Halloween Night Pegging

As soon as I arrived at the party she caught my eye. Maybe the witch costume that she was wearing imbued her with some extra magical allure. Or maybe it was just that it came with a very short skirt and fishnet stockings, which showed off a great pair of shapely legs. Either way, my attention was instantly attracted and, noticing that she was alone and not talking to anyone, I was drawn to go speak to her.

I wasn't the kind of guy who was usually comfortable or confident approaching single women at parties, but tonight was Halloween and that meant that all bets were off and normal rules didn't apply. You could flip things back to front and become somebody different from normal for this one night only. Tonight, for example, I was Zorro. Or at least I was dressed like him. I was all in black, with boots and a cape, a plastic sword at my belt and half my face covered in a black mask and wide brimmed black hat. I had the costume and I was going to adopt a swagger to match. And besides, even if I did strike out and humiliate myself with a woman that I'd never met before, at least I still had the anonymity of the mask to hide behind.

She was standing by the punch bowl, still alone as I approached. Her costume consisted of a black and purple minidress covered in black lace, with a corset-style top, laced with purple ribbon, and a wide but very short skirt, pushed out by a lacy black petticoat. She was more curvy than skinny, but that just made her costume flatter her best parts even more. The corseted dress pushed her ample bosom up and the short skirt and fishnet stockings showed off her curvy thighs. Tucked under a pointed witch's hat her dark hair had a dyed purple streak. Whether this was just for tonight, I didn't know. Like me she had covered the top half of her face, although in her case with a lacy domino mask.

"Are you brewing up a potion?" I asked.

"Yes. At midnight it turns everyone into pumpkins," she quipped drily in reply.

"Well, that doesn't give me much time to work my own magic on you, then, does it?"

"That's OK, after the witching hour it's no longer Halloween, and I turn back to a regular girl," she said with a hint of a smile, "So your time to make it with a witch is limited anyway."

"You mean I've got a shot at making it with a witch?"

"A little more of this potion and I'm down for anything," she did a half giggle, half hiccup, which was actually oddly cute and took a big gulp of the luminous-colored Halloween punch.

"So, am I allowed to ask your name?" I asked, "Or do names give you power over a witch?"

"I don't know, Zorro. Not really one to criticize keeping your true identity secret, aren't you? Just call me Samantha."

"Like in Bewitched?"

"Well, yes, but also like my actual name!"

"So, Samantha, did you ride here on your broomstick?"

"Did you know that real witches' broomsticks were actually dildos?" she said, significantly upping the flirting ante from light teasing, "Not trying to come on too sexual all of a sudden. Just a fun fact I like to share."

"Please share," I said, "And, really, if you can't be abruptly weirdly sexual from behind a Halloween mask, then when can you?"

She laughed.

"It's true," she went on, "Real historic witches couldn't fly of course, but they could feel like they were with hallucinogenic flying ointments. Stuff like belladonna, mandrake and henbane."

"Aren't those poisonous?"

"If there's enough of it, they are. But they were also an ingredient in a lot of healing potions and, like I said, could get you pretty high. In fact, that's why we call it 'getting high' because that's how it felt being on a trip like this. It felt like flying. And how do you think they got all those trippy herbs in their body?"

"Drank it?" I said, sipping on the punch.

She gave her head a suggestive shake and pointed down between her legs.

"It's a flying ointment, remember. You'd rub it on your skin," she said, "It'd work best somewhere the membranes were thin and the ointment was easily absorbed into your body. Somewhere that would make the trip extra pleasurable."

"Witches put potions on their dildos?" I finally understood where this was going.

"That's what some people think," she smirked, touching the black cat necklace she also wore, "And, well, witches did love their pussies, didn't they?"

I didn't know whether the dildo broomstick thing was true. I'm not even sure if Samantha herself did (assuming that even was her real name). But it was just the kind of quirky, out there, provocative conversation starter that I wished I could sometimes throw out. I was immediately engaged in wanting to get to know her better.

And, as the evening passed, I did. Sort of. I mean, I learnt very little about who Samantha was, beyond a curvy woman who looked great in a witch costume and had a store of sexy witch facts to back it up. Nothing about her life, job, relationships, anything like that. But I did learn that she was smart, cute and quirky, that she had a devilish dirty laugh and that I was definitely becoming more and more attracted to her as the punch flowed and the party went on.

"I don't want to take up all your time," I said, noticing a couple of hours had passed and we had just been talking one-on-one that whole time, "Maybe it's witchful thinking, but is there a bit of a spark here?"

"I'll forgive the terrible pun, because I've always had a thing for a masked swashbuckler," she said, indicating my Zorro costume.

"Perhaps you'd like to see what I can do with my sword," I said cheekily, "Maybe you'll find it can do things that your wand can't."

"I don't know," Samantha smirked, "I've got a pretty powerful wand. And that's a magic feeling that lasts beyond the witching hour!"

"Perhaps you'd like a demonstration," I said, drawing my plastic rapier and waving it in the air like the cavalier swordsman I imagined myself to be for one night only.

Unfortunately, I couldn't be said to have the co-ordination of a legendary swashbuckler at the best of times, and even less so after drinks of highly suspect punch. My slashing action ended up knocking the drink right out of Samantha's hand, spilling the undetermined bright green contents down my pants and across the floor.

"Oh, God, I'm so sorry," I said, fumblingly, going from wannabe suave to awkward and clumsy in moments, "Let me clean that up."

I was down my knees with a handful of paper towels, mopping up, and she joined me, kneeling next to me and helping me clean the spill. Her hands brushed over mine and I lifted my gaze to catch her eyes behind her black lace domino mask. I was about to speak, but instead she leaned in and kissed me on the lips, just for a moment, before pulling back. I could see her blush a little behind the mask but there was still a smile on her face.

"I've always liked a suave swashbuckler, yes," she said, "But a little clumsiness is cute too! I think you might need a bit of cleaning up yourself."

I looked down to where the bright liquid of the punch was undoubtedly staining my pants. I didn't want to call it a night and end my connection with the sexy witch, but she was right that I couldn't really stick around like this.

"You know, my place is just around the corner," Samantha said, "You could come back and I'm sure we'd find some way to entertain ourselves while your pants go through the wash."

Samantha's apartment was small and irregularly cluttered, although the effect was ultimately more cosy with a hint of chaos than a total mess. There were a few hints at her witchy side dotted around, although not ones that would seem particularly witchy were it not for her costume: an abundance of autumnal scented candles, a black cat - more chunky than sleek - curled up asleep on the couch. Overall, it felt homey.

The pleasant feel of Samantha's apartment stood in stark contrast to the uncomfortable cold, sticky pants that still carried the wet stain of Halloween punch.

"Get those off," Samantha said, aware of my obvious discomfort, "And let's go somewhere more comfortable. It's a lot warmer in the bedroom."

I stripped from my pants and Samantha threw them into the washing machine in a little laundry cupboard. Instinctively, I also removed my black Zorro cape and sword belt.

"Nice view," said Samantha from behind me.

I glanced over my shoulder to see her checking out my ass. It felt flattering, to be honest, to have a virtual stranger look at my body like that. I hadn't felt admired like that in a long time. When I felt her hand slap against my butt and fondle the cheek, it made me a little giddy with excitement.

Having removed my cape and belt, I reached to take off my black Zorro hat and mask. But Samantha's hand caught mine before I could remove the mask.

"No," she said, "Leave it on. Just for tonight, be who you want to be."

Keeping her own lacy domino mask on, she took me by the hand and led me to the bedroom. Behind my mask, I did feel more fearless than I would have done without it. I could entirely sense what she meant in those few short words. Halloween was a time to become someone else, someone bolder, braver than your normal self. Hell, my normal self would never have had the courage to talk to a cute, curvy girl all alone at a party, let alone find myself led up to her bedroom that very night. I wondered if that sensual lace mask granted Samantha the same kind of confidence, or maybe she was just ordinarily the kind of woman who would take a guy home the night they met. I realized that I really knew very little about the woman behind the mask, but right now that not knowing just made things more exciting.

In the bedroom, we hardly shared another word before we were locked in a longer, more lingering kiss than before, our costumed bodies pressed up against each other, my cock beginning to stir and stiffen in my underpants. I ran my hands across her body, down the purple ribbons of her corset dress, over the tops of the fishnet stockings covering her thick thighs, feeling her warm body conform to my touch.

I felt her teeth bite gently against my bottom lip as I reached beneath her skirt and slid my hand between her thighs. She let out a slight gasp as my fingers brushed over her panties. Sliding a finger inside the gusset, I could feel she was already wet.

Eagerly, I dropped to my knees and pushed her to a sitting position on her bed. Her panties were black lace, a match for the mask around her eyes. I slid them down her legs and cast them aside. Pushing her thighs open, I positioned myself between them. Her wet cunt looked delicious beneath curls of black pubic hair. I ran my tongue along the inside of her thighs and around her labia, enjoying the thrill of her body tensing and relaxing at the touch of my mouth.

She pushed her crotch up against my face and I hungrily responded, lapping at her pink lips, before flicking my tongue around the hard nub of her aroused clit. Samantha moaned with pleasure as I circled that special spot with my tongue, making her writhe and squirm, her thighs pushed against the sides of my head. I could tell that she would climax pretty soon if I kept this up.

Instead she pushed me back off her and stood up.

"Your turn," she grinned, a lopsided smile that looked extra mischievous with her witch hat and black lace mask, "Zorro was a legendary swordsman. Let's see what sort of weapon you've got and what you can do with it."

I was already semi-hard from going down on the sexy, thick-thighed witch, not to mention the whole heady experience of the evening so far. As Samantha stripped me of my underwear, my cock sprang to attention. Her smile got wider and she looked approvingly at my hardness. Just as I had done with her, Samantha pushed me into a position seated on the bed and got down on her knees. I had an incredible view of the cleavage created by her witch dress' tight corset top. She looked up into my eyes as she took my cock in her hands and began to stroke it even harder, licking her dark painted lips seductively.

Samantha licked her tongue up my shaft, making it quiver at the warm wet touch, then swirled it around the glistening head of my hard cock. As she opened her mouth to swallow my erection, her left hand stroked my hard shaft, while the right began playing with my balls.

Still sucking on my cock, the cute, curvy, masked witch began to move her right hand from cupping my balls to stroking the tender skin beneath them. Soon she was rubbing against my perineum as she went down on me. It felt good, enhancing the pleasure she was already giving me. But Samantha's magic finger didn't stop there. Caressing along the line from my balls up between my legs, her fingers soon began to explore inside my crack. My entire body twitched and stiffened as Samantha's index finger brushed across my tight, puckered hole, but she soon made me relax, gently rubbing all around the entrance to my ass. It felt good - really good - being fingered back there. It was something that I had never experienced before, but now I knew more clearly than anything that I wanted that finger to explore further.

"Do you like that?" those dark lips smiled as she took them from my cock, her finger now knocking at the door, pressing right against my hole.

"Yes," I sighed in agreement, "Feels good."

"Do you want more?"

"Go on," I agreed, giving the beautiful busty Halloween witch the go ahead to work her magic.

Samantha grinned even more excitedly than before. She took her hand from between my legs, just long enough to give her index finger a sensual lick before putting it back again. Now a little wet, Samantha's finger pushed back against my hole, rubbing up, down and around until I opened up a little and let the wet digit slip just a little inside me. I gave an involuntary sigh and, in her other hand, my hard cock grew just that little bit harder.

"See what magic a witch's spellcasting finger can do?" she said with a giggle.

I had no idea how experienced she was at this kind of fingering - maybe she was as new to it as I was - but I could feel she had a magic touch. My body felt alive in new ways even with her finger only just inside me. Only up to the first knuckle of her finger was in my ass, but I felt penetrated and vulnerable like never before. And extraordinarily aroused as she began to run that finger around in little circles, making a sort of beckoning motion as if inviting me to open up even further. I obliged, spreading my legs wider, lifting my ass to meet her fingers.

"How about some helpful enchanted ointment?" Samantha winked beneath her black lace mask.

"Huh?" I asked, confused.

"Lube," she said, shaking her head, "It's the magic ingredient that makes everything go smoother. You're going want it if you want more than a fingertip."

"OK," I said, feeling nervous anticipation mixed with an eagerness to see where this would lead, "I guess I should have known from our first conversation that an enchanted ointment would have some part to play in the rest of the evening."

Samantha stood up and walked around the bed. I felt a twinge of disappointment at losing her finger from inside me, along with a lot of strange feelings of being exposed and awkward in a stranger's bedroom; fully dressed in a Halloween costume on my top half, naked and baring my ass on the bottom. Mostly, though, I was just enjoying the sight of her walking around the room, still in her corseted black and purple dress, fishnet stockings and boots, although now with the short, ruffled skirt doing little to hide her lack of panties. Those big breasts, thick thighs, and wide hips were just the sort of body that had been entrancing men since the days of real witches, while the thigh high stockings and purple streak in her hair were just for the modern guy. Every bit of her made me want her, though, a little bit more with each moment.

She opened a drawer in her bedside nightstand, taking out a shiny squeezable tube of lube. I couldn't help turning to peer into what else this mysterious witch kept there. I was not at all surprised to see that the witch kept a wand, only this one was less for turning people into frogs than for turning herself into a quivering mess. There were other toys in Samantha's drawer of fun too, and something that I couldn't entirely identify, which was made of harnesses and buckles.

"What's that?" I said, instinctively.

A big smile came over her face as she pulled the whole thing out. The straps and harnesses were like a belt with loops between them. Dangling from it was the black rod of a dildo. It dawned on me that what I was looking at was a strapon.

"Oh, this?" she smirked, "That's just my broomstick. Care for a ride?"

For the first time since I caught her eye from behind a mask at the party, I was speechless. I didn't know what to make of this. Was that a genuine offer? And, if it was, was it one that I was willing, even eager, to accept? I tried to process the thought. Just a moment earlier I was accustoming myself to the new sensation of my asshole being penetrated by a single finger, now I was being pushed to imagine something much larger back there. I had to admit to a little curiosity.

I couldn't deny that being penetrated was a pleasurable feeling I had not thought much about before today, but pleasurable it clearly was. That finger had felt good. I knew I wanted it back inside me. And deeper. There was no question of that. The more I silently eyed up the dildo in the masked witch's hand the more I couldn't help imagining her pushing it up inside me too. And, after all, when would be a better time to try something new and strange than Halloween? Samantha was practically a stranger and, thanks to the masks and costumes that we both wore, we would be unlikely to recognise each other out in the real world. So, even if I was feeling a little nervous about how taking a shafting in the butt might make me look and feel, I knew that this might never be known or mentioned again.

"Are you asking for real?" I said with a nervous laugh.

"That depends," she grinned, eyes sparkling behind her black lace mask, "Do you want it for real?"

"I do," I admitted, "But go easy on me. It's my first time being so enchanted."

She smirked and I could see that I had made the right choice, at least in terms of pleasing my bewitching Halloween one night stand. I couldn't know whether she had deliberately given me a curious sight of her favourite toy as a trick, but it was entirely clear that getting to wear it was definitely a treat. Might it be a treat for me too?

Samantha seemed as giddy as a witch having taken her flying ointment as she slid the strapon harness up her legs, the black dildo flopping around all over the place as she adjusted the straps to fit. Her excitement was infectious and made me feel increasingly keen to experience this with her. Not that I wasn't still nervous, but seeing how keen Samantha was to switch up the traditional bedroom roles definitely helped with those nerves.

"Now, where were we?" she smiled, walking back around the bed, the black dildo swinging between her legs, tube of lube in her hand.

Throughout all of this, I had remained lying on the bed with my feet on the floor, naked from the waist down but still in my shirt and mask. Samantha moved back to her former position kneeling by the bed and pushed my thighs open once more. My cock had softened while she had been taking out the strapon and putting it on, but my body still felt alive with excited energy such that the gentlest touch of the witch's hand on my thigh made that softness quiver and stiffen once more.

Looking me in the eye, she squeezed the lube onto the fingers of her right hand. In a moment, those fingers were between my thighs, rubbing across my perineum and up against my tight hole once more. Now slick with her witch's ointment, the finger that had previously been knocking on my door was given easy access. Before I really knew it, that finger was right up inside me, penetrating me in places I'd never imagined I could experience pleasure before.

I couldn't help but squirm and moan as Samantha pushed me back further onto the bed, lifting my legs in the air to further expose my bare naked ass. With her left hand she rubbed more lube into my crack and pulled it open to allow both of her first two fingers to slide inside me, spreading me wider, opening me up. God, it felt good. My cock, soft just moments earlier, was stiff as a board while my body felt light as a feather.

With two fingers stuck inside my ass, Samantha started to work her magic, sliding out and then deeper in, circulating and bending those fingers as if beckoning me toward her. All I could do in response was to push my ass toward her, rubbing against her hand, reaching for her to penetrate me deeper and deeper.

"I want it," I gasped, hardly able to get the words out.

"Want what?" Samantha replied, still fingering my receptive asshole.

"Your thing... The strapon..." I was struggling to get the words out with the intense pleasure of Samantha's third lubed up finger joining the first two inside me and her other hand gently grasping the shaft of my cock, "I want you to fuck me..."

"Time to ride the broomstick, you mean," she giggled, taking her fingers from my hole and getting to her feet, lubing up the shaft of her strapon.

She looked more incredible than she had all evening, standing there still in her mask and witch's hat, curves perfectly enhanced by her purple corset dress, her thick thighs looking so strong and powerful. And there, between them, sticking out from the lace skirt of her dress, the black rod of her "broomstick", held in her hand, slick with lube and ready to impale me.

My bare legs were in the air, my open asshole pointing directly at Samantha's slick black dildo. She placed one hand on my raised thigh, the other on the dildo and positioned the head of it against my hole. Even with the lube and my ass being loosened by her magic fingers, the thick black rod was a lot to take. It pressed against my asshole, trying to get up inside me.

"Just relax into it," Samantha said, stroking her hand over my thigh, "Don't fight against it."

I opened my thighs further, tried to relax and bit my trembling lip as I felt the full thickness of the witch's strapon slide between my cheeks and up inside me. Once the first part had entered me, it became easier to take it. Before I knew it, she had buried a couple of inches in my ass and it was feeling pretty nice and full back there.

"How's that for you?" she asked as she pushed deeper up into me, stimulating places deep inside me in ways beyond the physical.

"Like I'm flying high," was all I could reply as Samantha's so-called broomstick slid up my ass almost as far as it could go.

If I had been under a real magic spell, I could not have been more totally in the thrall of a powerful woman than I was beneath this curvy enchantress as she thrust deep into my ass. She took her hand from its position guiding her strapon into my ass and moved it so both hands were pushing against my legs, with my ankles now up over my shoulders. In this dominant position, her hips thrust forward and pushed her strapon into me, sliding in and out of my cheeks, stimulating every single nerve back there.

Before long, Samantha was really pumping in and out of my ass. She may have begun gently, letting me get accustomed to the feel of taking something bigger than her finger back there. But, now I was used to the feel of it, she didn't hold back. My body rocked to the feel of her plowing into me and the sensation was incredible. All I could do was lie back and take pleasure in giving my whole body up to this beautiful stranger in the black mask.

Even in the tight black and purple corset dress, her large breasts heaved and shook as she thrust deep in and out of my willing ass. My cock, absolutely rock hard from the feeling of taking something just as big inside me, also quivered and flopped around as the curvy witch rocked my body.

Samantha reached between my legs and grasped my hardness in her hand even while she continued pushing up inside me, impaling me as she stroked me. I was already so incredibly aroused by the stimulation her strapon was providing to the magic spot deep in my ass that it didn't take much of the touch of her hand to push me to climax.

I don't know whether it was the novelty of my body being stimulated in places deep within, aroused like never before, or if it was some strange magic of the masked witch, but this orgasm was like none I had ever had before. It spread from that spot deep within my ass like a crashing wave, every fibre of my body feeling electric with pleasure. And then my cock was ejaculating streams of hot cum as my ass twitched and clenched around Samantha's hard black strapon.

"Wow," she said with a giggle, with a stream of my cum landing on her chest as she bent over my submissive body, "Looks like your wand has cast a spell of its own."

It was a cheesy line, but it diffused any discomfort that might have been there in the room after this new, experimental sex act. I was learning that this kind of silly, slightly awkward humour was a big part of Samantha's personality and I was starting to find it very charming indeed. Not that I wouldn't be charmed by any woman who could make my ass feel this good.

I began to sit up, but Samantha pushed me back onto my back on the bed. She pulled her strapon from my well pleasured behind and slipped out of the harness, dropping it to the floor. In a moment, she was kneeling on the bed, her powerful thighs in their fishnet stockings straddling my face. I looked up and could see her beautiful wet cunt, surrounded by curls of dark pubic hair and the lace of her short skirt.

"Come on, it's your turn," she said, "Time to work your own magic."

From her strong position straddling my face, she pushed her cunt down toward my mouth. It was so wet with arousal that it was clear that she had enjoyed pegging my tight hole as much as I had enjoyed being on the receiving end. My tongue ran around her labia and brushed her clit, making her squirm and moan loudly in a way that drove me on. Eagerly, I lapped at Samantha's cunt like an enchanted victim drinking from a witch's cauldron, sucking and tonguing, feeling her warm, aroused body writhe above me, hearing her breaths coming quicker and shorter. And then, just as I had as she screwed my ass, Samantha hit her climax and rode it into my face, pushing her crotch right against me as she screamed out loud before collapsing on top of me.

A little later, we lay side by side on the bed, both basking in the pleasure of the incredible experience we had shared together as virtual strangers, still half dressed in our Halloween costumes.

"Well, that wasn't how I expected the night to go," I laughed, "But, then, you never get what you expect when dealing with a witch."

She reached up and removed her black lace mask and finally, for the first time, I looked at her face.

"This is me, by the way," she said, "The real Sam. I told you: after the witching hour I turn back into a regular girl."

It was an appealing, bright, rounded face with a wide smile and hazel eyes. Not beautiful, strange or mysterious, but coming to charming life when she spoke or smiled. It was, I decided, a face I could certainly get used to looking at. The witch had enchanted me, given me an incredible night to remember, but perhaps now I could get to know the real girl.