Obey!

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Amateur

It was a lovely day and I was sitting outside the café at a table enjoying the sun. Lucky for me the view from this spot was exceptional. The storefront across the way was occupied by one of those Cross Fit places that are all the rage. Looking in the window I could see that a variety of people were working out. Men and women sweating and grunting as they pulled on ropes and hoisted various objects above their heads. One woman with a petite yet muscular physique was lifting a tire high above her head pushing her well developed and scantily clad c-cups out for all to admire. Just then a gentleman walked out and right past me. A sight to behold with pulsating muscles rippling out of his tank and an equally impressive muscle in his tight bicycle shorts. It had to be 10 inches.

At that moment I felt a sharp pain on the back of my head. My wife, Ma’am as I call her had just appeared from the café. I had been caught gawking and worse in public. She let me know it. No words where needed after the strike to my head and a deadly look. All she said was “move it!” I did not dare try to explain myself, I knew I had broken the first rule. Don’t do anything that does not serve to pleasure her. We made it to the car and then she let me have it. “You must be punished” All I said was yes Ma’am as I drove her to the party, her furiously texting all the way.

Ten minutes later we arrive and I pulled up to the curb to let her out. She looked at me and sternly said “park”. I looked quizzically at her and then quickly parked as instructed. I was confused because I was supposed to drop her off at her friends house. Another friend was getting married and so the girls were having one of those sex toy parties. You know, the ones where the ladies get together and have free champagne, get a little tipsy as they ogle at sexy lingerie and dildos that make you blush. Before I could enquire Ma’am said “Obey!” No more was needed as she instructed me to follow.

We arrived at the front door and knocked. The door opened and Gillian answered. She was wearing a fetching sun dress and already had a half empty glass in the her hand. She waved us in with an enthusiastic hello. türkçe bahis She did not seem surprised that I was in tow, I suspect that was what the texting was about. She showed us into the living room and pointed out a seat to Ma’am. She then guided me in the direction of the bedroom. I looked back and Ma’am mouthed at me “Obey”. I entered the room where Gillian had directed. Lying on the bed was all manner of items. Silky nighties, leather corsets, frilly panty sets and much more. I turned back to Gillian with a look of confusion and she said forcefully “Strip”. I hesitated and was trying to find the words to express myself when she repeated herself adding another word “Strip and Obey”. I knew I was in for it, Ma’am had something in mind to teach me a lesson and it made me uneasy to say the least.

Gillian watched intently as I removed each piece of clothing. As I did so she gave me instructions. “You are to start with the clothing items on the left and work your way to the right. Put each one on and then come out and model it. I expect you to be perky at all times and give us a good show. You will find Breast forms and make up on the dresser. There is a wig on the counter. Don’t make us wait” I was in shock! I had been punished before for such behavior but nothing like this. There was nothing to say except “Yes Gillian”.

I went as fast as I could but a good twenty minutes went by before I was ready. In the meantime the booze was flowing and the girls were ready for a show. I slowly made my way to the living room and got my courage up. I pranced out as perky as could be . I had put on the cut blonde wig and some stylish makeup. The first outfit was a red see through teddy with an opaque hart G-string. At least I was covered in the right place. I had the forms on to and they giggled as I walked. The women hooted and hollered as I spun around like a runway model showing off the outfit. I thought I was home free as all seemed pleased but then Ma’am got up and said “what took so long! You weren’t in there stoking off where you?” My cheeks burned with embarrassment.

There were at least a dozen women in the room most of whom iddaa siteleri I knew. I just quietly said no Ma’am. She just said “bend over”. I did as instructed and she said “ladies, tardiness can’t be tolerated. Please step forward and give one good slap to his ass. Make it count!” Most hesitated but our neighbor Patrice had already finished a couple drink and boldly stepped forward setting the tone she drew back her hand and stuck my right cheek with everything she had. That broke the ice and they stepped up one at a time and cheered each other on. By the time they all had a turn I was whimpering. Ma’am simply said “next”.

I came out with several more outfits. I tried to hurry each time but each time Ma’am found fault with something I did or did not do. Much to my horror this party was bondage inclusive and on the dining table was a wide assortment of whips, paddles and flogs. As the ladies drank more they lost their inhibitions and tried out the items from the table. By the third outfit tears were streaming down my face. I kept looking for Ma’am hoping for pity but found none. Just a silent “Obey”.

Finally I came out in the last outfit. It was a tight black leather corset with red trim. I wiped away my tears and pranced out as perky as ever. There were no bottoms so my manhood stood out for all to see. There where laughs and snickers at my smaller than average penis. No one was shy by this point to make comments. One women whom Ma’am worked with said loudly “I see what you mean, getting off would be difficult with that”. Ma’am said “That’s why I only let him lick my pussy, no point in putting that in. He’s very good with his tongue through. Let me show you. Boy!” With that she hiked her flowing skirt up and sat down. I knew this was my chance to please her so I did not hesitate. I got down and began to work my magic. After a few minutes she instructed me to stop. I was confused. Then she cleared it up.

The next words I heard where “Ladies show him what a real cock is like.” I glanced around and realized that I had missed some toys. Several women now had strap-ons of all shapes and sizes. I was especially horrified deneme bonusu veren siteler when I saw her friend Monique. This tiny woman has a massive ten inch cock just like the one that had gotten me in this predicament. Ma’am ordered me to resume and while I brought her to three orgasm her friend punished my ass one after another. By the end I was begging for them to stop. Then came Monique and I squealed as she rammed all 10 inches into the hilt. She fucked me like she had been waiting for this moment all her life. As she pulled out and ma’am came to that final orgasm I thought finally I am done and nearly collapsed.

Then Gillian piped up and I knew my relief was short lived. “You know, it’s not fair that you’re the only one that gets an orgasm. Surely the bride should get one last orgasm before the big day. Ma’am agreed and called the bride forward. From out of the crowd a stunning women appeared. I had never met her, friend from the gym I think, Jane. She was 5’10” with large DD breasts and a naughty smile. I tried not to show my excitement but not much gets past Ma’am. Ma’am told me to undress here and I did, still trying not to show too much excitement. Finally I removed her panties.

To my surprise was the biggest cock of the evening at least 11 inches absolutely dripping with pre-cum. Before I could look at Ma’am I heard “Obey”. I knelt down and began to suck Jane’s cock. Just then I felt Ma’am behind me. She began to stroke my swollen manhood and whispered. “Do you want to cum” I said “Yes Ma’am”. She said “don’t disappoint me, you have 3 minutes to make her cum or you don’t, Time!” She yelled and the race was on. I sucked Jane like a pro even playing with her asshole as I sucked. She was moaning and I knew she was getting close and so was I as Ma’am continued to stroke me.

Just then she came, in big gobs, one after another. I could hardly swallow fast enough. I was sure I had made the 3 minutes and then Ma’am stopped stroking. “So Sad, two seconds over”. I was totally heartbroken. It could not be. Then I heard Gillian. “We forgot this toy”. I was too disappointed to look and then I wished I had. Gillian was placing something on my dick. Just as I came around to what was happening I looked down and the lock clicked shut on the chastity device. The reality set in.

I looked up at Ma’am, cum dripping from my chin and she said. “don’t worry there is another party in a month, maybe you can cum then”.

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Telemedicine Ch. 03: Malfunction

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Bbw

CHAPTER 3: Malfunction

I resolved to make the best of the situation, but even trying my hardest, it was a tough 24 hours. After Dr. Popova ended our video chat, I did everything I could to take my mind off my situation: my junk was trapped in some diabolical medical diagnostic device. I was being blackmailed by a questionable Russian medicine practice in the middle of a pandemic. And all now that my chastity fantasies were starting to come true I was seriously in lust with my tormentor, Dr. Popova. I couldn’t stop thinking about her. I was desperate for some relief.

I thought about calling Kat, my last…, well, not girlfriend exactly. Hookup. Work friend. Whatever. I thought about calling her to see if we could do some dirty FaceTime but then I realized I couldn’t show her any of the locks on my junk and I couldn’t cum regardless, so I gave up on that idea. I tried working. I tried Netflix. I tried ordering my favorite quarantine takeout. Nothing worked. I tried to sleep, but the sirens outside and the relentless pulsing of the diagnostic cuff and cage that held my manhood made that close to impossible. Finally I took some nighttime cold medicine and was able to pass out for a few hours.

As I neared the 24 hour mark, I was excited to complete the diagnostic tests. Dr. Popova had said she would be in touch when that happened, and I was eager to be done with this, eager to get the devices off, eager to see her, eager for my reward, though I was beginning to doubt that the doctor and I shared the same ideas about what my reward might be.

Twenty-four hours passed. Twenty-five. Twenty-six. All the while the machine was pulsing slowly on my cock and balls. The action was slow and steady. Firm enough to keep me aroused, never strong enough to tip me over. And I noticed something else: whenever I was able to master my mind and stop paying attention to my cock long enough to get a bit soft, the machine would change patterns, speed, pressure. I think it was determined to keep my attention on my cock.

I was going crazy.

When I hit the 27-hour mark, I couldn’t wait any longer. I went to my desk, opened my laptop, and logged in to Dr. Popova’s telemedicine clinic. As usual, I was greeted by the chatbot. No matter what I tried though, I couldn’t make the chatbot understand that I needed to speak with Dr. Popova.

I was just about to give up in despair when I saw an email notification: Dr. Popova has sent me a new message! Hurriedly I opened it.

Jonathan Barker,

Your physician, Dr. Anna Popova has requested that we notify you with a status update regarding your diagnostic procedure. We have determined that due to your particular anatomical configuration, we must send you an additional piece of diagnostic equipment in order to complete your assessment. We understand that this may cause some inconvenience to you, so we have taken steps to ensure the device will be delivered within the next 24 hours. We apologize for this unavoidable delay.

Please contact cloud storage us immediately upon receipt of the additional equipment so that we can proceed with your diagnosis.

Sincerely,

Telemedicine Partners

I read the email again, digesting this new information. I now had an extra day to wait before I could have any relief. I felt desperate, but I was also without options. I couldn’t remove the device myself. I couldn’t get relief because I couldn’t get enough stimulation—and even if I did, I would expose myself to my blackmailers. All I could do was lie on the bed with my eyes closed, trying not to think of my cock. Trying not to picture Dr. Popova. Dr.Anna Popova. Trying not to picture her lips on my cock, her tits in my hands…

—-

The next day, UPS brought me two more packages from Telemedicine Partners. I opened the first, a small padded envelope. The packing slip described the contents as “Magnetic Charging Cable, Telemedicine Diagnostic Cuff v.3.”

The second package contained another locked black box. I immediately logged on to the web site and told the chatbot, “Please tell Dr. Popova that the diagnostic device has arrived.”

Moments later, there she was, smiling at me from the video chat window.

“Hello Jonathan, you poor dear. You must be going crazy waiting for this procedure to be complete.”

“I am Doctor. I’m very glad to see you,” I said.

“Thank you Jonathan. Let’s not waste any more time now. Do you have the package and are you ready to open it?”

I was holding it, and I nodded and held it up to show her. Moments later, I heard the latch click and I opened the box. What I saw filled me with a mix of dread and excitement.

“Dr. Popova…” I said. “Is this…?”

“Yes Jonathan. It does look very much like an anal probe, doesn’t it? That’s because it is an anal probe. You will be required to insert it in order to complete the diagnostic procedure.”

I felt despair.

“Because of your specific anatomy,” she paused and leaned in with a smile on her face. “Jonathan, it’s because of your small American penis,” she laughed, “we needed to send a supplemental sensor, and in order for it to receive accurate readings, it needs to be inserted into your anal cavity. Now hurry off to your bedside and get your personal lubricant so we can get on with this.”

I looked more closely at the device. Black, smooth, silicone, it was most definitely a butt plug. And it was not small. A flexible tail extended from the back, which I held up to show her.

“That looks a bit like a tail, doesn’t it Jonathan? That would be embarrassing, wouldn’t it?” She laughed and waited for me to say anything, but I was silent, not meeting her eye. So she continued, “It’s only the connection to the cuff. It will wrap underneath you and connect to the cuff magnetically, and that will allow it to transmit sensor data.”

I paused to take this all in.

“Jonathan, go get the lubricant,” she prompted me again. cloud file storage

When I got back, she said, “Jonathan, I am going to tell you something important now. On our first call, you refused to show me your virgin pink American asshole. Do you remember that, Jonathan?”

I nodded.

“That was a mistake. I do not like it when people refuse to do what I ask. I determined then that you would show me your asshole, and now that is what you are going to do.”

I swallowed hard. The cuff and cage were still pulsing on my cock and balls. Dr. Popova’s threat scared me, but made me hard as well.

“Jonathan, I am telling you this now for your sake. Do you really think we needed extra diagnostic sensors? Of course we didn’t. I just needed an excuse so that I could get you to open your asshole for me, do you understand?”

I nodded.

“I will continue to ask you to do things for me, Jonathan. If you do these things for me, you will always get a reward. But if you do not—if you refuse me, you will make things harder for yourself. And you will end up doing the things I want in any case, because I will always find a way to get you to do what I want. Is that clear?”

I nodded again. The seriousness of my situation was coming into clearer focus. I had thought that this would be over soon enough. That when the tests were complete, Dr. Popova would release me and we’d each go on our way. But she’d just said that this was going to continue. And she was holding all the cards. I was stunned. Too stunned to say anything. Too stunned to move.

And for fuck’s sake I was turned on as hell.

“Jonathan, would you like me to tell you what to do next?”

I desperately did want that. “Yes Dr. Popova, please tell me what to do.”

“Oh Jonathan, it makes me so happy when you say that. Now, listen carefully…”

I followed her instructions. Lube the plug. Lube my ass. Turn around. Bend over so the camera can see. Put the plug in my ass.

That last part? Easier said than done. I placed the point of the plug at my back door and pushed. This was entirely new for me—Dr. Popova was right about my virgin American asshole. And she was going to watch as I lost my cherry. I pushed harder.

“Jonathan, are you having trouble?” she laughed.

“Doctor I’ve never done this before,” I tried to explain.

“Oh my god I was right!” she exclaimed. Was she clapping her hands? I couldn’t see her face, but I imagined her delight at my predicament.

“OK Jonathan,” she said, “just press down and slowly move the probe in and out. It will go in eventually.”

I felt the plug stretching me as I worked it in. I moved it back and forth. It felt weird and it felt good. It burned and it stretched. I started fucking myself gently with the tip of the plug, keeping time to the pulsing cuff and cage on my cock. “Oh god,” I groaned.

“That’s good, Jonathan,” she said. “Go slowly now. In and out. In, Jonathan. Out. Push just a little further each file upload time.” When it was almost all the way in she said, “Now, push it all the way, Jonathan. Do it!”

I pressed and felt the plug pop into place. I gasped.

“Oh Jonathan, how beautiful!” she said, sounding so happy for me. “Now, take the tail in your hand, Jonathan and connect it to the cuff,” she said.

I did, feeling the magnetic connection click sharply into place. And instantly, the probe sprang to life, pulsing gently in the same rhythm as the cuff and cage.

“Turn around and sit in your desk chair now, Jonathan,” she said. “I will explain the rest of the procedure to you. And I want to see your face as I explain your situation to you.”

Again, I followed her orders. I sat, feeling the chair press against the plug, pushing it deeper into my ass. Everything was throbbing now—my cock, my balls, my ass. I wasn’t sure how much longer I could last.

“Dr. Popova, please!” I begged. “It’s been days. I’ve followed your instructions. Please let me remove all of your equipment. I’m begging you.”

“Are you done?” she said, suddenly cold again.

I said nothing.

“Jonathan, I asked you if you were finished with your little outburst?” she said.

I nodded meekly. The machines pulsed gently on my cock and balls. I was a wreck.

“That is good, because I have just been very very kind to you—taking your virginity so beautifully. That was a truly beautiful moment I just gave to you Jonathan. And what do you do in return? You whine like a little bitch,” she said. She paused then, and made a show of regaining her composure, squaring her shoulders, taking a deep breath.

“So now I guess we must get back to business. There will be no further reward for you today. I will simply explain how your new diagnostic probe works and then we will end our call.”

“Oh god, Doctor,” I said. I couldn’t help myself.

“Yes it is a shame,” she said, “but it can’t be helped.” She paused and then continued, “Your new diagnostic probe is similar to the cuff and cage that you are wearing. It measures certain vital body activity, and transmits data back to us. It is now beginning a cycle of measurement that should be done…” she paused and looked at her watch, “in less than a day.”

I groaned and she looked at me sharply. “I’m sorry, Doctor,” I said.

“Now this device is a little bit different than the other two. You may remove it whenever you wish and you may keep it removed for up to 15 minutes every hour. This will give you time to go to the bathroom, wash yourself, and then to reinsert the device. But I do have to warn you Jonathan, if you do not reinsert the probe and re-attach it to the cuff in a timely manner, the cuff will go into self-preservation mode. Do you remember how painful self-preservation mode is?”

I did. The memory filled me with horror. “Yes doctor, I remember.”

“Good,” she said. “I will be back in touch when the diagnostics are complete, probably within 24 hours. I will see you then.”

The screen went black. The cuff and cage pulsed slowly. The plug kept pace. My cock was harder than it’s ever been. I was leaking pre-cum all over the cage. This lockdown routine felt like it would go on forever.

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