Jailen
I stood frozen as Harry backed away, watching me expectantly.
He undid his tie completely and took his blazer off. He tossed it to the side but left the tie dangling around his neck. When he noticed I wasn't moving he hummed, "Every second you take to get naked, that's another slap on your ass, sweetie. I don't mind, but you might not be able to sit for a week."
I leaned my head back against the wall as I inhaled deeply. I could run. He would definitely catch me, but I could do it just to piss him off. It was as if he could read my thoughts. He approached me again, his fingers coming between us to grab the waistband of my pants.
"If you think you'll make it out of this room, go ahead and try," He said, undoing the button on my pants, his rings cold against my stomach, "You think I'm pissed off now?" He yanked me forward by my pants and I gasped, "I want you to try and leave this room before I'm finished with you, Jailen. Take your clothes off, sweetie. I won't ask again."
He didn't have to ask again. I grabbed the hem of my shirt and pulled it over my head, barely having enough room to do so with him standing so close. I huffed out a breath of annoyance and dropped this shirt to the ground.
"Could you step back?" I asked, jutting my chin out at him.
He hesitated before he barely stepped back. I hooked my thumbs into my pants and slid them down my legs before kicking them to the side. I cleared my throat and straightened my back.
"These too," he reached forward and snapped the waistband of my panties.
I shuddered, the snap making my skin burn. He smiled lazily as I took my panties off and kicked them to the side with my pants. He stepped forward, his fingers crawling up my arm before he reached behind me and quickly undid my bra. He gripped the front of it and pulled it off of me. I hardly had time to blink before his hand was on my neck. He guided me forward as he walked backwards until the back of his legs hit the bed.
He took his hand off of my throat and sat down, spinning me so that I was laid across his lap and his hand grabbed the back of my neck, "You frustrate me," He huffed out, his hand ghosting over my ass.
I placed my hand that wasn't wrapped with the ace bandage flat on the ground and I kept the other up as best as I could.
"Getting this pretty ass spanked so early in this arrangement is usually a deal breaker for me. I don't like when people don't listen, Jailen. But with you," his fingers trailed up my spine briefly and I shivered, "I wanna keep you around as long as I can just so I can watch you learn to listen. I know you can be a good girl, Jai. Can't you?"
He landed a harsh slap on my ass and I gasped, my eyes widening at the force behind it. But he was quick to rub over the sting, his thumb sliding between my cheeks and ghosting over my asshole, "Answer me, sweetie."
I bit my lip and nodded, "Yeah."
He slapped my ass again, in the same spot with just as much force. My body jerked against his leg and I wrapped my arm around his calf, my eyes brimming with tears already, "Say yes."
"Yes," I whimpered out quickly as he slapped the other cheek once, twice, and then both back to back.
I screwed my eyes shut, the throbbing of my clit making its way down my legs. Why was I enjoying this?
"You wanna count? It might make this go faster," He said, the teasing evident in his voice as he rubbed my ass slowly, waiting for me to answer.
I nodded, ignoring the part in my brain that was telling me to tell him to go fuck himself.
"Ten," Harry chuckled, "Ready?"
I didn't even get to answer him before he was bringing his hand down on my ass again. Slap after slap, I counted. I held onto his leg for dear life, my eyes were brimmed with tears from both pain and pleasure and I couldn't help but let my head hang as I stuttered out the last number.
My breathing was heavy and my ass was on fire. I could feel the bruising forming and I'm sure it wouldn't have hurt as bad if he didn't have his rings on, yet I don't think I would've enjoyed it as much if he didn't. I stopped fighting my brain after the seventh slap when I realized I was dripping onto his thigh.
Harry stood up abruptly, his hand gripping my waist before I could fall and he turned, tossing me onto the bed. He put one knee up on the bed and leaned over me, his nose brushing mine, "Don't move until I come back."
I held my breath until he pulled away and walked out of the room. I sat up on my elbows, my eyes focused on the door and waiting for him to return. I kept my knees together and rolled my lips into my mouth. He took his time coming back, strolling back into the room casually before he kicked the door closed behind him.
My eyes zoned in on the black bag he had in his hands. He held it tightly as he walked to the other end of his room, grabbed the chair from the corner and dragged it to the bed. He sat the bag next to my thigh before he adjusted the chair so that it was directly in front of me.
He smiled at me and nodded his head to the bag, "Open it."
I sat up slowly, feeling a little self conscious under his gaze but my body was on fire. I liked the way he was looking at me right now, as if he was holding back from doing something he really wanted to do. He sat down in the chair and spread his legs, his hand coming up to unbutton his shirt.
I looked away and reached into the bag, retracting my hand when I felt the material. Harry watched me intently as I wrapped my hand around the item and pulled it out. The bag fell off of the bed as I examined the vibrator in my hands. It was heavy. It was purple with ribbed designs along the handle. I touched the head of the toy, my eyebrows raising at the smoothness of it before I looked back up at Harry.
"You've never had one and now you do," Harry said casually, "And you're gonna use it until I tell you to stop."
I swallowed, my mouth dry, my chest heaving and my clit throbbing erraticly as I pressed the power button, "I don't-" I avoided eye contact with him, "I don't know how to um..."
Realization dawned over his features and a grin made its way onto his face as he leaned forward. He grabbed ahold of my ankles and pulled me so that I was at the edge of the bed. I whimpered at the roughness of the sheets against my raw ass and he bit his lip.
"Open your legs," He took the vibrator from my hands and I leaned back on my elbows as I spread my legs for him, a little too eager to see what he was about to do. He reached underneath him and pulled the chair closer to the bed. His eyes dropped to my cunt and he cursed. He leaned forward and hooked an arm around my thigh.
I could feel his breathing on me as he trailed the vibrator up my inner thigh. I whined quietly and sucked in a sharp breath. He was so focused, I couldn't take my eyes off of him, not even when he teased the toy on my cunt by pressing it against my entrance and getting it wet.
He looked up, locking eyes with me just as he pressed the vibrator to my clit. My body jerked and I gritted my teeth. A chill slid up my spine and I balled my hands into fists. He moved slowly, circling the vibrator against me and I moaned lowly. He nodded his head, his hand that was wrapped around my thigh digging into the flesh, "You want a turn?"
I nodded, my hand shaking as I reached out and grabbed the top of the toy. He pulled his hand away and sat back in the chair, even though it was still close enough. Maybe even too close. I leaned on one elbow as I looked down between my legs, trying to keep the same rhythm Harry had. I was in awe, my mouth hung open as I watched the vibrator become coated in my juices when it accidentally slipped from my clit.
I raised my leg and got more comfortable, moaning a little too loudly when I pressed the toy against my throbbing clit again. I pulled my bottom lip between my teeth and moved the vibrator from side to side. This was all so new, yet it felt so familiar. So good. I ached with need and couldn't help myself as I clicked the button next to the power button.
The tempo changed and I squeaked. The rapid pulse pushed against my cunt with a roughness that made my body shake. Harry chuckled and I looked up, my stomach clenching when I noticed he was already looking at me. His eyes weren't focused between my legs, they were on my face.
"How does it feel, sweetie?" He asked, his hand hovering over his belt.
I rubbed the vibrator in circles, "S-so good, fuck."
I was approaching that peak that had become all too familiar this weekend. I pressed the toy harder against myself and my breathing stopped. I threw my head back and screwed my eyes shut, my whimpers filling the air as my hips bucked into the toy.
"Hold it there," Harry mumbled, a warning edge to his tone that set me off.
I clutched the vibrator tightly in my hand, my thighs shaking as pleasure washed over me. I screamed, a thin layer of sweat covering my body as I forced the toy away from my cunt when it became too much.
Harry leaned forward and grabbed my hand, bringing it back between my legs. I hissed when the vibrator touched my clit again and my body spasmed.
"I didn't tell you that you were done," He said, sitting back and unbuttoning his pants, "Listen, Jailen. Keep going."
He lifted his hips to slide his pants down, groaning quietly when his cock sprung out and rested agaisnt his stomach. He took himself in his hands and stroked slowly.
My breathing hitched at the sight and I pressed the vibrator to my clit, my moans coming out in stutters as I watched his hand move up and down. But he surprised me. My eyes were wide as he took his hand off of his cock and put it between my legs. He locked eyes with me as he slid two fingers in my cunt and pumped a few times. I clenched tightly around his fingers as the vibrator nearly fell from my hand again.
He pulled his fingers out slowly and sat back, his hand glistening with my juices as he began to stroke himself again. It didn't take long until his cock was wet as well. The mix of his precum and my juices made his cock slick as he fucked his hand.
My cunt clenched around air, I felt empty without his fingers, but just knowing that they were inside of me was enough to tighten the knot in my stomach. I grinded my hips against the toy, feeling myself drip down to my asshole. My face twisted in pleasure as I lolled my head to the side, my limbs becoming tired as I moved the toy faster against me.
"Harry," I whined out and he cursed.
"There you go, baby, you're doing so fucking good," His hand moved faster against his cock and he moaned, tossing his head back briefly before he locked his eyes on my cunt.
I spread my legs wider as I came again and Harry leaned forward. He used his hand that wasn't stroking his cock to spread my swollen pussy lips, sliding his fingers back into me and immediately curling them upwards.
"Oh fuck," I kept the vibrator against me as he fucked his fingers in and out of me, hardly giving me time to come down before I was tensing again and yelling his name.
"I feel it," Harry grunted, his hand working his cock furously as he fucked me with his fingers, "Give it to me, sweetie, almost there."
My wrist was hurting as I fisted the sheets. I couldn't breath and my cunt spasmed wildly as wetness flooded my thighs. Harry licked his lips as I sprayed his face, his fingers never letting up even though the sheets were ruined. I whimpered at the sight of my juices dripping from his face.
"Don't stop," he demanded and I fell back against the bed, my arms weak.
I brought my knees up to my chest and continued to play with my clit. The toy was slippery and my hand was starting to hurt from trying to keep it in my hand but I didn't stop. I wanted another release. I needed another one.
My stomach was on fire, sore from how hard I was heaving, and my spine ached from how hard I was arching. It wouldn't take much to cum this time. I could feel it. It was right on the tip of Harry's fingers as he rubbed my g-spot at an agonizing pace.
"Please," I begged, screwing my eyes shut as my body shook.
"What do you want, Jai?" He asked, his voice sending a chill up my spine, "Tell daddy."
"Faster," I choked out, tears of frustration falling from my eyes, "Please go faster."
He didn't miss a beat. The moment the words left my mouth, he obliged. He pounded into me relentlessly, the force making my body jerk against the sheets. I didn't even have time to prepare as another orgasm stretched through my body. The vibrator fell from my hand and he stood up from the chair to catch it against his palm. He pressed his hand firmly against my cunt so that the vibrator was still against my clit as he continued to finger me.
It was euphoric. I swore I was seconds away from death as my body went rigid and the only thing I could feel was him between my legs. I brought my hands up to my chest and cradled them as I pulled my lip between my teeth to contain some of my moans. It didn't work.
Especially when he roughly pulled his fingers out of me and tossed the vibrator to the side. I looked down at him as he pushed my legs apart and put his wet hands on my inner thighs to hold my legs down. He rubbed his cock between my folds, moaning and whimpering as he continued to get himself off.
He leaned his weight on me, pushing my legs so far apart that it was starting to hurt but I couldn't care less as I watched his cock twitch until he spilled onto my clit. White ribbons covered my cunt and he slowed his hips, taking one hand off of my thighs to hold his cock in his hand and rub his cum up and down my slit.
My mouth hung open, shaky breaths escaping as I blinked away the tears.
Harry finally stopped and I let out a sigh of relief. He licked his lips and sat up straight, flicking my clit once and making me snap my thighs shut, "You're staying with me from now on. When you're ready, Jonah will take you to get your shit from your apartment."