Dare Me (new 7/29)

[neverdoubted]

Tiffany started stroking me, and in a flash, my cock was covered in green slime. Her frantic pace was familiar to my young, excitable body. And while her oral performance had been enjoyable, when it came to hand jobs, she clearly had lots more experience and ability. She was also much more enthusiastic about this activity because of her motivation to win the contest.

Meanwhile, my stupid brain forgot I was supposed to even be in a contest. I barely knew where or who I was! Her stroking technique was impeccable and pretty well matched what I usually did to myself. It took long strokes for her smaller hand to fully traverse my shaft. But she did it with gusto, knowing when to squeeze tighter and when to loosen her grip so it could slide over my bulging veins.

Feeling euphoric, I wanted nothing more than to melt into my mattress and let nature take its course. But then, much later than it should have, a panicked thought broke through my erotic haze and reminded me about the contest. I wasn't supposed to be enjoying this. I was supposed to stay strong and get Tiffany to have an orgasm first. If I did that, I would get to have sex with her as a reward. But that goal seemed impossible. Without permission, my hips started humping to meet every third stroke that Tiffany was making. Angry at the betrayal, I tried to make them stop, but my body was addicted to the extra stimulation and refused to cooperate.

My hand was still sitting uselessly upon her lower abdomen. Ordering it to get into the game, I pushed it down between her thighs and cradled her sex. I could feel how turned on she was. Natural lubricant coated her pussy lips, and her mound was radiating its heat. Convincing her body to make another diamond would be a trivial task. I just needed to enter her intimate folds and work her button. Unfortunately, rather than obey my instructions, my fingers, like my toes, would only twitch and curl in response to the unbelievable pleasure Tiffany was bringing me.

Thanks to her tongue bath, my arousal was already well off the charts. On a scale of one to ten, I had started somewhere around fifty. Alternating flashes of red and white filled my vision as my eyes stopped working and fluttered shut. I could barely make out the schlurping sound her enthusiastic hand made as it worked diligently to fully integrate Dave's lotion into my painful erection.

Gone was the relaxing, Zen river I had been counting on to carry me to victory. In its place was that dreaded cliff of arousal. Every stroke of her hand was like a shove in the back goading me over the edge.

Just a few more...strokes," I thought, "...and it will all be...NO!"

I couldn't give up this easily. Digging deep, I tried to picture myself slipping into that river of Zen. But the relaxing waters had become a raging torrent, threatening to dash me against the rocks or drown me if I didn't surrender my package to its imperative.

My aching balls constricted like they were wrapped in rubber bands. My cock thrummed with potency - the large, bulging tip turning red even as the green lotion got absorbed and its color began to fade. Tiffany was doing everything in her power to convince my primed fire hose to release its contents. If I didn't think of something quick, she would get her wish.

My cheeks burned at the thought of the head cheer captain watching me cum explosively and making a mess all over my own bedroom. The extremely humiliating image was enough to get my old cocoon to briefly reform and keep my orgasm at bay. But the protection began to crumble almost as quickly. The stimulating, dual onslaught of Tiffany's relentless hand and Dave's orgasmic lotion was just too powerful.

Running out of options, I forced my eyes to open and looked frantically around for something - anything - to distract me. Sitting beside me was a gorgeous, completely naked girl with a pleased smile on her face. She had the look of someone who knew she was about to win a very important contest. To best attend to my cock, her naked body was tilted toward me with her right arm outstretched. This position squeezed her already impressive cleavage into an even more tempting display. Her large breasts wobbled erotically with every vigorous stroke of my cock.

Her nipples were dark and stiff, a good reminder of her own extreme arousal. Her body was already on the verge of making another diamond. If I could just focus on her pleasure instead of my own for a second, I might still have a fighting chance. Trying not to think too much about how hot it was that my fingers were currently touching Tiffany Lennox's pussy, I made an effort to massage and stroke her folds. But my hand would not obey my commands. I could barely get my fingers to do anything except twitch uselessly.

Feeling the lava being squeezed out of my balls, I sensed I was out of time. My pot was boiling over. This was the end. I had lost.

...but then, the handle to my bedroom door jiggled, and a single, terrifying thought, gripped me.

You're a dead man.

An existential panic rushed in and disrupted my impending orgasm, but at what cost? Out of the frying pan, and into the fire. Absolutely convinced I was about to come face to face with Bruce the Moose, I jerked my hand out from between his girlfriend's naked thighs. But when the door swung open, another, much less intimidating figure appeared.

"Mikey, have you seen Ti- oh...OH!" said my sister, taking in the scene and quickly bringing herself up to speed.

She knew better than to barge into my bedroom without at least knocking. Opening my mouth, I calmly, but firmly, expressed my disapproval of Lucy invading my privacy. At least, that's what I meant to do. The only thing that actually came out was, "hnnnnngh!" as my extreme arousal twisted my face in undignified ways. Lucy giggled with delight to see what Tiffany was doing to me. This was exactly what she needed to complete her dare!

Seeing I was unable to form a coherent sentence, Tiffany spoke in my stead. "Did you need something, sis?" she asked, silently expecting my sister to reply. The lotion she had been applying was completely dry by now, and the sloshing sounds were gone. In their place was an even more lewd, thu-thu-thu of her bare hand jacking its way up and down my long, impossibly turgid shaft.

With her gaze never leaving Tiffany's busy hand, Lucy stuttered out her reason for intruding. "I-I was just, um...I didn't know w-where you went. And...what do you want for breakfast..."

"Oh, I'm not staying for breakfast," the naked teen replied, her hand continuing to milk the male partner sitting beside her, "but thank you for the offer. I'll be leaving in a few minutes," then, glancing down to check her progress, she clarified, "probably sooner than that."

Having my own sister look on in amazement while Tiffany jacked me to the brink of ecstasy made me want to die of embarrassment. Fortunately, my shyness about having an audience, along with the terrible fright I had just felt from thinking Bruce was about to kill me, gave my orgasmic defenses just enough material to muster one last stand.

In a moment of clarity, I had a thought. She was showing no sign that being caught completely naked in a boy's bed while giving him a hand job embarrassed her in the least. Surely that had to be an act, right? Well, there was one way I could put her to the test. If only I could get my stupid hand to work.

In my anger, I felt my hand ball into a fist…and saw my opening. I couldn't afford to waste this moment of manual control. Still feeling like I could burst at any second, I went on the offensive. Without warning, I reached over and plunged my hand back between her thighs. For the first time since the contest started, Tiffany was caught off guard. She gasped as my probing fingertip easily found its target - her prominent, and extremely sensitive clitoris.

Lucy's eyes went wide when she saw it. But I didn't have the luxury of explaining that I was currently engaged in a sexual duel of the highest stakes with her captain. And I wasn't about to try opening my mouth again to defend my actions.

When Tiffany shuddered, her hand's relentless stroking rhythm faltered, and my cock finally got a break from the continuous stimulation it had been receiving. As my blessed fingers continued following my instructions and adopted a vigorous stroking rhythm of their own, she grunted in surprise, and her own hips betrayed her. She couldn't prevent her overcharged body from bucking her needy pussy back against my massaging hand.

"Woah...uhh-," Lucy started to say something, but her mouth got stuck in an open, hanging position. A blush formed on her cheeks on behalf of her naked, bucking, big sister.

Tiffany recovered enough of her wits to resume stroking me, this time with abandon. "Get out," she ordered through gritted teeth - the very command I had been trying to utter earlier. I knew it! She did not want the indignity of someone watching her struggle to contain her own arousal at the hands of Mike Jenkins. By her decree, this race to the finish would be done in private. And what a race it was shaping up to be!

Each completely absorbed in bringing the other to their ultimate pleasure while surviving our own, neither of us could spare energy to exchange further pleasantries with my sister. I barely noticed when Lucy dismissed herself with another giddy giggle.

Of course she would be happy! Her big sister was literally in the act of completing her dare that very moment. She had achieved what originally seemed like an impossible task and had every reason to be overjoyed. She no longer had to worry about which teacher or student she would be required to flash at school tomorrow as punishment for failure. And, most importantly, she would finally be allowed to extract that big, healthy diamond her body had been growing since the start of her dare.

None of that crossed my mind at the moment, though. I was solely focused on the unfinished business I had with Tiffany. Over the course of this dare, I had enjoyed several new sexual experiences, first with Lucy's little sister, and now her big. But the ultimate prize was still in front of me. More accurately, it was within my grasp. I just had a little more work to do.

By focusing on her body instead of my own, against all odds, I was able to wade back into my river of Zen. It was no longer some lazy current, though. My body had been pushed far beyond its breaking point, and I had to make constant mental adjustments to find peace within the angry, roiling waters.

Luckily, Tiffany appeared to be struggling just as greatly. I started hearing the same, adorable noises she had made leading up to her first diamond. That was a very good sign. As we both grunted and groaned with need, I matched her stroke for stroke, driving her fertile body closer and closer to its peak even as she squirmed and struggled to resist.

Keeping up the pleasure pace required more exertion on her part. Her hand had much more territory to cover, and her trembling arm muscles were showing signs of fatigue. My strokes, while much smaller, were just as impactful. While my middle digit remained nestled inside her to keep pressing her pleasure button, the rest of my hand got acquainted with the rest of her sex. My palm patted a happy beat against her perfect mound like the world’s sexiest little drum. And my other fingers made sure to stroke her pretty, pussy petals every chance they got. A sloshing sound soon accompanied my every stroke as her moisture factory was conscripted into the battle.

When I felt her grip flag and her pace slow, I smiled to myself. The tide was turning! Feeling her squirm and buck adorably, I quickened my pace. Opening her eyes wide and forming her mouth into a tight, O shape, she puffed out short, halting breaths as if she could release some of the heat from the roaring fires of arousal I was stoking within her overwhelmed body. I sympathized with her but gave her no reprieve. I would not stop until the gigantic jewel forming deep inside her was released and I got to claim my prize.

She blubbered and moaned, but nothing was slowing the approaching freight train of her arousal. Issuing a loud grunt of needy frustration, she looked down in disbelief at my still impossibly full erection. My self-control was proving to be just as hard and firm as that iron rod between my legs. I think the reality was starting to dawn on her. If she didn't think of something fast, I would soon be plunging my rod deep inside her.

Thinking my victory was at hand, I dared a little grin. What else could she do now? Well, it turns out there was one thing she hadn't tried yet. Out of options, she resorted to doing what cheerleaders do best. She started to cheer.

" Mmmm-Hmmm…...Mmmmiiiikeeeey," she groaned - her sexy whimper morphing into my nickname. Then, a few seconds later, "Mmiiikeeeey...can't be...beat."

Those first few words, foreign to me and out of context, made no sense. But then, with more conviction and a clearer voice, she repeated the full chant.

"Mmmikey, Mikey can't be beat. Come on, Mikey, turn up the heat!"

When I realized that Tiffany had just personalized one of our school's cheers, my whole face turned red. Briefly, I forgot what I was doing, and my hand halted its massage. Seeing that she had struck a nerve, Tiffany seized the opening and quickly improvised another cheer.

"We know Mikey fights 'til the end. He's done it before, he'll do it again. Yaaaay, MIKEY!"

I'm not sure you understand how sexy it is to have your own, personal, naked cheerleader stroke your ego and your cock at the same time. I tried to return to my river of peace, but the eager cheerleader plunged right in after me and dragged me back to shore, kicking and screaming.

Because talking during our contest wasn't explicitly forbidden, she wasn't breaking any rules. She was still only touching me with one hand as agreed. But leaning in so close to me that her plump lips were nearly grazing my right ear made tuning her out impossible.

She had an endless catalog built up over a lifetime of cheering and rolled deftly from one verse to the next. Incorporating my name into them was a trivial matter. And all the while, she moved her hand up and down my cock in perfect time with the beat of her chants.

It's like she was whispering her cheerful encouragements directly into my brain using the sexiest and perkiest voice she could conjure. And when she randomly worked in the phrase, "big guy", I lost control. Happily issuing her latest cheer, she sang into my ear, "Come on, big guy. Do it! Do it! Come on, big guy. Do it! Do it! Come on, big-"

That's when I exploded. I started to cry out to announce my ecstasy, but the roar caught in my chest when my lungs seized. The first spurt of my cannon fired across the room in a high arc – a white liquid, the color of surrender and defeat - followed quickly by another and another. Tiffany cried out in a different kind of relief and immediately let go of me. Having won the contest, she wasn't inclined to stick around any longer than necessary.

Pain shot through my penis from losing the pressure of her grip while in the middle of its ecstasy. I was forced to grab it with my own hand and finish pumping myself dry, even though it was degrading to do so in front of a girl. Watching spurt after spurt fly across the room and all over my carpet, I knew what a mess I was making. But I couldn't do anything about that now. My trigger had been found, and my balls would not stop until they were completely empty.

Standing up and sweeping up her clothes off the floor, the naked cheerleader took one last look at me.

"Well, Mike Jenkins," she said, reflectively, "I have to admit, you do live up to the hype. It's too bad I already have a boyfriend. If things had been a little different, I think we could have had a lot of fun together."

She was gone before I had even finished cumming.

[TeenFan]

A lot of guys have a reputation of "Eat n Run"
Tiffany could be called a "Cum n Go" girl.

[Freesub]

Damn that's sad, I was hoping Mikey would finally get what he wanted.

[student]

Does this mean the end of this story line? Will Mikey ever recover?
Will Tiffany have to get herself off--now?

Thanks for an exciting story.

[neverdoubted]

Fatigue caught up to me quickly. And while part of me had been satisfied, another part was left wanting more. When I forced myself to get out of bed and put on some clothes, my arms and legs complained, as if my body had lost all its motivation. But the mess I had made wasn't going to clean itself.

The intoxicating scent of feminine arousal lingered in the air. Its presence reminded me of my poor showing and how close I had come to heaven. My cock shrank somewhat, but I could still feel the dangerous chemicals coursing through my system. I had a jitteriness that I knew I would be dealing with for the rest of the day.

When, through my still open window, I heard Tiffany's Mercedes convertible start up in the driveway, I kicked myself all over again. How could I forget she had driven herself to our house? I had never been at risk of Bruce charging into my bedroom and catching us in the act. It had all been an irrational fear conjured up by my overprotective imagination.

In time, I would come to remember the events of that morning - that entire weekend - much more fondly. But right then, crawling around my bedroom floor with a spray bottle of cleaner dabbing at my carpet with an old towel, I just felt...spent.

At one point, Lucy came back into my room. Her dare was complete and, always honoring the rules, she was coming to ask me if I wanted to watch her reap the first reward. I declined, barely bothering to look up from my labor. After what I had just gone through, I just wasn't in the mood. I snapped at her to leave me alone, and she walked away with her shoulders down.

Though a cold front was forecasted, the summer sun was intent to hang on one more day. And without A/C, our house grew stiflingly hot. I could feel our free day off school slipping away and could just tell I was going to be cranky and irritable the rest of the day. Eventually, with no destination in mind, I went for a drive. More than anything, I just wanted to get out and take advantage of the conditioned air.

As I drove on, the world's problems crept in, and a heaviness settled over me. Mom’s hours kept getting reduced and we were basically out of money. The meager scraps I had started setting aside for a new air conditioner weren't even close to covering the cost. If I didn't think of some way over the fall and winter to earn more, we were really going to be suffering when the weather turned warm again in the spring.
It’s not that I was opposed to getting a job myself. I just didn’t feel qualified to do anything. I liked to read and organize lists. But that didn’t sound like a real job.

Counting the months, I identified another reason for my melancholy. It was late October, time for Lucy's birthday. The unseasonable heat would yield very soon. And unless I was wrong, the cold weather would trigger her condition to go into its annual hibernation.

In the winter, she didn't ask for dares. She was content to keep to herself and didn't really need me that much. Apparently, she didn't need to make diamonds during that time either. As far as I knew, her PWCS wouldn't let her make them any other way. If I were in her shoes, I would never be able to survive that long without. But maybe girls were wired different someway.

When my low fuel light came on, I had to turn the car around. I was wasting gas and didn't have any money to buy more. I made up my mind to apologize to Lucy for being so curt earlier. But entering our sweatbox house, I saw no sign of her.

She had been so wound up before I left that she was almost certainly in her bedroom taking care of business. I bet she was making some spectacular jewels at that very moment! It was going to take several before she was satiated. But sulking and feeling sorry for myself, I had squandered my opportunity to observe.

It was just a fun little tradition at the end of every dare. But now that I was facing a long winter of no performances, I started to regret turning her away earlier. If I had known the lost years were coming and that this diamond would be the last I would see her make for a very, very long time, I definitely would have stopped what I was doing and taken in the show. Now it was too late and too awkward.

I tried to watch tv, but eventually got overheated and went to take a cold shower. In the process, I felt a stirring in my loins and had to answer the call of Dave's chemicals. They were ready for another round. Unfortunately, though I gave it my best effort, I struggled to replicate the orgasmic success that Tiffany had achieved. My body was back to fighting me and had even more stout defenses now which it did not hesitate to bring to bear.

What I really needed was a naked cheerleader taking over the stroking duties and whispering sexy encouragements in my ear. An eager young redhead peppering me with adorable little kisses while preparing to impale herself on my pole would also have done the trick. Unfortunately, I had neither of those things. Somehow, I had ended up back where I started - a pathetic virgin fruitlessly stroking himself in the shower with an erection that won't go away. That was the cruelest twist of all.

Giving up and exiting the shower still hard, I returned to my room and got dressed. Unwilling to spend another minute stuck inside our stifling house, I headed outside. I figured a visit to the library might distract me and help me calm down. If anything, it would be cooler.

I couldn't afford to drive there, but I did have another, less expensive form of transportation - pedal power. Locating my old bike in a dusty corner of the garage, I dragged it outside into the light. Both tires needed air - no surprise given I stopped riding it when Mr. Beski's family gave us his car. But after making a few laps around the yard, I declared it road-worthy and took off down the street. The thought of burying myself in knowledge and leaving the real world behind for a little while sounded pretty nice. It even managed to bring a smile to my face.

The End

[student]

That was a wild ride!

I'm guessing it will be September before we see The Lost Years. It will take time to top Big Sister, Little Sister, and make The Lost Years better.

Thank you for an entertaining tale. If I get antsy for more, I can start over with Dare Me's first chapter.

[Freesub]

Now that the arc has concluded, if I may suggest, have you considered possibly posting an arc of Dare Me about the perspectives of other characters during moments we already saw happen.

Such as Tiffany 's thoughts during this chapter, or maybe the history teacher during the presentation, or Mr Beski's grandson during Lucy's naked fitting.

[perseus]

I've been so far behind on my reading, trying to catch up.

I'm really hoping that there is an update to this wonderful story soon! I miss Lucy!

[neverdoubted]

As the contents show, there are still three chapters remaining. I may post them at a later date if reader interest picks up. But as long as it isn't receiving enough votes, I will continue giving higher priority to other stories. Right now, the prospect of finishing Dare me is not looking good.

[Freesub]

As the contents show, there are still three chapters remaining. I may post them at a later date if reader interest picks up. But as long as it isn't receiving enough votes, I will continue giving higher priority to other stories. Right now, the prospect of finishing Dare me is not looking good.

Honestly there's an element of not wanting it to end. I myself didn't vote for it even though I love it because I don't want it to end