The Conquest Club Files 09

***

Author's Notes: If you're even remotely offended about religious roleplay and/or age play, you might want to skip this one.

***

Hunter File #0009: Delilah (Model Inspiration: Delilah G/Danica Jewels)

Age: 22

Height: 5'5"

Figure/Stats: 32B-25-34

Hair: Blonde

Eyes: Blue

Trophy: Nun's Cowl and Collar

*

If you take sexual advantage of her, you're going to burn in a very special level of hell. A level they reserve for child molesters and people who talk at the theater...

Well, Shepard Book, I swear to your God that I'm going to the special hell.

One of my friends from High School, a real, sweet Catholic girl named Delilah that I so would've dated had I not been with Liz, had heard about my exploits. Well, her life choices took her in an ENTIRELY different direction. She was about to finish her degree up at Notre Dame and then enter into an order so that she could continue teaching for the church. She was already a Holy Sister and was going to go full Nun once she graduated. So, yeah, she was wearing the Sister's Habit already while finishing up her last semester of schooling. Delilah found out about what I was up to through her parents and I'm sure that the review was not favorable coming from them. My job dropped when she called me up and expressed interest in becoming one of my 'Conquests'. Seriously, she went all Arya Stark on me. No, she didn't fucking try to kill me or anything. She did the whole 'If I'm going to remain celibate for the rest of my life, I want to know what I'm missing out on' thing.

Well, as luck, or fate, or even the school scheduling would have it, I had the week off for my trip to the NFL Combine, which I think that Tycen and I performed decently at. Hell, we were even approached by scouts from the teams that don't participate in the Combine itself; teams like the Colts, the Bears, the Browns, and the Ravens. The week after that was spring break to which we had all the time we wanted to ourselves. Tycen went back to the dorm room to spend time with his girl and I went back home for the week to spend time with my girls. Yeah, call me lame for spending spring break at home but dammit I had threesomes to attend to! Come on, priorities here!

That's when Delilah called asking me to meet her somewhere to ravish her the next evening.

Kimmy and Jen, naturally, listened in on the call and so were all hot and bothered about me committing the sacrilegious act of fucking a Nun. While I was on the call with Delilah, they zipped out of my room and over next door to her room long enough to get changed into sexy Catholic Schoolgirl outfits from Kimmy's stripper wardrobe. When they came back in their outfits, fucking pigtails and all, those two little minxes got down on their knees in front of me with their hands clasped piously in prayer and said, in unison, piously; "Punish me, Daddy, I've been bad."

So yeah... I'm going to hell.

Before I get to Delilah, I'm sure, dear reader, that you'd like to know how I handled my two girlfriends. I ordered them to both stand at the bed, cross their ankles, and to bend at the waist so that they were laying on the bed with their crossed legs dangling off. Then I flipped both of their miniskirts up to get a very good view of their nice, round bottoms with their white panties peeking out at me as the sheer white fabric covered their mounds. Couple that view with the knee-high stockings they're wearing. I went hard almost instantly. I grabbed my padded paddle and ran it up Jen's thighs up to her bare butt. Then I smacked it hard. Jen jerked, yelped, and counted out "One, Daddy." Then I did the same with Kimmy, who counted it out the same way. Both of them kept their hands clasped as if in prayer over their heads the entire time.

Once I got to ten with both of them, I made them kneel on the floor again. They did so, looking up at me expectantly, and I ordered them to undo their blouses as I stripped my T-Shirt off and undid my pants. Kimmy and Jen undid the knots where their blouses were tied at their cleavage and, as one, bared their pert little tits to me. I stepped up to them, paddle in hand. I grabbed Kimmy's head first and made her suck my cock. She closed her eyes and moaned as she wrapped her lips around my manhood as I drove it into her mouth. I let her bob her head back and forth a few times as I bent over a bit and paddled her bottom. Then I pulled back, pulled out of her mouth, and did the same with Jen. I alternated between the two of them and both of them eagerly sucked on my cock. I swear they were holding a private contest between themselves to see who could make me blow first.

"Drop your panties to your knees then present to me," I told them, pulling away and giving myself time. Kimmy squealed in anticipation and Jen giggled as they hastened to follow my orders. When they were done their skirts were flipped up over to reveal bare bottoms with their white cotton panties bunched up around their knees. Their bare breasts were pressed to the carpet and both of them had their heads turned to each other so they could watch. I went to my bag of goodies to get a couple of gemmed butt plugs. Then I knelt behind them, sliding my hand over their hairless, wet slits, making them both shudder and moan with pleasure when I touched them. "Hmmm, you both are a couple of horny sluts, aren't you?" I muse as I then start fucking them with the plugs. Once the plugs are nice and lubed up by their own juices, I pull them out, bring them up a couple of inches, and press them into place up their butts where they belong. Kimmy and Jen kick their legs and squeal as they're both penetrated up the ass. I then slap them across the bottom with my hands once the plugs are in place. "And you're going to keep these on all day now, got it?"

"Yes, Daddy," they both say as one.

I leave them kneeling and bent over as I go back to my bag and grab a cock ring to put on. I want to stay hard for this and I'm already close... and I haven't even stuck my cock in them yet. For shits and giggles I also grab some leather cuffs and cuff their hands behind their backs. I then kneel behind Jen, ram my cock deep into her tight pussy, and then grab her by her hair to yank her into an upright kneeling position. "AHHHH! Thank you, Daddy!" she gasps as I start fucking her hard and fast while holding her up by her hair. For safety and the domination factor, I slide one hand around her front to grab her left tit, squeezing it a few times, before sliding it up to rest on her collar bone just below her neck. It gives off the illusion that I'm choking her without actually doing it. "Oh yes, Daddy... thank you, Daddy, fuck me, Daddy..." she breathlessly chants as I relentlessly pound the stuffing out of her. Next to us, to our right, Kimmy looks up at us from the floor and moans pathetically as she patiently waits her turn.

"Oh God, Daddy!" Jen squeals. "I'm gonna cum! May I cum, please, Daddy?" she starts begging me. I turn her head in my hand to make her face me, look her dead in the eyes, and give her permission right before I forcibly kiss her. Jen moans deeply into my mouth as she jerks and shakes in my grasp as the orgasm hits her. She then turns to putty in my hands and I hold her upright, feeling her pussy quiver around my cock the entire time. Once she's come down from her sexual high, I gently lay her back into position with her head facing Kimmy before sliding out of her. "Mmmm... Thank you, Daddy," she purrs.

Kimmy is already shaking her ass at me when I crawl over to her. I give her a playful smack on her rump before driving my cock deep into her. "OH!" she cried out as she's suddenly penetrated. "Ohhhh... Thank you, Daddy," she moans as I then lift her upright to fuck her from behind. Just like with Jen, my pubis hits the plug and fucks Kimmy up the ass while my cock rampages in and out of her. My hands snake around and I cup Kimmy's breasts, squeezing them and occasionally rolling her nipples in my fingers as I fuck her. She's gasping in passion every time I thrust my cock into her. I feel that she's close. "Ohhh... give it to me, Daddy," she pants, "blow your cum into me, please!"

With the cock ring on, it takes me a few more thrusts. But, when I do get there, I unleash a torrent of cum up into her so hard that I swore I was going to send her into orbit. "AH! GOD!" she cries out as her body starts to shake. She turns her head to me, mouth gaping for a kiss and I lock my lips to hers, driving my tongue into her mouth and letting out a groan as my cock continues to spasm and spurt up inside of her pussy. My head swims as the pleasure washes over me. My cock is twitching hard inside of Kimmy as her pussy clenches and releases it while she comes.

"Oh... Damn..." I moan as I let her down easy to the floor and then collapse in between them. I roll to my back so that they can then shuffle to rest their heads on my shoulders and there we lay for some time with me idly stroking their hair as they moan and mew in the crook of my arms.

*

"Oh I am so going to slow roast in hell for this..." I mutter the next night as I pull up to the address that Delilah gave me. It's an old brick Catholic church that's out in the fricking middle of nowhere that had fallen into disuse... one of those things that was built at a crossroads in order to serve the bordering farming towns and villages that were within relatively close horse riding distance. This particular one came complete with the cathedral-esque main sanctuary, creepy graveyard across the street, and a small house for the priest and whoever else to live at as they cared for the place. The Catholic Church still owned and maintained the property and the current caretaker was on vacation. As Delilah wanted to come back to the area to visit family before graduation, the church allowed her to stay here to watch over the place and to do the gardening and upkeep for the week of spring break.

And, of course, it is here that Delilah wants me to deflower her at. I might as well call Lucifer and make reservations.

Delilah smiles and gives me a hug, meeting me at the door to the sanctuary after I grab my bag of goodies before closing and locking my car. She's wearing a Sister's Habit that does show off her blonde hair. Think the younger chick who wasn't quite a nun yet in Sister Act. Same concept. Once Delilah takes her solemn vows, then it's into the full getup with no sex. Then she leads me in, closing and barring the double wooden doors behind us before leading me all the way through to the house attached in the very back of the joined buildings. "It's good to see you again, Gerry," she says sweetly as we walk. "You're quite the talk on my campus. They say you might make it into the NFL this year."

"Meh..." I shrug as we're leaving the main sanctuary and the small hallway off to the side of the vestibule that connects it to the house. "I think that I'm in the middle of the pack so I don't think that my chances are all THAT great," I admit.

"Still, you did announce your eligibility, didn't you?"

"Of course I did," I scoff. "I'd be a fool not to. But, I have some job prospects should that not work out."

"Well, God works in mysterious ways," she smiles kindly at me. I wish I had the faith that she did in my NFL chances, but right now my mind is on sinning. She leads me straight to the back of the small house to the only bedroom where she looks at me expectantly. I put my bag into a nearby chair, open it up, and fish out a pack of condoms. "No," she said, shaking her head as she heads for the bathroom. "Birth control is a sin. I don't want to use those."

"So's fucking and knocking up a Nun," I counter, calling after her in the bathroom where I hear the shuffling of garments, "but you don't hear me complaining."

"No. No Birth Control." She reiterates firmly from the bathroom. "You promised me on the phone that you'd do things my way, Gerry."

"You don't want to take your Solemn Vows while pregnant, Delilah," I counter. Yeah, I know enough about Catholicism to know that. Well, truth be told, I looked it up after Delilah called me. "And what if I do get you pregnant? Then what? I'm not marrying you. I already have someone in mind for that."

"Yes, and a girlfriend who's probably going to live with you two as well, from what I hear," she said with a smile as she comes out wearing nothing but a robe, her curly golden locks now spilling down over her shoulders and back. "Don't worry, I'm off of my fertile cycle and am about to start my period at the end of the week. It's highly unlikely that you'll get me pregnant. But then again, that's part of the thrill for you from what I hear" she explains to me. I have my doubts but hold my tongue as she's not wrong. I do get off on the pregnancy risk sex. "Well, I guess that we should get to it then?" she asks as she walks up to me. She parts her robe and bares her body to me. She looks so angelic standing there that I swallow hard, unable to say anything for a moment.

"Oh I'm going to go to the special hell..." I then bemoan, not for the first time, feeling my cock stiffen inside of my pants to salute her nudity. Even so, I'm standing up and taking my shirt off, pressing my body up against hers as she tips her head back and welcomes my lips for a soft, sensual kiss. I feel her breasts press against me as I take her into my arms. I gently probe my tongue into her mouth and she moans as she kisses me back. One thing is for sure; she's done this before. After a moment of making out, I pull back and eye her. "You're not as innocent as your chosen profession would lead one to believe, Sister," I point out, emphasizing her title.

She smiles coyly at me as she lays down on the bed while I shimmy out of my shoes and jeans. Delilah beckons me to her with her crooked finger as I join her on the bed and lay on top of her. She wraps her arms around my neck even as she's bending a shapely leg along my side. "I have a confession to make," she whispers seductively to me with a smile. "I've kissed many a man before. I've even fooled around with playing with others and even masturbated but I've never gone all the way before. I like the way it feels and now I want you to take my virginity." Even as she says this, she's grinding up against me making my cock even harder in sweet anticipation.

"Then why are you even going through with this whole nun thing?" I wonder even as I grind back against her mound.

Delilah sighs and hesitates. Then she shakes her head. "It's... complicated. Now, take me, quickly, before I change my mind... please?" she asks, me, her bright blue eyes looking up at me, begging me to deflower her. Before I have a sudden bout of sanity cross my mind about this, I reach down between us, position my cock towards her waiting pussy, spread her open and thrust into her. "OOOOOHhhhhhhh!" she closes her eyes, arches her body, and cries out in ecstasy as I suddenly spear her. Now the sinning for us is complete as I'm now officially the only man who'd ever be with her in the biblical sense. Taking her for the first time was surprisingly easy, I noted, and I found out later that whatever bit of hymen she'd had prior to tonight she'd lost over time due to stretching, exercises, and her 'playing' which did involve toys.

"You okay?" I gasp as I revel in the tightness of her virgin pussy. "I didn't hurt you, did I?"

Delilah shakes her head. "I'm fine..." she gasps as well as her hands are now out to her sides, fists clenching the bedsheets. "It feels so good... it's wonderful..." she moans. "Please don't stop... I want to feel it all."

I smile down at her, even though her eyes are still close, and lean into her. I start pumping my hips into her, going very slowly at first so she can get used to it. I angle my body so that I'm just slightly off center of her while I fuck her. This way I'm able to rest my weight onto one arm as I kiss the side of her face and gently suck on the side of her neck in such a way to not leave a hickey or anything. My free hand comes up to cup her soft, supple breast where I gently knead it in my grasp and brush her hard nipple with my thumb. Delilah moans in response, now relaxing enough to put her hands on me and to even twist her head to meet my hungry lips to kiss. I drive my cock into her in slow, deliberate thrusts. I want to take my time with her and show her a good time. She's moving her body with mine, moaning in pleasure the entire time. I can tell that she's enjoying it as every so often her pussy clenches around my cock but she's nowhere near climax. Another approach is now needed.

She opens her eyes and gives me a questioning mew when I suddenly stop and pull out of her. I can tell she's about to ask me why and I cut her off before she can by smiling at her and kissing her gently on the lips. "Relax and trust me. Roll to your side," I tell her. Delilah gives me a skeptical look, but she does it nonetheless. I shuffle over to spoon with her, pausing only to pull her bottom close to my lap so that I can slide back into her pussy. "Oh!" she gasps in surprise at this new position. Then she moans deeply as my cock drives home and her body re-accommodates it. "OOoohhhhhh..."

"Just close your eyes and relax," I whisper into her ear, wrapping my arms around her. My left arm, under her body, comes around to cup her left breast while my right hand slides down her thigh, over her golden pubic hair covering her mound, and down to feel up her pussy that's full again with my cock. I spread her labia open just a bit to get at her clit where I proceed to rub it in a left-right motion as I slowly thrust in and out of her. Her body seems to melt against mine as she lets out another a low groan of passion. I gently nibble and suck on the back of her neck, experimenting until I find where she's the most sensitive at. Once I hear her let out a breathless sigh of ecstasy and chant "more," I attack that spot while still methodically fucking her, fingering her, and fondling her.

When the orgasm finally hits her, it's a surprise to us both. One moment she's grinding back against me and then the next she cries out really loudly as her body jerks and spasms so hard that I think for a moment that she's having a seizure. One hand of hers jerks back to clench my left thigh while the other one comes up to clamp around my wrist that's over her chest. "AHHHHHAHHHHAHHHH!" she squeaks as she thrashes around next to me with me holding her close. I feel her pussy now fluttering around my cock and by this point I'd been fucking her for so long that I can't hold it back anymore. I let out a deep grunt as my cock erupts inside of her, flooding her unprotected womb with my semen. I got to admit; I really enjoyed that orgasm as just the thought of my seed possibly seeking out her egg to possibly fertilize was a huge turn on for me and I kept my cock lodged up inside of her long after it'd stopped twitching.

Delilah's body was still shaking next to mine and it took me a minute to realize that she was crying. "Hey," I say softly, now sliding my arms around her to just hold her even with my cock still inside of her pussy. "Are you okay?"

"I'm fine, Gerry, thank you," she said. She turns her head to give me a smile through the tears. "It was just so wonderful and beautiful. I never thought it could feel like this before." She then cranes her neck to give me a peck on the lips, reaching back with her hand to run it through my hair. "Thank you, so much, for this."

"Anytime," I say, smiling back at her, glad that she enjoyed it.

She lets out a long breath as she wipes her hands over her face and then runs them back through her hair. "I'm going to have some serious confessing to do after this."

I let out a snicker. "You and me both. I wonder what the penalty in hell is for deflowering a nun?"