The Conquest Club Files 15

"Lack of a degree?" I shrug.

"We might need to change that," he harrumphs, and I see a hint of a smile grace his lips as he shuffles the cards and deals the next hand.

The next hand, I lose and all of us guys lose our shirts... literally. Jessie, now naked, is immediately targeted by all three guys for kisses and groping while I make a futile counter of paying for one good stroke in and out of Sofia and Betty. I've now officially fucked every woman at the table even if it was a once in-and-out into their pussies. Zander gets revenge on me by paying for me to take off my shirt and I respond in kind. Tom and Conner get in on that by paying for each other to take their shirts off. Now the ladies get more touchy-feely as Betty comes up behind me to rub my neck and run her hands down the front of my chest while resting her breasts behind my head... the bitch. But, it was Tom's deal and he called Texas Hold Em so I managed to bluff my ass off to a win in that one while holding a lousy pair. Since people have been paying chips like crazy the past two hands, I got some coin to spare.

I start eyeing the toys since I have to get Betty, literally, off of my back. I drop fifty into the pot and go for the toys, finding a pair of handcuffs and a hitachi. I cuff Betty's hands behind her back and make her sit on the bulb of the hitachi, turning that fucker on high while it's nestled between her legs. "OH! You are a cruel man!" she exclaims as she then moans loudly amid the high-pitched buzzing of the toy. Damn, that's a turn on watching her moan and writhe in her chair like that. Zander is too distracted at his wife's increasingly flushed chest, a sign that she's close to orgasm, to pay attention to the next hand. So I take him to the cleaners on that hand and then drop enough chips to get a ball gag, a butt plug, and a pair of nipple clamps for his wife. By the time I have her decked out and sitting back down on the hitachi, she's jerking and shaking in her chair from an intense climax.

"Shit," Zander says in disgust as he throws his cards down and leans back in his chair, crossing his arms, waiting. Tom and Conner join me in my victory whoop. High fives are exchanged all around. Zander smiles and applauds me in my moment of victory before gesturing to Betty for me to do whatever I want to her.

Since I made her cum, I get first shot at her. While I stand Betty up and bend her over the table, I drop trou, spread her open, and jam my throbbing hard cock into her, making her groan deeply. I then sink my hands into her hips and happily pound away. Off to my right, Jessie, Sofia, and Audrey are making Zander strip and the three of them take turns giving him a single blow but not doing enough to get him off. Tom and Conner simply sit back and wait with big smiles on their faces. "God Damn," I moan as I pound Betty from behind. "I've been waiting all night for this..." I say with a tightness in my voice.

Jessie, having slept with me a couple of times already, knows that tone. Her head pops up from Zander's lap as she looks up at me in alarm. "Allen! NO!" she cries out

"No... no..." Zander says smugly, "let the boy have his fun."

It's too late for me anyway. My cock explodes into Betty with such a thunderous force that I tune everyone out. Tom and Conner laugh and exchange high fives while Jessie shakes her head in bemusement. "What?" I ask when I finally come down off of my climax.

"We're now second place losers since you came inside of her," Jessie says, still shaking her head while rolling her eyes in a 'I can't believe this shit' motion. I think about the rules amid the guys' laughter. Shit... they're right. It doesn't matter how you cum, even in victory. If you're not the last couple to get off, then you lose the game.

Ah well.

"Well worth it," I say as I let Betty go and sit back down. "I regret nothing."

Zander is on Jessie in a heartbeat, grabbing her head and dragging her face back to his crotch. This time when his cock sinks into her mouth it stays there, and he forces her to deep throat him until he cums. He's allowed to with no penalty since he and Betty had already lost. Betty manages to collect enough of herself to get all of the toys I'd put on her and in her off, getting help from Audrey to get the cuffs off of her first. "I'll take care of stud muffin over here," Sofia says with a wicked smile on her face as she gets a few things of her own from around the room while Tom and Conner line up to take their turns banging Jessie.

"Do your worst," I tell Sofia when she comes my way.

"Promise to be a good sport about this and not resist?" She asks with a pointed look. It's a fair question since I am young, very much male, dominant, and hetero. I nod because I'm a bit curious as to what she has in mind. She starts by handcuffing my hands behind my back behind the chair so I can't move much. Then she takes one of those vibrating eggs attached to a wire, lubes it up, and, after some maneuvering, manages to get it slid up my ass just a little bit. It felt weird at first but when she turned it on, holy fuck did I get a hard-on back. Then she goes to her knees before me and notices my cock ring. "Naughty, naughty," she says as she rolls it off of my cock and then gives me a blowjob to get me even harder.

Well, if this is torture, chain me to the wall... oh, wait... they already got me tied to the chair.

Unfortunately, I didn't notice what she had as her final toy. It was one of those sheath cocks from Bad Dragon, that, while she was blowing me, she was putting lube into. She pulls her mouth from my cock and slips that thing onto me so it looks like I got a fucking werewolf penis. It even had a loop at it's base to go around the base of my balls. Hm... okay... interesting so far. I then give her a questioning look as she then lubes the outer part of this thing up, straddles my lap, and then sinks her pussy down onto it all the way, gasping the entire time. Sofia gives me an evil smile now as she drapes her arms over my shoulders, puts her tits into my face, and starts riding me.

That is when I find out just how fucking cruel Mrs. Lane is. She's gasping and moaning as she rides the monster cock that is around my package. The problem is that I CAN'T FEEL A FUCKING THING! It's like I'm wearing an uber-condom that totally desensitizes you. I grunt and groan as I try to get some sensation... any sensation... out of it and I can't get any. "Oh you are a cruel, fucking bitch," I tell her and her response is to give me a hungry kiss and ride me even harder.

I swear I will have my revenge.

To make things even worse, Audrey and Betty come and flank me while all three of their husbands are screwing Jessie senseless. Audrey playfully, gently turns my head towards her and sticks her left tit into my mouth. I moan and suck on it and then Betty does the same thing, giving me her right tit. It is true, apparently, that word has indeed gotten around that I am very much into breasts so having three sets of them in my face, while being fucked while I can't feel anything, and tied up so that I can't touch them, would pretty much be my definition of hell. But then I notice Audrey and Betty trade a wicked glance with each other and without a word, they then bend over and each suck on one of Sofia's breasts while reaching down between her and me to finger Sofia. "THIS ISN'T FAIR!" Sofia then cried out as the two of them then forced her to cum while she's riding me. "NNnnnggguuunnngh..." she grunts as her body starts trembling and shaking on top of me as she climaxes.

I hear Conner crow with triumph. "HA! You lose again Tom!"

"At least it's second place this time," he says defensively.

"Get this damn thing offa me so I can fuck her properly!" I cry out from in between the three women. They release my handcuffs and I grab Sofia, who's still trembling from the orgasm inflicted upon her, and lay her out on the poker table, sending cards and chips flying everywhere. I pull out of her long enough to strip that fucking cock sheath off of me, put Sofia's ankles up on my shoulders, and drive back into her. She grunts as she's penetrated again and just lays there limp, letting me take her until I fuck her hard and fast until I cum inside of her this time.

True to their word, the night devolved into a straight up orgy after that. Partners were swapped on a regular basis. Twosomes, threesomes, and foursomes formed. I got my cock sucked by all four women at one time or another and one time I had Jessie and Audrey kissing each other while my cock slid between their lips and another time I had Betty and Sofia doing the same thing. Conner and I double teamed Sofia while her husband watched us. Zander and Tom double teamed Jessie at one point. We all gangbanged Audrey at another point. It was a blur after that as we had our night of debauchery at the end of which everyone went back to their respective homes with everyone looking forward to part two the next night.

Jessie, however, led me upstairs to the master bedroom and on through to the master bathroom. We hopped into the shower and cleaned each other off amid making out with one another. "I certainly hoped that you enjoyed tonight, Allen," she said with a smile. Her hand was already down between my legs, stroking my cock. "I hope you have at least one more in this thing for me?" she asks sweetly.

"Mmm... but of course," I murmur as I pull her close and kiss her again. I grind up against her and once I'm fully erect, we cut the water, get out, dry off, and head to the bedroom. Unlike Audrey and Conner, John and Jessie don't have any hang-ups about having partners in their bedroom. The moment we're at the foot of the bed, Jessie does an about face on me, kisses me, and we fall together onto the plush coverings. We have to sidle up the bed a little bit more but once we're in position, I waste no time in shoving my hardness into her, not caring how many loads by three men have already been blown into her. Mine will be the last tonight and like a conquering hero, I buck against her, driving my cock into her hard and deep.

Jessie arches her back and lets out a high-pitched scream so loud that I wonder if I'd hurt her. It's to the point that I look down at her, while my cock is still buried in her, and ask her if she's okay. "Yeah..." she says with a shaky nod. "I've just been fucked so raw tonight that I'm really sensitive... it's okay... really... but the mixture of pain and pleasure... ohmygawd... it feels oh soooo good," she explains while panting. Then she looks up at me with a goofy smile. "Do it to me again," she breathes huskily. I give her another single hard thrust and she does it again, this time with her clutching my biceps with her hands and wrapping her legs around my waist. "More!" she screams, and I thrust again. "OH! More... More... MORE!"

I'm now happily fucking her while she's screaming her pretty little head off. I then get the strange, yet ultimately good feeling of pleasure and pain. I lost count how many times I fucked all four of the MILFs tonight at the party and the head of my cock is feeling a bit, for lack of a better term, rug burned. Every time I slam into her cervix, I feel that jolt of pain on the tip of my cock but at the same time feel the wonderful pleasure that accompanies it as my cock moves in and out of her. She then plants her feet down and lifts her hips to meet my thrusts. Soon we're just reduced to two sweaty beings gyrating against one another while we grunt, moan, and scream. We're not fucking, we're outright rutting on her and her husband's bed. When she finally orgasms, I don't realize it at first until her entire body tenses up and seems to freeze in place while she trembles from head to toe. She's already screaming with every thrust so when she screams with the orgasm, I honestly can't tell the difference. But, I do feel her pussy fluttering around my cock and that's what sends me over the edge so hard that I'm pretty sure that I black out and don't wake up until later when I find out that I fell asleep with my head on her breasts and my cock still inside of her.

One of the best orgasms in my life.

And the start of me making the rounds in the neighborhood of the MILF Blondettes. Maybe this fall and winter won't be so bad after all.