my nipples and stretching them out always got my juices flowing before progressing to use my fingers on my pussy or later discovering the joys of various vegetables, inserting mainly cucumbers or large carrots certainly did the trick and would bring me off with great satisfaction but equally somehow caused me much guilt.

My first sexual experience during university was with an older married man, much older, in fact he was my personal tutor, Raymond Harris. Ray was about mid 50s and quite a nice-looking guy, fairly slim with short neatly groomed silvery hair. The first sexual encounter between us was in his college office, somewhere I had visited many times to discuss my work progress and sometimes just for a chat. He was easy to talk to and very intelligent and his confidence relaxed me. It was not unusual for us to discuss the human body naturally enough as this was my main subject, but I had noticed that on occasions he would point at various parts of my body to illustrate a point as we spoke. It all seemed such a natural situation that I never really questioned his methods until sometimes when I was back in my room in halls, I suddenly felt a little tingle of excitement as I thought back to a hand casually resting on my knee perhaps as he explained the joints in the leg. I confess that I began to fantasise about him when I masturbated to the point that I would often blush when I first saw him, and I think he picked up on this.

The first sexual encounter I we had however was one evening when I had a seminar with him. I had never been there of an evening before but as I arrived he apologised explaining that he had been so busy that this was the only time he could fit me in. He offered me some wine which I gratefully accepted, and we just talked and drank a little and I was feeling quite relaxed, especially as at this point I seldom drank much, and he filled up my glass again without asking me. I wouldn't normally drink that much but I was enjoying the slightly different atmosphere of an evening seminar and his company.

We were discussing BMI (body mass index) and he asked me to stand saying that it would be easier for him to explain using me as a model. I stood up straight in front of him quite obediently and he looked me over up and down studying my proportions and then he asked,

"Jane, could you remove your cardigan please, I can't quite make out your outline?"

"Oh, yes, sure."

I agreed and took it off and stood up straight again as he continued to stare at me, his hand to his mouth looking at me thoughtfully. It was getting to the beginning of summer and quite a warm day, so I was only wearing a light flowery blouse, which showed off a little cleavage and which was quite tight against my prominent bust and a denim skirt which came down to just above my knees. He stood up and came towards me and stopped about a foot away from me. He was about 3 inches shorter than me, and I looked down at him as I saw him quite deliberately looking straight at my cleavage. I suddenly felt a little thrill in the pit of my stomach as I sensed the atmosphere between us had suddenly changed to something a little forbidden. My heart rate started to increase, and my bust moved up and down a little as my breathing became a little heavier as he continued to stare straight at my breasts. Then I gasped a little as he just casually began to undo the buttons on the top of my blouse.

"Ray, what are you doing?"

I asked a little urgently, the wine now suddenly rushing in my head.

"Nothing to worry about Jane, I just need to get a closer look at something."

I couldn't speak for a moment, as I was suddenly frozen in slight shock as I looked down at him slowly unbuttoning my top and when he got to the last button he very casually opened up my blouse as if it were the most natural thing in the world revealing my large breasts clad tightly in my white half-cup bra. Almost immediately I could feel my nipples hardening against the thin fabric as he exposed me. He stepped back a little for a second and just nodded as if confirming something to himself and smiled gently.

"Ray...what?..."

I tried in vain to form a sentence, but my words escaped me and then he said,

"You have lovely breasts Jane!"

I was near dumbstruck and couldn't think of a reasonable reply and just answered almost automatically,

"Thank you."

He looked up and our eyes met as he asked,

"Do you play with them?"

Once again I was amazed at his directness and meekly answered,

"Erm...yes, sometimes."

"Hm, and do you like playing with them?"

He asked as he looked back down at them as they heaved even more dramatically as the tension mounted in the whole of my body.

"Yes..."

I said quietly. And with that he put his hands out and he gently caressed them through the thin material of my bra with his firm hands, and I whimpered audibly. He seemed to take this as a sign of my complicity, and he then put his arms around me and pulled me into him as he kissed me. To my shame, I didn't object and I returned his kiss with some enthusiasm, putting my tongue into his mouth and then I felt his hands behind me under my blouse undoing my bra which suddenly loosened and he withdrew from our kiss and quite rapidly pushed my blouse over my shoulders and down my arms and let it fall on the floor and then swiftly repeated the move with my bra with such confidence I didn't object and stood back once more to admire my now bare breasts, rising and falling from my excitement, my nipples almost achingly stiff in front of me as I allowed my tutor to get a close up view of me topless.

Suddenly he just dived in and began to suck on my nipples alternately, holding my breasts up from below with his hands as he lapped away on my nipples sucking me hard and I gasped. I was so taken aback and so inexperienced that the feeling was quite overwhelming, and I began to shake as I confess I came as he played with my breasts, which really shocked me, and I cried out loud as I thrust myself out to his eager mouth and wallowed in my shamelessness.

As I gradually calmed myself he stood up again and spoke, and as he did so I could see him undoing his trousers and I saw the first glimpse of his hardon against the lightly coloured fabric.

"Are you on the pill?"

"Yes."

I answered.

"Good."

Is all he said, and he cleared a few books and files from his desk with two wide sweeps of his hands as they crashed onto the floor, and he just grabbed me by the waist and placed me in front of his desk with my bottom leaning against it as I looked on a little nervous but incredibly excited as I felt my juices leak into my knickers. I undid the zip on my skirt without being asked and he paused a moment as he savoured the sight of my tall frame standing there in just my white panties and matching socks. He stepped forward again and quickly pulled my knickers down to my knees and pushed me back onto his desk. As I fell back my legs naturally lifted up over my head as I tried to balance myself and he took hold of both my thighs and pushed me back onto the desk, lying prone, my white panties stretched between my knees like a flag of surrender and as I looked down urgently I saw his erect cock in his hand now as he rubbed the tip against the lips of my wet hairy pussy and then just eased himself into me to the hilt with one slick thrust.

"Oh, God!"

I called out in amazement and pleasure as he proceeded to fuck me really hard with great enthusiasm and experience and I sensed he wasn't the biggest, but he certainly knew what he was doing with it, and I could feel how rock hard he was as he thrust himself in and out of my soaked pussy. I could actually hear my own juices squelching as he fucked me as I looked back at him holding up my legs with one hand and feeling up my breasts with the other as he enjoyed my body. I looked back at him open mouthed, hardly believing the sight in front of my eyes as Ray pounded in and out of me. Having had so little experience, despite the obvious wetness my pussy was still pretty tight and I really enjoyed the power of him stretching me and I felt his balls bouncing against my naked bottom as he fucked me and I came again, my legs shaking in mid-air as he held them and my pussy clamped around his hard cock in tightening rhythmic pulses as I felt him straining as his face contorted and I distinctly felt him shoot as he emptied his balls in me. We stayed like that, frozen in the moment savouring the thrilling sensations in our bodies as he looked down at me, some sweat dripping down his forehead and said.

"God, I've been dying to do that since the first day I saw you!"

I confess also to being mightily flattered in my naivety. That was by far the best fuck of my short life so far, but I had finally discovered that I really liked it after all, and definitely wanted more, and I certainly did get more, much, much, more!

I visited Ray in his college office many times after that, without much pretence of teaching and I allowed him to explore my body in great detail. He took huge pleasure in inspecting every inch of my body and could spend hours just playing with me, licking me out and I even began to enjoy him fingering and licking my arsehole, something that would have shocked and repulsed me previously, but he gradually corrupted my innocence and taught me to enjoy all sorts of pleasures of the flesh I would never have even contemplated before or even to that point thought possible.

I was a willing pupil and most eager to please allowing him to do whatever he wanted with me as in my naivety I had somehow managed to kid myself that he was in love with me, and he would leave his wife some day for me but that was certainly not the case as I slowly grew to realise. We fucked quite often of course, but he gradually seemed to take great pleasure in degrading me as I accepted all his increasingly harsh demands without question, such was my obedience. He would order me to parade around his office with nothing on except my knickers which he insisted I keep either around my knees or around my ankles and he also taught me how to suck his cock, something else I had tried briefly before and found rather unpleasant and almost disturbing, but with Ray I learned to really enjoy it, I wanted to learn and to give him pleasure because I thought I was in love and I was soon savouring the taste of his spunk as he took great delight in often coming in my mouth or even over my face. He would get me to either suck his balls, putting them completely in my mouth and then pull his foreskin all the way back to expose his shiny cockhead and then he would tell me to lick and suck it until he came.

He also bought a polaroid camera and began taking photos of me as he made me parade in front of him or position myself either half undressed or completely naked in very explicit poses sometimes covered in his sperm. I would be lying back in his chair or on his desk with my legs spread, holding open my pussy, sometimes with his sperm dripping out of me, or squatting by his desk with my naked breasts resting on his desk, sometimes also covered in his spunk. He must have amassed almost a hundred or so such photos of me by the end of the term.

The problem was, although I didn't realise it at the time, I really got to enjoy the things he did to me and the more he pushed me and encouraged me to perform further acts of degradation and humiliation the more I ended up craving them, the feelings he managed to release in me were so intense that there was nothing I wouldn't do for him and I soon became hooked, and like some kind of addict I would visit him sometimes unannounced and demand his attention, which I gradually sensed began to waver, and I could feel his interest slipping away from me, and in my desperation the more he seemed to push me away the more I tried to please him and the more willingly I happily degraded myself in front of him. As I sensed the affair coming to an end I was left crest-fallen and was quite angry at myself as well as him for being so naïve and allowing this all to happen, he had made me feel cheap, but also somehow strangely liberated from the old me, but also I had this nagging sensation deep inside me that I needed to feel the sexual release his acts had allowed me to feel from somewhere, and most probably needed to find it away from Raymond Harris.

Part 2

The impetus for this new little chapter in my life came from somewhere and in circumstances quite unexpected. I was talking to Sara, a girl from my course one day during lunch at the college canteen and she suddenly told me about an incident that had happened to another girl from our course.

"Hey, Jane, did you hear what happened yesterday to Beth?"

"No, what was that?"

"She got flashed by some pervert in the park!"

"Shit! Really?"

"Yes, she's OK, but she was a bit freaked out. She was in Harwood Park, you know, the big park across from the cemetery just reading by the top of the hill and this old guy came past with his cock out!"

"Bloody hell!"

I exclaimed.

"How disgusting! What happened exactly."

I asked, trying to sound horrified, but to be honest really quite intrigued.

"Well she was lying face down with her nose in a book, but she sensed someone walking back and forth about 20 feet in front of her and as she looked up she saw this old bloke just standing there smiling at her with his big cock hanging out of his trousers, the dirty sod, and when she looked up at him he waggled it about in front of her."

"Christ, how awful!"

"Yeah I know."

I suddenly felt strangely excited however and had a terrible urge to know all the details.

"You don't think he was some rapist?"

"Oh God, no, nothing like that, thank Christ, just some sad little man waving his big dick about. Apparently there are often some weirdos up there doing stuff like that, hanging out by the trees and the bushes at the top of the hill, or so Beth was told later by another friend. Anyway she just yelled at him to fuck off or she would call the police, and he disappeared pretty quickly after that."

"Oh...was it big then?"

Sara looked at me slightly curiously and I hastily added as I didn't want to arouse any suspicion.

"You know, I mean did he have an erection?"

"Oh, no not really, it was sort of semi I suppose."

"But it was big?"

Sara paused again and said looking at me still a bit strangely, but then chuckled and said.

"Well yes, apparently he was hung like a horse!"

And started to laugh. I blushed at the thought of seeing a great big cock out of the blue like that and quickly took a sip of coffee to try to cover my blushes.

"Oh, you interested then?"

Said Sara half-joking.

"Er no thanks! No, my coffee's just a bit hot."

I said, fanning my face and trying to look nonchalant.

"Right."

Said Sara.

Harwood Park was a twenty-minute walk away from where my halls of residence were and I had been there a couple of times before but only around the far end by the river, and it was pretty big. There was a lake in the middle and then hills up towards the back some distance away and some heavily wooded areas along the top.

Yes, OK, so I did go there the very next day with a few books and read and wandered around a bit but nothing untoward occurred but yes, I was half hoping to see a nice cock. It was a lovely place though and I started to go there quite often after classes just to study. It was in the second week however when something unusual did occur.

I was at the top of the hill by the woods, a fair few people around in the distance walking and playing football and I was happily sat down reading with a flask of coffee and some snacks when I saw a guy approaching from the far left. He had come up the hill and was now walking parallel with the woods towards me. I continued to look down at my book but kept a look out from the corner of my eye. He came up quite close to me and I saw him much more clearly. He was a bit older than I had thought initially, maybe mid-40s, casually dressed in loose jeans, shirt and a peeked cap on. He looked down at me as he walked past quite close and smiled pleasantly and half nodded and I just sort of half smiled back and he went past and sat down still fairly close, directly in front and slightly downhill from me about 20 feet away.

He lay down on his side facing me and lit a cigarette and then casually looked all around and then looked back at me. I was sitting with my knees up resting my book on them wearing my denim skirt and a loose blue blouse. I tried to ignore him but realised he was looking quite intently in my direction. I wasn't unduly concerned as there were still plenty of people around certainly within shouting distance should needs be. It suddenly occurred to me that from his vantage point just downhill he could probably see up my skirt, so in a sudden panic I put my legs down flat and looked up from my book directly at him. He smiled back blowing smoke from his cigarette and just sort of waved his head back and forth in a sort of 'oh well' kind of manner.