Olivia’s Hypnotic Confession Ch. 05

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I’m certain you’ll forgive me for not really mentioning my other step brothers until now. If you’ve been reading these, you’ll know that Caleb had been keeping me occupied…so to speak.

Michael was the middle brother, twenty four years old, and an aspiring Gordon Gekko type. He had stick-thin arms and legs standing in contrast with a pot belly, a kind of skinny-fat that almost excused his baseline hostility. Michael just barely masked his contempt for me, never failing to go on some Ayn Randian rant about how poor people—like me, I presumed—drained the resources from successful families.

But I was rarely Michael’s target, mostly because he hated Caleb more. Michael, being the ultra-capitalist of the family, couldn’t stand that Caleb was not only their father’s consigliere, but also really good at it

That was why Michael hadn’t been around much lately. For the last two months, he’d been interning at an investment firm in New York City, trying to get enough real world experience to match Caleb’s business acumen. (Caleb never went to college or cut his teeth as an intern. Business just came naturally to him, which only fueled Michael’s anger.)

Then there was Kevin, the youngest. When I first moved out here, I pegged him as a potential buddy. I could still remember when I got off the plane with Mom and saw Frank and his boys there, waiting for us.

Kevin looked like a mouse, with his nose jammed in a copy of On the Road. His sweatshirt caught my eye, a muted blue hoodie with a strange decal: the upturned body of a dead bird. He was seventeen with a faintly cherubic baby face, as if he’d been slightly overweight at one time. He was in good shape now—he was on the track team, I’d later find out—though his matted black hair and wireframe glasses made him look more like an aspiring librarian.

We left the airport in a limousine, where I ended up sitting next to Kevin. He kept squirming away from me, like he was afraid we might touch.

Mom was jabbering on about something. She was gabby when she drank, and she’d killed a bottle of wine during the flight.

Kevin had his nose in the book again.

Finally, it occurred to me. “Harper Lee,” I said.

He jumped a little. “I’m sorry?”

“Your hoodie,” I said. “That’s a dead mockingbird.”

He laughed nervously. “Oh, yeah. Love that book.”

I nodded to the book in his hands. “Kerouac’s okay, I guess.”

Kevin shrugged. “Yeah, a little.”

“Kind of a pretentious proto-hipster.”

“Yes!” he said. He straightened up in his seat, suddenly engaged, smiling, but then our legs touched and his face turned red.

“Kevin!” Michael barked. “Close that book and listen to your future step mother. You’re being rude.”

“Sorry,” he said, and that killed our conversation.

Hours later, after settling into my new bedroom, I found my copy of Post Office by Bukowski and headed to Kevin’s room. I thought he might enjoy it.

Kevin wasn’t there, but I was shocked at the shelves of books in his room. His collection ran the gamut from the greats to modern penny dreadfuls; the requisite heavyweights, like Hemingway and Fitzgerald, to small-press lit mags and fringe poetry.

But what truly drew me in was the heavy antique typewriter set up in the corner. It was heavy, refurbished, and in working condition. A blank page sat in the carriage, with a pile of typed pages right next to it. I looked over his work.

The kid was a poet too!

It was a free-verse poem, divided into six four-line stanzas. I began reading it aloud, softly. “That fleeting touch proved to be my winter’s bane,” I read. “Candlelight, dying, but blazed the frost from—”

“What are you doing in here?” Kevin said from the doorway.

I held up the page. “Dude, you’re fucking good.”

He tore the page from my hand. “Please don’t read that,” he said, his face blistering red.

I put my hands up in apology. “Hey, sorry. I didn’t mean to intrude.”

He wouldn’t look me in the eye. “Well you are.”

“Okay, so I have this book you might like, especially if you think Kerouac was kind of a pussy.”

He took the book and tossed it on the bed then led me to the door. “Yes fine Olivia thank you.”

“Alright,” I said as I stepped into the hallway. “Let me know how you like it.”

He slammed the door in my face.

I nodded and raised my middle finger. “Right back at ya, asshole.”

In the following month, Kevin and I barely spoke, unless it was polite conversation in front of Mom or Frank and, even then, it was like pulling teeth to get a word out of the kid.

Soon after, Kevin went to live with his mother for a while. Good riddance kiddo, I thought. No hair off my ass.

So imagine my excitement when I heard about Kevin’s eighteenth birthday extravaganza. Birthdays, I came to discover, were a big deal for Frank Montgomery.

Caleb visited me at 18 Straight to break the bad news. He walked in while I was thumbing through a chapbook behind the register, sighed, and lay his forehead down on the counter.

“What’s ataşehir escort wrong, Richy Rich?” I asked him.

“It’s Kevin’s birthday this weekend.”


“You haven’t experienced birthdays in my family yet,” Caleb said, a look of distant sadness in his eyes. “Eighteenth birthdays are especially awful.”

“It can’t be that bad,” I said.

“It will be extremely…Irish.”

“That sounds fun. I grew up in an Irish family,” I said.

“Olivia, you don’t understand,” Caleb answered. “My father had a rough upbringing and his family never had proper birthdays.”

The horrifying prospect of it hit me. A man suffered a deprived childhood and now had the means to overcompensate for what he lacked as a boy.

“Oh no,” I said.

“We’ll need to look out for each other during this shit show,” he said. “If it gets too bad, you’ll be my excuse for leaving. Like, you say you have a stomach bug and need a ride home.”

“And vice versa?” I asked.


I always was in favor of having an escape route for awkward gatherings, but something didn’t feel right. “Wait, couldn’t you do all this with Cortney?”

“I’d never subject her to a Montgomery eighteenth birthday party. It’s too long, too insufferable, and has too many shamrocks.”

“But you have no problem subjecting me to it.”

“That’s different. You’re one of us now.”

Damn it, he was right. “Deal,” I said.

Caleb extended his pinky. “Swear it.”

And thus we pinky swore, so solemnly that it might as well have been a blood oath. Caleb may be overreacting, I thought.


He wasn’t.

Frank rented out a country club for the occasion, complete with free rounds of golf for every Montgomery that showed up, with red-haired Irish girls dressed in skimpy leprechaun outfits serving beer and Irish potatoes along the way.

I was no snob, far from it, but I immediately saw Frank’s wealthy guise melt away as his brothers, sisters, cousins, and more streamed through the wrought iron gates. While I’d known Frank as a buttoned-down money man who only associated with similar types, this wave of South Bostonians brought out Frank’s inner Beantown Mick.

I saw Kevin briefly. He already looked hammered as they paraded him around the club grounds in a golf cart adorned with shamrocks, trailed by another cart carrying a three-piece bagpipe band.

“I thought you might have been exaggerating,” I admitted to Caleb.

“The only way to understand is to bear witness for yourself,” he said.

At least we looked good, Caleb especially. He wore a gray suit with a blood-red shirt, an ensemble that probably costed more than my first car. I wasn’t so bad myself; a simple black dress, PG-13 length, ending a few inches above my knees, along with a pair of heels Frank bought me, made from some Parisian designer whose name I couldn’t pronounce.

We shoved into the bar for a drink. The bar was already packed, but there was a brief moment of quiet when we approached the bartender.

The bartender was already overworked, quietly ashamed of his own leprechaun outfit, mostly by the fake red beard. “Top o’ the morning to ye!” he said, as if each word were chipping away at his soul.

Caleb pushed two hundred-dollar bills across the bar. “Timmy, you don’t have to, not with us.”

Timmy pocketed the money. “Oh thank Christ. Cal, I dunno if I can do it…”

“Neither do I,” Caleb said.

Timmy whipped up two whiskeys on the rocks. “Here ya go.”

“Good luck man,” Caleb said.

A drunken Montgomery man stumbled up to the bar. Timmy winced and said, “Top o’ the morning, lad!”


As the party moved into the great hall for dinner, I was overtaken by the stench of authentic Irish cuisine. Ham and cabbage, Shepherd’s Pie, bangers and mash, and the ever-present coconut monstrosity of Irish potatoes. For all the adventurous culinary exploits, I couldn’t find a French fry to save my life.

The clocks chimed and signaled yet another hour upon us. Caleb went back to the bar for drinks and, I prayed, a couple packets of crackers to munch on. Up on the stage, Frank had stuffed Kevin into a chair to put him on full display, perhaps so everyone could see how goddamn drunk the kid had gotten.

Frank was shitfaced by now too, microphone in hand, and prepared to give his fourth heartfelt speech of the night.

With a sudden, drunken outbreak of Riverdance on the dancefloor, I barely noticed when Michael sat down next to me.

He had a glass of red wine and a half-eaten Shepherd’s Pie. There was a glob of gravy on his chin. He smiled. “Olivia,” he said.

“Mike,” I said, then looked around for Caleb. I needed that goddamn drink.

“Looking for my brother?” he asked as he shoveled the slop into his mouth.

“He’s getting us drinks.”

Michael wiped the goo from his lips and slurped down his wine. “I’ve noticed that Caleb has been helping you settle in.”

That last comment came out with a particularly slimy kadıköy escort intonation. I studied Michael’s crooked grin. No, I thought. He doesn’t know anything. Impossible.

“He tells me you’ve been working in a bookstore,” he said. He laughed at that.

“You find that funny?” I asked.

“Not at all.” He raised the remnants of his glass. “A toast to your self-reliance. I didn’t know you had it in you.”

I ignored his aside. “I just like poetry, dude.”

“I’ve heard that you consider yourself a literary gal,” Michael went on. “Kevin tells me you’re a Bukowski fan. You know, I minored in literary theory. We could chat about Bukowski’s socioeconomic influences sometime. That is, if you can manage to discuss it properly.”

I glared at him.

“Apologies,” he said. “I misspoke.”

“No worries,” I said, and shoved the Shepherd’s Pie onto his lap.

“Cunt,” he said, simmering.

“We can go out back and talk all the fucking literary theory that you want,” I said. “Just try me.”

He stuttered for a reply, couldn’t manage to think of one, then got up in a huff and disappeared into the crowd.

I clenched my fists, enjoying the rush, half-convinced that I should whup Michael’s ass right in front of his family. The adrenaline coursed through me, almost electric, until something else stirred. It immediately caught my attention.

I wasn’t wet. Not yet, anyway. But I was primed and ready. It was the first time I’d gotten turned on without my hypnosis since that party after high school, during that night that ruined my reputation.

“He’s an ass,” someone said behind me.

Kevin stood there, and I say ‘stood’ in the loosest sense of the term. He swayed back and forth. I smelled Guinness on his breath.

“Looks like you’re having a happy birthday,” I said to him as I looked frantically around for Caleb again. What the hell was taking him so long?

Now up close, I saw that puberty had hit Kevin in a big way. He was still a head shorter than Caleb, but he was bulkier now. Kevin must have been skipping the track for the weight room.

His baby face was gone, replaced by cheekbones reminiscent of Caleb’s, along with a dark five o’clock shadow.

“Thanks for coming,” Kevin said. He fell into the chair next to mine. “Mind if I sit?”

“I’m going to be honest. The last time we saw each other, you wanted nothing to do with me.”

“No that’s not it I swear.”

“I don’t want any ‘warm’ family moments just because you’re wasted.”

He took my hand, looked at me with dire seriousness. “Olivia, I’m in love with you.”

“Sure you are,” I said.

“Michael told me not to talk to you,” Kevin continued. “He made me think you and your mom were just after our money.”

“My mom is after your money,” I said. “But that doesn’t mean I am, too.”

“I know that now. I’m sorry,” he burped, long and loud. “And I love you.”


“Lemme prove it,” he said, and leaned in, lips puckered.

I palmed his face. “Oh buddy, no.” No one saw the debacle. Luckily, the Riverdance fever had caught on strong. Even Mom was up on stage.

“You don’t think I’m a man,” Kevin said, near tears now.

I grabbed him by the collar. “Kevin, this is what you need to do. Go outside and ask for a car back to your dad’s house. Drink a bottle of water, take an aspirin, then lay down and jerk off.”

He was confused. “But…”

“You can even think of me while you do it,” I said. “But just this one time. Then in the morning we’ll pretend like this didn’t happen.”

Kevin frowned. “Can we talk about Bukowski in the morning?”

“We sure can, champ,” I said. I pushed him out of the chair, toward the exit. “Now run along.”

I hurried out of the hall, my nerves tingling, my body eager and willing. I still wasn’t wet, but I remained horny as hell. It had been so long since I felt it without being in my trance, I was afraid it might vanish if I wasted anymore time.

I found Caleb at the bar. An overly tanned, wrinkled middle-aged woman pinned him against the bar, her martini sloshing over her glass, as she begged him for a kiss. Caleb recoiled from her lips as politely as he could.

I squeezed between them and grabbed Caleb by his suit jacket. “I’m sick,” I said. “Walk me to the bathroom.”

“Who might this be?” the woman asked with a pack-a-day voice.

“Olivia,” Caleb said. “I’d like for you to meet my Aunt Karen.”

“Aunt by marriage,” Karen corrected him.

Caleb grabbed our drinks and we escaped. I pushed him into a dark corner. “Hypnotize me,” I said. I didn’t need to elaborate; he saw the hunger in my eyes.

He sipped his whiskey and shot me a playful smile. “We’ll head back to my loft.”

“There’s no time for that. Can you find a quiet spot here?”

He unclasped my talisman from his neck. “When there’s a will, there’s a way.”


He led through the deserted locker room, through the showers, all the way back to a small massage room. It had two massage tables and smelled bostancı escort of incense.

Caleb picked up one of the unlit candles scattered around the room. “Should I light one to set the mood?”

Now in my trance, I was relaxed, wet, and eager. “I’m already in the mood, now fuck me.”

He grabbed me by the throat. “You’ve got quite the mouth.”

“Why don’t you shut me up then?”

He removed his belt. “Take off your heels and your panties then lay flat on your belly.”

I took my heels off first. Next, I pulled my dress down over my chest then—

His belt cracked across my ass.

“I said your panties, not your dress. Understand?”

“I understand,” I said.

He cracked me again. “Don’t talk unless I specifically give you permission.”

There was a mirror across the room. When I saw the bright red welts across my ass, my pussy grew wetter. I spread out on the table, per his instructions.

He reached into his suit jacket and pulled out the same red silk scarves he used when he fucked me in the fitting room.

I trembled in anticipation. Knowing that he came here prepared excited me even further.

“I’m missing something,” he said to himself. He left the room for a moment then returned with a nine iron golf club. “That’ll do just fine.”

Caleb hoisted me onto my knees, ass up, face flat on the table. He situated the nine iron horizontally between my legs, resting an end on each of my ankles.

He bound my ankles to the club with the scarves. For good measure, he gave my ass another crack with his belt. He then pulled my arms between my legs and tied my wrists to the nine iron.

That sense of captivity left me eager for his next move.

He brushed my hair out of my face. “Since you’re still not allowed to talk,” he said, “just snap your fingers if you need a break.”

I challenged him with my smirk. Bring it on, I thought.

He lashed the belt across my ass again. I clenched my jaw, whimpered with pleasure. He gave me another, this time in the middle of my cheeks. I pressed my forehead against the table and bit down on my lip to keep myself from moaning.

“Oh!” I gasped, when his next lash went to the bottom of my ass, right above my cunt.

He spit on my pussy. The warm, wet droplet made me shiver.

Then, with a lighter hand, Caleb cracked his belt over my pussy. This time I screamed. He lashed me again. We hadn’t even started fucking yet and I was already about to cum.

Caleb circled his fingertip around my lips. He entered me, satisfied by how wet I was, then circled his finger again.

He licked my cunt from top to bottom. From this angle, I was able to take hold of his shirt. I pulled him tighter against my pussy as his nose tickled the rim of my asshole.

I gasped, tightened my pussy, trembled, about to burst…

Caleb pulled away. “Not yet,” he said.

He prowled around the table as he decided what he’d do to me next. He looked so powerful, so confident in his suit. I liked the way his tattoos ran up his neck, just barely visible over his collar. I liked how his scarred knuckles juxtaposed with his flashy getup, a reminder of what Caleb was capable of when the mood struck him.

I looked up at him helplessly as he pulled his cock out. I inched forward with my mouth open wide. He was just close enough that I could stick my tongue out and taste him.

I got his head in my mouth. It began to slip out, I opened wider, took him in, felt him grow harder as I swirled my tongue around his head. .

He reached into his jacket and unveiled a small, egg-shaped vibrator with a plastic dial attached by a long cord.

He stole his cock away for a moment as he turned the egg on. It hummed as he ran it across my pussy, against my clit.

I opened my mouth wide in a silent moan.

Caleb pressed the egg inside me and offered his cock again.

“Yes,” I gasped as I closed my lips around his dick.

“Now what did I tell you about talking out of turn?” he said.

He yanked my head back.

“Open wider,” he said.

I obeyed. He forced his cock into my mouth until his balls smacked against my chin. He held himself there as I choked on him.

“Just say the word and I’ll stop,” Caleb teased. He thrusted into my mouth again, until I gagged.

I raised my eyes to him and realized it was a trick. ‘Say the word?’ I wasn’t allowed to speak.

And there was no way I was snapping my fingers.

“Good girl,” he said. As a reward, he turned the dial to a higher setting and the vibration inside me intensified.

He stopped throat fucking me but I continued to suck him. I took him as deep as I could, even as my jaw ached.

Caleb spun me to face the mirror. “Look at yourself,” he said.

I loved my reflection. My makeup had run down my cheeks. My hair was a sweaty mess. My ass and pussy shone ruby red from under my dress.

And there was Caleb, still completely dressed save for his cock sticking out of his pants. He looked like a horny CEO and I imagined I was his dirty little plaything.

Caleb popped the egg out of my pussy, got onto the table, and straddled me from behind.

He guided the egg against my clit. He pressed his cock against my pussy hole and held his belt at the ready.

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