Graduation Ch. 02

The acknowledgement that Caleb had something to do with Penny's newfound love of working out was flattering, of course, but it led him to the second stage for entirely different reasons. The full weight of what her fantasy meant sank in for him, causing his brain to crank forward and imagine an even hotter set of far more plausible possibilities.

"It's only gotten worse, you know." Penny's voice started to take on a low, syrupy affectation. "Because when I got tired and sweaty after my last couple of workouts, I'd think back to last weekend, all the times I'd have to lay still and catch my breath, glistening with sweat and sperm..."

Caleb heard a sharp sigh on the other end of the phone; entering into the third stage, he swore there were fish swimming inside his head.

"It makes me hot, remembering how much, how hard I can make you shoot," she purred. "You remember that first night, don't you? When you covered me in your sweet cream, and I looked so good to you that you just had to pump that beautiful cock of yours between my slick, sticky titties until you blasted me again?"

Holy shit did Caleb remember. One part of him remembered so well it threatened to detach itself from him and fly around the world fast enough to travel back in time and relive it.

"You know, Caleb," Penny snarked in good nature, "it's hard to get a good round of phone sex going when the other guy won't talk."

Instead of an apology, Caleb stammered out "I've got a home gym in my basement."

"Really?" She drew out the word as long as the sexy, shit-eating grin that had to be on her face at that moment.

"And my Mom's friend is throwing a barbecue today, so she and Becca are gonna be there until 10 or 11."

"Hmm..."

"I mean, it wouldn't be EXACTLY like your fantasy, I'm sure. For one thing it's private."

"Right, and we'd be taking a lot of crazy chances here. A neighbor could see me coming in."

"Or my parents could come home early."

"Or, they come home long after I'm gone, but there's something I left behind."

"Or some kind of mess."

"Yeah, overall, it seems like a dumb risk."

"Super dumb."

"Text me when they leave?"

"Absolutely."

* * * * *

They ended up leaving at around 3. By then, of course, Caleb was showered, shaved, fed, and over the rest of his hangover; all he worried about was the sudden twinge of panic in his gut when Becca half-jokingly wondered what he was getting dressed up for. Penny was ostensibly coming over to work out with him, but he had lots of time after the shower he needed to take, and thought he'd look suspicious hanging out in his workout clothes all day. Instead, he opted for a blue patterned v-neck tee from Banana Republic and a pair of white shorts. He almost applied cologne out of habit before dressing, but at the last second decided to wait until he texted Penny the all-clear. Becca's gentle tease made him wonder how suspicious she would have been if he had worn cologne, and reminded him of the frayed tightrope he was attempting to walk by inviting Penny over.

But it all passed, the parents left, and after giving it five minutes to assure himself they weren't coming back, Caleb sent the text: "All clear. You need the address?"

That done, Caleb went back to his room to spray some cologne on his wrist and neck. Penny's apartment was fifteen minutes out, plus she probably had to get ready, so he figured he had time for a couple of quick Overwatch games while he waited. He fired up his PS4, and just moments after the home screen appeared, his phone buzzed:

>Thanks, but I think I have it.

The doorbell rang.

"No way," Caleb thought aloud. He got up and walked to the front door.

Through the glass of the front door, he saw Penny in a grey tee-shirt and a small gym bag slung over her shoulder. She sipped from a Slurpee cup, the straw slipping back and forth across her mouth.

"That was fast," Caleb said, opening the door.

"Where's your room?" asked Penny. She set her cherry Slurpee down on the foyer table, dropped her gym bag nearby.

"Make a right, and another right," said Caleb, shutting and locking the door. "I thought you wanted to use the gym?"

"Well, I thought your parents were leaving much earlier." Without stopping, Penny unsnapped her cuffed denim shorts, hooked her thumbs into the waist, and pushed them down her tight, round ass.

Stepping over her shorts and panties, Caleb glanced down and saw that her gusset was dark and damp. "Oh, shit," he acknowledged.

"Yeah, this might get a little dark." With one hand, Penny pulled Caleb into his room by the collar of his shirt and shoved her tongue down his throat, gripping the back of his head with her other hand. He reciprocated, sliding his hands downward to grope her cotton-clad chest, eventually breaking from her mouth altogether to kiss a trail down to those perfect tits.

"Doesn't look like you were expecting company," smirked Penny as he nibbled on the excited nubs poking through her shirt. His TV was still on, tuned to the PlayStation home screen; his PS4 controller was on the futon, plugged into a charging cable that hazardously crossed the length of the room. Odd items of laundry and trash—a used shirt here, a small bag of chips there—were strewn about the floor, and his twin bed at the far end of the room sat unmade, its white/navy comforter haphazardly pulled aside to expose the fitted navy sheet underneath.

"I was gonna clean it today," said Caleb, reaching down for the hem of Penny's shirt.

"Sure you were." Before Caleb could get her shirt above her belly button, Penny was pushing him across the room, past the TV—gracefully stepping over the charging cable—and onto his messy bed.

"After three and a half hours I just said 'screw it' and left." Penny crawled down Caleb's body, unsnapping his shorts. "Spent the last ten minutes just driving around your neighborhood, waiting for your text, because apparently I'm Glenn Close from Fatal Attraction now."

"I'm fine with that, just leave my pet rabbit alone."

Penny's eyes bugged in surprise, and she flashed an open-mouthed grin while she pulled Caleb's shorts away from his rigid cock and off of his legs.

"Becca—my stepmom," he explained, "she loves that movie."

"Thanks for not making me feel old," she said. She crawled back up his body and rose on top of him, blocking his view of the "WORK HARD, DREAM BIG" motivational poster above the foot of his bed. "Maybe I'll take a little pity on you."

"Do what you gotta do, Penny."

"Excuse me?"

Caleb watched his teacher's eyes sharpen from behind her glasses and he twitched against her powerful grip. "Sorry, Miss Piper," he said. "Won't happen again, I promise."

"I should hope not, Caleb," she sexily condescended, before plugging him into her with a loud gasp. "FUCK, I missed this dick!"

Penny—no, Miss Piper wasn't easing into this one; she grabbed tight to Caleb's shoulders and rode him like she was on a moonbounce. Her aggression took Caleb by surprise; he had to keep telling himself to breathe, even if those breaths came loud and quick and ragged as his steel cock was struck over and again within his teacher's tight tinderbox.

"You like that, don't you?" She was almost snarling, delirious from frustration and relief and pure literal fucking joy, "Doesn't feel like your right hand at all, does it? Such a shame; all those thick, beautiful loads, wasted on a computer screen that can't appreciate them..."

A jangle sounded from his TV; Chris was inviting him to play Overwatch. Caleb turned his head a little further and noticed his bedroom door was still open.

"Eyes forward, Caleb!" Miss Piper took Caleb by his chin and turned his attention back to her dick-drunk face. "You're on MY time now!" His eyes drifted down to Miss Piper's breasts, bouncing, applauding him from within the confines of her tee. He reached up to return their adulation, only for Miss Piper to clamp down on his forearms with a sly smile and a shake of her head before she threw her head back and moaned with increasing satisfaction.

At this point it became clear to Caleb that he was Miss Piper's human dildo. Given how he was treated by Danielle Carlson and how he felt about all the women he turned down for being so aggressive, it was only natural for some small voice within himself to break ranks with his raging libido and say "This is wrong! This isn't what we signed up for! You have to tell her to stop!" There was a certain glint within Miss Piper's impish eyes, though, the relief of someone drinking from a garden hose after a hundred days in the desert, that told him enough to bring that small voice back in line. Unfortunately, that same glint also triggered a bunch of different ideas that pushed his balls to a breaking point, forcing him to shut his eyes and do math problems in his head. What good was a human dildo that couldn't get its owner off?

"Ooh, Caleb! Are you cumming already?"

"If you slow down a bit," he groaned through clenched teeth, "I can hold out."

"I don't want you to." Miss Piper slipped off of Caleb and began to slide back and forth across his sopping member. "Where do you want to put it?"

"You know where."

"I think I do..." Miss Piper straightened her back, thrusting out her covered chest. Continuing her wet grind on his prick, she reached down and took her shirt by the hem, dragging it slowly up her smooth, trim stomach. "You want to cum all over these titties, right?" She pulled her shirt up past the underside of her breasts, stretching it taut against her nipples. "You wanna cover my girls with your hot junk?"

"Hell yes, Miss Piper."

"Well, you should have thought of that before you chose those fucking porn stars over me!" Penny dropped her shirt and ground on him even harder, and Caleb burst out laughing over Miss Piper's ingeniously bitchy tease.

She clutched his t-shirt, rubbing the soft fabric between her fingers. "Such a nice shirt, Caleb. I think it'd look even better with some splashes of white on it." Caleb tilted his head forward and found that Miss Piper's puffy pussy lips had trapped his stiff cockhead directly over the hem of his tee.

"Oh, God, please don't make me cum all over my shirt, Miss Piper!" He'd have to do laundry! Which he had to do anyway, but would put him out for a whole five minutes!

"Don't?" Miss Piper sneered. "What a rude boy, jerking it to your pornstars, leaving me high and lonesome while you expose your poor computer to all sorts of nasty viruses. Give me one good reason why I shouldn't ruin this nice shirt!"

Caleb didn't have one, even though he was totally super desperate for one, honest. Of course he was shocked, SHOCKED, that his English teacher would be so depraved in her punishment for such a minor, and frankly expected offense...but wrong was wrong, and if it got her off and triggered those amazing faces and moans she made in the throes of her orgasm, he supposed his punishment was only fair.

"You know what?" She leaned down, into his face, just out of reach of his tongue, cradling his head in her firm hands while her wet lips continued to slip and slide against him. "You look so cute when you're scared, that I think if you ask really nicely, I might let you cum in my mouth instead."

The shock of Miss Piper's denial had held him back a bit, but at this point, there was so much pressure building up in his dick Caleb thought it might explode outward rather than upward. "Please, Miss Piper!"

"Please what?"

"Please let me cum in your mouth!"

"Is that what you want?" she asked. "You wanna flood my throat with your pervy teen spunk?"

Caleb nodded vigorously within her grip.

"Are you gonna stop jerking off to those plastic skanks that pretend to be like me?"

"Yes, Miss Piper!"

"Are you gonna stop being a little bitch boy and call me whenever you get hard?"

"Fuck! Yes, Miss Piper!" He had to force himself not to laugh at Miss Piper calling him "bitch boy."

"Then apologize!"

"I'm sorry!"

"'I'm sorry' who?"

"I'm sorry...Miss Piper!"

Miss Piper shook her head, pulling herself back up. "I'm not the one you should be apologizing to!" She got off Caleb's dick just in time, knee-walking forward until her swollen pink slit hovered over his mouth. Her hands returned to the back of his head and pushed it upwards, flooding his mouth with the tangy-sweetness of her sex. Caleb shoved his tongue up inside her tunnel, lapping and twisting within her while she cried out and ground herself on his face, the fine sand-colored down above her cunt tickling his nose. He thrusted his hips upward, trying to luck into friction that wasn't there.

With Caleb showing her pussy sufficient remorse, Miss Piper was now ready to show him mercy; she flipped over to face his cock, sitting back down on his mouth before devouring his sopping member. Caleb moaned into her, which caused Miss Piper to moan against him while she corkscrewed her tongue around his throbbing shaft, which eventually caused Caleb to blow so hard he saw entire galaxies. He could only faintly hear Miss Piper gag against the first shot of his load because he was groaning so loud, and because he was groaning against her clit, that triggered Miss Piper's own release, cascading into an orgasmic ouroboros that left them twitching and crying and cumming into each other until she finally rolled off him. They were both out of breath, sticky with each other's releases, and comfortably cramped on his small bed.

When he was ready, Caleb flipped himself around to come face to face with a breathless Penny, getting a closer look at the spend that had stained the corner of her mouth and the bottom of her lip. She had a look on her face like she just realized there was a warm gun in her hand and a cold body at her feet. "I am...so sorry," she panted, "I don't know...where that came from."

"Can you find out? Because that was fucking awesome." Caleb could somehow feel his pupils dilate a bit on that last word.

Penny chuckled sardonically. "Well," she admitted, "clearly you were enjoying yourself, but still, there was no warning, no real consent—"

"Would you feel better if I said I was asking for it? Dressing up like I do?"

Penny responded with a playful smack across his chest. "I'm serious. This is the kind of thing we have to be careful about if we're going to do this. It's weird enough that you were my student; it'd be messed up if I made you my sex slave on top of that."

Caleb nodded, and tried to think of an answer that showed his respect for where Penny was coming from as well as his insistence that she not kick herself too hard. But he couldn't concentrate because "Um, it's really hard to talk to you seriously when my stuff's dripping out of your mouth."

"Oh!" Penny collected his sperm with her finger, but stopped short of placing it in her mouth. "Actually, I feel like if I clean this off, I'll just make it worse."

"I got you." Caleb sat up and grabbed a box of tissues from his night table, which Penny used to wipe her finger clean. Caleb took one for himself as well and dabbed at the juices on his face, only because he didn't want her to feel weird about it. "Okay, so, yeah," he continued, "I did get a little freaked out at first. But I was cool because I know you'd never actually hurt me on purpose, and I could also tell you were really into it. It makes me hot to see you so turned on."

Penny shook her head, falling back against his mattress with a stupefied grin on her face.

"What?"

"I can't think of a single guy I've slept with who seemed to give a shit about whether or not I was turned on in bed, let alone be excited about it." She shook her head again, apparently still unable to process it. "How is it that the most generous lover I've ever had is a hormonal, college-bound football jock?"

The words escaped from Caleb's throat almost a full second after they formed in his mind: "The gay agenda?"

Before he finished saying it, he thought he'd have to explain that it was a joke about the benefits of growing up surrounded by strong, feminist women. But then Penny burst out laughing, hard enough to snort, smooching him on the cheek the second she was calm enough to do so.

He was glad he made her laugh; as someone both deeply invested in Penny and fully aware of how inappropriate their relationship was, if Caleb wasn't happy, he'd be offended on her behalf. He had spent the first half of last week running back all the nasty, pornographic shit they did together over that weekend, comparing himself to (what little he could stand to read of) the gentle love scenes his mother would write, packed with emotion and passion, silk bedsheets and red roses. Caleb had always assumed that that was how adults had sex, and that it was somehow inherently better than the movies he jerked off to because of true love or something.

It was obvious that Penny enjoyed herself that weekend; her words about being a man had stuck with him, suggesting that maybe there was real emotion and passion between all the dirty-talking and the tit-fucking and the cum-shotting. But "the most generous lover I've ever had?" That was some severe bullshit; Penny deserved better than that.

This didn't feel like the time or place, though, so Caleb continued. "Look, all I'm saying is, if you're taking me somewhere I don't wanna go, you can trust me to speak up, because I trust you to stop if I do. Okay?"

"Okay." Penny let out a deep lungful of air. "Let's also say, because I did make you a little uncomfortable, that I won't pull that dominating bitch routine again. Not without your permission."

"That's fine."

"And maybe I should let you...return the favor downstairs."

"Return the favor?"

"I mean...I could use a personal trainer when we start working out." Her fingers danced across his firm, clothed chest. "Someone who can push me past my limits, maybe? Because, you know, that's what all the best trainers do."

Caleb blinked. Something caught in his throat. He wasn't sure how he was able to insist that she didn't need to do that, but his first attempt sounded a lot like "Um, maybe we should take a break first?"

"Sure!" Penny pushed herself up and crawled over Caleb to the floor. "I'd love to see the rest of your house."

Caleb wasn't much of an ass man, but the t-shirt she wore drew extra emphasis to her round behind, and suddenly he was rethinking his suggestion to take a break. His rethink turned to naked regret when she innocently turned back to him, giving him a look at the way her trim hips narrowed down into her pussy, framed by her soft, neat bush.

"By the way," she said, stretching herself out, "I'm more than okay with you watching porn, and you don't need to call me every time you're in the mood. But you should call me more often; it's not nice to leave a girl hanging." She turned back around, giving him another view of her spectacular ass. Walking out the door, she threw him a smoldering over-the-shoulder look. "Also, clean your room, Caleb," she sizzled. "When I come in here again, I want it to be somewhere other than your twin bed."

Caleb resolved to actually clean his room that night.

* * * * *

Penny had a weekend gig as an at-home tutor when school was in session, giving her access to some of the nicest, most expensive homes in Westbrook Heights and neighboring towns and areas. Yet, whether out of genuine appreciation for the architecture, or just as part and parcel with her appreciation of her new hunky teenage side-piece, she liked the Bradstreet home the best. It was a cozy little single-story cottage with an open floor plan; the foyer led straight into a great room with a solid home theater and stereo setup. There was a small kitchen to the left that fed into a dining area, separated by an island counter. At the far end of the great room, a sliding glass door led out to the patio with an in-ground pool and jacuzzi. The door faced east, the flooring was light birch wood, and the walls were painted in bright blue colors; Penny could only imagine what it would be like to walk into this room on a sunny morning.