Jay and Carly Book 2, Chapter 6

sorry for the delay. I rewrote the end because I changed some timeline stuff and had to fix a couple things. Was your guess about Lilith right? Did you correctly identify her kink? Read on to find out!

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"Yes, Master!” Carly said as she hopped up, full of happiness and pep. I folded my fingers together and rested my head on my hands as I watched my wife prance into the bathroom to get ready. She shook her ass sexily, probably fully aware that I couldn’t take my eyes off her tight little butt. I watched her slip on a pair of heels and she shot me a sultry, sexy look. She knew the effect she had on me. She lived for it. She disappeared in the closet for a moment and I heard her rummaging through boxes and drawers, looking for the skimpy French maid outfit we’d bought months ago. She’d only worn it once, a night when she’d played sexy waitress to Madison and I while Dave, Madison’s husband and my subordinate at the company, sat in the corner and watched me first seduce, then fuck his wife. I don’t think the similarities were lost on her. Tonight she’d be serving Kyrsten and I while I seduced yet another woman. Or at least that was the plan. 

While Carly continued to search, Victoria returned. Fortunately, the water I was sipping on wasn’t in my mouth when she walked in. Otherwise I’d have done a spit take worthy of a sitcom. She walked in wearing a pair of thigh high boots and a short black skirt. The skirt looked nearly painted on and left about two inches between the boots and the bottom of the skirt. The top was a thin, almost sheer, white halter top with a cutout that practically created a bullseye on her massive cleavage. The lacy red bra she had underneath peaked through, adding that extra bit of slutty flair to an outfit that already had that in spades. She bit her lip, looking at me silently for approval.

“You almost wore THAT to work?” I asked. I gave her a warm smile of approval as I gestured for her to turn around. 

“Not really, Boss. I wanted to but knew I’d never get the courage. Plus it would have put you in an awkward position and I never want to do that. If you’d asked me, I would have come in on the weekend wearing it though,” she said with a whimsical smile. As she twirled, my eyes traced her curvy outline, noting that the skirt just barely covered her ass and the whole outfit served to flaunt her nice waist and huge tits. 

“Well… now you get to help me land another woman. What better way is there to serve me?” I said. I laughed and she joined in with a girly giggle. 

“There’s no better way to serve you, Boss. It’s both my job as your secretary and my heart’s desire as your work-wife.” She pulled the halter top to the side, revealing the words of her tattoo that spiraled around her breast. ‘I am filled by my beloved and all his desire is fulfilled by me SS 7:10’. She traced the words with her finger which also served to tease her nipple harder. “I want to help you fulfill ALL your desires, Mr. S. If you desire her, then the only appropriate thing for me to do is to help you achieve that desire.”

Her breathing was heavy and her arousal was nearly palpable. I wanted to grab her and fuck her again, just to fulfill the first part of her tattoo. She needed to be filled by me. However, there was a bigger plan to execute. I forced a deep breath. Then another. “Sometimes you make it very difficult to get out of the bedroom, Victoria.”

“Is that a complaint, Boss?” she said, adopting her sultry, obedient sexretary voice. 

“Not even a little bit.”

“Little isn’t a word I’m used to hearing around here,” came Kyrsten’s voice. She stepped into the door frame next to Victoria and my jaw hit the floor. She was wearing a gorgeous purple dress that was somehow both loose and clung to her body like it was vacuumed on. It was like the dress was tailored for exactly  her shape and just naturally followed every contour and curve of her body like a second skin. My mouth watered and my cock hardened just looked at her. The two thin straps over her shoulders held the dress up and, more impressively, held her breasts in. 

Victoria whispered, “I think our Master likes your dress.”

Kyrsten looked at me and then at Victoria. She stepped forward and lowered her voice, “I think he likes how both of us are dressed.” Kyrsten reached around Victoria, grabbing the taller woman’s waist and pulling her closer. Victoria looked at her then closed her eyes as Kyrsten leaned into a soft, tender kiss. I just watched as two of the most lovely, sexy, gorgeous people I’d ever met silently made out in the door to my bedroom. It wasn’t the lusty, impassioned kisses that were part and parcel of the new Simpson household. Instead it was gentle, caring and sweet. As Victoria sank into the kiss, she gave a contented murmur of approval. 

As they kept making out, Carly finally emerged from our closet. She’d found the maid outfit. Frilly little skirt. Little black heels. Lacy Choker. Think Yvette from Clue but dialed up a notch or two in the sexualized department. “Master, what do you… oh… you two are having a little moment aren’t you?” Carly said with amusement as she too watched the fiery redhead and dusky brunette make out. They broke apart their kiss, Kyrsten looking decidedly proud of herself and Victoria appearing almost embarrassed.

“Sorry, Mr. S. I… uhmm… I got a little carried away.”

“No complaints from me.”

“Or me,” Carly said.

“And certainly not me. You’re a very good kisser, Vic,” Kyrsten said. The complement made Victoria blush and she scurried away.

“Okay, enough teasing the help, Kyrsten,” I said. 

“Sexretary,” came Victoria’s correction, “Your wife is ‘the help’ for the night!” Her voice echoed through the house causing all of us to laugh. 

“Mmmm… I like that. I like being just ‘the help’ for the night, Master,” Carly said as she stood there gently rubbing her thighs together. 

“Good… now get downstairs and help Victoria get dinner ready.”

“Yes, Master,” she said. “I’ll be happy when Sasha finally arrives. My cooking isn’t exactly my strongest asset.”

“Silly slut,” I said, giving her ass a little swat. Carly yelped and sauntered off, shaking her ass as she walked away while I watched her almost hypnotic retreat. “And you… we’ve got about 30 minutes before the good doctor gets here. You think you can keep me turned on and primed for that whole time?”

“Mmmm… I could try,” she whispered as she dropped to her knees in front of me. She proceeded to tease me and pleasure me for what seemed like hours while we waited on our guest’s arrival. It was almost a relief when I finally heard the car tires crunching across the sandy, shell covered driveway. Kyrsten climbed up, gently tucked me back into my pants and moved to the mirror to fix her hair and lipstick. I finished getting dressed while I listened to the conversation downstairs. 

Victoria answered the door and said, “Welcome, Doctor Shadam. Please come in. They’ll be down in just a minute.”

“Oh… uhmmm… they?” the Doctor asked, probably confused both by the implication that there were two people upstairs and the presence of this slutty assistant greeting her at the door.

“Yes, ma’am. Miss Elias and her fiance are upstairs… finishing.” I could almost picture the coy look Victoria probably had on her face as she delivered that line. 

“Uhmmm… alright… I guess I’ll… Oh! Carly? Mrs. Simpson?” she asked, having gotten a glimpse of my wife, apparently.

“Yes, ma’am?” she said, complete innocence in her voice.

“You… you work here? For Kyrsten?”

“Yes, ma’am,” she said. I heard clinking of glass and assumed drinks were being poured. By this point, Kyrsten had joined me at the door and we were trying to avoid laughing audibly as we imagined the good Doctor’s barrage of confusion.

“And she makes you dress like…. Like that?”

“Oh no ma’am. I demand to dress like this. I wouldn’t be the Master and Mistress’s maid if they didn’t let me dress this way.”

“Oh,” the doctor managed before taking a long pull from whatever drink Carly had poured for her.

Kyrsten recognized her time for an entrance and went down the stairs, leaving me waiting for a moment longer. We’d decided not to overload her. Keep her confused and off balance but don’t make her run screaming. Hopefully we could thread that needle. 

“Oh… Kyrsten… uhmm… this is for you,” she said. “It’s my favorite vintage.”

“Thank you. We’ll try it after dinner, I expect. You’ve already met our assistant, Victoria, and our maid whom you already know.”

“Yeah… I mean… yes… I’m a little… taken aback? I didn’t realize you even had a fiance. Let alone could afford two personal assistants. I think your commission might be a little too high,” she said, trying to defuse the tension with a joke.

“Oh, they’re not really mine. They’re my fiance’s. I just get to… shall we say, enjoy the benefits.”

“Uhmm… I won’t even ask,” Lilith said, trying to move past the sexual tension. “He’s a very lucky man, I suppose.”

“He is. But you’ve already met him.”

“I have?” she said in confusion, trying to conjure up who Kyrsten could be talking about. “Are you dating one of my staff? That wouldn’t be appropriate.”

Now it was my turn to make my entrance. As I descended the stairs, I felt four sets of eyes turn my way. “Not a staff member, Doctor,” I said.

“Mr. Simpson? What…?” she said in confusion. I got my first look at her outside of her scrubs. 

She was wearing a nice, shoulderless black dress. It was modestly cut, only hinting at the exquisite form underneath. She’d let her long blonde hair down and it cascaded nicely across her shoulders, framing the full breasts that wanted to burst free from their confinement. The dress had a long slit up the side, giving a tantalizing hint at her thigh which poked out because of the way she was standing. 

“I thought Carly explained our lifestyle, Lilith,” I said as I stepped closer to her.

“I mean… she did… some… I guess. Maybe I should have more thoroughly queried both of your sexual histories,” she said, dropping into a slightly clinical voice as she attempted to recover her composure.

Carly took the now empty glass of wine from her hand and Kyrsten handed her another one. She barely noticed. As she gave her the glass, she gently brushed the Doctor’s fingers with her own, “You probably didn’t have enough time. It’s a VERY long story,” Kyrsten said. 

Lilith blinked away her confusion, “So you’re married to Carly… And you’re dating, er, engaged to Kyrsten?”

“And I brought my secretary from New York,” I said by way of clarification.

“To run your home office? Dressed like a slut?” she said with thinly concealed venom. 

Victoria shifted her weight, suddenly uncomfortable. This wasn’t the sexy game she’d envisioned it being. “She dresses how I tell her to,” I said simply, forcing myself to be calm. Lilith looked at me. Her expression was cold and unreadable. 

“How you… tell her to?” she asked in a clipped, dangerous voice. 

“Is that a problem?”

The doctor looked at the girls and I tried to put myself in her shoes. What was she seeing? A wife dressed as a hyper sexualized maid. Being asked to cater at a party for her husband’s girlfriend. A successful, ambitious saleswoman dressed in an insanely sexy dress and purporting to be the fiancee of an already married man. A third woman. A stranger. Dressed in some schoolboy’s fantasy of what a slutty secretary might wear for her boss. Victoria was the only one who looked uneasy at the scrutiny being placed on her by the buxom blonde. She fidgeted and looked embarrassed?... Concerned?... Scared? What emotion was Lilith reading in my sexretary? 

Lilith turned to Victoria, “I’m not sure. Is it a problem?”

“Not for any of us,” Kyrsten said. 

“Really? How can you say that? You’re dressed like… sluts for him… and he’s married, Kyrsten… Married with a baby on the way?”

“I’m not going to steal him from Carly. I want to join them. I love her almost as much as I love Jay. And Victoria’s no different. As for dressing like this… well…,” she stepped towards the golden haired beauty, standing just an inch or two closer than was necessary, “Sometimes a girl likes to be seen as a slut. Doesn’t she?”

“What? Uhhmm… no… I would never…” the doctor stammered, taking a step backward only to bump into the wall.

Victoria, finally finding her voice, said, “I used to think that. I was raised to think that a man should respect and cherish his wife… But Jay has shown me that respect doesn’t always involve being treated… nicely.”

Lilith’s eyes widened again, “What…. What do you… what do you mean?”

Victoria smiled. It was an almost sinister smile. A look I hadn’t seen on her before. Her eyes flicked to me for just a moment. Just a quick check before she turned her attention back to the prey she now seemed to be stalking. “Well… I always dreamed of a man making love to me. Whispering into my ear how much he loved me and how I was the only one for him as he slowly had sex with me with him on top.” She stepped forward and Kyrsten gave way, allowing Victoria to approach the trapped doctor who stood paralyzed against the wall. “Instead, what I got was Jay dominating me. He made me beg. He made me admit I was a slut. He didn’t ask. He demanded. And you know what?”

“What?” Lilith whispered so softly it was barely audible across the room.

“It was soooo much better than I’d ever imagined. He still treats us like princesses every now and then. But usually he treats us like sluts. Sometimes even like cheap pieces of fuck meat. And we love it. We crave it.”

Kyrsten and Carly were nodding. Lilith just looked completely shell-shocked. I cleared my throat, “We should allow our guest a few moments to compose herself. We have a dinner to eat.”

Victoria instantly spun around and walked over to me. She put her hands up behind her head and spread her legs a little more than shoulder width apart. It was the position I’d taught her the first time I’d fucked her. A position I’d made her perform a number of times in the office as I’d inspected her. I leaned forward and whispered into her ear loud enough for Lilith to hear, “Are you wet, slut?”

“Yes, Master,” she said.

I reached up her dress and trailed my fingers along her thigh, teasing her as I went. I stared at Lilith who stood as if hypnotized by the sight. My fingers found the soft, wet folds of Victoria’s cunt. They were, indeed, soaking. I slid my fingers into her eliciting a pleasurable moan from the brunette. “Very good,” I said as I pulled my fingers away. I held them up to Victoria who obediently licked them clean. Lilith shuddered as she watched, obviously aroused by the scene unfolding before her. “Now go bring dinner to the dining room. Kyrsten and I have a guest to entertain.”

“Of course, boss,” she said and scampered off to join Carly in the kitchen.

I turned to Lilith and gestured through the doorway to the dining room with my right hand as my left took Kyrsten’s outstretched fingers. “I know it’s a bit… unconventional… but it works for us. Now come join us for dinner, Doctor Shadam.”

She followed us into the dining room. There wasn’t much in there yet. An eclectic assortment of chairs we’d cobbled together from my apartment and Carly’s. A small table, barely big enough for four people despite the large room. No paintings on the walls. It was a dining room more appropriate for a 23 year old recent college graduate rather than 29 year old millionaires. Lilith noticed and couldn’t help but laugh a little. It defused some of the pent up tension that had been building for the last five minutes.

“I know,” Kyrsten said in a friendly tone, “It’s kind of sad. Carly and Jay aren’t exactly ‘fancy’ people. It’s not in them. If I didn’t move in they’d probably keep it just like this forever.”

Lilith laughed and I said, “Hey! What’s wrong with this room?”

Carly walked in just then, holding a platter of fruits and vegetables. “Nothing is wrong with this room, Master. It’s just the way you want it so it’s perfect by definition.”

I looked up at Carly as she leaned over to place the platter on the table. She kept her knees straight and bent at the hips deeper than strictly necessary. The stance gave me an eyeful of the smooth, moist slit between her legs. I reached up, casually tracing my fingers along her pussy lips. She stood there, staring at Lilith. Her perky little tits on full display while I casually fingered her. Some of that just defused sexual tension was starting to return. 

Kyrsten continued casually, “Nothing’s WRONG with it. But look around. You have this tiny little table and this huge dining room. Look at it this way, Master. Soon you’ll have four women living with you and at least one baby. Plus however many other sluts like the doctor you bring here to seduce.”

“What?” Lilith said.

“Oh please. Don’t play coy, Lilith,” Kyrsten said with a smirk. “You knew what you were getting into the minute you saw how we were dressed.”

“I… I… I didn’t…”

“Didn’t what? Think that our Master was going to try to make you another one of his sluts tonight?” Kyrsten said, leaning in closer. “You knew. And you’re still here. Which means you’re at least partially willing to be his slut. If not outright eager.”

“I… I’m not eager,” she said defensively.

“Okay… so willing it is then,” Kyrsten said, leaning back and folding her arms in triumph. Lilith looked shocked and opened and closed her mouth a couple times, unable to come up with a worthy response. 

The whole time this interaction was going on my fingers were worming their way into Carly’s hole. She was now rocking back and forth, wiggling her ass back against my hand and content to enjoy the teasing. I gave my fingers an aggressive wiggle inside of her, causing her knees to buckled slightly as she collapsed down onto the glass top table with a moan. “I enjoy catering to the fetishes of my women, Doctor. Carly wants me to bed other women. So I do that… for her. Isn’t that right, my love?”

“Yessss, Master,” she hissed as my fingers worked relentlessly on her.

“Others, like Kyrsten, just like having the freedom and safety to let themselves go. Or Victoria who has very traditional views of marriage and relationships but is learning that there are ways to be traditional without exactly being… you know… traditional.” I pulled my fingers out of Carly and gave her ass a firm smack. “Now off with you you silly slut. Is this all too much for you, Doctor?”

I hadn’t meant it to sound condescending. Truly. I was trying to be courteous and give her an out in case this really was more than she was prepared to jump in to. Her reaction was, however, entirely unexpected. She rolled her eyes and bit her lip before stammering out. “I’m a d… doctor. Of course I understand what you’re saying.”

“I didn’t me…” I started to say by way of apology but, fortunately, Kyrsten was quicker on the pickup. 

“Really? Are you sure you understand? You seem a little slow on the uptake, Doc.”

“Kyrsten?” I said but something about the look she shot me made my admonition die in my mouth. She had the mischievous look that she and Carly often got. That look that said they sensed something. 

“Seriously, Doc. What do you think is happening here?”

“I… I think… I think you guys are a little kinky…” she said. Victoria walked out with a plateful of pasta and set it down on the table silently. For a moment, the sound of her boots striking the marble floor echoed through the house, the only sound breaking the silence.

Kyrsten looked at Lilith, eyes searching before she slowly said, “Are you an idiot, Doc?”

“Wh… what?” she said. But again, I noticed she bit her lip and looked away. Was she turned on?

“Are. You. An. Idiot?” Kyrsten said with slow, deliberate words. Now I was watching the doctor and I saw the impact the words were having on her. I saw the tell tale signs of her skin getting flush. Her nipples poking out. Her breath taking short, sharp gasps.

“Nnnn… no?”

“Is that a fucking question? Are you actually not sure if you’ve got a fucking brain in your head?” Kyrsten asked with a condescending laugh. “Master, I think this dumb cunt is too fucking stupid for you. She probably doesn’t even know what her holes are for.”

The sound that came from the blonde woman caught me by surprise. It was a pitiful little yelp. A plaintiff whine that sounded almost forlorn. “Nooo,” she managed as she sat there and fidgeted.

“No what? No you’re not a complete moron? No you’re not an empty headed bimbo? You can’t possibly think you’re smart enough for Master’s cock, Lily.”

The diminutive name seemed to strike a chord with the blonde doctor. “D...d...d… don’t call me that,” she implored. 

“Ahh… does the dumb blonde bimbo have a probably with the name Lily? Maybe Lil Doc is better. Do you like that better, slut?” Kyrsten said. 

Finally understanding the game, I stepped in. “Stop being so mean to our guest, Kyrsten.” Kyrsten looked at me and started to say something but I shook my head slightly and smiled. I turned my attention to the Doctor sitting across from me. She looked almost disappointed. Which is exactly what I expected so I continued, “She’s not intelligent enough to comprehend your verbiage.”

Lilith’s eyes rolled and she opened her mouth to take in a little breath. “What?” she managed to whisper as her voice caught. 

“Sorry… those are some pretty complicated middle school words. “She’s too dumb to understand you, Kyrsten.”

Lilith fully moaned this time. She wasn’t hiding her arousal. I’m not sure if she could. 

“In fact, I think she might be too stupid to even understand how to eat her food properly. She’ll probably just end up ruining that nice dress which would be a shame. Take off your dress, Lily.” I stated in a completely matter of fact way. 

“But…”

“Sorry… did you not understand?” I asked coldly.

“No… I mean yes… but… it’s just…” she stammered.

“Then do what I’m telling you to. Stop trying to be smart. You’re obviously not able to do that. So just do what you’re told, bitch.”

You could almost see the fight flow out of her. Her resistance melted. Her arousal took over. She stood up and slowly stripped out of her dress, revealing the expensive, lacy underwear underneath. She was standing there while Victoria, Kyrsten and I watched, wearing only a sheer g-string and a black lace front snap bra. Her full breasts filled out the bra well and her long, straight blonde hair hung like spun gold across the impressive mounds of flesh. My eyes traveled down, taking in her flat, feminine stomach and well toned legs. She looked fit but not muscled. Demure but strong. 

Kyrsten said, “Pretty slutty underwear for a housewarming party. Were you trying to fuck me tonight, Lil Doc?”

“What? No,” she protested. 

Her denial seemed truthful. “Why the sexy underwear then?” I asked, genuinely curious.

“It… it makes me feel… you know… sexy,” she said.

“Take them off,” I said. The silence drug out in the room. Only Lilith’s labored breathing and the occasional clink of silverware from the kitchen could be heard. I could see the wheels turning in her head. The conflict between panic and arousal. Between lust and fear. Her eyes danced around the room, briefly settling on Kyrsten who gave her the barest of nods and a thin smile. “This is a safe place to play,” she seemed to be saying. Finally, with delicate, trembling fingers, she reached behind her and undid her bra, allowing it to drop to the floor. Her breasts bounced free as they dropped, full and firm, against her chest. Then she looked at me as she hooked her thumbs into her gauzy black panties. She met my gaze for a moment before looking away and peeling them off her slender hips. “Now sit down and eat your dinner, slut. Try not to make too much of a mess,” I said.

“Okay,” she replied meekly as she sat down again. Victoria came over and grabbed the linen napkin, flicking it open and laying it down on the naked woman’s lap. Lilith flushed crimson again at the gesture but picked up her fork and started eating daintily. 

“Where’d you go to school?” I asked casually. Kyrsten shot me a little grin and I returned it. I’d almost forgotten how much fun it was to play with a new toy.

“Duke for undergrad and Johns Hopkins for medical school.”

“Good schools. I bet you always felt like you didn’t belong with all those smart people though.”

She looked at me and I could see the twinkle in her eyes. It’s called Imposter Syndrome. It’s very common with smart people. Particularly women. Accomplished women in particular. She nodded to me and let out a sigh. “I learned to fake being smart.”

“But you’re not, are you. You’re kind of an idiot,” I said. She shuddered again and nodded. “And now you’re sitting here completely naked and the one man in the room isn’t even fucking you. So you’re not even very good at being a slut, are you?”

Her eyes widened and she bit her lip again before looking down and taking another bite, “I… I guess not.”

“She’s pretty enough, I guess,” I said to Kyrsten, “But I wonder if she’s worth my time.”

“You’ll never know until you try, Master. Maybe her cunt is useless but you’ll find her ass especially tight or something. Surely she’ll have some value hidden away in one of her holes.”

“What about it, slut? Which hole are you most accomplished with?”

“Uhhmmm… I don’t know, sir.”

“Master you dumb cunt. Master,” Kyrsten said, snapping her fingers to get the doctor’s attention. 

“Sorry… Master.”

“Well, which hole have your past boyfriends enjoyed fucking the most?”

“They… they haven’t, Master.”

“You’re a virgin?” I asked incredulously. I’d gotten the impression that her boyfriend lived with her based on the overheard conversation at her office. 

“No… No. Just… I’ve only had three boyfriends and none of them seemed to… to… uhhh…”

“They didn’t like fucking you?” Kyrsten asked, clearly surprised. As fun as the game was to play, the good Doctor was absolutely smoking hot and obviously a very sexual creature. Who wouldn’t enjoy fucking this beauty immensely.

“Uhmm… No. They didn’t,” she stammered, still eating her food between words and avoiding eye contact.

“I guess I’ll just have to sample all of her holes and make my own decision. Hopefully she has some worth. Otherwise I’m just wasting this spaghetti,” I said. 

“PPp… Please, Mr. Simpson… I… I want… Will you help me be useful, please?”

“We’ll see,” I said. We finished dinner, making chit chat and occasionally hurling a casual insult at our guest. I was still trying to feel her out. To figure out what it was that made her motor rev the most. Insulting her intelligence was the biggest thing, getting a visceral reaction with each insult thrown. By the time we’d finished our meal, I had a pretty good handle on what it was that made her tick. “Victoria, bring Kyrsten and I a bowl of ice cream.”

“Anything for your guest, Mr. S?”

“Not yet. We’ve wasted enough money on her for the moment.”

“Spaghetti is pretty cheap, Master,” Kyrsten said, laying her fingers on my arm as she watched Lilith’s reaction.

“She hasn’t shown me she’s worth even that,” I said coldly. Lilith shuddered again at my words. Her free breasts shaking gently and her nipples remained rock hard. “She can finger her worthless empty cunt while we eat. Maybe she’ll eventually inspire some small amount of lust in me.”

She didn’t need to be told twice. Lilith leaned back in her chair and spread her legs over the arms. The thin blonde tuft of hair above the wet pink slit looked dainty and delicate. It contrasted nicely to the look of wanton freedom writ large across her face. Her eyes were glassy, barely showing an awareness of the other two people watching her. Kyrsten and I watched her while we ate, making small comments as if we were clinically appraising her performance.

“Does she seem wet enough?”

“Maybe. We’ll check.”

Her legs aren’t spread very wide, are they?” I asked. Lilith immediately flexed her already wide spread legs further. 

“That’s better. She’s not the most flexible bitch you’ve fucked though.”

“No… probably not. I miss Louise, you know. I could really double her over and pound her hard.”

“Hrmm… she is nice. Do you think this bitch will be as tight as Louise?”

“Probably not. If she were they probably wouldn’t have dumped her ass. I bet she’s a real cold fish in bed. Don’t you think that’s it?”

“Maybe. She probably can’t deep throat, that’s for sure. Hey slut, ever taken it in the ass?” Kyrsten asked.

“N… No,” she stammered.

“Figures. Prissy bitch like her isn’t even sexy enough to get a guy to fuck her ass. Maybe that hole will be tight enough to get you off, Master?”

“It’s a good thought. She certainly hasn’t earned my cock in her cunt yet. Come over here, whore,” I said. She reluctantly pulled her fingers from her pussy and stood up. “Crawl like a good little bitch,” I said. She stopped and looked at me then sank to the ground and crawled around the table to me. “Beg for it, slut,” I said as she looked up at me from her knees.

She didn’t hesitate, “Please fuck my ass and make me useful, Master. You can defile me in any way you want. I just want to be desirable to someone. Let me be a slut for you. Please?”

I ran my fingers through her hair as I looked at her delicate features. So  incongruous from the filthy things she was asking to have done to her. I grabbed her hair firmly, “You’re a pathetic, worthless waste of femine flesh, aren’t you?”

She nodded, “Yes, Master. And you saw it so quickly it must be true.”

“That’s right, slut. All of us saw it. We all realized from the moment we laid eyes on you that your only value was as a piece of fuck meat. And even that only after lots and lots of training.” It wasn’t true, of course. She’d seemed perfectly normal and vanilla when we’d met in the office. It had taken Kyrsten’s observant eye to recognize what the lovely Doctor’s kink was. Nevertheless, she was practically panting at the words as she looked up at me. 

“Yes… that’s what I want. Train me to be useful… please?”

“Come with me,” I said as I picked her up by her hair and practically dragged her to the sliding glass door that led out to the pool deck. I slid it open and walked her over to one of the lounge chairs on the patio. I looked around for a moment. The calm night air contrasted starkly to the roaring gusts this morning. An evil thought crossed my mind as I pushed her forward onto the chair. “Here’s how you’re going to show me you’re not a useless little cunt. I’m going to fuck your ass right here. We have three neighbors. If one of them doesn’t come complain to me tomorrow about your noise, you’re never coming back, understand?”

“Yes… yess… please… I’ll scream so fucking loud. Pound my ass please. Let me show you I can make you cum. I promise I will… please,” she said loudly.

Kyrsten walked up next to me as Carly and Victoria followed behind. “I’m so fucking hot right now, Master,” she whispered to me. “Have I been a good wingwoman tonight?”

“Oh yeah,” I said. I kissed Kyrsten and felt her tongue dance needfully inside my mouth. While we kissed, Victoria dropped to her knees and started lubing up my cock. I broke the kiss and looked down at the dusky straight hair of the busty brunette on her knees in front of me. “And you’ve been a very good assistant,” I said. She looked up at me and winked before planting a gentle kiss on my cock. Meanwhile, Carly had positioned herself beside the Doctor and was holding her ass spread wide for me. I stepped forward and Carly guided me against Lilith’s tightest hole. I leaned forward, easing the head into her ass. 

“Ohhhhh…. Fuck… yessss… You’re in my ass… Oh yesss,” she wailed. 

“I was louder than this dumb slut this morning wasn’t I?” Victoria asked innocently. 

“Definitely,” Carly and Kyrsten agreed in stereo before giggling. Lilith, spurred on by the ridicule, screamed even louder, narrating every action. Every thrust. Every smack of our flesh. She would alternate between incoherent wailing and dirty, filthy talk that would have made a sailor’s whore blush. 

“Your big fucking cock is impailing me… oh God… my filthy slut… fuck me… my filthy slut ass… Yess… yess… So fucking good. Fill me… use me… fucking hurt me. Fuckfuckfuck.” As remote as our neighbors were, I started to think she might actually succeed in the Sisyphussian task I’d laid out for her. She was DEFINITELY being louder than Victoria at this point. Even her grunts were high pitched squeals. 

I gripped her hair and wrapped it around my hand, jerking her head back and forcing her to arch her back sharply. “You call that loud, whore?” I slowly pulled my cock out of her ass and held it there, just the tip inside her as I felt her grip and squeeze me. “Maybe you don’t even deserve an ass rape tonight, bitch.”

She started sobbing, “No… please… I’ll do anything. Please. Just use my ass. Please,” she whined. She sounded so pitiful and broken I was both aroused and a little concerned. A small corner of my mind was bothered by my reaction but she continued before I could fully process the moment, “Please… please… I just need to be useful. Please!”

I flung her forward on the chair and smacked her ass hard. “You want this?” I snarled.

“Yessssssss!” she screamed as I eased into her again, filling her up. She gripped me like a red hot vice, trying to trap my shaft with will power alone. I pulled out and slammed back in three more times, driving her face into the chair without mercy or compassion. Her finger strumming on her clit went into overdrive and she started cumming hard, “Thank you! Thank you!!” she screamed into the quiet dark of the night. I fucked her steadily through her orgasm as she kept babbling, “Please cum… please cum… please cum.” I didn’t need the request and instead gave her another couple thrusts and pulled out, shooting my cum all over her back and hair. The load was so huge that Carly gasped as the globs dripped out of her hair and down her neck. Lilith was panting, desperate for oxygen as she whispered a quiet question, “Was I useful, Master?”

Leaning forward, I placed a single small kiss at the small of her back. “Yes you were. But you were useful before this, Lilith.”

The sobbing from before returned. Momentarily, I was concerned I’d said something wrong but she squeaked out a forlorn, “Thank you.”

“I like playing games with hot girls, Lilith. I don’t like doing damage.”

She looked over her shoulder at me and I saw her eyes sparkle, “That’s the sweetest thing anyone’s ever said to me after fucking me in the ass.”

I laughed, “That’s a low bar since you were an anal virgin twenty minutes ago.”

“It’s probably the sweetest thing anyone’s said to me in a long time, actually.” The sadness was back in her eyes. I had flashbacks to Starla. To Louise. To Kyrsten. To all the girls that had so much hurt in their past and the minefields towards intimacy it created. “I hope you get lots of complaints from your neighbors… Master?”

Little did she know but complaints weren’t the interactions that I got.