Two days later, UPS delivered a small box from a company called Telemedicine Partners with a return address in New Jersey. I opened it nervously and found a hard black plastic case inside. It looked like a lunchbox. It was locked, and I couldn't find a way to open it.
I went to my desk and opened my email and clicked the link that Dr. Popova had sent me. It led me to the web site for her clinic. I logged in, and the chatbot greeted me. Following the instructions in her email, I typed, "Please tell Dr. Popova that the diagnostic package has arrived."
It had been a hard couple of days since I had first spoken to Dr. Popova. She'd left me with a rock hard cock and explicit instructions not to cum. Maybe instructions isn't exactly the right word. She'd straight up blackmailed me—told me that she'd post the video of my exam if I didn't comply with her instructions. But she'd also promised me a reward when we next spoke, and after two nearly sleepless nights wrestling with my hard, denied cock, I was eager for that reward.
A moment later, my laptop chimed, a video chat window opened, and there was Dr. Popova. She looked almost exactly as she had when we'd last spoken, a picture of professionalism, with a hint of sex in her make-up.
"Jonathan!" She said pleasantly. She seemed actually glad to see me. "How is your abdomen? Have you had any more pain since we spoke?"
"No Dr. Popova," I said. "Nothing in my abdomen, anyway."
She looked up at me for a moment and then seemed to decide to let that pass. "And did the diagnostic equipment arrive?" she asked.
"I think so," I told her, "But I'm not sure because I can't get the case open."
"Please call me Doctor, Jonathan," she said coolly.
Fuck. "Sorry, Doctor."
"That's alright Jonathan. You'll learn. Now, give me a moment and I'll authorize the opening of the package."
I waited and then heard a small click from the box. I wondered how she was connecting to the box.
It didn't answer my question, but I was curious to see what was inside, so I opened the box. Inside there was a small, matte-black ring sitting in a black felt tray. It looked like a fancy sports watch, but smaller, and with no display.
"Pick up the ring, Jonathan," she told me. I did. It seemed to be made of hard rubber or silicone. I realized it was hinged and it opened in half. I was impressed with the design. When it was closed it was perfectly smooth and seamless, but it opened easily, and the whole thing felt solid in my hand.
"Jonathan, that is our newest blood pressure cuff. It will help us understand your condition. I'm going to tell you how to put it on now, OK?"
It seemed small for a blood pressure cuff, but I nodded.
"I want you to take off your pants for me, Jonathan. Then, you will place the ring around the base of your penis, behind your testicles."
Wait, this is cock ring that measures blood pressure? "Doctor..." I tried to ask, but she cut me off.
"Jonathan, I know this seems unusual, but this is a very good way of measuring blood pressure. It allows for extremely accurate measurements, and it's very discrete, which means that our patients can wear it all day and we can monitor continuously if we need to. Now please, put it on and then close it up so we can get on with the examination."
I did what she told me, putting the ring around the base of my cock, behind my balls, then closing the hinge. The ring made a small click as it snapped into place. I was surprised that it was a bit loose—I expected it would have to be tighter to measure blood pressure.
"Very good, Jonathan. I can see that the device is in place. Let me activate it now..." she paused for a moment, and I felt the device suddenly start to tighten on my cock. Oh shit! I...
"Jonathan, I have activated the device. You should feel that it is snug now, but it should not be tight or painful. Does it feel alright?"
After the surprise of feeling that thing come alive and embrace my cock, I realized that in fact it felt great. Just snug enough so I could feel it, it held my balls away from my body and held my cock in a firm grip. I was already semi-hard from the moment the doctor appeared on the screen, but the ring made me start to swell again. "Yes Doctor, it feels fine."
"Very good Jonathan. And I can see that we are getting preliminary data from the device now. So now we need to begin the next portion of the tests."
I felt the ring begin to tighten and then loosen.
"We are calibrating the blood pressure cuff now, Jonathan," she told me. "It may feel snug or even tight for a moment. Try to relax and let the cuff do it's work."
Sure enough, the cuff started a slow, rhythmic squeezing and releasing. It would slowly increase pressure, then release. Squeeze, then release. Squeeze. Release. It was gradually getting tighter, but it felt amazing and made my cock rock hard.
"Now this last part of the calibration may hurt a bit, Jonathan," she said. "Whatever you do, do not touch the cuff during this portion of the examination."
The ring began to squeeze hard, then harder. And it wasn't getting looser between squeezes. It just kept getting tighter.
"Ow! Fuck! Dr. Popova it really hurts. It's too tight." I was starting to panic. I reached down to pull this little fucking thing off of me, but as soon as my hand touched it, I was hit with unbearable pain—searing pain in my balls—as the ring locked down tightly on my balls. I screamed and fell to the floor.
"Oh dear, I told you not to touch the cuff," she said, from somewhere in the distance as I writhed in pain, covering my mouth with my hands, curled into a ball under my desk.
"10 more seconds, Jonathan," I heard her cool voice from my laptop speakers. "You can take that for me, I'm sure," she said.
It felt unbearable. It felt infinite. I thought it was going to snap my cock off at the root. I thought I would throw up. I couldn't breathe. I heard her say, "Three. Two. One." And then it stopped. The cuff relaxed, and all I could do was lay there, trying to catch my breath.
"Sit up, Jonathan," she said. Slowly, I did. I pulled myself up off the floor, feeling the pain still radiating from where the cuff had clamped down. When I was back in my chair, she continued, "Now listen to me very carefully, because you need to understand what I'm about to tell you."
I looked at the ring that had captured my cock and balls, but now I didn't dare touch it. It held me snug, but it was no longer tight enough to hurt me.
"Jonathan," she said, "it's very important that you follow my instructions, dear, or you *will* get hurt. Do you understand?"
I nodded, and she continued, "Good. So now... Do not touch or try to remove the cuff during operation. When you do that, the cuff will get tighter so that it can continue its operation. This is called self-preservation mode. I do not like this part of the design, but it is necessary to ensure we get accurate data."
I had my doubts about this logic, but before I could speak, she continued, "The calibration that you experienced was painful, and I'm sorry about that, but it was necessary. We need to size the device correctly, so it needs to constrict until it detects your blood supply is cut off. Surely you understand this?"
I understood that it hurt like fuck and that I was trapped in a device that might cut my cock and balls off in order to read my fucking blood pressure.
"Dr. Popova, I'd like to end this examination please," I said.
"I understand, Jonathan," she said sweetly. "Many of our patients feel the same way at this moment. Unfortunately, the protocol that we follow means that we have to complete just a few more steps before we can remove the cuff. I actually have no option to remove it at this moment."
Fuck. I was trying to figure out what to say to this when she continued, "Let's proceed to the next portion of the examination."
I sighed and said, "OK Doctor." At that, the cuff began its slow, rhythmic squeezing and releasing again. In a moment, the pain I had felt was replaced by the amazing feeling of this device massaging me gently. I watched with wonder as my cock, which had gone soft from the painful calibration, quickly got hard again.
"Open the box again, Jonathan. Lift out the tray that contained the ring. You should see another device below that on the next level."
I did what I was told. This level contained another cool black device. It looked like—fuck it looked like a hard rubber cock cage. "Um Dr. Popova," I asked, "What is this?"
"Why Jonathan, that's an additional monitor that allows us to measure blood oxygen and nerve activity. It's shaped like a cage because it allows for better data transmission."
"Oh thank god," I said. "It looks like a cock cage, Doctor," I said, laughing.
Dr. Popova just smiled, "Yes, lots of our patients think it looks that way. Especially patients like you. Patients ones that watch a lot of chastity porn on the internet."
Fuck. How did she know this? Then in a flash, I thought of the app she had installed on my phone. Could it see my browser history? Was it monitoring my other activity?
I was shocked and angry. I was more than a little scared. I was also, and I hate to admit this, hard as a rock. She had discovered my secret fantasy. Chastity. Tease. Denial. Femdom.
"Dr. Popova, are you monitoring my internet?"
The doctor was calm and cool and even pleasant. "Of course, Jonathan! How else would we be able to ensure that you're complying with our medical advice? Now please, pick up the cage and place it over your penis. We need that in place so that we can continue the examination."
Fuck, it WAS a cock cage! My head was spinning. For all the chastity porn I consumed, I'd never actually seen a cage in real life, much less had one on. Quickly though, I became concerned, because I didn't understand how I was going to get this on. There was no way this thing was going to fit over my hard-on.
"But... I don't see how this..." Again, she cut me off.
"Mr Barker!" she said. "I will explain this to you as the examination proceeds. But for now, we simply need to get the sensor array cage in place because we need the additional sensors. Now, please, do not waste anymore of my time. It is getting late here and we must proceed now, otherwise this will have to wait until tomorrow. Do you want to wait until tomorrow, Jonathan?"
I most desperately did not want to wait until tomorrow. Not with the cuff massaging my cock and balls. Not with the two days of denial. Not with the promise of my reward.
"No Doctor, I don't want to wait," I said. "Please tell me what to do."
"Jonathan," she said, brightly. "Those are my favorite words. I do so love it when my patients say, 'tell me what to do.' It makes me feel so... special. Did you like asking me what to do, Jonathan?"
I did like it, I realized, and I nodded.
"Tell me, Jonathan."
"I liked asking you what to do, Doctor," I said.
She smiled again, and said, "See! I told you that you would learn." She beamed at me for a moment and I felt like this might work out OK after all. "Now," she continued, "I want you to take the sensor array cage and place it over your penis. It has magnets in the base that will connect it to the cuff you are wearing. That connection will allow it to transmit its signals back to us. Please stand up so I can see you and guide you through this."
I stood up so that my cock was directly in front of the camera. It occurred to me that she was definitely recording this session too. If so, it would record that the cuff was still pulsing slowly around my rock-hard cock and balls, and each pulse made my cock bob up and down.
I placed the cage at the tip of my cock, but it was too small—there was no way it would fit over my hard cock.
"You are excited, Jonathan, aren't you?" Dr. Popova said. "It seems that you are fond of our little device."
"It feels good, Doctor," I admitted, though it was already obvious from the state of my erection.
"Jonathan, do you have any personal lubricant?" she asked me.
"Yes, Doctor, next to my bed," I said.
"Of course that's where it is. Many of our patients keep it there so that they can masturbate. Is that what you do with it, Jonathan? Of course that's what you do with it! I'll bet that you are going through a lot of lubricant now that you are locked down!" She laughed, then continued, "Never mind. Go get your lubricant, and come back and apply it to your penis. Then you can begin pressing the sensor array cage onto your penis. It will hurt you, but I'm sure eventually you'll be able to squeeze that little cock into that little cage." She laughed again.
I did as I was told, returning to the camera so she could watch. I diligently applied the lube to my cock, then smeared some inside the cage too for good measure. I pressed the head of my cock into the opening of the cage. She was right, this was going to hurt. I tried to breath deep and get my cock to go soft. I thought about baseball. I thought about the Knicks. I thought about work. Eventually, my cock started to soften and I was able to get the head in.
Dr. Popova had been quiet for a while, watching me, her face close to the camera. The pen between her red red lips. I had to close my eyes so I wouldn't see her lips. When I did, she said, "Jonathan, I'm getting bored here. Keep pushing, darling." I pushed, added lube, pushed some more. It hurt, but I kept going. Eventually, I was able to work the cage all the way back until it was nearly touching the cuff that hugged my balls.
"Very good Jonathan," Dr. Popova said, her voice sounding heavier now, more breathy. Her voice was really getting to me, and I felt my cock swelling at the sound of it, pressing against the cage.
"Now the last part of this procedure, Jonathan, is to push the cage down just a little bit further so that it connects to the cuff," she said. "Keep pressing, gently but firmly, until you hear a click."
Her voice had me swelling again, but I pressed on. "Gently, Jonathan. Firmly." Her voice encouraged me, but not in the right way. "Press the cage onto your penis, Jonathan," she said, "Press it!"
I pressed on, and the cage pressed painfully against my cock, until I felt it click into place, making its magnetic connection with the cuff. In the next instant, I felt the cage start to pulse in time with the cuff. Oh fuck, this was going to be too much.
"Oh god, Doctor!" I exclaimed, trying to understand what I was feeling. The mix of pain, arousal. The throbbing pulsations from the cage and cuff. I felt like I was close to blowing my load.
"Very good, Jonathan!" She said, with genuine cheerfulness and enthusiasm. "I can see the connection has been made, and I'm starting to see your enhanced data stream."
"Oh my!" she said after a short pause, "it appears that someone is aroused!" She laughed again.
"Doctor, god, I'm so close to cumming now. Please may I cum?" I was begging.
"No, not yet, Jonathan." I felt the cage the cuff slow their rhythm. "We're just beginning the enhanced diagnostics, and an orgasm now would set back our schedule. Can you be a very good boy and hold it for me?"
"I'll try, Dr. Popova," I said through gritted teeth. As much as I wanted to cum, I also really wanted to please her now.
"Very good, Jonathan," she said. "Next, I'm going to begin the diagnostic protocol. You may feel some new sensations from the sensor array cage that is currently wrapped around your penis. Most patients are able to tolerate this, but please let me know if you experience any discomfort."
Oh no, I thought, not this again! In the same moment, the pulsing stopped and—how can I describe it? Constriction is probably the best word. The constriction began. The cage and cuff held me at a tight setting, then seemed to contract and hold, then contract some more. Fuck it was definitely this again.
"Doctor, it's starting to hurt," I said. The fear in my voice surprised me.
"Thank you for telling me this, Jonathan. On a scale from 1-10, with 10 being unbearable pain and 1 being mild discomfort, please rate what you are experiencing." Her voice...it was turning me on and making my dick hard even as the cage was pressing in harder.
"It's a three, Doctor," I said.
"Very well. Continue to use your numbers to let me know what you are feeling." She said. "If this goes well, we should be done for today."
I felt the cage and cuff continue to constrict. I thought my cock would surely soften at this treatment, but it just kept getting harder. Suddenly the squeezing got firmer. Fuck! "Four, Doctor," I called out.
"Interesting," she said as if lost in thought. She placed her pen in her mouth. I imagined it was my cock. Had she touched up her lipstick while I wasn't looking? Her lips were red and sexy. I wanted to see more of her.
The device squeezed again, taking by breath away. "Fuck,OW! Five, Dr. Popova!" I blurted, my voice sounding urgent and scared.
"OK, we're almost done Jonathan, just a little longer, dear."
I wanted to last. I wanted to please her. I wanted this contraption off my cock. I wanted to cum.
Jonathan, the final phase of this test is about to begin," she said. Instantly, the cage and cuff stopped moving together and started to take turns squeezing and releasing. Cuff. Cage. Cuff. Cage. Each squeeze was hard enough to make me gasp. I could barely get by breath. I felt like I was being milked by a robot. A sexy Russian robot with red, red lips.
"Oh, verry verrry good, Jonathan," she said slowly. "I really like the data I'm seeing here. You are responding very very nicely to this stimulation."
The feelings were intense. I was on the edge of cumming. Then suddenly, the cuff took over and squeezed hard, breaking the rhythm, like an iron hand holding off my orgasm, making my eyes water. I cried out, and reached for the cuff again, realizing too late that I'd made a mistake. The cuff and cage sprang into defense mode, applying an agonizing squeeze to my most sensitive parts. I cried out and dropped to my knees. I closed my eyes, and writhed with pain under my desk.
"Fuck, make it stop, Doctor!" I shouted, but the pain continued.
"Jonathan, I told you to keep your hands away from the device. I cannot help you now. The devices must complete their self-preservation cycle. It will be over in 10 seconds." She counted down, "Five seconds. Three. Two. One. There, you should be fine now Jonathan."
At that moment, the devices released their punishing grip and resumed their pleasant pulsing movement again. I gradually caught my breath, then slowly opened my eyes. I pulled myself back up to my feet, and stood again in front of the camera, ready to resume this examination so I could remove these fucking machines and finally get some relief. I was breathing hard.
I remembered what Dr. Popova had said at the end of our last session: that I would get a reward if I obeyed her instructions.
"Doctor, I've obeyed all of your instructions so far." God listen to me. I'm panting. "I'm really looking forward to getting this done with this and..." my voice trailed off. I didn't want to upset her, but I was also beyond eager to cum.
"And what, Jonathan?" she asked me, her eyes showing a bit of pleasure. Her mouth smiling. She leaned back in her chair. "Oh, are you remembering what I told you last time?" She laughed.
She stood up for a moment and could see her take off her lab coat. I got a glimpse of black leggings. Sat down, she was wearing a tight black turtleneck. I could see the outline of her small breasts, and I could see the shape of her nipples through her shirt.