A/N: Female self-insert Yancy smut. Mature readers only. Enjoy!
Such a Tease
Relationships in prison were different. There were a lot more rules restricting couples here than in the outside world. In fact, relationships weren't technically allowed. But there were still plenty of them at Happy Trails Penitentiary.
You were in one of them with a greaser type named Yancy. He was universally loved by everyone there. It seemed as if most people either wanted to be him or be with him, and you were lucky enough to be with him.
Everyone knew this, even the guards. But they didn't normally actually do anything about relationships unless they caught you. They couldn't be mad at you for spending time with someone or being in their cell. You weren't meant to touch other inmates, but they allowed hugs and arms around each other as long as things were kept PG. It was kissing and sex that they would come down on you for, so couples had to sneak around to do that. You and Yancy had become pretty good at being sneaky by now. You had your meeting places and you knew which guards might let certain things slide. And because you had practically mastered the system, you were easily able to keep your relationship interesting.
Sometimes the two of you would slip each other romantic notes. Sometimes you'd borrow cell phones other inmates had snuck in and send each other pictures or texts. Sometimes you'd surprise each other with gifts you had saved up for in commissary, and you met up regularly to have alone time. But when you woke up from an inspiring dream on a typical Friday, you knew it was time to try out something new.
You normally obeyed the uniform rules. They were pretty lax anyways, and the warden and guards didn't mind people personalizing their looks. But the one thing they asked was for modesty. Meaning you shouldn't show too much off. But today felt like a good day to bend that rule.
Happy Trails gave inmates several clothing options: the striped shirt and pants set, grey sweatpants, plain t shirts and shorts, and jumpsuits. Today felt like a good jumpsuit day, but you purposefully left most of the buttons undone to show off more than a little cleavage. You also used a heatless method to get some waves in your hair and you put on some DIY prison makeup that your friends had shown you how to make. You felt good, and you knew you looked good, too. Your fellow female inmates were quick to compliment you and ask what the occasion was. You just told them you were planning on having some fun with your boyfriend.
At breakfast, you found Yancy sitting at his usual able with his male inmate friends. You always said hello to him in the morning and would chat with him for a bit after you ate with your friend group. So once you were done eating, you made your way over.
"Morning, Yancy," you smiled, leaning over the table and crossing your arms under your chest, purposefully boosting up your cleavage to show off for him.
"Morning," he said, barely glancing at your face before his eyes drifted down. He got a good look in before he returned your gaze. "Youse look great today, y/n."
"Well, thank you! I just felt like putting a little extra effort in," you replied with a smile.
"Youse always look great no matter how much effort youse put in. But I'm definitely not complaining," he said, enjoying the view some more.
An inmate across the table from Yancy dropped his fork on the floor with a clatter, but before he could grab it you saw the opportunity in front of you to tease your boyfriend even more.
"Oh, I'll get that for you," you decided, bending over right in front of Yancy to grab it.
"Thanks, y/n. I think Yancy thanks you, too," he chuckled. When you stood up and turned back around, you noticed Yancy shifting in his seat with pink cheeks, most likely embarrassed from his arousal in a room full of so many people.
"Well, I better get back to my table. I'll see you around, babe."
"Wait just a second!" Yancy said, grabbing your wrist and pulling you back before you could walk away.
"Yes?"
"Meet me in the back during work. You know our place," he told you. You gave him a satisfied nod and headed back to your friends, laughing with them as you watched Yancy's friends joke with him and try to convince him to get up from the table. By the time breakfast was over and he did finally stand, he was no longer fully erect as you suspected he had been. But you thought you noticed a slight bulge as he headed back towards his cell.
There was another hour before work started to give inmates a chance to shower and whatnot if they hadn't already, but then it was time to head to your shift for the day. You and Yancy both worked in the laundry room, washing, drying, and organizing inmate clothing and sheets. While there were guards posted during work hours, inmates always found ways to sneak away and get away with all kinds of things, whether it be drugs, drinking, stealing, or sex. You and Yancy were no different, and one of your favorite meeting places was in the storage area of the laundry room, which was separated from the main part with the washers and dryers.
At your shift, you began by actually working and acting normally, so guards wouldn't suspect anything. But you watched for a chance for a guard to be distracted, and when you noticed two guards chatting with each other and looking the other way, you looked over at Yancy. He nodded, and began to head towards storage. You waited a minute or two so as not to cause suspicion, and then followed.
"So, what made you want to meet here this morning?" You questioned him, curling your hair around a finger innocently.
"As if you don't know. Youse have been such a little tease," Yancy replied, causing you to back into the walls to get you trapped. His hands went right to the buttons on your jumpsuit, and he undid the couple that you had actually buttoned that morning.
"Don't pretend you haven't loved every second of it," you grinned.
"Oh, I absolutely have. Although I would have preferred not to have to hide a boner at breakfast," he said.
"Sorry," you giggled.
"I forgive youse," he replied. "Now take this off so I can finally fuck you."
Yancy was tugging at your undone jumpsuit, and you let him pull it off of you, stepping out of it so he could toss it to the side. You grabbed the hem of his white t shirt and pulled it up over his head, throwing it on top of your clothes. The next thing you knew you had your tongues down each other's throats, your hands desperately grabbing at each other like you had been kept from each other for years. He unclasped your bra and ripped it off, taking your breasts in his hands and teasing your nipples. You ran your hands down his body, tracing his abs and v-lines before pulling his pants down and reaching down his underwear to stroke his hard dick.
"I want these panties off and I want youse on top of me right now," Yancy growled.
You quickly stripped out of your underwear as did he. He took a seat on some sturdy looking boxes and you climbed on top of him. The second you got into his lap he pulled you down onto his dick, thrusting up into your soaking wet pussy.
"Fuck yes. Finally," Yancy groaned. You held onto his shoulders for support and moved your hips just the way he liked it, trying to keep quiet as he ruined your insides just the way you liked it.
The boxes quickly began to give way underneath you, and you heard them tear.
"Yancy..." you mumbled, your face buried in his neck in order to muffle yourself.
"Table," he said shortly, clearly not in the mood to waste any time.
You both headed towards the middle of storage, where there was a table with extra clothes for new inmates. You kept a pile to use as a pillow and pushed the rest out of the way before climbing on top and laying down on your back.
Yancy took his place on top and you wrapped your arms around his neck and your legs around his hips. He went back to work on you, harder and faster this time. The table shook violently as you both held back your moans, in pure ecstasy while other inmates were working a few storage racks away.
It wasn't long before you felt a climax begin to build as Yancy slammed into your g spot, making you weak. You could tell he wasn't going to last much longer either, which was for the best. If the two of you disappeared for too long, the guards might come looking.
"Babe, I'm gonna cum," you warned, your legs shaking as the euphoria intensified.
He put a hand over your mouth to muffle your moans as you came, giving in to your body's reaction to being fucked just the right way. Your walls tightening around him combined with the sounds you were making seemed to be exactly what he needed to finish, too. He pulled out and came on your chest, his eyes shut tightly and his mouth open in pleasure. It was clear by how heavy his breathing was and by how wobbly your legs were that this had been one hell of a session.
"Good thing we're in the laundry room," Yancy huffed, handing you some of the clean clothes from the table so you could clean yourself up.
"Yeah. We should probably get dressed and head back," you realized, pulling your bra and underwear back on. Yancy began to dress himself again too, but you stopped him midway to sneak a kiss in.
"That was amazing," you told him. "I'm so glad I decided to be mean and tease you," you smiled.
"If you keep it up maybe we can do this again after dinner tonight," he winked.
You both finished getting dressed and went back to work, and after an outfit change into shorts that you had rolled up a bit too much and a shirt without a bra, you both had another amazing time later that evening. So much for relationships not being allowed in prison.