Telemedicine Ch. 21: Reconfigured

"Any more whining from you..." Dr. Popova threatened.

"OK! OK," Kat said quickly. Then getting her breath, she said, "OK, so I needed someone to play the doctor part to bring you into the scene. I asked Lisa to help, and we dreamed up Dr. Popova."

"But Lisa is a submissive?" I asked.

"Which is why I thought it would be awesome for her to play Dr. Popova," Kat said.

"Tell Jonathan why," Dr. Popova said, coldly.

Kat looked at her, then at me, then said quietly, "Because I didn't think she'd be a threat to take over, and because Lisa is really hot and I didn't want you falling for her, or even meeting her."

"Finally!" said Dr. Popova. "Of course you were worried, dear. I mean Lisa is clearly the most attractive woman that Jonathan has ever seen naked, isn't that right, Jonathan?"

Oh fuck. This was a question that had no good answer. And now they were both looking at me, waiting for me to commit suicide by saying the wrong thing.

"Um..." I said, clever as always.

"Well, Jonathan," Dr. Popova said, putting her hand on her hip and staring at me. She wasn't going to let me off the hook. "Tell us both what you think of Lisa."

Now Kat was looking at me too. Dr. Popova had put her hands back on Kat's ass and was tracing circles. Her other hand found Kat's nipple and started twisting again. Kat's face was screwed up, flushed red. She was breathing hard, biting her lip, but she was looking at me. Staring at me. Waiting for me.

I wasn't sure what to say, so I just I started talking. I said, "Look, this situation here, with you both, this is the hottest, most confusing thing I've ever been involved in. I paused, waiting for a response.

I got none. They both just kept looking at me.

So I continued, "OK, you both--I mean all three of you, Doctor, Lisa, Kat, you're blowing my mind. You're all so incredibly hot, and I feel very lucky."

Still, they just stared at me.

I said, "Look, I've said this before... I'm here for Kat."

"That's the right answer, dear," said Dr. Popova. I breathed a sigh of relief.

"So let's move on to the punishment, shall we?" she said.

"Wait what?" Kat said. "You've been punishing me this entire time!"

Dr. Popova laughed and said, "I guess that's true dear. So let me clarify. Let's get to the part where I REALLY hurt you, shall we?"

Oh fuck.

"First though," she said, "Let's get Jonathan locked up again, shall we?"

She reached back into the duffle bag and pulled out my anal plug and my cage.

I groaned. My cock, despite my recent orgasm, was rock hard. There was no way I'd fit into that cage. And worse, based on past experience, once they locked me up, it would be a very long time before the were likely to let me out.

"Come here, dear," she said, motioning for me to stand in front of Kat so that Kat would have a good view. "Bend over!"

I did, and spread my cheeks without being asked. I knew that I had no choice, so I decided not to fight it. I felt the cool touch of her lubed finger at my asshole, and felt her begin to press in. Oh fuck, I didn't want to admit how good it felt, but I groaned involuntarily, giving myself away. I pushed back against her finger, trying to draw it inside of me.

"What a little slut you've become, Jonathan," she said. "It seems that there's no humiliation I can think of that doesn't make your little pussy wet."

"Yes Doctor," I said, trying to end the conversation.

I should have known that wasn't the end of it. She said, "Tell Kat how much you've come to love this feeling." She'd gotten her finger all the way inside of me, and started to twist it around, looking for, then finding my prostate.

I groaned at the pressure. I felt my cock bounce. "I like it, Kat," I said.

"That's not what I said, Jonathan." Dr. Popova said. "Tell her how much you love it!"

"Oh fuck, I do love it, Kat," I said.

"Beg me for more," the doctor said.

"Oh my god, Doctor! Please put the plug in me. Please own my asshole!" I felt myself blush, but I was also waving my hips around, trying to get more stimulation. I also knew that Kat was watching, and that made the whole thing worse. Or better. Or...I don't fucking know. All I knew is that at that moment, I would do whatever these two wanted.

"Very well, Jonathan," Dr. Popova said. I felt her finger withdraw, and then I felt her pour more lube on my upturned asshole. I felt the tip of the plug pressing firmly at my opening. Dr. Popova said, "I'm going to put this in now, but I will not take it out, ever again. Once it goes in, your ass belongs to Kat. It will be completely up to her if and when it comes out. Say it Jonathan."

Oh my god. "Once you put it in, my ass will belong to Kat!" I said.

I felt my cock bouncing up and down, as hard as it had ever been. My cuff was still massaging my balls, patiently, as it had been for what felt like hours now. I hoped that I would be able to cum while all of this was playing out. I was desperate to cum again.

"Kat," said Dr. Popova. "I'm doing this for you now, though I'm still going to punish you. Tell me to put this plug into Jonathan's ass for you."

Kat said, "Jonathan, your ass is about to belong to me." I couldn't see her face, but I could imagine her watching intently. Then she said, "Fucking do it!"

Dr. Popova slammed the plug home, so hard it took my breath away. Oh fuck!

I felt her reach for the tail that protruded from the base of the plug, then snap its magnetic connector into the slot at the base of the cuff around my balls. The plug immediately came to life, vibrating, pulsing.

"Stand up, Jonathan. Turn around. I'm going to put the cage back on your cock now."

I turned around. My cock was inches from Kat's face.

Dr. Popova said, "Oh dear, Kat. Look at that. We'll never get the cage on with him like that."

She reached for her phone, tapped a few times, and I felt the program change. My plug went quiet, but my cuff started to slowly constrict around the base of my balls. Harder. Then harder. Then harder! The pain was excruciating.

I fell to my knees, closed my eyes, and cried out, "Dr. Popova! Oh god, please stop!"

"Not until you are soft, Jonathan," she said calmly.

I opened my eyes, and there was Kat's face in front of me. I couldn't read her face, though I could see that she was still struggling with the painful program that Dr. Popova had running on her chastity belt.

"Stand up, dear boy," Dr. Popova said. "Let's get a look at that cock."

I struggled to my feet. My cock was inches from Kat's face. We could all see that the torment has softened my once raging hard-on. Dr. Popova wasted no time, pushing be backwards, lubing my semi-hard cock, then sliding the cage over my cock it until the magnets snapped home, connected to my cuff.

She tapped a few more times on her phone, and the pain around my balls stopped. In fact, my devices had gone completely quiet. In a strange way, this scared me. I felt like something really bad was about to happen.

Dr. Popova went to the duffle bag, and pulled out a paddle. "Let's begin the really painful part of the evening, shall we?" she said.

She walked over to Kat and gently rubbed the paddle over Kat's ass. She was watching the dashboard when she did it, and nothing appeared to happen. She frowned, then clicked around for a moment. I watched her adjust a bunch of settings, but I couldn't follow what she was doing. Then she walked back to Kat and rubbed the paddle over her ass once more. This time, I felt a delicious caress on my balls.

Dr. Popova smiled. She said, "Jonathan, this paddle is one of the most clever of the toys in the bag, because it can send signals to any other device."

"When Kat and I were first exploring it, she described to me what I think is the most delightful little predicament. I'm excited to finally get the chance to try it," Dr. Popova said, pausing dramatically, "....on the two of you."

She handed me the paddle, then took my free hand and walked me around the table until I was standing behind Kat, slightly off to the side. I thought I saw where this was going. Turns out, I had no idea.

"Give it a try, Jonathan," Dr. Popova said. "Give her a really good whack!"

I didn't think this was going to end well for me, but I didn't really see any way around it either, so I raised the paddle and brought it down somewhat tentatively on Kat's upturned butt.

Kat let out a grunt that seemed completely exaggerated, given that I hadn't hit her that hard. What's more, I felt my devices come alive, shocking my balls, cock, and asshole painfully.

"Fuck!" I shouted.

"Yes, that was a pathetic attempt, Jonathan," Dr. Popova said. "Tell me what you think just happened."

"I didn't hit hard enough, so I got shocked?" I asked.

"That's right. Now hit her again. Harder!"

"Kat, I'm sorry..." I said. Kat ignored me. I raised the paddle and put some muscle into it this time. It wasn't as hard as I could hit, but it was a good solid whack.

Kat grunted, "Oh FUCK!" Her whole body recoiled. This time though, my devices translated that blow into pure, intense pleasure. My cage started stroking and squeezing my cock. My cuff massaged my balls. My plug vibrated and pulsed. It felt really good. And it didn't stop, just sort of ramped down a bit as time passed.

"Do you understand what's happening here, Jonathan?" Dr. Popova said.

"Um, when I hit hard enough, the paddle hurts Kat but pleasures me?" I asked.

"My clever boy!" Dr. P said. "Indeed, Jonathan. In this configuration, the paddle's impulses are translated into terrible pain for Kat--delivered DIRECTLY to her poor, dripping pussy. The harder you hit her, the more the belt hurts her pussy. At the same time though, each blow will also stimulate her clitoris, so each time you hit her, it will bring her closer to orgasm."

"Oh god, JB," Kat cried. "I need you to make me cum. Please make me cum!"

Dr. Popova laughed. "Yes, well that isn't going to happen, Kat. Remember the scenario you described to me? I've turned on the limiter, so your stimulation will never be enough to get you over the top. Indeed, you will simply be spanked and teased."

"You fucking bitch!" Kat hissed.

"There there, dear," Dr. Popova said. "No need to get upset. This will be over soon. I will only allow Jonathan to administer fifty blows."

Oh shit. Fifty!

"On the other hand, Jonathan, I've set no limiter for your stimulation. You will be allowed to cum, provided you can get yourself there within fifty blows. You're really going to have to lean in to it though. You won't receive enough stimulation to orgasm unless you're hitting quite hard. Quite hard, really."

I really wanted to cum, but at the same time, I really didn't want to lay into Kat.

Dr. Popova said, "Jonathan, I can see from your confused face right now that you're thinking about how you can cum and also be merciful to Kat. So there's one more thing to keep in mind: if you cum, you can stop. You won't have to give her all fifty blows."

Oh my god. This was so devious.

Dr. Popova said, "Kat, you will count each blow out loud! Jonathan... begin!"

Anxiously, I raised the paddle in my right hand. I put my left hand on the small of Kat's back. I hesitated. I was about to apologize again, when Kat said, "Don't be a pussy, JB. Just fucking do it. I'm going to make you suffer plenty once I get control back, so you might as well get your shots in while you can. Hit me as hard as you can. You won't break me."

Fuck it. I raised the paddle and brought it down--hard!--on Kat's ass.

We grunted at the same time. Kat said, "One!"

I knew Kat was in pain, but holy shit this felt good. I raised my hand again, and slammed the paddle down again, this time on her other cheek..

Kat said, "Two," grunting. My devices started stroking me in earnest.

I hit her again, then again, alternating checks. Kat was counting out loud, but I wasn't paying much attention. I adjusted my stance, spreading my legs so I could get more leverage on each blow. My hesitation was gone. I felt certain that I could make myself cum this way.

When I got to ten strokes, Kat said, "Fuck, JB, I'm not sure how much I can take! Just fucking cum already!" Her voice sounded like it was breaking a little.

But I'd just had a monster orgasm in Kat's apartment a little while ago, and I was starting to get the unwelcome feeling that this next one might take a while.

I kept going.

Her ass had already turned a bright red. I ran my hand over it. It was hot to the touch. Somehow, this inflamed me. I slammed the paddle down over and over, hearing her grunt, hearing her try to get the breath to count. Watching her tight ass recoil from each blow.

"Twenty!" Shouted Kat, with a sob. Her breath was ragged, but I thought I could spare her some pain by hitting harder and harder--which is weird, but I thought I could cum and end this scene.

"Oh god, stop! Stop!," Kat shouted when we got to thirty.

I paused, unsure what to do. I wanted to spare her, but I wanted to keep hitting her. I wanted to cum. And I realized something else: I wanted to make her pay for what she'd done to me.

"Don't you dare fucking stop, Jonathan!" Dr. Popova said. I looked over at her--I'd completely forgotten about her. She was leaning against the desk. She'd taken off her jeans--standing there in only her black turtleneck, naked from the waist down. I recognized the lower half of her body of course--it was Lisa.

Still, from the waist up, she was Dr. Popova. Her face was flushed, and she stared at me intently. Her hand was working between her legs.

"Hit her!" she urged.

I got back to work, raising the paddle and bringing it down again and again. Thirty-five! Forty! My cock was insanely hard. The probe in my ass was now pulsing hard, fucking me even as I pounded Kat's ass with the paddle. Each blow brought so much stimulation now that I couldn't keep my focus.

Kat was struggling in earnest. Her eyes were closed and her head was down. She'd collapsed onto her forearms, but her ass was still thrust up in the air, meeting my blows. I had ten more strokes left. I started to feel really worried--maybe I wouldn't be able to cum after all.

I felt Dr. Popova approach, stand behind me, take my balls in her hand. Her hand was wet from her own juices. She leaned into me, pressing against my back. She'd taken off her shirt! I felt her breasts against the bare skin of my back. She pressed her lips into my ear and hissed, "Keep going!" Her breath was hot. I felt her begin to squeeze my balls--the machines and her hand now working together to bring me to the edge.

She backed away, still holding my balls, but giving me room to work. I resumed.

"Forty-one!" Kat said. "Oh god, JB, hit me harder!"

I couldn't fucking believe it. My orgasm was just out of reach, but Kat... Kat seemed like was getting closer and closer. I wondered when the limiter would kick in.

"Forty-two!" Kat was... fuck she was moaning!

"Forty-three!" It sounded like Kat was about to cum.

I kept going. "Forty-four! Oh shit!" Kat screamed.

"Fuck! Forty-five!"

Kat was writhing her hips, sobbing, gone to the world. I took my hand from the small of her back, grabbing her nipple. I twisted. She hissed, "Yessss!"

Forty-six! Dr. Popova suddenly squeezed my balls so hard that I thought I would fall over. I shouted in pain. She didn't relent, just leaned into my ear and said, "What if she cums and you don't, Jonathan?"

Fuck! I was going to try to get us both there. Forty-seven! Forty-eight!

Kat's body started shaking uncontrollably. "Ooohhhhh....." she cried.

Dr. Popova's hand grabbed my balls even harder, twisting painfully. I screamed again. Dr. Popova was going to win.

I brought the paddle down again, as hard as I could.

Kat screamed, "Oh FUCK! Fuck I'm... forty-nine! I'm cummminggggg...."

Kat collapsed on the table, quivering in pleasure. I brought the paddle down one last time, gently. There was no point. Fifty. Defeated. It was over.

My ball exploded in pain. I dropped the paddle and collapsed to my knees. I couldn't breathe.

Gradually, I felt my devices slowly quiet, then come to a stop.

I hadn't cum. And worse, Dr. Popova had somehow managed to get me to deliver the hardest possible beating to Kat. I'd wanted to be merciful, but she'd found a way to make me do my worst. I felt horrible.

But somehow, Kat had managed to cum.

It took us all a few moments to get our breath. Finally, I heard Dr. Popova begin to move around the room. I heard a series of clicks as Kat's cuffs released. When I looked up, I saw Lisa. The wig was gone. The costume was gone. She was naked. There was Lisa, wrapping wrapping Kat in a blanket.

She handed me her frilly floral robe.

Lisa said, "Ok, I lied. I set the limiter on you, not on Kat." Even delivering this news though, her voice was kind. "You were never going to cum, Robe Boy. You should have known."

I collapsed on the floor.

---------

Lisa gathered us both up, guided us to the other bedroom in the apartment. It was just someone's regular bedroom, not a set. There was a king-sized bed in there, and she led us to it, got us both under the covers, and climbed in with us, Kat in the middle, me on one side, Lisa on the other.

No one said anything for a long time. Lisa spoke first. "In the morning, I'm going to set Kat as the master user, and I'm going to delete my access."

Kat said, "Thank you."

"Jonathan, I'm going to move back into my bedroom upstairs."

I said, "OK."

"I know that Kat invited you to stay. I hope you do, but that's up to the two of you," she said.

"I'd like that," I said. "Kat, is that still OK with you?"

Kat said, "You're locked up, JB, and I'll be the only one with control...."

"I know," I said. "I want that."

We were all quiet for a bit, then I said, "What about Dr. Popova?"

Lisa said, "Tim told me that he'd be away from this apartment for the rest of lockdown. Maybe Dr Popova will come by for another visit or two before this ends..."

She paused, then said, "Who knows? I mean, how long can this pandemic thing go on?