The Conquest Club Files 16

The Conquest Club Files 16

By: AlexClayton

Tagline: Convention Cosplay

***

Hunter File: Annie (Model Inspiration: Jenna Lynn Meowri)

Age: 24

Height: 5'4"

Figure/Stats: Average 33C-24-32

Hair: Red

Eyes: Green

Trophy Taken: Cute Red Bra/Panty Set (from under a Kim Possible Costume)

Hunter File: Victoria aka: 'Vicki' and 'Bri' (Model Inspiration: Bree Daniels/Bree Victoria)

Age: 18

Height: 5'7"

Figure/Stats: Slim with long legs, 34C-24-35

Hair: Blonde/Brown

Eyes: Green

Trophy Taken: Purple Cheerleader Costume panties.

***

After the Labor Day Poker Weekend and Sex Marathon, I started being a regular fixture at each of the MILFs' homes. I didn't just fuck the wives and then leave or anything. I also helped the guys with yard work, construction projects, home upkeep, general cleaning, and whatever. I'm not a total bastard, ya know. It also gave me an excuse to elude my sister, who was looking for an encore. My biggest shock came after helping the Moreaus out one night and having dinner with them afterwards when Zander handed me a few envelopes.

The first was stating my acceptance into Indiana University at Bloomington for the FALL semester (something that was already a week or two in) for me to start taking correspondence courses, like right fucking now, via distance learning on the understanding that I'd be transferring to the main campus in Bloomington in the spring. My mouth opened and hit the floor. How the hell did I get accepted to a college that I didn't even apply to? Then I looked at the next one. That was from their law school saying that I'd been accepted into the pre-law degree program there on the recommendation of the law firm in my hometown. I tear open the third one and I'm floored to see a certificate for a full ride scholarship for seven years of college... enough to get me a bachelors AND a masters degree. A quick mental calculation tells me that this is just shy of half a million dollars in tuition.

I'm stunned as I just gape at the papers. Up to now the most I've ever done for college was take a few general education classes here at the local community college and that was as work allowed. I didn't rate good enough academically to get any of those scholarships, nor was my football playing good enough for a sports scholarship, and I refused to be baited into those traps known as student loans, so I paid for classes myself as I could. But now here I was, 22 years old with most of my friends already out of college or about to do their last year of it, now being handed a full fucking ride.

I look up at the Moreaus who are smiling broadly at me. Shaking my head, I push the papers back Zander's way. "No sir," I say softly. "I can't accept this..."

"You can and you will," Zander said. "You're a smart young man with a good head on his shoulders, a solid work ethic, and you managed to present a very convincing argument to me while under pressure," he said that last part with a laugh, referring to my quip at the recent poker party. He then pointed to the papers. "You can get a prelaw degree within four years... shorter if you take an overload of classes every semester. Once you have a bachelors, then you take the LSAT and go on to your actual law courses. Once you have your JD, that's a Juris Doctorate Degree, you'll intern with my firm and then take the Bar Exam to be licensed." He then eyed me. "That is if you're interested, of course."

"But I can't take your money, sir!" I protest. "It doesn't seem right."

"Honey," Betty now gives me a motherly smile as she pats my hand. "You're Gerry's best friend since the first grade. It crushed him when you weren't able to go to Purdue with him to play football, but he always did enjoy coming back home and hanging out with you. You've always been a big help in the neighborhood even before we all got intimate the other night. And we have more money than we know what to do with. We're always donating to local charities and scholarships, so it just seems right that we help you out as well. It's the least that we can do for you."

"It's not like paying for your housing, tuition, and books is going to put us out, if that's what you're worried about," Zander added. "We invested wisely, and we live modestly, so a lot of what I made in the NFL back in the day is just sitting in our bank account collecting interest. Hell, we live here just off of my salary at my law firm alone. So you're okay there."

"It's not that, sir," I say, "It's the principle of the matter. I don't want things just handed to me like this based on who I know. Mom and Dad always taught me to work for what I want and have."

Zander was nodding his head. "Okay then, then think of it this way; you can pay me back by coming to work for my firm once you get your degree and license. Deal?"

I would've been stupid not to take it at that point.

As it turned out, he'd gotten me in at THE last possible day for late registration and so I had a lot of catch-up to do. The materials package got there the following Monday which told me that he'd ordered them ahead of time and had them shipped... the bastard. The fucker even gave me a new laptop! Memo to me: remind me to flog his wife the next time I see them. Anyway, I got so wrapped up at that point trying to get everything in order by quitting my job, withdrawing from my trade school, catching up on my newfound college course, and getting ready for the convention that time just seemed to fly from that point. In fact, it was convention time before I knew it.

I was expecting Annie to call the Monday Night before the convention started so that we could go over schedules and final costume details. But then life decided to throw me a fucking curveball. My parents showed up with Vicki. "Ahhh... hi..." I say to all three of them when they were at my doorstep. "I didn't miss a planned dinner, did I?"

"No," dad said, coming in with mom and Vicki "but we did want to ask you something." My first thought was 'oh shit... we're found out," but when I gave a questioning look to my sister she just shrugged and gave me a sheepish, apologetic look. "That convention of yours is this weekend, right?"

"Yeeeeeeah..." I say cautiously as at this point, I don't want to say anything until I know what the fuck is going on.

"Well, do you recall that one of Vicki's gifts this year was tickets to that convention since she's been wanting to go by herself for years now?" dad asked.

"Yeeeeeeeeaaaaaaah..." I say, even more slowly now while giving Vicki a murderous glance. I swear to fucking Christ if my weekend is about to be ruined...

"Well we can't get a hotel room for her by herself," mom then chimed in.

"Of course you can't," I scoff. "You have to get them, like, six months to a year in advance because they sell out so quickly!" I tell them. "Why else do you think that I make my reservations at the same hotel once I check out the last day of the convention?"

"So you do have a place already then?" mom said with a smile.

It then clicked for me what they wanted from me. "Oh HAAAAAeeeeeeellll no..." I say, shaking my head emphatically. "I already have plans and I already have a roommate for the convention!" I protest.

"Oh I'm sure that your little friends won't mind another person staying there," mom says in that damn dismissive manner that irritates me so much. "Worst case; I'm sure that you can give up your bed and sleep on the floor, or a couch if they have one, while your sister gets the bed."

"I don't fucking believe this..." I groan, rubbing my hands to my face in abject disbelief. "You have GOT to be kidding me!"

"This is your sister's dream that we're talking about here, son," dad now says, slightly annoyed at me. Well that makes two of us because they could've just fucking called instead of coming over here and treating me like I'm still a kid. "You two can drive into Indy together, go to the convention, and drive back to even save gas. You'll be saving us all a lot of money," he then added, sounding completely reasonable.

"What about my friend?" I ask, exasperated. "I can't just CANCEL on them!" I'm careful on my use of pronouns since I know that they'll have a shit-fit if they knew I was staying there with a girl who was NOT Liz.

"You're a smart boy, you can make arrangements," mom said, getting up and giving me a hug and a kiss on the head. "Thank you for doing this, honey, can you be a dear and give Vicki a ride home?"

"You're leaving her here?" I ask tersely.

"Of course, you two have plans to make. Maybe you can even do matching costumes. Wouldn't that be so cute?" mom gushes as she and dad thank me again and head out the door.

The door closes and I round on Vicki. "I fucking hate you right now," I practically spit at her.

"At least it wasn't about... like... you know... the OTHER thing..." she immediately says defensively with her hands up in surrender before gesturing to the door. The way I was feeling I did have half a mind to put her over my knee and spank her ass as it was. "They didn't even see your other room when they came in," she added. I silently thanked god that I had the foresight to always keep the dungeon bedroom door closed just in case people dropped in like this. Then she shrugged. "What's the big deal, anyway? Which one of your friends are you getting a room with?" A grin graced her lips "Is it Gerry or one of your other friends from school?"

"Gerry is on the road this weekend because the Colts are playing the Texans and even if he was in town, he'd be staying at his own home with his wives," I say dismissively, "so you're going to have to wait to bang him, you lecherous homewrecker you." I then shake my head. "No, I have my cosplay friend, Annie, staying with me and she wants to do a photo shoot... among other things."

Vicki cocked her head. "I'm into the cosplay scene and I don't think that I know her... at least by that name anyway."

"That's because I know her real name and you don't," I snort in amusement. "You probably know her better as Alluring Anne."

Vicki's hands shot to her mouth as her eyes widened and she gasped in surprise. "Ohmygawd! NO WAY!" she practically squealed. "You're sleeping with Alluring Anne!?"

"Well that WAS the plan before you butted in," I say, giving her a withering look. Then I check my watch, she's supposed to be calling in soon. I grab my phone to make sure it's close for when she does call in and take the time to shoot a quick text to Liz to let her know of the changing development for the upcoming weekend. Naturally, my ever-supportive girlfriend... that was sarcasm by the way... laughed her head off in emojis. Makes me want to prank sex her with her own sister so that she can share in my misery... then again... both of them might like it too much. Rumor had it that Gerry had already done that to both of them... in the shower... in their own home no less. Have I mentioned that Gerry is a fucking bastard?

Anyway, I'm already dialing Annie up to let her know of the 'added guest' for this weekend. "Yeah, it's my sister," I tell her after laying out the initials. I see Vicki bouncing up and down excitedly out of the corner of my eye. I sigh and then add, "and she's a big cosplayer and a huge fan of yours."

"Does she want to be in the photo shoot with me?" Annie offers without even missing a beat. "I was planning on doing a lewd Kim Possible shoot this year and if she could throw it together, she could be one of the cheerleaders on Kim's squad. You can then be one of the evil henchmen who's captured us."

Vicki, overhearing this from my phone, squeals so loudly next to me that I'm sure my eardrum is ruptured at this point. "Yeah... I think that she wants in on that."

"Awesome! Can't wait to see you both this weekend! Annie says cheerfully before hanging up.

I pocket my phone and glare daggers at Vicki, who's smiling from ear to ear. "I already got the perfect outfit back home!" she gushes.

"I'm sure you do," I say sardonically. "You do realize that she does ero cosplay for her websites, right?"

"Duh," Vicki rolls her eyes like it's the dumbest thing I've ever said. Then she's smiling at me. "Well, now that that's done, wanna punish me for intruding in on your life like this?" She turns and wiggles her ass at me for effect. I groan and roll my eyes at that. "Aw, come on," Vicki playfully pouts, "you'll be fucking us both anyway for the photo shoot at the convention."

The fact that she's already caught onto that little bit of the photo shoot is disturbing. "You really need to get a boyfriend who's not me," I tell her.

"I know, but for now you'll do," she smirks. "Come on... plleeeeeease.... I'm horny!"

Hm... well, if she wants to be punished, who am I to deny her? I also remember that a 'congratulations' package came from Gerry that I hadn't had a chance to use yet since Liz wasn't here. Oh well, I guess I get to break it in with Vicki then. I walk into the dungeon room, grab a ball gag and a pair of fuzzy handcuffs, and then toss them out to her. "Strip, put those on, and kneel, bitch." Vicki squeals with glee as she proceeds to do just that. I shoot a quick text message to our parents letting them know that she's going to hang here tonight as we're going to watch movies to get costume ideas and they buy it hook, line, and sinker. They thank me profusely and mention that they can have some quality time together without having to bother Vicki. I lock the door just in case they get done bumping uglies early and decide that they want a fucking movie night with us as well.

Before all of this, just the mere thought of my parents having sex would've grossed me out. Now, to me, it's just Tuesday.

I grab the big ass black box and a black velvet bag out from under the spare bed and carry them out to the living room. Vicki is already naked with the gag on, and her hands cuffed behind her back. She looks at the box skeptically as I put it down in front of her. I lift the cover and unfold the flaps inside to reveal a sybian machine. Her eyes widen at the sight of it as I then reach into the bag to get the dildo attachment to put on top of it. I then point down at it with a wicked smile on my face. "Get on it, bitch," I command. To her credit, she stands up, stoops over the thing, and works herself down onto the dildo. Once she's kneeling again, I make sure that her pussy lips are spread on either side of the vibrating ridge and make sure that she's comfortable with the dildo up inside of her. Then I get more cuffs to make sure that she's cuffed at her knees and ankles to the thing so that she can't escape.

Then I turn the thing on.

Vicki arches her back and screams through her gag as she starts shaking as if she'd been electrocuted. Yeah, I might've turned it up a little high to begin with, but I also know that she can take it as she's been talking about using hitachi wands with Stacy. While she's screaming, writhing, and moaning on the sybian, I'm standing behind her taking my clothes off and then grabbing a bottle of lube from the bag to rub generously on my hardening cock. I then bend her forward, position my cock right at her puckered ass, and slowly push my way in. I can feel the sybian's dildo vibrating inside of my sister as I lodge my cock all the way up inside of her ass. The back end of the vibrating strip is tickling my balls as I just stand there hunched over her. My hand slides around the front of her neck to hold her as I then plant my other hand on her hip to slowly start to fuck her hind end. "Is this a proper punishment for you, slut?" I hiss into her ear while divorcing my mind between the intimate act and the fact that I'm doing my sister again.

"Mmm-hmmm..." Vicki whines submissively from behind her gag. Already I can feel her pussy and her ass convulsing as her body shakes. She's already cumming hard just from me doing this to her. It feels so wrong to be fucking her but at the same time doing it feels so damn fucking good. I'm so going to hell for this but if I am going, I'm going with a damn smile on my face. I fuck her ass with slow, methodical thrusts until I can't hold it anymore and I blow my wad up inside of her. She lets out a guttural moan and I swear that she cums again from me fucking her this way.

After we're spent, I turn the machine off, release her from her bonds, and carry her to the shower for us to clean up. We make out and fuck some more, getting off quickly, before we wind up sprawled out on the couch, under the blanket, watching some old-school anime. Bubblegum Crisis, if anyone's asking. Now we have some plausible deniability. Of course, that lasts only until the first nude scene that we come across and then we're fucking again. This time we fall asleep on the couch and stay there all night long.

*

The convention comes along a couple of days later and we're heading into Indy for the convention, checking in on Thursday night before the official start Friday morning. We get parked at our hotel and up to our room. The receptionist gives us a knowing look as she notifies us that our roommate is already checked in. One guy, two girls, and one queen sized bed. Yeah, I'm sure she's done the math in her head. Then again, a lot of these things happen at the conventions (or so I'm told) so she's probably jaded by the whole thing. Anyway, we lug our luggage and our backpacks up to our room and meet Annie.

After the initial introductions are out of the way, Vicki goes all fangirl on Annie, the two of them start talking cosplay, makeup, tailoring, and are talking a mile a minute that I soon just tune them out. It's not until they come back around to the convention schedule that I get back involved. "So when do I need to be at your booth to look scary?"

"Con security is going to be at my booth so you can do what you want to," Annie explains. "I only need you for the afternoon signings and the public photo shoot. The private photo shoot for the more not safe for work photos is Saturday night that I need you two to be at." She then smiles coyly. "And then we can come back here for the even more 'intimate' picture taking."

"And you're not at all troubled about Allen and I sleeping together before all of this?" Vicki asks.

"He'd told me about it and considering he's already sleeping with his possible future mother-in-law, sleeping with you is hardly a stretch," Annie shrugs. "Besides, it's not like I can cast moral judgements since I take off my clothes and do lewd and suggestive sets for guys to jack off to for a living." She laughs. "Hell, I think that I might up getting more sales if they know that I have an actual brother-sister model pair for this one! You should've seen the revenue I got when I did a suggestive stepsister set one time." She eyed us and then eyed the bed. Then she stood up and took off her t-shirt, exposing her white bra clad C Cups underneath. "In fact, we should probably have a little bit of an ice breaker session before the lewd shoot on Saturday, don't you think?"

I'm grinning as I follow suit by removing my clothes as well. As we're undressing, we're eyeing Vicki who hesitates for a moment and then does the same. Oh sure, NOW she fucking goes shy and prude on me. Annie goes to her first once they're naked, taking her by the hand and dragging her onto the bed. There they cozy up to one another, laying on their sides facing one another. I've been involved with a few threesomes at this point to know to keep out of it until invited in. So I stay sitting on the couch in the room while I watch them make out. It starts off with soft, tentative kisses at first and then Annie casually caresses Vicki's bare thigh. Vicki moans softly into Annie's mouth as Annie then rolls her over to her back to take a more dominant role. Soon Annie has Vicki mounted and the two of them are humping and grinding against one another.