Rebecca's Ruin - Riding High

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Overconfident girl is obsessed with good looking neighbour.
  • June 2022 monthly contest
11.4k words
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JennyGently
JennyGently
3,298 Followers

Where did it all begin, my road to ruin? What was the first step on the path that has since led me into a career that has no place on a nice girl's curriculum vitae?

My grandmother has a number of sayings. Two of them seem to sum up my situation perfectly:

'Curiosity killed the cat' and 'Pride comes before a fall'.

I was both incurably curious and unjustifiably proud that bright summer morning as I climbed out of bed. Barely eighteen years old and with a nice, feminine figure, good-sized boobs, long blonde hair and blue eyes, I would soon leave school before going to college in the autumn and I thought I was the dog's bollocks, as we say here in the English midlands.

As I opened the curtains, the sun flooded my pink-painted room with light. I blinked then looked out at the blue sky, the green trees and the shining windows of the houses close by -- especially the large ranch style property on the right.

Mr. Owen's house.

Like so many pretty girls learning the effect their looks could have on those around them, I was used to my developing body attracting the attention of male friends, teachers and neighbours and took advantage of it as often as I could:

'Oh pleeease could you give me a ride to the shops, Mr. Jacobson...'

'Pleeease can I have another week to do that assignment Mr. Mackay?'

I was sure some of our neighbours surreptitiously watched me sunbathing in the back yard too when their wives, mothers, sisters or daughters weren't around. I chose my bikinis carefully to ensure they could see just enough of my body to keep them interested, but not enough to give me the 'reputation' that in fact I justly deserved!

After all, I was supposed to be a nice, polite girl. I came from a nice, polite family and lived in a nice polite place.

The exception to the universal admiration I desired was Mr. Owen. For some reason my youthful charms had never quite worked on the rich, attractive and surprisingly young man who had moved into the house across the road a year ago. This rankled.

In his late twenties and younger than our other neighbours, Nick Owen was gorgeous. Tall, slim, expensively dressed and with a well-trained physique, he was closer in age to me than to my parents but that didn't stop him becoming a good friend of theirs and a regular guest in our house.

He was bright, witty, entertaining and very attractive indeed but never seemed to take anything more than a polite interest in me no matter how much I flutteredmyeyes at him, used my 'sweet baby' voice or sunbathed in my tiniest bikini where he couldn't avoid seeing me.

I knew he wasn't gay; there had been many female visitors to the house over the past year and I was more than confident in my own attractiveness so his indifference seemed unnatural.

My teenage pride was offended. I decided to find out more.

At first I simply watched the movements in and out of the house. There weren't many; every month or so he would pull up in his car with a new young woman and the two of them would go inside. The girls were usually the same type; long hair, large boobs, attractive if a bit 'tarty'. Some left the same day, some to my disappointment stayed overnight.

This made me envious. Though inexperienced sexually, I was not a virgin and would have rather liked to know what a night in bed with Mr. Owen was like myself.

Soon I got bored with merely watching and began to find excuses to drop by his house whether he was there or not, to see what else I could discover. But, apart from finding out that his house was very clean and tidy, I discovered frustratingly little of interest.

In was at a barbecue in late June when the breakthrough came. During the afternoon, Nick told Mum and Dad that he was going on business for a week and asked if they would keep an eye on the house while he was away. They of course agreed without hesitation and the following day he dropped round a bunch of keys and the code to his alarm.

As luck would have it, I was alone in the house when he arrived and happily accepted the keys, offering him a cold drink which to my delight he accepted. We chatted for a while during which I used every trick in my repertoire to try and flirt with him but without success. Though friendly and polite, Nick remained steadfastly immune to my charms so I was both frustrated and baffled by the time my parents arrived home and he had thanked them for their help before returning to his own house.

What was it that prevented him being interested in me? I didn't need to ask why I was interested in him, apart from his undeniable good looks his apparent indifference was enough to drive any girl as conceited as me to distraction.

As I closed the door behind him with my most alluring smile on my face, I had an idea. I ran upstairs to my room and made a phone call, cancelling my date for the weekend to the extreme frustration of the boy concerned at the time who had wrongly believed himself to be 'on a promise'.

***

It was late Sunday afternoon when Nick left for his trip. I watched his car pull out of the driveway and then paced up and down my room untilmyparents left for their usual trip to the gym.

As soon as their car was out of sight, I ran downstairs, grabbed his keys from the kitchen drawer and skipped over to the house. A turn of the lock, a few beeps on the alarm keypad and I was inside, alone with the door locked behind me, leaning against it while I caught my breath.

Was anyone there? I called out but there was no reply.

Nervously at first then with increasing boldness, I began to explore the house. My curiosity was uncontrollable as I snooped around looking for anything that would help me understand my gorgeous neighbour a little better and, if I played my cards right, get to know him a lot better too.

The lounge and kitchen were disappointing. Smart and expensively furnished, I couldn't find anything any normal, professional man his age wouldn't have. There were CD's, DVD's, a PlayStation and a bookcase full of action novels.

Dull but perfectly normal! My frustration returned but it was for too soon to give up.

With butterflies in my tummy, I slipped off my trainers and padded upstairs to find a large galleried landing with several doors, one of which was wedged open.

It was the bedroom! His bedroom! My heart thumped as I silently slipped inside. The room was large, tidy and modern, with a very large bed, a walk-in closet and... and no feminine touches at all.

My pulse raced.

I looked through the bathroom cupboards. There no evidence of female occupancy there either! He was unattached as well as gorgeous; I might be in with a chance; if only I could make him see how pretty and sexy I really was!

Emboldened, I began to open cupboards and drawers but to my disappointment found only neatly folded, expensive clothes. The boxes in the closet revealed nothing of interest either and I had all but given up on my search for scandal when I pulled opened a narrow drawer just below the wall mounted wide screen TV.

Inside was a small stack of unmarked DVDs. What were these? Porn? Was this a first secret find? I slipped a disc into the machine, waited for it to load and pressed 'play'.

The screen burst into life and a few moments later a young girl's face appeared in extreme close-up. Her mouth was open, her eyes wide and staring and her body was trembling in extraordinary climax.

It was porn! Nick Owen was human after all!

A thrill of triumph shot through me. The man did have secrets after all; maybe if I understood more about his tastes I could make myself more like the kind of girl he liked. A broad smile on my excited face, I lay back on the bed to see what sort of porn my soon-to-be-boyfriend was into.

Even at this young age I was no stranger to Adult Movies. At many of the sleepovers I had been to, once the parents had gone out or gone to bed my friends and I would watch DVDs 'borrowed' from those parents or brothers late into the night with the sound turned very low.

Most of the movies had been trash with useless plots, unattractive studs and overblown orange-coloured girls. We had laughed ourselves silly. But others had been seriously arousing; I especially liked the 'real life' stuff where no attempt at a plot was necessary. Movies in which well endowed, good looking men would visit real lonely housewives and fuck them within an inch of their lives in their own homes, or movies in which real girls would expose themselves in public.

But the movies which turned me on most were those where real women would reach massive orgasms on sex machines on camera.

I was fascinated by these machines. More than once I had borrowed the thick, battery-powered dildo my mother thought she had secretly hidden in her bottom drawer. It had brought me a surprising amount of pleasure without the need to tell it the tedious ego-supporting lies boys always needed to hear even after very average sex.

Since then I had acquired a small stash of my own toys, hidden in a bag under the corner of my bed. I used them frequently if secretly to 'take the edge off' when I really needed an orgasm -- which as I was an energetic eighteen year old girl, was often.

Of course, a girl as hot as me could have called in any one of a dozen boys to do the business but apart from not wanting to get a 'reputation', in my albeit limited experience no boy could come even close to giving me the intensity of climax these devices reliably and routinely induced in my demanding teenage loins.

There had been a lot of frantic fingering under the duvets and moaning into in the darkness both during and after these sleepover movies. Often the fingering had been mutual but this was usually followed by shame-faced embarrassment the following morning over breakfast when no amount of washing could rid a girl's hands of their distinctive fishy smell.

To my sheer delight, it seemed that Nick was into this type of porn too. I hadn't expected this at all. Once he knew we had this much in common he couldn't possible resist me. The discovery made me want him even more.

I settled back on the wide, comfortable bed and watched the programme spellbound as the trailers ended and the movie began. The video was good -- very good. The girl on the screen wasn't much older than me but what a time she was having! At first she had just been fingering herself but then an unseen hand had passed her a large dildo and the big build-up of arousal had started.

Within minutes I had raised my short skirt and slipped a hand inside my panties. Five minutes later my panties had been lowered a few inches to give my hand more room to work as the aroused blonde on screen was joined by an equally good-looking brunette.

A short time later my fingers had slipped deep between my thighs as the two girls began to ride 'sybian' sex machines side by side while the director and his crew watched and filmed.

Though young, the girls were clearly already hardened porn actresses but despite their tattoos, piercings and cynicism, the machines were still able to bring them to incredible and very obviously genuine climaxes within minutes.

One girl even began to cry on camera as spasm after spasm racked her body.

By now my skirt was up around my waist. I pulled my panties quickly down over my knees and kicked them away then leaned back against the padded headboard. I spread my legs parted wide and rubbed my fingers on and in my slit.

As the buzzing of the machine's motor on the screen rose and the girls' on screen speech became incoherent, my fingers became a blur. My outer lips were already puffy and parted, my clit standing firm and proud between my eagerly working fingertips. As the dark haired girl on screen reached a third massive screaming climax, I reached my own slightly smaller but no less wet one on my gorgeous neighbour's bed.

"AaayyyyYYYYYYY!"

The girl on the screen was screaming too as she came again and again, her helpless body supported by one of the cameramen. I climaxed with her, then rolled face down on the bed and thrust my bunched fists into my groin, curling my fingers up into my body. My face buried in the duvet, I finger-fucked myself frantically, rubbing my engorged clitoris to a second, stronger, shuddering orgasm, then a third.

"YYYYyyyyyyYYYYEEESSS!"

The blonde on screen finally reached orgasm too, the recorded squealing from the two girls' combined, obviously genuine climaxes joining my own animal exclamations as I howled my final orgasm into the mattress.

The DVD ended. I fell silent on the bed, panting from unplanned but incredibly powerful orgasms I had given myself. No stranger to masturbation, their intensity had astonished me. The high quality action on screen had been much more arousing than I had expected. It was clearly time to put together a small collection of my own.

As I slowly returned to earth from the height of my climax, I began to realise that a large amount of moisture had seeped from my vulva as I came. It was now all over my fingers, down the inside of my upper thighs and dribbling onto the duvet beneath my bottom. Frightened of staining the bed clothes, I reached across to the bedside cabinet hoping to find a tissue.

There was nothing on its surface but when I pulled open the top drawer I found an almost new box. I reached in to grab it but as I did, my fingers closed on something else. I pulled the object out; it was an uneven cylinder covered in soft pink plastic...

My eyes opened wide; it was a dildo; a real dildo. It was longer than any real cock I had ever seen and thicker too, with rough, irregular undulations all down its sides like veins and a smooth rounded head.

Unable to control myself, I broke into giggles, turning the plastic phallus over and over in my hands with glee. It was thick but not too thick, long but not too long. I upended it to see whether there was a switch to turn it on but found only a metal plug in its base that looked like it could be joined to something else, like a light bulb slotting into a socket.

For a moment I thought about using it; following my fingering with a little plastic penetration but realised I needed to tidy the bed and remove all traces of masturbation before the duvet was permanently marked.

So, my body still tingling with after-shocks, I put the dildo back in the drawer and padded downstairs to the kitchen, bare-bottomed, looking a little dishevelled and still distinctly aroused.

I had left my panties on the bedroom floor but as the house was empty and its owner far away, being bare in a strange place made me feel sexy and daring rather than vulnerable. Opening the fridge, I took out a can of Coke and sipped it as I began to explore the ground floor again.

Returning to the lounge, I turned on the big wall-mounted TV. Cartoons! Kids' stuff! Boring!

Abandoning the screen, I drifted towards the back of the house, finding a laundry room, a toilet, several large cupboards and a door to what must be the garage. I took another sip of my Coke, turned the handle and entered, searching for the light switch with my free hand.

Click! The room was filled with bright light.

If it was a garage, it was the cleanest, neatest, tidiest I had ever seen. It was warm too. The lighting was subtle, the floor covered with wooden tiles rather than cold concrete, the walls clean and painted white. Tool boxes and a work bench lined one wall while two bicycles hung from hooks on the other. Against the back wall stood a home gymnasium with weights and exercise machines; there was no dust or dirt to soil my white socks as I padded around exploring.

As I reached the corner furthest from the door, I found some kind of device or machine standing on a square of padded matting, covered by a dust sheet. Nick Owen looked like he worked out regularly; was this a home gym? If it was, it wasn't like any home gym I had seen before.

I pulled the sheet off and stood back, puzzled.

The machine came up to my waist. Its base was a low cylinder about two feet long; like a small barrel that had been split lengthways from top to bottom and laid on its side. Its surface was soft, padded and covered in vinyl. Along each side of the base was a trough with two straps. From one end rose a vertical metal pole that came up to my tummy and from which two padded horizontal 'arms' stuck forward. At the end of each arm was a hand grip.

I circled the machine slowly, puzzled, then ran my hand over the armrests. They were smooth. I grasped the hand grip. It felt comfortable and reassuringly stable, but I had no idea what it could be.

I knelt down and looked at the rounded base. It looked familiar; more like a saddle. I touched it and to my surprise found it warm and vibrating as if it contained a motor which was still turned on.

I looked closer. There was a round hole about an inch wide in the upper surface of the saddle with an odd shaped metal socket inside. I peered and stuck my finger into the hole but could find no clue as to what it was for. I was shuffling round on my hands and knees to get a better view when my fingers touched something lying on the mat.

I sat back on my heels and looked; a small silver case lay alongside the machine. I picked it up, popped open the clasp, lifted the lid then gasped. Inside the case were three recesses intended to hold and protect the contents. The topmost, smallest recess was empty but the other two held items that announced their identity in clear, unambiguous terms.

Both were long and thick, both had low, uneven ridges along their lengths, both were slightly bent with dome shaped ends

Jesus! They were dildos! Massive dildos!

My mouth dropped wide open. These really were dildos, but like no dildo I had seen before!

The smaller one was blue and far bigger than any real erect penis I had ever seen in real life or porn. The much larger, black one had a second smaller dildo stuck on the side!

Jesus, it was massive!

The empty space must be for the pink dildo I had found in the bedroom. Though it had felt big in my hand it was simply dwarfed by these two monsters.

Suddenly it all made sense. The DVDs; everything!

I couldn't control myself; I simply burst out in fits of giggles. Here, in the middle of Nick Owen's obsessively tidy garage was a real fucking machine, just like those I had seen in the DVD's but bigger and more complicated.

I rose to my feet and slowly circled it, my eyes wide in amazement.

The base of each dildo must fit into the socket. I picked up the huge blue phallus; it felt heavy and thick in my fist. I tried inserting its base into the machine's socket. After two or three attempts it clicked smoothly and easily into place and stuck vertically, obscenely upwards.

I stared at the device with new eyes. It was obvious where the dildo itself should go but what about the rest of the machine?

That pad at the base must be to excite the rider's clitoris.

Those side channels must be for her knees.

Those straps must be to hold her steady.

Those arms must be for her to rest against when she came.

Jesus! What kind of orgasm needed leg restraints, armrests and hand grips?

That dial on the end of the right arm with three different coloured settings -- pink, blue and black - must be the controls, a different setting for each dildo.

As I stared excitedly at the extraordinary device images of the DVD girls' faces as the machines had brought them to orgasm filled my mind. At the time I had thought it was all just acting but, seeing this machine, maybe it wasn't after all. Maybe there really were orgasms like that.

Oh God! I hoped there were!

Just imagining what the machine might be able to do was arousing me again. I knelt by it again and ran my fingers up and down the huge, blue phallus. It simply dwarfed my own toys; even Mum's biggest vibrator looked tiny in comparison.

JennyGently
JennyGently
3,298 Followers