Carly's Wmaf Fantasy

I can't believe I've done 20 chapters of this story and still have so much more to go. Thanks again for the words of encouragement. The comments (both public and private) are super encouraging and I love the ideas (even the ones I don't incorporate). I don't know if there's another 20 to go but we'll see.

*****

I woke up the next day to a short text message pinging on my phone.

Louise: I had a wonderful time last night. It wasn't what I expected. Thanks.

I smiled to myself, grateful that we'd hit it off. It was weird texting back as I had that sort of excited nervousness you get when you're in the early days of a relationship. I hadn't felt that feeling in a long time. Not since Sasha, I guess. Things had happened too quickly with Carly and Kyrsten and I hadn't even been aware of the escalation in my feelings. It was different with Louise.

Me: It was wonderful for me as well. Can I see you again? Maybe Tonight?

Louise: Mr. S. So eager! Don't you have plenty of female company?

Me: I'm one or two short ;)

Louise: Tonight it is. But remember... I'm a good girl 😘😏😇😇😇😈

When I set my phone down, I glanced over at my sleeping fiance. Her long black hair cascaded down her naked back as she lay sprawled across my bed. She was softly snoring on her stomach and I stroked my fingers down her spine, tracing the ridge with a gentle stroke. She sputtered something groggily in her sleep, but otherwise didn't move as I stood to get dressed.

I wrote her a short note with some instructions and left for work.

Just as the day before, Victoria was completely professional at the office. She'd dressed much more appropriately, wearing a tight, form fitting but full-coverage dress that was both breathtaking and oddly conservative. The material was soft and thick but I could just barely make out the outlines of the garter belt she was wearing underneath. Lunch arrived quickly and I ordered a salad for Victoria and I. It wasn't uncommon for us to have working lunches but this one had an air of sexual tension to it that was almost tangible.

"Did you enjoy yesterday?" I asked, watching the beautiful, curvy brunette as she daintily ate her meal.

"Yes, Sir. Very much," she said with a twinkle in her eye.

"Did you think that your first time would be like that?"

"I... No... I didn't. And, truthfully, I'd have been appalled if you'd told me that was how my first time would be when I was in high school."

"I realized I don't really know much about you, Victoria. You're 25, right?"

"Yes, Sir. I was born in South Carolina but my Dad was military and we moved around quite a bit. Ended up at Norfolk for awhile before Dad got a teaching job in Annapolis. I did my four years in the Navy but I knew it wasn't for me."

"You were in the Navy?"

"Yes, Sir. Is that surprising? Did you not remember that from my resume?"

"I guess I was too busy trying not to mentally undress you."

She laughed but then frowned, "I know that's not true. You barely noticed me until recently."

"Sorry... I had a girlfriend at the time," I said.

"Yeah, you definitely can't go hitting on cute girls when you have a girlfriend," she said mischievously.

We laughed, "I don't know. Until Carly, I really didn't look at women so..."

"Lecherously?" she asked with a smile.

"How about... aggressively," I said. I put my hand on her knee and slid her dress up, revealing the garter belt underneath. And also showing a smooth, shaved, unobstructed cunt glistening with moisture.

"I like aggressive, Mr. S," she said. I kissed her softly, tasting the sweet lips that tenderly reciprocated. Compared to the soul shattering kisses that Carly laid on me, or the eager, not so subtle promises that Louise's lips and tongue had made the night before, this was so different. This kiss promised devotion and submission. Nothing more. Nothing less. She surrendered herself into me with a sigh.

As I pulled away, she didn't complain and whine. Victoria simply smoothed her skirt and said, "Thank you. When will we be able to meet up after work again? I really would like to but I'm not pressing. I know you are very busy... uhmm... juggling."

"I've got a commitment tonight. I'm taking Carly's little sister to get a tattoo. And then a date with her roommate."

She laughed again, "OOoh... what kind of tattoo?"

I paused. It wasn't exactly the kind of tattoo you told people about. But I'd already decided that I was going to embrace honesty in my relationships. When things were as complicated as I'd managed to make them, further adding complexity with layers of falsehood just felt like a bad idea. "It's a tattoo to mark her submission."

"You're sleeping with your fiance's sister?" I nodded and she asked, "Got a bit of yellow fever, Mr. S?"

"What? No... it's just..." I noticed she was smirking at me and I relaxed, "They both manage to push my buttons."

"By being submissive?"

"Yes, actually."

"And getting tattoos? You find that sexy?"

"On some girls..." I said with caution.

"What about me? If you saw a tattoo on me, what would you think?"

I paused, "I've already seen that you don't have one."

"What would you think though? What if you saw a good, Christian girl like me with a tattoo right here?" she said and she traced a line from the outside of her breast down to the top of her hips. I tried to imagine it.

"What would it be of?"

"My favorite bible verse," she said, "Song of Solomon seven, ten. 'I belong to my love and his desire is for me.' "

"I think I'd like that?"

"Is that better or worse than my second favorite verse on the small of my back?"

I laughed, "What would that be?"

"My beloved thrusts his hand through the hole and my bowels are moved for him," she said with an absolutely wicked smile.

"That can't be real," I said incredulously.

"Song of Solomon five, four," she said holding up her fingers in the "Scout's Honor" sign. "So which is hotter, Mr. S?"

"Uhh... both... I don't know... they're both... uhmm... yeah," I said, feeling the heat in the room. What was with the girls leaving me flustered today?

"Hrmm... I'll think about it. Can I come tonight and make a decision later?"

"Wait... you want to get a tattoo tonight? That's a little quick, Victoria," I cautioned. Despite knowing her for several years, I couldn't help but feel like the little warning klaxon at the back of my mind was firing off.

"I'm sure it feels like that to you but I've been thinking about this my whole life and I've been thinking about you for the last two years. I know all that I need to know. Besides, it's not like I'm getting something like, 'Jay's Sex Slave' or something."

She was surprisingly close with what I had planned for Sherry. But she was right. A tattoo like she described wasn't actually that big a deal in the abstract. She wasn't getting my face on her back or anything. Just a verse from the most popular book on Earth. I nodded and she grinned.

"Thank you, Mr. S. You'll love it. I'm sure," she whispered huskily.

"I think I need a little relief, Victoria. Get under my desk," I said and she eagerly obeyed. Her technique wasn't flawless like several of my other girls but that was to be expected. What she lacked in inexperience she attempted to make up for in enthusiasm and attention to detail. I watched her study me, taking the shaft into her mouth slowly and carefully. Listening to my breathing and testing my reaction. "Good girl," I told her and she cooed softly, emboldened by the encouragement. I snapped a quick picture of her and texted it to Carly.

Me: You were right about Victoria.

Carly: Your cock looks so big in her tiny little mouth, Master.

Her reply came so quickly that I was sure she was watching or reading something on her phone when I texted. Curiosity evaporated from my mind, however, as Victoria sunk down on my cock again, pushing into the back of her throat. She sputtered and coughed, pulling off my cock with a small frown of disappointment. "It takes time to learn to deep throat. You'll get there," I said encouragingly. She nodded and wiped the spit from her face, smearing her lipstick slightly before resuming her task. Inspiration struck me and I gestured for her to continue while I picked up my phone. "Daphne? Hey. Can you come down here for a minute please?"

Dave's assistant and my personal office fuck toy sauntered in a few minutes later. She was dressed to kill with a tight, short black dress that was very close to a sexy cocktail dress. She always dressed that way at the office. She figured out exactly where the line was and made sure to stand directly on it... sometimes even metaphorically leaning over. That was what she was doing today. She walked in and paused for a moment, seeing the young woman sucking my cock under my glass topped desk. She couldn't recognize Victoria from that position and it amused me to watch her try to figure out who it was.

"Yes, Sir?" she asked, hands behind her back and tits poking out. "What can I do for you?"

"Let's have a race. If you cum before I do, I'll give you Friday off. If you cum after I do, you owe me a favor."

"What kind of favor?" she asked, already pulling up her dress and displaying her smooth, exposed cunt.

"Don't worry... you'll like it. But it'll be an all weekend kind of favor and you'll be very tired afterwards."

She nodded and smiled before flopping down on the chair and draping a leg over the edge. For the next couple minutes, not much was said and only the heavy breathing in the room broke the silence. Victoria, inspired by the challenge, really started working hard, sliding her tongue over my cock. Daphne was even more motivated and worked hard herself, stroking her clit and pinching her nipple through her dress lightly.

Despite Victoria's inexperience, the lewdness of Daphne's actions was a hell of a visual stimulant. When Daphne dipped her finger into her gaping cunt and moaned softly, it sent me over the edge and I erupted into Victoria's hungry, inexperienced mouth. To her credit, she didn't sputter this time, having readied herself. She sucked the cum out of my cock like it was her favorite dessert, murmuring happily as she caused me to nearly black out from sensory overload.

"You can stop, Daphne. You lost," I said firmly. Daphne looked incredulously at me then hung her head submissively. The blonde remained a bit of an enigma to me. Defiant, ambitious and generally domineering. And yet somehow, with me, she was so obedient. She didn't eat and breathe submission like Carly. It didn't define her like Victoria. But it was still there. Under the surface. "Good girl, Daphne," I told her as she straightened her dress and smoothed the slightly rumpled front around her breasts. "You can cum tonight if you'd like. Now back to work with you. I'll let you know when I'm going to collect on that favor," I said. She gave Victoria one last curious look before departing without another word. The thought that she'd spend the rest of the day aroused and frustrated was very enticing all by itself.

I helped Victoria up. She still had a little cum on her lips which she daintily wiped off and slurped up happily. "That was surprisingly good, Mr. S. Best I've ever had... although I haven't had many."

I laughed, "How many men have you tasted the cum of you silly little slut?" I asked her, cupping her chin in my hand.

"Just one, Sir. Liam Davies. He was a cute exchange student who came over my senior year that I gave a hand job too."

"You've never sucked a cock before? At all?"

She shook her head and I continued, "Well that was pretty great for a first time. You should be proud." She stood up straighter and smiled happily. "Now go get your face cleaned up. I can't have my secretary looking like a used whore out there, can I?"

"No, Sir. Thank you, Sir. I enjoyed that."

"You enjoyed being watched while you serviced me? While you sucked my cock like a greedy slut?" I asked and she nodded, shuddering slightly. "Good. I'll be sure to let you show off your talent to my other women as you improve."

"Thank you, Mr. S. I knew I could count on you," she said and scampered off, presumably to the restroom to fix her ruined lipstick.

After work, I escorted Victoria down to a cab and over to Goddard Hall. She was quiet, alternating between picking at her clothes and looking out the window. "You okay?" I asked softly.

She looked at me and smiled a tight smile before tucking her hair behind her ear. "Just in my head," she said.

"About meeting the girls?"

"Yeah... and, you know, getting into a pretty weird lifestyle."

"Was that lunchtime encounter too much?"

She put her soft hand on mine, "No... No, definitely not. That was hot, Sir. It's just... I wonder about the dynamic with the girls. You have to be spread pretty thin and I see you so much more than the rest of them. Will they be jealous? Angry? Territorial?"

"The girls aren't like that," I said, trying to reassure her.

"Girls can be pretty catty and bitchy, in my experience, Mr. S."

"Some girls can. Especially Sherry that you'll meet today. But we've found a good equilibrium and I'm sure you'll find how you fit in."

She nodded uncertainly and looked back out the window. I stroked her back and she shivered, "You sure about getting a tattoo. It wasn't my intention..."

"Definitely, Sir. I love the idea and thought about doing it before."

"Good," I said. We went upstairs, drawing stares as usual. When I knocked on the door, it swung open to reveal Starla and Louise standing there in their tight little yoga shorts and sports bras. While the two were built completely differently, I wasn't sure, in that moment, which one I wanted more. Starla's huge tits strained at the bra that was fighting valiantly to hold back their weight. Louise, on the other hand, had the nice, tight, athletic body that made you wonder what she was like in bed. I realized, not for the first time, that I was definitely going to fuck her. And soon.

"Hey, Mr. S," Louise said.

"Hello girls. You both look very lovely. You heading out to tease boys or coming back from it?" I asked as I stepped inside. Starla had her eyes cast down, unable to meet my gaze.

"We're headed out now. It's leg day so we'll have ALL the boys watching today," Louise said with a big grin. What a delicious little cock tease she was! I watched as the two girls walked out, both shaking their asses with the knowledge that my eyes were glued to those beautiful buttocks.

"You certainly do have a way with women, Sir. They're very pretty," Victoria said. I glanced at her, noting her deadpan "secretary" voice. She caught my eye and silently answered my question with a not so subtle lick of her lips. "VERY pretty," she repeated with much more emotion. I grabbed her hand and pulled her to me, giving her a thorough kiss.

"She's not the only pretty one. Plus Carly's sister is smokin hot too." I smirked at her and gave her a little smack on her ass causing her to jump and yelp.

The bedroom door opened and Sherry walked out, unaware of our presence. She was wrapped in a short towel, apparently having just gotten out of the shower. She was drying off her hair and humming some terrible k-pop song when Victoria cleared her throat. Sherry must have jumped halfway to the ceiling and screamed. When she saw me grinning at her, she calmed down, "You scared me, Master. I was just getting..." she rambled but I cut her off with a raise of my hand.

"Drop the towel you dumb cunt," I said harshly. The change in her was instantaneous. Where she'd been normal and casual a moment before, now she was in submissive slut mode. She paused for the briefest of moments, questing eyes flicking over to Victoria before shrugging the towel off. Her body was just as hot as I remembered, smooth skin and big, firm tits made her ridiculous hourglass proportions the third hottest thing about her. She stood there, slightly shaking from the cool air on her still damp skin. Her long hard nipples stood out proudly making the shining dumbbell piercing all the more prominent. "You're getting the rest of your decorations tonight, slut."

"Yes, Master," she said with utter servitude.

"Did you have plans tonight?"

"Hideo was taking me to dinner, Master," she said.

"Hrmm... On your knees," I told her and she dropped swiftly down and looked up at me.

"How long has it been since you've had an orgasm?"

"Weeks, Master," she said. The utter despair in her voice made my cock ache. I fished it out and shoved it down her throat, listening to Victoria's gasp of surprise as the small Asian girl took the full length down her throat easily.

"Sherry is the most pathetic of my sluts, Victoria. Pretty much the lowest of the low as far as I'm concerned."

"Did she mean Hideo from the office, Mr. S?"

"Oh... yeah... I hooked them up awhile ago. But she's not allowed to do anything with him without permission. And I haven't given it," I yanked Sherry off my cock and snapped at her, "Have you kept your holes empty for me, bitch?"

"Of course, Master. Hideo doesn't even ask anymore. He knows I'm not for him."

"Good girl," I said and slammed her back down on my cock causing her to hum in content satisfaction. I took my phone out and snapped a couple of pictures before texting them to Hideo.

Me: I'm taking Sherry out tonight. She'll need some comfort when I'm done with her so you can wait here tonight for her.

I didn't wait for a response, instead roughly fucking Sherry's accomodating throat brutally. Victoria had reached up under her dress and was teasing herself gently as she watched. "You like watching, baby?" I asked. She nodded as I kept pounding the kneeling slut at my feet. "My work wife watching me fuck my fiance's little sister?" She nodded again, dipping her fingers into her leaking cunt before strumming her clit rapidly. "Don't cum, slut," I warned her and she nodded. We continued to stare into each other's eyes as I took my pleasure from Sherry's willing mouth. She knew she was an object to me in that moment. We all knew and, I think, we all were getting off on it.

As I felt my orgasm approach, I realized that age old conundrum was creeping up on me. Where to cum. I decided to see if I could bring Victoria into it.

"Where should I cum, baby?" I asked her. Sherry couldn't tell who I was talking to and murmured something on my cock which just made me gag her more viciously.

"In her mouth, Sir?"

I shook my head, "She's not good enough to earn my cum in her mouth. Think worse."

"On her tits, Sir?" she said stroking her clit faster.

"Worse," I said.

"... On... her face... sir?" she said in a whisper.

"That's an excellent idea. But what should she do after I paint her slutty yellow face with all this cum?"

"She shouldn't wash it, Sir..."

"Why?"

Her fingers danced across her clit faster, "She's a slut, Sir. A cheap slut," she said.

"Aren't you a slut, Victoria?"

Her eyes grew wide, "Yes." Her voice was quiet but her arousal could not have been more evident.

"So then I should cum on your face, don't you think?"

She gasped but immediately dropped to her knees on Sherry's right side. "Yes, Sir. Please paint my slut face with your cum. Make me pretty for you. I'll wear it proudly so everyone knows what I am, Mr. S."

"Good girl," I said and I pulled my cock out. The first rope of cum sprayed over Sherry's wet hair before I quickly re-aimed it and coated Victoria's face. She reveled in it as blast after blast covered her. "Cum for me, slut," I told her.

"Yessss," she said and shot off, cumming hard and collapsing on the floor. Sherry sat on her heels, watching the wanton display of my new toy. Her fingers were resting on her thighs, twitching in arousal. The white strand of cum was obvious as it sat on her silky black hair. I shoved my cock back down Sherry's throat twice just to make sure all the cum was out before zipping up.