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The Loophole

"Good Christian girls don’t have sex. They find technicalities."

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The living room smelled like microwave popcorn and clashing body sprays. A group of girls lounged on the floor in oversized Baylor University T-shirts and pajama shorts, their Bibles now closed and set aside in favor of gummy worms and whatever rumors hadn’t already made the group chat.

This was Charity Hall, the biggest off-campus sorority house built on good, old-fashioned Christian values. A place where God-fearing parents could send their daughters and not have to worry about the sort of things that happened in other sorority houses at other schools.

With Bible study finished and everyone freshly fortified in virtue, it was time to unwind like every other college girl in America. Someone put on a Hillsong Worship playlist, but it faded beneath the chatter of post-study gossip.

Allison sat curled up on a beanbag chair, nervously twirling a strand of hair, and cleared her throat.

“Okay,” she said, louder than she meant to. “Can I ask you guys something that might be kind of… weird?”

Heads turned. A few eyebrows went up. Tori stretched across the couch like a swimsuit model for Jesus and propped herself up on one elbow.

“Uh-oh,” she said. “Let’s hear it Allison, what you got for us this time?”

Allison blushed. “I don’t know, it’s just… Trevor asked me something, and I didn’t know what he meant. I didn’t want to seem dumb, so I told him I’d think about it. But I don’t actually know what I’m supposed to be thinking about.”

“Wait,” one of the girls said. “Is this a sex thing?”

Allison covered her face with both hands. “I have no idea. I googled it, but nothing I found made sense, but he said it like I should already know.”

That got everyone’s attention. Pillows shifted. Heads turned. Someone paused the music, like a Christian band might be scandalized by what was coming.

Allison peeked out between her fingers. “He asked if I’d ever consider… the loophole?”

There was a beat of silence. Then the room exploded.

“Oh my God,” someone squealed.

“No way! You dog, Trevor!”

“The pastor’s son!” another girl gasped, clapping a hand over her mouth. “He’s got some freak in him!”

Tori just laughed and sat up, brushing a blonde curl off her shoulder. “Honey,” she said, her voice laced with mischief. “He wants to put it in your butt.”

Allison stared at her. “Wait. What?”

“That’s the loophole,” Tori said, clearly enjoying herself. “Anal. You can do it and technically”—she wiggled her fingers into air quotes—“you’re still a virgin.”

Allison paused, questioning. “That doesn’t count?”

“Nope,” Kerry chimed in. “That’s the whole point.”

“Your butt isn’t made for sex, so technically you’re still a virgin,” Carly said, popping a piece of popcorn into her mouth. “You stay pure where it matters to God.”

“It’s not even in the Bible,” Kerry added. “It says no butt stuff between guys, but it’s totally silent on girls and guys.”

Allison looked half-horrified, half-curious. “And you just… know all this?”

Tori leaned back against the couch, smug in that way only a youth group leader could be. “Sweetie,” she said, “you’d be amazed by what some of us will do to keep a purity ring on our finger.”

After some minutes, the room finally settled, though a few girls were still snorting into their sleeves. Someone passed around a bag of mini marshmallows like it was communion. But Allison sat with herself, taking it all in, and was still unsure. The laughter had faded, but the questions hadn’t. She couldn't fully wrap her head around it, not yet anyway.

“Girls,” Tori said, adopting the same tone she used during house meetings. “Looks like Ally’s genuinely conflicted, so can we, like, actually talk about this?”

“About butts?” someone snorted.

“Yes,” Tori replied, perfectly straight-faced. “About butts. For the sake of Christian sisterhood.”

There were groans and exaggerated sighs, but no one left. They were committed now. “Lord help us,” Kerry muttered from the far side of the room.

“So,” Tori said, scanning the room. “Show of hands. Who’s actually used the loophole?”

There was a pause. Then, slowly, hands began to rise. Two at first, then three, followed by a fourth.

Allison felt her stomach twist as she counted. Tori raised her hand last, wearing a self-satisfied little smile.

“Wait,” Allison said. “Seriously? You guys?”

“I mean…” Lauren said, bent over a compact mirror, wiping away mascara that gave her the face of a televangelist’s wife. “My mom said the Catholic loophole includes blowjobs too, so we’re, like, halfway holier.”

“Jared’s been hinting to me about it,” Carly added, shifting in her seat like the question had been on her mind too. “Like, a lot lately.”

“It’s not that bad,” someone else said. “You just have to relax, and use lube.”

Tori gave a solemn nod. “Oh, God bless lube.”

“I thought it would feel gross,” Lauren added. “But honestly? It’s kind of hot. Like, you’re doing something totally wrong, but you’re still a good girl.”

“That’s it exactly,” Tori said, raising a finger. “You’re obedient. But also, kind of a whore of Babylon.”

The girls broke into another round of laughter.

Allison hugged a pillow to her chest. “Okay, but… is it really ok, like in God’s eyes?”

“Your body’s a temple,” Tori said. “You save the front door for the guest of honor, but it’s fine if a few sneak in the back before he shows up.”

The room lost it. Marshmallows flew. Someone choked on a mouthful of Diet Coke.

Allison laughed along, but her face was hot. She hadn’t even kissed Trevor with tongue until six months ago, and assumed all of her friends were the same. Now it felt like she was the only girl with a boyfriend in the room who hadn’t been… invaded.

“Is this, like… normal?” she asked quietly.

Carly looked over and gave her a smile.

“It is with these harlots,” she giggled.

The group had thinned out. A couple of girls had drifted off to their rooms. Carly was half-asleep on the beanbag chair, with a Baylor bear tucked under her arm. Tori was painting her toenails by the glow of her phone screen, as Allison sat nearby, chewing on a gummy worm.

“So, like,” she said, “if someone were to… consider it… how would you even start?”

Tori didn’t look up. “You mean training your butthole?”

Allison squirmed and gave her a playful slap. “Can you not say it like that?”

Tori smiled. “Sorry. I mean prep. There’s steps.”

She started listing them, slow and matter-of-fact. Go slow. Use lube. Make sure you’re clean. Start with a finger, or maybe something else. Work up. Be patient. Breathe. Trust your body.

Allison nodded like she was cramming for a quiz. But when she stood to leave, the hesitation was still there.

“Don’t overthink it. You’ll be fine,” Tori glanced up. “It’s not like Trevor knows what he’s doing or has expectations.”

Upstairs, Allison had just turned off her lamp and pulled the sheet over her legs when she heard a knock at the door. She got up and opened it, half expecting it to be Carly looking for a charger. But it was Tori, makeup off, her hair twisted into a messy bun, and ready for bed.

“Hey,” she whispered. “Can I come in for a second?”

Allison stepped aside. “Yeah. Sure.”

Tori shut the door behind her and held out a small velvet pouch. “Okay. This might be weird, but I brought you something.”

She said it like she was offering gum or lip gloss.

Allison took the bag and peeked inside.

“Tori—oh my God. What is that?”

“It’s a butt plug,” Tori said, smiling. “It’s clean. I boiled it. I have, like, three others.”

Allison held the pouch like it might buzz or explode.

Tori sat on the edge of the bed, her voice was gentler now. “You don’t have to use it. But if you’re serious about trying it… this’ll help.”

Allison hesitated, then took it in her hand. It felt heavier than she expected.

“Do I just… put it in?”

Tori looked up at her. “I can walk you through it if you want.”

There was a pause. Allison nodded.

Tori patted the bed. “Lie on your side. I brought lube too. Deep breaths, like you’re trying to settle your nerves.”

She reached for the plug. “I’ll hold it. You guide.”

Allison turned on her side and lowered her sleep pants. She felt Tori’s hand graze the bare skin of her bottom. It was the first time anyone had touched her like that, and her whole body tensed.

“You’ve got a cute ass,” Tori said, like someone who’d helped girls like this before. “No wonder Trevor’s obsessed.”

There was no giggling now, just a tension that made everything seem too real.

“I need to pull your panties down a little, too. That okay?”

Allison gave a tight nod, not trusting herself to speak.

She felt the gentle tug of cotton sliding down, the fabric brushing her thighs. One leg lifted instinctively, her knee bending to give more room.

Tori sat beside her, one hand resting lightly on Allison’s hip, the other slick with lube and holding the plug. Her touch was calming and gentler than Allison had expected.

“You okay?” she asked.

Allison gave a small nod.

Tori helped her guide it in, slowly. “Think about Trevor. Pretend this is him.”

The room stayed quiet. The silence between them somehow wasn’t awkward. It was focused and oddly intimate. Allison’s hand started to drift between her legs, more by instinct than thought, but the moment she remembered she wasn’t alone, she yanked it back. Her face flushed, and didn’t dare check to see if Tori had noticed.

When the plug settled into place, Allison let out a shaky breath. “It feels… weird. But kind of nice.”

“That’s the point,” Tori said softly. "Learn to want that feeling."

Allison stared at the wall, still not able to look at her friend. “This is what Trevor’s thing is going to feel like?”

Tori scoffed. “Ally, you’re going to be taking it up the ass, you’ve got to start calling it his cock. Or at least his dick. Anything but his ‘thing.’”

They both laughed, breaking some of the tension.

Tori stood. “Don’t sleep with it in,” she said, brushing her palms on her shorts. “But when you wake up tomorrow, slide it back in. Leave it all day. Get used to having something in your ass.”

Allison blushed. “You really don’t have a filter, do you?”

Tori grinned as she reached for the doorknob. “What would be the fun of having a filter?”

Tori left without waiting for a response, and Allison was alone again. Still on her side, the plug nestled inside, her cheeks flushed, wondering how this had become normal.

She rolled onto her back. The room was quiet except for the hum of the AC vent. As she shifted, the plug moved deeper, snug in its new home. Her thighs tensed. She closed her eyes and pictured Trevor behind her, his hands gripping her hips, his breath against her neck. What if it wasn’t the plug inside her right now, but him? What would it feel like in the other place—the one she was still saving?

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Her hand moved down without much thought. Just a graze of fingers at first, then a slow rub through the soft cotton of her panties. She was wet, shamefully so. She drew a quiet breath through her nose, legs tightening as her fingers circled her clit. The pressure from the plug added something extra, making everything feel dirtier... and better.

She kept going. It felt wrong, but not wrong enough to stop. Her hips had a mind of their own now, chasing the movement of her fingers. Again she imagined Trevor behind her, his hands firm on her waist, cock pressing against her. Probably bigger than the plug. She hoped it would hurt, just a little bit. A small penance, just in case the loophole wasn’t something God was really willing to look the other way on.

Her fingers moved faster, with no rhythm to them, just following whatever felt good. She buried her face in the crook of her arm to keep quiet, not wanting the girls next door to hear her moans. A few more seconds, and her orgasm hit. Her thighs clamped together, her body trembled, and she came hard, the sound of it all muffled into her pillow.

She lay there without moving, just breathing hard, trying to catch her breath. One hand was still tucked inside her panties, the other gripping the sheets, her eyes locked on the ceiling because looking anywhere else felt wrong.

“I’m sorry, God,” she whispered. The words came out like a reflex, an automatic response like when she told a little white lie or cut someone off in traffic. Then she caught herself. Did I really just pray with soaked panties and a butt plug in my ass?

She covered her face and laughed into the dark, the absurdity too much to hold in.

The next day, Allison waited until after lunch to text Trevor. It took her an hour to write the message, and another fifteen minutes pacing her room with her thumb hovering over the send button.

Hey. I’ve been thinking about what you said.

About the loophole.

I’m ready.

Let’s do it.

She sent it before she could change her mind. A moment later, she followed up.

You can come over tonight.

The girls already know.

Trevor replied almost instantly.

Are you serious?

Like, actually serious?

Then the typing bubble.

I’ll be there.

Just tell me when.

Allison sat on the edge of her bed, hands in her lap. Her heart was beating faster, like it did when she went for a run. She’d just taken the plug out. She had it in all morning, just like Tori had told her to do. Now there was nothing filling her, but the thought of Trevor taking its place made her shiver.

By evening, the house felt different, a little restless.

Carly was making popcorn again. Lauren was painting her nails on the coffee table. Tori lounged on the couch in gym shorts and a hoodie like it was any other Tuesday, but everyone knew. Allison told them.

“So Trev’s coming over tonight.” That was all it took.

They squealed, teased, and called dibs on who got to listen at the door.

“You’re really gonna do it?” Carly whispered.

Allison nodded. “Honesty, it's all I've been able to think about."

Lauren smiled without looking up from her nails. “You’re, like, a real sorority girl now.”

Allison rolled her eyes, but didn’t argue. “Not yet, but soon.”

Just after seven, the doorbell rang.

Tori stuck her head into the hallway. “Your man’s here.”

Allison nodded and headed to her room, closing the door behind her.

She moved quickly, changing into a tight shirt and a loose skirt. Her makeup was already done, but she checked it anyway. She smoothed her hair one last time in the mirror.

The girls had coached her on how to do it the Christian way. No kissing. No eye contact. Keep your clothes on. Show only what needed to be seen, touch only what needed to be touched.

She climbed onto the bed and got on all fours, facing the window. Her skirt hiked up as she settled in. She slid her fingers under the waistband of her panties and pulled them down just enough to bare her ass, everything else still covered.

The lights were off. The window let in just enough glow from outside to prevent the room from being too dark. She considered music and candles, but decided against it.

A few minutes passed. Then the knock came, and her door opened.

“Allison?”

Trevor stepped inside. He stopped just past the doorway, his eyes adjusting to the low light. His mouth opened like he was about to say something, but nothing came out. His hair was a mess. It looked like he’d rushed the whole way over, because he had.

He just stood there, staring at her.

Allison didn’t turn around. She couldn’t. If she looked at him, she might see something in his face that would make her stop. And she didn’t want to stop. Not now.

“There’s a right way to do this,” she said. “God-approved. That’s what the girls told me.”

He stayed quiet for a moment, like he wasn’t sure if she was serious.

“No kissing,” she added. “And don’t get naked. Just pull your pants down.”

Another pause.

“You’re sure?” he asked.

She nodded, eyes fixed on the window in front of her.

“When you’re ready,” she said. “Get behind me. There’s lube at the foot of the bed.”

He fumbled with his jeans and got them halfway down before they caught around his shoes. He stepped out of one leg, gave up on the other, and climbed onto the bed behind her. The mattress dipped under his weight. One hand hovered near her hip, then rested there, a bit clumsy like he wasn’t sure where he was allowed to touch. With the other, he poured a ribbon of lube along his shaft and worked it in with careful strokes, making sure every inch was covered.

Allison dropped her head to the mattress and arched her back. She reached behind herself and gently pulled her cheeks apart, just enough to help him see where to go. Lauren said that would help.

When the tip of his cock pressed against her clenched hole, she flinched.

“Sorry,” he whispered.

“Go slow.”

He did. He eased in, breathing through his mouth like he was trying not to lose it already. She felt every bit of him. He went deeper, and the stretch was more intense than the plug. It burned, but in a good way, one that made her toes curl.

Once he was fully inside, they stayed there. Both of them were breathing hard. Neither of them was speaking.

Trevor started to move. Careful at first, his strokes were short and uneven. His hands were on her hips now, and he struggled to find some kind of rhythm.

Allison kept her head down, fists knotted in the sheets. It felt unreal, like she was watching it happen from across the room. But her body was paying attention. The pressure hit something in the pit of her gut, and with each slow thrust, it got harder to pretend this wasn’t exactly what she’d wanted.

“That’s it, Trevor,” she said, breathless. “Fuck my ass.”

Trevor Stopped. He'd never heard Allison say anything like this before, and just hearing her use those words nearly made him cum. He gripped her hips, buried deep, holding still because he knew even the slightest motion would end it.

“C’mon, baby,” she said. “Keep giving it to me.”

He couldn’t hold it. He wanted to, but couldn’t. He pulled out, thrust back in, three hard pumps, and that was it. He gasped and came with a full-body shudder, buried as deep as he could go. She felt the twitch, the sudden stillness, the quiet.

He didn’t say anything.

She didn’t move.

“Oh God,” she said. “Did you just… cum in my ass?”

There was a pause.

“I wasn’t supposed to?”

“I—I don’t know. I just didn’t think you would.”

“I mean, you said fuck my ass. I was already right there. I figured it was, like… implied?”

He sounded anxious now, like he wasn’t sure if he’d just ruined everything.

“Don’t look at me like this!”

“I’m not looking!” he cried. “My eyes are closed, I swear to God!”

She buried her face in the sheets. “Oh my God. I have cum in my ass and I’m yelling at you about it. Jesus is watching.”

“I’m sorry! I didn’t—should I—should I go?”

“Yes! Go!”

Trevor scrambled back, fumbling with his jeans like he was defusing a bomb. He kept his eyes squeezed shut, one hand groping ahead like a blind man feeling for walls.

He found the doorknob, turned it, stepped into the hallway, and froze.

Five girls stood outside, casually leaning against the banister like they’d been there all night.

“Well, that didn’t take long,” Tori said.

“Atta boy, tiger,” Carly added, tossing him a juice box.

Trevor opened his mouth, then shut it. There was nothing he could say. These girls would see him in church on Sunday, and every time one of them glanced his way, they’d know exactly where he'd been. What he’d done. To their friend. He was going to need a lot of prayer to fix this. Maybe a second baptism. He turned and bolted down the stairs before anyone else could speak.

Inside the room, Allison stayed where she was—on all fours, forehead to the sheets—trying to decide whether to pray, cry, or just pass out.

She ended up laughing. Giddy at first, but it grew into something a little unhinged. The kind of laugh you get when your body doesn’t know what else to do.

Eventually, she pushed herself upright with a groan. Her knees ached. Her thighs were trembling. She could feel something slick inside her, lube mixed with something she didn’t want to think about, being pulled lower by gravity. The need to get to the shower suddenly became a life priority. She waddled to the bathroom, cheeks clenched tight, and shut the door behind her.

The shower came on hot, reminding her of the hell she was likely headed for now. She didn’t adjust it. Just stepped under and pressed her face to the tile, letting the scalding spray wash away any trace of Trevor and what they’d just done.

When she stepped back into her room, towel wrapped tight around her, Tori was waiting for her, sitting on her bed, apparently not bothered by what had just happened there.

“How was it?” she asked with a beaming smile.

Allison let the towel drop and rummaged through a drawer for underwear. “I never, for even a second, thought about where the cum would go.”

Tori snorted. “Rookie mistake.”

Still damp, Allison tugged on a clean T-shirt and collapsed onto the mattress beside her.

“What did I just do?” she muttered into the pillow.

“You took it in the ass, and by the look on Trevor’s face, you did it well.”

“Oh God, Trevor. I need to talk to him. I panicked when he…” Her voice trailed off. “I don’t think he imagined his first time ending with getting kicked out.”

“Yeah, he seems like he’d be a cuddler.”

Allison sighed, part exhaustion, part disbelief. “I can’t believe I actually let him do that.”

“You didn’t let him,” Tori said, stretching out beside her. “You scheduled it and picked out an outfit.”

Allison groaned and pulled the pillow over her face. “You think the loophole is real? That I’m still a virgin and my salvation is intact?”

“I do,” Tori said. “But just in case, we’ve got another loophole—repent and God forgives.”

Allison let out a sigh. “So now what?”

Tori looked over. “Now? You brush your teeth. Drink some water. And tomorrow you go to class like it’s a regular Wednesday.”

Allison smiled, just barely. “Like a good Christian girl.”

“Exactly.”

“Do you think I should tell my mom?”

Tori laughed. “Are you crazy? The loophole works with an all-powerful God, not Evangelical parents!"

 

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Written by GreyMatter
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