Dare Me (new 7/29)

[Freesub]

This is getting amazing! Maybe Tiffany will be willing to let Mikey do it with her just because of the size of his dick?

[rrh62]

This is getting amazing! Maybe Tiffany will be willing to let Mikey do it with her just because of the size of his dick?

Well, yes. That would make total sense, although, from the text, he did not appear to make as much of an impression on Tiffany as I was expecting him to. Any other girl would probably jump his bones by the end of the massage. However a BJ seems to me like a cheap reward for his effort IMHO.

[WingDing]

Perhaps she’ll find her boyfriend less satisfying and surreptitiously come back for seconds. Or at least a second massage.

[Kazu]

That might be difficult. Despite them being in the same club, it might seem odd to have the older Tiffany frequenting the younger(bottom of the caste) Lucy without having everyone at the school talking, especially with Tiffany's standing withing the groups.

[rrh62]

That might be difficult. Despite them being in the same club, it might seem odd to have the older Tiffany frequenting the younger(bottom of the caste) Lucy without having everyone at the school talking, especially with Tiffany's standing withing the groups.

Yup. You can't rattle your social standing, no matter what. Though I'm still hoping that @neverdoubted will still have some surprises for us in store.

[neverdoubted]

Nope, sorry. Just ran out of surprises.

[Kazu]

No more surprises?

[neverdoubted]

"You're a dead man."

I swallowed as the unease settled over me. From the neck down, I was completely on board with what was about to happen. But even as Tiffany placed an impossibly soft hand on each of my legs and gently spread them apart, the phrase still ringing in my ears caused some primitive preservation instinct to kick into overdrive. I could just picture Bruce the Moose charging into my bedroom and catching me in the act with his girlfriend. He could twist me into a pretzel and toss me out the window without breaking a sweat.

As she leaned closer to my throbbing organ, it wagged vigorously up and down with excitement. But even as my body welcomed the impending pleasure, my mind diverged from the task at hand and went in its own direction. It became preoccupied with answering a single question; simple, but potentially critical to my survival. Where was Bruce Meyer?

I wracked my brain trying to remember what all Tiffany had said about him during her stay. Of particular interest were their plans for the day. Hadn't she said something about needing to buy a new dress? Yes! They were planning to drive to Westfield to do some shopping together. It was unusual for a junior to bring a freshman to the homecoming dance. But Tiffany Lennox was no mere freshman.

Does he know she was spending the night at our house last night - a house that just so happened to contain a younger, teenage boy and no parental supervision? Is he driving over here this very minute to pick her up like Hanna's family had done for her yesterday? Is that the sound of a car engine I hear!

Just then, as a wave of terror crashed over me, my mind and my body diverged even further from each other, and my consciousness retreated into the cocoon of nothingness it had built to keep me safe. Even the most extreme external stimuli, from a sense of impending doom to the heights of orgasmic pleasure, could not easily pierce such a sturdy, protective shell. And I just so happened to be experiencing both of those strong feelings at the exact same time!

Even as I felt a soft breath between my legs and looked down to see Tiffany's mouth moving closer and closer to its target, a single, bizarre thought formed in my head and bounced aimlessly around the empty space my conscious mind had recently vacated. It was, "whose cock is that?"

I watched as the gorgeous, half-naked cheerleader parted her perfectly formed lips and stretched out her pink tongue to lightly contact a spot near the base of the penis sticking up between my legs. My senses could acutely feel and were excitedly transmitting the signals of what was happening to my body. But my brain insisted on intercepting all external stimuli and keeping them separated from my fragile consciousness.

She gently dragged the tip of her tongue up my rod, leaving a small trail of saliva behind. When she got to my tip, she puckered her lips and had to strain her neck to reach the bulging mushroom hovering high in the air to give it a playful kiss. Then, holding herself in place, she tilted her face upward to look me in the eye. As long as I live, I'll never forget the image of Tiffany Lennox kissing my cock - her big, brown pools looking up at me expecting to see the pleasure she was giving reflected in my face.

Finding my expression blank, her smiling eyes morphed into a quizzical look, then one of concentration. Cheerleaders tend to share certain wirings. In addition to being exceptionally competitive, they also take pride in what they produce. Tiffany did not seem pleased that her initial efforts were only producing muted reactions.

Now, I don't know how extensive her blowjob experience was to that point in her life. But judging from the way she hadn't shied away from my intimidating member, it was safe to assume this was not her first time.

Ending her introductory penis kiss, she lowered her mouth back to the base of my ridged, bumpy anatomy. With a renewed zeal, she opened her mouth wide and pressed her tongue more forcefully against me. Determined to make a more memorable impression this time, she zealously dragged the widest part of her tongue over my bulging member. Reaching the top, she did not stop, but immediately lowered herself for another lick of my fleshy lollipop.

Seeming to take my gratification as a personal challenge, she made repeated trips, sometimes tilting her head slightly to the left or right, but always leaving a wide stripe of saliva in her wake. Licking all over my erection, she got to taste every inch of my potent flesh and sample the various bumps and bulges that made it unique.

Her slathering effort was unbelievably effective. Pleasure centers all over my body began lighting up faster than potheads at a heavy metal concert. My pupils must have dilated, because the colors of my bedroom suddenly grew extremely vivid. The now blinding light streaming in through the open window highlighted the silky, black hair styled sexily on top of her head. And as the amount of blood surging into my penis starved my brain of oxygen, I started to feel lightheaded. It was a good thing I was already sitting down, or I might have fainted.

Along for the ride, I had no idea how long Tiffany intended to keep this up, or how much more I could handle before something inside me broke. The flashes of arousal the tantalizing teen's talented tongue produced in me were like sticks of dynamite being shipped straight to my brain every second. It worked overtime to reroute these shipments to other parts of my body - anything to keep the volatile, orgasmic materials away from the blasting trigger hidden deep within my mental cocoon. But there was only so much space to go around. And those other parts of my body were quickly filling up.

My balls were tingling. A fullness that had started in my groin spilled over to my torso and created a buzzing sensation in my stomach. When that same fullness reached my pounding chest, it crowded out my lungs and made breathing a chore. Warmth spread all over my body, extending to my furthest extremities. The hairs on my arms and legs stood up, and my fingers and toes started twitching. And she just kept licking.

My cock, flexing and throbbing with need, was able to conjure a shiny bead of pre-cum. It was doing everything in its power to hasten me to my peak. But without that trigger, it could only make preparations and be ready to perform when the time came. Whenever flashes of the erotic scene playing out before me did break through the cocoon, my mental defenses fought with my body over control of my ultimate pleasure. My subconscious deployed proactive measures to intercept the stray thoughts and destroy them before they could even manifest. And she just kept licking.

This arms race, as had been happening a lot lately, allowed my arousal to escalate far beyond what most people would have been able to sustain without having an orgasm. My younger self would have filed this condition under an extreme form of blue balls. Stroking myself frantically, I would have rushed to relieve the condition as quickly as possible and let fret and worry seep in about it not happening fast enough.

When the pressure had reached a point where something had to give way inside me, something did. But it was not at all what I expected.

It's like I was standing in a large stream holding onto a precious package that the rushing waters were trying to tear out of my grasp. The package was my orgasm, and the rising waters represented my building arousal. But just as my resistance was faltering, instead of losing my grip on the package, something spectacular happened.

Still cradling the package in my arms, I stopped fighting and surrendered my whole self to the surge - letting the oncoming river carry me downstream. At once, the feeling of discomfort - that urgent need for relief - melted away, and I felt something else...something better. It's not that the orgasmic pressure inside me wasn't still there. But the question of how that pressure was going to be relieved faded into a void of meaninglessness. It's like I didn't have to cum anymore - or didn't care to. Rather, I could just sit there and let the arousal Tiffany was producing between my legs wash over me, fill me, saturate me.

Growing accustomed to the feeling, I started to accept this Zenlike state I found myself in. I closed my eyes and smiled serenely. Perhaps this river of arousal wasn't so bad after all!

As I got older, I grew to appreciate how my body related to and processed arousal. And it turns out, women also greatly appreciate such an ability. That's because, when it came to sex, I was able to - ahem - perform, for extended periods without a dip in potency. That ability served me well on countless occasions in my life - whether I was bringing a single lover to her peak over and over during a romantic weekend in the mountains or tending to an entire house full of young co-eds in desperate need of my unique services. But that's a story for another time.

Still getting used to this incredible, new plane of euphoria, it took my mind a second to register when my partner altered her pattern of motion. I was not privy to her plans or intentions. But on her own accord, she must have decided that my substantial sapling had received a sufficient number of licks. Randomly, the next time she reached the top, she strained her neck upwards once again. But this time, she did not settle for another mere kiss of my tip. Instead, she opened her mouth wide and allowed the head of my cock to slip inside.

Swimming back toward reality, I forced my eyes to focus again and looked down. But the scene below me was incomprehensible. I couldn't see my entire cock anymore. Its head had been enveloped in a silky, new warmth. A buxom, raven-haired beauty had considerately wrapped her plump lips around the upper part of my shaft.

It took me a second to even register that the topless girl servicing me with her mouth was Tiffany Lennox. But even then, I had trouble reconciling the image. Tiffany would never do something like this. She was usually such a dominant presence. Everyone always bowed to her will. But unless my eyes were deceiving me, there she was, the queen of the school, nearly naked and bowing between my legs.

Having just finished giving my cock an intimate tongue bath, she stilled her tongue - probably to give it a break from the stimulating workout. It was now resting against and getting acquainted with the spongy underside of my flesh mushroom. Adding to the slightly salty, testosterone-infused bodily secretions it had already absorbed, the flavor of my slippery pre-cum now spread across her taste buds.

Things kind of stalled out at that point. How was I supposed to know the next phase of giving a blowjob is bobbing your head up and down to generate friction? If Tiffany knew, she sure wasn't putting that knowledge to very good use. Or maybe this was as far as she was willing to let anything penetrate her mouth.

Since some of her hair had fallen loose and was hanging down to partially block my view, I couldn't really tell what was going on or why she had stopped. Reaching up with one hand, I gently brushed the silky black strands out of the way and tucked them back over her ear. What I revealed told the tale. The signs on her face and body were familiar to me, even if few other people in the world had ever seen them on her. I recognized them because I had seen them before on other girls. Tiffany was aroused!

Her pupils were growing just as wide and restless as mine had been a few seconds ago. She was breathing through her nose, more heavily than was necessary for the amount of physical activity she had been engaging in. Because of the seal her gorgeous lips had formed around the upper part of my cock, every near pant she made altered the air pressure inside the cavity of her mouth and produced a sexy little tugging sensation all the way down my shaft. So that's why they call it cocksucking!

Watching her brow furrow slightly, I suspected that Riviera Dave wasn't quite finished with this girl. As if I needed any more evidence, just then, her eyes rolled back in her head, and she let out a sexy whimper. If you've never felt the vibrations of a girl moaning directly onto your cock, you should try it. I highly recommend it!

I had only ever known Tiffany to employ a select, few expressions. There was the polite, but obviously fake smile she had been wearing since she arrived at our house, which wasn't far off from the slightly more perky one she put on her face to cheer at sporting events. But most of the time, she walked around with a sneer of thinly veiled contempt for her inferior, fellow students.

But in her current position, her dignity could not be any more compromised. Her jaw was literally stuck wide open to accommodate my erection and a blush was forming on her cheeks. Her naked chest was rising and falling rapidly. On my pubes, I could feel the little puffs of air she was expelling from her cute, little nose.

Taking in the scene of Tiffany Lennox panting with need while also sucking on my cock, I had never felt so...powerful.

Sensing my eyes on her, she glanced up just as another pleasure wave washed over her. Expelling me from her mouth, she pursed her lips and furrowed her brow deeply in the effort to suppress another audible whimper. I needed no further confirmation. Her young, fertile body was capable of producing multiple diamonds. And as was usually the case, it would do exactly that before Dave's chemicals had run their course. By all accounts, whether she was ready or not, her little factory was already preparing to produce another glittering jewel.

Feeling especially cocky (how can you blame me?), I made a snap decision to make the ultimate proposition.

"You ok?" I asked, suppressing my amusement and trying to project genuine concern.

"Yeah, I'm fine," she replied, though it was quite unconvincing. Still propped on her knees, she was squirming her restless hips in response to the growing urgency between her legs.

"If you want, I can help you with that," I offered, acknowledging her obvious distress before proceeding with a trembling voice, "we could help each other, you know. Like...with sex?"

Tiffany's eyes darted down at my pristine, glistening erection. And though she declined my offer, it took her several seconds to make up her mind. For that brief time, it felt like she was considering it.

She shook her head and said, "Well, I already told your sister, I'm not going all the way," but, after a long pause, added, "...mmm, well".

Already told my sister, eh? So, this encounter had all been part of Tiffany's hazing settlement after all! I could have said nothing and let her finish the blowjob she had started. But as a rather one-sided transaction, and after the significant pause she had just made, I wondered if she might be open to an alternative proposal - something that would more benefit us both. Assuming I would never get a chance like this again, I had to risk it.

"How about a contest, then?" I suggested, "Let's each try to get the other off using just one hand. If you can get me off first, you win. Your reward is that I'll tell Lucy you fulfilled your end of the deal, and you can leave without finishing my...other massage."

Her eyes narrowed, but she did not reject the proposal outright.

"And what if you win?"

"If I win, you have to have sex with me," I replied, "at least long enough to get me off." Then, taunting her, I added, "but if you don't think you're good enough to win a contest like that, I understand."

I knew I was taking a huge gamble by proposing this little contest. My arousal level was incredibly high, but so was hers. On that measure, we were on even footing. Having already given her an orgasm with my hand, I was supremely confident in my ability to do it again.

But as I said, cheerleaders are exceptionally competitive. She would be highly motivated to prove she could best me in a test of pleasure-giving. There was no telling how good she was at giving hand jobs, or how many secret tricks she was hiding up her sleeve. Well, they would be in her sleeve, if she had been wearing a shirt. But in her back pocket- Well, she wasn't wearing pants either. But you get the idea.

But she also didn't know about my new, Zenlike approach to arousal. Placing my faith in this freshly discovered ability, I assumed I could endure whatever tricks she threw at me; at least long enough to win the contest. That was my secret weapon. And if it did lead me to victory, I would gladly claim the ultimate prize! When she stood up and reached for her panties, I couldn't help but smile.

"Ok, I accept," she said, "with one condition." Watching her peel her panties down to reveal the last, most intimate part of her body, and stand looming completely naked over me, I would have agreed to any condition this goddess of teenage perfection required.

Nodding beside me toward the tub on the bed, she said, "I get to use that lotion on you."

Then she held out her hand to shake. I gulped, but reluctantly nodded my agreement and shook her hand. Since I had already slathered the lotion all over her naked breasts, it was only fair that she should get to return the favor by rubbing it into my cock. But suddenly, I wasn't so sure my cocoon could survive such a stimulating experience.

"Great!" she said cheerfully, scooting the tub over to make room and sitting beside me on the bed. The now completely naked goddess sat so close to me that her bare hip was grazing the outside of my right leg. Dipping her dainty, right hand into the tub, she pulled out a dollop of green lotion and hovered her hand right over my erection. I started to fret.

Grabbing my right hand, she placed it low on her abdomen, just above a dark patch of neatly trimmed pubic hair – her starting line.

"On three," she whispered into my ear with a sultry voice, "one...two...three!"

[student]

I don't know how, but neverdoubted managed to crank up the suspense beyond "maximum" again.

[Kazu]

Nope, sorry. Just ran out of surprises.

You lied or found more, since there was a surprise left, and a fun little competition it should be.