The Conquest Club Files 15

Hunter File: Jessie (Model Inspiration: Rachel Hunter from the music video "Stacy's Mom")

Age: 36

Height: 5'7"

Figure/Stats: Buxom MILF, 32D-24-30

Hair: Blonde, down past the shoulders

Eyes: Blue

Trophy Taken: Black Shibari Rope

Hunter File: Sofia (Model Inspiration: Sofia Lane from Playboy)

Age: 35

Height: 5'6"

Figure/Stats: Average to Curvy sized MILF. 34C-26-34

Hair: Dirty Blonde, short cut

Eyes: Green

Trophy Taken: boy cut white lace panties

Hunter File: Betty (Model Inspiration: vintage burlesque performer Betty Howard)

Age: 40

Height: 5'6"

Figure/Stats: Curvy/Hourglass. 38E-25-37

Hair: Blonde

Eyes: Blue

Trophy Taken: pink silk panties

***

When the fall semester came around, I was pretty much in hell. EVERYONE in my remote age group went back to college while I continued my steady work. I took trade classes to further my skill set and eventually move from pool management to something else... like a career with benefits. Liz went back to Bloomington for her classes and Stacey went with her. As much as I hate to say it; even Vicki started college, but she was staying at home while taking courses through the community college and that was keeping her busy. Probably a good thing, really. Anyway, that left me in the neighborhood pretty much by myself. Sure, I could drive all the fucking way into Indy to get a booty call from Kimmy, Jen, and Alicia, especially since the first two on that list were properly knocked up now, but that was a long ass drive and gas ain't cheap. I occasionally did that during Gerry and Tycen's away games just to cheer them on while inside Gerry's private home theatre along with the girls

Yeah, I know, I had Mrs. C but I'd like to expand my horizons, ya know? Besides, she's only available to me on Thursdays only if Mr. C goes bowling.

And yeah, I know that my sister is ready, willing, and able, but we're only doing that on rare occasions to avoid getting our parents suspicious.

The only thing that I had to look forward to after all of my friends left town for bigger and better things was the gaming convention that was coming up later in the year. I reserved my hotel room WAY in advance and had been doing that since I was old enough to drive. It was the best four days of gaming, cosplaying, and anime every year for me. One potential partner that was coming up for me was Annie.

I'd known Annie ever since I started going to conventions. I was one of her first supporters when she was a no-name cosplayer and model when she turned 18 and have been supporting her online ever since. I'm also her safe space at the convention for when guys get a little too grabby or suggestive then she'll use me as an excuse as to not go out with anyone. Once they saw that I was a six-foot tall, slightly muscular guy who played high school football and could take a hit or two, they usually backed off. When I could quote facts about her that not even her fans knew, that tended to get the over zealous skeptics out of there. Occasionally, I would have to lay someone out who decided to 'push' the issue and that settled any remaining arguments.

Yes, I know how to fight, don't look too shocked. I've been Gerry's sparring buddy and tackling dummy for years now. Ya tend to pick up a few things along the way.

So yeah, I was her unofficial bouncer and bodyguard whenever we were at the same conventions. Now that she was becoming a paid model for her cosplaying, including the lewds and the nudes, she started to email me her convention schedule asking me (if not begging me) to appear at the ones that I could so that I could run interference for her. We talked on a regular basis and yet we never hooked up in the biblical sense because she lives on the west coast and I'm here in the midwest. That, and despite us flirting and occasionally kissing at conventions to sell the cover story, we just never pushed the issue. I guess we were both afraid that we'd lose our friendship with each other if we actually took the plunge and slept together.

Which is why I was shocked when she proposed to do just that.

It started off innocent enough when we were playing World of Warcraft online tonight. Yeah, we're in the same guild that we've been in for years and it was pretty much made up of us cosplayers that ran in the same circles. We all knew each other, knew everyone else's true identities, but really didn't care since we were there to relax. Yeah, I play WoW. Really? Are you really that surprised? Come on, it shouldn't be a shock now. And for the record, for Annie and I it's "For the Horde". Read it and weep. Anyway, we were talking on discord and were taking a break from the game when she finally came out and told me what was bothering her that night.

"It's the convention coming up, Allen," she told me, sounding a bit sad and panicked. "Those bastards in the hotel convention tell me they screwed up and double booked me. But they decided to drop MY reservation despite it being older than the other people. They still want me as a paid guest, but they can't find me any place to stay at," she explained. "Any place remotely close to the convention center that is. You already have your hotel room booked downtown, right?"

"Yeeeeeeaaaaah..." I say cautiously. "It's a single bed though."

"Can I stay with you then, please?" she asked me straight up. "I know you have a girlfriend now and all but, please, I'm desperate." She was now practically begging which is why I was a bit surprised to hear her drop to a seductive purr. "I can... make it worth your while... I mean, if your girlfriend doesn't object, that is."

"Liz?" I snort with amusement. "Knowing her she's probably already made her way through half the sports teams and might be working on the Chess Club at her campus by now." I laugh. "We have an open relationship, and she wouldn't care in the least little bit. She knows that I'm friends with you and if I were to tell her right now, she'd probably tell me that it was about time I'd slept with you."

"Really?" Annie sounded shocked at that.

"Call her up or text her yourself if you don't believe me," I say before I give her the number. I was already texting Liz to let her know about this upcoming development and she told me to have fun and informed me that it wasn't the Chess Club that she was fucking, it was the Math Club. She needed tutoring in Calculus. Well gee... my bad. I then looked at the next message from her. "Oh, and Liz says that she wants pics of us."

I hear a cell phone beep on the other end of discord and Annie gasps in surprise. "Yeah, she just told me the same thing and told me to come up with a safe word if I really want you to rock my world? Is... is she serious?"

"What?" I ask, surprised at her innocence. "You thought I was joking when I told you that I'd converted my spare room into a BDSM dungeon for Liz?"

"Well, I, uhm..." she sputtered at first. "You know what, never mind. That actually gives me some ideas for a selfie photo shoot that I had been planning anyway that was a bit dominant-esque. My fans have been asking for a bit more lewd and I've decided to give it to them after that little bondage set that I did earlier this year. My ratings and revenue on my sites went through the roof. Up for being a model for me?" she asks with hope in her voice. "If you don't mind your face being seen, that is."

"Meh," I shrug even though she can't see me. "If we're cosplaying, I could care less. Hell, it's not like anyone around here would think any less of me even if I did care about their opinion."

"Great! So let's talk about costume ideas," Annie said, now extremely happy that she not only would have a place to stay while she was here, but she'd have a 'professional' partner for her little selfie photo shoot that had zero expectations about a relationship with her. By the time we settle on our costume concepts for every day of the convention and going over the photo sets that she wanted to do with me, I was fucking hard. We're talking so hard that it hurts. Annie was sympathetic about it when I said that I needed to log off of the game to take care of it. "Wish I was there to help you with that," she said with a combination of amusement and wishful thinking.

"Yeah, I do too..." I bemoan right before I sign out of both discord and WoW.

Liz wasn't much help as she'd laughed in her texting with me saying "sucks to be you" and then compounded my misery by sending me a nude selfie of herself with Stacey in bed. The bitch. I texted Stacey to have her give Liz a good hate fucking with a strap-on since the two of them were roommates. Stacey said that she'd comply with the order with a wink emoji and even sympathized with my plight as well.

I was caught up in all of the texting, while surfing the net for some decent porn to get off to, when there was a knock at my door. With a quizzical arched eyebrow, I looked down the hallway to make sure it was my door and there was another knock. It was my door. I got up from my desk and walked down the hall, albeit a bit stiff because of my raging hard-on, and answered the door. My jaw dropped when I saw Stacey's Mom (and yes she had it going on... thank you I'll be here all week) standing on my doorstep wearing black high heels, a trench coat, and a smile. "Missus S!" I say, shocked to see her here. "Uh... hi! Uhm... what can I do for you?"

"It's more of what I can do for you, you poor boy," she said with a gentle smile as she walks in, backing me up in the process. She's holding up her cell phone, waggling it a bit and I can see a text from Stacey asking her mom to come over to my apartment to help me out with a 'very hard problem that has popped up.' Mrs. S then closes and locks my door for me. "And tonight, you can call me 'Jessie' as we're going to get to know each other very... intimately." I swallow hard as I gape at her. Up to this point I'd had yet to fuck Mrs. S... Jessie... or any of the other MILF Blondettes in the neighborhood; Mrs. Moreau, and Mrs. Lane, specifically. Mainly because I was too busy fucking Liz and Stacey. I knew that Stacey's parents swug with some of the other older adults in the neighborhood but still to see her here, offering herself to me, was a surprise.

Even so, I couldn't help but ask if Mr. S was okay with this. "Of course he's okay with it, dearie," Jessie says, her smile now beaming. "When I talked to him about it just a half hour ago after Stacey texted me, he was on the phone with the Cafferys and they're going to double team Audrey tonight. So it's just you and me tonight... ALL night." With that, she then gives me a seductive look and starts unbuttoning her trench coat from top to bottom. My eyes follow her hands and then when she's done, she reaches up, opens the coat, and lets it fall to the floor.

Oh...

My...

Facking...

GAWD!

Jessie is wearing nothing but black shibari rope tied around her torso in the classic body harness style that accents her breasts and hips nicely. It's done with the four ropes going down to the crotch in a swimsuit looking method to keep the pussy accessible rather than doing the pussy cleave method by going between the labia and closing it off. My jaw hits the floor as I drink her in. Her rosy pink nipples on top of very firm D-Cups are already standing on end. My eyes follow her as she drops to her knees on the floor, using her trench coat as added cushioning. Jessie reaches out to snag me by the waistband of my sweatpants and pulls to coax me forward. Then she fishes out my cock from underneath and immediately wraps her lips around them to suck, all the while looking up at me submissively. Jessie moans as her head starts to bob back and forth, her lips moving up and down my shaft, as she sucks me off.

"Gawd Damn..." I hiss as my mind engages enough for me to participate. I grab Jessie by the back of her head and thrust my hips forward to meet her face as it comes down my cock. I practically fold myself over her head while holding her head clutched to my crotch. My cock explodes into her mouth faster than I can warn her... hey, I had a lot of pent up cum from not getting laid in a couple of weeks and from the events from tonight... sue me. But Jessie, to her credit, moans even more and expertly swallows the flood of cum down as easily as a porn star. My body is twitching uncontrollably, and it takes every conscious thought I have to keep from toppling over and possibly onto her. Once I am done, though, I'm feeling lightheaded to the point that I do have to sit down in front of her and lie back, groaning pitifully as I collect my senses.

"Oh you poor dear," Jessie says as she yanks my sweats all the way off of my legs and then straddles them to get to my baggy t-shirt that I'm wearing to get me naked. "I wish you'd've called me sooner. It's not healthy for a man of your age to be pent up like this. You should be getting off no less than once a day," she explains. Then she bends over again, gathering her massive tits in her hands to rub them on either side of my cock. Despite just having one helluva orgasm, I'm still pretty hard. She dips her head, putting her chin to her chest, to suckle on the tip of my cock and swirl her tongue around its head. It makes my body jerk and spasm from the intense sensitivity from having just got off. Jessie brings her head up and smiles at me once I'm totally rock hard again. "I'd heard from Audrey that you like getting a tit job," she says with a smile while continuing to rub her breasts up and down my shaft.

"Uh-huh..." I moan stupidly, nodding like an idiot, as I watch her. Now she's playing with her breasts, pinching and tweaking her own nipples as she sucks me off and fucks me with her tits, and I groan deeply again. The pleasure is going straight from my cock to my brain, making it hard for me to even think. I'm, like, grabbing the carpet now as intense as her blowjob/tit job is. She just seems to know how I tick... or just knows how guys tick in general... as she's swirling her tongue around to drag across the soft head of my dick before swirling it under to catch the part just under it where the folds meet. "Oh god..." I gurgle a half second before she makes me blow again. Just like before, she deepthroats me and swallows down every drop of my cum as it shoots into her mouth, not letting a single glob of it spill out.

Normally two orgasms would do it for me on any given day since Liz and I started living together, but she's been gone off to college for a couple of weeks with everyone else and I had hardly been laid since. I'm ready to go again almost immediately. When my head clears, I see a brief view of Jessie disappearing into my dungeon room and catch the glint of a jeweled butt plug shining from between the cleft of her ass. Holy shit did she come prepared for this. How quickly was Mr. S able to get her into all of that for her to get here while I was still in the middle of texting everyone and looking for some porn? The conclusion I reach is 'not long' and knowing that gets me going again. I roll to my stomach, pop up to my feet, and follow her into my spare room. Jessie is already there, down on all fours in the middle of the room (I don't have a bed for it yet, just a blanket and a lot of pillows in the middle like a little nest bed), with a paddle resting across the small of her back. I don't need an engraved invitation to figure out what she wants.

I kneel down beside her head and make her twist it to her left to suck me off again. At the same time, I take the paddle and smack her hard across the ass, making her moan "Harder" around my cock. So I give it to her harder. I don't have to worry about being quiet. I've since soundproofed the entire apartment so I don't disturb my neighbors. Jessie starts rocking her body forward and back in time to my paddling, all the while dutifully sucking on my cock until I'm hard again. At the same time, I reached under her to feel up her lovely left breast and found that she'd found the little nipple clamps that I'd bought for Liz. It's one of those jeweled looking things that clamp around all sides of the nipple and hang on sorta like a pasty while keeping the nipple pinched. I can't help but to fondle her tit and pinch the tips of it even more to make her moan around my cock. Once I'm stiff a third time, she pulls her head away from me, letting my cock drop out of her mouth. "Fuck me, hard, please," she moans. "Fuck me as hard and as fast as you can and don't be gentle about it." I toss the paddle aside, crawl behind her, mount her ass, and drive my cock as far into her as I can, making her moan loudly as I penetrate her already wet and waiting pussy.

Now, I have to take a moment here to hand it to Mr. S's handiwork. I don't know if he's damn good at tying knots in a hurry, or they have this rope harness rigged so that all they have to do is untie a knot here or there for her to just slide into, or what, but I was able to grab a hold of two of the ropes at her shoulders and yank backwards as I pump my hips hard forward. I feel the head of my cock ram against her cervix and hear Jessie scream her head off in the process. Since I've already gotten off twice, I have a lot more staying power now. But still, she feels pretty tight, and I think that it's the ropes that have been looped around her thighs and are resting on the outside of her labia right where her crotch meets her legs that's doing it. Either way, it feels fucking amazing. I'm grunting and groaning like a wild caveman as I pull her body back in the harness as I ram my cock into her repeatedly as hard as I can go.

At the same time, Jessie's head is bobbing up and down like a damn bobblehead doll as I fuck her senseless. She's even pushing back against me, making my cock and her plug drive into her even harder and deeper. "NNnnuuuuhgggghh... Goooooood..." she groans deeply as then her body begins to twitch and spasm as she cums hard. "Donnnnn't stooooooop!" I fuck her all through her orgasm and continue fucking her until she gets off a second time. By that time her arms and legs had given out and I'm basically lying on top of her, pounding my hips down into her ass as she moans pathetically underneath me and drools. She told me later that had I looked at her, or had a mirror to look at her, I would've seen that I'd literally fucked her silly and her eyes had been rolled back into her head at the time as I fucked her to my third orgasm in about an hour.

I rolled off of her, and the both of us just lay there collapsed on the floor, covered in sweat, breathing heavily. Jessie recovers first, getting up and reaching between her legs, plucking the butt plug out of her ass and letting it drop. "Be a dear and help me out of this thing, will you?" she asks me sweetly. I get up onto my knees and help her take the nipple clamps off before untying the knots indicated by her to let the rope harness just slide off of her body like a swimsuit. I'm going to have to have Mr. S teach me that trick. At the same time, she kicks her high heels off to stretch and flex her feet. Once she's totally naked, she throws her arms around me, giving me a big ass hug and an equally big ass kiss with her tongue invading my mouth. "MMmm... Thank you for that," she purrs.

"Thank you for coming over and doing that, ma'am," I tell her, holding her close and kissing her back. I reach down and squeeze her tight, round ass for effect. "I needed that."

"Well don't be a stranger to my house, young man," she pulls back just enough to eye me. She then reaches down and cups my cock and balls, giving them a light squeeze. My cock starts to twitch back to life from her touch. "Anytime you need release, you better call me, or Sophie, or Betty, or Audrey. We'll take good care of our young stud."

Cougars... I swear...

But, I'm not about to give up pussy when it's offered, so I graciously thank her and swear that I'll do just that. That satisfies her and she gives me a mischievous smile with a gleam in her eyes. "Good. Now I hope that you have more in you as I expect to go home bow legged. It'll drive my husband wild, and he'll fuck me unconscious when I eventually get back."