Telemedicine Ch. 07: Assignment

"Jonathan!" Dr. Popova said when she appeared on my video screen. "I am very pleased with your email."

"Thank you Doctor," I said.

"Your treatment is progressing very well. And..." she looked to the side at her diagnostic monitors, "you seem to be enjoying yourself as well."

You might think that a handjob that lasts all day, everyday—that would be a thing that you would 'enjoy,' to use Dr. P's words. You'd be wrong. But if I'd learned anything since meeting the doctor, it was that you didn't want to cross her, so I said nothing.

She didn't seem to notice though. She said, "Jonathan, I thought your email demonstrated true signs of self-awareness and growth. I'm very happy for you."

"Doctor, what am I going to do about Kat?" I asked. It really was weighing on me. As if I didn't have enough to worry about: pandemic, ambulances, lockdown, and the doctor's "treatment", now I also had a pissed off friend—one telling me just what a shitty lover I was.

"I'm glad you asked, Jonathan. That's what I want to talk about. Please stand, step back from camera, and take off clothes. I want to do inspection, then we discuss." It was weird how her Russian accent got stronger in these moments. She waited impassively, staring into the screen at me. Maybe there was a little bit of a smile at the corners of her very sexy mouth.

I did what she said, and a moment later, I was in front of the camera with nothing on except cage, cuff, and probe. I guess technically the probe was "in" and not "on," but you get my point.

"Come close to camera for inspection," she said. I saw her put on the telemedicine gloves, and felt the cage start to stroke me in time with her hand motions. I saw her left hand making come-hither motions, and felt the probe mimic them against my prostate. It felt amazing, and I groaned. My cock went from semi-hard to completely erect, filling out the cage, throbbing, dripping, aching from the long denial.

"You seem fine, Jonathan. I want you to step back so I can see your nipples. I want you to play with them for me."

For fuck's sake! This was no inspection, this was just straight-up torment. But I held my tongue for fear of what she might do. Instead, I brought both hands to my chest and began playing with my nipples. I was surprised at how good it felt—how the feeling seemed to shoot straight from my nipples to my balls. I groaned again and closed my eyes. I was on the verge of cumming.

"Stop!" she said suddenly. The devices went still, holding me firmly, but not moving. "This is very good," she said. "You are very aroused, and it is very exciting to look at you in this state. I am enjoying myself over here."

"Um... I'm glad to hear that, Doctor?" I ventured, unsure.

"I think this is what you should do for Kat," she said.

"Oh my god, fuck! No!" I was unable to control myself and instantly recognized my mistake. I saw anger cross the doctor's face and I saw her hands clamp down hard inside her gloves, felt in that instant the cage seize my cock and the cuff attack my balls. "Oh, god, please doctor! I'm sorry. Please stop!"

Her grip, her remote grip, was like iron, punishing my cock.

"Jonathan, I do not like it when you say no to me. I get what I want. Isn't that right?"

"Oh god yes, please, I'll do what you want, just please stop!"

And just like that, she relaxed her grip. The pain echoed through my loins, and I struggled to get my breath.

"You must never say no to me. And starting now, you must never say no to Kat. So far, you have said no to both of us. How do you think we feel about that, Jonathan?"

"I think you don't like it?" I asked.

She didn't bother to acknowledge my answer. Instead, she said, "It is now 6pm your time. I will give you until midnight to contact Kat and give her the show you just gave me now. You can tell her whatever you like about your situation. If you wish to tell her everything, you may do so. Do you understand?"

I nodded.

"Very good, Jonathan," she said. "You are to make a recording of the show and send it to me, do you understand?"

I nodded again. "One more thing, Jonathan," she said. "Do not refuse any of Kat's requests. If you do, there will be consequences."

She showed me her hand then, clad in the remote-control gloves. She squeezed gently, and my cock felt the pressure. I got the message.

Dr. P hung up.

--

I thought about my options for a minute or two, but really, what was I supposed to do? I texted Kat.

"Hey, can we talk?"

"Tomorrow, JB. I'm exhausted and can't deal with you tonight."

Fuck, I was desperate. If I didn't meet Dr. P's deadline, I... well, I wasn't exactly sure what would happen, but I was certain it would be painful.

I texted back, "Kat, I was an asshole. I'm sorry. Remember what you asked for? It freaked me out and I couldn't explain why. But now I can. In fact, I have to. Can we just talk sometime before midnight?"

"Tomorrow, JB."

At that moment, I don't know why, I had an idea. Pizza. Kat loves pizza.

"Tell you what. I'll send you a pizza. I'll order 2 and we can eat together. We'll talk when you're done? Just please, before midnight, OK?"

"What's with midnight? You Cinderella?"

"Something like that. Pizza incoming!"

There's a place in the East Village that Kat loves, and one of the few places that has managed to stay open during the lockdown. I called them and ordered two pies, one for each of us, and then settled down to wait.

It was hard. In every way. The whole time I was texting with Kat, the cage on my cock was pulsing, kind of milking my dick, giving me a slow, excrutiating hand-job. The cuff behind my balls was keeping time. The probe in my ass wasn't moving, thank god, but it was vibrating. The devices kept it up while I was on the phone with the pizza place. I almost couldn't remember my own fucking address. And then, once I'd put the order in, there was nothing to do but wait.

The waiting was bad, too. I worried about the delivery. Would they fuck it up? Would it be on time? I worried about my strategy too—would the bribe work? Would Kat agree to get on a call with me? But mostly, I worried about what would happen if it did work. Because if it did, it meant I was going to have to put on a show for Kat.

Eventually, I got a text from Kat. "Thanks for the pizza."

That's it? I texted back, "Wanna eat together?" but she ignored me.

I was starting to get very concerned as the night got later. I didn't want to keep texting Kat, but I didn't know what I was going to do. If I didn't make my point with her by midnight, I was fucked.

Finally I decided that I had nothing to lose. I stripped off all my clothes, stood in front of the full-length mirror, and snapped a selfie. It was all there—the cage, the cuff. For good measure, I turned around and took another over my shoulder. You could see the tail sticking out of my ass.

I texted both pictures to Kat with the message, "This is why I couldn't give you a show earlier today."

Almost instantly, my phone rang. When I picked it up, Kat was screaming with laughter. "Oh my fucking god what is WRONG with you?"

"Kat, I can explain..." I started, but she cut me off.

"I can't even believe you sent those pictures to me. Jesus Christ, JB. Are you an idiot?"

"I had to get you on the phone somehow. Actually..." but she cut me off again.

"Wait," she said, "Are you wearing that shit right now?"

"It's all locked on, Kat. I can't take it off."

"No way," she said. "Show me, JB. Video, now!"

It wasn't a request. It was an order. Either way, Dr. Popova has made it clear that-request or order-it didn't matter. I had to do whatever Kat asked.

I texted her a link to my video meeting room, connected her when she called in, and hit record immediately so that I'd have proof for Dr. P. Oddly, as soon as the video connected, all of the devices went still.

I didn't have time to think about that. I was still naked, and now Kat sat at the other end of the video call, staring at me in stunned silence. I was humiliated beyond anything I've ever felt. And yet my cock was rock hard.

Kat seemed to be trying to make sense of what she was seeing. Finally, she said, "Stand up, JB." I did, and I moved back so she could see me.

"So that's a cock cage?" She asked.

"Yes," I said. "And a ring around my balls, and a plug in my ass. Kat, it's a long story, but I need to tell you the whole thing."

She just smiled and made a motion with her hands like, 'go ahead' so that's what I did. I sat down and told her the whole thing.

When I was done, she said, "So wait, this Russian doctor lady says that you have to do anything I ask, and you can't say no?"

"That's right. In fact, I'm recording this call right now and I have to send her the proof by midnight or I get punished again."

She looked at her watch then smiled. "It's 10 o'clock JB," she said, "that means I have 2 hours to do anything I want with you?"

"More or less," I said. "I probably need a few minutes to get the recording to her."

But Kat didn't seem to be paying a lot of attention to that. She seemed to be lost in thought. Finally, smiling, she said, "OK, stand up and show me your trapped cock up close, JB. I've never seen one before. I wanna see it. Stand up. Now!"

She was barking orders, but there was laughter in her voice.

I showed her my cock. I'd backed off from the edge while I was telling her my story. But now, standing up and showing her my cock, I started to grow again. I moved closer to the camera and brought my caged cock into the frame. My cock kept growing until it was pressing against the cage. It was painful, but it was exactly what Kat wanted to see at that moment, so...

"Fuck that's hot, JB," she said. "Turn around so that I can see that plug in your ass." I did what I was told.

"I thought you said that those things moved. Why can't I see any movement?" she asked.

"I don't know, Kat. They're not running now, and I'm not sure why," I said. "Like I said, I can't control the settings. Sometimes I think that they run on a program. Other times, I think that Dr. P is monitoring my activity and changing the settings on me. Honestly, I can't fucking figure it out and it's making me crazy."

"Wait," Kat said. "You think she's listening to this call?"

"I can't tell. All I know is that the devices seem to know what I'm doing in some uncanny way. They stop, they start. Honestly Kat, they've been teasing the fuck out of me and I am desperate to get off."

Kat seemed to shift in her seat. "God, JB. That's making me wet." She bit her lip and looked at me through the video screen. She reached under her desk, and I got even harder imagining her hand in her pants.

"I'm supposed to give you the show you asked for Kat." I didn't have the vaguest idea how to do that. I'm no stripper-I'm a fucking geek programmer-but the clock was ticking and I wanted to get on with it already. I was worried about what would happen if I missed my deadline.

"Yeah, I want to see that," Kat said, "Play with yourself, JB. I'm going to watch you play with yourself and I'm going to sit right here at my desk with my shirt on and my pants off and you're not going to see a thing but I'm going to get myself off while I watch you. Do you like that idea, JB?"

I groaned and nodded. We locked eyes through the screen and I saw her hands moving under her desk. She leaned back and sighed, her eyes locked on the screen. "Fucking play with yourself, JB."

I was in a bind. If I didn't do what she said, I was sure Dr. Popova would punish my balls. If I did put my hands on my cock, I was scared that the devices would enter self-defense mode and I'd get my balls crushed from that. Then I remembered what Dr. P had told me. She'd told me to play with my nipples, and relieved, I started to do that. It was humiliating as fuck, but it also felt really good. I closed my eyes and sighed.

Then, all of a sudden, all my hardware came to life. The cage started rocking on my cock, squeezing and milking. The probe in my ass started fucking me slowly.

"Oh god, Kat!" I hissed. "They've come alive!"

"Show me!" she said, her jaw clenched, her eyes half-closed with concentration and pleasure.

I came in closer to the camera. The pulsing cage was squeezing pre-cum from the tip of my cock. I was breathing hard, and Kat matched my breath on the other side of the line.

"Tell me what's happening, JB," she said.

"Oh god, the cage is giving me a hand-job. It's so intense. I'm so fucking close I can't stand it. The fucking probe in my..." I didn't want to say it.

"Say it, JB. Tell me where that big fucking dick is fucking you."

"Fuck, Kat. The probe is fucking me in the ass. Oh god it's too much." I had started to sway my hips back and forth, side to side, anything to get more friction, anything to get enough friction to cum.

"Don't you dare cum!" She ordered. "You owe me JB, you selfish bastard. This time I'm the one who gets off..." She was leaning into the camera, staring straight at me when her orgasm hit. "Oh GOD, JB! OH GOD OH GOD OH FUCK!" she called out. Her head fell back and I watched the breath catch in her throat.

"Oh god, JB," she said, "That was so good." She took a deep breath. I was still playing with my nipples. Still swaying my hips.

"Stop, JB," she said. "Tell your doctor if she's listening to stop fucking you. You're not cumming tonight."

Oh god. I stopped moving, stopped playing with my nipples. I had known that I wasn't going to get to cum, but still, some irrational part of me had been hoping. It crushed me to hear this, but I said, "Dr. P, if you can hear me, please shut off the devices."

And just like that, they stopped.

"She heard you?" Kat asked.

"Seems that way," I panted.

"Holy shit that's hot, JB," she said. She paused to look at me for a moment, tilting her head. "You must really want to cum, huh?" she said.

I did, and I nodded.

"And you have the recording, right JB? The one you're supposed to send to your 'Russian doctor'?" She made scare quotes with her fingers as she said this.

I nodded. The entire reason for this session was to get the recording and send it to Dr. P.

"And you have to do what I say?" she asked.

I nodded again, starting to get really worried.

She laughed, and looked at the ceiling, like she was considering her options. "This is going to be fun, JB," she said. "So when you send her a copy, you're going to send me a copy too. You know why?"

I shook my head.

"Because starting today, JB,"she said, "it's not just this Russian doctor lady who owns you. Starting today, I own you too."

My head was spinning. I had thought I had hit bottom so many times in this crisis. First with my health crisis, then with Dr. P's blackmail. Each day it got worse. But with each passing day, I had the same strange thought—now matter where I thought I was, I was nowhere close to bottom.

"I'll talk to you tomorrow, JB," Kat said, sighing. "In the meantime, please tell your doctor that you made me very happy tonight with your little performance. As a reward, you may ask her to tease you mercilessly tonight so that you're warmed up and ready for me tomorrow. And JB, I'll be very very disappointed if you cum accidentally, so... well, don't cum. And have a good night."

Kat leaned in close to the camera and blew me a kiss. My heart sank. My cock throbbed. And I realized—I had no idea where the bottom was.