Graduation Ch. 01

She squealed, then giggled while he kissed his way back down. "There you go, you're getting it! Keep playing like that!" But he was already at the top of her breast, and she figured that was the end of it, which was okay because the old familiar tingles were starting to push upwards against the skin of her chest, desperate to feel the touch of the young man on top of her, and Caleb was about answer the caaaaaa...

"AAAAOOOohhh," she gasped when Caleb veered left, tonguing the crevasse where the side of her breast met her arm. "Oh YEAH, Caleb! Such a great tease!" She could feel him smile against her skin while he lifted her arm up to move into her side, brushing the thin line where her ribcage swelled into her breast with his tongue. "You really are a quick study!"

"Yeah," he said between licks. "It's totally that. I certainly didn't change my mind. At the last second. Because I thought I was going too fast."

"It's adorable how you think that makes a difference," she said. She cradled his head while he gently worked the arc around her ample titflesh. Her breaths were getting shorter and shorter. The tingles in her chest had blossomed into dull aches. And Penny could swear her heart was beating so hard she jiggled with each pump.

"Now try using your hands," she suggested, and naturally they went right back to her chest, kneading the fat and rolling her pebble-like nipples in their palms. This time, though, she was ready for them, letting out a sharp moan with his first squeeze, a smaller one with his second, the constant massage turning her short breaths audible.

"Ahh...see how responsive?" she sighed between her gasps for air. Now he was pinching her nipples, strumming them with his fingers. "Much more responsive...when you put...put the work in...more fun this way...don't you agree?"

He looked up again and nodded, proud, his own breath growing short. Then he moved his hands under her breasts, hoisting each one between his thumb and forefinger, and pushed his head back onto her nipple, drawing louder gasps from her with each flick of his tongue.

"Bite it," she seethed. "If you're gentle...you can bite it—AAAAOH!"

He was gentle; he pulled away with her pale cherry nub resting comfortably between his teeth, and it drove her crazy. He did it a few more times before repeating with the other nipple, leaving her a panting, sopping mess.

"Move your hands around!" The order came rougher than usual, but he followed it anyway, letting his hands roam down her sides and into her thighs, overloading her mind with multiple points of feedback. His thumbs traced her pelvic outline, his fingers crossed into her bush, then drifted downwards between her flooded lips.

"OH FUCK YEAH CALEB, feel how wet you make me!" In turn, she could feel how hard she made him; his turgid, burning flesh was pressed against her thigh. "Such a good fucking student!" she cried out, encouraging more strokes between her slippery lips, stoking her fire even further, bringing her so close to the edge but unable to bring herself over.

"Oh God, Caleb," she cried, "I need your mouth on me. I need your mouth on me right now!" He left her right breast, kissed the valley between her breasts, kissed below her breasts—

"Now's not the time for that shit!" In her pre-coital delirium, she shoved Caleb's head downwards until he was on his knees, facing her drenched, swollen center. For a split second she worried she had hurt or scared him, but his laughter put her at ease as his horizontal smile met her vertical one.

"GAH!" She threw her head back as Caleb's tongue pushed itself up her honeyed hole, opening herself up for an image to push itself into her mind: a queen, sitting upon her armchair throne, legs spread to be serviced by her young, loyal, muscular slave, on the promise of a special reward for a job well done. "You're so close," she moaned, pushing his head deeper into her center, her hips shuddering under the pressure, "so close, UUUUHHHHHHHHH lickmelickmelickmelickmelickmeeeeeeee!"

Her vision went dark and the sound dropped out until all she could register were her distant, muted roars and the head her hips twitched and ground against. The beige of her ceiling soon came into view, and she could feel and hear herself panting, then trembling, and then Caleb asking if she was okay, which became clearer after his head peered into view.

"Give me a minute," she said. "Try not to let this go to your head...but that was the second-biggest orgasm I've ever been given."

"It probably would go to my head if I wasn't wondering what the hell your biggest orgasm looked like."

Penny chuckled. "There was a guy I dated a couple of years ago. He had such a knack for oral I honestly wouldn't be surprised if he turned out to be an alien, or a ghost, or the ghost of an alien. Seriously, expecting any other lover to measure up to him would be borderline domestic abuse."

"C'mon, Miss Piper," he grinned, "you know I'm taking that as a challenge."

"Oh, I know, I'm just saying you don't have to. You're already a hell of a lot cuter than he was. In fact, why aren't you inside me?"

Before Caleb could say anything Penny pushed him down to the carpet with her foot, rose from her armchair, and sank back down over Caleb, straddling his pelvis. She straightened her back, showing Caleb the full majesty of the stacked body that would grant him his experience. Looking down, she drank in the strength, the potency, the nervous excitement of her conquest below, and she licked her lips and began to slip back and forth over his length.

"You ready to finally lose it?" she asked.

"Oh yeah."

"You suuuuuure?"

He vigorously nodded.

"You sure you want to give it to your hot, horny teacher?"

"FUCK, I'm sure!"

"You sure you don't want to save it for someone special?"

Caleb said nothing. Confusion and concern began to seep across his face. Thinking back to this moment, Penny had to marvel at how quickly she stopped grinding once she thought something was wrong. Given every intense fantasy she had about Caleb, she never thought she'd have this much self control, or for that matter, situational awareness.

"Caleb?" she asked. "Are you okay? Do you want me to stop?"

"NO! Nonononono!"

Thinking back to THIS moment, Penny had to laugh at how relieved she was to hear him say that. It was the next moment, however, that always made her cry a little.

"I just...you realize you're special to me, right?"

She blinked. "It was just a tease, Caleb," she said. "I didn't mean to make you uncomfortable, I'm sorry."

"No, it's okay, I get it, it's just...fuck, I don't wanna kill the mood."

She lowered her body to be closer to his, careful not to give the impression that she was calling this off on account of feelings.

"It's just...I never thought I had anything more to offer than being strong and sorta good at football. My teachers always wrote me off as a dumb jock, my friends are all kinda dumb jocks, and I just got used to the idea of being a dumb jock. Then you came along, and suddenly I get Shakespeare, and I'm a huge Pride and Prejudice fanboy, and there's this whole world I didn't think I was good enough for that's suddenly open to me because of you. I'm a better, happier person because of you. And you're kind of a good friend, too, almost as good as any of my teammates. And you're fucking sexy as hell. How could you not be special?"

Penny took his head in her hands, bent down, and kissed him passionately. What else could she do after hearing all that?

Aside, of course, from reaching behind her, taking Caleb in her hands, and guiding him into his very first sheath.

He moaned onto her tongue and into her mouth when he entered her, and she moaned in turn feeling his penetrating length bulge against her sensitive, slippery walls. She raised her head for a better view of Caleb's blissful, beautiful face and asked, "Does that feel good?"

"Fuck! You're so tight, Miss Piper!"

"Yeah," she said, "I think the mood is doing just fine, Caleb." She kissed him again, not yet moving, wanting to give him a chance to get used to her. "Just so you know, you're special to me too." She kissed him once more for effect. "Some people would say that I just made you a man, but you've always been more of a man than many of the men I've known in my life. You make me feel beautiful, and safe, and even if your lust for me fades, I know you'll always care in some way."

"Thanks, Miss Piper," he said. "I will."

"I'm sure." She pushed herself up, her hands pressed firmly upon his pecs. Her kind, honest eyes sharpened with lust and mischief. "Now, I don't mind being sentimental, but I've been wanting this thing for nine months, and now that I have it, it's killing me not to bounce on it. Are you ready?"

Caleb nodded. "Do it. Fuck me."

So that's what she did; slow at first, leaning over Caleb with her hands pinning his chest, locking her eyes on his face, watching it sigh and contort with each stroke. She offered her own moans to encourage him further, not that she was pretending to love his stiff cock plunging into her snug, sensitive depths. His tip kept poking at some nerve within that flooded her with heat and passion, encouraging her to speed up, bottoming herself out a little harder each time. She was bouncing hard enough, tilted down enough, that her glasses started to slip off her head, so Caleb reached up and pushed them back into place.

Penny giggled. "You like me with the glasses on?"

"You'd still be hot with the glasses off, but you drive me fucking crazy with the glasses on."

"So, you have a little nerd fetish, huh?"

"All the other football players shove them into lockers. You know how I like to be different."

"Mmm, maybe I should tell you about my Settlers of Catan strategy."

"Oh, you definitely should."

Penny stopped humping Caleb, holding all of him inside her. She began to lightly grind her hips back and forth. "Well, most players like to play the wood/brick game so they can go for Longest Road, but while they fight over that, they don't notice that I'm building up my ore, wheat, and sheep resources."

"Oh, you're bad." Caleb clearly had no idea what she was talking about.

"They're fucking around with roads," she said, dropping her voice to an aggressive whisper, undulating upon his prick, relishing the way it pushed into her walls, "meanwhile I'm building cities, bolstering my army."

"Yeah -- hrk! -- bolster that shit!" Caleb was close to breaking.

"And by the time they realize what's happening," she whispered in his ear, "it's too late." She pushed herself back up, pushed her chest out, threw her head back. "I've got MONOPOLIES!" she proclaimed, pumping down on him with each emphasized word. "They have to get their resources from ME! And nobody's gonna DARE rob me when I've got SO. MANY. UNTURNED. DEV CARDS at my disposal!"

It was all Caleb could stand with a straight face; he shattered into a laughing fit that quickly spread to Penny, who had to slow down to catch her breath.

She kept finding it interesting how Caleb had brought out her inner freak without really trying or even intending to. She wasn't even that much more experienced than he was, and yet with him, she had fashioned herself into some kind of dominating porn queen. She tied her best guess to her curiosity about erotic modeling so long ago; she passed it up partly because she didn't feel secure or desirable, but now that she did, she felt a sudden sense of freedom and a need to show herself off, a need which she now sated by leaning back to give Caleb a view of his youthful cock getting squeezed in and out of his teacher's pink slit.

"Aw, fuck!" he groaned, around the same time as Penny yelped "Shit yeah!" The change of angle was pumping Caleb closer to her g-spot; suddenly she was upping the pace, buzzing and sweating and pounding down on Caleb like she was hammering a stubborn nail, driving out of her a staccato aria of pleasure: "Ah ah ah ah ah ah ah!" She was getting closer and closer to the edge, and just needed one more different image to put her over.

"Oh shit, I think I'm gonna cum!" Caleb, unfortunately, was a different story.

Knowing she couldn't ask him to hold it without possibly slapping him, Penny hopped off. "Wait," she cried out, "not yet! Not yet! Uh, picture your mom naked!"

"WHY THE FUCK WOULD YOU SAY THAT NOW?"

"I DON'T KNOW, I'M SORRY, I PANICKED!"

On the bright side, it worked; Caleb's cock twitched, but nothing came out. He caught his breath, calmed down, and proceeded to ignore his place. "God dammit. I'm sorry, but you better have some nasty shit in mind to scrub that horror outtaaaaah myyy Gooooddd that'll do it."

He was looking at his once-softening cock disappearing into the valley between Miss Piper's tits, looking into her smug, playful eyes and naughty smile. He felt the soft flesh surrounding him, felt the beat of her heart through her chest. He thrusted upwards; there was a little too much friction for a good titfuck, but the brief glimpse of his head poking through her cleavage served him well.

Penny, for her part, never did anything like this before because she didn't see the point; that was obviously a mistake. It didn't hit any of her sensitive spots directly, but there was something empowering and nurturing about holding someone's throbbing manhood within the channel of her breasts. As usual, seeing Caleb react to it made it all the more erotic and fun. Part of her wished she could stroke him off like this -- perhaps with a little more lube -- but Caleb was just about ready to pop and there was something she absolutely had to try before that happened.

"How much can you carry?" she asked him, her breasts still wrapped around his cock.

"What do you mean?"

"First day of school, I had this fantasy of you fucking me while you carried me. You're standing, my legs are around your waist, my arms are around your neck."

"Oh, we're absolutely trying that. Stand up."

They stood. Caleb took a few seconds to size up Penny, looking a little unsure but no less determined. On his nod, Penny came in, kissed him, and wrapped her arms around his neck. Then, on the count of three, Penny jumped up, wrapping her legs around Caleb, which sent them tumbling backwards against the wall and forced Penny back on her feet.

They collided, grunted, and he laughed off the quasi-failure, but Penny shook her head and decided, "Shit, that's not gonna work."

"No, wait, maybe if I lift differently—"

"Caleb, I'm not gonna get much out of this if I'm worried that you'll throw your back out."

"What if I pinned you against the wall?"

"It would take the weight off you, but it would only be a little less uncomfortable, ALTHOUGH..." A sudden brainstorm renewed the light in her eyes, the plucky sidekick part of herself coming to the rescue. "Bedroom. Let's go."

* * * * *

Penny tended to write up packets and letters in the office nook within her living room, grade papers and pay bills in her kitchen. So she conceived the bedroom to be different from the rest of the apartment; a sort of sanctum within her home where she could escape to sleep or read or just be by herself for a little while. It occurred to Penny, as she approached the door, that Caleb was only going to be the third guy she ever bought inside, and for a fleeting moment she worried what that said about her feelings for him, and what those feelings said about herself. Then she remembered the necessity of bringing him in, and she was able to rationalize most of those fears away. (The more stubborn fears reminded her that she just used the word "rationalize," but in a few seconds she'd be too busy riding dick to pay them any mind.)

The bedroom was more classically furnished, opting for fine dark Victorian-style wood over the bright modern Swedish motif of the rest of the apartment. The centerpiece was a king-sized sleigh bed draped in a pillowy cream-colored duvet; Caleb was in visible awe. "This bed looks awesome," he exclaimed.

"Thanks," said Penny, "but I told you: we're not gonna make it to the bed." She directed him to a small walk-in closet, its sliding door already open. Near the top of its surprisingly deep frame, a pull-up bar was mounted.

Caleb snapped his fingers and pointed to the bar. "I think I know where you're going with this." He walked ahead of Penny and turned on the closet light.

Penny got that bar for days where she couldn't make it to her gym and promptly ignored it. Every day when she got dressed it would hang there, taunting her, reminding her of the forty bucks she could've spent on the Häagen-Dazs stand at the mall. After tonight, though, there wouldn't be any more regrets.

Penny walked up to Caleb and grasped the pull-up bar above her. She lifted herself with her biceps, just enough to bring her feet off the ground, and Caleb did the rest by supporting her ass and legs. When their crotches were level, Caleb guided himself back into Penny; she closed her eyes, relished the sensation of his entry, and let out a long moan in celebration.

Her eyes fluttered open, she ground on his cock, and she shouted, "Fuck me, Caleb!" And that's what he did, one hand on her back, the other on her hip, "Uh uh uh uh uh," plowing into her with sturdy legs and a relentless piston, nibbling on her outstretched tits, "Ah fuck yeah lick 'em Caleb lick 'em up," his hands moved through her hair, over her scalp, pulling her head back so he could lick up the sweat collecting on her neck and across her collarbone, "Aiiiieeee Goooooood fuuuhuhhhuhhhuhh FUCK!"

He was everywhere, consuming her, fucking her, straining the threads further and further and further, until they snapped and she screamed and she shouted gibberish between her cursing and her remarkable velvet box squeezed Caleb, drenching his feet and milking his perfect staff. He sealed his eyes and thought of Mrs. Warner telling him how to hold his pencil and somehow resisted the urge to flood her and create more problems, but then he felt the full weight of Miss Piper bear down on his hips and opened his eyes to find that she had lost her grip on the pull-up bar. Caleb quickly moved his hands to her back and caught her before she dropped to the ground, and for a few moments that felt like minutes she felt suspended in the air while she was cumming on this magical previously-unspoiled dick and she shouted again, prompting Caleb to pull out before she could tighten up, and he vowed to always carry condoms in his wallet from now on.

Caleb, barely able to catch his breath, guided Miss Piper to the plush carpet on the ground. Her arms splayed up and out in triumph, her disheveled hair fanned out around her head, her chest shined with sweat and heaved up and down, and her pussy glistened with the oils of her release. "You're no virgin," she panted. "I call such bullshit on you being a virgin. Virgins don't make women cum like I just fucking did."

"Well, I'm a quick study," he grinned.

"And you do have a great teacher, I guess," she grinned back, unable to move much more than that.

"Hey, Miss Piper, can I, uh... Look, I meant everything I said to you, but there's something I really want to do to you and I'm afraid you might—"

"Just say it, Caleb. You filled my fantasy, right?"

"Can I, uh...can I cum on you?"

Thanks to her lack of energy, it was easier than it normally would have been to suppress her relief and excitement. "Oh, is that your game?" she dreamily admonished. "You want to jack off onto me, mark me as your property? Make your prissy little nerd teacher filthy and unclean so she might know her place?"

"When you put it that way, it sounds—"

"Fucking hot," she finished. "Do it."

Caleb beamed, his cock twitched. "Okay! Stay just like that!" He waved a hand over her splayed, stretched, sweaty form. While his left hand held him up and over her body, his right hand guided himself back into her pussy. She was sore from the orgasms, a bit chafed from the rough-ish sex as well, but she didn't mind; after all he gave to her, she could bear it for five more minutes so he could have the finish he always dreamed of.