The Conquest Club Files 11

"See, here's the thing, Liz," I tell her, my voice going serious as I look down at her head in my lap. "I knew that you were screwing around behind Gerry's back but I never said a damn word because I valued my friendship with him more than you obviously did. AH!" I pull back with the paddle and hold up a finger to shut her up when she perks up and opens her mouth to say something. She closes her mouth immediately and allows me to continue. "I want to know why you cheated on Gerry in the first place."

She blinks in shock at me, her mouth opening and closing as she tries to come up with an answer for me. "I... I don't know. Why does it matter? That was with Gerry and I'm with you now."

SMACK!

"OW!" she cries out, reeling back from the blow. I caught her right across her ass with the paddle. She rubs her ass and now gives me a murderous look. "That fucking hurt, you bastard!"

"Anytime you want me to stop, say the safe word and go to my room," I glare right back at her. "I'll call Gerry and Kimmy to come and get you along with some clothes and you can leave." To show that I'm serious, I unclip the leash and sit back to allow her to go if she wants. "Just know that this won't continue between us past tonight because I don't want to have to be looking over my shoulder all the time, or be paranoid all the time, that my steady girlfriend is cheating on me or not."

"That was over a year ago!" she protests, clearly angry at me. "I haven't cheated on you or anyone else since then since I haven't even been formally attached to anyone!"

"What's the saying, Liz?" I ask her. "Once a cheater, always a cheater. If this is going to continue to be a thing between us," I wag that same finger between the two of us, "then I don't want any fucking secrets going on. You wanna fuck the whole neighborhood? Fine. Just tell me when you do it, okay? So, back to the matter at hand; why did you cheat on Gerry? And please don't lie to me because I want to get this out in the open and be assured that you're never going to go behind my back to screw someone like mother-fucking Marcus and his cronies!"

I don't think that Liz could've been more stunned even if I'd slapped her across the face. It was a dark mark in her history that I knew that she would've sooner forgotten instead of being reminded of it. She'd been a drunken mess back then and had actually been going to AA for it after Gerry dumped her and put her in her place. But this was the first time that someone was making her face what she'd done. One of the reasons why she'd been bouncing between me, Gerry, a few guys from our graduating class, and every other DILF in the neighborhood is mainly because no one wanted to commit to a relationship with her. But I was willing to go the extra distance with her which is why we were here, doing this, tonight. "Come on, Liz," I gently prod her. "Confession is good for the soul. Get it out into the open. Wash away your sins and be cleansed." I then smile and waggle the paddle in my hand. "And be properly punished for it."

She later told me that there were at least a dozen platitudes and half truths that she'd been prepared to tell me that night but then she'd ultimately decided that it would've been better to say it all out loud. That, and she knew that I'd read her diary. That night when Gerry jumped her mom on behalf of her dad, he'd shown me Liz's now infamous diary. So I already knew her reasons but I wanted to hear them from her mouth now. She looked down at the floor for a moment, contemplating what to do; say the safe word, opt out, and be branded a cheater for the rest of her life? Or, confront the truth, get it out in the open like I suggested, and move on with her life. Liz let out a long, defeated sigh as she came to a decision. She'd even confessed that she'd been tempted to say her safe word but also decided that this issue was going to hang over her head for the rest of her life unless she got it all out now and that was something that she didn't want.

Now if you'd asked me, I would've bet good money that she was going to hang on to her pride and walk out on me right then and there. After all, she was the one regularly fucking me and she could've challenged me to find a new girlfriend but I also held cards in this hand in that ever since Gerry arranged for me to fuck her AND Kim in my treehouse that fateful night, my stock in datability increased even if I'm a bit nerdy, geeky, and not looking like a Greek God like Gerry. At best, I've been described as looking like Robert Downy Jr back in the days of his early acting... like Weird Science or Tuff Turf RDJ instead of Iron Man RDJ. Maybe one of the Tri Lambs from the original Revenge of the Nerds might be more appropriate.

Anyway...

Liz shocked me as she slowly crawled up onto the couch and draped herself over my lap with her ass sticking up on my right side for easier access. She then folded her hands behind her back as she took another deep breath to steady herself. "Punish me," she said in a hollow, sober, and somber tone, her voice hitching a bit. "And don't hold back, please. I deserve it." She looked back over her shoulder at me and I was shocked again to see tears in her eyes already. "Allen, please. Spank me hard." In that moment, I think that we truly understood each other.

I slowly nodded as I rested the paddle against her ass and my hands down onto her crossed wrists to keep her from covering herself once this started. "Why'd you cheat on Gerry?" I ask her. Then I reeled back and let her have it once with the paddle. The crack echoes in the apartment. The blow was so hard that she rocked in my lap.

"AHHHHH!" she cried out, her body arching for a moment before she then buried her head into the sofa cushion. She sobbed for a moment before rolling her head to the side so I could hear her. "I'm... I'm sorry that I did..." she blubbered. "I was drunk... I was lonely... I hated the fact that we were in separate colleges..." she said as she cried.

Yeah... close, but we're not quite there yet. "Why'd you cheat on Gerry?" I repeat before spanking her hard again with the paddle. It makes another resounding crack in my apartment and I start thinking that I might need to take steps to maybe soundproof this place.

Liz cries some more into the sofa before turning her head to answer again. "I was jealous!" she wailed. "I was... so... jealous of him! Even in high school girls flocked to him! I was jealous! I was insecure! I hated competing for him!"

"Even though he had eyes for only you, you ungrateful bitch?" I say incredulously and let her have it again with the paddle.

"YES!" Liz yelped and cried some more. This was good therapy for her, I could tell. She was baring her soul and crying all of her tears out over her past relationship with Gerry. "Yes..." she mewed. "I am an ungrateful bitch... I deserve this... I didn't seriously think that he was going to stay with me and so I cheated on him before he could cheat on me." It was a stupid reason, and I let her know that with the next smack of the paddle on her now reddening ass. "YES!" she cried again. "It was a stupid reason... I was insecure... I was stupid about it... I was scared... I lost my self esteem over it... I turned to drinking as soon as I was old enough to. I'm sorry!" she wailed.

"Why'd you cheat on Gerry?" I ask her again as I spank her a fifth time. "He'd been nothing but loyal to him and all he wanted to do was get a little bit kinky with you!" I say a bit louder than I had intended even as I wallop her ass a sixth time.

"I was afraid of doing it!" she says after her crying and kicking fit. "I was scared to try it and while I was drunk I slept with Marcus and his friends," she confessed, body shaking as she sobbed. I'm sorry! Oh God I am so sorry!" Three more spanks later and she was confessing everything from cheating on tests back in elementary school to being the second gunman on the grassy gnoll. She'd even confessed to becoming a Goddamn Karen because she was so desperate to hang onto Gerry just so that she could have a cushy life with him when he got drafted.

Ouch.

I put the paddle down and pull her up so that she's now sitting curled up in my lap and just hold her while she lets it all out. Honestly, I think that moment of tenderness made her cry even harder than the paddling did. She buried her head into my shoulder and just cried and wailed, all the while mumbling what a miserable human being she had been, and that she'd deserved to lose Gerry, and she deserved to be punished like this. I give her all the time that she needs and just hold her until she's ready to talk. Once she's stopped crying, she looks up at me with her tear-stained eyes, slides her hands up either side of my jaws to cup my face, and kisses me softly on the lips. "I'm sorry," she croaks out in a hollow, but genuine tone. "I don't deserve you... I don't deserve Gerry... I don't deserve anything after what I've done." She pauses again as she looks down for a moment and then back up at me. "And I'm sorry for my comments I made about you not being a real man. It was uncalled for.

"Liz," I say softly, kissing her again and holding her close. "I really like you. Hell, I think that I might even be in love with you. Just... let's be honest with each other, okay? I like what Gerry has been doing. I want that. I want that with you. Now, I'm never going to be as rich as he's going to be, or smart as he is... or you are for that matter... but I can at least guarantee you that I'll be a hard worker and will be able to at least keep a roof over our head and food on the table. That's all that I can be, hun."

Tears well up in her eyes again and her lower lip is trembling when she looks at me again and then kisses me. "That's more that I deserve," she whispers as she curls up in my lap again and we just sit there cuddling for some time. After a while once she's calmed down some more, she slides off of my lap and positions herself down between my knees again. This time, though, she takes my cock into her hand, stroking it back to life. "I'm a dirty, cheating whore, Master," she says, grabbing the paddle and handing it to me. "Please punish me again, Master, while I properly thank you for showing me the error of my ways." With that, she then looks up at me as she takes my cock into her mouth and gives me one of the most amazing blowjobs ever.

I oblige her in her request, but I'm a bit lighter on the paddling this time. The entire time she keeps her gaze locked on mine, even with tears welling up and then streaming down her burning hot cheeks. I don't know what it is about a crying woman going down on me, this being a first for me, but it's really fucking hot. She wiggles her ass slowly back and forth, giving me a cue that she wants the paddle again. I don't keep her waiting. I smack her ass with it a couple more times and she groans lustfully all the while sucking on my cock even harder. She whimpers and moans under every blow, bobbing her head expertly up and down my shaft while maintaining eye contact with me the entire time. I notice that her arms are pushing her breasts together as her hands are down between her legs now, no doubt playing with herself as she's being punished. I also remember that she still has the butt plug up her ass and that's no doubt contributing to it.

"God... I'm gonna blow!" I warn her as I roll my head back and lean back on the sofa. Liz's head looks like a fucking bobble head as she's now jerking her head up and down my cock rapidly. She pauses in her own masturbation for the moment to grab my hands and plant them on the back of her head before going back to it. When I cum, she locks her lips around the base of my shaft and holds it there. I feel her throat contracting as she starts to swallow the thick ropes of my cum that's now shooting into her mouth. Even in my orgasm filled stupor, I get what she wants and I hold her head down to make her drink every last drop of it down. She shudders and moans a moment later as she fingers herself over the edge while swallowing my seed, moaning the entire time.

Once I'm spent and my grip on her relaxes, she continues sucking me off, bobbing her head up and down a couple more times as she cleans my cock up with her lips and tongue before pulling back and kneeling submissively at my feet, looking at me expectantly. "Is Master ready for a shower now?" she asks lustfully.

"Yeah," I nod in agreement as I slowly get up off the couch. I reach down for her and she takes my hands and allows me to help her to her feet. "I guess that we should get you cleaned up, huh?"

Once in the shower we make out some more, soap each other up, and I'm sure to use lotion body wash on her ass and thighs to soothe the ache that she's got to be feeling. At the same time, I part her ass cheeks to grab the base of the butt plug to ease it out of her. Her hand shoots down to grab my wrist. I look up at her, eyebrows up in surprise, and she gives me a wolfish grin. "No, Master, please, fuck me one more time with it inside before you take it out."

What's that saying that Gerry likes so much? Whatever the lady wants?

I share her smile as I stand back up, my cock already getting hard at the prospect. Liz turns from me, leaning against the wall of the shower, under the spray of the water, and sticking her ass out towards me. She spreads her legs slightly for stability within the tub as I reach under her, spread her open, and jab my cock up into her. "Ohhhnnnnnghhh..." Liz grunts and moans at being double penetrated once again. I slide my hands around her to grope her tits as she moans and whispers her pleasure at that. "Oh yea... fuck me like a little whore Master... Play with my tits... they're yours..." she breathes. As I'm fucking her, she's pushing back off of the wall against me. I can feel the butt plug inside her again, now moving in tandem with my cock as the base of my pubis is pushing it into her every time I thrust. This time Liz cums first and I feel her shudder once again as the orgasm overtakes her so much that I have to hold her up. It takes me a couple more thrusts since I've already cum like three times tonight, but I get there and soon my cock is throbbing deep inside of her.

After that, we clean up again, dry off, get the plug out of her and the collar off of her, and head to bed for some much-needed sleep while wrapped up in each other's arms.

The next morning I wake up to a massive hard-on that's already being worked on by Liz's mouth. I also notice as she's giving me a blowjob that she has her collar back on. Funny... I don't remember putting it back on her. Did she do that herself; I wonder? The thought then becomes a moot point as I groan and cum hard, not even having a chance to warn her. She seemed to be ready for it as she deep-throats me again. drinking it all down. Once I'm done, she pulls back, smiles at me, and kisses her way up my body to give me a peck on the lips. "Good Morning, Master," she says cheerily. "I hope that you enjoyed your wake-up call."

"I can get used to that," I moan as I stretch. I then hook her collar. "We did take this off of you last night, right?"

"Mmm hm," she nods. "I put it back on while you were still asleep." She pauses. "I want to make a new rule for us, Allen. We already have the open communication rule that we established last night about telling each other who we're sleeping with, so I guess this is Rule Two then. Whenever I wear this collar... or any collar... for you, I'm your little slave until either you take it off, or I say my safe word and take it off myself." Liz practically purrs as she runs a hand up and down my chest as she's saying this. "I'll give myself totally to you for the duration to fuck and punish however you want to. But I put it on when I choose and you still have to take care of my basic needs, you know, like bathroom breaks and feeding me and everything like that."

The rules make sense to me and I'm nodding as she's talking. "I think that I can agree to that," I say as I slide my hand down her back to cup and squeeze her ass, making her shiver and squeal at that. "Before you go total slave on me for the rest of this weekend, can I ask why you're doing this all of a sudden?"

"What I said last night was true: I was being a bitch to Gerry for all of those reasons and yeah, I know you've read my diary and knew of the secret BDSM fetish I had back then," she admitted. "Yeah, part of me wanted to hurt him before he hurt me... I mean hell, the man dominated women just by looking at them and he didn't even fucking realize what he was doing at the time... the bastard..." she muttered that last part under her breath, but I could understand the sentiment. I felt the same way about him at times. "But part of me was actually wondering if he'd ever get the hint at my brattyness... ya know, the whole act that I'd done with you earlier this week? But Gerry, God fucking love him, was goddamn clueless until my little sister had to spell it out for him."

"Well, to be fair, we're guys," I said with a smile. "Subtle hints don't work, obvious hints don't work, obscure hints don't work, fuck, hints in general don't work. Ya gotta spell it out for us sometimes."

Liz lets out a light, airy laugh. "Yeah, I know that now and I promise to be straightforward with you.

"Likewise," I agree, and we kiss passionately. It's the start of a beautiful relationship for us.