The Lollipop

This is my entry for the Winter Holiday 2022 contest. If you're familiar with any of my stories, be forewarned that this is not quite the fare you'd normally get from me. It's short and raunchy. My attempt at a 'quick stroke'.

As a tradition for my stories, I like to provide a sort of 'OST'. The theme song for this story is Beethoven's Symphony No. 7 in A major op. 92 -- II (Allegretto).

This is a work of fiction. Any resemblance of the characters to actual persons, living or dead, is coincidental. All characters in this story are above the age of eighteen.

Not a creature was stirring, not even a mouse...

But not in this house. In this house, there was at least one creature stirring. I was stirring. I was all hot and bothered, curled up in my PJs with a fleece blanket wrapped around me while I lay on the couch in front of a crackling fire.

Sleeping on the couch on Christmas night, hoping to catch Santa Clause red-handed as he delivered presents, was a favorite pastime. Eighteen now, I long stopped believing in Santa Clause, but I still enjoyed the tradition. There was something magical about sleeping there, watching the snow come down outside the windows, and the gentle fire in the fireplace, the fragrance of the Christmas tree, and the Christmas lights changing color to color. Green, Red, Blue, Purple, Gold. The lights warmed the living room, just as flickering thoughts of a particular Chupa Chups lollipop warmed the cockles of my heart.

The lollipop in question sat in a bowl on a nightstand with other treats like candy canes and tootsie rolls alongside a plate of milk and cookies. A silly shrine to Santa Clause. A ritual my family had kept up for as long as I can remember because it was quaint and cute and because we're big on such traditions.

As for why the lollipop stood out to me, well, have you ever just had a random thought seed itself inexplicably in your mind, and have it grow into an obsession? That's what was happening with me now with the lollipop. Its spherical head, and its strawberry colored wrapping, glinting in the Christmas lights, caught me in a trance. It was probably strawberry flavored. But it's flavor was not what preoccupied me. Nothing as innocent and insignificant as that. I wouldn't be telling you this story if that was all it was.

No, the thought was dirtier than that. Much dirtier. The thought, which embarrassed me to no end, was how the lollipop might feel inside my pussy.

As for what seeded that thought in my head in the first place, I could only attribute it to the fact that though I was horny, I had been sexually repressed my whole life. You see, I grew up in a pretty religious family. I had grown up going to a Presbyterian Church (we were one of those 'every Sunday' kind of families). And my parents. One's Korean and the other's Japanese. So, picture conservative Christian values combined with whatever stereotypical notion you have of Asian parents (assume said stereotype is absolutely true in my case), and, well, need I say more? Sex before marriage was a sin. Hell, masturbation was a sin!

But like every good Christian, I'm not without sin. I'm not even remotely qualified to cast any stones. And I'm not entirely a spring chicken, either. In other words, I definitely masturbate. You see, I could never buy that masturbation could be a sinful act. It seemed such a natural thing to do. I could not be convinced that Eve herself had not masturbated (there couldn't have been that much else to do in the Garden of Eden). Yes, I masturbate, yet my creativity had not dared venture beyond the use of my fingers. Alas, using any other tool besides my fingers seemed to cross the line for me. That seemed too sinful. A cucumber was to me what an apple was not to Eve: A temptation that was a bridge too far.

That was until I started college.

Though my virginity technically survived the first semester, college was a sort of sexual awakening for me.

My roommate, after discovering that I had never used a sex toy, gifted me a vibrator, and -- holy crap -- what an incredibly clarifying thing that vibrator was. How nice it was to have a thing with girth penetrate and tingle your nether regions. No, 'nice' isn't an adequate description. It doesn't do the feeling justice. It was more a religious experience. My orgasms made me feel like what Buddha must have felt transcending into the Astral plane.

The vibrator had spoiled me. My own fingers were not enough anymore. But I couldn't bring myself to bring it home with me for winter break. I was too afraid of what might happen should my parents discover it. Mom was always nosing through my stuff. She'd find it eventually. And she'd probably drop dead from a heart attack once she figured out what it was. However, it was a decision I painfully regretted. Tonight, I was as horny as an eighteen-year-old, Christian, Japanese-Korean girl could get -- visions of sugar plums danced in my head, and I had no vibrator to help me settle my brain for a long winter's nap.

But there was that lollipop. Sitting dutifully and looking awfully delicious in that silly Shinto-esque shrine to Santa Clause.

Asian/Presbyterian shame welled up inside me. A shame that made me feel naughty. Yet I didn't try to tamp that feeling down. I liked the naughty feeling. It made my heart patter. It filled me with adrenaline. It made my pussy soaking wet. As quaint as it may seem to you, after my college sexual awakening, I became a junkie for shame, as much as a BASE jumper was a junkie for heights. I loved letting shameful thoughts swirl in my mind.

Like, what if I shoved that lollipop right into my tight little pussy? What if I used it to make myself come? Could it even make me come? And what if I get caught?

Imagining the consequences caused needles of fear to shoot through my body. My toes curled up. My butt clenched.

'No, you dirty whore. Stop thinking about it. Just go to sleep,' I uttered to myself. But as sage as advice as that was, I couldn't stop getting hotter. My clit swelled up. It became tight with sexual tension.

I slipped my hand into my pajama bottom to rub my clit. I had to. The touch was a nice relief. I shut my eyes to shut out everything else to focus on that touch. I licked my fingertip for slickness and put it back down there. I rubbed slowly. I breathed slowly. I felt satisfaction fill me up from the bottom up, rising inside me like bubbles in a freshly poured Coca Cola. But I also felt the temptation burn more brightly. The hotter I became, the more I wanted that lollipop.

I rubbed faster, trying my darndest to rub the dirty lollipop thought from my mind. I tried penetration. One finger, then two. But the more I fingered myself, the more I wanted that sugary little ball of hard strawberry candy on a stick inside me instead. I wanted to feel its bulging spherical shape stretch my tight little pussy.

I couldn't get myself to come. It would feel wasted if I did. Like I only had a set number of orgasms in my life, so I had to make them count. I wanted too bad for the lollipop to make me come.

I sat up. Frazzled. Full of lust. Full of fire. But also fear. I listened for the sound of any other creatures (aka my parents) stirring. I tuned my ears. I held my breath. Nothing but the sound of a silent night.

I gulped nervously. My throat was parched. It was tight.Ok, how about some milk? That'll take the edge off. That'll make me forget about the lollipop.

I slid off the couch. Crept over to the shrine and took a quenching sip of Santa's milk. The milk was good. It relieved the tightness in my throat. I sighed with relief, then set the half-full glass back on the table. But the relief of my throat's dryness didn't extend to the relief of my pussy's wetness.

Now that I stood at the shrine, within an arm's reach of the candy bowl, I couldn't help but stare wide-eyed at the lollipop, like Indiana Jones staring at an ancient golden relic in a death trap mausoleum. The lollipop's shiny red-green strawberry wrapping seemed to entice me to steal it, then strip it off.

I didn't go for the milk because I needed to quench my thirst. Who was I kidding? I wanted the milk because of its proximity to the lollipop.

Maybe if I just suck on it. It is a lollipop, after all. It was made for sucking. I'll just do that.

I took it with a trembling hand. Began to unwrap the candy. The wrapper crinkled loudly, spiking fear in me. My heart pounded like a drum.

I glanced up the dark stairway and spent a whole minute listening for any sign of movement from my parents. And when I didn't hear anything, I swiped the lollipop from Santa's sacred candy jar and plopped down cross-legged by the warming fire to unwrap it there.

Tenderly, I twisted the crinkling wrapper off the lollipop and popped it into my mouth.

A sweet strawberry treat.

I turned it in my mouth with my tongue, letting my saliva wet its sugary coat. Then I sucked on it and swallowed to let the sweetness travel down my throat.

It was a good piece of candy. But sucking on it didn't satisfy what I direly needed satisfying. So, again, I reached into my pajama bottom to touch myself. I placed my back against the warm wall beside the fireplace, spread my legs out in a bent V, curled a finger into my pussy, and rubbed the top of my softly tufted vulva and my throbbing clit with the palm of my hand as I sucked on that lollipop.

Oh, it felt so good, my fingers traveling inside me as sugary sweetness traveled down my throat. But the pleasure caused the heat to be so stifling. I began to sweat. So, I slipped off my pajama bottom.

That was better, but not quite as comfortable as I wanted it to be. My top was uncomfortable, too, not only because it was too hot, but because it also rubbed painfully against my hard and sensitive nipples. So, I took my pajama top off too.

The only thing I was left wearing was my pink cotton panties. At this point, you're probably wondering, aren't I deathly afraid of getting caught nearly naked like this? The answer to that is hell yes. I certainly was. Didn't I already say? I'm a junkie for shame. That fear of getting caught and getting in trouble made me even more excited. I guess it was because I was committing a taboo. That I was being transgressive, and I've forever fantasized about being transgressive. So why not now? Why not more? I slipped off my panties too, and left it strung limply to an ankle. Now I was really being transgressive. Naked in the living room, sucking on a lollipop.

Do you know what would enhance that fantasy of transgression?

Yep, you got it: pleasuring myself with a lollipop meant for Santa.

The urge to do so was like a tsunami barreling down on me. In other words, it was futile to run. The only thing I could do was stand there and drown in my urge.

I popped the lollipop out of my mouth. I studied it. My spit glistened on the pink sphere. Oozed down the white stick. Nicely lubricated, it glistened in the Yule log fire glow like a polished stone. I needed it inside me. But it would have to take a long way down there. No sense in rushing it.

I rolled the lollipop gently against my erect nipple and the skin of my pert breasts. The sugary spit on the lollipop stuck coolly to my skin. I did the same with my other nipple. Then, after my nipples were satisfyingly sticky, I put the lollipop back in my mouth and swirled my tongue around it to get it all lubed up again in preparation for the next thing I had in mind for it.

I lowered it down my body. Rolled it against my mons pubis, then rubbed it against my swollen, throbbing clit. My body tightened up. My legs sprang farther open. A moan came from my mouth, as soft as a church mouse's squeak. I glanced up the stairs worryingly. Still no movement. So, I kept going. I rubbed and twirled that lollipop against my hard little clit.

I drew the lollipop against my labia lips. I pushed it into my pussy slightly. Gasped as it submerged between my labia lips.

The burning log in the fireplace snapped and sputtered little tinder sparks into the chimney, startling me and causing me to retract the lollipop quickly as if I had put my hand on a hot iron. The fear of getting caught had me strung as tight as a piano wire. But it was a good fear. A rollercoaster fear.

Once more unto the breach, dear lollipop, once more.

I pushed it in again. Deeper this time. Into the abyss of my vagina.

The lollipop didn't quite have the girth of my precious vibrator. Still, my pussy was virgin tight, so pushing the lollipop inside me was a bit painful. Even as hot as I was and as wet as my pussy was. I drew out a long breath as I slowly pushed it in.

Braced my back against the wall.

I'm very sensitive to pain. So much so that whenever I had to get a shot, I would always try to keep my mind off the pain of the shot by pinching myself elsewhere as the needle went in. I did that now as I pushed the lollipop into my pussy -- I pinched a nipple hard as the lollipop penetrated my fragile cherry blossom.

Such a wonderful feeling. Like an electric shock. Like a polar plunge. The lollipop filled me nicely. Like it belonged up there.

My pussy grew accustomed to the candy quickly. I pumped it in and out, enjoying the sensation of the spherical shape moving inside me.

I twirled it around. I relaxed and tensed up my muscles to squeeze it, to feel its hard-shell press against the walls of my vagina. I wondered if I could crush it with my muscles. And if I crushed it, and all the crushed bits got stuck in me, what would happen then? Would I have to go to the emergency room?

The idea scared me but also excited me to no end. I imagined a hot doctor, who had volunteered for ER duty on Christmas night, stuffing his latex gloved finger inside me to dig out the broken lollipop pieces. The smooth latex of the glove. McDreamy's gentle finger exploring me to get every piece of sugary sweetness out of me. Mmmm...yum.

I was so hot now. I breathed hard and fast. My heart pattered rapidly. I was moaning a little too loudly. But I didn't care. I loved the pleasure, and I needed the world to hear that I loved the pleasure. So what if my parents heard me? What if they ran downstairs and saw me naked, masturbating with a strawberry flavored Chupa Chups, in other words, confronting the horrifying truth that one semester at college had indeed ruined their innocent, angelic daughter? That she had turned into a deviant little slut? The outrage! The shock! But as indignant and horrified as they would be, at least they would know the truth. They would know that I, like every young adult female on planet Earth, am a sexual being who enjoys sexual behavior. Just as God intended.

I pumped the lollipop in and out faster and faster. I rubbed my clit with my other hand, matching the rhythm.

I felt the pulsing orgasm come. My legs and abdomen tightened up. I gritted my teeth. I pumped faster, deeper. I gyrated my hips to get that little ball of strawberry sugar as deep inside me as possible. I trembled. I squealed. I exploded and felt the warm gushing of my sex rush over my hand.Oh God, I just squirted!

I looked down with widened eyes to find that my juices had gushed out of me and not only covered my hand but saturated the carpet in a neat dark circle.

My first reaction was horror, but then I relaxed, then laughed. I laughed joyfully at the tremendous intensity of the orgasm a simple lollipop had brought me, and I laughed at the sheer, crass ridiculousness of the fact that I had just masturbated with a lollipop.

The post-orgasm high took me. Gave me a warm buzz. Made my body quiver.

I became curious to know if I tasted like strawberries. So, I took a taste. I licked my sex off my finger, and you know what? A hint of strawberry. Next, I tried the lollipop. I popped it in my mouth and sucked. It wasn't a particularly pleasant taste. But I enjoyed it. My salty orgasm paired well with strawberry Chupa Chups.

When the bliss of orgasm finally faded, and after washing myself and tossing the lollipop away, I put my PJs back on, I went back to the couch, curled up inside the warm fleece blanket, and gazed into the fire as it burned slowly down into glowing embers. The Christmas tree lights continued to change their colors. Green, red, blue, purple, gold. Thoughts of my roommate randomly flickered into my head as I swirled into sleep. I thought of how grateful I was to her for teaching me about vibrators but curious to know if she had ever tried a lollipop.

Thank you, dear reader, for reading my story. I know it was a short one, but I hope it turned you on! If it did, you owe me a lollipop (or 5* and a nice comment 😛). If it didn't turn you on, let me know what I can do better next time! Enjoy the rest of your day!