Double Trouble

Max was still in shock as his friend groped at his body. As Tara nibbled on his neck Max tried to understand what was happening. Tara’s reassurance about their friendship helped, but it all felt so weird and unexpected.

“Did you guys plan this?” Max asked Tara again.

“Maxine, I’m telling you the truth when I say, I did not think you would still be here when I got here. I should have told you about Harry but by the time I realized you were his little pet at the office you were so excited about him that I didn’t want to ruin it. This isn’t some conspiracy.”

“Yah Maxine, I didn’t realize you and Tara were friends, I also would have said something.” Harry seemed apologetic but was obviously anxious to continue where he left off.

“Okay, that makes me feel better. I thought I was crazy for a second.”

“Nope, just a weird coincidence. That said, Maxine I am incredibly horny right now. You look absolutely delectable strung up like this and Harry and I are eager to start torturing you again. Don’t ruin my high, so please drop the small talk, that voice should only be used for screaming and begging tonight, got it?”

“Yes, got it.” Tara spanked Max’s ass hard, the bruising and reddened flesh of his glute stung all the more.

“Mistress will do for tonight. I am your mistress tonight, not your friend, got it?”

“Yes mistress.”

“Good girl.” Tara kissed Max again. “Harry, I am getting dangerously turned on, I need to blow off some steam but I know she’s your gift, what’s next?”

“Well we did some whipping, some light clubbing, some nipple clamps and the weight that’s still on her.”

“You got busy pretty quick.”

“Yup. I was thinking of either putting her up on the cross for some more intense warm up or tying her down to the horse for a full workout.”

“Ooh, I would love love love to use my new toy you got me if you think she could handle it.”

“We were actually planning on doing some dilation, so maybe after that?”

Max listened to his coworker and best friend discuss how they would use his body next. It was an odd feeling, he’d felt like a piece of meat at the office many times but this was different. It was like they were having a casual conversation but the subject was how next to cause him pain. It was also kind of hot. The sterile nature of it in contrast to the **** struggle of enduring the pain so that the pleasure could follow. His shoulders were beginning to ache as he hung slack in his chains.

“Horse it is.” Harry agreed and came over to Max. He had clearly noticed Max’s discomfort and began taking him down from his hanging position. Tara knelt and removed the donut. Relief flooded into Max and his head felt light and airy. It was a euphoric feeling, weightless and present at the same time. The couple massaged his shoulders and rubbed him with oil. They paid special attention to any bruising and asked him if he was okay. Tara began massaging the oil between Max’s ass cheeks, probing his hole with her gloved fingers. Harry pulled the pin on Max’s collar and took hold of the leash, as he pulled it constricted Max’s throat. His dick sprung up immediately as they led him to the bench.

“Lay on your stomach, your knees go here and your wrists there.” Harry and Tara helped Max into position. His stomach lay on the long pad and his knees and wrists were slightly below that, strapped in by leather cuffs. His ass stuck out over the back of the horse and his cock hung just past where he lay. There was a rest for his head but he kept his head raised so that he could watch as the couple tied him down.

“Gag or no gag?”

“Either is fine.” Max answered.

“I wasn’t asking you.” Tara laughed.

“No gag is fine. We might want one later to keep the noise down.” Max felt the excitement and nerves welling in his gut again.

“I can’t take it anymore.” Tara said and sidled up in front of Max. She positioned herself on the pad in front of Max’s face. “You know what I want.” Max pressed his face into her warmth and extended his tongue. He drew his tongue from the warm hole up towards her clit, the skin was smooth and puffy. Tara sighed as if a great weight had been lifted from her and pressed her hand against the back of Max’s head. Max continued his slow exploration of her womanhood, intentionally teasing her. Even as she pressed his face against her Max avoided applying more pressure, allowing his nose to scrunch against her pelvis but maintaining a light touch with his tongue. Tara squirmed as Max began to taste more of her.

“Do it like you mean it or Harry will have to punish you.” Max ignored her, continuing to tease with the tip of his tongue, playing it along her lips and avoiding the spots he knew she wanted him to pay attention to. Max heard Harry walking around the room as he played his game with Tara. He knew his punishment would come either way, Harry’s sadistic desires required that Max feel pain. Max felt Harry behind him, his fingers began rubbing warm lube onto his exposed entrance.

“You feel that Maxine? Harry can either be gentle or he can be Harry. If you don’t take this seriously I will make sure you get the worst possible version.” Max smiled and continued as he was. He shifted his head and bit lightly at Tara’s inner thigh, following it with a kiss. “Harry, she’s being defiant.”

“Understood. Don’t worry, I think we can break her with this.”

Tara giggled. “Ooh Maxine you’re in for it now.”

“Maxine is enjoying this.” Harry said, he brushed Max’s hanging erection as if to tell Max he saw it. Max felt something metal press against his tight hole. He clenched without thinking and Harry pressed harder. It was smooth but Max could feel small ridges across it’s surface. Max moaned as Harry pressed the tip past his defenses and it sank into the soft flesh of his asshole. It grew large as it went reminding Max of the many buttplugs he’d used. It wasn’t particularly wide but it slid further than most of his plugs, reaching a familiar spot that his dildo often occupied. Then it stopped.

“That wasn’t so bad.” Max said between lapping at Tara’s coochie.

“Look at this Harry. I’ve never seen this side of you Maxine. You heard her, let’s show her why she should be scared.”

Max could hear metal clinking against metal and the pressure in his ass began to increase. It was as if the plug was growing. As it continued Max felt the distinct pieces of the plug separate like claws pressing outwards. He moaned as his hole filled and the slight discomfort tickled his prostate.

“Keep going Hare, she’s enjoying it. I knew you were a little butt slut but this is too good. You like the pear?” Tara gripped Max’s hair as Max focused on the expanding claws in his tender hole. The clinking continued and the pressure continued to build. Max felt a slight panic as the pain started to override the satisfaction. He felt the metal claws tearing him open from the inside, pressing his walls outward in every direction. Max let out a moan that turned into a groan of pain. His cock twitched as he felt the familiar submissive part of him enjoying the slow destruction of his asshole.

“This is an ancient **** device. Very traditional. In the past they would insert it and use a screw to turn a gear which would open the claws. Anything around it would be pushed aside, but when it’s inserted into someone that can be quite painful.” Harry was clearly enjoying the explanation. Max started breathing harder as he tried to manage the pain. Harry had not stopped turning the screw and Max felt like he would be torn to pieces. “The genius of it is, if you use it correctly, the sphincter is the last thing to break. You can open it quite far, prying the colon to a gape but leave a very fuckable hole behind. You will feel every centimeter of the pear as it rips you apart but when I’m done, your hole will still hug my cock like a virgins, for the most part.”

“Oh fuck.” Max moaned, sweat beginning to drip down his nose.

“He’s not going to stop until you do what I say. I suggest you start eating my pussy like your asshole depends on it.” Tara said in a teasing tone. For some reason Max continued to resist. The stretching, tearing pain was overwhelming his senses but the thought of Harry destroying his body for his enjoyment felt right somehow. He was Harry’s gift and Harry wanted this so it was only right to let him.

“You’ve resisted the pear. I’m impressed. I won’t go any further because I don’t want to do any permanent damage.”

“Thats’s not fair, she barely did anything.”

“Well why don’t you pick the next way we **** it out of her? Her legs are shaking a little, I doubt she can take too much more before she breaks.” Max was struggling to think. Even though Harry had stopped stretching him the unrelenting device kept his asshole pried wide open. The pain was euphoric but also almost unbearable. He groaned as he took deep breaths, trying to remain strong.

“Can her feet. And if that doesn’t work you can break her balls, I don’t care if she can’t cum for a week I need something here.” Tara was on edge, her lust and excitement overcame her normal speaking voice. Max felt a shock of joy at having gotten her so riled up. Harry returned from the wall with the cane. He unlaced Max’s boots and pulled them off. Max flexed his bare feet, trying to distract himself from his slowly tearing hole. Harry tapped the thin wooden implement against the sole of Max’s foot. Max barely registered the sensation as his brain continued to focus on the device in his ass.

“Break her.” Tara said as she humped at Max’s face. Max had all but stopped attending to her as Harry had administered his ****. Max resisted her sweet scent, his automatic response to devour her tugging at his brain. Harry delivered a swat to the middle of Max’s bare foot. It felt like a bee sting and Max yelped into Tara’s waiting pussy. Another swat to the other foot, this time closer to Max’s toes. Another surprised cry from Max.

“Harder! She’s still not cooperating.” Harry beat a rhythm of short little swats against Max’s sole. It felt like something between a sting and a tickle. Max squirmed in his restraints, each movement causing the pear to dig it’s claws into his torn flesh. Max cried out as Harry continued to whack at the bottom of Max’s feet. Max couldn’t help but struggle against his bonds. It felt like his asshole would tear in two, his tight ring struggled to hold the brutal claws and he could feel the muscle giving in. Max’s feet were red with fresh marks from the harsh wood. Max’s groans and cries grew louder as the beating continued.

“All you have to do is rub that little tongue all over my wet pussy. I can’t guarantee Harry will leave you alone but I can probably get him to slow down.” Tara was visibly wet and the smell engulfed Max. He wanted to please her but the pain was overwhelming. A deep stubbornness had taken root and he didn’t want to give in. They thought he would break so easily.

“Alright Harry. I’m running out of patience.” Harry ceased raining blows down on Max’s feet. He bent and angled the cane at Max’s exposed undercarriage. Max felt the first sting of a light swat strike the his shaft. He screamed and his body jerked, instinctively trying to run from the pain.

“That one was to his dick.” Harry reported.

“That did something.” Tara said as tears streamed down Max’s face. “She’s close to breaking.” Harry delivered another, this time to Max’s plump sack. Max screamed again.

“We’re going to have to gag him soon.” Harry said.

“I like hearing her scream. It sounds like progress.” Harry snapped the wooden menace against Max’s sack again. Max was breathing panicked now.

“Oh fuck oh fuck.” Max tried to talk himself through it. “Please.”

“There we go. That’s right, break for us.” Tara smiled.

“Please, harder. I’m your little pain slut. If you’re going to break me, you’ll have to break my body. I know you want to Harry.” Harry looked up at Tara with a grin. He reached under Max and took hold of his sack, distending it and pulling it out towards him. Max groaned as his stomach cramped. Harry took a moment to savor the view of Max’s fruit in his hand, a red slash unevenly spread across the now taut flesh. Harry raised the cane and brought it down hard, striking one of Max’s testicles with precision. Max let out a guttural scream as his body shook. Tara muffled his cries with her groin, shoving his face into her moist lips. Harry continued to smack at Max’s defenseless orbs, making sure to catch each one with the apex of the cane. Max writhed in agony as he screamed into Tara. Tara threw her head back, the vibrations of Max’s straining vocal cords resonated through her lips and clit. Max could barely understand any of what was happening. The intense pain faded away with his vision as his brain entered a state of euphoric trance. His head felt light and his body went numb. The next blow brought him back down to reality and cried out again. He couldn’t take it anymore and lapped hungrily at Tara’s clit. He swathed his tongue over every inch, he felt the rising bump of sensitive flesh and gave every ounce of his strength to lashing it with his tongue. Tara’s breath came faster as the moaning victim between her legs submitted to her will. Max’s mouth flooded with her orgasm and the beating stopped.

“Muuch better.” Tara sighed. “I knew you’d break eventually. I was about ready to grab a baseball bat.” Harry rubbed his cock with one hand as he looked at Max’s damaged scrotum. He pressed his face into the bruised sack and ran his tongue against it. He breathed deep and he could practically taste the pain and desperation. He began unscrewing the pear, slowly allowing Max’s gaping hole to swallow the device again. Max lay in a pool of Tara’s orgasm unable to think or move. His cock was rock hard but every pump of blood caused a dull thudding pain. Harry removed the pear.

“Come look.” Tara rose from the bench and walked around the broken toy. Max’s sphincter winked and spasmed unable to close completely. His pink insides flickering to his tormenters.

“So pretty!” Tara said. She bent and began rimming Max’s asshole with her tongue, savoring every broken inch. Max groaned at the sensation, pain and pleasure mixing into a dull sensation that turned his mind into mush. “Tastes so good.” Harry took his turn to savor the taste, poking his tongue into the broken hole and running it along the abused edges.

“Do you think our little butt slut deserves a reward?” Tara asked.

“Seems only fair.” Harry said, sounding almost disappointed.

“Aww, you didn’t get to cum yet did you Hare?” Tara teased.

“Not yet.”

“How do you want to cum? Our little pet seems all tuckered out. Do you want me to do it.”

“I had more planned, I’m not sure. I didn’t think Maxine here would make it this far and it’s probably too late to get a replacement. You got overzealous and broke him too early.” Harry accused Tara.

“Tell me you don’t like breaking this sweet little innocent thing and I’ll apologize. Tell me you weren’t having the time of your life destroying her asshole.” It was obvious that this fight was an echo of their ‘complicated’ relationship. Max heard them arguing as if it were a dream. His body hurt all over and he was near catatonic but the euphoric high of the come down from the **** prevented him from passing out.

“That’s not what I’m saying, but you goaded me into it. You got greedy. Now look at him. It’ll take weeks for him to recover and then what? I don’t know if he’ll even want to talk to me after this.”

“First of all, why are you calling her ‘him’? Second, poor Hare bear broke another toy. You’re only upset because you might not get to do this again.” Tara was practically yelling, defensive of her friend.

“He was a he when he joined the office and hasn’t changed his pronouns, at least not with me. And yah, this was his gift to me, I made sure he was okay with everything, I prepped him, and I had a whole plan. I was going to go easy this time and ease him into it but you got me all riled up and now who knows.”

“You call him Maxine at work!”

“I do that to tease him.”

“You’re so difficult. It’s always like this with you. You’re so fucking hot when you get a little fuck toy and start playing with it but you can’t be a man and handle the after care. Maxine is just sitting here with a broken fucking asshole and all you can think about is yourself.”

“You asked me if I wanted to cum!”

“Well do you? You can fuck me or you can fuck the hole you broke.” Tara’s anger had subsided but the fight with Harry was stirring something up in her. She couldn’t resist his energy.