Chloe in Trouble

I walked out of band and out through the quad. Ugh, I had 1st and 3rd periods today, nothing but male teachers. Annoying. They would just send me to...my cow! I walked over toward the main off and looked through the windowed doors of Mathew's office. She was talking with three men all in business suits and it looked like a really serious discussion. It would be a real shame if someone came in and made it really weird.

I opened the door and peeked in. "Cow, is now a bad time?" I asked her harshly. The men looked around at me and she looked nervously at them.

"Uh...no John, come on in." She said smiling at me. "This is John Kenway, one of our top scholars. He's actually going to..."

I moved around her desk and put my hands around her, groping her big soft tits. "I'm going to drink milk from my dumb little cow, aren't I? Cows don't talk, do they gentlemen?" I asked the men around the table. One of them stepped up and smirked with an air of authority.

"They certainly don't. They moo!" He said.

"Right, exactly. At this school, we take punishments very seriously gents." I pulled one of her massive udders out of her blouse and held it up to my mouth. "So what's all this about?" I took her big, swollen teat into my mouth and latched on, drawing milk out of her as the guys talked about shit.

Something about a new software system or something. They wanted to test out the schools in the area and see if we were compatible. I just nodded along and suckled as Mathews moaned in her low guttural mooing.

I felt my phone buzz and I pulled it out of my pocket without pulling away from my milky treat. It was Chloe. "Girls bathroom by the 500 building. I need you so badly." She added a winky emoji. I pulled off Mathew's tit and let the milk in my mouth spill out on to her breast, shoulder, and neck.

"I think that's enough of my cow for today. Thanks guys." I stood up and wiped my mouth on her blouse before leaving the room. Chloe wanted me in the girls bathroom? She was looking for trouble for me, excellent!

I strode into the room to find that it was completely empty. "What the....Chloe?" I asked.

"Hey John." I looked around to see Jessica Harper standing there. She was in a very little skirt with stockings and a lovely little top on that showed her tight stomach. She had a creepy little smile on her face but what REALLY drew my attention was the strap on hanging between her legs.

"Oh, hey Jessica. Sorry, umm...Chloe..."

"I'm here." I looked around to see Chloe. She was disheveled and sweaty and her clothes were all torn apart.

"Baby, what happened?" I asked. Behind me I heard a phone playing and I turned to see Jessica holding it up. There was a video of Chloe and Kelsey on my bed, playing together, from yesterday. "What is...were you filming outside my house?" I asked Jessica.

"I was just...looking out for you baby. My sweet John." Her voice was filled with an almost religious kind of zeal. Her eyes were glazed over looking at me.

"I know she did this, I was there."

"I know YOU know. Does the school know though? Would people see this video and think she was disciplining you? Or that she was a little lezzie slut?" Jessica was grinning wildly now. "And what if they saw this?"

The next video was taken here, in this bathroom. Chloe was on her back on a toilet seat, her legs spread while a purple strap on was pumping in and out of her little pink hole. She had bruises and her clothes were already torn like they were now. Her arms were behind her suggesting she may be tied to the toilet and she was talking in **** sentences. "Please, fuck me....please....ruin my little lesbian holes. Ruin me for John." She was trying not to cum, but it was overwhelming her and she bit down and she squirted all over this purple cock. Jessica giggled.

"Covering for her in one video might work, but two? No. People will know she's a good lesbian slut." This **** shit was so hot.

"Wait Jess. I'm sure we can work something out." I said, stepping closer to her. She cooed and smiled at me.

"Of course there is baby. I want you to choose me over her." She said flatly. I blinked.

"To what...go out with?"

"Yep. I want you to choose to go out with me over Chloe." Chloe smirked.

"Yeah, that's not gonna happen." She said proudly. I winked at Chloe but Jessica took my face in her hands and made me look into her eyes. Filled with a fanatical love.

"Oh don't worry my sweet boy, I don't want you to decide right now. I want you to fuck me first." The air was silent as she guided my hand under her skirt. I felt the tight little pink hole that I had tasted yesterday. "It feels so good doesn't it? You remember how yummy it was yesterday, don't you?" Chloe glared at me.

"You do?"

"SHUT UP! Consider this a game. If you cum in my tight virgin pussy and you never want to fuck me ever again in your life, then I will let you both go. I will release the videos and Chloe will be known as a hungry cunt lapper for the next three weeks and you will get to have her loose fucked out pussy forever. But, if my pussy is too good. If I am too tight and perfect for your cock and you want me again, you will be my boyfriend. You will dump her and I will delete the videos and give her a fresh change of clothes for the rest of the school day. Aren't I such a nice girl?" Jessica sang.

Fuck this was so hot. Jessica was holding my face so I couldn't look at Chloe. I just nodded. "Okay. I will play your game." I said.

"What? Baby, no! Overpower her and take her phone!" Jessica sneered at Chloe.

"See? She knows I'm gonna win, that's why she's trying to get out of this. I have these files saved on my computer you stupid bitch. This phone means nothing, here have it!" She handed her phone to Chloe. She threw it to the ground with disgust. "Baby, you don't have to do this." She pleaded to me. I did though, this was way too hot to pass up on.

"It's okay honey. You're really sexy, I'm sure you're gonna win." I said reassuringly. I sighed. "How do you wanna do this?"

"Right here baby. Just lie down on the ground, don't worry nobody comes in here it's clean." She had me lay on the ground. "I want your head in your ex's legs. I want her to be there when you experience the perfect pussy. You want him happy, don't you?" She asked Chloe.

"Fuck you." Chloe had no confidence in her voice. I lay on her legs and looked up at my girlfriend.

"It's okay, just hold my hand." She did and she kissed my forehead. "There's no way her pussy is that good." I said confidently. Jessica smirked at me.

"Time to find out." She walked over me and pulled her little skirt off. Her legs were so skinny and her pussy was so tight and puffy, it was hard to believe she was actually 18.

"Oh fuck." I said, looking at her pink slit again.

"Mmm, you just relax baby. Let your sweet Jessica take care of everything." She straddled my lap and positioned my cock under her. "Could you help me?" She asked Chloe quickly and casually. Chloe instinctively moved forward and grabbed my cock moving it right under her tight pussy. Jessica smiled wickedly. "Thanks, slut." She sank down slowly and smoothly, moving up and down so her juices would lube my cock as she went.

Every time she lowered herself I couldn't believe anyone could be that tight. "Oh fuck." I moaned in pure ecstacy. Chloe definitely lost already. I could see her start to cry. I looked back to Jessica who was settling in on my dick and she stopped when I felt her hymen.

"Alright my sweet boy. What's it gonna be? Ugh..." She whimpered. "Me, or her?" I didn't look at Chloe.

"You." I said quickly, needing to shatter that little womanhood. She bit her lip and sank down on my cock all in one motion. I was lost in pleasure, my cock was tingling and pulsing inside her perfect little pussy. I realized I was gripping Chloe's hand really tightly and I let go. "Sorry." I said looking up at her. She was covering her mouth and crying.

"Aww, it's okay Chloe. It's okay, he saved you. He saved your reputation and now he gets the tight, perfect pussy he deserves. A pussy that belongs only to him. Look how happy he is, how blissful he feels. Isn't it good that he feels that way? You still love him don't you?" I looked up at Chloe.

"Of course I do." She said in almost a whisper.

"Then watch this." Jessica started grinding on my cock, her little muscles already contracting and milking my cock for all it was worth. "Ohh baby. Your cock is as perfect as I imagined." She moaned sweetly. She started to bounce on my dick and she pushed her petite frame up and down over and over. I was totally lost in pleasure. The idea of humiliating my sweet Chloe was delicious to me at the outset of this little game, but I didn't expect to feel this fucking good. I rested my head in Chloe's lap and moaned mindlessly.

We sat there for about 30 beautiful minutes, Jessica just bouncing on her conquest and me awash in a river of endless pleasure. Jessica would cum every few minutes and her pussy would try to suck my balls out. Her little muscles were so strong and her pussy was so soft and wet. Finally I could feel my cock and balls tighten. "Baby, I'm gonna cum." I said.

"Cum for me sweetie. Cum whenever you want to, make me yours." She said moaning as we both reached our climax together. I again gripped Chloe's hand and I groaned as I felt my hips buck.

"Oh fuck fuck fuck." I bucked my hips more and more, pumping my hot cum directly into Jessica's sweet little pussy. MY little pussy. I sat up away from Chloe and held Jessica as we both convulsed and came together. The air was filled with our scent and the ground was slick with her juices. She quivered in my arms and then we both kissed, our tongues melting together. After what felt like hours, we finally came down and I got her off me. "Holy shit."

"I know."

"I've never felt anything like that." I said to her. "That was so hot how you **** me into it. Thank you." I said sincerely. She leaned up and kissed me.

"You're very welcome my king. Now, I have a promise to keep." Jessica snapped at Chloe. "Bring me my phone."

Chloe was a husk. Her eyes were darkened and her body was just limp as she sat there, her face caked with tears. She barely registered that her arm went over and got the phone and handed it to Jessica. "Thank you. I didn't have copies on my computer but now I don't need them." Chloe didn't react. "There, deleted. Nobody will know you're a lesbian. Now, I have something for you in my bag. Here we go." Jessica walked over to her bag and got out some clothes. "You don't wanna walk around naked all day do you? It's bad enough losing your boyfriend. You can change, and we can leave. C'mon baby."

I had more devious plans up my sleeve. "Baby, wait." I said to Jessica. She stopped and instantly rushed into my arms.

"What is it my king?"

"I feel bad for her." I said, glancing down at Chloe who still was just sitting there. "I love your pussy but I still have feelings for her." Jessica snapped.

"YOU CAN'T. We had a deal, John Kenway. You can't back out of it now!" Jessica was teeming with an instant anger. She was a complete psycho and I was definitely gonna have to cut her loose at some point, but for now I wanted to have more fun.

"I'm not backing out baby. I'm completely yours now." I kissed her and held her tight little body in my arms. "I just...she looks so pathetic like this."

"She IS pathetic my darling boy. You're finally seeing her how I always have."

"Babe, let's help her. Give her purpose." I walked over to Chloe and leaned down and ran a finger between her legs. "See? She's gushing wet, that really turned her on." I said. "What if we make her our ****?" I walked back over to Jessica and fed her Chloe's juices. Jessica's eyes lit up and she grinned.

"Aww, my sweet boy. You are so compassionate and that is why I love you. You're right, it's cruel to leave her here like this. She doesn't need to be alone, that's too much." She skipped over and sat next to Chloe. "Do you want to be our **** sweetie? Did you like watching Master and Mistress fuck like that?" Jessica took Chloe's face and made eye contact. "Don't lie." She said quietly.

"Uh huh."

SLAP!

"Yes, ma'am. Or mistress or miss Jessica. If you want to serve me....sorry, if you want to serve us then you need to prove it. We could just leave you here and you would never watch us fuck ever again."

"Please, take me. Miss Jessica." Chloe mumbled gently.

"Did you enjoy watching us fuck? Watching your superiors fuck, Slut? That's your new name, Slut."

"Yes ma'am. Watching you fuck was...so hot."

"Mmm, I bet it was. Master was kind enough to offer you slavery, what do you say to him?"

"Thank...thank you master." She said without looking at me.

"Say it to him." Chloe looked up at me for the first time since I came.

"Thank you...Master." She said softly.

"You're welcome Slut." I said. Jessica beamed at me and stood up. "You're only Slut when we're together, by the way. When other people are around you will be Chloe again." I said. Jessica smirked.

"No. You will ALWAYS be Slut, but you can ACT like Chloe when other people are around."

The bell rang for the end of 1st period. Jessica grabbed her bag and took my hand. "Let me walk you to class my loving king. Come along Slut." Slut stood up and walked over to us, changed in her new clothes. We all left the room together. "Take my hand Slut, there you go sweetie." We walked hand in hand, Me, Jessica, and Slut.

And that was only half my fucking Wednesday. Wow!