Jay and Carly Book 2 Ch 19

Long time in the works but hopefully you guys think it's worth it. Setting up a couple of things and teasing the return of an underused fan favorite. 

Victoria proved true to her word, teasing me as we drove back to campus. I had a lunch date with Louise that I didn’t want to miss, although Victoria’s oral skills were giving me serious thoughts of being slightly tardy. In the end, it was her willpower and not my own that responded to my alarm going off. She pulled off me without pausing and daintily wiped her lip before saying, “You don’t want to be late for lunch, Mr. S,” as casually as if she was telling me my 3pm appointment had been canceled.

I tucked my cock back into my pants and smoothed out my shirt before leaning over and giving her a gentle kiss of thanks. “You’ve gotten quite good at that, you know?”

“What? Sucking you off in the car without letting you cum so you can’t wreck and kill us?”

“Exactly!” I replied with a smirk. I swiped up on my phone, noting Louise’s location inside the building in front of us, “How about you take a trip to the mall and find something really sexy that shows off those nice tits while I spend some time with Louise?”

“Really?” Victoria asked, her eyes sparkled. She loved to shop but rarely got to do it with all the other stuff going on. She so rarely thought of herself instead of others that when I encouraged her to think selfishly she really responded well.

I blinked back my surprise, “Of course. Did you think I was going to make you just sit in the car?”

“Mr. S, I’m just the sexretary around here, remember? My role is to serve, not be served.” I stared at her for a moment until she cracked a hint of a smile before continuing, “But if you INSIST on me buying something slutty then I guess I have to do it, don’t I?”

I laughed at the formality of her speech and gave her another kiss. I let my hand wander up her shirt and across her large breasts resulting in a pleasant gasp into my mouth before I pulled away and repeated, “I’ll give you a call in a couple hours?”

She simply nodded, still slightly non-composed from the kiss. There’s no feeling better as a guy than knowing a kiss and stroke of your fingers can render a beautiful woman speechless. The thought lightened my steps and an onlooker probably would have thought I was skipping like a happy child.

“Room 309?” I said to a random guy.

He gestured to the stairs, “Third floor, 2nd or 3rd door on the left I think.”

“Thanks, man,” I said as I opened the doors to the stairwell and jogged up the two flights. The building was relatively new, a stark contrast to the college classroom buildings I remembered. State schools get rusty metal doors. Private schools apparently get the nice fancy wooden ones with gold handles. The door to the third floor hallway swung open easily and I looked down the hall. I saw Louise’s unmistakable leg dangling out from an office door. She was wearing a short, leather skirt that showed off the long smooth leg that I longed to have wrapped around me again. Deciding not to interrupt, I walked up quietly as the words filtered to my ears.

“Look… Louise, I’m very sorry… it won’t happen again.”

“I don’t know, professor. The inappropriate looks were enough… but this? I might have to tell someone.”

“Please… please don’t,” came the woman’s voice. What the hell was going on here?

“I expect this behavior to stop… can you stop?” Louise said. She had steel in her voice I rarely heard. The kind of hard tone she would normally have saved for Carly’s sister when she was wanting to bring my sister-in-law down a peg or two.

“I… I… I don’t know…  you’re so beautiful… what if I can’t stop touching you?”

What the fuck? I started forward but then Louise said, “Well… maybe we’ll have to make some other arrangement?”

Was Louise blackmailing her professor? “What kind of arrangement?” the other woman said.

“Well… I have this boyfriend… Have you heard of polyamory, professor?”

“Louise… I don’t think…”

“Shush… the time for thinking was before you fingered me in the elevator professor. Don’t you agree?”

“Yes,” she said, though the word sounded more like a moan than an admission.

“I like to share my boyfriend. I want you to fuck him,” she said.

“Bbb… bu… but… Louise, I have a wife… I’m not…”

“Not straight? Bullshit. Did you forget what I saw the first time I came to your office?”

“That wasn’t what you think…”

“You were practically stripping for one of your students!” Louise said with a laugh.

“I… I… I just thought that maybe… an alternative study reward might have helped him… He’s worked so hard this summer…” she said, her voice trailing off.

“Uh-huh. Worked hard? Done a lot of push ups and pelvic thrusts, has he?”

The professor didn’t respond and Louise continued, “Don’t worry… after you sample Jay, you won’t need another man… and he’s got plenty of pussy to keep your other… perversions… satisfied,” Louise said, lacing the word ‘perversions’ with all the contempt she could muster. I tried not to laugh. The thought of Louise being repulsed by some sapphic entertainment was almost humorous. The last time I’d hung out with Louise had been a near orgy and a very favorable (to me) cock to pussy ratio.

“Okay,” the voice came, though it didn’t sound sad. If anything, she sounded eager.

Suddenly Louise pulled back from the door and she looked down the hallway, seeing me just ten feet away. She smiled broadly and extended a finger to beckon me closer. “Here he is now, professor. Would you like to meet my boyfriend?”

“Uhhh…,” she stammered as I rounded the corner. The woman was about my age, maybe a year or two older with mid-length blondish hair that swirled in loose curls around her shoulders. Her breasts were prominent but not overtly on display and seemed perfect for her slightly above average height frame. My eyes flicked to the placard on her desk ‘Professor Katrina Chantage’. She was standing in the room, leaning against her bookshelf and the moment her eyes saw me I could practically feel the arousal flowing from her.

“Louise, what’s going on?” I asked as my cute little girlfriend tried to look all innocent. An act I knew all too well was exactly that… an act.

“Baby,” she said, drawing it out in that bratty little voice that served only to confirm she’d been getting in trouble, “My teacher here has been coming on to me VERY inappropriately.”

I looked at the two women, sensing that this was some kind of game but not entirely sure I understood it. Louise walked over to me and gave me a long, lingering, loving kiss before whispering to me, “I think she gets off on this.”

I still wasn’t entirely sure what ‘this’ was but I decided to play along. I walked over to the professor, standing just a little closer than would be otherwise appropriate. “Louise is mine, professor. I don’t like people making unwanted advances on her. Did she ask you to come on to her?”

“No,” she said, hanging her head.

“And did I hear her say that you fingered her in an elevator?”

“I thought she was flirting with me…” she protested feebly. I had not doubt that Louise had been doing exactly that but I kept my mouth shut.

“Well… I think none of us want this to get out, do we?”

“I’ll do anything to keep this between us. ANYthing,” she said. For the second time in 4 hours I had a woman offering me anything I wanted. A part of my brain pondered the miracle of my life. A much larger part of my brain was thinking less pure thoughts.

“I don’t have time to test that theory right now. But we’ll be back,” I said. I wasn’t 100% comfortable with the situation and wanted to talk to Louise. She seemed to have a better handle on what was happening. “Louise,  you okay with that?”

“Of course, lover,” she said, though the disappointment in her voice was evident.

I grabbed Louise’s hand and we walked down the hall, leaving the professor practically panting in her office. I felt good exhibiting a little bit of willpower though I was still confused about the situation. “What was that all about?” I asked as we exited the building.

“Honestly, I’m not really sure. I think she was into it… like being made to do things. Or maybe making people do things. I don’t know.”

“Weird,” I said, fully recognizing the irony of calling anyone’s kinks ‘weird’. Louise’s glance told me she realized it as well. “Huh… that reminds me. Remember me telling you about Carly’s roommate Natalie?”

“The blonde black chick? The one with the self-destructive kink?” she said after a moment of thought.

“Half black… but yeah,” I said, pulling out my phone and typing a message. “She’s coming to town for a lecture.

“Really?” Louise said, pressing up against me as we walked, “Are you going to have some fun with her?”

“Mmm… Would you like that, slut?” I said. I gave her ass a little squeeze.

“I’d like anything you’d enjoy, Mr. S. You know that.”

I typed a quick message.

Jay: Heard you’re coming to Miami. Only pack one suit for your lecture. No underwear at all.

I showed the message to Louise and she smiled wickedly and laughed. “You’re evil, Master.”

“Only to girls that want it. I’m never evil to you, am I?”

“No, Mr. S. You’re a perfect gentleman,” she said, her voice laced with over the top sarcasm. “You’re so sweet and kind when you fucked my ass and shoved my face into your pregnant wife’s juicy pussy.”

“I only did that because you guys like it,” I said with a smirk.

Both of us laughed at the ludicrous nature of the conversation. It felt nice to be alone with one of my girlfriends. Something about Carly, Kyrsten and Louise had always clicked differently for me. I loved a lot of my little harem. I cared for all of them. But those three were always just a little bit extra special to me and I hoped that would never change.

“How about you, me and Victoria have a nice little lunch and then you can come spend the night at the house. We can have a little fun?”

“That sounds heavenly… but I’ve got a paper I need to work on… and an 8am class tomorrow.”

“You took an 8am class? What kind of insane college kid are you?” I asked. I’d studiously avoided classes before noon when I’d gone to school.

“Not all of us are the gifted intellects that you are,” she said. A surprising bit of false modesty from Louise given that she was the only one of me women that could rival Carly for sheer genius. I waved my hand at the complement.

“Fine… I’ll have to find some other willing slut to fuck.”

“On this campus, shouldn’t be hard for a stud like you Mr. S.”

“Maybe I’ll just go back to your place and fuck Tennille while you watch?” I said.

“Would you?” she squealed as she clapped her hands in genuine excitement.

“Seriously?” I asked.

“Seriously… come back. Fuck her while I work on my paper. I’d love to hear you enjoying the slut and knowing that you’re happy since I can’t be the one to please you,” she said, then gave me a kiss and rubbed against my cock suggestively as she did. She pulled away and laughed in surprise at some thought.

“What?” I asked.

“Nothing… it’s just… I think Carly’s compersion complex is rubbing off on me?”

“Compersion? That’s a new one,” I said.

“It means that you genuinely enjoy that happiness of others.”

“Oh… doesn’t everyone though?”

“Not as many as you think… not like Carly does… and me now, I guess.”

“Interesting,” I said, pondering the thought. “Can you have that and still be jealous and possessive?”

“Only if the objects of that jealousy WANT you to be jealous…” she looked at me silently as we walked into her dorm.

“And do they?”

“Yes… almost all of us, I think.”

“Almost?”

“I mean… all of your main girls, yes. Carly, Kyrsten, me, Victoria… none of us want anyone else… and we all kinda like that you’re so possessive of us. It was hot at your bachelor party that you were so casual with some of the girls and so possessive of others. I think you found the exact right balance there. You seem to instinctively know what each girl wants and needs. You do a great job of giving her exactly that.”

My phone buzz and interrupted my response.

Natalie: I can’t give a lecture without at least a bra.

I showed the phone to Louise who seemed to ponder, “You could let her off the hook and give her one bra to pack.”

I nodded and started to type but as I thought about it, I realized that wasn’t the right response. Natalie wanted to be scared of me. She wanted to flirt with self-destruction. Hell, she wanted to BE self-destructive and it was the fact that she could trust me that allowed her to be that.

I typed a new message rapidly.

Jay: Do what you’re fucking told, cunt. Or you’ll arrive to a campus of people who have all watched a very interesting video. Understand?

The response was nearly instant.

Natalie: Yes, Master.

Louise just looked at me, “See… evil… but only to the girls that want that.” As the elevator door opened, I took a screenshot of the conversation with Natalie and sent it to Carly, knowing that she’d be really turned on by it.

We walked quietly to Louise’s door, both lost in our own thoughts. I was planning my imminent torment of the lovely Professor Natalie Masterson and was so wrapped up in the semi-erotic day dream I didn’t even register the girls in the room when we opened the door.

Both of Louise’s roommates, Kimi and Tennille, were there. Tennille shot me a warm smile. Kimi glowered like I’d run over her puppy. “It’s hard to remember a time you weren’t here,” she said and stormed off down the hallway to her room with a huff. At least she didn’t slam her door.

“Tennille, I can’t satisfy Jay tonight so I brought him to a willing slut. You up for that?”

Tennille’s eyes went to the ground shyly but she nodded, “Yeah… If he wants.”

I walked over to Tennille and grabbed her thin waist, pulling her close to me so she could feel my hardness. She gasped at the touch and pressed herself more firmly into me. My eyes met Louise’s who smiled warmly and silently mouthed the word, “Compersion”

I nodded and let my hands start roaming over Tennille as we made out. Louise grabbed her backpack and laptop off the counter and headed to her own room before calling out, “Oh… and be sure to be really loud. I want to know that my man is being taken well care of.”

Tennille moaned into my mouth as I kissed her even more passionately, “Let’s go to your room for some privacy.”

She just nodded as she caught her breath. “How should I dress up today? I’ve got a sexy genie costume. I could grant your every wish, Master,” she said seductively.

“No need for that today, my pet.”

We closed the door to her room behind us and her hands were instantly on me, pushing my shirt up and tugging at my belt. “Ooh… pet… I like that… I could put on a collar and leash and I’ve even got one of those but plug tails… I could be your little kitten…”

I pushed her down to the bed and unbuttoned her jeans before quickly yanking them off, taking her thin silk panties with them. “No… just you,” I said.

“But,” she said before I cut her off as my mouth descended to her delicate pussy. I dove in, my tongue finding her pussy already soaking wet. “Ohhhhhh,” she moaned loudly and I wondered if that was for me, for Louise or if it was truly the sound she made in the moment. Then I realized I didn’t really care.

I focused on pleasing her, teasing her and enjoying the way her body bucked against my mouth whenever I’d touch just the right spot. “Please,” she whimpered. I thought she was asking for some relief so I pulled away and looked up at her from between our spread legs. “Let me dress up as something that will please you,” she said.

The insistence on playing her little games was actually starting to annoy me slightly. “No,” I said. “Just you.” Before she could say anything else, I dove on top of her and kissed her. “I’m going to fuck Tennille now. Not slutty french maid Tennille. Not Slave Leia Tennille. Not King Kong Tennille,” I said, earning a giggle with the last. “I’m going to fuck Tennille Tennille,” i said.

She looked at me, “Nobody wants that,” she said. I thought the words were a joke at first and I laughed. Then I realized she wasn’t joking.

“I do,” I said. She melted. Whatever she was thinking. Whatever concern she had. It washed away. We scooted up in the bed and she wrapped her legs around me. I fumbled to get the rest of my clothes off and teased her wet cunt with my cock head, making her whimper with increasing desperation.

“Please… Please Jay… fuck me… take me… claim me,” she cried out. Her voice sounded desperate… forlorn almost. “I’m yours… please… make me yours,” she said, almost sobbing the words.

I could imagine Louise in the other room, trying to focus but rubbing her thighs together and smiling as she pictured Tennille and I just five feet away. The thought made my cock twitch which pushed the head into my current companion’s moist slit. She gasped in pleasure and shimmied her hips, taking me another inch in. Her pussy was tight and eager, squeezing at me like she never wanted me to leave. “You’re mine,” I said.

“Yessss,” she hissed.

“You… Tennille… you’re mine,” I said and slid the full length into her.

“Oh, God… thank you!” she screamed in what sounded like relief. Tears were flowing down her eyes. I pressed up and looked down to her. She was beautiful with her hair splayed out on the bed as she bucked up against me, desperate for a nice, hard fucking. She whimpered and pleaded without words. I twitched my cock inside of her which just made her eyes roll in ecstasy.

“You like that?”

“Yes.”

“Are you going to be a good little slut for me?”

“Yessss,” she managed.

“Good girl,” I said and I started fucking her hard. I wanted to hear her scream. I wanted everyone in the county to know that I was fucking her good. She didn’t disappoint. I started pounding her harder and harder, an ankle in each hand as I rammed my cock into her over and over without mercy. Suddenly, I felt like someone was watching us. I looked up, expecting to see Louise but instead saw Kimi at the door, leaning against the door frame. One of her hands was massaging her small breasts while the other was down the front of her shorts, obviously fingering herself furiously.

Our eyes met and she jumped but then continued what she was doing. She closed her eyes as she fingered herself and I realized that any endurance I may have managed to muster was quickly being depleted. Between the inexorable sucking grip of Tennille’s greedy cunt and the beautiful Asian girl masturbating to the site of me fucking her roommate, I really didn’t have much of a chance.

WIth a loud roar, I hammered into Tennille three more times. I turned my attention back to her, wanting to see her face when I finally came. She looked at me, sheer joy on my face as she sensed what was coming, “Yes… please… fill me up… thank you Jay. Thank you thank you thank you.”

I groaned and felt my cock pulse within her. Her pussy milked me, slurping every last drop out of me like it was the nectar of the gods. “Fuck that was good,” I said as I collapsed on top of her. My eyes looked to the doorway but Kimi was gone, probably retreated back to her room to finish what she’d started.  “You didn’t cum yet though did you?” I asked, kissing Tennille on the neck.

“I don’t need to… that was… that was better than anything… anything ever,” she said with a faroff voice.

“What?” I asked in confusion. “What was that all about, Tennille?”

She took a breath before adding, “I… I try too hard… I know I do… I’m annoying…”

“No you’re not,” I said.

“Shhh… let me talk. “I’m annoying and people don’t really like me… boys don’t like me… Hell… I don’t like me… But when I’m playing a role… wearing a costume. I… I can be myself?”

“When you’re dressed like someone else you can be yourself?” I asked, baffled by what was happening.

“Sort of… I can be a different person and if they don’t like me, that’s fine. They didn’t dislike me… they disliked the character. And a character can always be tweaked or fixed or changed. And besides that, boys like variety.”

“Not all boys,” I said.

“How many girls have you got?” she asked with a laugh.

I laughed in return and propped my head up on my elbow as I looked at her. My voice turned serious, “Exactly… I already have more variety than some guys will get in a lifetime. And I still wanted to fuck you.”

She blushed, “Really?”

“Why is that so hard to believe?”

“Nobody’s ever wanted to fuck me before… I mean… sure… they’ve wanted to fuck me… but not fuck ME,” she said as if that clarified things.

“You mean… you’ve never just fucked a guy without doing some intricate roleplay.”

“They’re not always THAT intricate. My first boyfriend just had me pretend to be other girls at school he wanted to fuck.”

“That’s fucked up,” I said, suddenly angry at her anonymous ex-lover.

“It’s fine… I kinda like it. It lets me be wild in ways I might not think of otherwise. Plus, acting like a bitchy cheerleader slut and getting hate fucked is kinda hot… you know?”

I nodded, knowing exactly what she meant. “I’m going to go check on Louise. Want to come?”

“I just did,” she replied, batting her eyes and smirking.

“Haha. No… come with me… I want to mess with her a little more. Lord knows Louise needs a bit of that.”

“She can be a little… much,” Tennille said tentatively.

“You know she teased me mercilessly for the first month of knowing her. Practically throwing herself at me like she was an easy lay before dancing away and telling me she was a virgin. It was… weird.”

“How’d you meet her?” Tennille said as she started to put her panties on.

“No… stay naked,” I instructed. She blushed but nodded. “Sherry was her roommate,” I reminded her.

“Oh… that’s right. So you were fucking her roommate and she was flirting with you like that?”

“Well… I guess I was fucking both of her roommates… although she didn’t really know that yet,” I said.

Tennille shook her head, “You are such a dog!”

“I’ll admit… my love life is… unconventional,” I said.

“I like it.”

Tennille took my hand and I led her naked down the hallway. I eased the door to Louise’s room open. It was such a stereotypically girly room. I felt like my eyes were being accosted by pinks and blues and pastel greens. All of which made Louise, sitting in a little black and white checkered dress typing away at her keyboard all the more out of place. The back of her head was turned to us as she transferred whatever words were in her whip smart mind onto the screen in front of her. I held my finger up to Tennille to tell her to wait. I walked quietly up behind Louise, completely naked and my cock already slightly hardened at the thought of messing with Louise. I placed my hand on her shoulder and she jolted with surprise.

“Ohh… shit… you scared me Mr. S,” she said, turning around and noticing my nudity. Her eyes glanced at my cock before looking up at me through her eye lashes. “Did you have fun with Tennille?”

“You know the answer to that… you listened, didn’t you?” I stroked her hair gently before giving it a tight grip and pulling her head back to stare directly at me.

“Yes, Master.”

“Did you touch yourself?”

“Yes, Master.”

“Did you cum?”

“Yes, Master.”

“Did I give you permission to cum?”

“N… N… No, Master. Did I need permission?”

“What do you think… slut?”

“All your sluts need permission,” she said with a whimper that made my cock twitch.

“So I should punish you?”

“Yes, Master.”

“Tennille… come here,” I said without breaking eye contact with Louise. Tennille walked forward and Louise’s eyes glanced sideways, seeing the beautiful, naked roommate walking towards us. My cum still leaking from her just used pussy and glistening on her thighs. Tennille came up to me, hugging me from behind and pressing her firm tits into my back as her hands roamed from my pecs down to my cock. She stroked it directly at Louise who stared with hypnotized eyes. “On your knees, Tennille.”

She dropped obediently and opened her mouth, knowing what I wanted. “Tennille is going to suck my cock while you keep working. You’re not allowed to touch yourself in any way. Not your nipples or pussy… not even your thighs. Don’t even rub your thighs together, understand?”

She whimpered at me as her eyes locked onto Tennille’s lips. She stared in rapt attention as those hot pink lips wrapped around my cock and started taking my cock. “Not… be a good girl and get back to work,” I told her.

“Yes, Master.”

Turns out if you’ve come twice in the last two hours, you can enjoy an expert level blowjob for a shockingly long time. Longer than I’d intended and I’d intended for Louise to endure a very frustrating punishment. Instead, she got about an hour of torture and torment as she squirmed her way towards a very distractedly completed paper. I, on the other hand, got to paint a new slut’s face with my cum and then watch my girlfriend practically fall out of her chair to clean up the mess. I think all three of us had a pretty good night.