#t bag

Pairing: Theodore Bagwell X reader

Warnings: DDDNE (seriously!!!), Tbag himself is a warning, age-gap (reader is legal I imagine her to be like 20-21), dumbification, faux!Cest, kinda dbf themes, degradation, could be considered grooming, he's kinda mean, ddlg-esque, Reader calls Tbag ‘Uncle Teddy,’ but they aren’t related.

Summary: Good ole ‘Uncle’ Teddy has just broken out of Fox River, and he knows you’re just so eagerly waiting for him. He tries to be good, but once he gets a taste nothing can stop him.

Sometimes you wonder if God exists…and when you’re not you’re asking him why he’s so cruel.

For the longest time you had a great life - you were never rich, never had much but it didn’t matter, your father loved you unconditionally. He was the light of your life, always spoiling you, encouraging you with sweet words even after your mother left.

So- now that he’s passed it’s ironic that the only person you still have left is none other than Theodore Bagwell. Theodore (or ‘Uncle Teddy’ as you learned to call him) was a close friend of your father’s. He didn’t come around much but when he did he stayed a while and he was always sweet to you- always made you feel special. However, even though he was kind you never knew much about the man, just that he cared for you.

He’d been locked up when you were 18, a few years ago now. When you’d heard about his crimes it made you sick to your stomach. Not only because of his vile actions…you felt sick because a part of you still wanted him in your life. A part of you felt like he was the only piece of your father that was left.

⚠️DISCLAIMER - IN MY HEAD AND IN MY FIXS HE IS NOT A RAPIST OR PEDO AND THIS IS BECAUSE I WOULD DO HORRIBLY SLUTTY THINGS TO HIM IF GIVEN THE CHANCE AND I NEED TO GET MY HORNINESS OUT SOMEHOW AND THERE IS NO CONTENT FOR THIS MAN. LADIES AND GENTLEMEN I AM THIRSTY. THIS MAN MAKES ME FERAL.⚠️

Summary: You started sleeping in T-Bag's room because you needed him for comfort. You continued because you needed him for... something else.

Warnings: SMUT. Mentions of violence, PTSD.

...

The first time you slept in T-Bag's room was because you needed him. You were hard to read, you learned to be in prison. You maintained a level of secrecy designed to ensure your weaknesses could not be found. You watched more than you did, listened more than you spoke, and generally tried to make sure that you had a good read on those around you even if they knew nothing of you. It was how you operated.

When Gretchen took you... it was brutality like you had never seen. You tried to avoid looking at the ugly scars on your back, you slept with a gun beside you and a knife under your pillow. You hated the feeling of anything touching your wrists after being shackled for so long. Death would have been a dream locked up under her watch.

When you and LJ were handed over you isolated for days, only opening the door to your room in the compound when Michael or Sarah left food outside for you. When you and T-Bag broke into a charity event to steal the SCYLA card you thought for sure Gretchen had found you once again and you grabbed him and yanked him into a storage closet with you. In the cramped dark closet with a confused T-Bag you began to panic, gripping his arms until you're knuckles turned white. It took him a moment to understand what was happening. Slowly he wrapped his arms around you, running his hand through your hair and pressing your face into his neck. He hushed you, mumbling in your ear that it wasn't Gretchen, she was dead.

"Teddy's got you, sweetheart. Nobody is ever going to hurt you again, I'm here now."

It was that night that you knocked on T-Bag's door for the first time. You had laid in your bed tossing and turning for hours. If it was only an inability to sleep you would have just laid in bed, but it was also a suffocating feeling of paranoia. You felt like she was there with you.

You werent sure why it was him you needed, you suspected it was because he was the only one who had seen you panic like that. You had never been held by Sarah or Sucre or Alex or anyone else. You had never spoke more than what was necessary to any of them. You hadnt to T-Bag either, but you enjoyed his company. He made you crack a smile with his stupid one liners and witty comebacks.

You were half expecting T-Bag to be asleep. You jumped a bit when he opened the door, hair tousled and eyes half closed. He was wearing a tank top and boxers and took a moment to realize it was you standing outside his door.

"What a surprise. What can I do for you, Señorita?"

You weren't quite sure what to say. "I don't want to be alone," You admitted, chewing on your lip.

To your surprise, T-Bag didn't wink or make a suggestive comment, he simply stepped aside, motioning for you to enter.

You walked into his room, perching on the side of his bed. It was cold in his room, your legs and arms becoming littered with gooseflesh under your shorts and t shirt.

T-Bag laid down beside you, holding open the blanket for you to lay down with him. "You want to talk? Or just cuddle with Teddy?"

The childish language and third person referencing should have irritated you, but honestly, it was comforting. He seemed genuine, in his own T-Bag kind of way. So, you laid down beside him, facing away. You pulled one arm around you and laid your head over his other arm, just above his prosthetic. "Well now, making yourself comfortable, huh?"

You smiled, glad he couldn't see it. "What, is your arm gonna go numb?"

T-Bag chuckled, nuzzling his face into your neck. You hoped he didn't notice you shudder.

"I s'pose not."

You slept a bit that night, feeling warm and protected. You disappeared before he woke up.

...

The second time you slept in his bed was a few nights later. You went to him earlier that night, this time he greeted you with a smile and guided you in with his arm around you.

You did the same thing the next night, and the next, and a few more times. The difference was how late you stayed into the morning.

He never tried anything with you, never even initiated. He did wake up with a stiff cock in his shorts a few times, but most men did. He usually just rolled over. It was odd, seeing T-Bag be so careful with you. He'd always made comments before, and still did during the day - but not at night, not when you came to him in need.

...

This night was different. You needed Teddy to sleep, now. He referred to himself as Teddy Bear teasingly, but he was right. You needed his comfort, his warmth. And now, you needed something else.

You were completely naked under a large t shirt tonight. Your heart beat fast as you walked down the hallway. Your hair was down, your skin smooth from being freshly shaved and lotioned.

You knocked on the door, as always, and were greeted by a smiling Teddy, as always.

"I was beginning to worry you weren't coming, Sugar. I was getting a little tired."

You said nothing as you climbed in bed with him and waited to feel his warmth behind you. He settled in, onw arm under your head, one tucked around your waist, his face buried in your neck. He breathed in deeply, "You smell sweet," he mumbled. "It's nice."

"Thanks," You let your hand drop down to Teddy's, running your fingers over his wrist, "mind if I turn off the light?"

"'Course not."

You planned this, of course. Leaned up you made sure to stretch extra far, your shirt riding up under Teddy's hand and leaving it laying on your bare hip. You felt Teddy's fingers stiffen, realizing your shorts weren't under your shirt like they always were, nor were your underwear.

His voice lowered in your ear, hand locked onto your hip. "I think you forgot something, Miss Y/N."

"Did I forget anything else?"

Teddy didn't move at first, almost waiting for you to take it back. Slowly, his fingertips moved up your side, under your shirt, and up to your bare breasts. He sucked in a slow, deep breath as his hand finally came to softly squeeze your breast. He fondled your breast a few more times before moving to your nipple. He growled into your neck when you shifted to an angle that allowed him to touch your other breast.

"Y/N," his tone was strained, like it was physically difficult for him to get the words out, "If you're backing out you gotta do it now, darlin'."

You slowly moved his hand from under your shirt and sat up beside him. You watched him close his eyes, taking several controlled breaths. He laid on his back, rubbing his face with his hands. If you were a cruel woman, you'd let him suffer. Instead, you smiled softly to yourself and lifted your shirt over your head, dropping over Teddy's face.

In the time it took him to fumble with the shirt you pulled out the stiff cock peeking from the hole in his boxers and got on all fours, making a show of your ass and arching your back.

Teddy let out a low groan when he saw you, on all fours beside him, eyes sparkling with a naughty smirk as you licked the red tip of his cock. His eyes were frighteningly dark now, that tongue of his peaking out on his lip and his hand fisted in the blanket.

You took a few inches of him into your mouth, using your hand to stroke what you weren't sure you could fit. Teddy let his head fall back on his pillow, low groans and curses falling from his lips as you sucked. He looked up every once in a while, he needed to take in the view he had of your breasts just grazing the mattress and your ass in the air.

It took a lot of willpower, but after a few moments Teddy put two fingers under your chin and gently pushed your head up and off of his cock. He sat up, pulled off his tank top, lifted his hips, and tossed off his shorts. Then he laid back on the bed, shimmying down into the mattress, and grinned at you. His tongue darted out onto his lip - that tongue thing drove you crazy.

"C'mon over, darlin'. Sit down, give Teddy a taste."

You felt a shiver run down your body at the thought. You felt a bit insecure, but there was no way you'd be turning down that offer. You swung a leg over him and faced the wall, a knee on either side of his head. His eyes glinted up at you as he grabbed your hips and tugged you down onto his mouth.

You let your head fall back as he started on you. He kept his prosthetic arm locked onto your waist and he lowered his other hand behind you, playing with himself as he ate. His tongue was everything you'd dreamed it would be. It went deeply into your cunt a few times, then came back and circled around your clit. He nibbled and sucked and licked as you rocked a bit on his face, desperate for more of whatever the hell he was doing to you. One of your hands was pressed against the wall, the other scratching lightly at his scalp. He moaned against you, still rubbing himself behind you.

It was a slow building orgasm, the heat in your lower belly growing and your body beginning to tingle. You were trying your best to keep the volume down, the last thing you needed was everyone making fun of you two come morning, but the closer you got to cumming the harder silence became. You felt your thighs beginning to shake around his head, and you tried to raise up and catch a break, afraid you would cry out. Teddy's arm roughly yanked you back down, locking around your hip. He released his cock, bringing his hand up to smack your ass, scolding you for pulling away. Then, he reached up and pushed two fingers into you, still sucking on your clit. Your whole body began to quake as he gently massaged the inside of your cunt. He chuckled as you froze, body completely rigid as you fell over the edge. You covered your own mouth with your hand, letting out a choked cry and continuing to rock on his face. He withdrew his fingers and became more gentle with his licking, easing you through your orgasm until you were trembling over him. On shaking legs you rose up off of him, shuddering as he pressed one more kiss to your clit. You plopped down beside him, cheeks flushed and hair tousled. He sat up, pushing your hair behind your ear and leaning in, almost kissing you.

"You taste as good as you look, pretty girl." He leaned in a little closer, brushing his lips against yours. You were too impatient to wait, pressing your lips against his mouth, still wet from you. He reached up and cradled the back of your head in his hand, rubbing circles in the spot behind your ear. You held his face in your hands, heart racing. You kissed for a few moments, soft moans leaving your mouth into his. He began speaking between kisses, unable to keep the smile from his face. "You know how hard it was keeping my hands to myself, Miss Y/N?"

He settled between your legs, the tip of his dick brushing up against your inner thigh. "Sleeping next to you every night? That ass up against me? I swear I could hear that pretty pussy calling my name."

He laid against you, propped up on his elbows, still kissing you as he spoke, "This ain't gonna be the last time, darlin'. I'm gonna need to taste you again, and I'm gonna need to feel you again."

You reached down between you, rubbing him against your wet pussy.

"That's my good girl," he growled, pushing himself into you slowly. "I told you your Teddy Bear was gonna take of you."

You let out a whine. You hadnt noticed the slight curve in Teddy's dick, but you did now. It was rubbing against that delicious spot that his fingers had found earlier, sending shudders and heat through your body every time he hit it. Teddy fucked you in slow, deep, controlled thrusts. He nuzzled his head against your neck, sucking on your skin and mumbling dirty things. Your nails dug into his back and your legs locked around his waist as you tried to muffle your cries.

"Aw now baby don't go holding it in. Let everybody out there hear Teddy make you feel good. Make sure they know you're mine now. All mine, Miss Y/N. That pussy is too good to be anyone else's. You belong with me."

His works were a mixture of sexy and sweet. You felt like he might really mean them. You hoped he meant them.

You let out a pathetic whine as he pulled out of you and he chuckled, shaking loose from your hold and sitting back on his knees. He motioned for you to sit up as well, and then for you to turn around. You sat on your knees, once again facing the wall. Teddy settled behind you, kissing your neck and holding you around the waist with his prosthetic arm. His other hand brought his cock to your pussy from behind, and you arched your back, laying your head on his shoulder. Teddy chuckled, "What a good fucking girl sticking that big ass out for her Teddy Bear."

He pushed in much faster this time now that you had grown accustomed to his size. You cried out as he began thrusting into you much harder and faster, his hand coming up to grip around your throat. He applied enough pressure to give you little pinpricks in your vision, but not enough to hurt you. Teddy would never hurt you.

"You take this big dick so good," he grunted in your ear, his voiced sounding strained now. "Is all this for me? Hm? Who's are you?"

"Yours, yours Teddy," You choked out, inhibited by both his hand and his dick.

"That's my pretty girl. All for me, all Teddy's."

He released your neck and waist and you fell forward on all fours, once again arching your back for him. He hit a new spot now, and you knew you wouldn't last long.

"Fuck, darlin'. Ain't no view of you I don't like." Teddy smacked your ass, still thrusting into you almost too deep to handle. "In fact you look so damn good right now I don't think I'm gonna be able to handle it much longer. Where you want me?"

"Inside," You moaned. You'd get a Plan B tomorrow...

"Dirty, dirty girl," he groaned. "Just look at that pretty pussy grippin' Teddy's big dick. You're gonna take it all, pretty girl. I'm gonna fill you up."

Teddy's filthy mouth was sending your mind spinning, you felt like you couldn’t breathe. You arched into him just a little more until he hit the spot you needed, and then it hit you like a train. You couldn't keep this cry in, your body once again trembling. You felt your pussy pulse around his cock and your slick ran down your inner thighs. Teddy gave a strangled groan behind you, not expecting your pussy to grip him the way it did. You felt his dick stiffen and then twitch inside of you, hot cum filling you. He continued thrusting into you, his hand rubbing your ass. His moans and groans sent shivers through you - you loved a man that made a little noise. When he finally slowly pulled out he sat back, spreading your pussy open with his hand.

"Push out for me, darlin'."

You did, blushing when you felt a river of his cum gush out of you and down your thighs. Teddy let out a long moan watching it, and then delivered your ass one more good smack. "Too fuckn' good, pretty girl."

After a moment you fell onto your side, body still tingling and pussy swollen. Teddy got off the bed, leaning down and pressing another slow kiss to your lips before taking your hands and pulling you off the bed. You whined when you stood. You were exhausted now.

"You hush now," he scolded playfully. "C'mon."

You did not follow him to the door, raising an eyebrow when he turned around to look at you.

"Well we gotta shower off now, darlin'. We made a mess of ourselves."

"We're naked, Teddy."

He scoffed, opening the door. "Nobody's awake right now, pretty girl. And if they are, they're fuckin' too."

He walked out, leaving the door open behind him. You hesitated for a moment, but you were all sweaty and sticky... and you didn't want to pass up the opportunity to see Teddy all wet and dripping...

You followed behind him, trying to be quiet and hoping nobody saw you, shiny with sweat, red ass from Teddy's smacks, flushed face and messy hair and wet tracks leading from your pussy down you legs. You sprinted down the hallway and to the bathroom where Teddy had already turned on the shower and stepped in. You locked the door behind you and joined him.

Teddy was really a very sexy man. Strong, but not too muscular. His face was so sharp and dark and his eyes just seemed to radiate power. He had a little bit of chest hair, and now that you were looking, his cock was pretty impressive even soft.

He was already covered in soap, so he handed off the bottle and wash cloth to you. You flushed a bit as you washed yourself, noticing Teddy leaned against the shower wall with his arms crossing and his bottom lip in his teeth as he watched the soap cascade down your body. After you had cleaned off, he held his arms out to you, wrapping you in his tight embrace. His prosthetic arm wrapped around your waist, pressing you tightly against him. You let your head rest against his chest and he leaned his on yours. With his hand he gently massaged the back of your neck.

"I'm going to take care of you, pretty girl. You're all mine. Nobody's ever going to hurt you again."

You pulled back a bit, gently touching his face and pulling him into another deep kiss. You smiled against his lips when you felt his cock twitch against you.

...

When you made it back to Teddy's bed, laying on his chest while he played with your hair, you replayed the whole night in your mind over and over. You would probably replay it forever.

"You know what, Miss Y/N?"

"What, Teddy?"

"I think you spend an awful lot of time walking back and forth between our rooms - and I spend an awful lot of time waiting for you. It'd save us both a lot of energy if you just stayed with me."

"You asking me to move in, Teddy?"

He smiled, gently taking your chin in his hand and pulling you in for a soft kiss. "I am. I can keep you safe and satisfied much easier if you're always by my side. You know I'll take good care of you. You're my pretty girl."

You bit your lip, feeling your cheeks flush once again. "And after this is all over?"

Teddy softly touched the side of your face, "I'm thinking a nice, warm beach. You and me. We can make a good life somewhere close to the ocean. Far away from all of this foolishness."

You pressed one more kiss against his lips, then laid your head back on his chest.

"I like that idea."