Sammy Agrees To Shanas Game

A harsh alarm rang from his phone.

9 am on the dot.

Sammy cut the alarm off and sat up from his bed. Still blinking sleep from his eyes, he rolled over and went to get up from bed when he realized he couldn't move his arms.

The night before came rushing back. It had been two weeks since Sammy's last milking. He was getting pretty good at taking care of his business without the help of one of the three. Not that he hadn't been enjoying them or anything. He honestly fucking loved them. But part of him had been feeling like his milkings were partly punishments of some kind. He had been having conflicted feelings about it all.

Last night he had forgotten all of that when he got wine drunk with Eileen. Tommy was already in bed and Shana was out with a knitting circle. Or a witch circle. Sammy couldn't quite remember.

That had left just him and Eileen. They put on a few movies and shared a bottle. One bottle became two and soon they began making out on the couch. Eileen dragged Sammy to his room. She tittered happily. She told him she had hoped she'd get to milk him next. Sammy was made to bend over his bed and stay there until Eileen told him he could move. She brought out a slew of tools and toys to torture him with. Wasting no time, she lubed up his ass with two gloved fingers. Her other hand grabbed his cock in a vice grip. Eileen worked his ass loose until his cock was fully engorged. Once he was hard as a rock and panting softly, she started to make things interesting.

Pulling his hands behind his back, a pair of cuffs encircled his wrists. He had begun to protest before Eileen gagged his mouth. She shushed him pitifully, rolling the condom over his dick. Then came her last tool of the night. A butt plug, as thick as three of Eileen's fingers. She seemed to savor working it into Sammy's ass. Muffled moans came from behind the gag as she pushed and pulled, watching his ass stretch to accommodate. Once the plug was snug, Eileen flipped Sammy on his front. He moaned, feeling more pressure on his prostate from laying with the plug.

Eileen stripped off her jeans and underwear, showing off her curvy thighs for Sammy's viewing pleasure. She ran her gloved hands over his legs before pulling herself on top of him. He felt her rub her pussy against his cock, letting out a pleasurable sigh. She leaned in to kiss him, continuing to grind against him. They interrupted their kiss, Sammy's cock filling Eileen entirely.

"Oh..fuck" she moaned deeply.

Pushing against Sammy and arching her back, she began rocking up and down on him. Starting slowly and deliberately, each motion caused his ass to rock onto the plug. Sammy sat there helpless as his prostate was pressed on by the intruding toy. Eileen began to pick up the pace, gasping and whimpering as she felt Sammy's cock pulsing inside her. She dragged her fingers down his chest before turning them onto herself. With one hand she pinched and twisted her nipple. Her other travelled down to her clit, stroking in circles.

Coming close to overstimulation, Sammy's whole body felt like it was buzzing as he orgasmed. His body quaked and he came. Eileen could feel him beginning to orgasm and began rubbing her clit eagerly. A short scream of pleasure escaped her lips, forcing herself to cut it off before they could be overheard.

The last night came back to Sammy in a rush, standing up to find his arms still cuffed, and himself still naked. Eileen had been kind and present enough to remove the plug at least, but that hadn't helped how sore his ass felt. He hurriedly got out of bed and stumbled over to his desk to his phone. Except he had no way of getting the cuffs off and he needed to get ready for work.

His phone lay inert and he was considering the mental gymnastics of getting his phone with his hands cuffed behind his back. Sammy spent several minutes desperately, blindly clawing for his phone. Finally he grasped it! Now in his hand, he was considering the puzzle of unlocking and then dialing a number. But his hopes were dashed as he felt the phone slip and clatter to the floor below.

Sammy sighed.

-

Sammy managed to call his work, lying about a sudden stomach bug. In truth, he had been unable to find a way to at least get his arms in front of him. No luck it seemed. He had tried to fit the cuffs under his feet, but the cuffs were on a short chain and gave him no wiggle room.

Eventually he did spot the key laying on his desk. Now came the quandary of getting the key to the cuffs and freeing himself. He tried squatting towards the desk and grabbing at the key but found it just outside his awkward grip. Perching on his bedside, he reached out with his foot towards the key. If he could scoot it towards him, he could probably-

"Hey, I'm home!" a voice rang out through the house.

It was Shana, returning home from wherever they had been the night prior. Sammy's eyes shot open. It was a precarious situation he found himself in. Shana would be able to free him from his cuffs. But would they take his nudity as an opportunity for a milking? He hadn't even gotten breakfast yet!

"Hello, anyone home?" Shana's voice began approaching the stairs. Steps following one after the other.

Sammy began pulling at the key frantically. He wasn't sure of the outcome, but he knew more than anything he wanted free of these cuffs. The keys sat on the edge of the desk and Sammy twisted around to grab the key.

Shana had made it to the top of the stairs and was moving around. He could hear them calling out for the other two roommates, who had long since gone to work. The key twisted in his palm, trying to fit it into the keyhole on one of the cuffs. Metal scraped against metal and he felt it enter the keyhole.

"Sammy?" the voice came from his door.

The key clattered to the floor. Sammy had jumped when he had suddenly heard them at his door. He went to pick up the key as his bedroom door began to open.

"Are you here dud-" Shana began as their eyes fell on Sammy.

Sammy could feel his face flush. Shana's face went a bit red as well. A giggle escaped their lips.

Gulping down his embarrassment, Sammy spoke up first.

"Uh, would you mind getting me out of these cuffs?"

-

"So you were stuck like that all night?" Shana sipped on a cup of coffee. A smirk betrayed how amused they were by the situation.

"Thankfully Eileen was nice enough to take the plug out. God knows what would have happened by sleeping with that in" Sammy chuckled nervously.

Shana rolled their eyes, watching Sammy stretch out his shoulders. He was a bit sore from his precarious position the night prior. The two sat and ate breakfast, chatting about Shana's night. Sammy liked hearing about Shana's escapades, dabbling into weird things like the occult or witchcraft. It never made much sense to him, but they were always so enthusiastic it was hard to not be engrossed.

Shana left Sammy shortly after to go shower. Sammy sat and read the news, but his eyes glazed over the headlines. Instead, his mind wondered about why Shana had given him mercy. Perhaps they had been too tired or distracted from their night. That's never stopped them before. He turned the page and forced himself to read.

-

The afternoon rolled around and Sammy had begun mulling around the house. He did any chores he had gotten away with putting off up until then. He read a book, watched tv, played video games. It was about three PM and a fatigue took over Sammy.

A nap might not be a bad idea, he thought.

He took the stairs at a snail's pace, cresting the top and staring into Shana's room at the end of the hall. Their room was lit with blue LEDs, casting an unnatural hue to the scene. Shana stood in the doorway, wolf's eyes seeing Sammy as he reached the top step.

Sammy was frozen like Shana's eyes were headlights. He had considered simply saying hi and walking towards his room. Something in Shana's gaze, however, told him to keep walking. He stopped a step from them. Sammy was a few inches taller than Shana, but that gaze made him feel dwarfed.

"So this morning, I let you off for a little while, cause I just got back" Shana started.

"But?" Sammy replied.

"Buuut, I did catch you, clearly needing my help, and since I helped you, well, I think we need to make up for it now, right?"

"Like right now?"

"I suppose we could wait and I could tell Tommy. Imagine what Tommy would do if they found out you and Eileen were making a game of our little agreement?" A fox-ish grin crossed their lips.

"No way, Eileen would be in trouble too, you wouldn't throw us both under would you?"

"Why not, I'd get to listen to Tommy teach you a few new things you'd probably not be ready to learn, and Eileen would get a stern talking to" there was a certain confidence with which Shana spoke.

Sammy had a feeling Shana was bluffing. They always wanted to make a game of it just as much as Eileen. However, where Eileen used their agreement to throw herself at Sammy when she wanted, Shana wanted to get under Sammy's skin. They wanted nothing more than for Sammy to say-

"Okay, let's go ahead and do it then" Sammy relented.

"Perfect, come in and get naked. I'm gonna go get ready, just get on the bed where the towel is."

Sammy stepped into Shana's room. From their closet, Shana could be heard gathering together something. The harsh yellow of the closet light briefly pierced the tinted blue. Stripping down naked, Sammy sat on Shana's bed, a soft towel in the center for him to lay.

Shana emerged, holding a small tray of objects. They set it down near him, and began taking objects off it. Some of the objects looked like medical equipment. He watched as they pulled a pair of black gloves, before turning their hands to him. They grabbed Sammy's legs and lifted, exposing his ass.

"Hold your legs back for me" Shana's voice was sweet yet stern.

Sammy did so, feeling himself flush as he presented himself to Shana. They squeezed some lube onto their fingers and began spreading it liberally on his ass. Shana gently let their finger penetrate Sammy.

A small gasp escaped his lips, feeling their finger push deeper. In and out it went until he could feel it touch his prostate. Shana curled her finger, each motion sending a pulse of pleasure through his body. They hadn't even touched it yet, but his cock was already swollen and hard.

Shana added a second finger to his ass, twisting the two intruding digits as they went. They pressed against his prostate each time with purpose. Each time Sammy felt himself twitch. He could see Shana's eyes looking hungrily at him, like a wolf almost. When their eyes met his, they quickened the pace, their fingers pushing up to the knuckle before retracting. He could see a pool of precum leaking out of him as he struggled with the feeling of their fingertips hitting his spot.

They slowed suddenly. Shana kept their eyes locked with Sammy's as their fingers retracted. However, before Sammy could get used to the relief, he felt a third finger enter his ass. A loud moan of pleasure escaped him as Shana began thoroughly feeling around inside him with their three fingers.

"We've already stretched you out so much. I wonder how much we could fit inside you, eh Sammy?" Shana had a wry smile.

Sammy couldn't respond. What could he say? He was lost, on the verge of an orgasm, with his gorgeous torturer tempting him with more. The fingers exited his ass completely. He breathed in deeply, having begun sweating without realizing.

"We're going to test that tonight, okay Sammy?" Shana said, reaching for something on the tray nearby, "roll over for me like a good boy. This will only work if you have your ass up for me."

Sammy looked at Shana as they called him a good boy, feeling a strange flutter in his heart as they did. He did what they said obediently, turning over onto his stomach. Their hands gripped his hips and pulled him upwards, leaving his swollen dick hanging. He felt their gloved fingers wrap tightly around it and tug a few times.

Sammy dug his fingers into the bed and moaned pitifully as Shana stopped.

"Not yet. I'll give you one big one, all you have to do is let me play for a bit longer."

Something metal clicked behind him. Confusion went through him and he turned to look, but before he could Shana grabbed a handful of hair and forced his head into the bed. They forced their body weight against him, grinding their hips into his ass like how Eileen would when she pegged him.

"No peeking now, sweet boy, or I'll be a lot rougher than you want" their voice was cold.

He wanted to talk back, but he already knew that it would just get him in trouble. Or would it? He hadn't gotten so used to being told what to do by them, maybe he just didn't want to fight back anymore.

Doing as he was told, Sammy kept his head down and stared at the wall in their room. The metal clinking continued followed by the squirting sound of a lube bottle. Something ice cold and hard touched his ass. It felt metallic.

"Now breathe in" Shana's voice was sweet once more.

Sammy began to breathe in before it was cut short by the metallic object slowly pushing inside him. He moaned weakly as it finished moving. The sudden shift in feeling made it hard for him to even know if he was going to cum. It didn't hurt but his body quaked in frustration.

"That is a speculum, made for opening you up and looking inside you, isn't that cool?" he could tell Shana had a big smile on their face, "now if I start to turn this little thing here, it'll start spreading you open."

It was intense with just the speculum in him alone, he didn't know how he'd feel about it when it began to open. However, it was already too late when he heard the device clicking as Shana opened it. Sammy dug his nails into the bed covers tightly as slowly the speculum spread wider. Was he at his breaking point? Was this too much? No, because it seemed to go on forever.

"Ooh, I bet this is the most you've ever been opened," Shana's voice cooed from behind him, "I wonder if I could fit my whole hand inside you."

It took a moment for what Shana said to register. He mumbled something, a plea not to, but his speech was almost unintelligible. Soft gloved fingers traced across his back, Shana shushing him. They were petting him almost like he was a cat.

Suddenly, he felt lube being spread on his still rock hard cock by Shana. Gently and surely, they began rubbing Sammy. He could only whimper as they increased their pace. Shana wrapped their other hand around his balls, gripping them firmly and kept going. It wasn't long before Sammy's whole body convulsed, asshole tightening around the medical device left within him, cock pulsing in the gloved palm of his master. The orgasm may have been the most intense he felt since starting to live here.

Shana giggled after the convulsions stopped. Sammy couldn't tell how long it had lasted. He felt the cold of the speculum slowly retreat from inside him, Shana slowly bringing it back to a normal level before removing it. Collapsing onto the bed, Sammy watched as Shana collected their tools and brought them to their bathroom to clean. He noticed that they had a little bowl in their hand, with what looked like cum dripping off of the side of it.

Shana returned only a minute later and sat next to Sammy. They gently took a moist towel and wiped his cock and anywhere lube had gotten during the event. They smiled gently at him and reached over to touch his cheek. They caressed it, a blush forming on their face.

"You were a really good boy today Sammy" Shana said, their voice saccharinely sweet.

It was hard to say what was going on in his head. His body had been on autopilot for most of the last couple of minutes. Sammy could only think of one good response.

"Thank you."