Kiernan Shipka Experiments

When I pulled out again, for the last time in that session, Kiernan dropped her legs down onto the bed, and then began to giddily spin in a half circle by kicking her legs on the bed. She ended up still on her back, but now she had her head closer to my cock. She looked up at me with a lip-biting grin and then opened her mouth to stick out her tongue. Of course I angled my cock and slid it down into her upside-down mouth, and then pumped it in a few times so Kiernan could taste herself on it again. As soon as I pulled out, she began to pluck my cum off her chest and suck it off her fingers. She did that several times, and then sat up on the bed.

"Hooo," Kiernan breathed out with a happy sigh. She stretched herself from side to side, and then leaned forward with her hands on her legs. "So, do you need to take a break?"

"Absolutely not," I answered quickly.

"Hehe, good," Kiernan smirked again. "I am going to get ready for what's next, and I will meet you there..."

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"Alright, a warmup like that is pretty simple," I said as I leaned back into my chair at the dining room table. "What did you want to do after that?"

Kiernan gave a funny little grin this time.

"Ok, so, I hope this doesn't sound too weird," she started. "As you know, I'm an actress. And even when the parts I play require me to...get close to someone in a scene, it's so hard to get into it with all the people watching. And really there's no way for me to really get into it, you know? Because..."

"You can't exactly fuck whoever you're filming a scene with?" I added.

"Exactly," Kiernan nodded.

"Alright, so you want to do a roleplay scene where you get to play someone else, but then you actually get to fuck?"

"Mmmhmm," Kiernan nodded with a closed-mouth smile.

"I like it, so what were you thinking of playing?"

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"Kiernan Gets to Roleplay"

I was now sitting behind my desk in the study. It was the closest to an office setting that there was in the house that would work for this scene. In an effort to make the scene as authentic as possible, I was wearing a suit and tie. Seated behind my desk, I looked up as I heard one of the double doors to the study opening.

"You wanted to see me, sir?" Kiernan called across the room as she poked her head in. The noise echoed through the spacious library.

"Yes, Kiernan, please come in." I waved her forward.

Kiernan stepped through the door and pressed it shut behind her. At first glance, my reaction was "holy shit." It was going to be difficult to draw anything out while she was wearing that.

Kiernan's costume consisted of a multi-layered ensemble. At the bottom, she was wearing dark blue ballet flats. Moving up, she had black tights going up her legs until they met a uniform-style skirt designed with a plaid pattern of black and various shades of blue. Tucked into the skirt was a white button up shirt, and covering that was a sweater-vest of the same dark blue color as her flats. Her white sleeves were rolled partway up her arms, and her collar was open on the shirt, showing off a silver necklace with a heart on it. She even had a blue headband at the top of her hair, holding it back just like her Sabrina costume.

"Kiernan, do you know why you were sent to my office today?"

"No..." Kiernan said quietly. She stepped forward meekly, holding her hands together at the front of her skirt, like she was a particularly shy girl. I watched her walk forward until she stopped in front of my desk.

"Sit down," I said as I pointed to the chair I had placed in front of my desk. Kiernan took a moment to smooth her skirt underneath her as she sat and kept her knees tightly together.

"Kiernan," I sighed, "You're 18 now. You're a senior. You can't keep getting sent to my office like this."

Kiernan shrugged, "I don't even know why I was sent here in the first place."

"Ms. Roberts told me what you were doing in class," I looked squarely at her.

"I wasn't doing anything!" Kiernan exclaimed, then shirked back down into her chair. "Ms. Roberts is out to get me."

"So Ms. Roberts is mistaken? And she didn't see you masturbating in class?"

Kiernan shifted nervously in her chair a little. I swear I even saw her blushing. She was very good.

"Yes..." Kiernan whispered. "She just wants me to get detention to keep me after school."

"I see," I said as I raised an eyebrow. "Well, the way I see it, she likely is mistaken."

Kiernan raised her eyebrows and looked at me across the desk.

"Because, honestly, it would be difficult for you to masturbate like she says you were. If you're wearing proper uniform."

Kiernan's eyes looked down at the floor while her head sulked down.

"Kiernan, you are wearing proper uniform, yes?"

There was no response, just Kiernan keeping her hands folded in her lap tightly. I sighed with fake exasperation and looked at her.

"Kiernan, stand up," I said with a stern voice.

Kiernan paused another second, and then stood up on seemingly shaky legs. Her hands stayed folded nervously at her chest. When I snapped my fingers and pointed to the space next to my chair, Kiernan cautiously took a few steps over until she was next to my chair.

I sighed again in fake frustration as I swiveled my chair to face her directly. Kiernan didn't look at me, acting perfectly like the girl who knew she was in trouble. I stood up, and then slowly began to step around her in a circle as I stared at her.

"Sleeves not down," I said as my eyes scanned her body. "Collar unbuttoned, tie missing. But that's not even the question, is it, Kiernan?"

She said nothing again.

"Kiernan, lift up your skirt."

Her hands finally dropped down to her legs, and Kiernan delicately grabbed the edge of her skirt with both hands and began to lift it up. The view increased until I saw that the tights she was wearing were actually black thigh-highs that ended with a lace ring around her thighs.

I shot my hand down to Kiernan's skirt, yanking it up to quickly finish what she was doing slowly. Just above where her thigh highs ended, there was nothing at all. Kiernan smooth perfect pussy stared back at me as I held her skirt up against her stomach..."Just as I expected," I said with disdain as I dropped her skirt. "And let me guess..."

I grabbed the bottom of Kiernan's sweater vest and yanked it up and over her head. Kiernan gasped and made a shocked yelp from me pulling her a little. I tossed the sweater aside and then grabbed at her shirt at the open buttons. The next button came undone, and I pulled the shirt away from her chest to look down inside her shirt. There was nothing there but a tease to some of the cleavage from her perky tits.

"No bra," I shook my head as I released Kiernan from my grasp. "That is, all together, 5 uniform infractions in addition to whatever you did to disrupt class in the first place. I have no choice but to side with Ms. Roberts and submit you to her punishment."

"No, please..." Kiernan folded her hands up together and held them up to her mouth to beg. "Puh-lease don't tell Ms. Roberts. Please. I'll do anything..."

"Kiernan, this isn't just a simple scolding, you need to be punished," I said, narrowing my eyes at her.

"Then you do it..." Kiernan said quietly.

"Excuse me?"

"You do it? Please, punish me...I'm sorry. I'll do anything...just...don't send me back to Ms. Roberts."

"I don't think you're understanding the difference between Ms. Roberts and myself," I said as I stared her down intensely. "I'd recommend you just go back to your classroom and do what Ms. Roberts says."

"No, sir," Kiernan stood up a little straighter now, almost defiant, "I would like you to punish me."

I sighed in frustration, remaining still for a moment. Then, with a sudden swiftness, I grabbed Kiernan by the shirt and pulled her closer to me. Kiernan gasped in shock as I yanked her forward against me, and then turned her around forcefully with both hands. I could hear the tiny breaths she let out, as if she were suddenly panicking, and then another gasp as I pushed her forward and bent her over the desk.

"Are you sure about that?" I asked as I flipped Kiernan's skirt up, exposing her toned ass. She stayed bent over face down on the desk, at a perfect height for her ass to be pushed out. There was a look on her face that perfectly displayed the worry that her character should be feeling in the moment, but having been with Kiernan loads of times by now, I could also see a slight hint of how badly she wanted cock in this moment.

"Yes sir..." Kiernan said quietly and then turned her head to look straight ahead.

"Fine..." I said with a firm voice. I then sighed and said with faux-frustration. "Senior girls...

I reached back with one hand, and firmly slapped it down onto Kiernan's ass. The clap echoed up to the vaulted ceiling of the room, and Kiernan let out a yelp that joined it soon after.

"I think two for each uniform infraction will do..." I said as I slapped her petite ass again. Kiernan yelled and stretched her arms out to grab the desk.

"Yes sir..." she said, between breaths.

I spanked her ass again, looking at her pale skin start to turn a slight hint of red as I hit the same spot.

"That's three," I said as I caressed my hand over her ass and down to her thigh.

"I'm sorry..." Kiernan whined as her face rested on the wood of my desk.

I didn't answer. I just slapped again.

"AH! I'm sorry..."

"I heard you..." I said before slapping again. "Five..."

"I won't do it again. I'll fix my uniform and-AH!" Kiernan was interrupted by number six.

"I'll pay attention in Ms. Roberts' class, I'll be good-AAAAH!" She yelled louder at number 7.

"And I'll never touch myself in class again!"

I paused, and then looked at her as she turned her face to look at me. Slap-slap-slap went the last three in quick succession. Kiernan winced and stayed bent over the desk, gripping the sides of it tightly with both hands as she looked up at me.

"So. Sounds like you just admitted to it," I shook my head and tsk-tsk-tsked at Kiernan as she looked up at me with a worried expression.

"And for that, I don't think a few more slaps is going to cover it."

Kiernan's eyes widened as my hand went back to her ass, caressing the red spot I had left behind. I finally took my hand off of it and scratched my chin in thought as I sat back down in my chair.

"No, this will have to be more severe. Suspension is more in line with an infraction like this."

"No!" Kiernan shot up instantly and took a step around the desk to be right in front of me in my chair, "Please no! If I get suspended and my parents find out I'll be in even more trouble..."

"Kiernan..." I said as I shook my head.

"Please sir, anything but that. I'm sorry, I'll do anything..." Kiernan sank to her knees in front of my chair and folded her hands together to beg again. "There has to be something I can do..."

"Kiernan, this isn't something that-" I started to say, and then I stopped myself as Kiernan's hands started to travel up my thighs.

"I'll do anything..." Kiernan repeated again. The look in her eye at this point was a mix between the anxiety her character had before, and the look that Kiernan always had that told me she was eager to please. Her hands moved up my thighs to the hardening bulge in my pants.

"You sure you want to do this?" I asked as Kiernan's hands touched the outline of my cock through my pants.

"Yes sir..." Kiernan nervously nodded as she looked up at me.

Kiernan's hands went up to my belt and unhooked it, and then followed through by unbuttoning and unzipping my pants. I shifted in my seat as she worked my pants down just enough, and then she reached inside and pulled out my cock.

"Oh," Kiernan went wide-eyed as my cock flipped out and hardened before her eyes. She was very, very good. For a girl who had fucked my cock dozens of times, she sold the act of seeing it for the first time very well. "Ok, um..."

Kiernan shakily put both hands on my cock, beginning to lightly stroke it up and down. She scooted her body forward, getting right between my legs so my cock was almost hitting her in the face.

"Do you want me to, um..." Kiernan stammered as she stared at my cock in her tiny hands.

"Use your mouth? You'd better..." I said sternly.

Kiernan eyed my cock and then leaned her mouth in. Slowly, nervously, she opened it and stuck out her tongue. There was a moment where her tongue touched the tip, and she froze, but then we made eye contact again, and that was urging enough for her to push her mouth onto my cock. Her lips parted as she took the head into her mouth and then slid down further.

She started slowly sliding her mouth up and down, taking it perhaps a little deeper than the character she was playing would know how to do, but I wasn't going to argue acting method when Kiernan had her lips wrapped around my cock. I moaned quietly and stared down as she worked it with her mouth while her hands stroked it slowly. Kiernan popped her mouth off and jerked my cock with her saliva as lube and looked up at me.

"Is that good, sir?"

"Yes, Kiernan. Don't neglect your tongue."

She took the suggestion, running her tongue along the underside of my shaft from base to tip, then swirling it around the tip before she locked her mouth on again. Her head slid up and down while her hands did the same, until she took one hand away. I watched as Kiernan slid the hand down and put it between her thighs under her skirt, playing with her pussy as she kept sucking my cock.

"Kiernan, that's what got you into trouble in the first place." I said.

"I'm sorry sir..." Kiernan said as she barely took her mouth off my cock. "I just...sometimes I need it so bad..."

I leaned down and took Kiernan by the arms, standing her up as I scooted forward in my chair. My hands wrapped around Kiernan's hips and grabbed her by the ass, and then I pulled her into me.

"Oh my..." Kiernan said as she allowed her legs to part and for her to straddle my lap.

"This will help..." I said as I held her by the hips and then pulled her down.

"Yes..." Kiernan breathed as she got closer into position. Both her hands came forward and held onto my shoulders. "Please sir, I need it..."

"Shhh..." I said as I gripped her hips.

Kiernan squared her hips and adjusted her legs to prepare to lower herself down. We locked eyes, and I pulled her down with one hand, while the other grabbed my cock until I felt her pussy touch the tip.

"Mmm..." Kiernan moaned quietly through a bit lip as my cock touched the opening of her pussy. She lowered herself down some more, and my cock started to split her pussy open.

"Ohhhh!" Kiernan moaned as she sank down on my cock. She adjusted herself, planting her knees on either side of my hips, and we slid back in the chair together. I sat back while Kiernan sank lower into my lap. It shoved my cock fully into her pussy as Kiernan moaned sharply again.

"Shhhh..." I shushed her again as I pulled her into my chest.

"It feels so good..." Kiernan moaned and started to lift her hips up and down to ride my cock.

Kiernan tipped herself up to look at me as she quietly moaned. We looked at each other, and then she leaned in and pressed her lips against mine. Both my hands went to her ass and helped lift her up and drop her back down on my cock. We continued to kiss as her soaked pussy smothered my cock with every motion. Kiernan moaned into my mouth and then leaned back, mouth still open as she stared into my eyes and kept riding.

"I'm sorry, sir..." Kiernan said as she worked her hips. "I'm sorry...I didn't mean to be a bad girl..."

"I know Kiernan," I reached up and cupped both my hands on her face as we leaned in to kiss again. Then we pulled apart and I smirked, "I know you're normally a good girl."

"I want to be a good girl..." she said as she rode my cock. "I want to be your good girl..."

She hit the word "your" so hard while looking into my eyes that I could have came right there. She didn't break character, but I knew she was grinning on the inside.

I brought both my hands up to her shirt and began to undo the buttons. I went up from the bottom, until the last button between her tits was left, and then undid that one. Kiernan's shirt fell open, and I slid it open further with both my index fingers, allowing me to see Kiernan's perky tits as she kept riding my cock. I only stared for a second, because then my mouth went to her nipples to lick each one.

"Oh my god!" Kiernan cried out in a high-pitched whine. "Sir I'm going to...you're going to make me..."

"You can cum, Kiernan," I said between licks on her nipple. "With me, you can cum all you want..."

Kiernan moaned out again and rocked her hips back and forth quickly in my lap, grinding my cock inside her and hitting an intense, close spot on her inner wall. Her hands grabbed my shoulders for leverage so she could go faster, and she kept her chest as still as possible to allow me to keep licking her nipples. Then she got faster, and louder, and her high-pitched moans hit a crescendo with her orgasm.

It took her a moment to regain her composure. At first, Kiernan looked at me almost like her old self, but she quickly got back into character by giving me exaggerated puppy-dog eyes.

"It feels so good..." Kiernan whispered out, sounding like she wanted more.

"Don't stop..." I said as I shifted in the chair.

The two of us moved together. Kiernan turned around and I remained in the chair, only I spread my legs open while Kiernan stood between them. She backed herself up, and then leaned forward to stick her ass out again. Then, she lowered herself down so my cock went up and between her thighs into her pussy from behind. Kiernan essentially sat on my cock with a moan, and I grabbed two handfuls of her schoolgirl ass as she began to lift it up and down on my cock.

Her skirt flipped up and down with every motion, until Kiernan reached back and grabbed it to pin it against her lower back, giving me a perfect view of her petite ass. Finally I couldn't take it anymore. I reached up and pulled her white shirt off her shoulders, leaving a bare back, and then found the clasps holding her skirt together at her hips. I tossed the skirt aside and enjoyed the sight of Kiernan riding my cock in nothing but blue ballet flats and black thigh-highs.

As amazing as it felt, I felt the urge to finish her in a way that had me standing up. I pushed Kiernan off my cock, and she quickly turned around and obediently put her hands behind her back. I came at her and grabbed her around the waist, and she put her arms around my neck as we began to kiss again.

I eased her back onto the desk, and then hoisted her onto it by lifting her up and setting her down. We continued to kiss until I laid her down on the desk, and she draped herself back beautifully. Her arms went up above her head, and her legs lifted up to allow me to grab and spread them open. My cock slid back into her, and I immediately starting thrusting hard and fast.

Kiernan cried out and gripped the desk above her. Her pussy was so wet at this point that I felt no need to hold back, character or not. I fucked her as deep as possible with every thrust, and watched it sink in each time as her legs stayed spread.

"I want it, sir..." Kiernan moaned as I fucked her. "I want it all..."

I know she did. Kiernan's pussy was clenching onto my cock so tightly I knew she wanted me to cum. Her core was flexed as she arched her back a little, and her kegels were locked, having me fuck her tight pussy as she held it. I leaned down one more time to kiss along her chest and lick her nipples, and then I stood straight up to savagely rail her pussy with my cock as I felt it.

My orgasm blew, and Kiernan felt it, looking up at me with wide, pleading eyes. I kept thrusting in hard as I felt myself start to cum inside her. Pumping my load into her pussy with such hard thrusts made it so that not all of it went deep inside her. By the time I was finished cumming, I could tell that Kiernan's pussy was leaking. I pulled out as she gave one more whiny moan, and then took a step back.