The Conquest Club Files 09

"Oh I'm sure it's only the second level for Lust if you're unrepentant," she laughs. Delilah then has a wicked look on her face as she eyes me. "But, speaking of confessions, I have another one to make to you... if you're up to doing it to me, that is?"

"I'm up for anything that you want to do," I tell her with a grin of my own. If she wanted me to lay her out on the altar in the sanctuary to fuck her at this point, I would've been all for it. "What do you have in mind?"

"Well, I've been punished by the Mother Superior before and some of the elder nuns whenever I've slipped up, both in my Catholic Summer School and in my... erm... private studies. Corporal Punishment, to be exact. Back in high school I started feeling... uh... well... tingly down there," she explains, pointing down to her pussy with my semi-flaccid cock still inside of her and is now getting harder at where I see this 'confession' going to. "When I was at church recently, I intentionally did something bad for the Nuns to punish me again and again I felt it. I felt... aroused. Then, when I heard about you and your... uh... activities... that's when I decided to call you up so that I could explore these feelings even more." That's when she turned her head to look over at my bag. "I hope that you brought something for that along like I'd asked you over the phone."

Now I'm smiling like a kid on Christmas. "You sure that you want me to paddle your bottom?" I ask her, sliding my hand down to cup and squeeze her ass for effect.

She nods. "Please? If you don't mind? While I... uhm... confess?"

"My pleasure," I tell her, letting her go so that I can shuffle off the bed. The rational part of my brain is screaming that I'm going to slow roast on a spit while Satan and his demons laugh maniacally around me. The other part of my brain says to shut the fuck up and enjoy this while it lasts.

"Be right back," Delilah tells me as she rushes back to the bathroom. I hear the faucet turn on and the splashing of water as she cleans herself up a bit. While she's doing that, I get my padded leather paddle and a couple pairs of leather cuffs, just in case. If I'm going to go to hell for this then I'm going in a blaze of fucking glory. I want demons chanting my name when I go. "Okay, I'm ready," she says, coming back from the bathroom. I do a double take as I'm getting my toys out. She's still naked but she's wearing the coif and collar... the whole headpiece of her nun's habit... and has her hands folded as if in prayer with her rosary wrapped around her wrists and the cross hanging out from the tops of her hands to dangle in front of her knuckles.

I swear that I just fucking heard Jesus facepalm and Lucifer cackle as my cock stiffens to a hardness that I never thought possible before. I'm pretty sure that they both have 'Theme Park' in mind for me once I'm damned to eternal hellfire.

"Do you like what you see, Gerry? Do you think that I'm an attractive woman?" she asks me as she walks back to the foot of the bed to kneel on the floor with her forearms resting on the mattress. All I can do is nod mutely with my mouth gaping open like an idiot. She smiles brightly at me over her shoulder before turning to face the bed to adopt a serene, pious expression on her face as she takes a deep breath, closes her eyes, and exhales. "Forgive me, Father, for I have sinned..." she starts out before going into how long it's been since her last confession and everything.

More like; forgive me, father, for I'M about to sin... a lot... I think wryly as I step behind and off to the side of her, dropping my paddle down to caress her ass with the soft velvet side of it. I wonder what the rap is for spanking a nun? I wonder. Then again, nuns do it all the time to other nuns and their souls seem to be okay with it. Delilah goes through her routine about listing off everything that she's done wrong in the past week, including what we've just done in bed, before finally finishing up with, "I deserve to be punished, Father."

Well, that's my cue. I rotate my wrist back and around to wallop her across both ass cheeks with the paddle. She jerks up a bit before settling back down in her relaxed kneeling position, cooing the entire time. "Oooooh... Thank you, Father," she moans. "Harder... please..." Hm... Okay. I like giving the ladies what they want. I wind up further back and give it to her across her backside, aiming just a little bit lower to catch more of her... cushioning. Hey, she's got a nice, round ass and plenty of target area. She jerks, moans, thanks me, and then says "Harder... Please..."

Now I flip the paddle so it's on the leather side as opposed to the velvet side. Harder she wants, harder she gets. I smack her hard on her ass, this time the spank reverberating off the walls inside of the small room and leaving a red mark on her bottom. Delilah jerks, moans even louder, and settles back down. "Thank you, Father," she moans. "More..." Well, now that I know where she wants it at, I give her another. I'm careful enough to spread out the blows up and down her bottom and to give her ample time to recover from each one. But each time she moans, thanks me, and asks me for more. I honestly lost count how many times I spanked her but I do remember losing count after twenty or so and that her ass was glowing red even in the dim light of the room. Finally she put her head down on the bed between her forearms. "Thank you, Father, I'm ready to receive you now," I hear her muffled voice say.

I toss the paddle aside and kneel behind her. Delilah spreads her legs for me as I shuffle up next to her. I can feel the heat radiating off of her skin. She's breathing deeply, with her chest heaving beneath her. I bring my cock up to her now dripping wet pussy and ease myself back into her. "Oooohhhhhhhh..." she lets out the long, low groan as she feels me penetrate her again. My cool thighs are now resting against her burning hot ass from the paddling. I wrap my hands around her again to cup her breasts, gently playing and tickling them with my fingertips while occasionally tweaking her hard nipples. Once again, I take my time with her by slowly pushing my hips back and forth into her. "Harder..." she sighs. "Plow into me deep... plant your seed within me..." she moans.

Transferring my hands back to her hips, I grab her and start fucking her hard and deep. So hard, in fact, I'm slamming into her cervix. She goads me on even more with her moaning and groaning. This time I'm the one who comes first. "EEEEEAAARGH," I ground out as I lose control, my cock now thundering deep within her. Ropes of my cum is shooting up into her and my cock is throbbing endlessly inside her pussy. I feel her clench down upon me a few moments before her pussy flutters and she's climaxing right along with me. She presses her face into the covers of her bed and screams her head off, her voice now muffled even more. Her whole body shakes again as the orgasm washes over her and I get a good view of her quivering ass and her shaking back, with that nun's cowl of hers covering her head. The thought that I'm doing a nun just makes my orgasm that much more intense.

Yeah... like I said... a special hell...

She collapses to the floor and turns to sit back against the bed. I slip out of her when she does that so I sit down beside her. We're both covered with sweat at this point in time and breathing heavily. Delilah slides a hand up inside of her cowl and takes the thing off, then reaches behind her to undo her collar and set it aside. Then she lays her head down on my shoulder. "Is making love always this good or am I just troubled for enjoying it?" she asks in heaving breaths.

"I haven't had any complaints so far," I say, leaning my head against hers. "How about we get cleaned up with a shower and then I'll rub you down from head to toe."

"Mmmm... sounds heavenly..." she purrs. She looks up at me with those pretty blue eyes of hers. "How come we never dated in high school, Gerry?"

I snorted. "Because your parents said no, wouldn't let you date anyone, and then I started going out with Liz," I deadpanned. I mean it was true; I tried to date her as I thought she was hot as fuck, but her old man nearly drove me away with a shotgun when I asked to go out with her. Seriously, had her dad said yes, I think that my sex life would've turned out a bit differently. I then let out a rueful laugh. "I get the last laugh now since I've finally got to be with you."

"Hmph..." she smiles. "It'll be our little secret," she says mischievously. Then she looks down and is cradling her belly. "Although, I wouldn't mind being a mother... a real one, that is. Procreation is one of God's commandments."

"I'm sure you will be one day," I say. She gives me a sour look and I grin. "Seriously; if your biological clock ever goes into overdrive, call me up and I'll jump on that grenade for you."

"Hm, you would have good genes; athletic, intelligent, and a libido that doesn't quit it seems," she says, noting my still semi-erect penis. "Let's go take that shower." She stands up and takes my hands. I allow her to pull me up and she's still holding my hand as we go into the bathroom. It's small and cramped with the shower being an old fashioned porcelain tub with a curtain drawn around it. Nevertheless, I clean her up underneath the spray of the hot water, clean myself up, and then we spend the rest of the time in each other's arms making out until the water goes cold.

After we dry off, we're back on the bed. I have her lay on her stomach while I proceed to get the massage oil out. I start with her lower back, butt, and thighs to soothe the sting of the paddling that I gave her. Delilah moans with pleasure as I'm kneading her butt. "Ohhhh my, that feels heavenly..." she says.

"Eh, people underestimate the value of a good butt rub," I tell her as I work my hands over one butt cheek and then the other, kneading them as if i were a baker kneading dough. Then I run my hands down her thighs to the knee and then work my hands back up to her ass in the same fashion. "We use it every day just to sit on and it gets a workout if we do a lot of walking and running. Just like people tend to neglect the legs when giving others a rub down. They're the limbs that we use on a daily basis and the ones that probably work the most on our bodies. Yet, they're the ones that people tend to forget about when giving a massage."

"Ohhhhh... well, please, don't stop..." she purrs.

By the time I'm done with her legs and I've worked my way back up to her neck, she's sound asleep. I shuffle into place beside her and pull the covers up overtop of us and just hold her as sleep finally claims me as well.

Nothing really happened the next morning aside from us dressing and eating breakfast together. As a parting gift to her before I left, a sort of early graduation present if you will, I give her a pair of white panties that has a vibrating egg and a small dildo nestled into the crotch. "If you ever need to," I search for the right words, "relieve some stress while you're sequestered away in a monastery somewhere, just put these on, text me, and let me take it from there," I tell her. "It's Bluetooth enabled, so whenever you turn them on I'm able to control it with my phone." I hold up a hand as she's about to protest. "Yeah, I know that masturbation is a sin with you all but can it really be considered masturbation if you're putting on underwear and someone else is controlling the action?" I ask her rhetorically.

Delilah cocks her head as she ponders it then smiles at me for finding her a loophole. She takes the box from me and then gives me a big hug, kissing me passionately on the lips. It's a bit awkward for me as she's wearing her full habit and so she takes off the collar and cowl to give to me. "Something to remember me by," she says happily. "I've heard that you take little trophies here and there from everyone. I think that this will be the most unique one you have."

I hold it in my hand and then eye her cautiously. "Won't this be missed?" I ask. "Don't you need this for your uniform?"

Her smile turns mischievous. "I brought an extra one for just this occasion. Give it to your girlfriends so you can relive our night together." She then gives me a playful bump with her hip. "And send me pictures."

"I'm sure sending nudes of girls acting as nuns to a real nun is another level of special hell, but why not? I'm already going there anyway," I quip with a broad smile of my own before giving her another kiss and then getting in my car before we wind up desecrating the church grounds. Fuck, I'm in it enough as it is. I might as well be putting in my application to take over Lucifer's job at this point. I toss the habit piece into the passenger seat, start the car, and drive off to her retreating, waving form.

Delilah eventually did become a mother just like she'd hoped and, to be honest, I think motherhood suits her well. She didn't even have to leave her order or anything. They just changed her status a bit and didn't make her stay in her order monastery, instead opting for a nearby home where there's other women of the order who have family. Who's the father, you ask? Well, like I'd said before; I'm the only man who's ever known her in the biblical sense, so you figure it out. We kept in contact after college and every so often she'd show up on my doorstep, Habit and all. Without ever saying a word, she'd always walk straight to my room or my little dungeon that I eventually built in my house and we'd proceed with her 'confessional' and 'punishment'. That's how I eventually wound up knocking her up. Of course the ENTIRE neighborhood looked at me suspiciously, I can't imagine why really, but I just innocently shrugged and said it was a miracle.

But... that's a story for another time.

*

When I get back home later that afternoon, Kimmy and Jen are practically bouncing up and down with glee as they want all the details and they're still in those damn Catholic Schoolgirl getup. I swear they're doing it just to torture me. They follow me into my room as I drop my bag at the foot of the bed and start giving them the run-down. Kimmy goes through my bag and finds Delilah's cowl and collar. She immediately puts it on. "How do I look?" she asks, pressing her hands together as if in prayer and looking mock pious while batting her eyelashes.

I laugh. "It's a little too big for you," I note. "But if you want to do sexy nun for Halloween next year, I'm sure we can find something for you."

"Lemme try," Jen says, taking it off of Kimmy. "I'm more Delilah's size." She puts it on and it fits her perfectly and pulls off the pious pose even better. My cock goes hard again inside my jeans and I groan painfully. Jen smiles wickedly at me as she walks over to me while wearing it. At the same time Kimmy goes to her knees in front of me, hands going for my belt and fly. Jen presses herself to my right side, my arm sliding around her waist, as she huskily whispers "Ever want to kiss a nun?" In response, I pull her head to me and kiss her roughly and deeply, eliciting a moan from her.

Kimmy, in the meantime, has my cock out and is already sucking hard on me. Once I'm making out with Jen, her hands now snaking up under my shirt, I drop a hand down onto Kimmy's head to hold it in place occasionally. I got this image of a headmaster having his way with a nun and one of their students running through my head and it just drives me over the edge even fast. "God, I'm gonna blow already," I groan painfully, trying to hold back. But Kimmy, that little minx, sucks me even harder at that. So I slammed her head into my crotch and drove my cock all the way into her mouth and let her have it. I came so hard that she actually had trouble for once keeping up swallowing. It was so much that she pulled away for air and I let her go. Wound up giving her a facial after that as I was still blowing my load.

Eh, serves her right. I did try to warn her.

But I'm a good sport about it and lay them both out on the bed after Kimmy cleans up. I eat them out to a screaming orgasm each and we wind up falling asleep with them in their outfits still.

A special hell... I think as I drift off.

*

I thought that I was done with Delilah for the remainder of spring break by God must've thought that he wanted to have one more laugh at my fucking expense.

One of the little traditions in our neighborhood is to have a pool party over at the indoor pool complex. It's an all day thing with the more adult activities of drinking and swimming happening after nightfall once the parents have taken their kids home. I volunteer during the day to be a lifeguard since they're always overbooked for this event, knowing all sorts of mischief that I'm going to get into here once the sun goes down. A lot of my conquests are there; Kimmy and Jen, of course. Elizabeth is there with her new boyfriend; my buddy Allen. Those two have become quite the pair since that night in his old treehouse. The MILF squad is there and I can tell that Sofia and Jessie have been telling of my exploits based on the number of sly smiles and looks that I'm getting from their friends. Even Mrs. C... Audrey... is giving me the eye like she's going to ditch Liz and Kimmy's dad to shack up with me real quick.

God, I love my sex life now.

But then I hear God fucking cackle in my ear as Delilah walks in from the locker room with her mom at about mid-afternoon. I did a double take at first, not believing what I was seeing. Delilah was wearing a plain, black, one piece swimsuit and a nun's cowl that was reminiscent of Kate Upton's costume in that more modern Three Stooges movie. Of course Kimmy and Jen happen to be near my lifeguard's stand when she walks in and both of them are talking about how hot she looks. I'm sure they were loud enough on purpose for me to hear them. I shoot them a glare that promises swift and brutal retribution later tonight and they respond with a look that dares me to do it while they both coyly smile and waggle their eyebrows at me. Then they dart around the pool and strike up a conversation with Delilah, no doubt trading stories and getting her side of the events of our night together. Thankfully they had the decency to wait until Delilah's mom had walked away to do it. I could only think of the slew of phone calls that I'd get from her parents... and possibly her church... if that'd happened.

I lose track of them during my rotation until later on in the day towards the end of my shift. The sun is setting outside the huge paneled windows and the crowds are starting to thin out. Delilah catches me by surprise when I'm working the deep end of the lap pool by the diving boards when she sidles up to my lifeguard chair and nonchalantly says "I want you again." I'd been bored up to that point, leaning my head against one hand. When she says that by way of greeting, I nearly fall into the pool myself. But, thankfully, I recover enough to gape down at her. She smiles sweetly at me. "Meet me in the kissing room here once you're off of your shift. I've always wanted to see what that room was like." With that, she walks off as if we'd been discussing the fucking weather.

I can't help but blink at her shapely posterior as she walks away. I know exactly what room she's talking about here and I can't decide on who I want to kill first; Kimmy, Liz, or Allen since I know the three of them had to be behind this. The so-called "Kissing Room" here at the swim complex was an out of the way supply room that was actually rarely used for actual fucking supplies. I think that they keep the holiday decorations down there and so work staff hardly go there unless there's a holiday event coming up. There were so many nooks and crannies in there that, if rumors are to be believed, up to ten couples could be in there making out and/or fucking and would never see anyone else. If local legend was to be believed, then multiple orgies among graduating classes have happened there. Knowing that Delilah was ditching her parents to go down there to wait for me made me hard and so I spent the last minutes of my shift squirming in my chair.