The Conquest Club Files 05

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Another MILF in the neighborhood wants me...
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Part 5 of the 17 part series

Updated 06/16/2023
Created 08/07/2015
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AlexClayton
AlexClayton
2,105 Followers

Hunter File # 0005: Jessie

Age: 35

Height: 5'7"

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

Hair: Blonde, down past the shoulders.

Eyes: Blue

Trophy Taken: White Bikini Swimsuit (I seem to be collecting a lot of these lately)

*

Hunter File # 0004b: Sofia

Age: 35

Height: 5'6"

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

Hair: Dirty Blonde, short cut.

Eyes: Green

Trophy Taken: blue one piece swimming suit with a peek-a-boo keyhole in the front.

*

Do you know what that sound is, Mr. Anderson? That is the sound of inevitability...

If it is one thing that I've noticed when taking on a first time, shall we say...'client'... is that they get this particular look in their eye when they realize that something that they've fantasized about for so long was about to become a reality.

To paraphrase Agent Smith from The Matrix; it is the look of inevitability.

It's the look of uncertainty that they get when they wonder a few things; what they've gotten themselves into, what if I'm a real intruder and not the person they got to play-act for them, and are they really going to be into this?

It was getting late in the summer and Kimmy and I were out shopping for some back-to-school items. Normally I'd do the standard things for college; notebooks, folders, pens, pencils, box of condoms, ID showing I'm over 21, buy five get one free at the Oaken Keg card, et cetera...

But this time was different. This time I'd have Kim rooming with me and we'd opted for the four person dorm house this year since I'd opted to have my long time roomie as a preference again along with my new girlfriend. I wasn't sure if Tycen, my roomie, team mate, and all around best friend since our freshman year, had anyone in mind for the fourth room. I'd told him that it'd need to be someone that we trusted completely as I had all sorts of ideas for the coming semester.

Thankfully, he caught on immediately and told me not to worry about it since he's got his girl lined up for us.

Yeah, I know what you're thinking and stop getting ahead of the story. We'll get to her in a later installment.

Anyway, Kimmy and I were out shopping and were going for housewares as well as school supplies. We then took a detour into what was quickly becoming my favorite adult warehouse in town. I was perusing what kind of collar I wanted to get for Kimmy while she was off looking at various dildos when I heard a familiar voice behind me. "Oh my God, Gerry?" an excited woman's voice said, making me freeze in place as If I'd gotten caught red-handed with my hand inside the cookie jar.

Ah shit... That was Mrs. L... er... Sofia. Sheesh, of all the people to run into here...

Awkward!

I look back over my shoulder and sure enough, Sofia's there with a big ass smile on her face and her arms open wide. I'm sure I look like a deer caught in the headlights as she closes on me, wraps me up in a huge hug, and plants probably one of the best kisses I've ever had in my life right on the mouth. I'm caught off guard as she frenches me right there in the middle of the damn store!

When I finally manage to come up for air, she's still hugging me tightly and nibbling on my ear lobe. "I just wanted to thank you SO much for my birthday gift, Gerry. You have no idea what that has done to rekindle the passion between Tom and I."

"Uhhhh... you're welcome?"

Now she leans back and holds me at arm's length, giving me a motherly smile. "So modest. What happened to the 'take charge' boy that invaded my house?"

"Wondering how my girlfriend is going to kill me when she sees us like this?" I manage to get out.

Just then we hear an "Ah-HEM" behind Sofia. Speak of the devil. Sofia turns and gives Kim an amused expression while my eyes get even wider. Thankfully, Kim looks amused even with the crossed arms and ticked off attitude that she's trying to present.

"Not what you think!" I blurt out.

"You're cute, you know that?" Kim says, imposing herself in between us and giving me a hug. "I'm sure it is what I think and who can blame her? You are a good lay and I did get the ball rolling for you to have her." She gives me a peck on the cheek. "How are ya, Mrs. L.?" Kim asks turning in my arms to look at her.

"Fine and I was wondering if I could borrow your boyfriend again for a friend of mine?" Sofia asks. When Kimmy arches an eyebrow in curiosity and I start looking for the nearest exits out of desperation, Sofia plods on in her spiel. "Jessie and I, er, Mrs. S to you kids, are having a girl's night in her hot tub while Tom and John are out of town hunting this weekend. Stacey is out of town visiting her grandparents and I'd told Jessie all about our little... experience."

God Damn... is EVERY woman in this fucking town trying to pimp me out now?

I manage to get my head back into the conversation. "And your husbands are okay with this?" The last thing I want is either Mr. L or Mr. S coming home from hunting deer to declare open season on college running backs with no bag limit.

"Of course we have," Sofia tells me. "We've even taken up swinging since my birthday amongst ourselves." Kimmy and I both rock back in shock at that little revelation. "So, what do you two think?"

Kim looks up at me, "I'm starting to feel left out from all of this action you're getting," she says.

"Your fault on half of that," I point out to her. "Besides, I have at least half the football team planned for you and Tycen's girlfriend when we get to campus," I say without hesitation. "Believe me; you're going to get all the action you want once we get moved in."

"I want to watch, at least," she pouts.

Now my devious little mind kicks in as I think about Mrs. S's house. Her daughter, Stacey, is as old as Kimmy and I'd been over there a couple of times just to drool over Mrs. S. Yes, she'd heard us neighborhood boys sing "Stacey's Mom" more times than she'd like and the irony was not lost on anyone since about every male over the age of puberty wanted to nail her. The problem was that she never did anything to dissuade us either by wearing skimpy outfits and bikinis all the time.

Who knew that she might've actually liked all of the attention we gave her?

My buddy, Allen, who I'd blackmailed back at the pool, had a tree house in his backyard and that overlooked Mrs. S's backyard pool and hot tub. I know this since if we were not watching Mrs. S when we were teenagers we were gawking at Stacey in our senior year of high school when she'd become old enough to date.

Another thought had occurred to me. "You're sure that Mrs. S is onboard with this idea of me coming in and ravishing the two of you?"

"You can ask her yourself; she's over looking at the erotica novels," Sofia points and we all look that direction. Sure enough; in all of her MILF glory is Mrs. S in a tight ass white t-shirt that was straining to contain her womanly assets. She might have a few years on Mrs. L, but damn... Anyway, toss in blue jeans that I swear were body paint and you can get the picture from there. Don't get me wrong; I love Kim and her diminutive body and pert little tits that fit nicely into my hand, but Mrs. S has been the mental source of a ton of masturbation fantasies of mine for some time.

And be the breasts small As or triple Ds; let no man ever accuse me of breast discrimination.

Looking up from the cheesy Steampunk Erotica book she'd been looking at by some schmuck named 'Diesel Jester' (what kind of a name is that anyway?), she sees us staring at her and she waves at us. Dumbly, Kimmy and I wave back as it's starting to sink in to us just how kinky our neighborhood is getting. She tucks the book under her arm and comes over and says hi. "Uhm, Hello Mrs. S," I say, feeling the heat go to my cheeks and my groin as the object of my teenage erections is now painfully close.

"Gerry, please, call me Jessie considering what Sofia here has been persuading you to do." She says with a warm smile. "So are you in for our little arrangement?"

"You know what I do, right?" I ask cautiously, wondering how much Sofia has told her. "I break into your home. I capture you. And then I do whatever the hell I want to you for as long as I want to." She nods. "And you are okay with this?" Another nod. "And your husband is okay with this?"

Jessie laughs. It's the same light and airy laugh I remember from High School. "Of course. He's not going to come back and kill you or anything."

"Well, I just like to make sure about that." I tell her. "So what say this Friday night?"

"Sounds good to me." Jessie says with Sofia nodding excitedly alongside of her.

We hash out a few details including standard safe words and then go our separate ways. When we go back to shopping, I select a nice faux-diamonds on white leather collar for Kimmy and hold it up to her with a suggestive look in my eye. She nods her liking of it but she's keeping focused on her mission; getting some while watching. "What about me? How am I supposed to see you in action at Stacy's house?"

I tell her about Allen's tree house and I can see the gears turning in her head. "I can always offer for you to keep him company up there while y'all watch along with Liz."

"Why Allen?" she asks with a bit of distaste.

"He's had the hots for your sister for some time. That, and I owe him." I admit. She gives me a quizzical look and I add in, "I blackmailed him to sneak into the water park to get you and Jen that first night."

"With what?"

"That's between me and him." I hold up the open collar for her. "Now, do you want to be a good little slave and put this on for me and go do my friend so that you can watch, or do you want to miss out on the action?"

"What do you think?" she purrs, pressing up against me and puts her neck right into the collar where I then lock it into place behind her neck. I'll just pay for this at the counter while she's wearing it. Can't be the first time a place like this has done something like that. "Good," I tell her with a passionate kiss.

*

Needless to say, Allen was all over the idea when I called him up and told him what was going down. He'd been bent out of shape since the water park thing and this seemed like the only way to get him onboard with what I was doing. "Just like that? Friday night and I get both of the Caffery Sisters? What's the catch?" he asked suspiciously once he thought that this had to be too good to be true.

"That you have to let them watch the show that'll be going on in Stacey's backyard and house when I leave and don't make them do anything to each other. You don't even need condoms since they're both on the pill." I tell him.

"Alright, fine, I'll play along. My folks are going to be gone for a movie on Friday anyway, my sister is having a sleepover with her friends, leaving me here to watch the pets." He sounded so thrilled at having to do that. Ah the price we pay until we move out on our own. Thankfully, we both only had one more year of college before that dream would be realized.

When Friday came around, Kimmy knew what was up but we'd intentionally kept Liz out of it knowing how she would react to Allen. We told her that we had something special planned and if she wanted in on it. It was yes or no up front with no details. Naturally, wanting to get her new found freak on, she said yes. Jen had caught wind of it and wanted in on the game but I had to turn her down since there was going to be enough people there to begin with.

Luckily, there was a wooded park between Kim and Liz's house and Allen's house. So, I got the sisters lined up on the back porch both wearing high heels and black trench coats with nothing on underneath but the lingerie of their choosing. Then I put the blindfolds, collars, and leashes on them. I shoulder my bag of tricks and then pick up my end of the leashes. A single tug on the leashes and they were obediently following me. Kim was turned on at the prospect that I was now leading them to Lord-knows-where like this.

Liz, on the other hand, was a bit uncertain but she followed along anyway. After the first block and with no one spotting us or shouting at us as to what the fuck we were doing, she started to relax. When she realized that I was taking them through woods, she was starting to get into it.

I led them straight though towards Allen's house. I didn't even bother going to the front door. Instead I went around back to where the tree house was at. Think the awesome tree house out of The Sandlot and you got a good idea what Allen's was like. It was large enough for five young adults with room for possibly a few more in there. Allen and his old man built this thing to last for a few generations and the tree was sturdy enough having survived a few severe storms during my life. Hell, we had a tornado rip by the town one year and that damn tree and the treehouse stood tall like a giant middle finger to the storm.

Rumor had it that his parents camped out in it while Allen was away at college. I can't say that I blame them. I'd do the same thing.

I march the ladies up to the ladder and pull on the rope that's attached to the bell up top. Above me, the trap door in the floor opens up and there's Allen looking down at us. His eyes go wide when he sees that I have the girls with me as if he wasn't expecting me to pull through on this. I put my lips to my fingers for him to keep his mouth shut and he nods. I take Kimmy first and put her hands on the ladder. "Climb up. There is someone at the top to get you." I tell her. She nods and its up she goes. She's slow as she's blindfolded but she makes it. Then it's Liz's turn, and finally I go up the ladder and we close the door behind us.

Allen had just stood the girls off to one side and I give him an admonishing look. "Let me show you how it's done, my friend." I order the girls down to their knees onto the open blankets and sleeping bags they were standing on and they do so obediently. Then I tell them to take off the trench coats. They do in almost perfect precision; shucking off the coats and then placing their hands down on their knees as they await my next command.

"Holy fuck..." Allen breathes. I'm sure he's thinking that he's died and gone to heaven. "Dude, when my sister is old enough in a year you can come over and fuck her anytime." He says. I swear that he's going to cry with joy.

And yes, I did take him up on that. Don't get ahead of the story, okay?

"Holy shit," Liz pipes up when she hears his voice. "Is that Allen?" Her distaste is as evident as Kimmy's was.

"Hey, you agreed to this," I pointed out. "Don't like it then take the blindfold off, put your coat back on, and go home."

Okay, I have to admit that Allen is a bit of a perv when it comes to women. The reason why he's regarded as such a sleaze in our community is that he's been busted, on multiple occasions, of being a peeping tom. Since the 6th grade on, he's been caught in more women's locker rooms than I can count.

To be fair though, that's only because he hasn't learned the delicate art of not getting caught. He's really great with the ladies once he has a chance to know them better which was why I covered for him getting a blowjob from a cheerleader that one year during the State Playoffs. And to continue to be fair; I'd probably be considered just as much of a sleaze and a perv had I been caught peeping right alongside with Allen. I just had the good sense to get the fuck out of there when I knew my luck had run out.

"So, do you really want to miss out on tonight's events? Or do you want to watch me do my thing?" I ask Liz. I know that Kim is still with me on this. We'd talked about it and I'd let her in on a few secrets regarding Allen. She lightened up once I told her details and agreed that Liz wouldn't do it unless it's sprung on her. "The only stipulation that Allen has is that he has to let you two watch when the real show begins."

That got Liz's attention as she'd heard what I'd done with Mr. and Mrs. L. She'd even lamented afterwards that she'd missed out on it. Now she was here and Jen wasn't. Liz shook her head. "No, I don't want to miss out on this one. I'll stay." She said with an odd mixture of resignation and determination. I gotta hand it to her; she is a trooper when it comes to pushing her boundaries... well, at least now that I've been let loose anyway.

"Awesome, now you two, drop to all fours, and lay your heads down on the benches that'll be about a foot or two in front of you." I tell them. They shuffle around so that their rumps are facing me and Allen. They find the bench I was talking about with no problem. I gesture to them. "Your choice, my friend."

To give him credit, Allen didn't immediately drop trou and start banging Liz like I'd half expected him to. He did start with her, though. Liz was wearing a matching black satin bra and panty set with a simple pearl string necklace. Allen took his time feeling her up and his hands slid up to cup her breasts and give them a little squeeze. Liz shuddered under his touch but was a good girl and stayed in her place. "Nice collar; it goes well with the pearls," he muttered into her ear before nipping at it. He gave her covered pussy a feel before moving over to Kim. Liz actually let out a whimper and tried to get him to touch her again by lowering herself down and sticking her ass out even further for him. But, despite her newfound arousal and willingness, he still moved on.

Kim was wearing what I like to call the 'bridal package'; corset top, garter belt, hose, and panties, all white lace. It went nicely with her new white collar with the sparkly faux-gems. Allen paused, giving me a questioning look since he knew that she was my girlfriend now. I'd been sitting back against the wall watching with my arms crossed and I gave him a 'go ahead' wave towards her. I'd be getting enough action as it was tonight with two MILFs and so had no problem granting permission. Allen gave her a once over as he did with Liz and then pulled back. He looked unsure of feeling up my girl in front of me and I highly suspect that he wanted to get back to Liz in a hurry as he moved back over towards her.

Liz let out a gasp when he crawled up behind her and yanked her panties down to her knees. He unbuckled his jeans and whipped his cock out and drove into her. "AH!" Liz cried out, arching her back as he spears her. She then moans and melts into the bench as he grabs her hips and starts to roughly fuck her. I think that Liz wasn't expecting him to be in the 'well hung' category and it took her off guard.

I call Kim over to me. She fumbles around a bit but ultimately find her way over to where I'm sitting. With her blindfold on, she can hear Liz and Allen rutting around but they can't see them. Kim tries to push her blindfold up; I gently push it back down as I guide her under my arm. "Ah, Ah, Ahhhh," I tease her. "Just listen, while we wait." She gives me a pouting look but settles under my arm. I reach down and idly play with her small tits through the fabric of her lingerie while I watch Allen pound the hell out of Liz.

Liz is pushing back against the wall in front of her while Allen is grabbing her hair and plowing into her repeatedly. He's growling obscenities at her and outright hate fucking her (can't blame him, really. After all, I did a hate-fuck with her too) while she's letting out low guttural moans and grunts each time he rams his cock home at a rapid rate. The slapping of skin against skin becomes the norm and the smell of their sex fills the air in the tree house. Then Allen lets out a low howl and Liz screams, biting her lower lip to muffle her voice as she cums hard. Her initial squeak, though, had spurred me into action to cross the distance and slap my hand over her mouth to keep her quiet before looking around outside the windows to see if anyone heard.

AlexClayton
AlexClayton
2,105 Followers