Carly's WMAF Fantasy Pt. 09

The rest of that first weekend went by as you'd expect. Lots of sex lots of talking. In fact, we ended up having so much sex that I had to send Sherry back to her dorm so she could get some studying done. Carly came back the next weekend and we enjoyed some time just the two of us. I wanted to bond with Carly as much as possible to find out exactly where this relationship was going. We spent nearly the whole weekend naked (or her wearing sexy underwear), teasing and flirting and fucking. By Sunday, we'd actually managed to fully exhaust ourselves and instead chose to lay on the couch and play some more 'League of Smiting Ancients'. I think she was starting to relax and enjoy showing off how good she was.

"Colonel Mizzix is terrible in this matchup," she said as she killed the stocky soldier for a fourth time in nearly as many minutes. We went back to our tower to buy. "Let's hide here and kill them again when they show back up. It'll leave them super tilted."

"Okay. Do I buy a Blazing Spear or an Emerald Chalice?"

"You need the Emerald Chalice first otherwise you'll have energy problems. But after we get this kill, you can probably buy the Spear outright."

It was fun to have a girlfriend that was not only into this but, if anything, might have been into it more than me. It obviously helped that this was HER game and she'd been on the ground floor of making it but that did nothing to take away from her enthusiasm. Sure enough, the other two players walked back exactly where she predicted them to and we killed them again. They were so far behind that we took three camps and then started to roam. The other team surrendered five minutes later. So far, we'd won every game we played and only one had gone past twenty minutes. I kind of didn't want to play without her because I knew, in my head, that I'd already probably outranked my actual skill. Plus, playing with Carly was super fun.

Unfortunately, her plane was leaving soon and we'd be apart for another week. I was bummed out pretty hard by that but I knew it was the short term reality. "Have you given any more thought to moving to the City?"

"Why does everyone who lives in New York call it that? The City? Boston is a pretty big city too you know."

"I don't know... it's actually more of a New Jersey thing. People that live across the bay call it that. I've just picked it up cause I work with a bunch of them. For all I know, they're mocking us." I smiled at Carly and she returned it with a beautiful toothy grin.

"I don't know, Jay... Master," I knew calling me Jay was her way of letting me know that she was talking seriously. "I've been thinking of moving out of Boston for awhile. The big city life is wearing on me. I think my quality of life would be a lot better somewhere less... busy." She tucked her hair behind her ear and looked away, afraid of what I was going to say.

"Carly... " I said and she turned back. I flicked between her eyes, trying to figure out what I was seeing. Fear? Apprehension? Sadness? "I'm not overly attached to NYC... It's just what's been home for me for five years. And the company's been really good to me."

"Say you could live anywhere. Anywhere at all. Don't think about money or a job. Where would you want to live?"

"The Keys. Easy," I said without hesitation. Carly's eyes lit up.

"Really? Oh I love it. That would be amazing!"

"Yeah but... I don't have the money yet to just up and leave. And together we probably could do it... but it's not like we'd find good jobs down there. I've got some savings but not enough to just say 'fuck it' to work."

"Jay, I'm the lead developer on a ridiculous hit of a game. I have options."

"Stock or life?" I asked with a smile.

"Both, I guess," she said with a giggle. "I think, between the two of us, we could buy a house anywhere we want and have enough to comfortably live off as long as we took ANY job... anything we wanted. Hell, I could do contract work online. And you wanted to write, didn't you?"

I ran my fingers through my hair, unsure of really what to think. "It's a lot. But it sure does sound like a good plan. I need to think about it."

"I know. And I'll wait for you to make a decision and no decision you make is going to change things between us. I love this and don't want to to ANYTHING you're uncomfortable with. I just want whatever we do to have the best chance possible for us."

"Isn't that usually the line that guys give girls?"

"Yeah, but it's usually about getting them to give up their ass. And you already got that so you're done being nice like that to me, right?"

"Damn straight, slut," I said as I reached over and yanked her face forward across my lap before spanking her tight little ass several times while she squirmed sweetly. "I wish I had time to properly fuck you."

"I'll get a later plane flight, Master," she offered, wiggly her butt at me enticingly.

"No. I don't want you getting home stupidly late or chancing missing a flight. I'm seriously going to miss you, babe."

"I know, Master. I... " she trailed off.

"Still not ready to tell me?"

"No, Master."

"Still committed to tell me if I ask?"

She looked away and paused, longer than the first time I'd asked her that. When she looked back at me I saw fear and love and complete devotion. "I will always tell you the truth, Master. No matter how scared I am."

"Good girl," I said and leaned in for a tender kiss, "Tell me when you're ready." I said and she simply nodded, looking away.

We gathered her things went to the airport, trying to squeeze every moment out of it that I could. Our hands were held in silence the whole way there, both of us thinking about different things. Or maybe the same thing. That's the nature of those intimate silences. You just never know.

After I watched her leave, I simply wanted to crawl into bed and sleep until next weekend. Was this depression? Loneliness? I just felt empty. And sad. I'd never had a girlfriend like Carly. In lots of ways, not just the sexy stuff. I was absolutely certain that she was who I wanted to be with.

Monday I was back to work, trying to take my mind off Carly when I saw Dave walk by. He'd been on a job site all last week so I hadn't had a chance to talk to him. "Hey, Dave. Come in here man."

He shuffled in and softly asked, "What's up?"

"Not much. I just saw Madison last weekend and she wanted me to talk to you about things. Explain em and what not."

He nodded his head, "She already told me. So I'm good."

"She told you about Carly and Sherry? What'd she say?"

"Carly and Sherry? Who are they."

I furrowed my brow, unsure of what was happening. "What did Madison say to you?"

"Do we have to talk about this here?" he asked as he looked around nervously.

"No... no of course not. Let's do lunch?"

"Sure... 11:30?"

"Yeah, I'll come by your office and we'll figure out where to go."

"Wherever you want, man," he said as he turned and left my office. I was confused but I understood his reluctance to talk about swinging with his smokin' hot wife while at the office. I went back to working on some accounts and finished up a couple small project reports before lunch rolled around. Grabbing my coat, I went down the hall and knocked on David's door. "I'm ready."

"You figure out a place to eat?" he asked, looking up from his spreadsheets.

"I'm good with that taco place down the street," I said as he stood up stiffly.

"Sounds good," he said. We walked in complete, awkward silence out of the office and down the elevator. Dave didn't say anything to me at all until we got to the restaurant and sat down. "So who are Sherry and Carly?"

"Carly's my girlfriend and Sherry's her sister. They're the girls I was shopping for with Madison at the store."

"Oh. Madison didn't really mention them," he said looking a little embarrassed.

"I don't understand. Who did you think we were swapping with?"

"Swapping?" he asked with genuine amusement. "Is that what you think Madison wants?" Oh Madison's gonna love that."

"What? No man, I didn't mean to offend you. I just thought... shit... please don't tell Madison. Just forget it, Dave. I had no intention of..."

"Nono... you've got it wrong. She's going to fuck you. She already told me. But no way is she letting me fuck someone. I like watching her with... you know... "

Realization dawned on me, "You're a cuckold?" I said a little too loudly. "You're a cuckold?" I said again whispering. Dave just nodded.

"Dude, I didn't realize. So all those times Madison flirted with me were totally for real?"

"She's been wanting to bang you for awhile, yeah," he said. Again, the embarrassment on his face evident.

It was my turn to laugh, "Oh that makes so much sense. Well you've got to meet Carly. She's just like you. She likes watching me. I already fucked one of our high school friends with her and her sister. And now it sounds like Madison too, huh?"

Dave swallowed and nodded, unable to form words. "Well that's cool man. And what do you like? Is it like you enjoy pimping her out? Or... is she the one in control."

Dave looked away. "It's all about her. I like how she torments me. And I like that she comes back to me."

"That's awesome man. Own it. Carly's been a lot happier since she got comfortable with her kinks."

Dave smiled at me, "Thanks. It's just... Well... this wasn't supposed to really overlap with work. That was kind of a rule. But Madison told me this was a rule she wanted to break years ago and... Seeing you with the girls this weekend. It got her thinking."

"So she's the boss, huh?" I said, intentionally needling him a little to see if that's what he wanted.

"Yeah. She's totally domineering in bed and out. That's what I love about her."

"We'll see. Tell her I'll be over Thursday night."

Dave just nodded. Apparently taking orders just came natural to him. I'd kind of noticed that about him. It's why he hadn't made partner at the firm. He worked hard, looked the part, had great ideas. He just didn't assert himself in meetings or in front of the clients. We were lucky to work for a company without a lot of internal politics. At a bigger company, someone would have stabbed him in the back or stolen all of his glory completely and he'd probably have spent the rest of his days as a lowly worker bee. At least here, he moved up the ranks a bit since people recognized his good qualities. He just didn't get as much credit as he probably deserved.

"Good, it's settled. Now, let's have lunch," I said with a smile. He relaxed visibly and I found myself really curious about the dynamic between him and Madison. It wasn't anything I was used to or, if I'm being honest, could even really understand. But he seemed to be happy, if somewhat nervous, about the arrangement and we didn't talk about it again that afternoon.

Later that night, I got a text from Madison though.

Madison to me: David said you talked to him. I'm so excited 😘🤭
Me: Me too. Though I didn't realize the situation with your husband...
Madison: He told me. It got me so hot that you made him explain it to you.
Me: How hot?
Madison: My little cucky husband is eating me right now.

She attached a picture of the top of Dave's head nestled between her legs

Me: Fuck that's hot. So you're the one who wears the pants in the family?
Madison: Fuck no. I'm far too slutty to wear pants. Lol.
Me: My kind of girl! 😈
Madison: I can't wait to ride that cock of yours.
Me: You'll have to earn it. I've been getting some good pussy lately.
Madison: I saw. A girlfriend, a complication and a convenience. What's that make me? 🤔
Me: Guess you'll have to wait and find out Thursday, slut.
Madison: Fucking tease. You know where we live. Come over now.
Me: Thursday.
Madison: Asshole 😋 I'm gonna take that out on David.
Me: Make his tongue so tired he can't talk tomorrow and I'll pound you extra hard Thursday.
Madison: Deal!

I switched over to Carly

Me to Carly: You awake?
Carly: Yes, Master.
Me: I'm going to fuck Dave's wife on Thursday.
Carly: My cunt just gushed. He agreed to the swap?
Me: Turns out he's a pathetic cuck like you, baby 😉
Carly: Oh that's hot.
Me: I'll let you know how it goes.
Carly: Are you going to fuck Sherry this week?
Me: Is that your business? Are you jealous?
Carly: No, Master. I just want to make sure all of your needs are met by the holes available to you.
Me: Such an obedient, attentive pet.
Carly: Thank you, Master. 😊 Nite
Me: Nite

I looked at Sherry's schedule that I'd jotted down. She had a lab tonight but nothing tomorrow afternoon.

Me to Sherry: Be at my unit tomorrow at 7pm. Dress like a trashy gutter slut. Make sure you're ready for whatever I want.
Sherry: Yes, Master. Thank you, Master.

I had a thought then.

Me: Actually, where do you live?
Her: On campus. Goddard Hall

She linked me the address

Her: Room 512
Me: I'll be there tomorrow at 7.
Her: My roommates will be here 😲😱
Me: So? Is that a problem, slut?
Her: No, Master 😔
Me: Edge tonight and be edging tomorrow until I get there.
Her: Thank you, Master.

With plans in motion, I realized it was going to be a terrific week. This was definitely the best way to fill a week. Fucking willing sluts and sharing it with Carly to get her hot and bothered for the weekend.

The next day, I made sure to go to Dave's office right away. Knocking on the open door, I asked, "How are you doing?"

Dave choked on his coffee before sputtering, "Fine."

"How's the tongue?" I asked.

He looked embarrassed but smiled, "Also fine."

"So you're looking forward to Thursday?"

"Yeah..."

"And it's cool with you. Nothing changes here?"

"No, sir," he said in mock salute. I was having a hard time getting a read on the guy. Anyone who looked at Dave would see a 6'2 ex college baseball player who kept himself in pretty good shape. But I'd seen a different side.

"Okay. Well we'll talk more later." I left his office and returned to mine. I was able to get through the day more easily than you'd think, mostly by keeping myself so busy that I couldn't think about the nubile asian co-ed lusting for my cock. Damnit... I remembered. Around 5:30, I left the office and practically sprinted downstairs to catch a train to close to Sherry's dorm. On the way, I texted Sherry.

Me to Sherry: OMW slut
Sherry: I'm so ready to get fucked, Master. My roommates are here though.
Me: Good, they'll get to hear what pathetic cunt they're living with.
Sherry: Yes, Master. I'm looking forward to everyone finding out what I truly am.

When I got to the dorm, Sherry was already waiting at the dorm entrance to sign me in. She greeted me with an emphatic kiss and whispered into my ear, "I'm so fucking wet, Master," as she stood on her toes so she could grind her pelvis into me. She was wearing a pair of short workout shorts and a sports bra. The piercing place had recommended that for someone with her size breasts and I'd been crystal clear with her the night before that she was to, in no way, risk her health. She led me to the elevator and up to her room, making out with me at every opportunity. I got some looks from a few people but I wasn't so much older that I was that out of place. It was still pretty common for grad students to hook up with underclassmen, after all. We got to her room which was the typical girl's dorm that most of us have seen. Much nicer and more warmly decorated than a typical guy's dorm. There was a nice sitting area and kitchenette and a door that led to the shared bedroom.

Sherry started to pull me into the bedroom with a seductive need before I stopped her. "Aren't you going to introduce me to your roommates?"

Sherry gave me a crooked smile that would make Natalie Dormer blush before leading me to her friends. "Jay, this is Starla and Louise. I went to high school with Starla and she knew Louise. They're both freshmen. Starla is a long jumper for the university. Louise is really, really smart. Uhmm... anything else you want to know?" she said in a rush before giving me a little tug. I pulled back on her and sat down, pulling her into my lap as I landed.

I extended my free hand and said, "Hi. I'm Jay. Sherry's sister, Carly, is my girlfriend." While I said this, I openly rubbed Sherry's thighs in a very inappropriate way for the boyfriend of someone's sister. Starla looked a little scandalized, but I thought I saw a twinkle in Louise's eyes. "What are you guys majoring in?"

Starla sputtered a little bit trying to compose herself and Louise piped up, answering first, "I'm pursuing a double major in Linguistics and Computer Programming," she said leaning forward and letting her shift fall open slightly. It was clearly intentional. Louise was pretty short and thin with the lithe frame that reminded me of a ballet dancer. Her breasts were not large but that didn't stop her from showing them off. Her long black hair was tied back in a braid that she twirled in her finger as she watched my eyes flick down to her exposed cleavage and back up.

"And what about you, Starla?" I asked, using sheer willpower to tear my eyes from the cavernous expanse of Louise's gaping shirt.

"I'm I'm trying to decide between a degree in Applied Psychology or an Individualized Study of body kinematics." Her arms were folded across her ample chest as she studied me coldly.

I looked at her, she was almost the opposite of Louise. Tall, maybe even taller than Carly. A little bit thick but not in a bad way. Strong legs. Nice butt and curves. Huge tits. Bigger even than Kyrsten or Sherry. She kept them underneath a slightly frumpy sweatshirt so you couldn't tell for sure though. Her brown hair hung around her face and she absent mindedly touched the gold cross dangling from her neck. "Body kinematics? So the study of how the human body moves?"

"Yeah, pretty much," she said, staring as I kissed the back of Sherry's neck. "I'm... I'm sorry... didn't you say you were Sherry's sister's boyfriend?"

"Yeah, why?"

"Uhh.. well... " Starla said, finding her thunder quashed once again by my open admission.

Louise came to her rescue, "I think Starla wants to know why you're groping and kissing Sherry."

"What? No... I don't care... It's not my business."

"Well I want to know," Louise said, again with the twinkle in her eye.

"Sherry, what am I?"

"My sister's Master. And mine too," she said while squirming in my lap.

"And what are you?"

"An obedient set of holes, Master."

"Good girl. And does Carly care that I'm fucking you?" I asked. I stared at Starla though and watched as she squirmed.

"No. In fact, it was her idea."

"That's right. Any other questions, girls?"

"How long are you going to be... uhmm... busy?" Starla asked.

"I don't know. A couple hours," I told her as I teased up and down Sherry's thighs.

"May I get my stuff out of our room?" Starla asked.

"Of course you can. It's your room," I said. Maybe I was getting better at noticing or maybe I was projecting my wants but it seemed like Starla might be just as submissive as Carly and Sherry. "Do you need anything, Louise?" I asked as Starla walked back to the bedroom.

"Nahh... I'm good. If I forget something, I'll just pop in. You probably won't even notice me you slut," she said teasingly to Sherry who just blushed.

"Okay. Hurry up, Starla. I need to take care of Sherry before she explodes."

Starla came back out of the bedroom wordlessly, clutching her books to her chest almost like a shield. I grinned and waved at them, "Nice to meet you too. I hope to see a lot more of you both."

"We do too, Jay," Louise said as she sat back, spread her arms and criss crossed her legs seductively. I heard Starla hiss something to Louise but it was muffled by Sherry's sounds as she practically yanked me into the bedroom.