Dean took his brothers balls in his hand and squeezed them, making Sam cry out in pain.

"Fuck! Dean no more... Ahhhhhh! goddamn it, I don't think I can come again."

"What would you do Sammy? If Cas was here? Think you can make him come with that pretty little mouth of yours? Would you take him deep into your throat and let him fuck it? Or would you just tease the slit like you do to me until he begged for more?"

Sam let out a strangled moan, his mind was unable to form sentences anymore.

"Fuck my throat Sammy. Show me everything you want Cas to do to you."

Sam's body felt horrendously empty when Dean pulled out, and unfortunaly the toy seemed to be stuck at a very uncomfortable angle. But at least it gave him some momentarily relief.

Deans hot mouth was around him in seconds, making him buck up in suprise. Sam gave little thrusts, not comfortable with more, and Dean seems to realize that Sam was struggling, so he began to bob his head to help.

He gripped the bed sheets hard. The stimulation in his ass combined with Deans mouth around his cock had him stumbling off the edge in record time, but when the toy continued to buzz, Sam's body screamed in protest.

"Dean- the toy! Ah- turn it off- yello- fucking hell- red! Ahhh!" Sam cried and fumbled looking for the remote. The vibration hadn't stopped and the toy was quickly becoming agonizing.

Dean scrabbled off his brother to look for the remote. It had gotten stuck between the bed sheet and the duvet. He turned the dial to off before setting it on the side table, to avoid any accidental bumping.

"Shh Sammy it's ok. I got you."

Dean sat against the headboard and pulled Sam into his lap, brushing his hair out of his eyes. "There, is that better babe? I'm sorry I didn't know it was hurting you..."

Sam gasped in relief when Dean turned off the toy. He panted into his brothers arms for a moment, and when he caught his breath, Sam sighed heavily.

"Good reflexes Dean" he chucked and winced as he rolls his hips. Sam tried to move his inner muscles, and groaned when the toy caught again.

"Dean... have you ever fisted anyone?" Sam asked bluntly, by way of describing his current predicament.

Dean laughed at the seemly random question, "Um, no I haven't actually. Why? have you?"

"Yes, and your about to get a crash course because I am not going to the doctor for this." Sam said, pointing to his stomach. "If I show you how, do you think you can take the vibrator out?"

"Whoa! Damn, its really stuck?" Dean asked, concerned and frankly nervous as hell.

"Yea.. It's pretty uh, up there..." Sam groaned and figited again. "If your not comfortable I'll go to the doctor. It's alright. Damn I was sloppy, should have just used a dildo."

"No baby, I'll help you, thats my job remember? Take care of my master?" Dean said shakily. It was hard to be convincing when he was so damn nervous.

He helped Sam lay on his back and placed a pillow under his hips. "you're um, you're going to have to walk me through this Sammy." He stated, not even knowing how to continue.

"First, you're going to grab a glove from our bag, the lube applicator, and the water based lube. Fill the entire syringe with lube and push it inside me. Then roll up the glove as far as it'll go. It should stop at your elbow."

"Alright," Dean pulled himself off the bed to dig through their bag of stuff from Dr. John's, the stuff they were actually able to make it out with. Dean grabbed everything he needed and sat back on the bed and filled the syringe with the lubricant. He placed the plastic tip at Sam's entrance and pushed the plunger.

"Ok, now what baby?"

Sam shivered as the cold lubricant entered his body. He began to work on relaxing his inner muscles. This wouldn't work out if he panicked.

"Take some more lube and coat the glove with it. As much as you can Dean. Then work me open like you usually would. When you get to your pinky, I'll guide you through the rest. Keep in mind once your arm is inside, me you cannot yank it out under any circumstances. Lube or not I'll tear."

Dean nodded and stayed quiet so Sam could continue.

"And it's going to feel very tight when it gets close to halfway up your arm. When I'm stretched that far, my body will begin to clamp down every few seconds to compensate. It's going to feel like a vice, and you may lose feeling, but you can't take your arm out when you are that far in. Do you still want to do this?"

Dean swallowed. "Do you trust me Sam? That's the more important question."

"I've trusted you with my safely during a fight, my sanity after Jessica, and now my heart. I trust you compleatly Dean."

"Ok then. Let's do this." Dean said, exhaling quickly and pressing the first few digits into Sam.

"Do you want to hear about the first time I did this?" Sam asked and Dean raised his eyebrow. It made Sam chuckle. "I'll take that as a yes."

Sam lay back on the bed and steadied his breathing while Dean worked.

"It was part of a series we did on bareback and large insertion." Sam was just able to catch Deans blush.

"I had been training. For weeks with one of the masters of the house, and my scene involved me on all fours, tied to a 'bitching board.' Basically a curved table with a dip so my ass was up and exposed. He started up with two fingers, then four, and-ah- worked his fist inside me. He fucked me like that for a while, and then he brought out the machine."

Now Sam was blushing, but the story was helping him focus.

"It was a thruster on wheels, -you've seen them Dean- but this one wasn't hooked up to a power tool. It was especially manufactured for long term use. At this point I was so stretched out I couldn't close if I tried. So he pushed the toy in me and I could tell right away from the shape of the head which it was. It was over 11 inches long Dean. That's longer than your entire forearm. And it was over 7 inches around.

There was a betting pool to see how far I could take it. I've seen one, almost two guys nearly hilt it, about an inch off. If I took it to the root, I would get free beer for two months, and my name on our wall of 'super slutty feats.'

Sam groaned when Dean added his fourth finger and began to spread them wide.

"So, anyways I relax, do my breathing, and he started the machine. Oh god Dean I nearly came when it breached me. It pushed forward slowly, I could feel it against my prostate the entire time. It stretched me more than anything I've done before or since. It just kept coming and coming dean, so goddamn thick and long.

My master kept me calm, bless him, and slowly I neared the end. I was four inches off, but like hell I was going to give up. Winchesters dont give up. I asked for more lube and when they did, something in me shifted and the next thing I felt was the cold metal against my ass.

Not only did I take the whole thing Dean, but when they unscrewed it, I was actually able to close behind it. Everyone cheered and apparently I broke some sort of porn recorded Dean. They gave me free beer for a year and put my name up on the board. And uh, that's also how I got my nickname 'slutty Sam'."

"...Jesus." Dean panted and Sam laughed in relief. At least Dean didn't think he was gross.

He felt Deans thumb begin to push against him and got back to the task at hand.

"Ok, twist your wrist now and pop your hand in. When I close over your wist, keep it level and push in a steady slow motion."

Dean twisted his fist and pushed his hand through the final barrier. He let his fingers uncurl slowly, watching Sam for any sign of discomfort.

"Hey Sammy? You uh, you don't happen to have that on film do you?" Dean asked shyly and Sam's face split into a wide grin.

"Oh yes. I'm pretty sure Ash has her own copy too. It was one of my best sellers."

"I want to watch that some time." Dean whispered, and Sam bet that if he looked down Dean would be hard.

"I'll ask Ash if she still has some copies available- oh fuck." Sam groaned, his body beginning to reject the movement. "Ok, now push only as fast as my body will take it ok? If I go quiet it is because I'm focusing on my breathing."

"I'll take care of you Sammy, don't worry"

Sam smiled and worked on relaxing as much as he could. As Dean worked himself in deeper, Sam could feel his cock fill with blood. Dean was nearly up to his elbow now, and Sam was struggling to stay loose.

"Dean- y-you should be close by now. Ah fuck-" He gasped and clamped down incredibly hard. His body was trying to close with Dean still in him and Sam began to hyperventilate.

"Sammy, shh baby shh it's ok," Dean promised. He held incredibly still and kissed Sam's hip bones. "Breathe, remember?"

Sam squeezed his eyes shut and nodded, trying to imagine Dean thrusting into him with his cock, anything to take his mind off this.

"I think I can feel it Sammy."

"Ah- Dean... Dean you have it now right? I can't-Oh please..." Sammy murmered and screwed his eyes shut.

Dean felt the toy press against his finger tips. He used his fingers to pull it against his palm and sighed when he held it completely. "I got it baby"

Sam gasped in relief. "Oh thank god... Dean, I love you.." He panted and made a near inhuman squeal as Dean began to ease out.

The draw was amazing. And Sam felt his cock twitch. He bit his hand to keep from moaning.

"Oh... Dean, that feels so good..."

Dean grinned wickedly as an idea popped into his mind. He rotated the toy in his fist upward and pressed it against Sam's prostate and rubbed in small circles.

"Let me know if it's too much."

Dean turned the knob to low. The toy buzzed softly in his hands. He hoped the stimulation would feel good and not hurt his brother. He desperately wanted to watch him come one more time.

Sam arched and writhed at the renowned stimulation. He was already so close to overstimulation, but he knew he could come once more before he'd have to stop.

"Fuck feels so- damn good. C-Can you move your fist? Just a little, I'm so close..." Sam cried and gripped the sheets hard.

Dean licked his lips and nodded. Sam was so damn hot like this. And because of him.

Dean pulled his arm back slightly before pushing back inside.

"Come for me Sammy, I wanna feel you clench around me. Come Sam. Now"

Sam bit his lip hard enough to bleed. It was getting to be too much, he needed a distraction before he lost it.

"Dean..." Sam begged looking at the knife on the counter, hoping Dean picked up on his hint.

"You want more?"

Sam nodded quickly

"kinky little bitch." Dean chuckled, reaching for the blade with his other hand. He placed the blunt end of the knife against Sam's hot skin, taunting him with the threat of a knick.

"Come on Sammy, come for me and I'll give you what you need."

He began to trail the blunt side up Sam's cock and suddenly it was all over. Sam screamed as another orgasm tore through him. He clenched around Deans hand so hard they'd likely both have bruises the next day. Come spattered across his stomach and chest, adding to the dried marks from before. Sam collapsed in a panting, exhausted heap on the bed, trying to regain his breath.

Dean set the blade down on the mattress and turned off the toy, taking it back into his fist. Sam was still spasming around him, so it would be a moment before he could completely pull out.

He spent the waiting time kissing every inch of skin he could reach to soothe and help relax Sam.

"Y-You can pull out now." Sam croaked, his voice hoarse from screaming.

"You sure?" Dean was still weary

"Yeah, just take it slow." Sam said, relaxing completely and opening as much as he could for Deans hand.

Dean was able to ease out his hand realitivly easy and with little to no pain to Sam. He washed his hands and returned with a washcloth and a cool glass of water.

"Can you drink this for me while I clean you up?" He asked softly and Sam nodded, smiling up at him with tired eyes.

"Did you still want me to mark you?" He asked, depositing the washcloth on the table now that Sam was clean.

"P-Please."

Sam's head swam with the mixture of fear and arousal. He loved being at the mercy of Dean, just the feeling of having so much power over him was intoxicating.

"Anywhere..I need it..." He whimpered, and practically drooled at the sight of dean dangling the knife over him.

"I know just the thing"

Dean placed the tip of the blade right next to Sam's left hipbone, just above his pelvis. He pushed in a little hard and let the blade drag diagonally across perfectly sculpted, tan skin. He watched as Sam arched up into it and Dean leaned down to suck the blood drops.

"Beautiful" He groaned as he made a mirrored cut half an inch away from the first. "That's a good boy Sammy, almost done. Just a few more."

Dean dragged the blade across Sams skin again, starting at the top of the first mark, making short, shallow cuts in a spread out M pattern. Dean grinned down at the crudely drawn heart beading up on Sam's hip.

"Looks good on you babe."

Sam raised himself up on his elbows to see the beautiful mark his brother gave him and smiled.

"It's perfect Dean, thank you." He said and nuzzled his lover before kissing his neck. "I love you so damn much Dean."

Dean brought Sam's face close to his and kissed him, whispering an 'I love you too' between kisses.

Sam held Dean against his chest, snuggling into the covers now that they were both sated and clean.

"Are you sure about tomorrow? I need to hear that you are ok with everything we discussed" Sam asked, while stroking Dean's tousled hair.

"I'm positive. Im really excited for everything you're gonna show me. I can't wait to be yours."