Olivia’s Hypnotic Confession Ch. 03

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Clothed Sex

Before Mom married Frank, I knew exactly where I was going. No college, no big plans, just your average white trash trajectory. It wasn’t a great future but at least I fit, and I could always cross my fingers and hope that some big shot literary agent fell in love with one of my poems or short stories.

But since I joined the wealthy Montgomery family, I felt lost, adrift. Like one of those horror stories you hear about poor people who win the lottery, only to end up alienated, depressed, and generally unhappier than when they were broke.

I went to the window, peered out, saw Mom in some glorified cocktail dress, on Frank’s arm, stumbling into the car—half drunk already—probably for some early-afternoon cocktails at a fat cat shindig.

Whatever I would become, it wouldn’t be that.

Angry, frustrated, I snatched my notebook and pen. I scratched down two furious stanzas of poetry before I took a deep breath, read my work over, and realized that what I’d written sounded like a bad Sylvia Plath rip off, only worse, because now I was ostensibly a spoiled rich girl pissed off because I was suddenly wealthy.

Come to think of it, the few poems I’d written since moving into Frank’s mansion had all sounded like that. I tossed my notebook aside in disgust. “Well,” I said to myself, “I’m not wasting another day laying around here like a bum.”

An urge struck me to get a job, any job. That age-old instinct to earn one’s keep and not become a barnacle on someone else’s ship.

After a quick internet search I found a new big-box store that had just opened, urging new applicants to apply in person. (For legal reasons, I’ll say that the store totally wasn’t a Target.)

So I concocted a resume, threw on a semi-professional skirt and button-down top, pulled my hair back in a secretary’s bun, and got ready to show middle-management how badly I wanted to stack pants in the Women’s Department.

Of course, with my anxiety, the mere prospect of a job interview made me shudder. My nerves went haywire, and I knew that if I wanted to land the job, I’d need to self-hypnotize.

But Caleb had my talisman. He hadn’t given it back after our pool encounter last week, and I hadn’t seen him since. He was off with that new blonde he was dating. While Caleb usually resided at his dad’s estate, he owned a downtown loft apartment, a little home-away-from-home where he could take his Skank of the Week.

I texted Caleb to let him know I was coming, ordered a car, and headed to the loft. It was noon when I arrived. The smell of sex slapped me across the face as soon as I entered.

Caleb’s loft looked more like a gym than a home. A heavy bag hung in the corner, patched over in a dozen places. Free weights were scattered around one bench, with a barbell loaded with forty-five pound plates on the second.

But he had his most recent workout in bed. The sheets were a mess and the mattress hung halfway off the bedframe. The smell was worse there and I dared not get any closer.

“Back for more already?” Caleb called out from the bathroom.

“Try again shit head,” I said.

He emerged from the bathroom, shirtless, wearing sweatpants. He must have just gotten out of the shower; his tattooed torso had a moist sheen and water dropped from his hair, freshly slicked back. Caleb walked toward me like a panther, his every move deliberate. He flexed his abs, which made his six-pack tighten even more.

Well, I was relieved to see that nothing had changed with my sex drive. Without my hypnosis, I remained dry as a bone.

Besides, if Caleb had turned me on, I wouldn’t have been able to look at myself in the mirror. My eldest step brother was like an exquisite steak dinner that left you sick afterward.

And yet, I noticed something odd. Caleb wasn’t wearing my talisman. He must have worn it a lot recently, if the pendant-shaped tan line on his chest was any indication.

He must have taken it off when he fucked the blonde. Interesting.

As if to confirm my thoughts, he picked up the pendant from the night table next to his bed.

“Sure looks like you two had fun today,” I said.

“Her name’s Cortney and yes, she’s better than some,” Caleb said as he draped the talisman around his neck. He winked at me. “But can’t quite compare to others.”

I hurried to the bathroom as I muttered something about having to pee. I shut and locked the door behind me then looked in the mirror, horrified by my reflection.

I was fucking blushing, damn it.

But, thank God, I was still dry down there. I even stuck a finger in to make sure. At least I had that much going for me.

Caleb was dressed now, nothing special, just jeans and a T-shirt. He was fixing his bed.

“So what brings you here, my darling step sister?”

I pointed to the talisman. “My pendant. I need it for a job interview.”

“What job?”

I told him.

He recoiled. “As much as I loathe to say it, you’re a Montgomery now. Jobs like that are unbecoming of our station.”

“Your station,” I ataşehir escort said. “Not mine. I don’t know if you’ve noticed, but I’m not my fucking mother.”

“Okay Jesus, stop with the dramatics,” he said. “I’ll give you a ride if you want, not that I like it.”

“That would be great,” I said. “Now give me my pendant.”

Caleb lit a cigarette and blew the smoke in my face. “Nope. And when this day is over, you’ll thank me.”


My stomach was in knots when we got there. Luckily we were early, as the doors were just opening, with ‘only’ about a hundred applicants ahead of me. Within fifteen minutes, hundreds more had filed in behind us.

“I’m going to go sightseeing,” Caleb said, and left me without another word.

The managers had set up a long line of tables where they were doing the interviews. I clutched my resume, certain that I’d screw it all up.

God, I wished I were home. Not the Montgomery Compound, but the trailer, my little shit town, anywhere but here, and I thought I might make a break for it, run for the door, just go and—

“Next,” one of the managers said.

The manager was a middle-aged man with a knack for corporate backronyms, mission statements, and the importance of customer service while stacking pants. I answered mechanically, laughed at his jokes, and slowly became aware that the manager was hitting on me.

He smiled suggestively, stole a glance at my tits, unaware that I only entertained his awkward advances because I wanted the job.

Then I saw Caleb. He held a shopping basket filled to the brim. He looked dead at me, slid his hand into his pocket, and pulled out my talisman.

He dangled it between his fingers, swung it back and forth, back and forth…

The manager’s voice grew muffled, then vanished from my awareness altogether. The nervousness, the anxiety, the worry, gone away one-by-one like melting snowflakes.

I fell into my trance, suddenly calm, like a lake so still there wasn’t a single ripple in the water.

I dropped my resume to the floor, pushed away from the table, and went to him. We walked silently through the Women’s Department, to a set of fitting rooms just up ahead. Caleb pulled me into one, locked the door, and set the basket down.

“You’re in your trance now, correct?” he asked.

I nodded. My hair bun came undone and fell upon my shoulders.

“Good,” Caleb said. He tapped his finger on his chin, looked at me from head to toe, like he was drinking me with his eyes. “You don’t like me very much, do you?”

I grinned. “Nope, not at all.”

“But do you want me to grab you by the throat?”

I licked my lips. “Yes.”

He did, firmly, and pressed me up against the door. He nodded to that basket of goodies on the floor. “I brought some interesting things for you. Some of them will hurt. Some will make you scream. But I think you’ll like them. Are you interested?”

“Yes,” I squeaked, as his fingers tightened around my throat.

“Good,” he said. “Now one more question. Do you really want this fucking job?”


“I figured,” Caleb said, then pinned my arms behind me.

He kissed my neck, sucked me gently. I writhed my hips against him. His erection pressed against my stomach.

I breathed him in, smelled the light traces of cologne and, I thought, a lingering hint of Cortney.

Caleb kissed my mouth. I sucked on his bottom lip, brushed my tongue against his, took his jaw in both hands and ran my fingers across his stubble. Caleb grabbed my chest, found my nipples through my shirt, through my bra, and massaged them.

His hands shot to my hips. He spun me around to face the mirror on the door then bent me over. Caleb dropped to one knee, threw my skirt up over my hips, and yanked my panties off.

He licked his forefinger then made little circles around my clit. The tease lasted a moment before he ran his slick finger from my nub and worked backward as I stared at my own desperate, hungry countenance in the mirror.

His bottom lip brushed against my clit, his nose tickled my ass. He circled his tongue around my opening for what seemed like forever, and when he finally slipped it in for a taste, I moaned.

He put a finger over my lips. “That was strike one. Now keep quiet or else you’ll get punished.”

I reached back and unzipped his pants. Caleb’s cock emerged, stiff and eager. I stroked him as he kissed my neck, nibbled my ear, and grabbed me by the throat again.

I stroked faster, felt the first traces of pre-cum drip onto my knuckles. Caleb pulled my skirt higher. He looked powerful in the mirror as he stood behind me, did as he pleased, tightened his grip on my throat. I liked how the muscles in my legs grew taught as I bent over for him, I liked the way my hair fell into my face, and most of all I liked the hunger in my eyes.

I guided his dick between my legs. He stuck his head in then slowly pulled it out. I twitched in anticipation, and then came the next thrust, only slightly deeper than the first. kadıköy escort

I breathed heavier, leaned against the mirror, face-to-face with myself as Caleb went inside a third time, halfway in now, and I couldn’t help but moan again.

Caleb held himself in me, tightened his hold around my neck. “Strike two.”

He slid all the way in. I tightened my pussy around him and guided his free hand down to my cunt. He pulled his cock out and dipped his fingers inside me.

“Taste yourself,” he said, and slid his forefinger into my mouth.

I closed my lips around his finger and sucked my juices off him. I tasted sweet and good.

“Do I taste better than her?” I asked him.

He thrust into me, as deep as he could go. “Fuck yes.”

He pleasured my clit as he rocked his hips against me and, like a crack of lightning, a brief but intense orgasm rocked me.

This time I screamed.

I glimpsed his devious smile in the mirror.

“Strike three,” he said.

“Punish me,” I said. My voice quivered. “Please.”

He pulled three long silk scarves out of the basket. He tied them together, with a big knot in the middle.

“Now sister, you deserve every bit of this punishment,” he said. “But you won’t be able to talk, so I want you to kick me twice if it gets too—”

“It won’t,” I said, so deep in my trance that my voice seemed to come from someone else.

He grinned. “Open wide.”

He put the knot in my mouth. It was firm, but soft enough that it wasn’t uncomfortable. Like some seasoned craftsman, he worked methodically, raised my arms over my head, and snaked the scarves around them. Next he brought my hands together and lowered them behind me head, down to my neck.

Caleb bound my wrists together and pulled the scarves tight, pinning my hands behind my neck. I tried pulling free and at first panic rose in my throat that left me just on the cusp of claustrophobia.

But my excitement dulled the fear. Being vulnerable to Caleb’s every whim turned my entire body into a pleasure zone. He pulled my skirt off, leaving me bare from the waist down, and forced me to straddle the bench.

The knot in my mouth made me drool. Caleb wiped my lips.

“Drooling for me already?” he asked.

We heard footsteps outside. Caleb paused, eyes sharp on the door. He took me by the neck and pushed me down on the bench. The footsteps grew closer and Caleb ran his hand down my belly.

‘Quiet,’ he mouthed, then walked his fingers to my pussy.

His touch was subtle, meticulous. He tickled my clit, and just before I couldn’t take it anymore, he parted my pussy lips and slid inside, all while those footsteps thudded around outside.

I was panting, arching my back, trying my hardest not to let out a muffled scream that would surely get us caught.

The footsteps stopped right at our door. We even saw the work boots in the gap between the fitting room door and the floor. Some janitor making his rounds.

Caleb worked my clit again. How I kept myself from crying out, I’ll never know.

The janitor mumbled something to himself and walked away.

Caleb looked down at me. “Very good.” He pulled the belt out of his pants and held it up for me. It was the same belt he’d worn that day at the tattoo shop. “But you know what I have to do, Olivia.”

Caleb folded the leather belt. He pushed my ankles together then lifted my legs high over my head, exposing my ass.

“Remember,” he said. “There are always consequences to breaking my rules.”

He cracked the belt across my ass cheeks. I loved the pain and the last thing I would have done was tell him to stop, but even so, Caleb watched my legs intently, expecting me to kick.

He cracked it across my ass again. I could feel it turning red, I writhed my hips, trying to get to the cool surface of the bench for some relief. The very fact that I couldn’t reach it made the pain even better.

Caleb rubbed his chin. “I think we need to change things a little.”

He guided my legs down to a resting position. Now, sweetly, blessedly, my ass cheeks touched the cool metal bench.

“Get up,” he barked.

I just needed a moment of relief…

“Up!” he said, and pulled me off.

Caleb went back to his basket. He pulled a small comforter out, ripped it from its plastic casing, and lay it over the bench.

While he worked, I glimpsed myself in the mirror. I hadn’t felt the tears coming down my cheeks, the mascara running down my face in thin black lines. My hair was a mess, my lipstick was smeared from the gag.

I looked like Caleb’s fuck toy and I liked it.

Caleb took a rubber band from the basket. Near the bottom of the bench, he bunched up a handful of the comforter’s fabric, making a little lump, then wrapped the rubber band around its base. It almost looked like a mushroom. Opposite of that lump, Caleb lay a small pillow.

“Alright then,” he said, and grabbed me by the hair. He inspected my ass, gave it a slap then bent me over the bench.

He bostancı escort shoved my face into the pillow then spread my legs. That lump fit right up against my pussy, right up against my clit.

Caleb gave me another whack. Even as I cried out, I raised my ass up for another. With that movement, my cunt rubbed against the lump.

Caleb cracked my cheeks again as I started grinding my pussy against the comforter, dripping my wetness onto the fabric.

“You dirty little thing,” he said. “You might be enjoying this too much. Maybe I need to crank things up a bit.”

Caleb brought the belt down to my ass harder this time. He glanced at my legs, waiting for me to kick.

No way I’d ever do that.

Caleb laughed. “Just say the word and I’ll start fucking you.”

I tried to answer, but I couldn’t, with the gag.

“What was that?”

I moaned.

“Okay, I guess you like getting your ass spanked,” he said.

The belt cracked again. My ass felt like raw meat, my pussy was alight with pleasure as I rubbed it against the comforter. It was like I didn’t exist outside of those sensations, that sweet juxtaposition of pain and pleasure. At that moment, if asked, I don’t think I could have even told you my name.

Caleb hammered his dick into me. He throttled me, spanked me, and pulled my face up from the pillow by my hair.

Caleb fucked me so hard that between his cock slamming in and out of me and the belt cracking across my cheeks, I could hardly tell the difference.

Caleb knew exactly when to stop. He slipped his cock out and let me flop on the bench. I was a ragdoll at that point, unable to move, so overloaded that all I could do was go limp.

I wondered if Caleb ever fucked Cortney like this. As he paced back and forth, staring down at me hungrily, I knew that he didn’t.

A twisted pride flowed through me, because I knew that girl could never handle what Caleb was giving me now. She was too gentle.

But not me.

He pulled me upright then unbuttoned my shirt. He unclasped my bra; it wouldn’t come off with my arms tied behind my head, so he let it fall to my waist. He circled his fingers around my nipples.

“Are you ready?” he asked, and a mixture of fear and excitement ripped through me.

All that was left in his basket were two plastic clothespins. Caleb applied the first one to my left nipple, letting it clamp down gently. He watched my legs, waiting for me to kick, and as much as the pain flared, I refused to do it.

He put the other one on my right nipple. I gasped, tugged uselessly at my bonds.

“Keep tugging,” he said. “I like watching you struggle.”

He flicked each clothespin. That sting grew worse as they bobbed up and down, still pinching me, burning me.

“Up,” he said, then hoisted me onto my feet.

He led me to the rear wall. There was a steel coat hook bolted to it.

Despite the gag, I managed to smile a bit.

“My little eager beaver,” Caleb said. He lifted me a touch, and hooked that binding scarf to the wall.

There was a strain on my shoulders and I needed to stand up on my tiptoes to relieve it. I didn’t think I could endure this pain. No sensual burning, no satisfying cracks to ass, just the strain, hard on my back, my neck.

I was about to kick him to let me free when he dropped to his knees and threw my legs over his shoulders and lifted me up.

The relief was instant. Caleb tested me with one long lick over my pussy. I shuddered, squeezed my thighs around his head, and he began eating my rapidly.

He nibbled my lips, massaged my clit, kissed my thighs in rapid succession, from one to the other then back again, until I couldn’t keep track, until I was grunting, straining against my gag.

With my head bound to my arms, at this angle, I couldn’t even see Caleb. I was unprepared when he shifted my legs around his hips and got his dick in me again. Every thrust caused my tits to bounce, renewing the sweet, painful bite of the clothespins.

I wrapped my legs around him and pulled him closer, deeper, then bit down on my gag and cried out when I finally came.

Just as I went, Caleb did as well, releasing himself inside me.

He set me down, unhooked me, and untied the scarves. As they fell to the floor, I did too, feeling like I’d just run a marathon. Caleb plucked the clothespins from my breasts.

“That was new,” I said, still trying to catch my breath.

Caleb stuffed his cock back into his pants and snapped his fingers. “Up and at ’em, sister. I drove you out here for a job so c’mon, let’s go find one.”

He zipped up and left me there.

“Dickhead,” I called out to him.


There wasn’t a word between us on the ride home. I was fresh out of my trance, and still in the throes of my sexual runner’s high, so I didn’t mind that at all.

If we were going to keep this up, I’d have to learn how to separate Caleb from his cock. When I self-hypnotized, it wasn’t like I thought any more of him than usual. That revulsion as still there, it just took a backseat to, shall I say, the more agreeable parts of his nature.

I didn’t know if that was good or bad. Life had already put me through the wringer; by fucking Caleb, was I just fucking myself further?

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