Penny's Tales - Story 02

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The first time I submitted to Him, He took my anal virginity.
3.5k words
4.03
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Part 2 of the 2 part series

Updated 09/22/2022
Created 03/13/2013
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_penny_
_penny_
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-- Firstly, thanks to all who commented on Story 01. I'm sorry I can't please everyone. All your feedback is taken into consideration but these are true accounts of my experiences, so there's not much I can do about the plot line. I'll be adding to Story 01 soon.

This is a different section of my saga covering the first time I submitted to my first Master. I've changed details only to protect those involved and I was 18 at the time. --


I was bored. I had half an ear out for the lusty grunts of the completely average bloke between my legs but the majority of my focus was just above and to the right of the TV. Futurama was on, but I can't remember which episode. I'd escaped in my head, to a place where a tall, hairy and grossly over-muscled god was fucking me in a way I couldn't ignore.

Unconscious of my disinterest, my partner was on the brink of climax. The increase in volume snapped me back to the moment and I faked yet another orgasm to drive him over the edge.

Thirty seconds later, I was back in the few items of scant clothing which layered over the top of my scandalous underwear. I tidied my dark makeup as he lay on the bed panting. Tossing my curls to emphasise the just-fucked look, I felt the usual rush of pride and shame as I ran my eyes over his soft, sweat-sheened flesh.

One last glance in the mirror to confirm what I already knew - I looked like sex itself - and without another word, I grabbed my bag and headed out the door, down the stairs and into his mother's shop. Her eyes blazed furiously at me, and I grinned wickedly and strode out of the front door onto the street.

I blinked a little in the stark November sunlight and sparked up a menthol. I could feel my veins buzzing with white hot lead and a feeling of invincibility. My cigarette shortened noticeably as I took a long pull and started a leisurely meander back towards college.

A muffled alert sounded from my bag and I fumbled the catch as I retrieved my phone and a pair of large, dark sunglasses. As I unlocked the ancient Nokia, I prayed it was Him. With a few words, He could set my soul on fire and make me feel alive. During these times, it seemed like He was the only one who could keep up with me.

Alas, it was just a college friend wondering where I was. I flicked the butt of my cigarette into the road, lit another and picked up the pace.

***

I was finally summoned a week later. My heart was in my mouth as I sat on the train, nervously crossing and uncrossing my legs as my fellow passengers tried to get a glimpse up my indecently short skirt. I played with my trademark white suspenders where they joined my semi-sheer white stockings. Black and white striped knee-high socks and a pair of pinstripe Iron Fist heels completed the look. I emphasised my naturally dark chocolate curly hair and pale complexion with dark eye makeup and scarlet lips. I knew I cut the figure of a perfect little gothic princess. My tits were a little smaller than I would've liked, but I still to this day have an amazing ass and shapely legs.

I was a bundle of nerves but at the same time confident I looked stunning. This was my first time with Him and I had made myself perfect.

I lit a menthol as I disembarked from the train and took a deep drag. The train left swiftly and I was the only one on the platform. It was pleasantly cool for June; the cloud overhead kept the heat of the sun off but it was still a bright day. I slid my sunglasses off my head down over my eyes and headed up the steps to the footbridge across to the other side of the station. I reached the top of the stairs and froze.

There He was. Achingly handsome with long dark hair and a menacing goatee, dressed in black jeans and a long black leather coat. He was tall, maybe 6'3, and slender. His eyes were hidden with dark sunglasses but His mouth twisted in an amused smirk. He raised an eyebrow and beckoned. 'Come.'

Ryan's voice was deep and quiet, but commanding. He was used to being obeyed and I wasn't about to defy Him. As I tottered towards Him on my silly heels, He turned and began to stride away, down the stairs and out of the station. I had to half jog to keep up. In the car park out front was a slightly battered black Toyota Celica and He held open the passenger door, gesturing for me to get in the car.

I took a last drag of my cigarette, my hand trembling as I dropped the butt to the floor and ground it into the tarmac with the toe of my shoe. He saw my hesitation and grinned evilly. 'Last chance to run away, missy. Although I've made up My mind that I want you, and you won't get far in those shoes. So probably best to get in the car of your own free will.'

His words burned into me and I could feel myself growing damp. I though of turning and running just to have Him chase me down and brutally take me. I mentally shook myself - He would brutally take me anyway and I so badly wanted to please Him, to be a good girl.

'Penny...' There was a warning tone in His voice and I looked up at Him, realising I'd been day dreaming for a second too long. 'Get in the fucking car, now, before I make you.'

I nodded and scurried to the car, ducking my head to lower myself into the passenger seat. Ryan grabbed my hair and I shrieked. 'Rule one is that you'll address me respectfully. "Sir" will be appropriate for today.' His tone of voice was reasonable but His fist was tightening in my hair.

'Yes, Sir,' I breathed, tears welling up behind my dark shades. He pulled the glasses off me with His free hand and put them in a pocket.

'Ah, I forgot you had green eyes. Look how they sparkle when you're in pain.' I pressed my thighs together and bit my lip to stop myself from moaning. He pulled my face to His and mashed His lips against mine, thrusting His tongue between them and taking possession of my mouth.

Hours later, it seemed, He released me and I dropped into the leather of the passenger seat. Ryan shut the passenger door and walked around to the drivers side. He hopped in, agile for someone so tall, and the engine purred into life.

The journey to His house was uneventful and I won't bore you with the details - they're not why you're here after all. Suffice to say, we had a lot to talk about as we shared friendship circles and interests.

Some time later, we pulled into the garage. I reached for the car door handle. 'Ah! Stay.' Ryan got out of the car and walked around to the passenger side, opening the door for me. I stepped out and straightened up and He pressed against me, holding me against the car. I looked down and away but He gripped my jaw and turned my head up towards Him. He pressed His knee between my legs and forced them open as He leaned in for another violent kiss.

I parted my lips for Him and let Him claim me, relaxing my body into His. Ryan broke the kiss and pushed His sunglasses up onto His head, sweeping His long hair out of His face. His black eyes searched mine. 'Do you submit?' He almost whispered the question.

My chest was heaving and I could feel my cheeks flush with the warmth I felt deep in my core. This was my first real BDSM experience, He was my first Dom and I was excited and terrified all at once. It took all of my courage to reply. 'Yes, Sir, I submit.'

Ryan took my wrist in His hand and firmly led me into the house, up the stairs and into a modern, simply decorated bedroom. 'Take off the skirt and the top.' He crossed the room and pulled open a drawer, retrieving four cuffs and lengths of rope as I slipped out of my attire. 'On the bed, on all fours. Quickly.' He swatted at my ass as I hesitated, and I yelped and dashed to the bed, positioning myself as instructed.

My wrists were pulled together and the cuffs were fastened around my them with practiced precision. I wondered how many other girls He'd had at His mercy over the years. The thought of being at the hands of this experienced older man made me tingle all over and I spread my legs a little, rocking back and displaying my ass.

His hand came down hard on a cheek and I jumped forward a little. 'If you want to tease Me, I'll make you regret it.' Ryan murmured in my ear, running a hand down my body until He reached my ankles. These too were cuffed but then spread wide, with each affixed to corners of the bed. I could feel my wetness pressed hard against my thong, soaking through it.

Ryan mounted the bed in front of me, unzipping His jeans. I wasn't ready for the monster cock that was released in my face. He was thick and around nine inches long. Having me open and vulnerable on the bed must have pressed His buttons because He was rock hard. He pressed the tip against my lips. 'I take it you've done this before?'

I nodded and looked up at Him, opening my mouth to say 'Yes, Sir.' But as I did so, He roughly shoved His impressive length past my lips and into my mouth, hitting the back of my unprepared throat and causing me to choke. I panicked and tried to draw back, but He gripped the back of my head and held me still as He withdrew and then thrust in again deeper.

I gagged and retched as He continued to fuck my face, smearing my lipstick down His shaft. He held His dick as far down my throat as He could go and I struggled against Him, unable to breathe. 'Stop. Stay still.' His voice was firm if a little breathless. I fought against my urge for self preservation and stilled, my lungs burning.

Ryan pressed His thick cock harder against the back of my throat and His eyes met mine. 'Squirm, I dare you.' I held His gaze and resolutely did not move, even as I felt the room go fuzzy and start to get dark around the edges. Finally He pulled out and I fell forward, gasping for breath.

He stroked my hair. 'Good girl, very good girl. You really are very obedient. You like pleasing men, don't you?'

I nodded into the bedding and turned my head slightly. 'Yes, Sir' I gasped.

'But men are weak these days aren't they? They're all worried about you, are you enjoying yourself, have you orgasmed, are you uncomfortable. And you just want a real man, who takes what he wants from you, uses and abuses you.' Ryan unclipped my bra and let it fall down, trapped around my wrists by the cuffs. His fingers found my pierced nipples and began to twist and pull at them. 'Isn't that what you want, Penny? An experienced older man who'll plunder your young body and leave you bruised and spent?'

'Yes, Sir,' I groaned, slick between my thighs as He tugged at my sensitive nipples.

'Lucky for you that I found you. Now show Me what you can do.' I eagerly took Him in my mouth again, sucking Him down firmly and running my doubly pierced tongue along the underside. I took Him deep, struggling to control my gag reflex, and on the way out flicked my tongue over the tip.

Ryan groaned and stroked my hair. With His encouragement, I took Him deeper each time, listening to His moans and feeling His body's reactions to each placing of my tongue, each pressure I exerted. My piercings running over the spot just under the glans made Him gasp and twitch, so I used it sparingly. His moans were loudest when the head was pressed at the back of my throat and I tried to swallow. I worshipped His cock, growing wetter minute by minute as I pleased Him. My jaw trembled with fatigue and it started hurting so acutely but I refused to stop until told.

When I thought I could take no more and that my jaw would seize up, He stopped me and pulled out. He tilted my chin so He could look me in the eye. 'You really do want to please Me, don't you Penny?'

I smiled, 'Yes, Sir. I'd do anything.'

Ryan climbed off the bed and took something out of the pocket of His jeans. There was a metallic clicking noise and then a swish and my thong fell away in pieces. His long fingers were pressing against my slit, sliding up and down over my clit. I pushed back against His hand, hot and dripping with need.

'You've had a few men defile your filthy, tight little cunt, haven't you?'

I nodded, blushing furiously. My sex drive was insatiable and I hopped from bed to bed trying to find someone who could satisfy me. 'Yes, Sir.'

'What about here?' He pushed a finger lubed in my own juices against my virgin asshole. If my ankles hadn't been tied, I would've shot off the other end of the bed. As it was, I fell forward on my face, kicking at my restraints. A loud, hard slap rang across the back of my thigh. 'I think I know what to read into that, but answer Me respectfully. Has any man claimed your ass?'

I shook and sobbed into the bed. 'No, Sir.'

'Good.' Ryan grabbed my wrists roughly and pulled them under me between my legs, fastening them to my ankles and then to the bottom of the bed. I fought against Him, but He was strong and caught me off guard. 'I thought you said you'd do anything to please Me. Were you lying, Penny?' I turned my head to the side and could see Him from the corner of my eye, still fully clothed with just His jeans pushed down and that enormous member hard and threatening.

I thought for a minute. I did so badly want to please Him; I felt the need burning deep inside. I had always been submissive to my boyfriends, performing tricks in bed to fulfill their fantasies. I felt ashamed when I thought about the things I did, the humiliation I put myself through. And never had a single one said those two words I longed to hear. This one thing I had always said 'no' to was now the one thing I could do for Him which would validate my existence in the way I so desperately needed.

I relaxed against my bonds. 'No, Sir, I wasn't lying. I'm sorry, Sir. Please, do whatever You want with me. I just want to please You, Sir.'

I felt Him get on the bed behind me and push His cock against the entrance to my cunt. I sighed in relief that He'd decided to pity me - until He started to force His way into me. I was young and tight and as He pushed into my soft, hot wetness I felt a sore, aching, ripping sensation I hadn't felt since my first time two years before. He barely got half of Himself inside me before He hit against my cervix.

'Ah, and there's the target.' There was laughter in His voice but I had no idea what He meant until he pulled out and rammed His was back in again, battering against the deepest part of me. I yelped and tried to move away but was awkwardly restrained and unable to escape.

Again and again Ryan thrust into me, each time stretching me a little further by ramming against my cervix. I could feel myself bruising internally, but it felt so good. He was so long and thick He stimulated every inch of me inside, and the friction was building my climax.

He could feel me grow tighter and He bent down over me, breathing hard in my ear. 'Tell Me when you're close, slut.'

'Yes, Sir.' I took several deep breaths before He resumed His assault. A dozen thrusts later and I was on the precipice, feeling the most intense orgasm of my life just out of reach. 'Oh Sir, I'm so close, I'm nearly there.' I cried out.

Ryan stopped and pulled out. 'Please,' I whined, 'please don't stop, Sir, I'm so close, please.'

'Oh, I'm not stopping.' the tip of His cock was suddenly pressed against my forbidden entrance.

I tensed up. 'Please no, please don't.' I begged.

'Please don't?' He mocked me, increasing the pressure, gripping my hips to hold me still as I tried to buck away. 'But just now you were begging Me not to stop. Just now you said anything.'

I went silent and then hanged my head in shame.

'Do you really want Me to stop?' Ryan's voice was serious now.

I knew I should want Him to stop. I should want to escape the pain, but I wanted those words so badly. 'No, Sir.'

'I'll ask you again, do you submit?'

'Yes, Sir.'

'Then relax, it'll be better for you if you don't tense up.' With those words and before I had time to action them, Ryan pressed forward hard into my virgin ass.

I squealed and tried to push Him out but that hurt more. He gasped, 'Oh fight against Me, it'll hurt you but that feels so good and so tight.'

I relaxed and the pain eased off as He continued to bury Himself inside me, but I couldn't shake off His words. He liked it even more when I was tighter. I gritted my teeth and pushed against Him as He finally buried His whole length in my ass.

The pain was extraordinary and I felt sure I would tear apart as He pulled out and thrust, slightly harder and faster each time. I lost concentration for a moment and relaxed and for a few thrusts it started to feel good. Ryan tightened His grip on my hips bringing me back to reality and I pushed against Him again. This was not about me and I felt so ashamed for forgetting that for a few seconds; it was so selfish and bratty.

He fucked me harder and the pain was worse than before, but I could still feel my climax building. It was the strangest sensation of pain and pleasure accumulating and I was quickly reaching the brink. 'Sir, I'm close.'

The ass fucking lost none of its rigour. 'Ask nicely, slut.'

I screwed shut my eyes and swallowed hard, trying to control myself. 'Please may I cum, Sir?'

The pause before He answered drove me insane. It was probably only a few seconds but it felt like years. 'You're mine. Now, cum for Me, bitch.' Ryan commanded.

It felt like my universe imploded and exploded as I orgasmed hard, crying out something unintelligible. My spasming sent Him over the edge and with a grunt He buried His pulsating cock up to the hilt and emptied Himself inside me.

Ryan twitched for a minute or so before His softening dick slid out of my well-fucked ass. I gasped at the raw, empty feeling. I watched Him pad out of the room, zipping up His jeans, and I heard Him head downstairs.

My wrists were comfortable in the soft cuffs, but my legs were beginning to freeze up from being curled up underneath me for so long. The sweat on my body was starting to dry off and I was cooling down uncomfortably quickly. There was a clock somewhere in the room, but I couldn't see it and the ticking was driving me mad. When Ryan still didn't appear, I started counting the seconds. Three minutes, then five, then ten.

It was almost half an hour later when He finally reappeared in the doorway. By this time I was a shivering wreck, His seed slowly trickling out of my ass and down my slit, pooling on the bed beneath me. I didn't move when I saw Him, I didn't make a sound. I was His toy and He'd put me away when He was done with me.

Ryan roughly untied my bonds and slapped my ass hard. 'Bathroom that way,' He said, pointing, 'get yourself cleaned up.' I stumbled towards the door with numb legs. 'Wait.'

I stopped and turned to face Him. He walked towards me, towering over my five feet and four inches. I craned my neck to look up and Him and He leaned down to kiss me. 'Good girl.'

_penny_
_penny_
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AnonymousAnonymousabout 11 years ago
Excellent

All I wonder is-- which month is it? You say it is November, then a week later it is June.

Wonderful writing, and much hotter than a lot of the made-up stuff on here.

VanillaExtract apparently hasn't read much BDSM. The choices to capitalize references to the Dom and not-capitalize for the sub really alter the mood of the story and tell a lot about the characters and the author.

VanillaExtractVanillaExtractabout 11 years ago
Take a Penny, Leave a Penny

Mmm, enjoyable. I liked this a lot. The fact that you preface it as a true story makes it somehow more exciting, like anything could happen, good or bad. I like the bad. My only complaint was your capitalization (capitalisation? :) of "Him" or "He" or even "You" to refer to your master. Grammatically, it was unnecessary and somewhat distracting. The only place I've seen this type of capitalization used is in scripture, which is where it should stay...unless you're fucking Jesus Christ >=D Just my opinion though. Good writing otherwise.

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