Telemedicine Ch. 14: Entanglements

"Please proceed, Kat," said Dr. Popova. "Remember to go slowly, and please stand to the side so that I can see. This is really my favorite part."

I felt Kat's hand on my ass cheek, spreading me open. Her other hand found the flange at the base of the probe. I felt her begin to pull. I groaned, my ass clenched tight. She stopped, said, "Relax JB, or this is going to hurt."

"Kat, perhaps if you massage his testicles, that will help him relax," the doctor said.

"Ooo yeah," Kat practically squealed.

I felt her hand reach between my legs, take my balls in her palm. Christ she felt so good! She rolled my balls for a moment, then took my probe and started pressing and releasing. Oh my god, she was fucking me in and out with little pulses, pressing, releasing, rolling my balls.

"Oh.... God...." I grunted. My cock was suddenly a steel bar.

"Enough!" The doctor ordered. "There will be time for this later."

There would?!?

"Jonathan, Kat is going to remove the probe now. You had better relax or this will be very painful."

Oh shit. I felt Kat's hand on the flange of the probe. Her hand had not left my balls though and now she began squeezing firmly. Then she increased the pressure on my balls.

"Oh fuck ow! Oww!" I shouted, pathetically.

Finally, in one motion, she clamped down on my balls and pulled hard on the probe. My ass gave way, the probe popped free, and I felt a moment of blinding pain.

"Oh fuck!" I shouted.

"Ohh poor boy," said Kat, sounding not very sad at all.

"Well that was much more difficult than it should have been, don't you agree, Jonathan?" said Dr Popova, "I believe we may have to begin some serious anal training for you. You really should be able to do better after two weeks of living with that probe in your little asshole."

I just tried to catch my breath, and to avoid thinking about what "anal training" might entail.

"Now Jonathan, we are going to put you in the shower and wash you. My plan had been for you to wash yourself, but now, seeing as your hands are bound, that will be impossible. So Kat will join you in the shower to keep you safe and to perform your cleaning. Kat, please remove your clothes and start the water."

"What?" said Kat. "That wasn't the plan!"

Dr. P didn't respond. At least not verbally. Instead she responded via Kat's chastity belt. Kat doubled over, grabbed for her crotch, and cried out, "OK fuck! Stop! I'll do it, please stop!"

Dr. Popova said, "The two of you are really testing my patience tonight. I will have no more of this, do you understand? The next complaint that I hear from either of you will result in a severe punishment. Is this clear?"

"Yes, Dr. Popova," we said in unison.

"Very well. Kat...?" Dr P prompted.

Kat stripped naked, covered only by the flat black belt that held her captive. God I loved her body. She pulled back the shower curtain so that Dr. P would be able to see us, adjusted the water, then said, "OK we're ready."

I had to step into the tub to get into the shower, trickier than it sounds with your hands cuffed behind your back. Kat helped me in, then stepped in herself.

Once we were both in the water, Dr. Popova said, "Kat, please begin washing Jonathan. Avoid his private areas for now until I explain to him the choice that he will have to make."

Kat picked up the soap and began washing me. Starting on my chest. It felt incredible. The hot water, Kat's small but powerful hands, the soap. I closed my eyes and sighed. I never wanted this to end.

Dr Popova's voice interrupted my bliss. "Yes, that must feel very good, Jonathan. Imagine how Kat's hands will feel when she is washing your cock and balls and asshole."

Oh god, I wanted that.

"Kat, please wash his legs and feet, but please continue to avoid his private areas."

Kat knelt down in front of me to reach the lower half of my body. Her face was inches from my cock, which was still a raging steel bar.

"Yes, Jonathan, after all of the stimulation that you have received over the last few days, this hand-washing may very well be enough to bring you to orgasm. How lovely that would be for you!"

Suddenly, I pictured Kat's hand wrapped around my cock, a soapy handjob, blowing my load in her face. Her hands were working on my legs, my inner thighs. It felt amazing. My cock was just aching for her touch.

"Jonathan, I can see how aroused you are. And you have been very very good since you arrived at Kat's apartment. Kat and I agree that you deserve a reward. So I have decided that you have my permission to orgasm during your cleaning."

Yes!!!! I felt like I would blow the moment Kat touched me, and I couldn't wait.

"But I did say that you'd have a choice to make, so here is your choice. As I said, you may cum while Kat is cleaning you in the shower, but if you do, you will be sent home immediately following your cleaning. Kat will lock you back in your devices, and send you home, where you will remain--and remain locked--for at least one month."

Oh my god. I did NOT want to go home. And I really didn't want to be locked for another fucking month!

"On the other hand, Jonathan, if you are able to avoid cumming, then you will be allowed to stay at Kat's apartment to complete your one-week audition. You will be locked back in your devices of course, but you will have the privilege to extend your stay as Kat's guest."

Fuck.

Kat," said the doctor, "Please begin, very slowly, to wash Jonathan's testicles."

Oh my god! Kat's hands found my balls and tenderly went to work.

"Do you like this, JB?" said Kat. That exaggerated sexy porn star voice of hers. I felt like I was in a movie. After all this time, it felt so good. "I bet you can't wait to cum, huh?"

"Oh god, Kat!" was all I could say.

"Lovely," sighed Dr. Popova. Oh my god, was the Doctor getting off on this now too? I tried to see her face on the phone screen across the bathroom, but it was too small, there was water in my eyes, it was too far away.

"Yes, Jonathan," she said, "If you were here with me now, you'd see me touching myself. I do love to watch the two of you together..."

Oh god.

Kat rubbed my balls, and when Dr P said it was OK, Kat began to wash my cock. Gently, ever so gently, one soapy hand sliding up and down my cock, the other working on my balls. I was in heaven. It had been so long since I'd felt anyone's hand on my cock. And now, after all the build up...

"Gently, Kat," the doctor said, "We mustn't make him cum too soon. After all, you haven't even begun washing his tiny pink asshole. Jonathan, turn around so I can see it, and Kat, don't let go of his cock while you wash his ass."

I did as I was told, and so did Kat. She reached between my legs for my cock, and continued to work it slowly, at the same time using her other soapy hand to wash my ass, washing between my cheeks, teasing my asshole with her fingertip.

"Oh god..." I gasped.

"It feels incredible doesn't it?" Kat said. "You want to cum all over my hand, don't you JB? Don't you? I'm going to make you cum and then we're going to send you home."

"Very nice, Kat," the doctor sighed, ecstasy in her voice. "Harder now. Put your finger in his ass! Make him cum for me!"

I was so close, but Kat didn't push into my ass, she just kept lightly stroking outside. She sped up her motions on my cock, but she seemed to ease the pressure at the same time. Her teasing strokes wouldn't let me get me over the edge!

In that moment, I didn't know what I wanted. Kat's strokes felt so good. I badly wanted to cum, badly wanted the release. But god, I didn't want to go home. I didn't want to spend the next month locked up!

"Fuck!" I shouted in pure frustration. Kat was teasing me. Holding me on the edge...

"Stay strong, JB. You don't want to go home now, do you?" Kat said.

"Enough!" Dr. Popova shouted suddenly. "Kat, I believe that it is time to rinse Jonathan off," said Dr. Popova.

Behind me, Kat stopped working on me. She just patted my ass and said, "Yes, Doctor." She rinsed us both off, turned off the water, and helped me out of the shower. Kat wrapped me in a towel, rubbed me down to dry me off. My cock was still hard, and I still wanted to cum, but I was relieved that the crisis had passed. I hadn't cum! I'd be allowed to stay!

"Now Kat," said Dr. Popova, very slowly, "You've been very obedient, but I get the feeling that you weren't really trying to make Jonathan cum. In fact, I think you were going quite easy on him."

"That's not true, doctor!" Said Kat. She sounded angry. Indignant.

Now it was Dr.Popova's turn to sound indignant. She said, "Well, then you must give the shittiest handjob in New York City, because with the week that Jonathan has had, I can't imagine why else he didn't cum during that rub and tug session. Which one is it?"

Kat didn't say anything. Finally, she said, "I'd like him to stay, Dr. Popova."

"Well, isn't that wonderful!" said the doctor, her voice dripping in sarcasm. "You'd like him to stay. This is not about what you want, Kat. This is about what I want, and I wanted to see you make him cum and send him home."

Dr. Popova seemed to catch herself. She paused and took a deep breath. Then, more composed, she said, "That's what would have been best for his treatment. And it would have been best for you as well."

"I'm sorry Doctor," said Kat.

"Well," said the doctor, "Even though I don't believe that you're actually sorry, rest assured you will be before the night is over." She paused, then said, "Jonathan, you have survived the first challenge of the evening. Congratulations. You didn't cum. I am a woman who keeps her word, and thus, your privilege to stay in Kat's apartment will be extended."

Yes!

"Unfortunately, our work together tonight is not yet done," Dr. Popova said. "Kat, stand up. You have 15 minutes. You will lock Jonathan back into his devices, then you will both go to the bedroom and call me back. I will unlock Jonathan's hands and then we will begin the punishment portion of the evening."

Oh shit! Punishment?!?

Before either of us could ask Dr. Popova any questions though, she hung up.

Fuck.

----

We reconnected to the video 15 minutes later, having followed Dr. Popova's instructions. Kat had washed my devices well, and then locked me back in--first the cuff around my balls, then the cock cage, which locked shut with a little click. Finally, she lubed my asshole and inserted the probe, attaching the tail of the probe to my cuff.

We didn't speak as she did this, except as needed to get the devices on me. But as we walked down the hall to her bedroom, I wanted to say something, anything, to break the tension.

"Kat..." I started.

"Shh," she said. "Not now. We'll talk in the morning."

So I gave up. I wasn't sure what I wanted to say anyway. I just felt bad for her, because it sure seemed like she was going to get punished again.

When Dr. Popova came on video, she said, without any preliminaries, "It's important for a person who is being punished to understand why they're being punished. Kat, why am I about to punish you?"

"Um, for putting my desires ahead of yours?" Kat said,

"Yes exactly," said the doctor. "You are being punished because you undermined my will during the cleaning. You put your desires ahead of mine and failed to carry out the task that I assigned to you. So while I am punishing you, I expect you to reflect on how you can do a better job of paying attention to MY desires."

Kat didn't say anything.

"Jonathan," said the doctor, "Why am I about to punish you?"

Wait, what?!? "Um, Dr. Popova, I didn't do anything wrong! I don't deserve a punishment!"

"You are exactly right, Jonathan," the doctor said. "You did nothing wrong. But I am going to punish you anyway because it pleases me to do so. And because I can. So while you are being punished, I expect you to reflect on the absolute power that I have over you."

Fuck. Fuck. Fuck.

The doctor continued, "I quite liked your last punishment session, the one where I locked you both together and fucked your asses for an hour. Do you remember that one?"

We nodded in unison. I mean how could I fucking forget *that*?

"I have decided that we'll do something like that again. This time though I'll be watching. Watching and taking great pleasure in your suffering. Your punishment will end when I have had a sufficient amount of pleasure." I saw her lean back so that we could see her chest. She was wearing her usual black turtleneck, but no lab coat tonight. I could see her nipples, hard under her tight shirt. She brought her hands to her breasts and began to caress them. Then she said, "Kat, please go get three more sets of cuffs so we can lock you both together," Dr. Popova said.

Kat left the room, and Dr. P just sat and stroked her chest and sighed quietly until Kat came back.

Dr. Popova said, "OK, same position as last time. On the bed. Cuff yourselves ankle to ankle, then lock your hands behind each other's back."

We did what she told us to do, locking ourselves into an embrace on Kat's bed. It was fairly easy to do because Dr. Popova set the cuffs with maximum slack. When we were locked up and on the bed, I felt the whirring of the motors in the cuffs as all the slack was taken back up, locking us tightly together. This was going to be a long night.

I have to admit, it was nice to lie on Kat's bed with her. Of course, I was scared about what was coming, but I liked being wrapped up like this, feeling our naked flesh pressed together. I tried to meet her eye, but she was keeping her head turned.

"Now," said Dr. Popova, "Let me tell you about your punishment. Please, Kat, turn your face and make eye contact with Jonathan. Beginning now, and until the punishment ends, you will both be required to maintain eye contact with each other, is that clear?"

We nodded. Kat looked at me. I wanted to kiss her but I didn't dare.

The doctor continued, "Kat, your punishment program will be relatively straightforward. You will simply have a long night of pain and suffering."

"Jonathan, your punishment will be more subtle. I have programmed a routine that will give you tremendous pleasure. I believe that will enhance the experience for all of us, knowing that Kat is suffering while you enjoy yourself," said the doctor. Kat scowled. "Of course, the devices are programmed to prevent your orgasm. We certainly don't want that!"

I certainly did want that, but I kept quiet.

Then the doctor said, "Alright, let's begin, shall we?"

Immediately, I felt my devices spring to life, beginning a gentle rocking motion. At the same time, I felt Kat's body spasm, her hips jerk, and heard her shout, "Ow FUCK!"

"Kat, I'm sorry..." I said.

"Shut the fuck up, JB," she said. Then she started kissing my mouth, hard. She broke the kiss briefly, and said, "Do what you can to make this hurt less, OK?"

I felt her arms, already bound tightly behind my back pull me in even tighter, her hands grabbed my flesh. I did the same, grinding my hips into hers. Fuck it felt incredible. I kissed her, our tongues searching each other's mouth.

She broke the kiss again, "FUUUCK! OWWWWW!" She convulsed, closing her eyes, dropping her head to my shoulder.

"Eye contact!" shouted Dr. Popova.

Kat lifted her face to mine. Her eyes were pleading. She struggled to keep them open as her chastity belt sent waves and waves of pain coursing through her abdomen.

"Oh fuck! This thing is shocking my fucking pussy!" she hissed. "Fuuuuuuuuuck!" she moaned.

I was so worried for Kat. But it was so fucking hot too. It was the strangest feeling--salty and sweet at the same time, because my body felt nothing but pleasure. My cock was getting the finest robot handjob. My ass was being gently vibrated and fucked. My balls were being massaged by the cuff. Kat clung tightly to me in an embrace, her flesh warming my flesh. Her tits mashed into my chest.

I was getting close to cumming. I groaned out loud, "Oh goddddd!"

"You like this, don't you Jonathan," Dr. Popova taunted. "Oh yes, you like it as much as I do. It turns you on to hear Kat suffering. You are getting off on it just as I am. Oh, my goodness, I am so wet right now. Someday, Jonathan, I will bring you to me and you will lick my pussy while Kat watches and suffers!"

What?!? Oh fuck!

"Tell Kat how good this feels," Dr. Popova ordered.

"Oh god, Kat, I'm sorry!" I said, "It feels so good..."

"Fucker!" said Kat, struggling to spit the word in my face. I kissed her again, our eyes locked, trying to make it through this torment.

"Oh shit!" I said. I was about to cum.

At that moment, my balls exploded in pain, and I cried out. "Oh god! O fuck!" The machines would not let me cum!

"Serves you right," Kat hissed, writing under me. We rolled over, me on my back, her on top. She ground into me, staring into my eyes, biting my lip. My machines started to pleasure me again.

Kat's machines seemed to get turned up a notch.

"Oh my fucking god my pussy!" Kat called out, "Oh please! Stop please. Oh god, you're destroying me! Please stop!"

"Oh yes!" I heard Dr. Popova call out. "Oh god! Yessssssss" She was cumming. "Oh shit. Ugh! Oh yesssssssss!"

But my devices didn't stop, and neither, it seemed, did Kat's. We writhed on top of each other, waiting for some sign that Dr. P was done with us, but none came. It just kept building. Kat's eyes were closed tight now, but Dr. Popova didn't seem to notice. Where was she? Was she still with us?

Finally, after what felt like an eternity, the devices went quiet. I heard Kat panting on top of me. I felt her chest rising and falling against mine. I heard the cuffs click open, and as we began to free ourselves from our locked embrace, I looked over to the screen to see that it was black. Dr. Popova was gone.