I Bet You I Could

“I bet I could suck his cock by the end of the week!” boasted Jessica, flipping her blonde hair behind her.

“You little slut!” laughed her best friend Amy, lightly pushing her, the two tumbling into each other. The pair were hanging out on Amy’s bed after school, as they had done almost every day since they were eight. Growing up together, the two would use the time to share whatever was on their mind, from fashion to fights with their parents. Now that they were eighteen, what was usually on their minds was sex.

Amy rolled off Jessica so that they were now laying down side by side, staring at the ceiling. “But, Mr. Crandall is, like, 10 years older than you for chrissakes, not to mention he could lose his job!”

“Yeah, but he still has a cock, doesn’t he?” Jessica pushed her tits up and together, straining her cleavage upward toward Amy. “And no matter who it’s on, the cock wants what it wants.” The two broke up into hysterical giggles once again.

Amy sat back up. “All right, Miss Confident, prove it. I’ll bet you fifty bucks.”

Jessica pursed her lips, intrigued. “If I suck off Mr. Crandall–”

“Within seven days,” interrupted Amy.

“–then you’ll give me fifty bucks?” finished Jessica. Amy nodded. “I’d do it for free!” she shouted, to more giggles from both.

“Fine,” eeked out Amy, her voice still choked with laughter. “I’ll up the challenge. You have to tell him up-front what you’re trying to do!”

Jessica’s eyebrows shot up. “That all you got?”

“And you can’t let him cum — and you have to tell him that too!” finished Amy, smirking. She stared at Jessica, sure that after all these years, she had finally outdared her.

Jessica’s glaze smoldered. She leaned in until she was inches away from her best friend’s face. She licked her lips. She spoke slowly, enunciating each word. “You are on.” The two broke up into loud guffaws, flopping back onto the bed and kicking their legs.

When Amy woke up the next morning, she had a text message waiting from Jessica. All it said was to get to Mr. Crandall’s class early. Not sure why, but willing to play along, Amy was already in her seat when, thirty seconds before the bell, Jessica walked in. Or strut in is how Amy would have put it. Jessica was wearing black “fuck me” boots that stopped just short of her knee. She moved slowly, shifting her balance from heel to toe; she gave the impression that she was 95% leg, and that it would all feel amazing wrapped around you. Her short black skirt reinforced the image. Above the skirt was the tiniest little black top, revealing her entire midriff, and pushing her cleavage out so that the tops of her breasts were visible nearly to the nipple. All noise and motion in the c lass stopped to watch her. With her blonde hair down to her shoulders, she was a dream image: the sex goddess and the sacrificial virgin and the porn star all rolled into one.

“Prostitute” is what Amy thought Jessica looked like. Although they were best friends, and even she had to admit that Jessica at the least looked very fuckable, she could not help but feel a secret stab of jealousy. All of her life, Amy had tried to look like Jessica. She had the blonde hair, and starved and exercised and did everything she could to have the same hard body, and sometimes they even got mistaken for sisters, but Amy knew she was always the ugly one.

No matter what she did her skin was always paler; her breasts, instead of Jessica’s perfect C cups, were always tragic Bs (B minuses if truth be told); her legs were never as long; her smile was always too toothy and small compared to Jessica’s toothpaste-commercial- perfection; her face too homely; always the girl next door, never Jessica, the perfect girl across the street. Amy felt anger, perhaps even tinged by desperation, that she would never have been able to pull off the silent admiration the class was giving Jessica right now.

Jessica pretended not to notice the classroom, instead proceeding to the front of the room. Mr. Crandall turned away from the chalkboard to face Jessica across his desk.

“Good morning, Mr. Crandall,” purred Jessica. Mr. Crandall furrowed his eyebrows, but was otherwise unmoved by the display in front of him.

“Good morning, Jessica. Um… are you sure what you’re wearing is appropriate for school?” he asked.

“What do you mean?” she returned, placing her palms on his desk and leaning forward. Her breasts were directly in front of him, presented on a platter, but he did not so much as glance down.

“I’m sorry, Jessica, but I think I’m going to have to refer you to the vice-principal for a dress code violation.”

“You don’t have to do that, do you, Mr. Crandall?” She gave him a puppy dog look.

“I’m sorry, school policy.” He shrugged his shoulders, the diffident I’m-only-doing-my-job attitude.

Jessica lowered her voice. “Wouldn’t you rather I suck your cock?” Amy, sitting in the front row, could just barely hear. The entire class leaned forward, all sensing that something gossip worthy was happening, and wanting to be able to say later that they had seen it firsthand.

“What?” Mr. Crandall jumped. Jessica leaned in even more, so that she was almost whispering in his ear.

“I’m going to suck your cock, Mr. Crandall, until you’re writhing and moaning with pleasure, but even then, I’m not going to let you cum.”

Mr. Crandall jumped back, visibly flustered at last. “Miss Walsh, you are going straight to the principal. I hope you come back not only more appropriately dressed but also with a more appropriate grasp of what is and what is not proper conversation between student and teacher!”

“Yes, sir,” Jessica said, putting her head down and turning toward the door. Though she looked contrite, slinking away, Amy could swear that Jessica was smirking.

That afternoon the two were once again in Amy’s bed, rowdy as can be. “I can’t believe you told him you wanted to blow him!” Amy yelled, mock-hitting her with a pillow.

Jessica half-smiled, her expression mysterious. “You’re the one who dared me.”

“And the way you were dressed! Every guy in that room wanted to bend you over and fuck you there, and probably even some of the girls.” The two broke up into laughter over this, as the lesbian tendencies of some of the less attractive girls at school was a common joke between them.

“Are you really going to go through with it?” Amy’s tone showed she was more serious than she meant to be.

“Oh yeah,” Jessica responded. “It’s a matter of pride now, and besides, like we always say, he is pretty cute. Just barely thirty, and I think he works out…” she trailed off, staring into the distance.

“I still don’t think you can do it before the week’s up — and with your suspension tomorrow, you have even less time.”

Jessica refocused on Amy, her half-smile returning. “Just watch and learn.” Silence held, and then both started laughing uncontrollably.

Because of her suspension, her parents would not let Jessica come over on Tuesday, and so it was not until the day after in Mr. Crandall’s class that the two were able to see each other. Again, Amy was already sitting when Jessica showed up, but this time, she caused no commotion and made no detours no the way to her seat, right next to Amy.

The two said quick hellos to each other, right as the bell rang to start class. “Giving up already?” teased Amy, pushing her tongue into her cheek to make it clear what she meant. Jessica stuck her own tongue out at her in reply, and then faced forward.

Class droned on. Amy stopped paying attention, looking out the window, looking around the room, looking at her desk. Every so often she would glance to her side to look at Jessica, wondering if she was going to try something in class again. Jessica was wearing a plain cotton blouse and a denim skirt, and though it had climbed high enough to reveal half of an attractive thigh, it did not scream sex by any means. Her hair was in a simple pony-tail. Her make-up was light. Idly, Amy thought about borrowing Jessica’s skirt and getting fucked while wearing it. She was between boyfriends, but thought she could find someone. For starters, she would accessorize a little better than Jessica had.

Suddenly, something odd caught Amy’s eye. Mr. Crandall looked like maybe he was feeling a little sick, and he was pausing too much as he spoke. His gaze was low, and although Amy could not have pinpointed what was strange about him, for starters he was violating his own public speaking tip he had given to them about moving your glance around the room to make it look like you were talking to everybody. Amy followed Mr. Crandall’s gaze in surprise — he was staring straight at Jessica’s crotch.

Jessica was slouching down in her chair just a little lower than seemed natural, her legs stretching out in front of her. The skirt had ridden even farther, so that now it was covering only the top few inches of her thigh. Jessica’s unbroken tan was very clearly visible from Amy’s position to the left of her. More revealing, however, must have been Mr. Crandall’s position — Jessica was making no effort to keep her legs together.

Amy’s eyes bugged out, and she almost whirled on her when she realized the show that Jessica must be giving him. The two had been moved to the front of the class weeks ago to stop them from chatting in the back — and now Jessica was using it to help her win the bet. And she thought the bitch had given up!

Mr. Crandall was trying to be stoic. He certainly had not been trying to catch a peek — he considered himself professional to the utmost — but he could not help but notice Jessica, right in front of him. As class went on, no matter how much he tried to focus on his lecture, he found his attention kept coming back to her, as her skirt slowly inched up her legs. It was like a curtain slowly being drawn to reveal a fabulous prize, or a slow-motion crawl to disaster; he could not help but look, and the higher and higher her skirt got, the longer his stares lasted.

He was not sure if Jessica even realized what was happening. Her eyes wandered the room occasionally, the normal half-attention he had come to expect from his students. Her skirt crept up slowly and without any seeming effort from her; it could easily be the unknowing mistake of blossoming young womanhood.

As a particular blossom of young womanhood came closer to being viewed, Mr. Crandall was having trouble continuing his lecture. Jessica’s legs were spread, revealing the cream color of her inner thighs. Her legs were long and only barely tapered, the skin completely smooth, the tissue devoid of any hint of fat. Mr. Crandall’s gaze bored into her.

He could see the slightest hint of her vagina, a shadow. If her skirt lifted any more, he would be able to see everything, and he was very interested in seeing everything. Without his control, he felt himself mentally urging the last bit of fabric to move, attempting to will her skirt up. Languidly, her legs stretched outward, her skirt climbing a millimeter, then two, then tree. Mr. Crandall held his breath. Her pussy blinked into view.

Although he could not claim to have seen that many, hers did seem very nice. It was completely shaven, though right above her lips, he thought he saw the faintest little square of blonde hair, almost translucent against her skin. The lips themselves were smallish and close together, with her clit proud and prominent above them. Mr. Crandall could not help but wonder if she was wet (there was too much shadow to be sure), or how hot her pussy would be to the touch. He wondered how it would feel to push his finger between those lips, or give them a gentle lick. His mental image was so perfect it staggered him, and he had to lean against his desk for support.

The class was uncomfortable, students beginning to murmur and fidget. Jessica, either oblivious or feigning innocence, politely asked, “Mr. Crandall, are you ok?”

“Yes, yes I’m fine,” he responded, unsure whether to glower at her or to pretend nothing was happening.

Jessica smiled. She brought her hand toward her face, biting on the end of her pencil. Aside from the fact that her entire pussy was on display (which no one else was noticing), she was the picture of studiousness.

Her expression hardened. Slowly, she began to slide the pencil into her mouth, so that instead of just biting on the eraser, suddenly an inch of the pencil had disappeared. Her lips pursed around it. To Mr. Crandall it looked like she was actually sucking on it. She began to slowly, lazily, push and pull that inch of her pencil in and out of her mouth. To his stressed out mind (absently, he wondered when he’d last had any kind of sex, and realized that if he did not know, it had been a while), it looked very much like —

The bell rang, breaking the moment. Instantly, Jessica’s legs snapped shut, and she began to bolt for the door, lost in the general crowd of students as everyone tried to leave. Mr. Crandall was spared having to acknowledge what happened, but as he sat down and tried to calm himself, he wondered what he was going to do if this kind of thing happened in the future.

In Amy’s room that afternoon, the situation was more tense than usual. “I can’t believe you showed him your pussy in front of everybody!” Amy said.

“What’s the big deal? It’s not like no boy has ever seen my pussy before,” Jessica said, her tone lightly mocking, the faux-here’s-a-big-secret voice. Amy pouted slightly, stopping her pacing to sit down next to Jessica. “Are you jealous?” Jessica meant it as a jab, but quickly softened when Amy jumped. Maybe she had hit on something after all.

Amy’s heart fluttered slightly. She was not sure what she was feeling — jealousy, maybe. For Mr. Crandall’s attention? Maybe; she had, after all, had a crush on him first.

Amy’s tremor dissolved. “No,” she said defiantly. “Why would I be jealous? It’s not like you’ve never sucked a cock before, either.” She smirked.

Jessica laughed, glad that the squall between her and her friend had passed. “It’s true, it’s true. But if you are jealous, we can call off the bet, and I’ll promise not to suck Mr. Crandall off — and it’ll only cost you one hundred dollars.”

“Thief!” shouted Amy, but now they both were laughing, falling on each other. They rolled on the bed, tickling and grabbing as usual.

As their giggles died down, they were side by side on the bed, lightly entwined. “So how do you plan to seal the deal?” Amy asked, genuinely curious.

“Ah-ah-ah,” replied Jessica, “you’ll see.”

The next day, class passed close to normally. Mr. Crandall, unsure whether he was hoping for a repeat performance or not, struggled also with whether he should try to talk to Jessica about what had been going on, or if perhaps he should seek out advice from one of his colleagues, or one of the administrators. His lecture, if perhaps a little more dull than usual, proceeded without interruption.

Amy eyed Jessica for her next move, but she was also rather subdued in class, taking an occasional note, but otherwise sitting quietly. And although her cheerleading outfit showed off plenty, from what Amy could tell, Jessica was not giving any extra show. And although the outfit fit her well and (again, though Amy was not even fully aware she had the thought) made Jessica look quite fuckable, there was nothing strange about it. Jessica was one of about twenty girls wearing the outfit for a pep rally scheduled during seventh period that day.

The only thing that veered at all from normal was after class, when instead of rushing out the door, Jessica (hesitatingly, or at least feigning hesitation) approached Mr. Crandall’s desk. Mr. Crandall, resolving to project professionalism, turned to speak to her, but found he had a lump in his throat (and so far, thankfully, nowhere else). Being so close to her, he was taken by how the blonde in her hair matched the gold in her cheerleading outfit, and how much youthful vigor seemed to shine from her.

From the beginning, she was in control of the conversation.

“Mr. Crandall, I just want to apologize for my behavior the past couple of days.” Mr. Crandall, who was worried about how much of him was not sorry about her behavior, attempted to look consolatory. “It’s just there’s been a lot going on in my life, and I’ve been having a lot of trouble lately.” He attempted to shift his expression to concern, with more success than he had with consolatory, but he still could not help but notice how low the neckline of her cheerleading outfit plunged. “I really respect you, Mr. Crandall. Could I maybe come by to talk to you after school today? I really need to talk to an adult that I can trust.”

Alarm bells were going off in his head. And yet, she seemed so sincere, and teachers were supposed to be there to help students with personal problems, and if she really was in trouble, it would be his legal responsibility to help as well, and not just moral (mandatory reporting and all that). He hoped his intentions were pure when he responded, “Of course, Jessica. I’ll offer whatever help I can. Just come on by my classroom after school, that will be fine.”

“Thank you, Mr. Crandall,” said Jessica, heading for the door. Amy, who realized she had been dawdling, quickly followed.

At almost exactly 3 pm, Jessica returned to Mr. Crandall’s classroom. Although it was obvious she had showered, her skin was still a little flushed from the work of the routine the cheerleaders had put on for the pep rally. Mr. Crandall looked up from his desk, pretending he had been grading, when in truth, he had been eyeing the clock, as nervous for Jessica’s arrival as if he were sixteen again and going on his first date. “Come in, Amy!” he said, “Have a seat.”

“Thank you, Mr. Crandall,” she said, moving across the room. “I’m sorry I’m a little late, but I wanted to grab a quick shower after the pep rally today.” She stopped in front of his desk, but rather than sit down at one of the student desks near it, she leaned back against it.

“Yes, you looked great out there,” he mentally stopped, “I mean, you all, the team, looked great, you’ve all been working hard.” He was sounding as awkward as his eighteen-year-old self, as well.

“Yeah, all my muscles are killing me,” she said, stretching out her arms and puffing out her chest, mimicking the contortions of an early wake-up. The tops of her breasts strained upward and outward.

“So you mentioned you wanted to talk to me about something?” Mr. Crandall said, getting up and walking around his desk, so that he was directly in front of Jessica. He leaned back as well, trying to appear casual.

“Yeah, you may have noticed I’ve been acting a little odd lately,” responded Jessica.

“Yes, a little.”

Jessica sat down on the edge of the desk. Pushing her hands in her lap, her skirt was held down and her panties kept just out of view, but most the skin of her legs was in view again, her legs dangling, slightly akimbo. It was, Mr. Crandall thought, the way her legs might hang if someone were fucking her on the edge of a bed. He cursed himself, but he could not find a way to stop his thoughts.

“The thing is, Mr. Crandall, I’m really, really attracted to you, and I just don’t know what to do about it.”

Mr. Crandall stopped breathing and his heart, as if to compensate, began pumping at double-speed. Alarm klaxons went off in his head that he was entering dangerous territory.

“I think that’s normal, Jessica, and very flattering. I think plenty of girls have crushes on their teachers, but it’s important to remember that I am your teacher, and that these things pass.” He wondered if he was being sensitive enough. It was important to turn her away without damaging her self-esteem. At least, that was what the loudest voice in his head was saying. He struggled to ignore the whisper which said other things.

He could not help but stare at her. In the afternoon sun, her skin glowing amber, she seemed like a goddess. He watched a single drop of liquid appear on her upper thigh and run lazy zig-zags down her leg. He did not know if it was left over water from her shower, or if her pussy was moist and leaking. He had to fight the irrational urge to scoop the drop up on his finger and taste it.

“I think it’s slightly more than a crush, Mr. Crandall,” Jessica said, lowering her voice, attempting to sound sultry. Their gaze held for a few moments. Needing to break the spell, Mr. Crandall moved to stand up. At the same moment, Jessica yelped in pain, grabbing her upper thigh.

“What is it?” he asked, concern evident.

“Ow, cramp, ow, ow, ow!” Jessica had crunched over her right leg, holding it close to her, pain evident on her face.

Not thinking, but simply following his instinct to help, Mr. Crandall became clinical. “Here, let me.” He quickly pushed her own hands off of her thigh, and set to work vigorously kneading the skin. “You have to rub these out quickly.”

Jessica smirked, but Mr. Crandall was too intent on his task to notice. She did not lean back, but continued to huddle so that she nearly right on top of him. They could feel each other’s breath. He stretched and massaged her leg, attempting to relieve the cramp. “Feeling better?”

“You have great hands, Mr. Crandall.” She slid her left leg away from her right leg, opening herself up, and causing her skirt to life. Her pussy blinked into view. She was not wearing any panties.

Mr. Crandall stopped rubbing, but he did not remove his hands. He was mesmerized by the appearance of her pussy, like he was under the power of a hypnotist, or a snake charmer. It was puffier than he remembered, and glistened, but it still looked so fresh and so clean. Suddenly he noticed how close his fingers were to it.

“Please touch me, Mr. Crandall,” Jessica whispered, grabbing his hand and pushing it up toward her.

His hand cupped her pubis, his middle finger entering her furrow, squishing just between her pussy lips. Jessica squeaked. Still holding his hand in place, she began to gyrate her hips, grinding her pussy against his hand. Mr. Crandall stared, dumbstruck, at his hand and her pussy.

“Do you feel how wet I am, Mr. Crandall?” she purred. “Do you feel how soft I am? I shave every day.” Her pussy was very wet and very soft. “Mmmmm,” she moaned, closing her eyes briefly. “Let me feel your cock.” She brought up her other arm and grabbed Mr. Crandall’s bulge through his pants. She could feel his cock’s outline through the soft material of his slacks. She began to gently squeeze his lump in synch with humping his hand.

Mr. Crandall raised his gaze to look at Jessica. Although he still was making no effort to leave, and was passively, at least, rubbing her pussy, and was sporting a full erection, his expression was one of fear, like a rabbit staring down a wolf. Jessica met his gaze, her eyes half-lidded, her mouth smirking. She looked confident and seductive. She writhed on his hand, and gently pushed down on it. His middle finger, rather than just creasing her furrow, slipped inside her vagina, sliding past her love-ring. Her pussy was so tight it was almost uncomfortable for his finger, like having a rubber-band constricting it.

She stopped moving her hips. Her gaze dared him to move his finger — to curl it, looking for her g-spot, or push in deeper, or even pull out a little. His hand did not move.

The lump in her other hand was appreciable. Rather than just squeeze it, she wrapped her hand around it, like she was offering a handshake, and began to tug, lightly jacking him off. His legs began to shake under him. His cock felt like a volcano, like it was tapped into the primeval blaze at the center of the earth, and that at any moment it could spurt. And she had just barely begun touching him.

“Do you want me to suck you, Mr. Crandall?” Jessica murmured. Whatever was left of Mr. Crandall’s sanity suddenly broke. He began ripping at his pants, haphazardly undoing his belt before shoving his pants down. His cock leapt to attention, glistening.

“Oooh, you do have a nice one,” Jessica cooed, holding his cock in her hand briefly, as if admiring it. It was good-sized — not a porn star’s cock, but certainly nice enough at slightly more than six inches length and a good thickness. His pubic hair was closely trimmed and lined just the base of his cock and the tops of his balls. Jessica swooped down upon his cock.

Mr. Crandall cried out as his cock disappeared into her mouth, sliding all the way back in one movement. His hands fell into her blonde hair and grabbed, and he began to buck into her mouth. Jessica squealed, but it was a good sound; she was not used to men taking control and needing her so quickly. She held her lips over her teeth and tight together, trying to create suction for him as he pounded into her. Her hands gripped his buttocks, her nails leaving white trail marks in his skin. She began to pull him into her almost as frantically as he was pushing into her, her breath escaping in hot bursts through her nostrils.

Her bet with Amy had included that she could not let Mr. Crandall cum, but she did not have a clue how she was going to pull that off. Mr. Crandall no longer seemed to be in conscious control of his body, and by the way he was humping her, he did not plan to last long. He was holding her tightly, too — she could barely breathe.

She grabbed his hands, and after a few more strokes, he stopped pushing on her. She gasped as his cock fell from her lips, saliva and pre-cum all across her lips and chin, and more puddled on the ground. “Mr. Crandall, you can’t come in my mouth,” she panted.

Mr. Crandall let out a moan, not of anger or aggression, but of mindless need. He put his hands on her shoulders and began to push, attempting to make her lay backward. His body also pushed into hers, his cock stabbing at her wildly, hitting her knee, and then her abdomen, and then her thigh. It was like Mr. Crandall had become some sort of caveman — no language, no civility, just the urgent need to fuck.

He began to hump the air, his cock smearing saliva and pre-cum against her thigh as it hit her. He was not hurting her, but the pressure was mounting, and she was starting to have to lean back against it. His cock was inches from her pussy. “Mr. Crandall, really, I don’t think we should be having sex!” She tried to sound shocked and prim.

Of course, she was anything but prim. She had fucked her share of cocks (and sucked a lot more), but she was no slut. She didn’t just fuck whoever, whenever.

She realized what she had to do. It was something she had done before with more than one aggressive boyfriend in more than one parked car.

“Here, try this instead.” She quickly contorted to the side to escape his hands, and then using her hands, angled his cock upward. As he thrust forward, his cock disappeared into her mouth. She slurped around it.

He began to buck and moan, really fucking her mouth. She began to knead his balls, moaning through the cock in her mouth, slurping on him and lashing him with her tongue.

Suddenly, Mr. Crandall stopped jerking. The first spurt hit her in the back of the throat, then there were more and more. Jessica swallowed as quickly as she could, licking her lips to get the saltiness.

Mr. Crandall collapsed into a chair, shock on his face.

A few minutes later, just outside the school’s gate, Amy was impatiently pacing when Jessica caught up to her. “Did you do it?” she asked.

Smiling and flushed, Jessica nodded. “Where’s your proof?” Amy asked, slyly. With that, Jessica stopped walking, turned to face her friend, put her hands on either side Amy’s face, and before she could react, moved her mouth against hers. The kiss was instantly open-mouthed — tongues wrestling and exploring. It lasted thirty seconds, before Jessica dropped her hands and stepped back. Now both were out of breath. Amy was stunned.

“I thought we agreed that you couldn’t let him cum?”

Jessica had lost fifty bucks.