Jay and Carly Book 2, Chapter 14

As I mentioned elsewhere, this chapter got reworked a couple times as I tried to make the characters work. I think I finally settled on a fun/hot way to weave everything together. Hopefully you enjoy it.

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“Hideo, watch after the girls, will you?”

“Of course,” he said, looking between his sister and I. My hand was on the small of Aimee’s back and the placement couldn’t have been lost on him. It practically screamed, “I’m going to be fucking your sister soon.”

“And you and Sherry keep your hands off each other, okay?”

Hideo laughed nervously and Sherry and Louise exchanged a look of pure lust. I hadn’t said anything about what they could do with each other. I lead Aimee to the door, giving the girls a little wave goodbye. We walked down the hallway and towards the elevator. “So why University of Miami?”

“Ohh… uhmm… I wanted somewhere warmer than Connecticut,” she said.

“Is your family from there?” I asked.

She eyed me, “Not originally, no,” she said.

“I wasn’t asking that.”

She looked at me appraisingly then averted her eyes, as if staring at me too long would burn her. “I’m sorry, Sir. I just have gotten used to that kind of question. We’re third generation Americans… at least on my father’s side. So it’s a little sensitive.”

“I understand,” I told her, guiding her out of the dorm after we hit the ground floor. “Well Miami is almost as big a melting pot as NYC so you are unlikely to get that here.” We exited through the glass doors of the large dormitory and into the bright, cloudless warmth of South Florida. “What do you want to see first?”

“Ohh… I’d really like to see the stadium,” she said. “And I guess the building where my classes will be.”

“Which building?”

“Uh… the Filipse building, I think,” she said.

“Hrmm… I think that’s this way,” I said, gesturing south.

“You don’t seem to know your way around campus very well,” she observed. She was 100% right, I had no idea where the Filipse building was but the signage was pretty good on campus and I’d planned on surreptitiously checking my phone at some point.

“Busted,” I said with a grin, “I just wanted to spend a little time with you.”

She blushed and looked away, “But you’re married.” Her tone revealed no trace of judgement or resistance, however.

“My wife and I have an… well… I guess you could say it’s a unique relationship.”

“I think it might be like my brother’s with his girlfriend,” she said quietly… “Or… well… maybe the opposite?”

“You’re very observant, Aimee.”

“Thank you, Sir. I can read Sherry’s tattoos though,” she said.

“Oh!” I stopped in my tracks and turned to face her, “So you know what they say and mean?”

She nodded, still eyes down. I grabbed her chin and forced her to look up to me. She was so small and petite I towered over her feeling much taller than 6’1. “And what do you think of her?”

“It would be wrong of me to judge,” she said quietly, a tone almost like terror in her voice.

“Why? People judge other people all the time.”

“It would be hypocritical of me to judge her… Sir,” she said, the last word spoken with a kind of reverence it hadn’t been laced with before.

“I see,” I said. “Does this lifestyle intrigue you, Aimee?”

She nodded.

“Tell me why,” I instructed, as we turned and continued our walk. I let my hand trail down to where it was much lower on her back, just resting against the swell or her cute, perky ass. She gasped as she felt my fingers snake under her shirt, grazing the sensitive bare skin.

“Do I have to, Sir?”

“Not if you don’t want to, Aimee. But I’ve learned every girl is different. And I’m better at making them happy if I know exactly what makes them tick. If I know them… intimately well.”

She nodded, “That makes sense, Sir. May I think about it as we walk around campus?”

“Of course, Aimee. I don’t want to pressure you,” I said, though my fingers dancing tantalizingly along the curve of her back probably belied that statement. It was a very warm day and, by the time we crossed campus and made our way to the building in question, we’d both worked up quite a sweat. It was a nice little conversation, neutral with just a hint of flirtiness. Suddenly, I saw a sign I’d not expected to see. Not a sign from the stars or any of that nonsense. No. An actual sign displayed on the sign of a building.

It read: “Join us on Tuesday to welcome guest lecturer Natalie Masterson.”

There couldn’t possibly be multiple professors named Natalie Masterson, right? It had to be Carly’s old roommate? This had intriguing possibilities written all over it. Before I could really start thinking about it, however, Aimee finally spoke up.

“You have to understand my father,” she said tentatively. “He was very, very strict with us growing up. And traditional. We knew he loved us but he drilled into us to respect our superiors. And he has some pretty traditional views on the role of men and women.”

“I get that,” I said quietly, wanting to let her do the talking.

“With some people, like my brother, it works. Hideo is exactly what my father wanted.”

“And you?”

She shrugged and looked away, tucking her hair behind her ear nervously. “Maybe halfway, Sir,” she said as she looked at me from the corner of her eye. “I’m always respectful and do what I’m told… but I see Sherry and... “

“You want to be like her?”

“NO!” she practically shouted, drawing some concerned looks from a couple passerbys. “No,” she said more quietly. “I just… I’m a little jealous of how open and… uhmm… unconventional she is. Like she doesn’t care about the world. My Dad loves her because she’s so meek around him. But then, when it’s just Hideo, she totally runs over him and he seems to like it.”

“So you want a guy like that? That you can tell what to do?”

“No,” she said, a little smile forming on her lips. “I want to be the meek one… but I want a little excitement, you know? That’s why I’m going to school a long ways away. I don’t want my Dad to find out how much of a freak I am… or how much I think I might be?”

I looked at her, trying to figure out what exactly she was telling me. After a long pause, I said, “Tell me what you want, Aimee.”

She just stared at me, saying nothing.

“Aimee, I’m going to tell you to do something and you’re going to do it, understand?”

She nodded, still silent.

“Go into that bathroom and bring me back your bra and panties.”

She squeaked out in surprise and actually hopped a little as if I’d frightened her, but she did exactly as she was told, walking off quickly to the bathroom I’d indicated. She quickly came back, her hands cupping the articles of clothing in an attempt to conceal them. She handed them to me and I examined them, making no attempt to conceal what they were. She blushed as I looked at the white cotton panties and generic beige bra. “Double D?” I asked, “Impressive.”

“Thank you, Sir.”

“But these underwear are terrible,” I said as I tossed them into a trashcan. “If you want to entice a guy who will keep you excited and submissive, you need to have sexier lingerie… understand?”

“Yes, Sir,” she said.

“Do you want me to fuck you, Aimee?”

She gasped, surprised at my bluntness. I slid my hand down the small of her back and enjoyed the shiver that descended down her spine at my touch. “Yes, Sir. Very much, Sir.”

“Are you a virgin?”

“No, Sir. A couple awkward encounters with a boy who tried to do it in an uncomfortable place,” she said, a twinkle in her eye.

“In your ass?”

She giggled, “No… the back of a Volkswagon.”

We laughed, I was surprised anyone so young would get the reference. “My Dad likes Kevin Smith, movies,” she said.

“Well shit… that makes me feel old.”

“I kinda like older men,” she replied, stepping closer to me as we walked. I could feel the heat radiating off over her despite the sun blaring down on us. We’d walked nearly the whole way around campus and seen everything we needed to see. I certainly felt like I knew everything I needed to know.

“Does your brother know about this side of you?”

“Of course not,” she said aghast.

“He’s going to find out today,” I said simply.

She squeaked again but said nothing, simply nodding. When we got back to the room, I paused at the door and turned to Aimee. “Are you sure you’re ready for this?”

She looked at me, confusion writ large across her face.

“I don’t know what’s behind door number 1 here when I open it but it’ll be something surprising. I can text them right now and call it off. You can live your life just like you have been if you want…”

“I think, sir, that I’d like to learn more. College is supposed to be about expanding your world, learning new things and pushing on boundaries, right?”

“A very healthy attitude,” I said before leaning over to whisper into her ear, “That I will take total advantage of.”

The words sent a shudder down her spine and I pulled back to face her, our lips inches away from each other. I loved that excitement of being with someone knew. That moment of thrill and exhilaration is intoxicating. It’s the thing that I never would have realized I was missing in a conventional marriage. But it was also what I was, in some ways, most happy about with this unconventional thing that Carly and I had. I leaned forward, our lips meeting for the first time. Her kiss was tentative and shy, almost passive. My hands trailed down her side and she whimpered as my fingers grazed against her exposed skin. “Tell me what you like?” I whispered to her.

“Anything? Everything?” she whispered back as if the question confused her.

“That’s not a lot to go on,” I said with a smile. “Though I admire your eagerness and openness.”

“It’s more than that, Sir,” she said, her hands were trembling as she struggled with articulating these new emotions and passions that had obviously been damned up within her and were now so close to breaking free. “I’ve always imagined myself as a blank slate. I want someone to teach me all the wonderful, decadent, erotic delights that they can. I like the idea of being molded like that. Of going into a relationship with no expectations or desires of my own and just being…,” she trailed off, searching for the right words.

“Taught?” I asked.

She smiled, “I guess… trained? Maybe. I’m not sure. Almost… brainwashed… but in a sexy way,” she said. “I know that’s a little messed up.”

“Trust me,” I said with a grin, “On the ‘messed up’ scale, you’re barely a 3 or 4.”

She smiled again then shuddered as she thought about something.

“What?” I asked.

“The thought of you turning me into a 10 on that scale is… kinda hot,” she said.

“Well, I’m about to fuck the hell out of you in front of your brother who I’ve cucked. That’s probably good for a couple points on that scale.”

“Fuck that’s hot, Sir.”

I smiled then placed my hand on her back, leading her both figuratively and literally into a den of depravity. I say that because the scene in front of us rivaled some of my wilder expectations.

Sherry was completely naked, astride Carly’s supine body riding a strap on that appeared to be almost too massive for her stretched pussy to accommodate. It was hard to get a good look, however, because Louise was slamming her own massive, plastic schlong into Sherry’s obviously abused ass.

Directly in front of Sherry was her boyfriend, watching with rapt attention as his wife was enthusiastically double fucked by my wife and girlfriend. “Fuck yes… even these plastics cocks are better than yours, baby,” Sherry said. She tended to get somewhat harsh with her boyfriend when she was cucking him. I had originally tried to step in and stop that, but Hideo seemed to very much enjoy it so I let them have their fun. I’m pretty much the last person in the world that should be judging the kinks of others.

Aimee, who’d been in stunned silence, finally found her voice and whispered to me, “This is your life?”

I snickered and said, “Yes, Aimee. This is my life,” in a loud enough voice that the others heard me.

Both Carly and Louise turned to me and said, “Master!” as if I’d just walked into a perfectly normal room with perfectly normal activity happening. Hideo’s eyes snapped up, looking at me, then his sister, then my hand that was obviously cupping her tight little ass. I looked at my employee with a cocky grin and said, “Hideo, I sure am glad I made friends with you. You have a habit of attracting little nymphos that want to spread their legs for me.”

I looked at his sister meaningfully and I could see him blush on the couch. Sherry barked out, “Look at me, baby. Fuck yes! You make me so happy, sweetie… oh, God… Sitting there watching me get stuffed. Fuck me harder, Louise, you bitch!...,” she wailed, giving into the distraction. She took some deep breaths as Louise obliged, slamming the plastic phallus in and out of Sherry’s ass repeatedly. She finally managed to continue, “Don’t I make you happy?”

“Of course,” he said to the tattooed nymphet currently being violated in front of his eyes.

“Then just keep finding… yesssss... willing holes for Master to… oh God... corrupt and everything will be…. Fuckfuck… fffffuck… fine,” she managed.

I turned to Aimee, focusing my attention on my newest conquest. “Are you going to be a good, obedient, slut for me, Aimee?”

“Yes, Sir,” she said cheerily.

“Take off your clothes,” I said.

She complied with trembling hands, staring me in the eyes as she quickly stripped herself bare. “Why aren’t you wearing underwear, slut?”

She flushed red, her whole body displayed for me. Her tits were large though not nearly as busty as I’d expected. They were shockingly firm, perfect orbs that were begging for use and abuse. I reached up, stroking the small, hard nipple. The tiny brown areolas were barely larger than the hard nipples they surrounded. Aimee sighed at the light touch, her knees buckling slightly and her eyes closed as she lost herself in the erotic sensation. She finally found her voice, whispering, “Because you told me to take them off.”

“Louder,” I said, pinching her right nipple slightly.

“Because you told me to take them off, Sir,” she said, staring me in the eyes. It couldn’t be more apparent from her body language and the look in her eyes that she was offering herself to me in whatever way I chose. The realization made me rock hard.

“And what am I going to have you do now, slut?”

“I don’t know, Sir,” she said softly.

“I’m going to fuck you until you cum while your brother watches. He’ll get to see his precious litter sister’s descent into depravity. He’ll know that I could snap my fingers and turn you into a tattooed little painslut like his girlfriend. He’s delivered you to me and I’m going to break you and rebuild you to be my vision of perfection.”

“Thank you, sir,” she said simply, a small smile appearing at the corner of her mouth.

I grabbed her by the arms, moving her firmly to the kitchen where I bent her over the counter, facing the debauchery in the living room. “Beg me,” I said from behind her.

“Please, Sir… stick your… uhmm… cock? In me… please.”

“Pitiful,” I said. I smacked her ass twice, the second hard enough to leave a bit of a small welt. While I did that, I was unfastening my belt and pulling it from the loops before unbuttoning and freeing my turgid shaft. All of the teasing and flirtations from today had left me unconcerned about foreplay. I simply wanted to sink into something hot and wet. “Try again, slut. Remember, I like dirty talking sluts.”

“Sorry, Sir. Please… fuck my pussy?”

I slid my fingers into her, feeling her cunt lips grip them eagerly, as if they longed to be splayed open by something. “Better… keep going,” I said. I guided the head of my cock to her moist slit, teasing it and stroking it with the hard slab of meat that was about to penetrate it for the first time.

“Oh yes… I need that,” she said. “I need to be used… fucked… trained… make me do things, Sir. Teach me how to be the best concubine I can be for your harem.”

“Spread your tight little cunt for me, Aimee,” I said. She reached behind herself, using her small, dainty fingers to expose the pink core between her legs. “Are you on the pill?”

“Yes, Sir.”

I smiled, “I like a slut that’s prepped herself for me, Hideo. Did you know she was this big of a whore?”

Hideo shook his head, “No,” he said with a smile. I could tell he was in erotic overload with everything happening, I honestly wasn’t far behind. I took the belt and tied Aimee’s elbow together, leaving her vulnerable and exposed.

“Once I slide into you, I own you… understand?”

“Yes, Sir.”

“I make the decisions. You’ll be my slut from now on, understand?” I said, rubbing the head of my cock along her flooded gash.

“Yes, Sir.”

“You’ll address me as, Master whenever we’re alone or I tell you to, understand?”

“Yes, S… yes, Master.”

“And the moment you deny me something, we’re done. Understand.”

“Yes, Master. Push my limits. Train me. I want it. I need it,” she chanted, shoving her hips back slightly trying to get to my cock.

“Good girl,” I said and I slammed into her, giving her the thing her whole body was craving. She screamed an exultant cry.

“Oh, God… Fuck, it’s soooo good,” she yelled. Her cunt squeezed around my cock and, for a second, I was actually afraid I was going to black out. I shook my head and managed to clear my vision as I pumped in and out of the tightest pussy I’d ever had. Aimee wailed away, her voice whimpering and grunting with each thrust as I slammed my hips back and forth.

Louise looked over her shoulder, giving me a bawdy wink before slamming back into Sherry roughly. As I started pounding into Aimee, both Louise and Carly watched me and we stared at each other. I found the experience strangely intimate, the three of us fucking in an odd rhythm, almost oblivious to the words and sounds of the girls we were so roughly violating. I continued slamming my hips into Aimee as she grunted and pleaded for more, sounding increasingly like the slut I had promised to train her to be.

I pulled out of Aimee who collapsed onto the countertop with a whimper. “You like that?” I asked.

“Hell yes,” she whispered.

“On your knees, next to Sherry,” I said.

She crawled over to Sherry, which isn’t what I had in mind, but I very much enjoyed the view as her tiny little bubble but swayed back and forth and her red, well fucked pussy winked back at me. She slid up beside Sherry, knees spread wide as if she too was riding an invisible cock. I walked in front of them and looked. Sherry was nearly glassy eyed, barely able to focus on me while Aimee looked up at me expectantly. Like a zealous devotee worshipping her God who’s suddenly burst fully to life. Her tongue was hanging out of her head subconsciously, giving her an especially vapid look that inexplicably made my cock harden. I took the shaft in my hand and started stroking it, not needing much attention after pummeling her tight cunt.

“Don’t wash this off until we leave this room, slut.”

“Yes, Master,” she whispered reverently as she strummed her clit.

“You can consider it an honor to wear my cum,” I said, feeling my orgasm about to burst forth.

“Of course, Master. This slut is honored…,” she started but her words were cut short by a huge spurt of cum leaping across onto her face. She gasped, then started stroking herself harder. She was cumming as the second shot hit her. Then a third and a fourth. The day of teasing had me boiling over and I dumped a pretty massive amount onto her face, covering her in cum which she licked up as it dripped onto her lips.

“Good girl. Now ride my wife’s face while you make out with Sherry. If you can make her cum before you do, I’ll keep you as a fucktoy.”

“Yes… Yes, please!” she said, immediately straddling Carly’s mouth which quickly got to work on her. “Ohhh,” she groaned in pleasure, taking just a moment to enjoy my wife’s nimble tongue on her abused cunt. She quickly got to work strumming Sherry’s clit while making out with Carly’s little sister, spreading my cum all over the latter’s face. It was a hot mess as I stood there watching these four women pleasure themselves with each other. Louise’s thrusts were jostling Sherry which kept causing Aimee to need to adjust. I could tell by the look in her eyes, that she was going to lose the race.

I knelt down next to Sherry and said, “Stop fighting it, Sherry. If you cum now, I get Aimee as my fucktoy and you get to be a bitch to Hideo for the next month.”

That did it. Sherry started cumming, screaming into Aimee’s mouth at first before cutting loose, “Oh fuck… fuckfuckfuck… FUCK!” she screamed. Aimee started cumming too, jerking and spasming as she looked up at me, her face still a mess.

As we all caught our breath, the girls extricated themselves from their positions. I leaned down, kissing Carly’s face as we nuzzled our heads together.

“You were trying awfully hard to make her cum,” I whispered.

“Was I?” she asked, her voice filled with false innocence.

“If I didn’t know better, I’d say you didn’t want me taking another fucktoy under my wing.”

“Of course not, Master,” she smiled and gave me a sweet peck on the lips, “I just want every girl you fuck to be the best they can be. They should work hard for the honor and privilege of kneeling at your feet.”

“I love you,” I said.

“I love you, too,” came the heartfelt reply.

“Your relationship is fucked up,” came a voice I didn’t recognize at first. I turned my head and saw Tennille standing in the kitchen. Next to her was Kimi. She did NOT look happy.