Under Supervision

"Are you serious, Mom? A babysitter?" "She's not a babysitter. Think of her as a nanny. Or a supervisor."

"I'm eighteen, Mom. I don't need supervision."

"Being eighteen is exactly the reason you need supervision. Especially since we'll be gone for a whole week. I know how boys your age think."

I stared up at her, trying to look as intimidating as possible. But given my short stature, I probably looked more like an annoyed rabbit than a ferocious lion. Curse my dad's short genes, constantly undermining me.

She paused to smile down at me, lugging a suitcase towards the car. "Look, Henry. It isn't because we don't trust you. It's because we worry about your safety. What if something happens while we're in Venice? We want to be sure you're okay at all times."

"I'll be fine," I muttered, taking the opposite end of the suitcase to help her. We tiptoed it to her trunk. "It's only a week."

"A week is a long time to worry about someone. Besides, this sitter– sorry, this supervisor– comes highly recommended by some friends. I'm sure you'll have a great time together."

"I bet," I said, noticing my dad trotting out the door, swinging his keys around his finger.

"Okay, that's everything," he said, flashing me a smile. "The sitter should be here any minute and we need to make that plane, so this is it." He gave me a pat on the back. "Take care of yourself while we're gone. You're the man of the house, got it?"

I nodded. "Got it."

"We love you, sweetie\!" my mom said as she ducked inside the car.

"Love you too."

She gave me a playful wave as they pulled out of the driveway, and then they were gone. I took a moment to absorb the silence, wondering about who this mysterious sitter was and why I even needed one. Tons of my friends stayed alone at home all the time. What made me any different? Just because I was short, shy, and meager didn't mean I was a danger to myself. With no girlfriend, hardly any real friends, and zero connections to booze or drugs, I wasn't exactly in a position to set the world on fire.

I wondered what my parents would do when I moved off to college in a few months, but those thoughts were interrupted by a loudening barrage of rap music. I could feel the bass shake the ground as it approached, disturbing the peace of everyone within earshot. I nearly had to cover my ears as the culprit appeared; a purple Cadillac SUV with chrome wheels and license plates that read "D1VA." To my shock, it pulled into my driveway, and I saw a pair of eyes twinkle at me through the tinted windshield.

The engine clicked off, killing the music and returning the neighborhood to its usual slumber, minus the chirping of birds who had long since flown away. I remained frozen, watching the car door open, gazing at a tall black woman stepping out. She flashed me a smile. Her energy was powerful. I wondered how she fit her curvaceous body into her tight clothes, looking like she might burst free of them at any second.

Despite my best efforts, I felt myself growing hard as she approached, her heels clicking against the asphalt, large breasts swinging back and forth.

"You must be Henry," she said, opening her arms to wrap me into a tight hug. With my face smothered in her cleavage, I found her sweet perfume was intoxicating. She gently rocked me from side to side, overpowering my small body. Any hope of not growing to full mast quickly vanished. "I'm Brianna," she said, letting go, allowing me to breathe again.

"You're my… supervisor?" I asked, choosing my words carefully.

Her thick ruby-colored lips curled upwards. "I am, but let's not call it that. 'Supervisor' sounds so… what's the word?"

"Demeaning?" I offered.

She let out a soft giggle. "Yeah. Demeaning. Let's just call me a friend, how about that?" But before I could answer she turned and made her way to the trunk of her SUV. I couldn't help admiring the way her ample ass bounced from side to side with each step. "You sure are cute. We're going to get to know each other very well for the next seven days." She gave me a wink as she lifted out a large pink duffle bag.

My mouth dropped and it took me a second to remember my manners. "D-Do you need any help?" I asked, stepping forward to grab smaller bags from her trunk.

"Well, yes, thank you." She patted the top of my head with her free hand, then bent down, squeezing my cheeks. "Aren't you the sweetest thing?" she cooed.

I felt like her pet, half-expecting her to feed me a treat. Normally, whenever people took advantage of my shortness, I quickly shooed them away. But when Brianna did it… it strangely excited me.

"My parents cleared a space for you in their bedroom," I muttered, color rushing to my cheeks.

"Well, lead the way, cutie." She closed her trunk with a smile.

I led her inside and up the stairs, still able to smell her perfume.

"Where would you like your bags?" I asked, lifting them as I entered my parent's bedroom.

"Anywhere is fine," she smiled, dropping her duffel bag onto the bed. "Truth be told, I had a long drive up here. How about I take a quick nap? Then we can lay down some ground rules while I make dinner."

"Sounds great," I said, my voice cracking. She gave me another wink. "There's a bathroom just across the hall if you need it." I stepped out of the room to give her some privacy.

"Thanks, sugar," she yawned. She unzipped her duffel bag, giving me a peek at some skimpy pajamas within. I imagined her wearing the soft fabric, resummoning my hard-on, leaving me wondering what was in store this week.

Two hours later, the sun was setting. I turned off my computer, my eyes tired from staring at the screen for so long. My stomach rumbled and I thought about finding some snacks but didn't want to offend Brianna by eating without her, especially since she offered to cook dinner.

My thoughts had been on her all evening. Where had my parents heard about her? Did she do this kind of thing often? What was it about her that made me so happy and obedient? I felt like an entirely different person near her. Would that fade away over the next few days, or would I be her puppy the entire week?

Tiptoeing to my parent's bedroom, I gently knocked, creeping the door open. Brianna was sleeping in bed, turned away with the covers pulled up to her neck. I watched her figure gently breathe, admiring the curves of her body. The way her waist curved up into that large ass was mesmerizing. I wanted to get closer to admire it. I wanted to touch her.

I quietly moved closer. Stop. This is a horrible idea. What are we doing?

I could have turned back. I could have stopped myself. This was the first night my supervisor was here, and I was already risking everything. The temptation fueled my desire, emboldening me, making me head-over-heels stupid. I crawled into bed beside her, slipping beneath the sheets to lay next to her.

Her breathing hadn't changed. She was still asleep.

I paused, breathing the moment in. Being this close to a beautiful, older woman was like electricity. Every nerve lit up, my heart racing. The world became hyper-realistic and the silence of the room was deafening. I took a slow breath before scooting closer, every tiny movement like a thunderstorm raging deep inside me.

I narrowed the gap between us, careful not to wake her. Draping a hand over her shoulder, I pressed my small frame against her. Warmth enveloped me. Despite being the big spoon, I was still comparatively tiny to her, like a baby koala on its mother's back. I pressed my cheek to her back, allowing the sounds of her deep breathing to lull me into a relaxed stupor.

Then she stifled, stretching out her legs and groaning. My eyes snapped wide, panic taking over. I desperately tried to think of an excuse about why I was cuddling with her… Part of me wanted to race out of the room… but it was too late. She was already turned around, looking down at me with those sparkling eyes.

"Well, hello there," she said, her lips parting into a smile. "What are you doing in here?" Her tone was playful. Soft. Teasing.

I got an eyeful of her revealing pajamas, all of her curves on display. Every inch of her dark skin was begging to be caressed.

"Oh. I was…" My mind went blank, letting the moment awkwardly hang between us.

When it became clear I wasn't going to finish my sentence, she smacked her lips together and nodded, giving me a teasing look that meant she knew all-too-well what I was doing. "Uh-huh," she said. "That's what I thought. Henry, have you ever been with a woman?" she asked.

I hesitated. "No."

"And you're going to college soon, right? You're eighteen?"

I nodded, feeling faint.

She smirked. "College is an interesting time, especially for cute boys like you. But only if you're ready for it." Her hand pushed between my legs, squeezing my maleness. "Oohhh," she cooed, eyes sparkling. My body stiffened in response. Her fingers danced across my bulge, squeezing it hard. "Not too shabby, kiddo."

"What's happening?" I asked, dumbfounded.

She pushed herself closer to me, her boobs bulging between us. "Don't be shy," she said, then leaned in close to whisper into my ear. "We could make each other feel so good for the next seven days. Would you like that?"

Her sweet perfume sent goosebumps up my arms. I shivered in anticipation. This was all happening so fast.

"Yes," I whispered back, nodding my head and looking up into those sparkling eyes, wanting nothing more than to feel her closer. I wanted to obey.

"Good boy." She smiled wide, then brought her lips to mine, moaning into me. Her plush lips tasted like strawberries. I kissed her back, holding her tighter, needing to deepen our passion. She was so large and comforting. My mind was exploding with lust.

Pulling down my pants, she cooed when my hard cock sprang up, slapping against her arm. "Oh, goodness," she whispered, scooting down, disappearing beneath the sheets. "We're going to be having a lot of fun this week. Look at the size of you."

Before I could respond, her lips wrapped around my thickness, bobbing up and down, slathering me in drool. My eyes rolled back and I reached for the headboard, not believing this was actually happening. Brianna's shape adjusted under the covers, climbing on top of me as she sucked away, the loud wet slurps echoing through the room. Her tongue felt magical, whipping across me, teasing me to within an inch of my life. She was a pro, gobbling down my excitement, sucking my balls, and bringing me to climax almost immediately. My body shook. I was rocketed to space, losing track of my body.

I was pumping my seed into her stomach as she moaned, giving me deep, long sucks, squeezing out every last drop. The world spun. A high-pitched ringing filled my ears as she came back up, popping her head out from underneath the covers with a sloppy smile. "Looks like we'll need to work on your stamina. Did it feel good though?"

I nodded, out of breath, ears still ringing.

"There's a lot more where that came from," she said, once again readjusting to be on top of me, straddling me above the covers. "But for now, how about you just relax while I show you a few things."

As she began to strip out of her pajamas, my eyes widened with excitement, admiring her naked form. She was the most beautiful thing I'd ever seen, with large dark nipples and a wobbling ass that widened past her shoulders. I was already hardening again as she tossed aside her clothes, utterly bare, ready for more passion.

She squeezed her large breasts together, making them look even plumper. "You like big tits?" she asked, mashing them tighter, gently bouncing them. Her flesh swayed like something out of a dream, making time slow down. "Because I can make them bigger if you want me to?"

"Bigger?" I asked. "How?"

She didn't answer. Instead, her smile widened as she closed her eyes and concentrated, arching her back and spreading her fingers far apart on her chest, pushing down the softness of her skin. Within moments, her breasts bulged further, pushing between the spaces of her splayed hands, forcing them farther apart. I thought it was some kind of trick, but the bigger she grew, the more undeniable her changes were, her boobs becoming disproportionately larger than the rest of her.

"How big would you like me?" she asked, still growing, each boob the size of a bowling ball and looking just as heavy. I couldn't help but imagine her leaning above me, swaying her shoulders from side to side to gently slap my face with her huge hanging beauties. So soft, huge, and inviting. My fingers desperately wanted to feel them for myself, but I reluctantly restrained myself.

"H-How big can you get?"

She leaned back, giggling. "A bit of a freak, huh?" Her smile widened. "I can dig that." She sucked in a breath and concentrated once again, cupping her boobs, letting them grow and fill up her hands, overfilling them to take up space between us. My cock throbbed, begging for attention as I marveled at the expanding goddess before me. Her tits were bloating outward like fleshy balloons, nearly twice their original size with no signs of slowing down. "Fuck, I feel so full," she moaned. "I can feel every inch of my skin stretching, getting tighter, getting bigger."

"I don't want you to be uncomfortable," I muttered, trying to stop myself from drooling.

"No\! It feels good\!" She smiled down at me, wobbling her boobs as they neared the size of beach balls. Put together, they were the same size as me, and I was desperate to smother myself between them. They were so huge and inviting, like nothing I'd ever seen before. With a heavy groan, Brianna leaned back further, letting her swelling boobs rest atop her, rising up higher and higher. One of her hands groped a thumb-like nipple, teasing and tugging it, making it harden further. "My body feels amazing. I'm more tits than woman now," she teased, shaking herself from side to side, careful not to lose her balance. "Are these big enough for you?"

"Not if you can grow bigger," I said, surprised by the intensity of my tone.

She hesitated, looking down at me. "Are you… are you sure?" she asked, looking surprised for the first time since I'd met her. "You want me to get even bigger than this?"

I nodded. "Yes. I want you to crush me."

A soft smirk spread across her face. "Wow. You really are a freak, aren't you?" She pinched herself harder. "This is going to be an interesting week for both of us," she cooed as her breasts pulsed and swelled, rounding out into perfect spheres, the pressure rising within. "Just be careful what you wish for."

She sucked in a breath between her teeth as her body went to work, developing more rapidly than before. Her boobs overfilled her arms, bursting through cup sizes at an alarming rate. In seconds, she made it impossible for either of us to move, her boobs weighing us both down like gigantic, seductive paperweights. She transformed into boulders of soft skin, wobbling back and forth, continuing to grow larger. Her breathing quickened and her eyelids fluttered as her tits grew bigger and bigger, pushing against the both of us, hogging up the bed and filling the room with their impressive size. The massive jugs bulged and pressed against each other, competing for space, jiggling from their own growth.

"Oohhh, the pressure\!" she gasped, her hands swirling around whatever soft skin she could grab. "I've never been this big before\!"

I watched hungrily, not wanting the surreal spectacle to end, but felt a rising concern. "Should we stop?" I asked her, noticing for the first time that my hips were moving on their own, gyrating against her from under the covers. I was already close to cumming for a second time as her gigantic couch-sized boobs flattened me to the bed, pleasurably pinning me down.

"No\! It's okay," she muttered, slowing down her breathing. "I can handle myself." She hesitated before continuing, "But I don't know how much more of this I can take. I feel ready to explode."

"Let's stop here then," I offered, most of my body swallowed up by her cavernous cleavage. Her immense warmth was making me sweat.

From over the fleshy sunrise of wobbling dark skin, Brianna stared down at me with pleading eyes. "I feel so full," she moaned. "You gotta help me." It was clear from her shoulder movements that her hands had traveled to between her legs, masturbating with throbbing need. "I feel like I'm going to pop, and… my boobs can only go back to normal if I orgasm first." She bit her lower lip, letting out an animalistic grunt. The wet sounds of her self-pleasure were undeniable. I felt the sheets dampen around me with her need. "Won't you do something? I know you're sorta stuck beneath these big dumb tits, but I can't cum without your help. Please. Pleasure me, kid."

With a twisted sense of dark pleasure, I realized I enjoyed seeing this woman beg for me. I had my supervisor by the balls– or rather boobs– able to make her squirm and writhe at my command. For the first time in my life, I was the one with the power. I had a sense of control. The little hero whose destiny it was to slay the imposing dragon.

"I'll help you on one condition." A wide smile spread across my lips. I reached out to grab her fist-sized nipples, giving them a squeeze.

She moaned in response. "Yes, anything."

"You have to promise to grow bigger every day this week."

She stared down at me in disbelief. "Are you serious?"

"By day seven I want you to fill the entire house. Got it?"

She looked unsure, but the familiar twinkle in her eyes along with a creeping smile gave away her hidden excitement. "Oh, you're bad, aren't you? You're gonna have me on a leash."

I nodded.

The thought made me smile as I went to town on her nipples, pushing my cock bulge against her wet pussy from below, ready to deliver the first of countless orgasms. She moaned, making my heart soar. I wanted nothing more than the two of us to melt together, and for her to grow bigger, and bigger, and bigger.

It seemed inevitable we were going to ruin each other for the next seven days.