Telemedicine Ch. 14: Entanglements

These days, getting a good night's sleep is challenging. I went to bed last night with my head full of images--the scenes with Kat, bound together during our punishment, then later, "fucking" on the couch--the conversations. The sense that Kat and Dr. Popova had an agreement that they weren't telling me about.

And I worried about what was happening between me and Kat. I mean, fuck, were we a thing? Or was this just some pandemic arrangement to help us make it through the crisis. How was all this going to end? It was hard to read her. She was cold to me one second, warm the next. She'd tell me to fuck off, or roll her eyes at me like I was stupid, then later, she'd say something sweet. And after we fucked, she was tender. Her little kisses made as much impression in my memory as those intense sex scenes.

That wasn't the only thing that made it hard to sleep though. There was also the feeling in my balls--my raging, aching, dripping need to cum. God I would do anything to finally get some relief. So yeah, there was that too.

For that, I was completely at the mercy of Kat. And both of us, in turn, were at the mercy of our crazy Russian doctor friend, Dr. Popova.

---

I was up and making coffee early. I was naked except for my devices, as Kat had instructed. My devices, mercifully, had been silent all night. I heard Kat leave her room and start a shower. I imagined her body in the shower, locked in chastity. She'd told me that the belt could be set to cleaning mode, which would split open the portion that ran between her legs to allow access so she could wash. But this mode also activated some hyper-sensitive skin sensors that reported sexual arousal. Dr. Popova would be monitoring her data feed and could administer punishment if the wearer--Kat--took liberties with her freedom.

I imagined Kat in the shower, washing, tempted to pleasure herself--fuck, I know that I'd be tempted. It reminded me that I was due to be let out for a cleaning too. I wondered if I should remind Kat about that, or if she and Dr. Popova would remember.

I heard Kat emerge from the bathroom, walk down the hall. She came into the room, and I saw that she was naked, wrapped in a towel. By that time, I'd made coffee and was sitting with my laptop on the couch. She poured herself a cup, ignoring me. I watched her take her first sip, then look at me for the first time.

"I talked to Dr P last night," she said.

"Oh yeah?" That meant that there would be some news, which of course made me worried.

"Yeah, she can be a real bitch."

I was tempted to remind her that Dr. P was always listening, but I decided that Kat had her own relationship with Dr. P and I wasn't going to get in the middle. So I waited.

Kat said, "She gave me a choice."

"Choice of what?"

"She said that I was making progress and had earned back a bit of her trust." Kat paused, thinking. Then she exhaled and said, "The choice was that I could get out of my belt, but she would retain exclusive control your devices, or I could share control of your devices again, but I'd have to stay locked up."

"Wow. What did you decide?" I asked.

She put her coffee cup down and walked out of the kitchen to stand in front of me. She opened her towel, holding it wide like a pair of wings. She was completely naked--except for her belt.

"I guess I just like controlling you, Jonathan," she said, putting on her best Dr. P accent. "Besides," she said, back in her normal voice, "Dr. P promised me that if I stayed in the belt, she'd let me cum, which is more than I can say for you!"

She was still holding her towel open, and I was staring at her tits, her impossibly perfect tits. She dropped her towel, moved her hands to her breasts, cocked her hips. She started caressing her tits, brushing her nipples, making them hard. My cock got hard in sympathy.

"You like this?" she asked.

"I love it, Kat," I said.

"Beg for what you want," she said.

"Kat, I want to get that belt off you and eat your pussy. I want to make you cum. I want to bite your nipples. I want to fucking devour you," I said.

"Yeah well, looks like it will be a while before that happens," she said. Then she said,

"Don't you want to cum yourself, Jonathan?"

I knew that this was a trap, but I didn't know how to avoid it.

"Kat, I am desperate to make you happy," I said.

She picked up her towel and wrapped herself up again. She said matter-of-factly, "Well, I know you're lying, but you get some points for the attempt."

Then she said, "Your audition is going pretty well, JB. I'm enjoying having you around. It's been lonely here since my roommate left. So don't fuck this up. I actually want you to stay, OK, but it's not up to me anymore. Part of my deal with Dr P is that she gets to decide if you stay."

"Oh shit," I said. I didn't say the rest of what I was thinking, which is that Kat must really love having control of my devices, because she was giving up a LOT for the privilege.

"Yeah, she kinda holds all the cards in this negotiation," said Kat.

Then after a minute, Kat said, "So look Dr P is going to test you later. I know what she's planning, but I'm not allowed to tell you. Just...be strong, OK?"

"That sounds scary," I said.

"You know what else is scary?" she asked, turning to leave. "I can control your shit again, JB. Dr P made me promise to get you ready for our call tonight. I'm going to fucking go to work on you, boy. All fucking day."

She walked to the doorway, let her towel fall to expose her ass, and looked back at me over her shoulder. She shook her ass at me and said, "See you later, Stud!"

----

Kat wasn't lying: she went to work on me. It was Saturday, and Kat had assigned me some chores to do around the apartment. First, she gave me a ton of laundry to do, told me where to find the laundry room in the basement of her building, and set me to work.

I'd gathered everything up, hampers, sheets, towels, put it all in a couple of big laundry bags, and then realized that Kat had confiscated all of my pants. I pulled on a t-shirt, then went to her room. The door was open, so I walked in and said, "Kat, you have all my pants."

She looked up from her computer and smiled, but didn't say anything.

"Kat, I can't go to the laundry room like this, I'll get arrested!"

"Yeah, you're right," she said. She smiled again, enjoying my predicament. Then she said, "I'm sure my roommate won't mind if you borrow one of her bathrobes."

Fuck. I walked back to the room I'd been staying in--her roommate's room--and looked around for a robe or something. Seeing nothing, I pulled open the closet, and thought, oh shit. Kat dressed about as butch as you can imagine. Jeans, t-shirts. She dressed like a skater boy, basically. But her roommate's closet was just the opposite. It smelled of perfume, and was filled with, I don't know... it looked like this girl spent a lot of time getting dressed up. There were a couple of robes hanging on hooks behind the closet door, silky floral things. One of them was pink, with feathers around the neck and hem. That was out. The other was black, printed with big flowers. I slipped it over my shoulders. The room-mate must have been small, because the thing barely fit me. It was ridiculous, short, tight across the shoulders, but it covered my ass and hid my junk. There was no tie though, no belt. I would have to hold it closed. Fuck it, I thought. This is the East Village. People have definitely seen stranger things.

I turned around and Kat was watching me. "Sexy," she said, with a smirk. She tapped a few buttons on her phone and, oh shit, now my devices started up. I felt a rolling and teasing motion on my cock, my balls, my ass.

"Fuck, Kat!," I said.

She held a pair of pink flip flops. "Put these on and then go do my laundry, JB." She laughed at my situation, waiting for my response.

Fuck it.

I grabbed my mask from my coat pocket on the way out. Somehow that made the whole thing easier--no one would see my face--then I headed down to the basement. Kat's apartment was on 12. That's a lot of stairs with too-small flip flops and two big bags of laundry on my back, but at least I didn't see anyone. My devices were still working on me, building up a rhythm now. I found the laundry room in the basement, and thankfully it was empty. I dropped the laundry bags, closed my eyes, and tried to get my shit together. My heart was pounding from the stress and stimulation.

I found a couple of free machines, and started loading them up. I was worried that someone would show up--a lot of the machines were running and this was a Saturday morning. The laundry room was bound to be busy.

I got the clothes into the washers, fired up the machines, and started to leave, thinking I'd made it out without incident. Just as I left the laundry room though and was heading for the stairs, someone came out of the elevator. A blond woman, wearing sweatpants, a tight fitting t-shirt, and a mask. She was looking at her phone, but looked up as we approached each other in the hallway. I clutched my robe closed and hurried past.

"Nice robe," she said as we passed.

"Uh... it's my girlfriend's," I said over my shoulder. "All my clothes are in the laundry."

At that moment, my devices kicked me in the balls and I cried out, stumbled, and bent double. Of course, that made my robe ride up, exposing my ass. Fuck, did she see the tail sticking out of my ass?

"Girlfriend, huh?" She said, making an exaggerated show of looking me up and down. Then, "well, you kids have fun!" She turned and headed on to the laundry room.

I made it to the stairs and back to Kat's apartment without seeing anyone else.

Kat was waiting on the couch in the living room, laptop open. She said, "have fun?"

---

The rest of the day was just as challenging. Kat programmed a truly intense tease for me. Bringing me close to orgasm over and over, never letting me cum. Sometimes I'd get close and the devices would just die. Sometimes I'd be on the edge and I'd get a painful blast in my ass, or my cock cage would squeeze until I thought amputation was imminent.

I'd had to go back and forth to the laundry room a few more times to finish the laundry. My devices always went into high gear when I left the apartment, which made for some difficult encounters. I braved some truly cold-eyed old-lady stares, but at least I didn't see the blond again. I thought that I'd die of humiliation if I ever saw her again.

The worst came late in the afternoon. I was approaching the edge again when Kat messaged me, "I'm not going to stop this time. You're going to have to control yourself. If you cum, I'm kicking your ass out."

I was in the living room. Kat had put me to work vacuuming. The devices were milking my cock, pulsing and vibrating in my ass. I killed the power on the vacuum, stood in the middle of the room. I closed my eyes. I couldn't function through this. I couldn't take any more of the tease. An orgasm was inevitable. I was going to lose. I clenched every muscle in my body. I breathed. I huffed. I puffed. I tried to think about baseball. I fucking hate baseball. It was no use, I was going to cum. I just didn't have the willpower.

The devices kept teasing and teasing, bringing me closer. I wanted to cum. I didn't want to cum. I wanted to stay. I was desperate for release. But somehow, the stimulation receded, holding me at the edge, but never letting me cum.

In the midst of this moment, the doorbell rang. Kat was in her room, and she shouted, "Answer it!"

Oh fuck! I searched for my robe--I needed something to cover my nakedness, and my devices started ratcheting up again. I ran around the apartment looking for it. Fuck, fuck fuck! Finally, I found my robe on my bed, next to the folded laundry. I threw it on and went to the door, looking through the peep-hole. Fuck, it was the blonde!

Kat had come out of her room, was standing in the hall, where she could see me at the door. She was smiling. She pulled out her phone and tapped. My devices kicked me in the balls, just hard enough to make me grunt.

I pulled on my mask and said through the door, "Who is it?"

The blond looked confused. "Kat?" she said. "I'm looking for Kat." She held up a t-shirt. "I think I found one of her shirts in the laundry room."

She held up the shirt. It was from a JavaScript camp for girls. Definitely Kat's.

Kat said, "Open the door," so I did.

The blonde took a look at me and said, "Robe boy?" She looked really puzzled now, then said, "Wait, you're KAT'S boyfriend?"

Kat called out from behind me, "Lisa! No, he's not my fucking boyfriend. Is that what he told you?"

Lisa said, "I saw him in the basement and told him that I liked his robe. He said that it belonged to his girlfriend."

I said, "Kat... it was the first thing that came to my mind!" I was pleading, honestly, scared where this might go.

Kat said, "He's not my boyfriend. He's just here to clean the apartment."

Lisa laughed. "Jesus," she said, turning to look at me again. I pulled my robe tighter. My devices were really working now, and I struggled to avoid seeming like I was getting a robot handjob. "OK, whatever you two are into. Listen, I just came by to drop this off." She held up the t-shirt. "Your, uh, cleaning boy must have left it behind in the laundry room."

"Thanks," Kat called. She didn't seem happy to see Lisa. "How careless of him. I'll see that he's properly disciplined."

Oh my god. My head was going to explode. Lisa was now openly staring at me. I was trying not to writhe obviously. She said, "I'd like to see that..."

"I bet you'd enjoy that..." said Kat.

They seemed to stare at each other for a moment, ignoring me. Then Lisa turned to leave, saying, "OK kids, I guess I'll leave you to it!"

"Bye, Lisa," Kat called after her.

"Uh, yeah, bye Lisa," I said quietly, closing the door.

Kat pulled out her phone again and my devices responded, working me even harder. Kat closed the space between us, leaning into me, bringing her face close to mine, taking my balls in her hand.

"Did you like that, JB?" Her voice was slow. Exaggerated sexy. Teasing me. "Did you think she was sexy, huh?" Oh god, what was I going to say to that? Kat just rubbed my balls and kept the dirty talk going, "Did you were going to cum in front of my sexy neighbor?"

"Kat..." I gasped. The anxiety I felt a moment ago was gone. Now it was all lust. All Kat. All about the rush to cum.

"You know, she's a bitch, but also a fuck-buddy," Kat said quietly into my ear now. She bit my ear and my knees nearly gave out. I pictured Kat and the blonde--Lisa.

"She has great fucking tits, and she gives amazing head," Kat said.

Oh fuck...

Kat said, "I love watching you struggle, JB. It makes me so fucking wet."

Then she turned off my devices, let go of my balls, kissed me on the cheek, and walked away.

I gasped.

"See you later, JB," she said.

----

"Hello you two!" Dr. Popova said.

Kat and I were sitting next to each other on the couch. I was naked except for my devices. Kat wore her javascript for girls t-shirt and jeans over her chastity belt. It was 8pm, and time for what was becoming our nightly ritual with the doctor.

"How are you both feeling?" she asked. She brushed a strand of her jet-black hair out of her eyes, behind her ear. Her lips were red, painted, perfect. Her skin impossibly pale. I wanted her. I wanted Kat. I wanted to cum. I couldn't say any of that.

We each mumbled something non-committal.

"What sparkling conversations I have with you two," she said. "Never mind. Jonathan, I have some news for you, though perhaps you already know this: Kat has elected to continue to wear her chastity belt."

"She told me, doctor," I said.

"Well yes," continued Dr. P, undeterred. "I was quite surprised. I gave her a choice to remove the belt or to control your devices, and she chose to control your devices. I suspect that she likes being locked up as much as you do."

Kat seemed to bristle next to me, but said nothing.

Dr. Popova waited, perhaps to see if Kat would respond to her taunts. When she didn't, the doctor continued, "Jonathan, tonight I am going to present you with a choice as well. It will be a difficult choice for you, but I'm certain that you will do the right thing."

"What did you have in mind, doctor?" I asked. I tried to keep my voice even, but I was starting to feel scared.

"In good time," she said. "First, we need to get you cleaned. It's been a week since your last cleaning, and we must keep you healthy, mustn't we?"

Yes! I would be getting out of these devices. The last time this happened, the doctor tricked me into putting them back on, promising me an orgasm, but delivering only a ruined orgasm, one that granted me no pleasure, no relief. I had been thinking about this moment since then, trying to game out what might happen, trying to figure out how to avoid any further traps.

Dr. Popova said, "Now, let's get you both into the bathroom and get you into the shower..."

Kat's bathroom was small--a typical NYC bathroom. We found a way, with Kat sitting on the toilet and the phone propped up on the sink, for Dr P to see what was going on.

"Now, Jonathan, I am about to unlock your devices. This is a risky moment. The last time we did this, you were alone in your apartment, and I had to offer you an orgasm to convince you to lock yourself up again when we were finished."

"Yes, I remember that," I said, with maybe too much sarcasm in my voice.

"Jonathan..." she warned. "I have been very generous with you. Do not risk the reward that you are sooo very close to claiming."

She paused. Then she said, "In fact, your attitude tells me that I cannot trust you yet. Kat, please go fetch a pair of cuffs. You will bind his hands so that he doesn't abuse this moment of liberty."

Kat smiled at me as if to say, "Haha," then stood up and left the bathroom. She was back quickly with a pair of cuffs.

"Hands behind your back, Jonathan."

What choice did I have? I could protest, earn a punishment, perhaps even lose this opportunity to be unlocked. Or I could just obey.

I obeyed. I put my hands behind my back, sighing to let everyone know what I was thinking.

"Kat, cuff his hands," said Dr. Popova.

Kat stood in front of me, took the cuffs and reached around behind me.This brought her in close to me, and she leaned in against me, looking up, smirking as she snapped the cuffs closed.

I felt that little whirring as the cable between the cuffs retracted, taking up the slack. Then I heard a set of clicks as my cuff and cage were unlocked.

"Kat, please remove Jonathan's cage and cuff, place them in the sink for washing."

I felt Kat's hands take my devices off. Oh my god it felt so good to be free! I mean kinda free. My fucking hands we're locked behind my back. Still my cock and balls were naked to the wind and I loved it.

Kat placed the devices in the sink, then turned back to me. She reached her hand out to touch my cock but stopped just short. "So close, JB, but so... so far!"

Dr Popova said, "Now Kat, this next part will be a bit tricky, so listen to me. You are going to remove Jonathan's anal probe. You will do this slowly and carefully to avoid injuring him or causing pain."

Kat smirked at me again. Perhaps she remembered when I was forced to perform a similar task on her ass. "Oh I'll be very nice to him," she said, teasingly.

"Very well," said Dr Popova, "Jonathan, please bend over so that Kat can remove your probe.

Fuck. I remembered doing this in front of both of them on video, bending over, humiliating myself, fucking myself for their pleasure. But this was different. Having Kat here... Still, what choice did I have? I turned around so that Dr. P would be able to see, then I bent at the waist and waited.