Avery's Night of Punishment

Avery knew she was in trouble. When Sir called earlier, he asked what she did last night. It seemed like a harmless little fib of omission at the time when she replied, "Nothing. Take out and TV." He gave no indication that he knew she wasn't telling the whole truth. But now, driving over to his place, she just knew in the pit of her stomach that he knew.

Decked out in PJs and settled in with the remote, Avery mindlessly flipped through the channels. A Hallmark movie was just starting when the phone rang.

"Hello?"

"Bitch, where the hell are you?!?"

Avery laughed at her friend Noelle, "Home, wherever you are sounds loud."

"Get your butt to Indigo! That DJ from New Year's is here and I've got Molly."

Normally, Avery wouldn't have had a problem sticking to her plan of a relaxing TV night. But the week had been stressful with work... and she missed her Tuesday session with Sir because of her dad's birthday. What she really needed, was a night of mindless fun with her friend.

After throwing on her good black 'club dress,' a heavy dose of eyeliner, and some heels, Avery jumped in an Uber and was at the club in less than an hour. Quickly, she found Noelle and a stiff drink.

Throwing her head back, dancing to a Rihanna song, Avery felt blissfully happy. Sure, maybe Molly helped get her there, but it was fucking fantastic. Grinding between the two young men, without a care in the world, a brief thought of texting Sir was gone before it was even fully formed.

Avery drove to Sir's house thinking of what may be in store, and nervously chewing on her lip. He couldn't possibly know she went out last night, could he? It was Saturday night, one of their usual session times. They tried to keep a schedule of 'play nights' on Tuesday and Saturday and the rest of their time was a normal vanilla relationship. Truly, Avery felt like she had two hot men in her life -- strict and demanding Sir twice a week (and more when they both needed it), and Brad as her loving boyfriend the rest of the time. After several years together, they had the role play down to a science. Avery couldn't imagine how she could be happier or more connected to a partner.

Brad was not on her mind as she pulled onto the quiet rural road. Only Sir. On these drives, Avery always had to remind herself to be careful. It was so easy to get distracted by the nervous anticipation and suddenly -- a deer... or groundhog, or rabbit. God forbid a cyclist.

She brought her mind back to the road and tried to focus on only that until she pulled into the circular drive of the large Tudor house. With a final deep breath, Avery grabbed her purse off the passenger seat and steadied herself for the night ahead.

He never ceased to make her shiver. Sir's dark good looks made her heart skip a beat every time she saw him, even if only a day had passed. She couldn't resist running a hand through his sexy tousled black hair as she stood on tip toes to give him a kiss. She let her hand run down over his faded tee shirt, feeling the hard muscle underneath. Already, Avery could feel her panties getting wet. He always had that effect on her. And lately, as their sessions got more and more intense, she just felt closer and more attracted to him.

They went straight to the play room, preferring to save drinks and conversation for later in the night -- after they were spent and blissed out from the exertion of their activities.

Avery quickly stripped out of her clothes, folding everything neatly and placing the small bundle on a chair in the corner. This was their ritual.

She slipped into her position, naked and kneeling on the plush rug at Sir's feet. He was barefoot, but his jeans and tee would stay on until he saw fit.

Avery stared at his feet and waited. It was warm enough in the room that she didn't feel overly uncomfortable in her nakedness.

"Avery, I'm very disappointed in you," his deep voice made her heart flip. "Do you know why?"

Ugh, he does know, Avery thought to herself. Oh fuck... unless I did something else!? She stalled for a second, running through anything she possibly could have done to breach his rules.

"I think so, Sir."

"Mmm, I bet." Avery kept her eyes downcast as he ran his hands through her long hair, absently brushing it over her shoulder.

"You thought it was appropriate to take illegal narcotics at a nightclub, jeopardizing your safety, while putting yourself at risk with not one, but two men."

"No -- I --" Avery couldn't get her protest out before Sir cut her off.

"I'm not done!" His harsh voice cut through the silence of the room. Not loud, no never loud. Just so so commanding.

"I have it on good authority that you let two men put their hands all over you. I don't want to hear your excuses that it was just dancing. I think my little Avery liked having the attentions of two men."

Avery's thoughts spun trying to think of the angle he would try to play this from. Not jealousy, he wasn't that type.

"Honestly, I can't be too upset with you," Avery almost sighed in relief until he continued, "it's my fault really. Obviously, you have needs that aren't totally being met, and that is my most important job."

Sir tipped Avery's chin back so he could look at her, "My sweet Avery, we are going to have quite the night."

Sir helped Avery up and directed her to the St. Andrew's Cross. Turning her away from him, he pulled first one wrist into the leather cuff and pulled it as tight as it would go. Letting his hand graze across her ass, he moved on to the other hand. With both wrists tightly fastened, he picked up the spreader bar from the shelf and moved between her ankles.

Sir fastened the leather strap around her ankle. "Wider," he commanded, spreading her ankles uncomfortably wide. With her ankles so far apart and her arms on either side of her head, Avery was tipped forward slightly, giving Sir delicious access to her tight ass.

As he moved around behind her; Avery anticipated the first blow. Would it be a sharp sting or a heavy crack? The crack won out as she felt the hard paddle against the fleshy roundness of her butt. Blow after blow came down across each cheek. First one, then the other, then low, then high. After several minutes, she heard the paddle placed back on the shelf and took a breath. Next was the cane. Avery wasn't a fan and always felt it hard to deal with. Just when she thought her pain tolerance was ok, out would come the cane to put her in her place.

"Ahh!" Avery couldn't help crying out as the cane snapped across her ass. Involuntarily, she pulled against the restraints, immediately unsure if she could take this. Another crack and another shriek from Avery.

"Mmm," Sir ran his hand along her thigh and between her legs, "See, your timid little screams say 'no,' but this says 'yes.'" His fingers trail through her wetness and one thick finger pushes inside of her.

"I love how the pain makes you so wet." He fingers her slowly and trails his wet finger back along her ass. Avery hears the lube snap open and then his finger is back, lazily trailing around her asshole. Slowly, he pushes the lube inside of her, his finger making her moan. Their anal play has been one of Avery's favorite things. At first, it was overwhelming and she wasn't sure how she felt about it. But, the orgasms were evidence of their own. She never came harder than when he fucked her so deep and hard while a plug was stretching her ass. His huge cock making her pussy stretch open and putting so much pressure against the toy in her ass caused the most intense feeling she had ever experienced. The first time they did it, the orgasm was so powerful it brought tears to her eyes.

Avery mourned the loss of his finger as he pulled the thick digit out of her tightest hole. Snap! The cane was there again and Avery let out another sharp squeal.

"What am I going to do with you?" Another strike and another shriek. "So greedy for anal play that you go so far as to seek out TWO men at the club!"

"No, no, that wasn't --"

"No talking," Sir quickly silences her. Three quick cane strikes in succession and Avery can feel the tears on her face. Thankfully, she hears Sir slip the cane on it's hook and then his hands are caressing her. He rubs her ass and back and shoulders, giving her a moment to recover.

Avery gasps as she feels something cold against her asshole. Sir leans down so his lips are against her ear, "This plus is very big. You're going to have to relax as much as you can to take it," he starts pushing in and Avery tries to relax. He doesn't let up the pressure as he gets to the wide middle.

"Owww, wait!" Avery can't help crying out. Her ass feels like it's burning as the toy tries to force its way inside her.

Sir pauses, keeping the toy where it is, letting Avery's ass struggle around the girth of the thing, "You need to take this toy, Avery, or it's going to make the rest of the evening that much more difficult." His words distract her enough that he's able to push the toy in to it's widest point.

"Ahhh!!! Stop, stop, please!" Avery tries to struggle against him as he holds the toy, not letting it slip in to the narrower end.

"I know," Sir kisses her shoulder gently, "I know it hurts." His gently voice gives no indication that it's him inflicting the pain. As he twists the toy cruelly against her protesting asshole Avery can't help her begging, "Please!!! Owww, please, I can't!"

"You can." Sir slowly presses the toy in the rest of the way, letting Avery catch her breath. After only a moment, he tugs it slowly from her, again the widest part opening her asshole far greater than it has been before.

"Unghhh!" Avery tries to breathe through her tears. She knows she can beg, but he won't stop. Her asshole is momentarily empty as he pours the lube against her and onto the toy. Again, painfully slowly, he works the toy back into her ass, rubbing her back as she cries and tells him it's too big.

"I know baby." All the way in now, Sir twists the toy lazily; pressing it in a out of her ass. "This is what's going to happen," Sir presses the end of the toy hard with the heel of his hand, making Avery whimper as the tears continue to stream down her face.

"A man named Ben is going to join us." Avery gasps, not quite sure she heard him right. "He is a big guy, muscular, and his cock is fucking huge." Sir keeps twisting the toy in her ass, making her feel every millimetre of it.

"Ben has been kind enough to agree to help me out tonight."

Avery's mind races. Is he going to let Ben whip her? Is he going to watch Ben fuck her?

Sir chuckles, "Your face right now is priceless," he kisses along her neck and back up to her ear, letting his fingers pluck at her nipples.

"Ben is going to keep your pussy company with his big cock, while I break in your tight fucking asshole." Sir rips the toy out of her ass, making her scream.

"Ohh, no, not yet baby. There's going to be plenty of time for screaming later." With that, he rams the toy back into her ass, leaving her heaving against the cross, crying and begging him to stop over and over.

After pausing for a glass of water, Sir returns to Avery. First, he removes the spreader bar, and then unties her wrists. He helps her off of the cross and onto the bed.

"How do you feel?"

"It hurts, p-please, take it out," Avery tries to find a comfortable position that takes the pressure off of her ass, but she fails.

"We need to leave it in, my cock is bigger than that thing and you need to get used to it."

"I-I don't think I can, it's t-too big," the thought of Sir's cock in her ass is unimaginable now that she's experienced this monster plug.

He just laughs, "Well, you are going to have a tough night then," clearly Sir has no intention of changing his mind for the night's activities.

"Ben is waiting in the other room. When I call him, he is going to come and join us. I expect you to show him the same respect you show me. Do you understand?" Avery manages a nod, making a mental note not to bite the nice man's cock.'

"I'm going to do you a favor," Sir caresses Avery's face, making sure she's looking at him when he says, "I'm going to take your anal virginity before we take you at the same time and you feel what it's like to have two huge cocks split you open."

Avery can only stare at him in disbelief, "I don't know if I can, this toy really hurts, I don't think --"

He cuts her off, "It wasn't a question. This is what's going to happen, and you're going to accept it. If you need to cry and whine, I won't gag you, but keep in mind your future punishments will be based on how well you do or don't take this."

Avery meets his eyes, taking in his words. He couldn't be more serious. He's going to hurt her tonight, a lot, and she needs to accept it. He picks up his phone from the side table, "Come on in."

The man who comes into the play room is big, Sir wasn't kidding. He's a bit taller than Sir and even more built. He's wearing only boxer shorts and Avery can already see the outline of his massive member. Ben joins Avery on the bed and leans in to kiss her as his hands brush over her breasts and down her side. Only caught off guard for a moment, Avery kisses him back. This is what Sir wants.

As Sir starts stripping off his clothes, Avery sinks into the bed with the handsome stranger on top of her. His lips are soft and he's an excellent kisser. Her body starts to melt and the toy in her ass feels almost good as he swells against her. Ben pauses to shove his boxers off, letting Avery get a good look at him. Holy fuck is all she can think as she marvels at her luck and the two sexy men at her disposal. Easily, Ben and Sir have the biggest cocks she's ever seen, long and impossibly thick with pronounced veins and bulbous heads to make her mouth water. Ben strokes her pussy as Sir climbs onto the bed and offers his cock for her mouth. Trying to concentrate on her oral skills, Avery is distracted as Ben fingers her deeply. She's panting and on fire when Ben positions himself over her. Sir moves to give them space as Avery feels Ben's cock at her opening.

Slowly, Ben's cock head penetrates her and Avery can't help the whine hissing out of her mouth, he's so fucking big and the massive toy is lodged in her ass.

"Shit, your pussy is like a clamp," Ben grits his teeth trying to force his cock inside of her tight cunt.

Tears spring to Avery's eyes as she tries to accommodate the girth of Ben along with the toy.

"Do it, now." Sir's clear voice is next to Avery and she sees the look of sympathy cross Ben's face before he slams his cock into her, forcing her to take all of him to the hilt.

"Ahhh!" Avery cries out, trying to move away from him, but it's impossible. His massive cock is pressing against her cervix and she feels like she'll split in two.

"Fuck her, now, hard," Sir commands.

Ben immediately responds and all Avery can do is claw at his big biceps as his cock pistons into her over and over; the toy rubbing her ass raw. The sensation is so overwhelming that before she knows it, Avery is cumming again and again in an endless orgasm. There's a pop as her muscles contracting in combination with Ben's massive cock force the plug from her ass. She holds him like a life preserver as she buries her head in his neck and waits for him to cum.

"Avery, wake up," Sir runs his fingers along her cheek as her eyes blink up at him. Ben plays with her nipples absentmindedly, knowing that he doesn't need to play a role in this next part, aside from moral support.

Sir flips her onto her front without warning and pulls her down to the end of the bed. He grips her cheeks and spreads them cruelly, "Mmm, this is going to be so good... for me."

He opens the lube and pours it liberally onto her asshole as well as his cock, "Ben, hold her arms please."

Avery whimpers as the fear courses through her. Sir stands behind her, pulling her up onto her knees by her hips as Ben pulls her arms out in front of her and grips her wrists tightly against the bed.

Sir holds his stiff cock, pressing the bulbous head up against her opening, "Try to relax Avery." With that, he presses forward, not relenting until the head pops inside of her tight opening.

"Ahh!" Avery cries out at the impossible stretching, sure that he has just torn her. "S-stop, wait, p-please!" She tries to evade him, but he holds her hip tightly, Ben now gripping her shoulders, holding her in place as she cries.

"Yes, fuck, Avery," Sir groans as her warm ass grips his cock in its vice. "No, I won't be stopping, this feels so damn good." He presses into her, forcing her ass to expand rapidly to take more of him. Avery's body shakes as she tries to cope with the pain coursing through her. She screams into the mattress, blankets in her mouth, as Ben forces her back onto Sir's massive shaft. Sir is unrelenting, pushing more and more of himself into her, deep into her colon, until finally his thick balls are pressed tightly against her.

"Oh fuck, Avery, this feels so fucking amazing," Sir groans against her ear while he squeezes her breast, trying to jam his cock even deeper into her bowels.

"P-please," Avery cries against the bed, "it hurts."

"Oh," Sir pants, "I know, my poor sweet girl. Your poor ass opened up so impossibly wide." He leans back so he can run his finger around her opening, circling his cock. She hears the click of the lube again and Sir is dragging his cock out of her so he can pour more of the warm wetness on both of them.

"Ben, maybe you can give Avery something to distract her while I abuse her asshole?" With a chuckle Ben gets into position and lowers Avery's head over his cock. Between screams and whimpers she attempts to suck his cock, her lips straining around the girth.

Sir laughs, "Ok, you can stop." Avery gasps as she lets her head rest on the bed. "Ok Av, I'm going to really fuck your ass now. I know it hurts, so I'm going to let you scream if you need to. Ben, why don't you hold her hand?"

Avery takes a deep shaky breath as Sir pulls his cock completely free. He waits a moment as her ass spasms and tries to close. Ben grips Avery's hand tightly and strokes her hair gently. Next, Sir penetrates her ass with considerable force, slamming her body back into the bed. Avery screams feeling her ass split with the force of the penetration. She keeps screaming as Sir fucks her ass hard, making her take his cock hard and deep over and over again. Finally, almost out of tears and voice gone hoarse, Sir cums deep inside of Avery.

When Avery next wakes up, Sir is coaxing her with a glass of water.

"Is it over?"

"No darling, not yet." He strokes her cheek gently.

Avery starts crying anew, "I can't take anymore, my ass and pussy are so sore, please."

"Shh, none of that." Sir takes the glass and returns it to the side table. Avery glances at Ben, sitting on the side of the bed. He watches her intently as he strokes his massive cock, hard once again.

"It's the main event baby, so you only have to take a little more. Ben is going to get a shot at that tight sweet ass of yours, while I take your cunt. We're going to really open you up this time. You're going to have to be very brave to take what we give you." Sir gently rubs Avery's back, letting her cry against the blankets.

"Please," Avery begs, "My ass feels torn, I can't take him, I can't take both of you!"

"Shh," Sir turns Avery onto her back, "I want you to do this, so you're going to do it. I know it hurts, but you take it for me." He kisses her tears, "Yes, give me all of your pain, sweetheart." He dips his head down to her pussy, licking her slowly and easing a finger inside of her, making Avery mew.

"Yes, that's right, we're going to go slow," his tongue sweeps across her clit again and again as the tightness builds in her. He pushes Avery into a gentle orgasm, letting her coast slowly back down.