[MF] Putting a stuck-up little rich girl in her place.

“Be quiet,” Olivia grunted, struggling against her restraints, her eighteen-year-old ass wiggling deliciously before me. “Or my dad will hear.”

I grabbed her hard by her dirty blonde hair, forcing her head back, arching her back. In the mirror across the room, I saw a look of pained ecstasy on her young face as her pert tits thrust forward. I slid a hand between her ass cheeks, my fingers covered in lube, as I teased her open. She bit her lip.

“You don’t tell me what to do anymore,” I growled in her ear. “You keep your mouth shut, or I’ll shut it for you.”

She nodded hurriedly, her mouth opening in a wide, silent moan of pain and pleasure as I began to slide into her ass.

“Yes, Sir…” she whispered, barely audible. The New York City skyline glittered in the distance from her bedroom window as I embedded myself up to the hilt in her tightness. A single tear slid out of the corner of her eye, running over her Tiffany necklace—the only thing she wore—before dissipating on the pink tip of her flushed breast.

Let me back up a little bit. How did I end up sodomizing a veritable Manhattan princess, tied up, in her palatial Tribeca bedroom?

I suppose the beginning would have been right after I graduated from college. At twenty-two, despite having something dangerously close to a 4.0 GPA from a certain well-renowned university on the outskirts of Boston, I had no real ambitions of note, and few interests beyond reading and getting high. I had identified in myself, late in high school via widely available internet pornography, certain sadistic tendencies, which I had channeled into a significant though relatively secret interest in BDSM, unknown to nearly all of my acquaintances, with the except of a handful of sexual partners who, fortunately, had masochistic themselves tendencies to vary degrees. I was never exactly an Adonis, but I had an unkempt hipster boy thing going in high school and college that some girls seemed to appreciate.

As a borderline sadist, I naturally gravitated towards a career where I could cause the most suffering: an officer in my alma mater’s office of admissions. For two years, I flew across the country, implying to hundreds, nay, thousands of hopeful students and their families that yes, they were good enough, smart enough, interesting enough to join the elect on the shores of the Charles. And then, each autumn, I returned to help reject virtually all of them.

While my position allowed me to satisfy my latent sadism, I quickly became disenchanted with the long hours and constant travel. So, after two years, I did what seemed both natural and profitable: I moved to Brooklyn, and began to consult independently on the college applications of New York’s most spoiled children, charging two-hundred dollars an hour.

One of my first clients was the managing partner of an enormous midtown law firm—or, more accurately, his daughter, Olivia. I first met the two of them shortly after Olivia’s eighteenth birthday, the summer before her senior year. She had just come home from field hockey camp, still wearing a tight, turquoise tank top and athletic tights, her blonde hair done up in a pony tail and her ice blue eyes glowering at me.

“My god, I still can’t believe what a deal you’re giving us,” her father was going on. I had told him, initially, that two-fifty was my hourly rate but that since they were near one of my other clients, I’d give them a discount, since the travel would be easier for me. That made the two-hundred price point far more palatable.

“I’m the one missing out on my summer, daddy,” Olivia grumbled, but her father ignored her. I got the sense this happened a lot.

I sat down with Olivia on the terrace of their apartment, overlooking Central Park. I had learned to mask my amazement at the lifestyles of the rich and famous with indifference during college, but I still found my gaze distracted from the transcript in front of me by two beautiful sights: the park, on one hand, and Olivia’s pert chest on the other.

“Stop staring at me, perv,” she whispered, whipping her hair back. But she was smiling.

“I’m not staring at you,” I shot back. “I’m wondering how I’m going to get you into college with grades like these.”

“Oh, fuck you,” she scowled. “I hate school.”

“I can tell.”

She gave me a playful punch.

“My dad is paying you way too much money to get me into college. So it’s your problem now.”

Now it was my turn to scowl. She was right.

We drew up a list of schools she’d apply to, including my and her father’s alma mater, though I doubted she would get in. When I suggested NYU, she shook her head.

“Daddy won’t let me apply there.”

“Why not? It’s a better fit for you than H—“

“Because my ex goes there. And no one liked him.”

“It’s a big school. You’d never see him.”

“You don’t understand,” she scowled. “See… We did things pretty rough. And I’d have bruises. I liked them. But everyone got the wrong idea.”

She pulled down the side of her tights, showing me just enough delicately tanned ass flesh to harden my cock involuntarily.

“Mostly down here… But he’d choke me too.”

She placed her hand on her neck and mimed being choked, her mouth open, her eyes trembling and looking deep into mine, a look of fear and hopeless submission suddenly coming over her.

And then, in a moment, it was gone. She laughed, as if it hadn’t happened—as if she hadn’t transformed into my fantasy right then and there.

“And we got in trouble and they made us break up. The end.”

We worked for the rest of the hour without further incident, but I couldn’t help but think that Olivia had noticed a change in my own eyes—one of hunger and desire.

Over the next few weeks, Olivia would make occasional comments like that and even wilder—that she was bored and horny, that she hadn’t gotten fucked since coming home from field hockey camp, that she would masturbate while reading Fifty Shades of Gray, which, as far as I could tell, was the only book she read that summer. I’d do my best to ignore her remarks, but I’d often find myself with my cock throbbing by the time I left.

One afternoon, when I came over, I found Olivia and her best friend, Maisie, sweaty and enjoying smoothies in the kitchen after a workout.

“Is that him?” Maisie asked, looking me over as I stepped into the apartment. They both looked up from their phones.

“Oh, fuck you,” Olivia scowled as Maisie giggled.

“She has a crush on you. She wants to fuck you. She thinks you’d tie her up. She looked at your internet history.”

I would, in fact. Gladly. Olivia looked at Maisie with her mouth open.

“Oh, fuck off!” she scowled. “I’m taking a shower. You can let yourself out, cunt.”

Maisie burst out giggling as her friend stormed out of the room. Normally, if I had seen such an exchange between friends, I’d have been concerned. But the two of them seemed to strive to push each other’s buttons. This was a victory for Maisie, but Olivia would always manage to enrage her back by the end of the week.

Maisie gathered her things and started to leave, before shooting me a glance.

“You can make a move on her, you know. She wants it.”

“I work for her dad,” I said with a shrug. “I’ve got a business here. Sort of.”

“Oh, do you seriously think Olivia will say anything? Her dad works like crazy long hours. And her mom is never home. She’s alone a lot.”

I glanced down the hall, where Olivia had disappeared off to. Maisie left and I, too, was alone in the kitchen.

~

I waited for Olivia in her room. It was like any teenage girl’s room, but… nicer. Looking out over a stretch of city, I could see the bustle of the street below and the river glinting between buildings.

After twenty minutes or so, I heard footsteps. The door opened and there was Olivia, wrapped in a towel, her hair still wet.

“We don’t usually have our sessions in here,” she sputtered. A flush spread on her cheeks.

“I know.”

“So what are you doing here?”

I began to undo my belt.

“Waiting for you.”

She bit her lip, a smile playing on her face.

“Is this because of what Maisie said? She’s just making trouble.”

“Then kick me out of your room.”

She made no moves towards the door, or towards me. We eyed each other for about ten minutes before she undid her towel and let it fall to the floor, revealing her tight, toned body, glistening with water and a slight tan, her light pink nipples hard on her full, pert young tits. Her hips widened deliciously, with a thin line of hair leading my eyes down to her pink pussy lips, peaking out at me from between her thighs.

“Well?”

I finished undoing my belt and slid it off.

“You liked ‘Fifty Shades,’ didn’t you?”

I saw her eyes widen.

“Yeah…”

“I bet you want to try some of that.”

“Maybe.”

“Is that a yes or a no?”

“It’s a yes.”

“On your knees.”

As if in a dream, she knelt before me. I took her head in my hands, her eyes looking up at me wide.

“Oh, don’t look so scared. You’ve done this before.”

Her pretty face broke into a smile.

“I know. But I like how you’re taking charge.”

“Olivia,” I said softly, running my hand along her cheek.

“Yeah?”

“You’re talking too much.” Now, my cock was in my hand and she giggled.

“God, I’ve wanted to suck you off for weeks…”

She placed a soft kiss on the tip of my cock, her lips wet and warm and soft. She began to lap at the head of my cock, running her tongue occasionally down to the shaft before returning to the head, taking just the first inch into her mouth.

“I’m going to be rough with you now,” I murmured. “If I do something you don’t like and you want me to stop, say ‘Red.’ If you want me to slow down, say ‘Yellow.’ And I might ask you if we’re ‘Green’—does that make sense?”

She nodded eagerly, stroking my shaft.

“And if you can’t talk—make eye contact and shake your head fast, and I’ll stop. Do you understand?”

“Mhm.”

I ran my hand through her hair and gripped it suddenly. She gasped.

“Oh, fuck, I love that.”

I pulled her hair back, forcing her to arch her neck as I slid a hand up to her throat, gripping hard. Her eyes widened, as they had done on that day when we first met.

“You like that,” I growled. She nodded, reaching up to hold my wrist but not trying to stop me. I pressed my lips to hers, feeling her body tremble and swell. I only gripped harder, feeling her pulse pound in her neck. Finally, I let her go and she gasped hard.

“Fuck! Fuck, fuck, fuck, I needed that. That was awesome.”

Tears were sliding down her cheeks now but she was all smiles.

“Good girl. Green?”

“Green. Can I…”

She paused. And stopped.

“Yeah?”

“Can I call you ‘Sir’? Or something like that? I just think that’s like so hot…”

“That’s exactly what you’re going to call me,” I replied.

“Thank you… Sir.”

I pressed my cock now against her lips and she obediently opened her mouth, allowing me to slide in. I held her by her hair, forcing myself slowly down her throat. She began to gag, and choke, and grunt onto my cock as her gag reflex struggled to force me out. She dug her fingers into my thighs, whimpering pathetically as I slid myself back out before plunging back into her throat.

I began to fuck her face, faster and harder with each moment as she gagged hard. She dropped a hand down between her thighs and began to touch herself, groaning onto my cock as I destroyed her teenage throat, forcing her face into my pubic hair and holding it there while she whimpered.

Finally, I groaned and released myself into her, my orgasm overtaking me and filling me, before pouring out of the tip of my cock and down Olivia’s throat. We locked eyes as I came, and she gulped the long, hot, sticky ropes of my cum down like a professional.

I slid myself out of her mouth and she sat back, gasping, my seed dribbling out of her swollen lips.

“Fuck. I haven’t gotten face fucked like that since my ex…”

“I didn’t say you could touch yourself, Olivia,” I growled, ignoring her comment.

“What?”

I plucked up the belt.

“That’s ‘What, sir?’”

She bit her lip.

“I’m sorry, sir. Please… Forgive me. Sir.”

“Bend over the bed.”

“Yes, sir. Please, go easy on me, sir.”

“No.”

She gasped as I touched my belt to her generous ass.

“Thank you, sir. I don’t deserve to have you go easy on me, do I, sir?”

“You’ve been kind of a shit student, Olivia. To be totally honest.”

“Yes, sir.”

“You don’t try hard.”

“No, sir.”

“But we’re going to start changing that, aren’t we, Olivia?”

I raised my arm and brought the belt down—hard, but not that hard. She jumped.

“Yes, sir.”

“How many blows do you think you deserve, Olivia?”

She paused.

“Uh…”

I slapped her other cheek. She gasped.

“I’m waiting, Olivia.”

“Twenty, sir?”

“Twenty-five, is that what I heard?”

“Yes. Yes, sir.”

“You’ve had two. Count for me.”

And count she did. I didn’t strike her particularly hard—she was still new at this and I wasn’t sure how much she’d be able to take. Nonetheless, I carefully increased the strength of the blows as I flogged her, her cries like sweet music as I beat her. She had gorgeous pink welts rising on her plump, perfect ass by the time I was done.

“Thank you, sir,” she whimpered, as I grabbed her by the hair, and forced her to flip over, spreading her legs for me in the process. She was absolutely soaked, her pink hole sopping wet and spreading for me practically of its own accord.

“Ow,” she whimpered.

“What’s wrong?”

“My ass. It’s just sore. On the bedspread. It’s fine. Sir.”

“I know it’s fine,” I shot back, taking one of her tits in my hand as I leaned down to kiss her. I groped and twisted her nipples hard, as if showing no consideration for her pleasure—but judging from her moans and gasps, she loved it, and this only made me rougher as I forced her back onto the bed, spreading her legs once more.

I buried my face in her snatch, slurping at her perfect teenage cunt, tasting her delicious juices and inhaling her scent. She writhed for me, shuddering and trembling as I ran my tongue from the bottom of her slit up to her clit. Normally, I try to go more slowly with these things and tease, but I needed to taste Olivia and, frankly, she wasn’t complaining.

“Sir… Sir, maybe I touch you?” she moaned, pressing her hips into my mouth.

“You may.”

Her hands were immediately on my hand, gripping me hard as I slurped at her.

“Oh, fuck, sir, fuck… Sir, I have another request… It’s embarrassing…”

“Tell me, Olivia,” I order, glancing up from her oozing pink lips, her hole trembling and spasming.

“I… Don’t tell Maisie, sir, but I like it if you touch my ass while you lick me. I mean, my asshole. Sir.”

I chuckled and ran a finger over her slit, collecting her juices on the tip, before pressing into her pink, puckered little asshole.

“Like this?”

She gasped.

“Yes, sir.”

I pressed in deeper and felt her muscles grip my finger hard. I fucked my finger in and out of her for a second and she shuddered, before her muscles finally gave up and let me drive my finger up to the hilt, into her ass.

“How’s that?”

“Perfect, sir.”

“You like it in the ass, don’t you?”

“Yes, sir.”

“Your ex fucked you in the ass.”

“Yes, sir.”

“And now your ass is mine.”

She gasped as I pushed a second finger into her ass and then a third. Her greedy asshole made a show of trying to keep me out before sucking my digits in deep as I returned to licking her. With the addition of my fingers, she seemed to get even wetter and it only took a minute of lapping at her clit to bring her to a writhing, bed-gripping orgasm.

“Sir…” she murmured as I stood up, wiped my mouth with the back of my hand, and took hold of my hardening cock once more. “Check the top drawer of my night stand.”

I did and, lo and behold, a small treasure trove of sex toys were revealed to me. I plucked a pair of handcuffs from among them (along with a small bottle of lubricant which I pocketed for the right moment) and, rejoining her on the bed, cuffed her hands together. She grinned at me, dried tears on her flushed cheeks.

“You’re so kinky, sir… Fuck…”

Then, using my belt, I tied her left leg to one of the posts of her bed. It wasn’t exactly symmetrical or clean, but between the handcuffs and the belt, she was pretty well restrained and I could easily maneuver her at my pleasure.

Now, I mounted her from behind, sliding my throbbing cock into her. I grabbed her hair hard, her hot pussy engulfing my engorged member.

“Yes, sir!” she moaned.

“I noticed you’re on the patch,” I growled in her ear.

She nodded enthusiastically.

“Please, sir, cum in me…”

“I haven’t decided where I’m going to cum today. But for the future.”

She moaned as I doubled down on her, pounding her harder and harder. A few times, I felt myself get close but I managed to distract myself, sliding my cock out of her and thinking about baseball statistics—an old but effective trick. At one point, we heard the door to the apartment open and close. Footsteps.

“Who’s that?” I grunted softly.

“My dad. Sometimes he comes home in the middle of the day to change.”

She called out, her voice surprisingly clear and free of lust—no indication that she had me balls deep inside of her.

“Daddy, is that you?”

“It is, sweetie—are you in your room?” Footsteps neared the door.

“Oh, don’t come in, daddy, I’m getting changed!”

“Right, honey—I’ve got to run back to the office. Spilled some curry on my tie. See you tonight.”

And then, he was gone. My cock was still hard. I began to ride her again, keeping my grunts quieter now.

Finally, though, I knew I wouldn’t be able to hold on much longer. I clicked open the little bottle of lubricant.

“Olivia, I’m going to fuck your ass. Do you have a problem with that?”

“I love being fucked in the ass, sir.”

“Beg for it.”

She looked back at me, her eyes shining with lust.

“Please… Please, sir. Fuck my ass.”

As I began to pound her, she moaned and whined and begged, just as I imagined she would, arching her back, her muscles gripping my cock hard as she milked me. As I drove into her, her ass stretched hard around my cock, letting me embed myself fully inside of her, the tip of my cock plunging into her depths, into her hot core. I felt her tremble and gasp, whispering the word “Sir” over and over again, a furious, fevered chant.

Finally, I unloaded in her. She whimpered pathetically as my cock spasmed in her, filling her ass. As I slid myself out, I allowed her to collapse on the bed. I lay next to her, stroking her hair, running my fingers delicately over her bewitching face.

“That was fucking insane,” Olivia sighed, pressing against me. Her thighs were streaked with my leaking cum, but since didn’t seem concerned. “You’ll be in so much trouble if I ever tell daddy.”

“But you won’t,” I said, firmly. She gave me a sly look.

“Then get me into college,” she replied almost immediately. “I promise I’ll work harder.”

Source: reddit.com/r/gonewildstories/comments/o9ovwk/mf_putting_a_stuckup_little_rich_girl_in_her_place