A Dare To Myself (Chapters 1 & 2)

CHAPTER ONE

The bell rang loudly, the quiet room suddenly being filled with the noise of moving chairs and shuffling feet.

“Okay class, that’s all for today,” I called, trying to make myself heard over the fracas. “And no excuses this time please, Caligula wouldn’t have tolerated it and neither will I!”

I watched as the students continued to make their way through the exit, ignoring my rather poor attempt at humour. A few stopped to say goodbye, with a mumbled, “goodbye Miss Willis,” one hoped I would have a nice weekend and that was that. I walked over to close the door and then made my way back to the desk to sit down. A stack of papers awaited a grade and I knew I had a limited amount of time to get them done before the inevitable itch to get home became too good to resist.

A good hour passed before this daily routine came to an end. It was an hour of frequent clock watching, occasional sighing and, once in a while, a piece of work was impressive enough for a smile to creep across my face. Very few students seemed to be grasping the concept of why we still taught Roman culture, instead choosing to giggle at their “strange” lifestyle or just ignore the lesson completely and stare at their phones.

With the last paper graded, I stood up and began collecting my things, placing them untidily into my bag. I stepped out of the class room and walked along the now empty corridors towards the teacher’s lounge. This too was empty, my colleagues much preferring to take their work home with them. Some liked this idea simply because it was Friday and tonight was for drinking, tomorrow for the hangover and Sunday for grading papers. Most preferred to take the papers home just so that they could spend some more time with their families. This certainly wasn’t an issue for me as I placed the work into my drawer and started the short walk towards the car park.

The sun was still shining, a warm breeze blew my long light-blonde hair as I moved towards my car. The janitor was sweeping the floor, but stopped to give me a smile as I walked past. I returned the smile, continuing to do so long after I’d passed, enjoying his attention. I’d always hear the students talking about how grumpy he was, so it amused me how happy he always seemed when I walked past. And yes, I do realize what made him happy, I just so happened to enjoy the attention!

The drive home was an uneventful one, filled with some rather poor attempts at singing along to some corny pop songs on the radio. I enjoyed my job, but there’s nothing better than the fading memory of a long week as a whole free weekend waited ahead of me. I was in a very good mood! I parked, walked through the front door of my apartment building and towards my home.

I now had to partake in another Friday night ritual as I opened the fridge and removed an ice cold bottle of white wine. I kicked off my shoes, poured myself a large glass and collapsed onto the sofa. Taking small sips, I allowed my head to fall back and rested my eyes. This may not seem particularly exciting for you and it’s not that I’m a complete hermit, but I did very much enjoy my own company.

I was 25 and single. I had a lot of friends, but they knew that if I hadn’t committed whole-heartedly to a night out then I was likely to stay in, so I was safe from any phone calls interrupting my peace. It also wasn’t like I couldn’t get a boyfriend, I just didn’t want one at this time. Also, the relationships never really lasted that long either, but we’ll get onto that a bit later.

I took the last few sips of my wine, enjoying the light buzzing sensation coursing through my body. I set the empty glass down, making my way towards the bathroom, unbuttoning my blouse as I stepped inside. As I undid the last button, I slid it off of my shoulders and allowed it to fall onto the floor. I turned the faucet of the shower on full and continued to undress, allowing the water to warm up. I moved my right hand to the back of my skirt, slowly moving the zip down and enjoying feeling of the air as it rushed around my bare thighs. Next I removed my bra, allowing my small breasts free as I threw it on top of the growing pile of clothes. Finally I slid my panties down and stepped out of them and straight into the shower.

I moaned softly at the enjoyment of the warm water flowing down my naked body. I allowed my hands to brush along the sides of my hips, down my smooth legs and back up. I knew I was attractive and loved playing games like this with myself, touching parts of my body that I knew many men would like the chance to touch. I continued for a little while longer, before eventually using the shower for it’s practical purpose and cleaning myself.

I turned the faucet off as I stepped out of the shower and straight into the gaze of the body length mirror in front of me. I struck a few poses, some fun, some sexy, all brief. Eventually I sat myself down on a towel and began to dry my hair, continuing my gaze into the mirror. My eyes looked slightly tired, but still had that blue sparkle that my mother always said would get me into trouble. I pouted my lips and tilted my head to the side, striking a few more poses for nobody.

After my hair was adequately dried, I slipped on my dressing gown and walked back to the sofa. I poured myself another glass of wine, took a sip and set the glass down again, replacing it with my laptop. Once booted up, I went straight to one of my favourite pages. An adult site, filled with reader’s fantasy sex stories. And this is why I never kept a steady boyfriend.

I had a very vivid imagination and a very high sex drive, but this seemed to be too much for any of my ex-boyfriends. I was sure I was fun to be around and I knew I was more than intelligent enough to keep conversation flowing, but the sex-life always suffered. And, as everyone knows, this is a very important part of any lasting relationship.

Things would always start out normal enough, sex being passionate and fun. But I was always quick to get bored and would try and bring more interesting ideas into the bedroom. I loved role-play, being fucked by a stranger being one of my favourite fantasies, but guys don’t really like the idea of this and I can kind of understand why! Just fucking and pretending that he was a stranger was never enough, I wanted it to be a two-way thing, but obviously it was always seen to be weird. Eventually the time we would spend together would lessen and the inevitable break up would happen. Not that the term “break up” ever had any merit to it with me, I was never particularly broken up about it. I would just move on, get into the next relationship and the cycle would start again.

The problem was that I could never actually bring myself to have a one night stand, or even a fleeting moment where I could act out this fantasy. I was brought up differently to that and, dare I say it, I was a snob. I always aimed to have a career. I owned my own apartment, came from moderate wealth. No, I would either act out the fantasy in a safe environment or not at all. Unless my head could do the rest and that’s where the laptop came in handy.

I browsed through hundreds of the thousands of stories on the site, scanning the titles quickly until I found one that met my tastes. I always laughed seeing what people would write about, but never judged. After all, I have my own fantasy that causes people to judge me in a negative way in my real life. These people were just letting their imaginations run wild and, as long as it didn’t harm anyone, then good on them. They just weren’t for me.

I finally settled on a relatively story that was pretty well written. It involved a young female escort who found she enjoyed the sex much more than the money. I rubbed my legs against each other as I read through her journey of fucking random perverts for little money. I admired her fearlessness, her lust-driven sense of adventure. I craved many aspects of her life, but knew I didn’t have what it took to do it. The very thought made me wet and that, as always, would have to do. As the story wound to an end, I picked up the wine and gulped the rest down and walked towards the bedroom, my mind swimming in a sea of eroticism.

I stepped into my room and lay down on the bed, spreading my legs, the dressing gown riding up and exposing my thighs as I brushed my fingers nails against them. I undid the tie to my gown, allowing it to fall completely open and exposing my body for my hands’ access. They hungrily rubbed and grabbed at my body, stopping only to pinch at my rock hard nipples. Each pull leading my back to arch and my hips to thrust upwards. I let the images of the story fly through my mind as my hands finally settled on my soaking pussy. I dipped two fingers and thrust them straight in to my wetness, my other hand rubbing left to right on my erect clit.

I allowed my mind to run wild as I imagined a man walking into my room, his cock already hard as he watched me bring myself off. There were no details to him, I couldn’t tell if he was good looking or not, even what his body shape or cock size was. At this moment it was just important that he was here. He was shortly followed by two others, just as vague as the first, hard dicks in hand and jerking themselves as they enjoyed the show. And boy did I give them a show. I alternated between letting my fingers do the work and thrusting up to meet them, either way I was starting to fuck myself extremely hard.

The men continued to masturbate, their gazes never leaving my wanton body as I writhed around in pure pleasure. The story that I had read was rapidly disappearing and this was now just for them. I could hear their breathe becoming rapid which just caused my excitement to double. I continued to rub my clit as I brought my other hand up to my mouth, the fingers soaked with my juices as I sucked them off and moaned at how good I tasted. Once I had cleaned them, my hand moved back down and grabbed hard at my tits.

My hips continued to reach up, pressing into my fingers as they kept up their relentless pressure on my clit. My moans became gasps as my breath began to quicken, taking short breathes as the pleasure wrapped itself around me completely. I could feel the first sprays of sticky cum splashing my body all over, warm and delightful as it dripped down my body.

The men were standing directly over me, shooting load after load of thick sperm across my tits and stomach. My orgasm was building to it’s peak as my mind continued to repeat the same message.

This could be real. I could do this tonight. I’ll just find someone and let them use me and have the best orgasm I’ve ever had. I can do it, I can be a slut. This could be real.

I cried out in ecstasy as my climax reached the final heights, my hand slowing down on my clit as my other hand found itself back between my thighs and started fucking my soaked pussy slow and deep. My body shuddered, jumping quickly as my clit became too sensitive to touch. I removed my hands, spreading my arms and legs out, letting myself use the full space of the bed, eyes closed and a smile across my face.

The images of the mystery men slowly faded from my imagination, but, to my surprise, the want of this fantasy didn’t disappear for once. It lingered and left a strong feeling of butterflies deep in my stomach. I began to shiver slightly, even though the temperature in the room was certainly not cold. The thoughts became more blurry as the exhaustion of orgasm worked and I quickly drifted off to sleep.

CHAPTER TWO

After some success, my sleep started to become a lot more restless as I tossed and turned in my mostly empty bed. My eyes slowly opened and I stared at the clock, blinking. My brow furrowed slightly as the realisation of it only being 5am hit me. I moved myself onto my back and closed my eyes again trying to find the sleep that I wanted so much. But my thoughts began to betray me and I became aware that the butterflies still remained in my stomach. I needed to fuck someone, anyone. I wanted it to be dangerous, I wanted to be a slut.

My pussy stirred, but as I began playing with myself I noticed that I wasn’t going to be able to get myself off. I couldn’t concentrate properly and it became clear that my thoughts just weren’t going to be enough. A wave of heat ran across my body, not unlike a feeling of dread, but there was nothing to be scared of here unless I actually acted this out. And I certainly wasn’t going to allow myself do that.

I tried to get back to sleep once more, but after around an hour of trying to name all of my students, counting sheep and anything else that might possibly help, my thoughts always returned to my aching pussy and the feeling deep in my stomach. Eventually I sighed loudly to myself and got out of bed, looking at the clock reading just past 6am.

After a few minutes of pacing around my kitchen, not quite sure of my intentions, I decided I would take a walk. There’s nothing a bit of fresh air can’t solve, I told myself as I started to get dressed. I opened my bedroom curtains to get a sense of the weather. It was mostly sunny, but it looked like it had rained over night. The shiny roofs of the parked cars in the street, reflected the sun brightly. Still, this would only make it quite stuffy outside so I didn’t need to wrap up or anything. I put on a vest-top, and a mid-thigh skirt over my panties. Once my heels were on I stepped out of the door and towards the exit of the building.

I had decided to walk to the park, hoping that the early Saturday morning would only bring a few dog walkers so that I didn’t have to listen to the high-pitched shouts of young children. I didn’t have anything against kids, my job would attest to that, but I was looking forward to a sit down on a park bench with just the sound of the birds for company.

There were a fair few cars making their way deeper into the city, but it seemed largely that my wish had been granted. As I came to the park and walked along the wide path towards it’s center, the birds were in full voice. The park seemed completely empty as I picked a bench to sit down on, leaning back and shutting my eyes.

The peace I had been searching for at night seemed to finally be winning over the lust that seemed so uncontrollable just a few moments before. The sun was starting to heat up as the few clouds disappeared and I enjoyed the feeling of warmth on my face. I would only open my eyes occasionally as the footsteps of a guy running pricked my ears. He seemed to be running laps, but every time he ran past he seemed to look me up and down. He didn’t seem to be trying to make it obvious, but he was definitely doing a bad job at it.

I tried keeping my eyes shut, but couldn’t help but open them to check that I still had his attention with each passing lap. It wasn’t a particularly big park so it would only be every couple of minutes that his eyes weren’t on my body. He was a little overweight and at the beginnings of middle-age, but his attention was starting to bring back the lust I had tried to repress. I wanted to see what he did when I wasn’t looking, so I decided to pretend to have my eyes shut, using the little vision to try and judge what he would do.

As he ran past this time, he definitely seemed to stare at me for longer, even turning around for a last glimpse as he ran further away. The feeling of heat began to return to my body and, it wasn’t just the butterflies I felt, I simply felt sick. This man was definitely a disgusting pervert, barely even trying to hide his gazes at me. But, with my mind telling me to just get up and walk back home, my pussy began to betray me. The same thoughts from last night began to creep back to me.

“Do it, you need to cum and you need to hard. Fuck this man and see how it feels. You need something inside you and he will do just fine.”

I genuinely didn’t know where these thoughts were coming from. I had always had this fantasy, but it had never crossed my mind that I would be in a position where I would actually act on it. I had always told myself that I was too good for it, but that just made it more exciting. What would my parents think if I did this? Oh god, that just made this more hot.

I saw that the man was running back into the distance again and decided to see how far I would go. It was time to test myself and see where this led to. I can always back out if this seemed too strange. I began to roll up my vest, letting it rest just under my braless breasts. My toned stomach now lay bare, with the shape of my small tits becoming even more obvious to anybody who wanted to see.

This time when the man past, he couldn’t help but stare in quite an obvious way. His mouth even seemed to open slightly, his eyes wide as he looked upon my body. He didn’t stop running, but he had noticeably slowed his pace as he past me this time. His head turned away, facing forwards once more and freeing me from his gaze once again. How had that felt? It felt so fucking good. There was no doubt that he had a stirring in his shorts and it was all because of me. It seemed like I was finally using my body for it’s purpose.

As my own wetness became more obvious to me, I had to act now. I felt like I had to do something to make sure that whatever this was that I wanted actually happened. If I didn’t do anything then this moment would be lost forever and I didn’t know whether I’d ever pluck up the courage to do it again. In fact, I felt certain that I wouldn’t. This time, as the man ran past, I wanted to seal the deal.

“Hey you,” I called out suddenly, as he turned with a slightly shocked look on his face. I smiled, mostly to myself at his reaction, but it definitely seemed like the right thing to do in this situation anyway.

He had stopped running now, standing still, staring at me in awe. It was probably because this had been going on for a good 20 minutes or so and I had said something out of nowhere. “Yes you,” I explained, standing up from the bench. I ushered him over with a finger and said, “come here.”

My excitement grew greater at the strange power I seemed to have, as he walked in a tired manner towards me. As he stopped, I noticed he was much taller than me. To be honest, a lot of people were, I’m only 5’2. “Can… can I help you miss?” He was unsurprisingly out of breath, and still seemed a little confused by this confrontation, keeping a few metres distance between us.

I placed a hand on my hip and gave him a look of disapproval, which definitely wasn’t false. As much as I seemed to crave the attention, I still disliked him for it as I asked, “So you like staring at women do you? You don’t think we should enjoy the quiet without dirty men like you staring at us?”

If he didn’t look shocked before, he definitely did now. His cheeks, already flushed from the exercise, seemed to go an even deeper red as he tried to stutter a response. “I wasn’t…. well it isn’t like you didn’t…. no wait, it’s just.”

I allowed my smile to return again as I interrupted him. “Shut up for a second,” I said sharply, enjoying the silence that he responded with as his mouth literally shut mid sentence. “I am going to give you an opportunity here that you will never get again. I am going to walk over there after I’ve finished speaking.” I pointed behind the bench where a thick row of trees lay. “You are going to follow me and you’re going to fuck me. I am going to cum and then you may cum. And once you’re done fucking me you can fuck off again.”

I managed to keep my own shock hidden inside myself as the words that I had spoken sank in. I only ever used such words rarely, training myself for years not to as my job permitted. What was I doing? His own shock was still very much visible. He gulped audibly and went to respond. “No,” I insisted, anticipating more confused nonsense to come out of him. “You don’t need to speak, in fact I don’t want you to speak. You simply follow me, or you leave.” With that, I turned around and started to walk towards the trees.

I allowed myself to turn around as I entered the visibly darker area and tried to keep my composure as I saw him following, mouth still slightly agape. I carefully stepped over twigs and fallen branches, still visibly wet from last night’s rain as my heels sunk slightly into the grass. The smell of damp only added to my lust. Around 10 metres in I stopped, standing next to a tree and turned around to face my mystery man.

He walked sheepishly over and just stood there, arms by the sides of his sweat-soaked t-shirt. He seemed to be slightly shaking and I realised I would, once again, have to take the initiative. Although, that was what this was all about. Knowing what I wanted and finally taking it. I walked over to him, grabbing him by his wet shirt and dragging him gently until I was back at the tree. I pushed him against it, his back hitting against the bark, but with no real force.

His courage seemed to grow as he leaned his face towards mine. He was not a particularly attractive man at all, certainly not my type. His stubble seemed to have a few too many gaps in it for my liking and his chubby face certainly didn’t do him any favours. I leant away from his attempted kiss. “I don’t want to kiss you, I only need this,” I stated as I rubbed my right hand against his crotch. He was definitely on his way to being fully hard, but there was still some delightful softness that I wanted to explore further.

I didn’t need to squat down far to bring my eye-line level with the front of his shorts. I brought my hands up to the hem and pulled them down. I could now see the outline of his cock and brought my face nearer as my lips caressed it through the thin material of his boxers. An audible sigh left his body as I shoved my right hand inside, wrapping it around his girth. I used my left hand to pull his boxers down, his cock springing delightfully as it was freed.

It was fully hard now and I was a little impressed. It wasn’t particular long, but it was slightly thicker than average for sure. I kept my hand wrapped around it as I brought my face to the side, closing my eyes as I let the meaty scent fill my nostrils. I poked my tongue out, and let it run the full length a couple of times. A high-pitched noise escaped his lips as I brought my mouth around the head and sucked lightly, looking up and meeting his sweaty gaze with mine.

As I removed mouth, I could see a thin string on pre-cum connecting my bottom lip to the slit of his throbbing cock. I began to move my move my mouth up and down and I felt his hand move onto the back of my head, not pushing me, but guiding me deeper with each downward stroke. Unfortunately for him, this was probably the best blow job he had ever had and he had just stopped it in it’s tracks. My juices were literally dripping down my thighs as my excitement reached heights I didn’t know existed. I felt like I would cum at the slightest touch of my clit and wanted this to be as short a wait as possible.

I removed my mouth, making an audible pop, his disappointment lasting just a few seconds as he realised what the next act would be. I pushed him to one side, again with no real force. He seemed to tower over me, even with my heels, but was openly letting me push him around as if to save my embarrassment. As if I cared. Facing the tree, I placed one hand over my head and against the bark and used the other to pull my panties down, stopping as they reached mid-thigh. I slightly bent one knee, and rucked my skirt over my ass.

I stared at him, making my frustration obvious as he stood still for a moment too long for my liking, before he finally moved up behind me. His hands grabbed my small waist and I noticed, for the first time, a ring on his wedding finger. I shook my head in disgust, which quickly disappeared as I felt his cock pushing against the slick opening of my pussy. He made a few poor attempts at entering until he finally managed it, clumsily pushing his thick cock into my soaked cunt.

My eyes rolled into the back of my head, thrusting back against him as he started a quick rhythm. His dick pumped quickly into me, in and out at full length. The sounds of his strange, frequent grunts entered my ears. The thought of this overweight, middle-aged man fucking me hard sending tingles through my pussy. This man has no right to have somebody as beautiful as me to himself, but I am letting him take me.

A gorgeous warmth wrapped around my body as he brought a hand round and grabbed awkwardly at my tits. In what only seemed like a minute, I was panting my way towards a mighty orgasm. Doing my best to remember I was still in a public place, I tried to stifle my moans as my climax shook through my body. His cock rubbed deliciously along the walls of my pussy as my knees buckled under the pleasure.

Time seemed to stop and I had lost all awareness as the feeling of his shaft became the only thing that mattered. Beads of sweat ran down the back of my neck, sending shivers down my spine as I once again became aware of my surroundings. The last waves of my orgasms washed over me and the sound of the grunting, disgusting man pumping into me returned once again. The enjoyment started to disappear as he continued for a few more moments.

His grip on my hips tightened, painfully as his balls smacked against my thighs with each hard thrust. He groaned a low, guttural sound as I felt his cum shooting deep inside of me. It must have been a while as it seemed like a never-ending stream of the stuff was filling me. He finally stopped thrusting and pulled his cock out quickly.

He stepped away, exhausted, as his sperm dripped from my pussy. It was splashing straight into my panties, making a milky pool in the gusset. I closed my eyes, utterly devastated by what I had done. I carefully pushed against the tree, forcing myself to stand upright. I leant down and carefully peeled my panties down my legs, stepping out of them. I took one look at him, before kneeling down and picking my ruined panties up between my thumb and forefinger.

I threw them towards him, as he instinctively held his hand out and caught them. I pulled my vest down and removed a leaf from my hair that I had noticed in my peripheral vision. “You disgust me,” I said, not looking him in the eye as I began to walk off.

As I created some distance from him I could hear him quietly respond, “Wait. Don’t you… do you want to get a drink or something?” Anger filled me as I turned and almost spat my response straight back at him. “Fuck off you creep,” I rather pathetically retorted as I turned and continued to walk away once again. As I walked back through the tree line I allowed myself to turn around one final time. He wasn’t looking at me any more, clearly realising that his still exposed penis was there for anyone unfortunate enough to see. He pulled him boxers and shorts up in one quick move, but not before tucking my cum-soaked panties into the front.

I quickened my pace, the park now noticeably busier with dog walkers and a few families walking around. My eyes stared at the floor, ashamed as myself and what I had done. My walk home continued in the same vein. As I stepped through the door of my apartment and towards the bathroom, I once again found myself staring into the body-length mirror. I felt sick as I looked at the mess of a woman in front of me.

A few hours later, cleaner and refreshed from some much needed sleep, I still felt sick. Sick, but the itch still remained.

[To be continued?]

---