Playing With The Devil

By DeadNights24

22.4K 406 50

Aidan forces his friend to let him tag along to a kink/BDSM party but quickly finds himself overwhelmed, deci... More

Warnings
Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 10
Chapter 11
Chapter 12
Chapter 13
Chapter 14
Chapter 15
Chapter 16
Chapter 17
Chapter 18
Chapter 19
Chapter 20
Chapter 21
Chapter 22
Chapter 23
Chapter 24
Chapter 25
Chapter 26
Chapter 27
Chapter 28
Chapter 29
Chapter 30
Chapter 31
Chapter 32
Chapter 33
Chapter 34
Chapter 35
Chapter 36
Chapter 37
Chapter 38
Chapter 39
Chapter 40
Chapter 41
Chapter 42
Chapter 43
Chapter 44
Chapter 45
Chapter 46
Chapter 47
Chapter 48
Chapter 49
Chapter 50
Chapter 51
Chapter 52
Chapter 53
Chapter 54
Chapter 55
Chapter 56
Chapter 57
Chapter 58
Chapter 59
Chapter 60
Chapter 61
Chapter 62
Epilogue
Completed - Technically
NEW STORIES?!

Chapter 9

441 8 0
By DeadNights24

A few hours had passed by. Aidan had plenty more questions for us to answer, mostly for me to answer since Irene wanted to focus on the television. It was nearing dinner time now and I'd ordered us some food at least. I was sitting on one of the lounge chairs in front of the television. Irene had put on a movie she'd been wanting to see for some time now, while Aidan straddled my lap and quietly asked me more questions.

I had just explained to him what was available in terms of aftercare. We always had a fully stocked fridge and cupboard, as well as an array of stuffed toys and comfort items to use. His hands had been rubbing over my chest while we talked. It was rather soothing to sit back and watch someone dote over me like this. Seeing his comfort and gentleness, it was relaxing.

My own hands rested on the back of his thighs, massaging the muscles. We'd also discussed his comfort in clothes, as lingerie and sexually suggestive outfits were the clothes I normally laid out for Irene, and I wasn't about to put anything out that caused him any distress. He'd been interested in wearing some feminine clothes, so I helped him pick out a miniskirt and a sort of crop top hoodie that he was currently wearing. But that was all he'd been allowed to wear. No underwear, no socks. Nothing else. I had easy access to any part of him I wanted.

"There is something I need to actually ask you, Aidan," I said.

Irene leaned over and shushed me.

I lowered my voice, "There is a part of CNC that I'm happy to do with you early on, it's about when you sleep."

"What do you mean?" he asked. His head tilted to the side in a mix of confusion and curiosity.

"Well, a person sleeping can't give consent, so you typically have to ask for it beforehand. I wanted to know if it would be okay to wake you up with sex or to do certain acts while you were asleep? You can take back that consent at any time and especially during the act if you find yourself uncomfortable. I'll ask the night before regardless, but I wanted to see where you felt with it now."

I watched the cogs roll through his mind as he considered my words. I should have said that it wouldn't be the end of the world if he said no. I wanted to make this a no-pressure environment.

"Sure," he answered eventually. "I trust you."

"Thank you," I said as I slid one of my hands up his body.

I moved it all the way up, teasingly lingering on certain areas to see his reaction. He shuddered at the touch. I felt him press down his crotch into mine and begin to roll his hips. I grunted as my cock started to harden under the tight pants. I placed my hand over his throat and squeezed gently, pulling him close so I could whisper in his ear.

"Careful now, sweetheart," I moaned. "Daddy's going to want you so badly."

"What if I want to ride Daddy's cock?" he whined quietly.

I considered the idea. Having Aidan ride my cock meant he would have to stare at me from this position. He could go at his own pace and build himself up. I was more worried if he slipped or dropped down too far. I didn't have any lube in this room so if he took me all in while he was still tensing up, it was going to hurt. God, I did want it though. His hands had slid down to my belt buckle and were pulling it off slowly. I released my hold on his neck and leaned back into the chair.

"Please," he begged. I felt the button and zip loosening. His hands were so close to my cock, but he hesitated at where he was, waiting for me to consent. "I want to, Daddy."

"Hm," I groaned. "If you take your time, then yes, baby. Be careful."

I lifted my hips so that he could lower my jeans and underwear just enough to let out my cock. I watched him raise the skirt so he could look down at it. His eyes slowly drew up to mine and I smirked. Aidan was seeing it for the first time, and I was... gifted? I guess you could say that. It always took people a bit of getting used to.

"Right," I said, a little too cocky. "You hadn't actually seen it before."

"I... I uh..." he stuttered. "Th-... That's um... I knew you were big, but I can't... put all that... in..."

"Just be gentle with yourself and you don't have to take me all yet. Trust me, people take their time," I reassured him. I was used to it. "Daddy will take care of you."

He lifted himself up and lined up with the tip of my cock, holding me gently in place. He lowered himself onto it and moved slowly, allowing himself to get more aroused. I moaned softly, biting my lip to hold back. Irene was still paying attention to the television screen, so I had him all to myself. As he became wetter, he lowered himself further. His hands held onto my t-shirt tightly. I was resting my own hands on his hips, making sure he didn't go too far down.

"I have you, Little One," I whispered. "Take your time, there's a good boy."

As he reached the halfway mark where we'd been before, he started lifting and falling gently. I groaned softly as my length moved inside him. I kept my eyes fixed on his face. His eyes were moving over my body, refusing to go up to my face. His shyness was adorable. He'd just spoken about wanting to ride my dick, begged even, and now he was embarrassed. What a poor baby. I put my hand up and lifted his chin, making him look at me. He tried to avert his eyes and I tutted.

"Eyes on me," I commanded. "And lift that skirt, I want to see me inside you."

He forced himself to look at me, his hands going to the skirt and lifting it up. His lips were parted, and moans slipped out continuously. The light blush on his cheeks grew darker as he made himself keep eye contact. I lightly thrust upwards to match his speed, my eyes glancing down every so often to watch. His moans became more audible now. My eyes went over to Irene for a moment. She was turning up the television, but she kept glancing over to watch every so often. Probably also a little worried.

My hand fell from his chin, and I moved it down, rubbing over his clit. He sunk lower onto my cock and whimpered. His grip on the skirt tightened, and his knuckles went white. He'd stopped moving to steady himself, getting used to more of me. I relaxed into the chair, though I really wanted to thrust and keep that stimulation going.

"Slowly," I grunted. Don't move, Gabriel, don't scare him. "Take it slow."

His eyelids fluttered closed as he began to move again. I pressed onto his clit more, massaging deeply. He moved faster, opening his eyes to look at me eventually. What a good boy, making sure he looks at Daddy. I felt his walls tighten around my length and I grinned. His knees buckled as he came over my cock. I watched him closely, slowing down my movements on his clit.

"Gentle now, we don't want..."

Before I could finish my sentence, his legs wobbled, giving way under him and he slipped down. A hand flew up to his mouth, his eyes going wide. A muffled scream came through his hand and out of the corner of my eye, Irene jumped up from her seat. Tears formed in his eyes and my own went wide with shock. Gripping his waist gently, I attempted to lift him, only failing miserably.

"Help him," I said to Irene.

My hands kept to his hips, trying to lift him again but he refused to move, his body feeling heavier. Irene walked up behind him and placed her hands on his waist. Our attempts to lift him were made impossible by how stiff he was.

"Come on," she whispered. "It's okay."

"It hurts," he whimpered.

Tears had begun to stream down his face. He still wasn't allowing us to lift him up. He sat there, his walls tightened around my length, flexing and twitching. His legs were shaking uncontrollably. Fuck, please.

"Let us lift you up, we can get something for the pain," I begged. "Please, Aidan, let us do that."

He shook his head quickly. He sobbed louder when we tried to lift him once again. His breathing was too fast. His chest rose and fell deeply as he tried to relax his body enough to be moved. We managed to get him halfway up, but he stiffened, his walls flexing around my length again.

I felt a sting against my cheek and realised he'd slapped me. He wasn't all there behind the eyes, but fear flashed across his expression when he processed what he'd done. With his limp body in this position, it just made it too heavy for us to work with, so we let him relax back down all the way.

"Don't worry about the slap, it was reactive," I comforted him. "Talk to me about it when you're ready. If you even want to, I promise, you're okay."

"Let me re-... relax, please," he pleaded. "Just let me... do that. I-... I'll be able... able to move then..."

"Okay, sweetheart," I said. I kept my eyes on him but directed my next words to Irene. "Get a juice box, heat pack, and maybe a toy for him to cuddle. Would you like that?"

My hands went up to his hair, playing with it lightly. He slowly laid his body on top of mine, whimpering with the movement. He nodded against my chest and Irene immediately left the room.

"Shush, baby," I cooed. My fingers tangled in his hair, and I slid one hand down to his back, trailing my fingertips along his spine. "Just relax. It was a lot. You're going to be okay. I'm so sorry about the pain."

"I'm sorry," he whispered.

"What for?" I asked. "You have nothing to be sorry for."

"The slap," he answered quietly.

"It was nothing," I shrugged. I was indifferent about it. It was reactive, not meant to actually hurt me.

"The pain reminded me of... what happened and I," he paused. "I tried to fight back. I forgot I was here."

"I understand," I assured him.

His hand moved up to his face, wiping away the tears. He still sniffled and sobbed, but at least he was calming down. I could still feel his body reacting to my length inside him, the flexing, the squeezing. It was a weird mixture of pain and pleasure, my body wanted to impulsively thrust upward. An intrusive thought. He's already down there, just thrust, he'll get used to you faster. What's the harm? Him getting scared off was the harm. It's assault. What was wrong with me?

"Can I try to lift you off me again? I'll keep holding you. I don't want to be in you and causing more pain is all and we have to do it sooner than later."

He gulped but nodded. Irene had just come back, standing idly in the doorway. I placed my hands at his hips and as gently and swiftly as possible, lifted his body away from me. His attempt to stay relaxed had failed, however, it gave me enough time to fully remove my length from him. Laying him back down, all I could hear was the whimpers leaving his lips. My arms wrapped back around him, tracing circles over his spine and back.

Irene came over as he rested in my arms. I took the heat pack off her first, lifting Aidan so I could set it on my stomach. Lowering him back onto my body, he breathed out a sigh of relief. The heat should be resting just above his crotch, hopefully, it'd help. Irene held out a small stuffed koala toy and mumbled about it being the first thing she grabbed. It didn't seem to matter to Aidan who took it off her silently as well as the juice box.

"Are you okay?" she asked. She ran her fingers through his hair. "I didn't take it well the first time either. He's a giant." She joked, trying to make the situation lighter.

"Should put a warning on it," Aidan joked back.

I chuckled softly, trying not to move his body too much. He began sipping at the juice, relaxing a little more into me. My hand moved to his lower back, massaging deeply. He let out a small grunt of pain and I stopped in fear.

"No, please, it was helping," he requested, looking up at me. "Please?"

I nodded, continuing the massage. "You're not getting anything more for the weekend, it's only lessons for now."

He whined softly. "I have... other holes."

"Maybe we can get you to practice on some toys then try me in these other holes," I suggested.

"That... That would be okay," he whispered. "Practice would be good."

Irene sat back down in her seat silently. She kept an eye on us. She knew that if I needed her to reheat the pack or grab something else, I would ask. Aidan must have had so much going through his mind, so much I couldn't possibly understand, and this wasn't something I wanted to ruin. Definitely want to ruin his body one day, but not our dynamic. Fucking thoughts.

"What do you normally like to do?" he asked. "To your Subs, I mean. What turns you on the most?"

I wasn't sure if he was curious or if he wanted something out of knowing right now. I'd just hurt him, and he still had questions. If I started to explain what I wanted, I worried it'd push me into the headspace for it. Irene stared at me, a simple warning to stay silent.

"I don't think that's a good idea, Aidan," I said. "I'll tell you later."

"I can't be more scared than what just happened, well, I mean I wasn't scared. It was more of a shock. Surprise. I didn't think I'd shake that bad," he rambled on.

I covered his mouth with my hand. "If I'm in the mood after dinner, I'll tell you what I like. Is that understood?"

He nodded against my hand. I was just happy he didn't go silent, that he didn't need his whiteboard. I had a feeling that if I'm put in the mood by telling him, I may want to show him something I like, even if I was simulating it with Irene, or actually doing it with her, I might upset him or worry him that he might not be able to do it. I pushed that thought to the back of my head but not far enough away that it left.

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