CreatorsOk
Jay Friday
Jay Friday

patreon


The Challenge

At midnight on All Hallows Eve, seek ye a powerful place;

Pure, of unsullied strength, outside of time and space.

There, the Aspirant meets his challenge, to battle before they wake;

For power is never given; to get it, one must take.

The one challenged chooses the battleground, weapons, terms;

The Aspirant must win, if power they wish to earn.

The defeated suffers the loss of all life's hard toils;

For to the victor...

Go the spoils.

---

The book's leather cover and binding had been nondescript; title and author obliterated long ago by time and humidity by the time it arrived in the rare books shop I had been working in as a young man, nearly three decades ago. There were massive sections of it that were unreadable or missing entirely. But the book had been what started me down the path.

Only nine lines on yellowed paper. But something about it had the ring of truth, had sparked my curiosity. Made me want to learn more.

And so I did. There were scattered references in other obscure texts that corroborated it. That on All Hallow's Eve, every year, there was some kind of...cosmic opportunity for power.

Power was what I had always wanted, you see. I didn't always acknowledge that to myself -- sometimes I dressed it up in more altruistic motivations -- but now, as the moment I had been preparing for my entire life was arriving, I acknowledged it was true. I wanted power.

And I believed I could get it.

First, you had to be in the right place. And you had to win the power from...the one challenged. In some kind of conflict they would pick.

Finding the place had been tricky enough. Power had so many different definitions. I had tried a number of places over the years, thinking they might fit this line as the place of power. Most of them had been difficult to get into at midnight on Halloween. Seats of global government. The Wall Street trading floor. Boardrooms of the biggest companies, homes of the most influential celebrities...

Of course, it turned out to be simultaneously much more complicated than that, and much simpler. Power wasn't really in buildings, it was in people. Minds were powerful. I needed to make my own mind a place of power.

And the place had to be unsullied, the manuscript indicated. Pure.

Virginal.

Fortunately, I had realized that before I got...too far in life, if you take my meaning.

So now -- 28 years later -- I lay down in my own bed, at home. It was 11:57. Time to get ready.

I ran through a few meditation exercises, focusing myself and getting ready to drift off to sleep. It had taken years of training to achieve what I judged to be the right headspace. To find the place of power.

Of course, meditation and mental focus wasn't the only thing I had been training.

Once I could access the place of power, I needed to win...a challenge, of some kind. Against...well, someone else. The lines weren't very clear on that point except that the one challenged would get to pick the terms.

As such, I had done all kinds of training. I was proficient in dozens of weapons and martial arts. I was excellent at chess, go, and a few other very popular games. I was strong, fast. I was articulate, good at oral debate and reasoning. I trained everything I could think of, body and mind.

I was, in short, at the height of my personal powers. I felt ready for anything, felt like I'd have good odds across a range of contests. I could wait longer, train more, but I was in my forties now, and while I might develop further skills, I knew my physical abilities would wane over time, my reflexes would slow.

It would only be tradeoffs from this point forward. This was the peak of my abilities. This was the moment.

11:59. I watched the clock tick away the few, final seconds to midnight, and closed my eyes.

The mental training paid off; I found my center in no time.

I snapped my eyes open. I was still lying down on my bed. The clock read 12:00. Everything was the same. Had it worked?

"Well, hello there."

I turned to face the other direction, startled.

A woman was lying next to me, in my bed, although as I twisted to look at her, she sat up, looking around. "Nice place."

The woman had Asian features; long, straight black hair, brown eyes, high cheekbones, full lips. Certainly pretty, though her features were a little too angular to be truly beautiful. She was wearing a black t-shirt and jeans. Up one arm, a patchwork of tattoos ran.

While I was assessing her, she looked around the room with curiosity. Then she looked back at me. "Congratulations. It's been a good few years since there has been a challenge; achieving the right mental state is difficult." She spoke with a slight accent, although my mind couldn't quite place it.

She stood up from the bed and went to look at a framed photograph on my wall -- me and Kasparov, playing chess. Sometimes the masters of a particular discipline weren't the best teachers. Kasparov had been a notable exception, an excellent tutor.

In the photo, I was two moves away from mate, although that wouldn't be obvious to most people.

She turned and looked at me, her nose wrinkled. "Very complicated board position. I guess I won't challenge you to a chess match, then. Did you beat him?"

This was the...one challenged, from the manuscript? She seemed...just like a person. The moment of confrontation that I had been anticipating was falling a little flat. I had pictured my willpower pitted against bodiless dark forces, maybe some kind of...mental battle of wits...or, I don't know, a one-on-one gladiatorial duel against some horror, in front of an arena full of cheering demons.

Instead, as far as I could tell, it was just me and this woman, in my bedroom.

I sat up, sitting on the edge of my bed. "I, uh..."

She kept walking around the room, inspecting objects. She glanced at the pistol I kept on my bedside table. "No shooting competition either, I guess. Although real firearms experts know about gun safety. That should be in a gun safe or something," she said, disapprovingly.

"I live alone, nobody else is ever up here. And I didn't realize you'd be in...my bedroom," I muttered, a little defensively. I felt off-balance.

"Well, I get to pick the battleground and the weapons. And I find that I can tell a lot about a person from their own home..." she paused, trailing off as she pulled a book off my bookshelf, turning it over in her hands. On Formally Undecidable Propositions of Principia Mathematica and Related Systems by Gödel.

"...Ugh, so we're not doing math or logic, then. I never liked Gödel anyway. Head too far up his own ass for his own good," she said, distastefully.

I opened my mouth and hesitated, realizing now that the stakes in her inspection of my bedroom were rather high. She got to decide the terms, and everything she looked at told her something about what I was good at...and what I wasn't. She was learning about me, looking for advantages. Well, two could play at that game. "So...you've...done this before?"

"I have defeated eighty nine challengers," she said, promptly. She gestured at the tattoo up her arm -- a swirl of multicolored flower petals, I now realized, looking at it more closely. She pulled the t-shirt up slightly to reveal her abdomen, which was tattooed as well -- the petals must continue up her arm across her shoulder, onto her chest, and then continue down onto her stomach. No doubt if she were naked, and I counted the petals, there would be eighty nine of them.

If she were naked. She had a great body, I couldn't help but think, as she lowered her shirt and resumed looking around the room. The stomach she had just shown off was tanned, smooth and flat, a trim waist.

She was watching me look at her body, I realized. I met her gaze. Brown eyes looked back at me. They were quite captivating. They had a kind of a...light, behind them. Or maybe it was just her expression. Whatever it was, her eyes conveyed excitement, amusement. Possibility.

Then she turned, and resumed inspecting the room. The jeans she was wearing clung to a round ass. Not notably overweight, but not especially athletic either -- just nice, soft curves.

While I was looking at her ass, she was looking at my fencing saber hung on the wall alongside a few other weapons. "Wow. You know how to use all these, huh? You really thought of a bunch of stuff." She said it almost approvingly.

"I, uh, just tried to be prepared," I muttered. I still felt on the back foot here. "Eighty nine? You must have, uh, been around a while..." That was a lot of people who had lost to her. I was feeling a little intimidated.

She turned back and looked at me. "Yep. Challengers used to come along more frequently; but even learning about the challenge is harder to do these days. Lately, it's been down to one every twenty or thirty years or so." She eyed me up and down, appraisingly. "You must be resourceful, to have even learned of it."

I met her gaze again. I felt...uncomfortable. I couldn't place her age, I realized. She had the beginnings of crow's feet, but other than that, there were no clues. She could've been in her early thirties...or maybe her mid forties? Heck, maybe mid fifties, if she had aged really well...or late twenties...

The power. Maybe she didn't age. Maybe I wouldn't age, if I won.

Her lips curved up into a grin, the light in her eyes dancing, now. It occurred to me, my reaction was probably predictable to her, if she really had won eighty nine challenges. Discomfiting as her ageless features were, I had to admit, it was nice to finally talk to someone who recognized how hard it had been to get here. I nodded. "It was a lot of work."

"How did you even find out about the challenge, anyway?" There was an admiring note in her voice.

It was nice to be admired, I thought. "An old book."

"Mmm. How interesting," she mused. "Hey, wow, you've been to the North Pole?" she was looking at another photo.

I didn't respond, not wanting to give her any information she might use to her advantage. I sat silently as she walked around the room, inspecting various things, remarking upon them.

Eventually, I grew impatient. "C'mon, don't you have to pick a battleground and weapons? How much time are you allowed to take?"

She shrugged. "I'm not sure time is even really passing right now, per se. Every time I've won a challenge it's still midnight on All Hallow's Eve afterwards."

She continued her unhurried perusal. I watched her move around the room. I didn't want to say anything else -- I was worried my bedroom was giving away far too much as it was. Instead, I just enjoyed the shape of her ass in those jeans as she stood on tiptoes to pull a book off the top of my bookshelf, bent over to open a desk drawer, and otherwise moved about.

Eventually, she sat down on the edge of my bed next to me with a sigh, and said, "Well, I have to admit, I'm impressed. Most Aspirants have spent far less time preparing."

That made me feel smug...but it might be a ploy from her to make me overconfident, so I tried to stay focused. "So, what do you want the battleground to be?"

She shrugged. "There are a few areas of obvious oversight where you're inadequately prepared, but that's true of everyone.

I blinked. Obvious oversight? Inadequate!? "W-what do you--"

She cut me off. "Relax, relax. Everyone has some weaknesses. Even me. But for you, one stands out as the most likely, so I'm gonna go with that."

I opened my mouth to speak, but she just kept going.

"I recognize you, Aspirant, facing me on All Hallow's Eve, here in the place of power," she said, formally. 

The light in her eyes was cold, now. Imperious.

The cadence of her speech had changed too, and the sound was suddenly...different, like maybe the walls of my bedroom were much further away from us than I knew them to me. Like we were in some vast, hollow, echoing space, not sitting on my bed.

"For the battleground of this challenge, I choose sex. Whoever is brought to orgasm first is defeated. The only weapons are our bodies."

She looked at me, standing still across the bedroom from me, hands folded neatly in front of her. "The challenge commences. Begin when you are ready." Her voice had returned to normal.

Well fuck. I blinked, gathering my thoughts.

This was an obvious oversight on my part. Potentially a fatal one. Of course the challenge could be about sex. It could be about anything. It was hard to find much information about the challenge, but one of the earliest texts referenced the Aspirant winning a calligraphy competition.

Unfortunately, I hadn't trained for this at all. Quite the opposite, in fact.

And in retrospect, this was obvious. She seemed to know the rules. She would know I had to be a virgin to even be here. And she would be talented. Otherwise why would she have picked sex? Maybe my meditative practices would help me last longer...

Fuck, I thought, ruefully. I knew there were various tantric sex practices, ways of making women orgasm quickly, of delaying your own climax. But I only knew of them. Not how to do them.

"You're stalling," she whispered. There was an amused smile on those full lips.

My face heated. "You took plenty of time selecting the terms," I snapped.

She shrugged, unbothered. "True. Take all the time you like."

"Have you beaten many Aspirants with sex?" The words came out more resentfully than I intended. This was my own fault. Resentment was a waste of energy; I needed to calm down, focus, and look for advantages.

She nodded, amiably. "Many, yes. Not all, though." In a smooth motion, she pulled off her shirt.

She was wearing a practical black bra, not especially sexy -- but her cleavage caught my eye anyway. I tried not to stare. Her breasts weren't enormous, but they were full on her lean frame, pushed together in the bra into appealingly tan cleavage.

My attention was diverted, though, by her tattoo.

The multicolor petals swept up her arm, across her shoulder, and then swirled down between her breasts, before skirting to one of her hip bones and then continuing down into her jeans. The overall effect was, well...hot. I couldn't help but stare. The flat stomach, the tattoo, the dark eyes watching me look at her...

I met her gaze, trying to tamp down my arousal. "I-I wouldn't have thought sex was always the best choice," I muttered, trying to think of options, a way out of this situation.

"It isn't. It's different each time. Trickier with women, especially...but most Aspirants are men. And men get so focused on the idea of losing a physical combat of some kind, they tend to forget about...other types of challenges," she noted, her eyes still on mine, that light dancing in them once more. "To be honest, even the fact that you've covered your bases with things like chess and math is really quite unusual. Bravo."

She paused, and then her lips curved back up into that knowing smile. This time it almost had some mockery in it. "You do seem more prepared than most...except for this." She gestured at her own body. "You have tried at least a few things with women, surely? I know the line says pure, unsullied strength, but that author really took liberties translating from the original...strange that inaccurate translation has persisted all these years when there were more accurate options available, isn't it?"

I blinked. Shit. The implication was clear: I hadn't needed to abstain. No doubt she was responsible for the poor translation. It was undeniably clever -- if you were ageless, why not make sure the most common translation was one that gave you a clear weakness to exploit?

Her mouth formed an O of delight. "Oh dear...you're a virgin, aren't you?"

I didn't answer, which was answer enough for her. She giggled. It was low, throaty, and rich. She moved towards me.

It was nothing like when she had been walking around the room. The way her body moved as she walked towards me was so...sultry, now. There was some deliberate sway in her hips, an arch to her back that thrust her tits forward. I was captivated. I tried to stall some more, to distract myself, slow her down.

"W...what do the different colors mean? Of the petals?" I practically blurted the words out, the first thing that came to mind.

"Oh, my...have you been inspecting my body?" She grinned as I blushed. "A very perceptive question. Each petal is a challenge won; the color shows what the challenge involved. Red means the challenge involved sex... the other colors mean other things." She waved a hand dismissively.

Shit. There were a lot of red petals in the tattoo. It was by far the most common color. I tried not to dwell on the implications of that, wracking my brain for other things that would help.

She sat next to me on the edge of the bed. I tried not to look down at her breasts.

"Look," she said, seriously. "No offense, but I'm going to win. The same way I wouldn't beat you at, I don't know, fencing, or chess..." she gestured at the weaponry and photos on the wall. "...With no practice, you don't stand a chance at beating me at this. So with that in mind, let me make an offer, since you've never done this before. Is there...something specific you'd like me to do?"

I blinked, uncomprehending. "Uh, what do you mean?"

She smiled gently, now. "For your first time, I mean. You're going to cum before I do. You have no chance. But I can at least make it fun for you. Do you want a blowjob? I'm quite good at them. Should I ride you? Or maybe you'd like to fuck me from behind?"

"I, uh..." When I was younger, such things had been at the forefront of my mind; but over the many years of celibate focus on my goal of winning the challenge, I had learned to temper my arousal, to focus my energies elsewhere. And I tried to do that now, to ignore her confidence...but images all came rushing to the forefront of my mind, with her sitting next to me. How she'd look working my cock with her mouth, or panting as I fucked her from behind...she'd be talented, she'd beaten so many before me...

I was getting hard, I realized. Not good.

I tried to put it out of my mind, to search for some advantage. I nodded, slowly, as if accepting what she said. "I see your point. I'm beaten."

Then I put on a false, eager smile. "I...I've always found it hot to think about..." I trailed off, hoping I wasn't hamming it up too much.

"Yes?" Her lips parted, the light in her eyes danced.

"Well...what if you used a toy on yourself while we had sex? A vibrator?" I had heard women orgasmed more easily from toys.

She laughed, delighted. "Wow. You have some fight in you. Very clever. No, I'm afraid. The only weapons are our bodies. No dildos, no vibrators, nothing like that."

Damn. I didn't know what to do, but I knew the best thing was to outwardly slump in defeat, discouragement.

I didn't have to pretend that much. I racked my brain, but couldn't come up with anything else as clever. I decided to opt for direct.

"Well...since I'm going to lose anyway, will you at least tell me what you like?" I said, hesitantly. I didn't have to pretend the note of despair that crept into my voice either.

She searched my face, momentarily, looking for some stratagem hidden in the question.

But after a moment, she simply said, "Sure. But it won't help you."

"What I like," she whispered, low and urgent, "is when a man loses control. Not right when they cum; the moment just before their orgasm, when they cross the point of no return and realize it's inevitable. When I can see on their face that they know I've won, that in spite of their efforts to resist, their efforts at control, the pleasure will overwhelm them. Watching them succumbing to the blissful defeat, the dawning realization on their face that they can't hold back any longer, well..."

She gave an involuntary shiver. "It's so hot. That's why I've been doing this so long, I think. I don't just like to win. I get off on it."

Listening to her describe it -- the soft whisper, the urgent arousal in her voice -- I believed she was being honest. You could tell it really turned her on...and as a result, my mouth was dry and my cock was rock hard by the time she stopped talking.

Fuck. Not good.

She glanced down at the outline of my cock in my boxers, and I could see a small smile flicker cross her face. I blushed -- I didn't know what I had expected, but it hadn't involved her just showing up in my bedroom. I felt vulnerable.

Her gaze lingered on the bulge of my cock. "Otherwise, I get off to the kinds of things most women like during intercourse. A good ten or fifteen minutes of deep, rhythmic thrusting. Eye contact. Passionate kissing. Girth during penetration. Clitoral stimulation. That sort of thing." She shrugged, as if it didn't matter.

But it was more than enough to make me blush, embarrassed. I had so little experience here...Ten or fifteen minutes?

I didn't like my odds.

"But I think that's plenty of preliminaries," she whispered. "We should get to the main event. After all..."

She leaned over, into me. I felt the soft curve of one breast against my side...and then one of her hands slid up my thigh, grazing over my hard cock before resting on my length.

"...you're already so excited." The light was back, dancing in her eyes.

I moaned, helplessly. Her touch was feather-light, perfect. Thoughts of strategy began to dissolve at the sensation of her hand, the feeling of her body against mine, the growing arousal.

I forced myself to focus through the haze of pleasure. The stakes of losing weren't exactly clear, and the translation was already imperfect -- but it sounded like death was certainly on the table, and at a minimum, I'd have wasted years of hard work.

Fortunately, all that work had given me self-discipline in spades. I tried to think about what might...shift the balance of power, here. Give me some kind of opportunity to turn the tables.

Nothing came to mind, admittedly. But I had to say something.

"You like the way my cock feels?" I tried to inject some dominance into the question.

She giggled. "Mmm...is that what you want to hear? How hard this big dick feels in my little hand?"

Her hand slipped inside my boxers. I felt her wrap it around my shaft and give me a pump.

"Should I tell you how excited it makes me to think about your thick cock in my little pussy? Is that what you want?" She whispered the words, staring into my eyes, searching my face.

Fuck, her hand felt good, and it was hot, hearing her say those things. But my attention was fixed on her face. I got the sense that she was...well, assessing me. I had played poker at a high level; it was one of those game, like go and chess, that gave you skills that transferred well to other games. And right now, she reminded me of a professional poker player looking for tells just before they called a bluff.

I didn't know what she saw, but she must have seen something, some reaction from me that I wasn't aware of. Her expression turned thoughtful. "No..." she whispered. "Some men like their ego stroked. But that's not what you want, not really. Not a man like you. Your life has been one of discipline. Accomplishment. You'd want something else, not nice lies...something you probably don't even know you want..."

I blinked. She was right -- I had led a life of discipline, accomplishment. There was no way I would even be here, otherwise. But I didn't see how that was relevant, didn't understand what she was getting at.

It was hard to think about what she was saying anyway, the way she was slowly stroking me. Her hand was soft, her strokes even. My cock had been leaking, I realized -- now her hand was slick around me.

But she was continuing. "...You desire power."

I blinked again. Well, she had that right, and it was an obvious enough conclusion, given the challenge.

"...And disciplined, accomplished men always want the truth." Her lips curved up into another smile. "Well, then. I shall be truthful. And I shall be powerful. You'll want me. Desire me."

I tried to gather my wits about me. I knew what those words meant, but I didn't really understand what she was getting at. And the slow handjob she was delivering was exquisite, distracting.

So she spoke again before I had anything to say.

"And the truth is," her voice was flat, this time, honest, "even if you had more experience...your cock is a bit small for me."

I reddened, embarrassed. I didn't know what to say to that. My life had not featured attractive women pumping my cock while they told me it was small. The juxtaposition between the humiliation and the pleasure left me confused, uncertain.

"I mean, I've been doing this a long time...it takes a special man to get me off," she teased. "And you don't have what it takes..."

"I-I-could..." I stammered the words out.

"You could what?" She continued slowly pumping my cock; I could feel myself leaking all over her hand. "You could fuck me until I cum all over this little cock?" she leaned in, her voice a mocking whisper in my ear, "I don't think so. But you're welcome to try, if you like."

She pulled away from me. I watched -- a little dazed -- as she stripped off her jeans, revealing black panties that matched her bra. She lay back on the bed.

I stood up over her, uncertainly. I didn't know what to do. I needed to make her orgasm. I tried to take a moment to gather my wits, to think.

"No need to rush, I know you're a virgin..." she giggled as she said the word. "If you're already about to cum and you need to take a minute, you can."

I was off balance, yes, perhaps humiliated, intimidated, but I didn't feel close to cumming. "N-no, I can..." Reflexively, I moved forward, positioned myself between her legs at the edge of the bed.

"Ooh, such a stud..." The sarcasm in her voice was obvious.

I knew I was playing into her hands, but I had to make her stop. Shut her up for a minute, so I could think clearly. I acted on reflex; hand-to-hand combat training had been a clear area of focus for me, obviously. Wrestling, judo, jiu jitsu. It gave me all the tools I needed. I stepped forward and reached across her body, a pull on one leg, leverage at her hip with the other hand...in one satisfying, well-executed movement, I had her on her knees on the bed, bent over in front of me.

She didn't even gasp. Just twisted to look back over her shoulder at me, a sly smile on her face. "Mmm, too bad it's not that kind of wrestling match, isn't it? Instead--"

I wasn't going to let her finish, say something else that was humiliating and riled me up further. I dropped my boxers to the ground, pulled her panties to the side, and slid into her.

And then I froze, and so did she.

For her part, she shut up, as I had hoped she would. But that was it, no sound, no reaction...she was still, watching my face, that same amused light dancing behind her eyes.

For my part, I let out a moan. Fuck. She felt incredible. Wet, tight around me, but yielding. The soft curve of her ass under my hands, the way her skin felt...the sensation in the moment, my first time inside a woman, was overwhelming. I felt the urge of a rising orgasm in me, but was able to control it.

And then my eyes met hers. "Mmm, c'mon baby, put it all the way in," she purred.

I was all the way in. I felt my face redden again.

I knew it was probably just something she was saying to fuck with me. But she delivered it just casually enough that it might be the truth. Maybe she just couldn't tell. I tried to push away the embarassment. "I, uh..."

As I spoke, as if realizing it, she smirked, and said, "Oh, sorry." But she didn't sound sorry. She just adjusted herself slightly, rocking against my hips, moving on my length. The way she moved was practiced, confident. Unlike me, she had done this before. Many, many times, if her tattoo was any indication.

"I guess you're not technically a virgin anymore, are you?" she murmured. "Congratulations. So what're you going to do now?"

I tried to ignore the comment, tune her out for a moment. I felt like my arousal was under control. But I took a moment to adjust to the sensations, to breathe a little more regularly. To give myself the best chance I could. And to try to think of some way to turn the tables on her.

She broke the silence. "You know, you've got a nice body," she commented. She reached a hand up and back, running it across my abs. "You're cute. This would probably be a lot of fun, except that..." she rocked her hips again, and I bit back another moan, as she worked my cock in and out of her. "...you're cute all over."

It completely derailed my train of thought. Now, in addition to being embarrassed, turned on...I was angry. I knew that was probably exactly what she intended -- to keep me from thinking clearly about this -- and it certainly worked. "Fuck you. You're being a bitch."

"So do something about it." she taunted. She stretched out, lengthening her torso and bending her back so her breasts were against the mattress. "If you can."

The smooth feel of her thighs against mine, the way that the curve of her ass flared out from her waist...well, I didn't need her taunting me as any added incentive.

I grabbed her by the ass with both hands and started fucking her. I was as rough as I could be, fucking her hard and fast -- I wanted to shut her up.

It felt incredible. The way she gripped my length, slick and tight, the sensation of sliding in and out of her, the slap of my hips against her ass...god, this was hot.

I gave her thirty or forty seconds of the roughest pounding I could deliver. "You like that?" I was breathing hard, now. I grunted the words out, and slapped her ass for emphasis.

"It's...pleasant." She was moving with me, meeting my thrusts. Her breathing was even. If her voice carried any emotion, it was boredom. "Can you...go a bit deeper?"

I felt another flare of anger, but admittedly, it was accompanied this time by a sense of...futility.

I was incredibly turned on. She was hot, experienced; the way she was moving her body felt amazing against mine. Every thrust was getting me closer and closer to a massive orgasm. To be honest, I was surprised I had lasted this long. I knew I wasn't going to last much longer.

And nothing I did seemed to be getting her any closer to orgasming.

She glanced back at me again, her eyes dancing with amusement, as if she knew exactly what I was thinking.

"Maybe you'd get deeper in a different position." The words came out in a purr.

I needed the reprieve anyway. Reluctantly, I pulled out of her. I was breathing hard.

She rolled over, leaning back on her elbows on my bed, looking up at me.

"Are you enjoying your first time?" She had a wry smile on her face. "Come lie next to me for a minute." She patted the bed next to her.

I lay down next to her uncertainly, turning toward her to look her in the eyes. I needed a different plan if I was going to have any hope of winning this.

She met my gaze. "I'm having fun playing with you," she whispered, seductively. "Watching you try to use that inexperienced little cock," she glanced down as she spoke, looking at my erection, "...trying desperately to get me off...well, I'm enjoying it immensely. It's so cute how frustrated and turned on you're getting."

I flushed again, but this time it was with...a sense of helplessness. I didn't say anything. She was right.

She bit her lip, looking at me. As she did, her hand slid up to caress one of her breasts, and then to unhook her bra and pull it away. Tan skin and brown nipples came into view. I stared, watching her tweak one of her nipples as she continued to talk.

"I knew you'd like the truth best. I could be nice. Tell you how big your dick is. How good it feels stretching me out. Pretend to orgasm. But those would all be lies. And I like it better this way. And I think you do, too." The glimmer behind her eyes was darker, now. Almost menacing.

"N-no, you're...this is...I don't..." I didn't even know what I was going to say. You're being mean? I don't like it? It sounded pathetic even in my own head.

"No?" She said the word as a question, asked innocently. In a smooth movement, she was straddling me, on top of me.

I knew probably thirty ways to reverse this position in a heartbeat, and another thirty ways to choke her unconscious, break a limb, or otherwise incapacitate her. But in that moment -- with the head of my hard cock at her wet entrance, feeling the heat coming off her pussy, her dark eyes looking down at me -- none of that came to mind. I stared, entranced, at her naked body, the way that tattooed petals wrapped up her arm, snaked down between her breasts, across her torso, down the inside of one thigh...

"If you don't like this, though," she said, as if puzzled, "...why is that little cock so hard for me?"

And then she sank down onto it, sliding my cock inside her easily. I moaned, helplessly.

"Like I said, you fucking me from behind was...pleasant." She leaned over me, whispering, her lips just barely grazing my ear as she spoke. "But let me show you what it's like when someone who knows what they're doing takes charge."

She started moving, and I closed my eyes, overcome by the sensation. She was rolling her hips and bouncing on me at the same time, her rhythm perfect. The strokes were slow, unhurried, an almost lazy sensuality in them.

After only a few seconds, I could tell that this would make me cum, quickly and easily. There was no way I could keep control of myself.

I opened my mouth to tell her to stop, to slow down -- and became aware that I was already making a sound. A low whimper, that turned into a needy moan each time she slid down my length.

"W-wait..." I couldn't help the pleading note in my voice. I was looking up at her. I could feel the orgasm rising, rising...

Her eyes were amused, confident, but there was hunger there, too. "Wait? But I have been. I've been holding back this whole time. I could have done this right away. When you first rolled to look at me, I knew you...well, weren't up to this kind of challenge. That I could get you off easily. But I've been...kind. Patient. Let you have your fun."

Her movements became...not faster, exactly...but more urgent, somehow. Some change in how she was moving communicated a woman in the throes of passion, a woman about to crest over the edge -- though the poised amusement on her face indicated nothing of the sort.

I had no idea what to do, no idea how to slow down, stop what was happening...but my body didn't want to stop, anyway. I was about to cum.

"S-stop..." the word came out of me as a panicked whisper as I fought to keep the floodgates closed.

She pulled off of me. "Oh...are you sure?" The light in her eyes was cruel, now, as she smiled down at me.

I whimpered, again; there was a desperation to it this time. The absence of motion was intolerable. I had to cum. Had been about to cum.

"...Because I think what you really want is for me to make that little, inexperienced, virgin dick cum. Am I right?" Her lips were parted.

There was a disciplined part of me that didn't want that. But that part of me wasn't in control anymore. I needed her to start riding me again.

Feeling ashamed, knowing I was making a mockery of decades of my hard work, but too aroused to care, I gave a frantic nod.

"Well, say it, then." She looked excited, now, for the first time, and lowered her hips a little. I felt the head of my cock part her folds again, a promise that the pleasure could be mine once more. If I did what she wanted.

"Please...please make me cum," I said. My cock was throbbing uncontrollably.

She just raised one eyebrow. "You can do better than that."

I knew what she meant, what she wanted me to say. I didn't even feel ashamed anymore -- there wasn't room for anything else besides desperate arousal, the need to get off.

 "Please...make my...inexperienced...small...virgin...dick...cum," I moaned the words out. 

"If that's what you want," she said, her voice knowing.

And she sank back down on me.

It was over seconds later. She resumed her motions, a hungry sensuality in the movements now. And she was staring me in the eyes, lips still parted, as I felt myself about to cross the point of no return.

Her eyes lit up, practically glowing. "Fuck...yes..." She moaned the words out.

I let out a long, low, moan myself, and, staring into her eyes, I started cumming. The orgasm was a tidal wave cresting over me -- impossibly powerful, all-consuming. I knew I'd lose myself in it, but there was no way to stop that, now.

I felt my cock throb as I began to spray inside her.

"Give it to me," I heard her hiss. "Give me all of it."

And I did. I gave her everything. I didn't have a choice.

To the victor, go the spoils.


More Models and Creators